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A high-resolution X-ray diffraction data set was collected within 48 h at 100 K with synchrotron radiation and area detection. A full topological analysis was applied to the resulting electron-density model. This analysis was followed by a Bader partitioning making use of the zero-flux surfaces of the electron-density gradient vector field. The atomic and bonding properties obtained were compared with the results of previous experimental studies, and with theoretical calculations for the title complex and free tryptophan as reported in the literature. The agreement between experiment and theory is similar to the agreement between different theoretical calculations. There is no charge transfer via the strong hydrogen bond; however, its strength is indicated by the very small atomic volume of the H atom involved.
Keywords: atomic volumes; atomic charges; topological analysis; hydrogen bonding; L-tryptophan formic acid.
Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768104001739/lc5002sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S0108768104001739/lc5002sup2.hkl |
CCDC reference: 237248
Computing details top
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to refine structure: Koritsanszky et al., (1995); molecular graphics: Koritsanszky et al., (1995); software used to prepare material for publication: Koritsanszky et al., (1995).
![[Figure 1]](http://journals.iucr.org/b/issues/2004/02/00/lc5002/lc5002fig1thm.gif)
![[Figure 2]](http://journals.iucr.org/b/issues/2004/02/00/lc5002/lc5002fig2thm.gif)
![[Figure 3]](http://journals.iucr.org/b/issues/2004/02/00/lc5002/lc5002fig3thm.gif)
![[Figure 4]](http://journals.iucr.org/b/issues/2004/02/00/lc5002/lc5002fig4thm.gif)
![[Figure 5]](http://journals.iucr.org/b/issues/2004/02/00/lc5002/lc5002fig5thm.gif)
![[Figure 6]](http://journals.iucr.org/b/issues/2004/02/00/lc5002/lc5002fig6thm.gif)
![[Figure 7]](http://journals.iucr.org/b/issues/2004/02/00/lc5002/lc5002fig7thm.gif)
(TRP) top
Crystal data top
| C11H12N2O2·CH2O2 | F(000) = 528 |
| Mr = 250.25 | Dx = 1.418 (1) Mg m−3 |
| Orthorhombic, P212121 | Synchrotron radiation, λ = 0.54 Å |
| Hall symbol: P 2ac 2ab | Cell parameters from 20000 reflections |
| a = 5.2951 (3) Å | θ = 2.6–48.0° |
| b = 8.1213 (4) Å | µ = 0.07 mm−1 |
| c = 27.256 (2) Å | T = 100 K |
| V = 1172.1 (1) Å3 | Block, colorless |
| Z = 4 | 0.40 × 0.35 × 0.30 mm |
Data collection top
| Bruker SMART 1000 CCD Detector at DESY
HASYLAB beamline F1
on kappa-axis diffractometer | Rint = 0.030 |
| ω and ϕ scans | θmax = 48.2° |
| 62915 measured reflections | h = −14→7 |
