Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520615010410/lo5002sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520615010410/lo50021aHClH2Osup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520615010410/lo50021bsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520615010410/lo50021bHClH2Osup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520615010410/lo50021c3H2Osup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520615010410/lo50022aHClsup6.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520615010410/lo5002sup7.pdf |
CCDC references: 1020040; 1020041; 1020042; 1020043; 1020044
Data collection: CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) for 1aHClH2O, 1bHClH2O, 1c3H2O; CrysAlis PRO, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) for 2aHCl. Cell refinement: CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) for 1aHClH2O, 1bHClH2O, 1c3H2O; CrysAlis PRO, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) for (1b), 2aHCl. Data reduction: CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) for 1aHClH2O, 1bHClH2O, 1c3H2O; CrysAlis PRO, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) for (1b), 2aHCl. For all compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).
C11H11N2O·Cl·H2O | Dx = 1.347 Mg m−3 |
Mr = 240.68 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pcab | Cell parameters from 895 reflections |
a = 5.1830 (6) Å | θ = 4.2–21.3° |
b = 16.808 (7) Å | µ = 0.31 mm−1 |
c = 27.247 (3) Å | T = 293 K |
V = 2373.7 (11) Å3 | Needle-like, colourless |
Z = 8 | 0.35 × 0.15 × 0.05 mm |
F(000) = 1008 |
Xcalibur, Ruby, Gemini ultra diffractometer | 2083 independent reflections |
Radiation source: fine-focus sealed tube | 1332 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.076 |
Detector resolution: 10.3712 pixels mm-1 | θmax = 25.0°, θmin = 3.9° |
ω scans | h = −5→6 |
Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | k = −19→12 |
Tmin = 0.946, Tmax = 0.985 | l = −28→32 |
6343 measured reflections |
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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0287P)2] where P = (Fo2 + 2Fc2)/3 |
1986 reflections | (Δ/σ)max < 0.001 |
153 parameters | Δρmax = 0.19 e Å−3 |
3 restraints | Δρmin = −0.16 e Å−3 |
C11H11N2O·Cl·H2O | V = 2373.7 (11) Å3 |
Mr = 240.68 | Z = 8 |
Orthorhombic, Pcab | Mo Kα radiation |
a = 5.1830 (6) Å | µ = 0.31 mm−1 |
b = 16.808 (7) Å | T = 293 K |
c = 27.247 (3) Å | 0.35 × 0.15 × 0.05 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 2083 independent reflections |
Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | 1332 reflections with I > 2σ(I) |
Tmin = 0.946, Tmax = 0.985 | Rint = 0.076 |
6343 measured reflections |
R[F2 > 2σ(F2)] = 0.061 | 3 restraints |
wR(F2) = 0.110 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.19 e Å−3 |
1986 reflections | Δρmin = −0.16 e Å−3 |
153 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.8942 (4) | 0.18538 (15) | 0.11090 (7) | 0.0541 (7) | |
N1 | 0.5206 (4) | 0.11706 (18) | 0.05702 (9) | 0.0463 (7) | |
C5 | 0.7475 (5) | 0.1448 (2) | 0.13474 (10) | 0.0374 (8) | |
C11 | 0.6126 (5) | 0.0862 (2) | 0.21558 (11) | 0.0462 (9) | |
H11 | 0.4779 | 0.0596 | 0.2001 | 0.055* | |
C7 | 0.9792 (5) | 0.1712 (2) | 0.21171 (11) | 0.0455 (9) | |
H7 | 1.0937 | 0.2021 | 0.1936 | 0.055* | |
C10 | 0.6457 (6) | 0.0788 (2) | 0.26558 (12) | 0.0553 (10) | |
H10 | 0.5335 | 0.0473 | 0.2838 | 0.066* | |
C6 | 0.7787 (5) | 0.13299 (19) | 0.18821 (10) | 0.0342 (7) | |
C4 | 0.5233 (5) | 0.1041 (2) | 0.10980 (10) | 0.0483 (9) | |
H4B | 0.5323 | 0.0474 | 0.1162 | 0.058* | |
H4A | 0.3634 | 0.1238 | 0.1237 | 0.058* | |
C9 | 0.8433 (6) | 0.1178 (3) | 0.28833 (12) | 0.0552 (10) | |
H9 | 0.8642 | 0.1130 | 0.3221 | 0.066* | |
C8 | 1.0118 (6) | 0.1642 (2) | 0.26184 (12) | 0.0531 (9) | |
H8 | 1.1463 | 0.1905 | 0.2775 | 0.064* | |
C2 | 0.3604 (6) | 0.1671 (2) | 0.03172 (12) | 0.0560 (11) | |
H2 | 0.2292 | 0.1981 | 0.0450 | 0.067* | |
N2 | 0.6292 (5) | 0.1116 (2) | −0.01854 (10) | 0.0575 (8) | |
H2N | 0.7089 | 0.0989 | −0.0451 | 0.069* | |
C3 | 0.4269 (6) | 0.1632 (3) | −0.01550 (13) | 0.0591 (10) | |
H3 | 0.3501 | 0.1904 | −0.0414 | 0.071* | |
C1 | 0.6837 (6) | 0.0841 (2) | 0.02569 (12) | 0.0563 (11) | |
H1 | 0.8135 | 0.0480 | 0.0334 | 0.068* | |
Cl1 | 0.96604 (15) | 0.03832 (6) | −0.09885 (3) | 0.0548 (3) | |
O2 | 0.1390 (6) | 0.2143 (2) | 0.87505 (12) | 0.0786 (9) | |
H2O | −0.004 (4) | 0.2391 (19) | 0.873 (2) | 0.15 (3)* | |
H2P | 0.101 (7) | 0.1656 (6) | 0.8792 (19) | 0.13 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0528 (12) | 0.063 (2) | 0.0463 (13) | −0.0127 (12) | 0.0053 (11) | 0.0107 (12) |
N1 | 0.0432 (14) | 0.056 (2) | 0.0394 (15) | −0.0027 (14) | −0.0009 (13) | −0.0011 (15) |
C5 | 0.0354 (16) | 0.037 (2) | 0.0399 (18) | 0.0049 (15) | 0.0026 (15) | −0.0040 (17) |
C11 | 0.0490 (18) | 0.044 (3) | 0.046 (2) | −0.0082 (17) | 0.0010 (15) | 0.0044 (17) |
C7 | 0.0446 (17) | 0.044 (2) | 0.047 (2) | −0.0029 (16) | 0.0051 (15) | 0.0012 (17) |
