Supporting information
Crystallographic Information File (CIF) | |
Structure factor file (CIF format) | |
Portable Document Format (PDF) file |
CCDC reference: 132061
C7H8N2O2 | Z = 4 |
Mr = 152.00 | F(000) = 187.744 |
Monoclinic, P21/n | Dx = 1.423 Mg m−3 |
Hall symbol: -P 2yn | Neutron radiation, λ = 0.5-5.0 Å |
a = 9.369 (2) Å | Cell parameters from 120 reflections |
b = 5.563 (1) Å | µ = 0.09 mm−1 |
c = 13.626 (3) Å | T = 100 K |
β = 92.36 (3)° | Irregular prism, orange |
V = 709.6 (2) Å3 | 5 × 3 × 2 mm |
SXD diffractometer | 3386 independent reflections |
Radiation source: ISIS spallation source | 3386 reflections with I > 2σ(I) |
None monochromator | Rint = 0.060 |
Time of flight LAUE diffraction scans | θmax = 21.5°, θmin = 1.1° |
Absorption correction: empirical (using intensity measurements) The linear absorption coefficient is wavelength dependent and it is calculated as: mu = 0.93 + 0.89 * lambda [cm-1] | h = 0→24 |
Tmin = 0.47, Tmax = 0.85 | k = 0→13 |
17278 measured reflections | l = −30→27 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.067 | All H-atom parameters refined |
wR(F2) = 0.154 | Calculated w = 1/[σ2(Fo2) + (0.1119P)2 + 1.3458P] where P = (Fo2 + 2Fc2)/3 |
S = 1.14 | (Δ/σ)max = −0.001 |
3386 reflections | Δρmax = 5.08 e Å−3 |
172 parameters | Δρmin = −2.01 e Å−3 |
0 restraints | Extinction correction: Becker-Coppens Lorentzian model |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.325 |
C7H8N2O2 | V = 709.6 (2) Å3 |
Mr = 152.00 | Z = 4 |
Monoclinic, P21/n | Neutron radiation, λ = 0.5-5.0 Å |
a = 9.369 (2) Å | µ = 0.09 mm−1 |
b = 5.563 (1) Å | T = 100 K |
c = 13.626 (3) Å | 5 × 3 × 2 mm |
β = 92.36 (3)° |
SXD diffractometer | 3386 independent reflections |
Absorption correction: empirical (using intensity measurements) The linear absorption coefficient is wavelength dependent and it is calculated as: mu = 0.93 + 0.89 * lambda [cm-1] | 3386 reflections with I > 2σ(I) |
Tmin = 0.47, Tmax = 0.85 | Rint = 0.060 |
17278 measured reflections |
R[F2 > 2σ(F2)] = 0.067 | 0 restraints |
wR(F2) = 0.154 | All H-atom parameters refined |
S = 1.14 | Δρmax = 5.08 e Å−3 |
3386 reflections | Δρmin = −2.01 e Å−3 |
172 parameters |
Experimental. Because of the kind of experiment, it is not possible to give values of theta_min and theta_max for the cell determination. Instead, we can give values of cell_measurement_sin(theta)/lambda_min 0.145 cell_measurement_sin(theta)/lambda_max 0.660 The same applies for the wavelength used for the experiment. The range of wavelengths used was 0.5–5 Angstroms |
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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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. The extinction coefficient reported in _refine_ls_extinction_coef is in this case the refined value of the mosaic spread in units of 10-4 rad-1 |
x | y | z | Uiso*/Ueq | ||