| 12305 independent reflections | k = −22→10 |
| 10905 reflections with I > 2.5 σ(I) | l = −65→64 |
Refinement top
| Refinement on F | H atoms treated by a mixture of independent and constrained refinement |
| R[F2 > 2σ(F2)] = 0.022 | Weighting scheme based on measured s.u.'s |
| wR(F2) = 0.023 | (Δ/σ)max = 0.00017 |
| S = 1.24 | Δρmax = 0.21 e Å−3 |
| 10905 reflections | Δρmin = −0.21 e Å−3 |
| 541 parameters |
Crystal data top
| C11H12N2O2·CH2O2 | V = 1172.1 (1) Å3 |
| Mr = 250.25 | Z = 4 |
| Orthorhombic, P212121 | Synchrotron radiation, λ = 0.54 Å |
| a = 5.2951 (3) Å | µ = 0.07 mm−1 |
| b = 8.1213 (4) Å | T = 100 K |
| c = 27.256 (2) Å | 0.40 × 0.35 × 0.30 mm |
Data collection top
| Bruker SMART 1000 CCD Detector at DESY
HASYLAB beamline F1
on kappa-axis diffractometer | 10905 reflections with I > 2.5 σ(I) |
| 62915 measured reflections | Rint = 0.030 |
| 12305 independent reflections |
Refinement top
| R[F2 > 2σ(F2)] = 0.022 | 541 parameters |
| wR(F2) = 0.023 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.24 | Δρmax = 0.21 e Å−3 |
| 10905 reflections | Δρmin = −0.21 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| O(13) | 0.05013 (5) | 0.29898 (3) | 0.80595 (1) | 0.014 | |
| O(14) | 0.44577 (5) | 0.36845 (3) | 0.78505 (1) | 0.015 | |
| O(16) | −0.21364 (17) | 0.78722 (5) | 0.84594 (2) | 0.031 | |
| O(17) | −0.04622 (9) | 0.59723 (4) | 0.79712 (1) | 0.020 | |
| N(1) | 0.83318 (5) | 0.17992 (4) | 0.95223 (1) | 0.016 | |
| N(15) | 0.63013 (5) | 0.06745 (3) | 0.79510 (1) | 0.012 | |
| C(2) | 0.71161 (6) | 0.06734 (4) | 0.92275 (1) | 0.015 | |
| C(3) | 0.50652 (5) | 0.13896 (3) | 0.90035 (1) | 0.012 | |
| C(4) | 0.33361 (5) | 0.43977 (3) | 0.91043 (1) | 0.014 | |
| C(5) | 0.38175 (6) | 0.58767 (3) | 0.93410 (1) | 0.017 | |
| C(6) | 0.59315 (6) | 0.60658 (4) | 0.96508 (1) | 0.018 | |
| C(7) | 0.75932 (6) | 0.47704 (4) | 0.97335 (1) | 0.016 | |
| C(8) | 0.70770 (5) | 0.32762 (4) | 0.94969 (1) | 0.013 | |
| C(9) | 0.49886 (5) | 0.30670 (3) | 0.91771 (1) | 0.012 | |
| C(10) | 0.32950 (5) | 0.05244 (3) | 0.86605 (1) | 0.013 | |
| C(11) | 0.36443 (4) | 0.09308 (3) | 0.81129 (1) | 0.011 | |
| C(12) | 0.28346 (5) | 0.26903 (3) | 0.79916 (1) | 0.011 | |
| C(18) | −0.16415 (7) | 0.64421 (4) | 0.83613 (1) | 0.018 | |
| H(1) | 0.98376 | 0.15746 | 0.97333 | 0.048 | |
| H(2) | 0.78417 | −0.05685 | 0.92129 | 0.049 | |
| H(4) | 0.17463 | 0.42813 | 0.88585 | 0.031 | |
| H(5) | 0.26019 | 0.69178 | 0.92699 | 0.043 | |
| H(6) | 0.63490 | 0.72195 | 0.98305 | 0.037 | |
| H(7) | 0.91759 | 0.48225 | 0.99830 | 0.038 | |
| H(11) | 0.25638 | 0.00731 | 0.78946 | 0.034 | |