C10 | 0.058 (2) | 0.063 (3) | 0.044 (2) | −0.0015 (19) | 0.0072 (18) | 0.0137 (19) |
C6 | 0.0339 (15) | 0.026 (2) | 0.0423 (17) | 0.0025 (14) | 0.0033 (14) | −0.0006 (15) |
C4 | 0.0491 (18) | 0.059 (3) | 0.0364 (18) | −0.0079 (18) | 0.0033 (14) | 0.0018 (17) |
C9 | 0.066 (2) | 0.062 (3) | 0.0368 (18) | 0.014 (2) | 0.0001 (18) | 0.0009 (19) |
C8 | 0.0538 (19) | 0.055 (3) | 0.051 (2) | −0.0039 (19) | −0.0049 (18) | −0.0069 (19) |
C2 | 0.0536 (19) | 0.069 (3) | 0.045 (2) | 0.014 (2) | −0.0051 (17) | −0.004 (2) |
N2 | 0.0719 (18) | 0.065 (3) | 0.0360 (16) | 0.0002 (18) | 0.0061 (14) | −0.0077 (16) |
C3 | 0.068 (2) | 0.061 (3) | 0.049 (2) | 0.012 (2) | −0.0121 (18) | 0.000 (2) |
C1 | 0.059 (2) | 0.068 (3) | 0.042 (2) | 0.0138 (19) | −0.0019 (18) | −0.005 (2) |
Cl1 | 0.0702 (5) | 0.0481 (6) | 0.0459 (5) | 0.0082 (5) | 0.0014 (4) | 0.0022 (5) |
O2 | 0.0796 (18) | 0.059 (3) | 0.097 (2) | −0.0085 (18) | −0.0066 (16) | 0.0090 (19) |
O1—C5 | 1.211 (3) | C4—H4B | 0.9700 |
N1—C1 | 1.323 (4) | C4—H4A | 0.9700 |
N1—C2 | 1.368 (4) | C9—C8 | 1.375 (5) |
N1—C4 | 1.455 (4) | C9—H9 | 0.9300 |
C5—C6 | 1.479 (4) | C8—H8 | 0.9300 |
C5—C4 | 1.510 (4) | C2—C3 | 1.334 (4) |
C11—C10 | 1.379 (4) | C2—H2 | 0.9300 |
C11—C6 | 1.384 (4) | N2—C1 | 1.321 (4) |
C11—H11 | 0.9300 | N2—C3 | 1.363 (4) |
C7—C6 | 1.380 (4) | N2—H2N | 0.8600 |
C7—C8 | 1.381 (4) | C3—H3 | 0.9300 |
C7—H7 | 0.9300 | C1—H1 | 0.9300 |
C10—C9 | 1.365 (4) | O2—H2O | 0.8500 (11) |
C10—H10 | 0.9300 | O2—H2P | 0.8501 (13) |
C1—N1—C2 | 108.7 (3) | C5—C4—H4A | 109.1 |
C1—N1—C4 | 124.6 (3) | H4B—C4—H4A | 107.8 |
C2—N1—C4 | 126.6 (3) | C10—C9—C8 | 120.7 (3) |
O1—C5—C6 | 122.4 (3) | C10—C9—H9 | 119.7 |
O1—C5—C4 | 119.8 (3) | C8—C9—H9 | 119.7 |
C6—C5—C4 | 117.8 (3) | C9—C8—C7 | 119.4 (3) |
C10—C11—C6 | 120.4 (3) | C9—C8—H8 | 120.3 |
C10—C11—H11 | 119.8 | C7—C8—H8 | 120.3 |
C6—C11—H11 | 119.8 | C3—C2—N1 | 107.4 (3) |
C6—C7—C8 | 120.7 (3) | C3—C2—H2 | 126.3 |
C6—C7—H7 | 119.6 | N1—C2—H2 | 126.3 |
C8—C7—H7 | 119.6 | C1—N2—C3 | 109.4 (3) |
C9—C10—C11 | 119.9 (3) | C1—N2—H2N | 125.3 |
C9—C10—H10 | 120.0 | C3—N2—H2N | 125.3 |
C11—C10—H10 | 120.0 | C2—C3—N2 | 106.8 (3) |
C7—C6—C11 | 118.9 (3) | C2—C3—H3 | 126.6 |
C7—C6—C5 | 118.5 (3) | N2—C3—H3 | 126.6 |
C11—C6—C5 | 122.6 (3) | N2—C1—N1 | 107.8 (3) |
N1—C4—C5 | 112.6 (2) | N2—C1—H1 | 126.1 |
N1—C4—H4B | 109.1 | N1—C1—H1 | 126.1 |
C5—C4—H4B | 109.1 | H2O—O2—H2P | 106.24 (19) |
N1—C4—H4A | 109.1 | ||
C6—C11—C10—C9 | 0.0 (5) | C6—C5—C4—N1 | −177.2 (3) |
C8—C7—C6—C11 | −1.1 (5) | C11—C10—C9—C8 | −0.4 (6) |
C8—C7—C6—C5 | 177.9 (3) | C10—C9—C8—C7 | 0.2 (6) |
C10—C11—C6—C7 | 0.8 (5) | C6—C7—C8—C9 | 0.6 (5) |
C10—C11—C6—C5 | −178.2 (3) | C1—N1—C2—C3 | 0.7 (4) |
O1—C5—C6—C7 | 1.5 (5) | C4—N1—C2—C3 | 178.0 (3) |
C4—C5—C6—C7 | −178.6 (3) | N1—C2—C3—N2 | −0.7 (4) |
O1—C5—C6—C11 | −179.5 (3) | C1—N2—C3—C2 | 0.5 (4) |
C4—C5—C6—C11 | 0.4 (4) | C3—N2—C1—N1 | −0.1 (4) |
C1—N1—C4—C5 | 72.4 (4) | C2—N1—C1—N2 | −0.4 (4) |
C2—N1—C4—C5 | −104.5 (4) | C4—N1—C1—N2 | −177.8 (3) |
O1—C5—C4—N1 | 2.7 (4) |
C11H9BrN2O | Dx = 1.696 Mg m−3 |
Mr = 265.10 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 2524 reflections |
a = 10.1389 (7) Å | θ = 3.4–28.1° |
b = 7.5691 (5) Å | µ = 3.93 mm−1 |
c = 27.0498 (15) Å | T = 293 K |
V = 2075.9 (2) Å3 | Needle-like, colourless |
Z = 8 | 0.40 × 0.08 × 0.05 mm |
F(000) = 1056 |
Xcalibur, Ruby, Gemini ultra diffractometer | 1826 independent reflections |
Radiation source: fine-focus sealed tube | 1505 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
Detector resolution: 10.3712 pixels mm-1 | θmax = 25.0°, θmin = 3.4° |
ω scans | h = −9→12 |
Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | k = −7→9 |
Tmin = 0.692, Tmax = 0.822 | l = −29→32 |
7194 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.032 | H-atom parameters constrained |
wR(F2) = 0.076 | w = 1/[σ2(Fo2) + (0.0367P)2 + 0.6352P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
1821 reflections | Δρmax = 0.43 e Å−3 |
137 parameters | Δρmin = −0.27 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0030 (3) |
C11H9BrN2O | V = 2075.9 (2) Å3 |
Mr = 265.10 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 10.1389 (7) Å | µ = 3.93 mm−1 |
b = 7.5691 (5) Å | T = 293 K |
c = 27.0498 (15) Å | 0.40 × 0.08 × 0.05 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 1826 independent reflections |
Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | 1505 reflections with I > 2σ(I) |
Tmin = 0.692, Tmax = 0.822 | Rint = 0.034 |
7194 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | 0 restraints |
wR(F2) = 0.076 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.43 e Å−3 |
1821 reflections | Δρmin = −0.27 e Å−3 |
137 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.9710 (3) | 0.3077 (4) | 0.53886 (10) | 0.0416 (7) | |
H1 | 1.0442 | 0.3774 | 0.5319 | 0.050* | |
C2 | 0.8099 (3) | 0.1211 (3) | 0.52966 (10) | 0.0394 (7) | |
H2 | 0.7503 | 0.0401 | 0.5166 | 0.047* | |
C3 | 0.8128 (3) | 0.1835 (4) | 0.57615 (10) | 0.0445 (7) | |