C1 | 1.00918 (9) | 0.1891 (2) | 0.29213 (8) | 0.00944 (14) | |
C2 | 0.96433 (9) | −0.0194 (2) | 0.23937 (7) | 0.00990 (14) | |
C3 | 0.86971 (10) | −0.1782 (2) | 0.28168 (8) | 0.0116 (2) | |
C4 | 0.81377 (10) | −0.1356 (2) | 0.37340 (8) | 0.01124 (15) | |
C5 | 0.85647 (9) | 0.0742 (2) | 0.42127 (7) | 0.00891 (13) | |
C6 | 0.95266 (9) | 0.2355 (2) | 0.38383 (7) | 0.00966 (14) | |
C7 | 1.01863 (11) | −0.0674 (2) | 0.13949 (9) | 0.0164 (2) | |
N1 | 1.10806 (9) | 0.34293 (15) | 0.25496 (7) | 0.01679 (15) | |
N2 | 0.79435 (7) | 0.13194 (13) | 0.51505 (6) | 0.01191 (12) | |
O1 | 0.6994 (2) | 0.0025 (3) | 0.54424 (12) | 0.0237 (3) | |
O2 | 0.8377 (2) | 0.3094 (3) | 0.56024 (11) | 0.0207 (3) | |
H3 | 0.8379 (3) | −0.3399 (5) | 0.2419 (2) | 0.0298 (6) | |
H4 | 0.7401 (3) | −0.2593 (5) | 0.4065 (2) | 0.0314 (6) | |
H6 | 0.9826 (3) | 0.3960 (5) | 0.4244 (2) | 0.0281 (5) | |
H11 | 1.1247 (3) | 0.5013 (5) | 0.2891 (3) | 0.0329 (6) | |
H12 | 1.1320 (3) | 0.3373 (6) | 0.1841 (2) | 0.0324 (6) | |
H71 | 1.1340 (3) | −0.0916 (8) | 0.1416 (3) | 0.0405 (8) | |
H72 | 0.9955 (5) | 0.0843 (7) | 0.0895 (3) | 0.0425 (8) | |
H73 | 0.9713 (4) | −0.2277 (7) | 0.1067 (3) | 0.0407 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0104 (3) | 0.0105 (3) | 0.0076 (4) | −0.0012 (2) | 0.0023 (2) | −0.0004 (2) |
C2 | 0.0105 (3) | 0.0118 (3) | 0.0075 (4) | 0.0007 (2) | 0.0009 (2) | −0.0021 (2) |
C3 | 0.0123 (3) | 0.0108 (3) | 0.0118 (4) | −0.0013 (2) | 0.0009 (2) | −0.0031 (3) |
C4 | 0.0121 (3) | 0.0106 (3) | 0.0111 (4) | −0.0022 (2) | 0.0019 (2) | −0.0007 (3) |
C5 | 0.0102 (3) | 0.0097 (3) | 0.0070 (4) | −0.0010 (2) | 0.0020 (2) | 0.0000 (2) |
C6 | 0.0117 (3) | 0.0101 (3) | 0.0074 (4) | −0.0022 (2) | 0.0022 (2) | −0.0013 (2) |
C7 | 0.0168 (4) | 0.0219 (5) | 0.0109 (5) | 0.0010 (3) | 0.0035 (3) | −0.0054 (3) |
N1 | 0.0200 (3) | 0.0174 (3) | 0.0135 (4) | −0.0063 (2) | 0.0073 (2) | −0.0012 (2) |
N2 | 0.0129 (2) | 0.0148 (3) | 0.0083 (3) | −0.0015 (2) | 0.0036 (2) | −0.0005 (2) |
O1 | 0.0284 (6) | 0.0262 (6) | 0.0176 (7) | −0.0106 (5) | 0.0132 (5) | −0.0025 (5) |
O2 | 0.0252 (5) | 0.0231 (6) | 0.0144 (7) | −0.0067 (4) | 0.0084 (4) | −0.0074 (4) |
H3 | 0.0349 (12) | 0.0244 (11) | 0.030 (2) | −0.0086 (9) | 0.0047 (10) | −0.0119 (9) |
H4 | 0.0315 (11) | 0.0297 (12) | 0.034 (2) | −0.0133 (9) | 0.0101 (10) | −0.0006 (10) |
H6 | 0.0357 (12) | 0.0254 (11) | 0.0237 (14) | −0.0090 (9) | 0.0063 (9) | −0.0085 (9) |
H11 | 0.0408 (14) | 0.0246 (11) | 0.034 (2) | −0.0114 (10) | 0.0114 (11) | −0.0060 (10) |
H12 | 0.0372 (13) | 0.0398 (15) | 0.0210 (14) | −0.0081 (11) | 0.0120 (11) | −0.0011 (10) |
H71 | 0.0237 (11) | 0.059 (2) | 0.039 (2) | 0.0035 (12) | 0.0090 (11) | −0.011 (2) |
H72 | 0.059 (2) | 0.047 (2) | 0.022 (2) | 0.008 (2) | 0.0091 (14) | 0.0050 (13) |
H73 | 0.049 (2) | 0.041 (2) | 0.032 (2) | −0.0116 (14) | 0.0089 (13) | −0.0167 (13) |
C1—N1 | 1.3734 (11) | C5—N2 | 1.4615 (12) |