| H(10A) | 0.35129 | −0.07915 | 0.86990 | 0.034 | |
| H(10B) | 0.13577 | 0.08500 | 0.87375 | 0.029 | |
| H(15A) | 0.73651 | 0.16792 | 0.79987 | 0.042 | |
| H(15B) | 0.70948 | −0.02561 | 0.81353 | 0.056 | |
| H(15C) | 0.62678 | 0.03669 | 0.75958 | 0.041 | |
| H(17) | −0.00135 | 0.47130 | 0.79669 | 0.062 | |
| H(18) | −0.21940 | 0.54928 | 0.86172 | 0.046 |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O(13) | 0.01140 (6) | 0.01222 (6) | 0.01916 (8) | 0.00206 (6) | −0.00004 (6) | −0.00184 (6) |
| O(14) | 0.01414 (7) | 0.01302 (6) | 0.01926 (9) | 0.00074 (6) | 0.00164 (7) | 0.00507 (6) |
| O(16) | 0.0504 (3) | 0.0144 (1) | 0.0269 (2) | 0.0144 (1) | −0.0008 (2) | −0.0014 (1) |
| O(17) | 0.0277 (1) | 0.0143 (1) | 0.0188 (1) | 0.0044 (1) | 0.0044 (1) | 0.0035 (1) |
| N(1) | 0.01397 (6) | 0.02121 (9) | 0.01368 (7) | 0.00372 (7) | −0.00255 (6) | 0.00067 (6) |
| N(15) | 0.01244 (6) | 0.01141 (5) | 0.01293 (6) | 0.00193 (5) | 0.00104 (5) | −0.00151 (5) |
| C(2) | 0.01503 (7) | 0.01601 (8) | 0.01326 (7) | 0.00453 (7) | −0.00015 (6) | 0.00163 (6) |
| C(3) | 0.01232 (6) | 0.01220 (6) | 0.01079 (5) | 0.00161 (6) | 0.00028 (5) | 0.00060 (5) |
| C(4) | 0.01409 (6) | 0.01287 (6) | 0.01442 (7) | 0.00208 (6) | −0.00072 (6) | −0.00115 (5) |
| C(5) | 0.01928 (9) | 0.01303 (7) | 0.01743 (8) | 0.00071 (7) | 0.00092 (7) | −0.00212 (6) |
| C(6) | 0.0202 (1) | 0.0162 (1) | 0.0163 (1) | −0.0041 (1) | 0.0016 (1) | −0.0034 (1) |
| C(7) | 0.01546 (8) | 0.02056 (9) | 0.01342 (7) | −0.00412 (8) | −0.00012 (6) | −0.00229 (6) |
| C(8) | 0.01195 (6) | 0.01733 (8) | 0.01105 (6) | −0.00019 (6) | −0.00029 (5) | −0.00048 (5) |
| C(9) | 0.01130 (5) | 0.01259 (6) | 0.01068 (5) | 0.00088 (6) | 0.00005 (5) | −0.00013 (5) |
| C(10) | 0.01331 (6) | 0.01115 (6) | 0.01324 (7) | −0.00095 (6) | 0.00128 (5) | 0.00084 (5) |
| C(11) | 0.01136 (6) | 0.00956 (5) | 0.01183 (6) | 0.00030 (5) | −0.00007 (5) | −0.00124 (4) |
| C(12) | 0.01125 (6) | 0.01018 (5) | 0.01191 (6) | 0.00126 (5) | −0.00029 (5) | −0.00008 (4) |
| C(18) | 0.0245 (1) | 0.0115 (1) | 0.0188 (1) | 0.0063 (1) | 0.0011 (1) | 0.0013 (1) |
Geometric parameters (Å, º) top
| O(13)—C(12) | 1.2728 (3) | C(4)—C(9) | 1.4046 (3) |
| O(14)—C(12) | 1.2404 (3) | C(4)—H(4) | 1.08 |
| O(16)—C(18) | 1.2202 (5) | C(5)—C(6) | 1.4106 (5) |
| O(17)—C(18) | 1.2908 (5) | C(5)—H(5) | 1.08 |
| O(17)—H(17) | 1.05 | C(6)—C(7) | 1.3899 (5) |
| N(1)—C(2) | 1.3769 (5) | C(6)—H(6) | 1.08 |
| N(1)—C(8) | 1.3730 (4) | C(7)—C(8) | 1.4011 (4) |
| N(1)—H(1) | 1.00 | C(7)—H(7) | 1.08 |
| N(15)—H(15A) | 1.00 | C(8)—C(9) | 1.4183 (3) |
| N(15)—H(15B) | 1.00 | C(10)—C(11) | 1.5397 (4) |
| N(15)—H(15C) | 1.00 | C(10)—H(10A) | 1.08 |