H3 | 0.7544 | 0.1506 | 0.6010 | 0.053* | |
C4 | 0.9478 (3) | 0.1782 (4) | 0.45398 (9) | 0.0357 (6) | |
H4A | 0.9439 | 0.0535 | 0.4459 | 0.043* | |
H4B | 1.0381 | 0.2172 | 0.4492 | 0.043* | |
C5 | 0.8589 (3) | 0.2791 (3) | 0.41889 (9) | 0.0324 (6) | |
C6 | 0.8756 (2) | 0.2468 (3) | 0.36502 (9) | 0.0305 (6) | |
C7 | 0.7789 (3) | 0.3063 (4) | 0.33305 (10) | 0.0395 (7) | |
H7 | 0.7066 | 0.3674 | 0.3455 | 0.047* | |
C8 | 0.7887 (3) | 0.2760 (4) | 0.28289 (10) | 0.0411 (7) | |
H8 | 0.7230 | 0.3159 | 0.2616 | 0.049* | |
C9 | 0.8958 (3) | 0.1869 (3) | 0.26456 (9) | 0.0357 (6) | |
C10 | 0.9941 (3) | 0.1265 (3) | 0.29573 (10) | 0.0386 (7) | |
H10 | 1.0666 | 0.0667 | 0.2830 | 0.046* | |
C11 | 0.9835 (3) | 0.1559 (3) | 0.34578 (10) | 0.0355 (6) | |
H11 | 1.0490 | 0.1148 | 0.3669 | 0.043* | |
N1 | 0.9126 (2) | 0.2011 (3) | 0.50543 (8) | 0.0339 (5) | |
N2 | 0.9137 (2) | 0.3022 (4) | 0.58199 (9) | 0.0495 (7) | |
O1 | 0.7774 (2) | 0.3806 (3) | 0.43462 (7) | 0.0522 (6) | |
Br1 | 0.90954 (3) | 0.14638 (4) | 0.195554 (10) | 0.04969 (16) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0430 (17) | 0.0470 (16) | 0.0347 (16) | −0.0041 (13) | −0.0094 (14) | 0.0014 (13) |
C2 | 0.0307 (15) | 0.0510 (16) | 0.0366 (15) | 0.0001 (12) | 0.0001 (12) | 0.0029 (13) |
C3 | 0.0418 (18) | 0.0593 (18) | 0.0323 (15) | 0.0071 (15) | 0.0028 (13) | 0.0046 (14) |
C4 | 0.0362 (15) | 0.0452 (15) | 0.0257 (13) | 0.0047 (12) | 0.0001 (12) | −0.0009 (11) |
C5 | 0.0313 (14) | 0.0363 (14) | 0.0297 (14) | −0.0001 (12) | −0.0006 (12) | −0.0031 (12) |
C6 | 0.0347 (15) | 0.0301 (13) | 0.0267 (13) | 0.0027 (11) | −0.0026 (11) | −0.0004 (11) |
C7 | 0.0437 (18) | 0.0421 (14) | 0.0326 (14) | 0.0133 (13) | −0.0038 (13) | −0.0061 (12) |
C8 | 0.0469 (18) | 0.0441 (15) | 0.0322 (14) | 0.0095 (13) | −0.0090 (13) | −0.0028 (13) |
C9 | 0.0481 (17) | 0.0367 (14) | 0.0222 (13) | −0.0033 (13) | 0.0019 (12) | −0.0021 (11) |
C10 | 0.0385 (16) | 0.0424 (15) | 0.0348 (15) | 0.0043 (12) | 0.0062 (13) | −0.0010 (12) |
C11 | 0.0330 (15) | 0.0415 (15) | 0.0320 (14) | 0.0049 (12) | −0.0033 (12) | 0.0031 (11) |
N1 | 0.0335 (13) | 0.0434 (12) | 0.0248 (11) | 0.0013 (10) | −0.0021 (9) | −0.0013 (10) |
N2 | 0.0588 (17) | 0.0623 (16) | 0.0274 (13) | 0.0016 (13) | −0.0053 (12) | −0.0052 (12) |
O1 | 0.0575 (14) | 0.0650 (13) | 0.0342 (11) | 0.0278 (11) | −0.0027 (10) | −0.0088 (9) |
Br1 | 0.0671 (3) | 0.0558 (2) | 0.0262 (2) | 0.00046 (15) | 0.00192 (13) | −0.00478 (12) |
C1—N2 | 1.304 (4) | C5—C6 | 1.487 (3) |
C1—N1 | 1.349 (3) | C6—C7 | 1.382 (3) |
C1—H1 | 0.9300 | C6—C11 | 1.394 (4) |
C2—C3 | 1.344 (4) | C7—C8 | 1.379 (4) |
C2—N1 | 1.372 (3) | C7—H7 | 0.9300 |
C2—H2 | 0.9300 | C8—C9 | 1.372 (4) |
C3—N2 | 1.371 (4) | C8—H8 | 0.9300 |
C3—H3 | 0.9300 | C9—C10 | 1.382 (4) |
C4—N1 | 1.447 (3) | C9—Br1 | 1.897 (3) |
C4—C5 | 1.516 (4) | C10—C11 | 1.376 (4) |
C4—H4A | 0.9700 | C10—H10 | 0.9300 |
C4—H4B | 0.9700 | C11—H11 | 0.9300 |
C5—O1 | 1.205 (3) | ||
N2—C1—N1 | 112.7 (3) | C11—C6—C5 | 122.4 (2) |
N2—C1—H1 | 123.7 | C8—C7—C6 | 120.7 (2) |
N1—C1—H1 | 123.7 | C8—C7—H7 | 119.7 |
C3—C2—N1 | 106.0 (3) | C6—C7—H7 | 119.7 |
C3—C2—H2 | 127.0 | C9—C8—C7 | 119.6 (2) |
N1—C2—H2 | 127.0 | C9—C8—H8 | 120.2 |
C2—C3—N2 | 110.8 (3) | C7—C8—H8 | 120.2 |
C2—C3—H3 | 124.6 | C8—C9—C10 | 120.8 (2) |
N2—C3—H3 | 124.6 | C8—C9—Br1 | 119.5 (2) |
N1—C4—C5 | 113.3 (2) | C10—C9—Br1 | 119.6 (2) |
N1—C4—H4A | 108.9 | C11—C10—C9 | 119.4 (3) |
C5—C4—H4A | 108.9 | C11—C10—H10 | 120.3 |
N1—C4—H4B | 108.9 | C9—C10—H10 | 120.3 |
C5—C4—H4B | 108.9 | C10—C11—C6 | 120.5 (2) |
H4A—C4—H4B | 107.7 | C10—C11—H11 | 119.7 |
O1—C5—C6 | 121.9 (2) | C6—C11—H11 | 119.7 |
O1—C5—C4 | 120.5 (2) | C1—N1—C2 | 106.1 (2) |
C6—C5—C4 | 117.6 (2) | C1—N1—C4 | 127.5 (2) |
C7—C6—C11 | 119.0 (2) | C2—N1—C4 | 126.4 (2) |
C7—C6—C5 | 118.6 (2) | C1—N2—C3 | 104.5 (2) |
N1—C2—C3—N2 | 0.6 (3) | Br1—C9—C10—C11 | −179.86 (19) |
N1—C4—C5—O1 | 7.1 (4) | C9—C10—C11—C6 | −0.5 (4) |
N1—C4—C5—C6 | −172.4 (2) | C7—C6—C11—C10 | 0.3 (4) |
O1—C5—C6—C7 | −13.2 (4) | C5—C6—C11—C10 | 179.0 (2) |
C4—C5—C6—C7 | 166.3 (2) | N2—C1—N1—C2 | −0.2 (3) |
O1—C5—C6—C11 | 168.0 (3) | N2—C1—N1—C4 | 178.2 (2) |
C4—C5—C6—C11 | −12.4 (4) | C3—C2—N1—C1 | −0.2 (3) |
C11—C6—C7—C8 | 0.2 (4) | C3—C2—N1—C4 | −178.7 (2) |
C5—C6—C7—C8 | −178.6 (2) | C5—C4—N1—C1 | −101.0 (3) |
C6—C7—C8—C9 | −0.4 (4) | C5—C4—N1—C2 | 77.1 (3) |
C7—C8—C9—C10 | 0.2 (4) | N1—C1—N2—C3 | 0.6 (3) |
C7—C8—C9—Br1 | −179.7 (2) | C2—C3—N2—C1 | −0.7 (3) |
C8—C9—C10—C11 | 0.3 (4) |
C11H10BrN2O·Cl·H2O | Z = 2 |
Mr = 319.58 | F(000) = 320 |
Triclinic, P1 | Dx = 1.636 Mg m−3 |
a = 6.845 (5) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 7.141 (5) Å | Cell parameters from 1215 reflections |
c = 13.905 (5) Å | θ = 3.2–65.8° |
α = 101.723 (5)° | µ = 6.16 mm−1 |
β = 95.164 (5)° | T = 293 K |
γ = 100.511 (5)° | Needle-like, colourless |
V = 648.6 (7) Å3 | 0.40 × 0.25 × 0.10 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 2355 independent reflections |