C1—C6 | 1.4011 (13) | C6—H6 | 1.081 (3) |
C1—C2 | 1.4187 (13) | C7—H71 | 1.088 (3) |
C2—C3 | 1.3934 (13) | C7—H72 | 1.101 (4) |
C2—C7 | 1.4964 (15) | C7—H73 | 1.084 (3) |
C3—C4 | 1.3953 (15) | N1—H11 | 1.006 (3) |
C3—H3 | 1.086 (3) | N1—H12 | 1.001 (3) |
C4—C5 | 1.3878 (14) | N2—O1 | 1.2235 (15) |
C4—H4 | 1.086 (3) | N2—O2 | 1.224 (2) |
C5—C6 | 1.3840 (12) | ||
N1—C1—C6 | 119.95 (9) | C5—C6—C1 | 119.00 (8) |
N1—C1—C2 | 120.85 (8) | C5—C6—H6 | 120.4 (2) |
C6—C1—C2 | 119.19 (8) | C1—C6—H6 | 120.6 (2) |
C3—C2—C1 | 119.27 (9) | C2—C7—H71 | 111.9 (2) |
C3—C2—C7 | 120.60 (9) | C2—C7—H72 | 111.1 (2) |
C1—C2—C7 | 120.13 (9) | H71—C7—H72 | 106.3 (3) |
C2—C3—C4 | 122.11 (9) | C2—C7—H73 | 111.9 (2) |
C2—C3—H3 | 119.0 (2) | H71—C7—H73 | 107.3 (3) |
C4—C3—H3 | 118.9 (2) | H72—C7—H73 | 108.0 (4) |
C5—C4—C3 | 116.90 (8) | C1—N1—H11 | 118.0 (2) |
C5—C4—H4 | 120.9 (2) | C1—N1—H12 | 121.2 (2) |
C3—C4—H4 | 122.2 (2) | H11—N1—H12 | 116.0 (3) |
C6—C5—C4 | 123.47 (9) | O1—N2—O2 | 122.79 (11) |
C6—C5—N2 | 117.95 (8) | O1—N2—C5 | 118.42 (10) |
C4—C5—N2 | 118.57 (8) | O2—N2—C5 | 118.78 (9) |
H12—N1—C1—C2 | 15.9 (3) | H11—N1—C1—C2 | 170.2 (3) |
H12—N1—C1—C6 | −164.9 (3) | H11—N1—C1—C6 | −10.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H12···O1i | 1.001 (3) | 2.219 (4) | 3.149 (2) | 154.0 (3) |
N1—H12···O2i | 1.001 (3) | 2.738 (4) | 3.585 (2) | 142.7 (3) |
N1—H11···O1ii | 1.004 (3) | 2.321 (3) | 3.199 (2) | 145.3 (3) |
C3—H3···C(Ph)iii | 1.085 (3) | 2.608 (3) | 3.414 (1) | 130.5 (2) |
C4—H4···O1 | 1.086 (3) | 2.418 (4) | 2.713 (2) | 93.7 (2) |
C6—H6···O2 | 1.081 (3) | 2.389 (3) | 2.706 (2) | 94.9 (2) |
C6—H6···O2ii | 1.081 (3) | 2.353 (3) | 3.275 (2) | 142.2 (2) |
C7—H71···O2i | 1.088 (3) | 2.740 (4) | 3.525 (2) | 128.8 (3) |
C7—H71···O1iv | 1.088 (3) | 2.725 (4) | 3.255 (2) | 109.5 (3) |
C7—H73···O1iv | 1.084 (4) | 2.789 (4) | 3.255 (2) | 105.8 (2) |
Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (ii) −x+2, −y+1, −z+1; (iii) −x+3/2, y−1/2, −z+1/2; (iv) x+1/2, −y−1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C7H8N2O2 |
Mr | 152.00 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 100 |
a, b, c (Å) | 9.369 (2), 5.563 (1), 13.626 (3) |
β (°) | 92.36 (3) |
V (Å3) | 709.6 (2) |
Z | 4 |
Radiation type | Neutron, λ = 0.5-5.0 Å |
µ (mm−1) | 0.09 |
Crystal size (mm) | 5 × 3 × 2 |
Data collection | |
Diffractometer | SXD diffractometer |
Absorption correction | Empirical (using intensity measurements) The linear absorption coefficient is wavelength dependent and it is calculated as: mu = 0.93 + 0.89 * lambda [cm-1] |
Tmin, Tmax | 0.47, 0.85 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17278, 3386, 3386 |
Rint | 0.060 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.067, 0.154, 1.14 |
No. of reflections | 3386 |
No. of parameters | 172 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 5.08, −2.01 |
Computer programs: SHELXL93 (Sheldrick, 1993).