| C(2)—C(3) | 1.3749 (4) | C(10)—H(10B) | 1.08 |
| C(2)—H(2) | 1.08 | C(11)—C(12) | 1.5281 (3) |
| C(3)—C(9) | 1.4426 (3) | C(11)—H(11) | 1.08 |
| C(3)—C(10) | 1.4989 (4) | C(18)—H(18) | 1.08 |
| C(4)—C(5) | 1.3872 (4) | ||
| C(18)—O(17)—H(17) | 114.00 | C(6)—C(7)—H(7) | 124.31 |
| C(2)—N(1)—C(8) | 108.93 (3) | C(8)—C(7)—H(7) | 118.36 |
| C(2)—N(1)—H(1) | 125.97 | N(1)—C(8)—C(7) | 129.72 (3) |
| C(8)—N(1)—H(1) | 125.05 | N(1)—C(8)—C(9) | 107.68 (3) |
| H(15A)—N(15)—H(15B) | 108.34 | C(7)—C(8)—C(9) | 122.60 (3) |
| H(15A)—N(15)—H(15C) | 109.86 | C(3)—C(9)—C(4) | 134.24 (2) |
| H(15B)—N(15)—H(15C) | 107.753 | C(3)—C(9)—C(8) | 107.02 (2) |
| N(1)—C(2)—C(3) | 110.33 (3) | C(4)—C(9)—C(8) | 118.71 (2) |
| N(1)—C(2)—H(2) | 118.37 | C(3)—C(10)—C(11) | 115.41 (2) |
| C(3)—C(2)—H(2) | 131.28 | C(3)—C(10)—H(10A) | 109.67 |
| C(2)—C(3)—C(9) | 106.03 (2) | C(3)—C(10)—H(10B) | 110.98 |
| C(2)—C(3)—C(10) | 124.93 (2) | C(11)—C(10)—H(10A) | 107.06 |
| C(9)—C(3)—C(10) | 129.02 (2) | C(11)—C(10)—H(10B) | 104.48 |
| C(5)—C(4)—C(9) | 119.08 (3) | H(10A)—C(10)—H(10B) | 108.96 |
| C(5)—C(4)—H(4) | 120.50 | C(10)—C(11)—C(12) | 112.115 (16) |
| C(9)—C(4)—H(4) | 120.39 | C(10)—C(11)—H(11) | 109.396 |
| C(4)—C(5)—C(6) | 121.24 (3) | C(12)—C(11)—H(11) | 109.589 |
| C(4)—C(5)—H(5) | 119.00 | O(13)—C(12)—O(14) | 126.39 (2) |
| C(6)—C(5)—H(5) | 119.68 | O(13)—C(12)—C(11) | 114.81 (2) |
| C(5)—C(6)—C(7) | 121.13 (3) | O(14)—C(12)—C(11) | 118.78 (2) |
| C(5)—C(6)—H(6) | 121.89 | O(16)—C(18)—O(17) | 124.46 (4) |
| C(7)—C(6)—H(6) | 116.98 | O(16)—C(18)—H(18) | 118.67 |
| C(6)—C(7)—C(8) | 117.23 (3) | O(17)—C(18)—H(18) | 116.87 |
Experimental details
| Crystal data | |
| Chemical formula | C11H12N2O2·CH2O2 |
| Mr | 250.25 |
| Crystal system, space group | Orthorhombic, P212121 |
| Temperature (K) | 100 |
| a, b, c (Å) | 5.2951 (3), 8.1213 (4), 27.256 (2) |
| V (Å3) | 1172.1 (1) |
| Z | 4 |
| Radiation type | Synchrotron, λ = 0.54 Å |
| µ (mm−1) | 0.07 |
| Crystal size (mm) | 0.40 × 0.35 × 0.30 |
| Data collection | |
| Diffractometer | Bruker SMART 1000 CCD Detector at DESY
HASYLAB beamline F1
on kappa-axis diffractometer |
| Absorption correction | – |
| No. of measured, independent and observed [I > 2.5 σ(I)] reflections | 62915, 12305, 10905 |
| Rint | 0.030 |
| (sin θ/λ)max (Å−1) | 1.380 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.022, 0.023, 1.24 |
| No. of reflections | 10905 |
| No. of parameters | 541 |
| No. of restraints | ? |
| H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
| Δρmax, Δρmin (e Å−3) | 0.21, −0.21 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), Koritsanszky et al., (1995).