Radiation source: fine-focus sealed tube | 1749 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
Detector resolution: 10.3712 pixels mm-1 | θmax = 67.7°, θmin = 3.3° |
ω scans | h = −8→4 |
Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | k = −8→8 |
Tmin = 0.197, Tmax = 0.543 | l = −16→16 |
2920 measured reflections |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0626P)2] where P = (Fo2 + 2Fc2)/3 |
2143 reflections | (Δ/σ)max = 0.001 |
166 parameters | Δρmax = 0.50 e Å−3 |
0 restraints | Δρmin = −0.52 e Å−3 |
C11H10BrN2O·Cl·H2O | γ = 100.511 (5)° |
Mr = 319.58 | V = 648.6 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.845 (5) Å | Cu Kα radiation |
b = 7.141 (5) Å | µ = 6.16 mm−1 |
c = 13.905 (5) Å | T = 293 K |
α = 101.723 (5)° | 0.40 × 0.25 × 0.10 mm |
β = 95.164 (5)° |
Xcalibur, Ruby, Gemini ultra diffractometer | 2355 independent reflections |
Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | 1749 reflections with I > 2σ(I) |
Tmin = 0.197, Tmax = 0.543 | Rint = 0.039 |
2920 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.121 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.50 e Å−3 |
2143 reflections | Δρmin = −0.52 e Å−3 |
166 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C9 | 0.2121 (7) | 0.2946 (7) | 0.4204 (3) | 0.0346 (10) | |
C8 | 0.2076 (7) | 0.0957 (7) | 0.4009 (3) | 0.0329 (10) | |
H8 | 0.1799 | 0.0214 | 0.3362 | 0.039* | |
C7 | 0.2446 (6) | 0.0103 (7) | 0.4782 (3) | 0.0321 (10) | |
H7 | 0.2435 | −0.1229 | 0.4654 | 0.039* | |
C6 | 0.2840 (6) | 0.1182 (6) | 0.5762 (3) | 0.0305 (10) | |
C11 | 0.2854 (7) | 0.3166 (7) | 0.5947 (3) | 0.0357 (11) | |
H11 | 0.3104 | 0.3902 | 0.6595 | 0.043* | |
C10 | 0.2496 (7) | 0.4060 (7) | 0.5170 (3) | 0.0399 (11) | |
H10 | 0.2508 | 0.5392 | 0.5294 | 0.048* | |
C5 | 0.3216 (6) | 0.0156 (7) | 0.6566 (3) | 0.0312 (10) | |
C4 | 0.3774 (7) | 0.1366 (7) | 0.7623 (3) | 0.0339 (10) | |
H4A | 0.5076 | 0.2222 | 0.7688 | 0.041* | |
H4B | 0.2796 | 0.2169 | 0.7780 | 0.041* | |
C2 | 0.2223 (7) | −0.0738 (7) | 0.8726 (3) | 0.0375 (11) | |
H2 | 0.0959 | −0.0430 | 0.8692 | 0.045* | |
C3 | 0.2821 (7) | −0.2050 (7) | 0.9191 (4) | 0.0431 (12) | |
H3 | 0.2059 | −0.2809 | 0.9548 | 0.052* | |
C1 | 0.5354 (7) | −0.0781 (7) | 0.8505 (3) | 0.0400 (12) | |
H1 | 0.6612 | −0.0519 | 0.8300 | 0.048* | |
N1 | 0.3829 (5) | 0.0068 (5) | 0.8309 (3) | 0.0322 (8) | |
N2 | 0.4772 (6) | −0.2056 (6) | 0.9040 (3) | 0.0392 (10) | |
O1 | 0.3131 (5) | −0.1593 (5) | 0.6410 (2) | 0.0425 (8) | |
O2 | 0.2485 (7) | 0.3911 (8) | 1.0329 (4) | 0.0662 (14) | |
Br1 | 0.16581 (8) | 0.42138 (8) | 0.31623 (3) | 0.0433 (2) | |
Cl1 | −0.06891 (17) | 0.28466 (17) | 0.84308 (8) | 0.0382 (3) | |
H2N | 0.556 (8) | −0.292 (7) | 0.928 (4) | 0.048 (15)* | |
H2O | 0.201 (9) | 0.444 (10) | 1.069 (5) | 0.06 (2)* | |
H2P | 0.166 (9) | 0.351 (9) | 0.980 (5) | 0.062 (19)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C9 | 0.038 (3) | 0.038 (3) | 0.030 (2) | 0.011 (2) | −0.0003 (19) | 0.012 (2) |
C8 | 0.036 (2) | 0.033 (3) | 0.029 (2) | 0.010 (2) | 0.0012 (18) | 0.0036 (19) |
C7 | 0.032 (2) | 0.031 (3) | 0.033 (2) | 0.0103 (19) | 0.0028 (19) | 0.0033 (19) |
C6 | 0.024 (2) | 0.032 (3) | 0.036 (2) | 0.0070 (18) | 0.0009 (18) | 0.0092 (19) |
C11 | 0.050 (3) | 0.030 (3) | 0.025 (2) | 0.010 (2) | −0.002 (2) | 0.0046 (19) |
C10 | 0.057 (3) | 0.029 (3) | 0.032 (2) | 0.012 (2) | −0.003 (2) | 0.0030 (19) |
C5 | 0.031 (2) | 0.031 (3) | 0.034 (2) | 0.0106 (19) | 0.0034 (19) | 0.0080 (19) |
C4 | 0.040 (3) | 0.031 (2) | 0.033 (2) | 0.010 (2) | 0.000 (2) | 0.0130 (19) |
C2 | 0.037 (3) | 0.040 (3) | 0.042 (3) | 0.012 (2) | 0.004 (2) | 0.019 (2) |
C3 | 0.041 (3) | 0.045 (3) | 0.047 (3) | 0.011 (2) | 0.005 (2) | 0.018 (2) |
C1 | 0.039 (3) | 0.048 (3) | 0.040 (3) | 0.018 (2) | 0.004 (2) | 0.017 (2) |
N1 | 0.036 (2) | 0.032 (2) | 0.0314 (19) | 0.0129 (17) | 0.0001 (16) | 0.0101 (16) |
N2 | 0.049 (2) | 0.036 (2) | 0.037 (2) | 0.0194 (19) | −0.0021 (19) | 0.0107 (18) |
O1 | 0.058 (2) | 0.0320 (19) | 0.0372 (18) | 0.0118 (16) | 0.0008 (16) | 0.0080 (14) |
O2 | 0.072 (3) | 0.084 (4) | 0.046 (2) | 0.055 (3) | −0.011 (2) | −0.005 (2) |
Br1 | 0.0547 (4) | 0.0453 (4) | 0.0335 (3) | 0.0137 (2) | −0.0003 (2) | 0.0165 (2) |
Cl1 | 0.0453 (7) | 0.0380 (7) | 0.0351 (6) | 0.0183 (5) | 0.0016 (5) | 0.0099 (5) |
C9—C8 | 1.385 (6) | C4—N1 | 1.461 (5) |
C9—C10 | 1.390 (7) | C4—H4A | 0.9700 |
C9—Br1 | 1.890 (4) | C4—H4B | 0.9700 |
C8—C7 | 1.367 (6) | C2—C3 | 1.343 (7) |
C8—H8 | 0.9300 | C2—N1 | 1.377 (6) |
C7—C6 | 1.397 (6) | C2—H2 | 0.9300 |
C7—H7 | 0.9300 | C3—N2 | 1.371 (6) |
C6—C11 | 1.386 (6) | C3—H3 | 0.9300 |
C6—C5 | 1.485 (6) | C1—N2 | 1.318 (6) |
C11—C10 | 1.388 (6) | C1—N1 | 1.334 (6) |
C11—H11 | 0.9300 | C1—H1 | 0.9300 |
C10—H10 | 0.9300 | N2—H2N | 0.98 (5) |
C5—O1 | 1.213 (5) | O2—H2O | 0.70 (6) |
C5—C4 | 1.521 (6) | O2—H2P | 0.85 (6) |
C8—C9—C10 | 120.9 (4) | N1—C4—H4A | 109.8 |
C8—C9—Br1 | 120.8 (3) | C5—C4—H4A | 109.8 |
C10—C9—Br1 | 118.3 (4) | N1—C4—H4B | 109.8 |
C7—C8—C9 | 118.9 (4) | C5—C4—H4B | 109.8 |
C7—C8—H8 | 120.5 | H4A—C4—H4B | 108.2 |