C1—N1 | 1.3734 (11) | C5—N2 | 1.4615 (12) |
C1—C6 | 1.4011 (13) | C6—H6 | 1.081 (3) |
C1—C2 | 1.4187 (13) | C7—H71 | 1.088 (3) |
C2—C3 | 1.3934 (13) | C7—H72 | 1.101 (4) |
C2—C7 | 1.4964 (15) | C7—H73 | 1.084 (3) |
C3—C4 | 1.3953 (15) | N1—H11 | 1.006 (3) |
C3—H3 | 1.086 (3) | N1—H12 | 1.001 (3) |
C4—C5 | 1.3878 (14) | N2—O1 | 1.2235 (15) |
C4—H4 | 1.086 (3) | N2—O2 | 1.224 (2) |
C5—C6 | 1.3840 (12) | ||
N1—C1—C6 | 119.95 (9) | C5—C6—C1 | 119.00 (8) |
N1—C1—C2 | 120.85 (8) | C5—C6—H6 | 120.4 (2) |
C6—C1—C2 | 119.19 (8) | C1—C6—H6 | 120.6 (2) |
C3—C2—C1 | 119.27 (9) | C2—C7—H71 | 111.9 (2) |
C3—C2—C7 | 120.60 (9) | C2—C7—H72 | 111.1 (2) |
C1—C2—C7 | 120.13 (9) | H71—C7—H72 | 106.3 (3) |
C2—C3—C4 | 122.11 (9) | C2—C7—H73 | 111.9 (2) |
C2—C3—H3 | 119.0 (2) | H71—C7—H73 | 107.3 (3) |
C4—C3—H3 | 118.9 (2) | H72—C7—H73 | 108.0 (4) |
C5—C4—C3 | 116.90 (8) | C1—N1—H11 | 118.0 (2) |
C5—C4—H4 | 120.9 (2) | C1—N1—H12 | 121.2 (2) |
C3—C4—H4 | 122.2 (2) | H11—N1—H12 | 116.0 (3) |
C6—C5—C4 | 123.47 (9) | O1—N2—O2 | 122.79 (11) |
C6—C5—N2 | 117.95 (8) | O1—N2—C5 | 118.42 (10) |
C4—C5—N2 | 118.57 (8) | O2—N2—C5 | 118.78 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H12···O1i | 1.001 (3) | 2.219 (4) | 3.149 (2) | 154.0 (3) |
N1—H12···O2i | 1.001 (3) | 2.738 (4) | 3.585 (2) | 142.7 (3) |
N1—H11···O1ii | 1.004 (3) | 2.321 (3) | 3.199 (2) | 145.3 (3) |
C3—H3···C(Ph)iii | 1.085 (3) | 2.608 (3) | 3.414 (1) | 130.5 (2) |
C4—H4···O1 | 1.086 (3) | 2.418 (4) | 2.713 (2) | 93.7 (2) |
C6—H6···O2 | 1.081 (3) | 2.389 (3) | 2.706 (2) | 94.9 (2) |
C6—H6···O2ii | 1.081 (3) | 2.353 (3) | 3.275 (2) | 142.2 (2) |
C7—H71···O2i | 1.088 (3) | 2.740 (4) | 3.525 (2) | 128.8 (3) |
C7—H71···O1iv | 1.088 (3) | 2.725 (4) | 3.255 (2) | 109.5 (3) |
C7—H73···O1iv | 1.084 (4) | 2.789 (4) | 3.255 (2) | 105.8 (2) |
Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (ii) −x+2, −y+1, −z+1; (iii) −x+3/2, y−1/2, −z+1/2; (iv) x+1/2, −y−1/2, z−1/2. |