Selected geometric parameters (Å, º) top
| O(13)—C(12) | 1.2728 (3) | C(4)—C(9) | 1.4046 (3) |
| O(14)—C(12) | 1.2404 (3) | C(4)—H(4) | 1.08 |
| O(16)—C(18) | 1.2202 (5) | C(5)—C(6) | 1.4106 (5) |
| O(17)—C(18) | 1.2908 (5) | C(5)—H(5) | 1.08 |
| O(17)—H(17) | 1.05 | C(6)—C(7) | 1.3899 (5) |
| N(1)—C(2) | 1.3769 (5) | C(6)—H(6) | 1.08 |
| N(1)—C(8) | 1.3730 (4) | C(7)—C(8) | 1.4011 (4) |
| N(1)—H(1) | 1.00 | C(7)—H(7) | 1.08 |
| N(15)—H(15A) | 1.00 | C(8)—C(9) | 1.4183 (3) |
| N(15)—H(15B) | 1.00 | C(10)—C(11) | 1.5397 (4) |
| N(15)—H(15C) | 1.00 | C(10)—H(10A) | 1.08 |
| C(2)—C(3) | 1.3749 (4) | C(10)—H(10B) | 1.08 |
| C(2)—H(2) | 1.08 | C(11)—C(12) | 1.5281 (3) |
| C(3)—C(9) | 1.4426 (3) | C(11)—H(11) | 1.08 |
| C(3)—C(10) | 1.4989 (4) | C(18)—H(18) | 1.08 |
| C(4)—C(5) | 1.3872 (4) | ||
| C(18)—O(17)—H(17) | 114.00 | C(6)—C(7)—H(7) | 124.31 |
| C(2)—N(1)—C(8) | 108.93 (3) | C(8)—C(7)—H(7) | 118.36 |
| C(2)—N(1)—H(1) | 125.97 | N(1)—C(8)—C(7) | 129.72 (3) |
| C(8)—N(1)—H(1) | 125.05 | N(1)—C(8)—C(9) | 107.68 (3) |
| H(15A)—N(15)—H(15B) | 108.34 | C(7)—C(8)—C(9) | 122.60 (3) |
| H(15A)—N(15)—H(15C) | 109.86 | C(3)—C(9)—C(4) | 134.24 (2) |
| H(15B)—N(15)—H(15C) | 107.753 | C(3)—C(9)—C(8) | 107.02 (2) |
| N(1)—C(2)—C(3) | 110.33 (3) | C(4)—C(9)—C(8) | 118.71 (2) |
| N(1)—C(2)—H(2) | 118.37 | C(3)—C(10)—C(11) | 115.41 (2) |
| C(3)—C(2)—H(2) | 131.28 | C(3)—C(10)—H(10A) | 109.67 |
| C(2)—C(3)—C(9) | 106.03 (2) | C(3)—C(10)—H(10B) | 110.98 |
| C(2)—C(3)—C(10) | 124.93 (2) | C(11)—C(10)—H(10A) | 107.06 |
| C(9)—C(3)—C(10) | 129.02 (2) | C(11)—C(10)—H(10B) | 104.48 |
| C(5)—C(4)—C(9) | 119.08 (3) | H(10A)—C(10)—H(10B) | 108.96 |
| C(5)—C(4)—H(4) | 120.50 | C(10)—C(11)—C(12) | 112.115 (16) |
| C(9)—C(4)—H(4) | 120.39 | C(10)—C(11)—H(11) | 109.396 |
| C(4)—C(5)—C(6) | 121.24 (3) | C(12)—C(11)—H(11) | 109.589 |
| C(4)—C(5)—H(5) | 119.00 | O(13)—C(12)—O(14) | 126.39 (2) |
| C(6)—C(5)—H(5) | 119.68 | O(13)—C(12)—C(11) | 114.81 (2) |
| C(5)—C(6)—C(7) | 121.13 (3) | O(14)—C(12)—C(11) | 118.78 (2) |
| C(5)—C(6)—H(6) | 121.89 | O(16)—C(18)—O(17) | 124.46 (4) |
| C(7)—C(6)—H(6) | 116.98 | O(16)—C(18)—H(18) | 118.67 |
| C(6)—C(7)—C(8) | 117.23 (3) | O(17)—C(18)—H(18) | 116.87 |