C9—C8—H8 | 120.5 | C3—C2—N1 | 107.2 (4) |
C8—C7—C6 | 121.6 (4) | C3—C2—H2 | 126.4 |
C8—C7—H7 | 119.2 | N1—C2—H2 | 126.4 |
C6—C7—H7 | 119.2 | C2—C3—N2 | 106.8 (4) |
C11—C6—C7 | 118.8 (4) | C2—C3—H3 | 126.6 |
C11—C6—C5 | 122.4 (4) | N2—C3—H3 | 126.6 |
C7—C6—C5 | 118.7 (4) | N2—C1—N1 | 108.2 (4) |
C10—C11—C6 | 120.3 (4) | N2—C1—H1 | 125.9 |
C10—C11—H11 | 119.8 | N1—C1—H1 | 125.9 |
C6—C11—H11 | 119.8 | C1—N1—C2 | 108.3 (4) |
C11—C10—C9 | 119.4 (4) | C1—N1—C4 | 125.1 (4) |
C11—C10—H10 | 120.3 | C2—N1—C4 | 125.8 (4) |
C9—C10—H10 | 120.3 | C1—N2—C3 | 109.4 (4) |
O1—C5—C6 | 122.6 (4) | C1—N2—H2N | 127 (3) |
O1—C5—C4 | 119.1 (4) | C3—N2—H2N | 124 (3) |
C6—C5—C4 | 118.3 (4) | H2O—O2—H2P | 107 (7) |
N1—C4—C5 | 109.6 (4) | ||
C10—C9—C8—C7 | −1.2 (7) | C7—C6—C5—C4 | 176.2 (4) |
Br1—C9—C8—C7 | 179.1 (3) | O1—C5—C4—N1 | −8.4 (6) |
C9—C8—C7—C6 | 0.8 (7) | C6—C5—C4—N1 | 172.9 (3) |
C8—C7—C6—C11 | 0.0 (7) | N1—C2—C3—N2 | −1.0 (6) |
C8—C7—C6—C5 | 179.6 (4) | N2—C1—N1—C2 | −1.0 (6) |
C7—C6—C11—C10 | −0.5 (7) | N2—C1—N1—C4 | −171.1 (4) |
C5—C6—C11—C10 | 179.9 (4) | C3—C2—N1—C1 | 1.2 (6) |
C6—C11—C10—C9 | 0.1 (7) | C3—C2—N1—C4 | 171.3 (4) |
C8—C9—C10—C11 | 0.8 (8) | C5—C4—N1—C1 | 80.7 (6) |
Br1—C9—C10—C11 | −179.6 (4) | C5—C4—N1—C2 | −87.7 (5) |
C11—C6—C5—O1 | 177.1 (4) | N1—C1—N2—C3 | 0.4 (6) |
C7—C6—C5—O1 | −2.5 (6) | C2—C3—N2—C1 | 0.4 (6) |
C11—C6—C5—C4 | −4.2 (6) |
C11H9N3O3·3(H2O) | Z = 2 |
Mr = 285.26 | F(000) = 300 |
Triclinic, P1 | Dx = 1.405 Mg m−3 |
a = 7.0408 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.4596 (5) Å | Cell parameters from 3247 reflections |
c = 11.4455 (7) Å | θ = 3.5–27.0° |
α = 89.438 (5)° | µ = 0.12 mm−1 |
β = 86.904 (4)° | T = 293 K |
γ = 82.072 (4)° | Needle-like, colourless |
V = 674.22 (6) Å3 | 0.45 × 0.32 × 0.10 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 2860 independent reflections |
Radiation source: fine-focus sealed tube | 2238 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 10.3712 pixels mm-1 | θmax = 28.1°, θmin = 3.3° |
ω scans | h = −9→9 |
Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | k = −11→10 |
Tmin = 0.809, Tmax = 1.000 | l = −15→14 |
9754 measured reflections |
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: inferred from neighbouring sites |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0525P)2 + 0.1757P] where P = (Fo2 + 2Fc2)/3 |
2860 reflections | (Δ/σ)max < 0.001 |
181 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
C11H9N3O3·3(H2O) | γ = 82.072 (4)° |
Mr = 285.26 | V = 674.22 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.0408 (3) Å | Mo Kα radiation |
b = 8.4596 (5) Å | µ = 0.12 mm−1 |
c = 11.4455 (7) Å | T = 293 K |
α = 89.438 (5)° | 0.45 × 0.32 × 0.10 mm |
β = 86.904 (4)° |
Xcalibur, Ruby, Gemini ultra diffractometer | 2860 independent reflections |
Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | 2238 reflections with I > 2σ(I) |
Tmin = 0.809, Tmax = 1.000 | Rint = 0.025 |
9754 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.15 e Å−3 |
2860 reflections | Δρmin = −0.28 e Å−3 |
181 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.46324 (19) | 0.57267 (17) | 0.65054 (12) | 0.0414 (4) | |
N2 | 0.2276 (2) | 0.4374 (2) | 0.61396 (15) | 0.0563 (4) | |
N3 | 1.2329 (2) | 0.81633 (18) | 1.07608 (14) | 0.0454 (4) | |
O1 | 0.47025 (16) | 0.60934 (15) | 0.88362 (11) | 0.0485 (3) | |
O2 | 1.2617 (2) | 0.7520 (2) | 1.17057 (13) | 0.0706 (5) | |
O3 | 1.33078 (19) | 0.91217 (17) | 1.03256 (13) | 0.0591 (4) | |
C1 | 0.3947 (3) | 0.4327 (2) | 0.65951 (17) | 0.0526 (5) | |
H1 | 0.4588 | 0.3423 | 0.6943 | 0.063* | |
C3 | 0.1868 (3) | 0.5896 (2) | 0.57362 (17) | 0.0537 (5) | |
H3 | 0.0761 | 0.6294 | 0.5362 | 0.064* | |
C2 | 0.3289 (3) | 0.6744 (2) | 0.59545 (17) | 0.0515 (5) | |
H2 | 0.3346 | 0.7810 | 0.5768 | 0.062* | |
C4 | 0.6381 (2) | 0.6111 (2) | 0.69843 (15) | 0.0424 (4) | |
H4A | 0.6730 | 0.7074 | 0.6613 | 0.051* | |
H4B | 0.7417 | 0.5251 | 0.6811 | 0.051* | |
C5 | 0.6144 (2) | 0.63593 (19) | 0.82961 (14) | 0.0358 (4) | |
C6 | 0.7773 (2) | 0.68798 (18) | 0.89114 (14) | 0.0338 (4) | |
C7 | 0.7817 (2) | 0.6637 (2) | 1.01146 (15) | 0.0406 (4) | |
H7 | 0.6829 | 0.6193 | 1.0511 | 0.049* | |
C8 | 0.9308 (2) | 0.7049 (2) | 1.07242 (15) | 0.0424 (4) | |
H8 | 0.9362 | 0.6863 | 1.1525 | 0.051* | |
C9 | 1.0720 (2) | 0.77451 (19) | 1.01137 (15) | 0.0371 (4) | |
C10 | 1.0712 (2) | 0.8032 (2) | 0.89326 (15) | 0.0414 (4) | |
H10 | 1.1675 | 0.8522 | 0.8550 | 0.050* | |
C11 | 0.9229 (2) | 0.7571 (2) | 0.83234 (15) | 0.0406 (4) | |
H11 | 0.9210 | 0.7726 | 0.7518 | 0.049* | |
O99 | 0.1349 (2) | 0.12450 (17) | 0.62347 (13) | 0.0642 (4) | |
O98 | 0.4506 (2) | −0.00097 (18) | 0.75108 (12) | 0.0637 (4) | |
O97 | 0.2217 (2) | 0.0003 (2) | 0.39699 (13) | 0.0722 (5) | |
H99A | 0.1543 | 0.2299 | 0.6204 | 0.050* | |
H97A | 0.4667 | 0.0315 | 0.8314 | 0.050* | |
H98B | 0.1248 | −0.0565 | 0.3864 | 0.050* | |
H97B | 0.5662 | 0.0090 | 0.7015 | 0.050* | |
H98A | 0.1948 | 0.0377 | 0.4793 | 0.050* | |
H99B | 0.2425 | 0.0856 | 0.6676 | 0.050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0397 (7) | 0.0469 (8) | 0.0407 (8) | −0.0126 (6) | −0.0110 (6) | −0.0026 (6) |
N2 | 0.0515 (9) | 0.0647 (11) | 0.0585 (10) | −0.0221 (8) | −0.0183 (8) | −0.0040 (8) |
N3 | 0.0367 (8) | 0.0479 (9) | 0.0531 (9) | −0.0068 (7) | −0.0099 (7) | −0.0106 (7) |
O1 | 0.0378 (6) | 0.0623 (8) | 0.0492 (7) | −0.0205 (6) | −0.0024 (5) | 0.0014 (6) |
O2 | 0.0667 (9) | 0.0919 (12) | 0.0602 (9) | −0.0248 (8) | −0.0329 (7) | 0.0109 (8) |
O3 | 0.0504 (8) | 0.0624 (9) | 0.0709 (9) | −0.0267 (7) | −0.0123 (7) | −0.0072 (7) |
C1 | 0.0548 (11) | 0.0473 (11) | 0.0608 (12) | −0.0178 (9) | −0.0208 (9) | 0.0036 (9) |
C3 | 0.0460 (10) | 0.0633 (13) | 0.0526 (11) | −0.0033 (9) | −0.0194 (9) | −0.0086 (9) |
C2 | 0.0560 (11) | 0.0462 (11) | 0.0535 (11) | −0.0056 (9) | −0.0189 (9) | −0.0017 (9) |
C4 | 0.0374 (8) | 0.0508 (10) | 0.0422 (10) | −0.0155 (8) | −0.0067 (7) | −0.0037 (8) |
C5 | 0.0328 (8) | 0.0340 (8) | 0.0421 (9) | −0.0091 (7) | −0.0047 (7) | 0.0017 (7) |
C6 | 0.0301 (8) | 0.0339 (8) | 0.0381 (9) | −0.0057 (6) | −0.0041 (6) | −0.0022 (7) |
C7 | 0.0377 (9) | 0.0461 (10) | 0.0402 (9) | −0.0143 (7) | 0.0001 (7) | 0.0005 (7) |
C8 | 0.0437 (9) | 0.0494 (10) | 0.0355 (9) | −0.0101 (8) | −0.0057 (7) | −0.0021 (7) |
C9 | 0.0302 (8) | 0.0364 (9) | 0.0454 (10) | −0.0048 (7) | −0.0079 (7) | −0.0067 (7) |
C10 | 0.0340 (8) | 0.0475 (10) | 0.0455 (10) | −0.0146 (7) | −0.0029 (7) | 0.0031 (8) |
C11 | 0.0369 (8) | 0.0509 (10) | 0.0362 (9) | −0.0126 (7) | −0.0047 (7) | 0.0026 (7) |
O99 | 0.0636 (9) | 0.0654 (9) | 0.0702 (10) | −0.0253 (7) | −0.0200 (7) | −0.0047 (7) |
O98 | 0.0592 (8) | 0.0769 (10) | 0.0603 (9) | −0.0240 (7) | −0.0123 (7) | −0.0083 (7) |
O97 | 0.0731 (10) | 0.0947 (12) | 0.0566 (9) | −0.0379 (9) | −0.0064 (7) | 0.0001 (8) |
N1—C1 | 1.340 (2) | C6—C11 | 1.389 (2) |
N1—C2 | 1.365 (2) | C6—C7 | 1.392 (2) |
N1—C4 | 1.452 (2) | C7—C8 | 1.377 (2) |
N2—C1 | 1.308 (2) | C7—H7 | 0.9300 |
N2—C3 | 1.362 (3) | C8—C9 | 1.378 (2) |
N3—O2 | 1.220 (2) | C8—H8 | 0.9300 |
N3—O3 | 1.2206 (19) | C9—C10 | 1.371 (2) |
N3—C9 | 1.471 (2) | C10—C11 | 1.387 (2) |
O1—C5 | 1.2066 (19) | C10—H10 | 0.9300 |
C1—H1 | 0.9300 | C11—H11 | 0.9300 |
C3—C2 | 1.344 (3) | O99—H99A | 0.9205 |
C3—H3 | 0.9300 | O99—H99B | 0.9522 |
C2—H2 | 0.9300 | O98—H97A | 0.9789 |
C4—C5 | 1.515 (2) | O98—H97B | 0.9798 |
C4—H4A | 0.9700 | O97—H98B | 0.9014 |
C4—H4B | 0.9700 | O97—H98A | 0.9967 |
C5—C6 | 1.496 (2) | ||
C1—N1—C2 | 106.24 (15) | O1—C5—C4 | 120.80 (14) |
C1—N1—C4 | 126.56 (15) | C6—C5—C4 | 118.35 (13) |
C2—N1—C4 | 127.03 (15) | C11—C6—C7 | 119.68 (14) |
C1—N2—C3 | 104.60 (15) | C11—C6—C5 | 122.38 (14) |
O2—N3—O3 | 123.52 (14) | C7—C6—C5 | 117.94 (14) |
O2—N3—C9 | 117.83 (15) | C8—C7—C6 | 120.62 (15) |
O3—N3—C9 | 118.64 (15) | C8—C7—H7 | 119.7 |
N2—C1—N1 | 112.50 (17) | C6—C7—H7 | 119.7 |
N2—C1—H1 | 123.8 | C7—C8—C9 | 118.09 (15) |
N1—C1—H1 | 123.8 | C7—C8—H8 | 121.0 |
C2—C3—N2 | 110.52 (16) | C9—C8—H8 | 121.0 |
C2—C3—H3 | 124.7 | C10—C9—C8 | 123.15 (14) |
N2—C3—H3 | 124.7 | C10—C9—N3 | 118.71 (14) |
C3—C2—N1 | 106.15 (17) | C8—C9—N3 | 118.12 (15) |
C3—C2—H2 | 126.9 | C9—C10—C11 | 118.18 (15) |
N1—C2—H2 | 126.9 | C9—C10—H10 | 120.9 |
N1—C4—C5 | 111.73 (14) | C11—C10—H10 | 120.9 |
N1—C4—H4A | 109.3 | C10—C11—C6 | 120.25 (15) |
C5—C4—H4A | 109.3 | C10—C11—H11 | 119.9 |
N1—C4—H4B | 109.3 | C6—C11—H11 | 119.9 |
C5—C4—H4B | 109.3 | H99A—O99—H99B | 97.5 |
H4A—C4—H4B | 107.9 | H97A—O98—H97B | 110.6 |
O1—C5—C6 | 120.81 (15) | H98B—O97—H98A | 102.3 |
C3—N2—C1—N1 | −0.1 (2) | C11—C6—C7—C8 | −1.2 (3) |
C2—N1—C1—N2 | 0.3 (2) | C5—C6—C7—C8 | 178.12 (15) |
C4—N1—C1—N2 | 175.80 (16) | C6—C7—C8—C9 | 1.7 (3) |
C1—N2—C3—C2 | −0.1 (2) | C7—C8—C9—C10 | −0.5 (3) |
N2—C3—C2—N1 | 0.3 (2) | C7—C8—C9—N3 | −179.09 (15) |
C1—N1—C2—C3 | −0.3 (2) | O2—N3—C9—C10 | −159.83 (17) |
C4—N1—C2—C3 | −175.82 (17) | O3—N3—C9—C10 | 19.7 (2) |
C1—N1—C4—C5 | −75.1 (2) | O2—N3—C9—C8 | 18.8 (2) |
C2—N1—C4—C5 | 99.5 (2) | O3—N3—C9—C8 | −161.64 (16) |
N1—C4—C5—O1 | 6.7 (2) | C8—C9—C10—C11 | −1.2 (3) |
N1—C4—C5—C6 | −175.66 (13) | N3—C9—C10—C11 | 177.34 (15) |
O1—C5—C6—C11 | −163.62 (16) | C9—C10—C11—C6 | 1.8 (3) |
C4—C5—C6—C11 | 18.8 (2) | C7—C6—C11—C10 | −0.6 (3) |
O1—C5—C6—C7 | 17.1 (2) | C5—C6—C11—C10 | −179.88 (15) |
C4—C5—C6—C7 | −160.55 (15) |
C11H12N3O3·Cl | F(000) = 1120 |
Mr = 269.69 | Dx = 1.431 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 21.9100 (7) Å | Cell parameters from 10843 reflections |
b = 8.0131 (3) Å | θ = 3.3–29.3° |
c = 14.3802 (4) Å | µ = 0.31 mm−1 |
β = 97.325 (3)° | T = 293 K |
V = 2504.09 (14) Å3 | Prim, colourless |
Z = 8 | 0.30 × 0.20 × 0.10 mm |
Xcalibur, Ruby, Gemini ultra diffractometer | 4428 independent reflections |
Radiation source: fine-focus sealed tube | 3979 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
Detector resolution: 10.3712 pixels mm-1 | θmax = 25.0°, θmin = 3.4° |
ω scans | h = −26→25 |
Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | k = −9→9 |
Tmin = 0.929, Tmax = 0.970 | l = −16→17 |
20723 measured reflections |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.093 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0364P)2 + 1.190P] where P = (Fo2 + 2Fc2)/3 |
4418 reflections | (Δ/σ)max < 0.001 |
341 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C11H12N3O3·Cl | V = 2504.09 (14) Å3 |
Mr = 269.69 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 21.9100 (7) Å | µ = 0.31 mm−1 |
b = 8.0131 (3) Å | T = 293 K |
c = 14.3802 (4) Å | 0.30 × 0.20 × 0.10 mm |
β = 97.325 (3)° |
Xcalibur, Ruby, Gemini ultra diffractometer | 4428 independent reflections |
Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | 3979 reflections with I > 2σ(I) |
Tmin = 0.929, Tmax = 0.970 | Rint = 0.022 |
20723 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.093 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.23 e Å−3 |
4418 reflections | Δρmin = −0.24 e Å−3 |
341 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.39014 (10) | −0.0380 (3) | 0.45781 (14) | 0.0554 (5) | |
H1 | 0.3572 | 0.0327 | 0.4390 | 0.066* | |
C2 | 0.45540 (10) | −0.2009 (2) | 0.54226 (15) | 0.0537 (5) | |
H2 | 0.4749 | −0.2620 | 0.5925 | 0.064* | |
C3 | 0.47310 (10) | −0.1880 (3) | 0.45663 (15) | 0.0573 (5) | |
H3 | 0.5071 | −0.2389 | 0.4361 | 0.069* | |
C4 | 0.36802 (10) | −0.0821 (3) | 0.62132 (14) | 0.0547 (5) | |
H4A | 0.3748 | −0.1763 | 0.6638 | 0.066* | |
H4B | 0.3244 | −0.0772 | 0.5986 | 0.066* | |
C5 | 0.38716 (8) | 0.0777 (2) | 0.67400 (12) | 0.0417 (4) | |
H5 | 0.4318 | 0.0769 | 0.6921 | 0.050* | |
C6 | 0.35520 (8) | 0.0891 (2) | 0.76181 (12) | 0.0403 (4) | |
C7 | 0.37933 (11) | 0.0035 (3) | 0.84130 (15) | 0.0638 (6) | |
H7 | 0.4157 | −0.0565 | 0.8411 | 0.077* | |
C8 | 0.35039 (11) | 0.0053 (3) | 0.92114 (15) | 0.0651 (6) | |
H8 | 0.3666 | −0.0535 | 0.9744 | 0.078* | |
C9 | 0.29737 (9) | 0.0956 (2) | 0.92004 (13) | 0.0474 (5) | |
C10 | 0.27354 (9) | 0.1870 (3) | 0.84388 (14) | 0.0511 (5) | |
H10 | 0.2383 | 0.2510 | 0.8456 | 0.061* | |
C11 | 0.30273 (9) | 0.1828 (3) | 0.76414 (13) | 0.0477 (4) | |
H11 | 0.2868 | 0.2438 | 0.7116 | 0.057* | |
C21 | 0.05533 (9) | 0.5727 (2) | 0.66467 (14) | 0.0492 (5) | |
H21 | 0.0447 | 0.5691 | 0.7252 | 0.059* | |
C22 | 0.09709 (10) | 0.5152 (3) | 0.53917 (14) | 0.0548 (5) | |
H22 | 0.1207 | 0.4639 | 0.4980 | 0.066* | |
C23 | 0.05931 (10) | 0.6451 (3) | 0.52014 (15) | 0.0615 (6) | |
H23 | 0.0518 | 0.7017 | 0.4634 | 0.074* | |
C24 | 0.12577 (8) | 0.3294 (2) | 0.67931 (12) | 0.0423 (4) | |
H24A | 0.1273 | 0.3445 | 0.7465 | 0.051* | |
H24B | 0.1677 | 0.3236 | 0.6646 | 0.051* | |
C25 | 0.09263 (8) | 0.1675 (2) | 0.65045 (12) | 0.0434 (4) | |
H25 | 0.0894 | 0.1553 | 0.5822 | 0.052* | |
C26 | 0.12888 (8) | 0.0227 (2) | 0.69673 (12) | 0.0411 (4) | |
C27 | 0.16951 (9) | −0.0648 (2) | 0.64883 (13) | 0.0480 (5) | |
H27 | 0.1722 | −0.0392 | 0.5864 | 0.058* | |
C28 | 0.20606 (9) | −0.1895 (3) | 0.69241 (14) | 0.0523 (5) | |
H28 | 0.2333 | −0.2484 | 0.6601 | 0.063* | |
C29 | 0.20123 (9) | −0.2242 (2) | 0.78475 (14) | 0.0479 (5) | |
C30 | 0.16019 (10) | −0.1435 (3) | 0.83352 (14) | 0.0549 (5) | |
H30 | 0.1570 | −0.1717 | 0.8954 | 0.066* | |
C31 | 0.12380 (9) | −0.0198 (3) | 0.78898 (13) | 0.0523 (5) | |
H31 | 0.0956 | 0.0358 | 0.8210 | 0.063* | |
N2 | 0.43193 (9) | −0.0867 (2) | 0.40558 (13) | 0.0579 (5) | |
N1 | 0.40301 (7) | −0.1068 (2) | 0.54169 (11) | 0.0479 (4) | |
N3 | 0.26493 (10) | 0.0946 (3) | 1.00319 (13) | 0.0648 (5) | |
N4 | 0.09446 (7) | 0.47182 (19) | 0.63073 (10) | 0.0400 (3) | |
N5 | 0.03384 (8) | 0.6791 (2) | 0.59943 (13) | 0.0534 (4) | |
N6 | 0.24265 (9) | −0.3485 (2) | 0.83428 (16) | 0.0687 (5) | |
O1 | 0.37147 (7) | 0.20963 (18) | 0.61034 (9) | 0.0507 (3) | |
O2 | 0.27864 (10) | −0.0119 (3) | 1.06269 (13) | 0.0946 (6) | |
O3 | 0.22527 (9) | 0.1998 (3) | 1.00893 (13) | 0.0938 (6) | |
O4 | 0.03272 (6) | 0.18148 (19) | 0.67729 (10) | 0.0539 (4) | |
O5 | 0.24127 (9) | −0.3696 (3) | 0.91796 (15) | 0.0950 (6) | |
O6 | 0.27855 (12) | −0.4200 (3) | 0.79039 (16) | 0.1221 (9) | |
Cl1 | −0.06934 (2) | −0.05900 (6) | 0.59702 (3) | 0.04943 (14) | |
Cl2 | 0.45182 (3) | 0.48449 (7) | 0.70812 (4) | 0.06535 (18) | |
H1O | 0.3900 (11) | 0.295 (3) | 0.6344 (17) | 0.070 (8)* | |
H4O | 0.0087 (13) | 0.104 (4) | 0.6494 (19) | 0.089 (9)* | |
H5N | 0.0057 (11) | 0.751 (3) | 0.6048 (16) | 0.066 (7)* | |
H1N | 0.4328 (11) | −0.053 (3) | 0.3500 (19) | 0.074 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0584 (12) | 0.0572 (12) | 0.0503 (11) | −0.0082 (10) | 0.0062 (10) | −0.0071 (10) |
C2 | 0.0614 (13) | 0.0430 (11) | 0.0592 (12) | −0.0035 (10) | 0.0172 (10) | −0.0037 (9) |
C3 | 0.0621 (13) | 0.0513 (12) | 0.0632 (13) | −0.0119 (11) | 0.0258 (11) | −0.0156 (10) |
C4 | 0.0637 (13) | 0.0487 (11) | 0.0569 (12) | −0.0106 (10) | 0.0283 (10) | −0.0072 (9) |
C5 | 0.0427 (10) | 0.0431 (10) | 0.0405 (9) | −0.0015 (8) | 0.0098 (8) | 0.0008 (8) |
C6 | 0.0442 (10) | 0.0374 (9) | 0.0401 (9) | −0.0025 (8) | 0.0083 (7) | 0.0001 (8) |
C7 | 0.0696 (14) | 0.0671 (14) | 0.0581 (13) | 0.0287 (12) | 0.0216 (11) | 0.0187 (11) |
C8 | 0.0798 (15) | 0.0686 (14) | 0.0497 (12) | 0.0176 (13) | 0.0187 (11) | 0.0222 (11) |
C9 | 0.0514 (11) | 0.0511 (11) | 0.0421 (10) | −0.0128 (9) | 0.0155 (8) | −0.0025 (8) |
C10 | 0.0425 (10) | 0.0614 (13) | 0.0504 (11) | 0.0039 (9) | 0.0105 (8) | −0.0020 (9) |
C11 | 0.0465 (10) | 0.0561 (12) | 0.0405 (9) | 0.0055 (9) | 0.0054 (8) | 0.0050 (9) |
C21 | 0.0542 (11) | 0.0501 (11) | 0.0445 (10) | 0.0042 (10) | 0.0109 (9) | −0.0032 (9) |
C22 | 0.0596 (12) | 0.0643 (13) | 0.0438 (10) | 0.0154 (11) | 0.0188 (9) | 0.0152 (9) |
C23 | 0.0673 (14) | 0.0616 (13) | 0.0559 (12) | 0.0114 (11) | 0.0090 (10) | 0.0208 (11) |
C24 | 0.0407 (9) | 0.0506 (11) | 0.0353 (9) | 0.0058 (8) | 0.0040 (7) | 0.0061 (8) |
C25 | 0.0483 (10) | 0.0493 (11) | 0.0322 (8) | 0.0074 (9) | 0.0037 (7) | −0.0010 (8) |
C26 | 0.0433 (10) | 0.0415 (10) | 0.0380 (9) | 0.0008 (8) | 0.0035 (7) | −0.0032 (8) |
C27 | 0.0569 (11) | 0.0495 (11) | 0.0394 (9) | 0.0022 (9) | 0.0124 (8) | −0.0027 (8) |
C28 | 0.0532 (11) | 0.0471 (11) | 0.0583 (12) | 0.0073 (9) | 0.0129 (9) | −0.0106 (9) |
C29 | 0.0493 (11) | 0.0355 (9) | 0.0565 (11) | 0.0030 (8) | −0.0024 (9) | −0.0017 (8) |
C30 | 0.0629 (13) | 0.0607 (13) | 0.0417 (10) | 0.0092 (11) | 0.0086 (9) | 0.0089 (9) |
C31 | 0.0558 (12) | 0.0624 (13) | 0.0406 (10) | 0.0173 (10) | 0.0136 (9) | 0.0036 (9) |
N2 | 0.0707 (12) | 0.0623 (12) | 0.0428 (10) | −0.0188 (10) | 0.0152 (9) | −0.0106 (9) |
N1 | 0.0553 (10) | 0.0420 (9) | 0.0494 (9) | −0.0097 (8) | 0.0181 (7) | −0.0088 (7) |
N3 | 0.0672 (12) | 0.0808 (14) | 0.0500 (10) | −0.0270 (11) | 0.0215 (9) | −0.0065 (10) |
N4 | 0.0407 (8) | 0.0435 (8) | 0.0366 (7) | 0.0038 (7) | 0.0077 (6) | 0.0037 (6) |
N5 | 0.0500 (10) | 0.0429 (9) | 0.0669 (11) | 0.0090 (8) | 0.0057 (8) | −0.0026 (8) |
N6 | 0.0731 (13) | 0.0499 (11) | 0.0786 (14) | 0.0145 (10) | −0.0082 (11) | −0.0017 (10) |
O1 | 0.0662 (9) | 0.0461 (8) | 0.0402 (7) | −0.0043 (7) | 0.0081 (6) | 0.0022 (6) |
O2 | 0.1329 (17) | 0.0959 (14) | 0.0623 (11) | −0.0300 (13) | 0.0411 (11) | 0.0140 (10) |
O3 | 0.0742 (12) | 0.1387 (18) | 0.0768 (12) | 0.0064 (13) | 0.0418 (10) | −0.0079 (12) |
O4 | 0.0428 (7) | 0.0556 (9) | 0.0623 (9) | 0.0022 (7) | 0.0033 (6) | −0.0020 (7) |
O5 | 0.0931 (14) | 0.1020 (15) | 0.0873 (14) | 0.0298 (11) | 0.0020 (11) | 0.0380 (12) |
O6 | 0.153 (2) | 0.1093 (17) | 0.0980 (15) | 0.0890 (17) | −0.0069 (14) | −0.0156 (13) |
Cl1 | 0.0551 (3) | 0.0540 (3) | 0.0388 (2) | 0.0064 (2) | 0.00474 (19) | −0.0020 (2) |
Cl2 | 0.0797 (4) | 0.0661 (4) | 0.0524 (3) | −0.0229 (3) | 0.0167 (3) | −0.0063 (2) |
C1—N2 | 1.315 (3) | C22—N4 | 1.370 (2) |
C1—N1 | 1.323 (3) | C22—H22 | 0.9300 |
C1—H1 | 0.9300 | C23—N5 | 1.359 (3) |
C2—C3 | 1.341 (3) | C23—H23 | 0.9300 |
C2—N1 | 1.372 (3) | C24—N4 | 1.462 (2) |
C2—H2 | 0.9300 | C24—C25 | 1.518 (3) |
C3—N2 | 1.358 (3) | C24—H24A | 0.9700 |
C3—H3 | 0.9300 | C24—H24B | 0.9700 |
C4—N1 | 1.470 (2) | C25—O4 | 1.419 (2) |
C4—C5 | 1.519 (3) | C25—C26 | 1.512 (3) |
C4—H4A | 0.9700 | C25—H25 | 0.9800 |
C4—H4B | 0.9700 | C26—C27 | 1.384 (3) |
C5—O1 | 1.412 (2) | C26—C31 | 1.388 (3) |
C5—C6 | 1.523 (2) | C27—C28 | 1.380 (3) |
C5—H5 | 0.9800 | C27—H27 | 0.9300 |
C6—C11 | 1.377 (3) | C28—C29 | 1.374 (3) |
C6—C7 | 1.380 (3) | C28—H28 | 0.9300 |
C7—C8 | 1.381 (3) | C29—C30 | 1.371 (3) |
C7—H7 | 0.9300 | C29—N6 | 1.469 (3) |
C8—C9 | 1.367 (3) | C30—C31 | 1.378 (3) |
C8—H8 | 0.9300 | C30—H30 | 0.9300 |
C9—C10 | 1.365 (3) | C31—H31 | 0.9300 |
C9—N3 | 1.467 (3) | N2—H1N | 0.85 (3) |
C10—C11 | 1.383 (3) | N3—O2 | 1.219 (3) |
C10—H10 | 0.9300 | N3—O3 | 1.221 (3) |
C11—H11 | 0.9300 | N5—H5N | 0.85 (2) |
C21—N5 | 1.310 (3) | N6—O6 | 1.213 (3) |
C21—N4 | 1.317 (2) | N6—O5 | 1.219 (3) |
C21—H21 | 0.9300 | O1—H1O | 0.84 (3) |
C22—C23 | 1.336 (3) | O4—H4O | 0.87 (3) |
N2—C1—N1 | 108.3 (2) | N4—C24—H24A | 109.5 |
N2—C1—H1 | 125.9 | C25—C24—H24A | 109.5 |
N1—C1—H1 | 125.9 | N4—C24—H24B | 109.5 |
C3—C2—N1 | 107.0 (2) | C25—C24—H24B | 109.5 |
C3—C2—H2 | 126.5 | H24A—C24—H24B | 108.0 |
N1—C2—H2 | 126.5 | O4—C25—C26 | 113.14 (15) |
C2—C3—N2 | 107.0 (2) | O4—C25—C24 | 106.57 (15) |
C2—C3—H3 | 126.5 | C26—C25—C24 | 109.22 (14) |
N2—C3—H3 | 126.5 | O4—C25—H25 | 109.3 |
N1—C4—C5 | 111.31 (15) | C26—C25—H25 | 109.3 |
N1—C4—H4A | 109.4 | C24—C25—H25 | 109.3 |
C5—C4—H4A | 109.4 | C27—C26—C31 | 119.12 (17) |
N1—C4—H4B | 109.4 | C27—C26—C25 | 120.34 (16) |
C5—C4—H4B | 109.4 | C31—C26—C25 | 120.49 (16) |
H4A—C4—H4B | 108.0 | C28—C27—C26 | 120.91 (18) |
O1—C5—C4 | 106.19 (15) | C28—C27—H27 | 119.5 |
O1—C5—C6 | 113.14 (15) | C26—C27—H27 | 119.5 |
C4—C5—C6 | 109.70 (15) | C29—C28—C27 | 118.30 (18) |
O1—C5—H5 | 109.2 | C29—C28—H28 | 120.8 |
C4—C5—H5 | 109.2 | C27—C28—H28 | 120.8 |
C6—C5—H5 | 109.2 | C30—C29—C28 | 122.34 (18) |
C11—C6—C7 | 118.95 (17) | C30—C29—N6 | 118.47 (19) |
C11—C6—C5 | 121.78 (16) | C28—C29—N6 | 119.16 (19) |
C7—C6—C5 | 119.27 (17) | C29—C30—C31 | 118.69 (18) |
C6—C7—C8 | 121.0 (2) | C29—C30—H30 | 120.7 |
C6—C7—H7 | 119.5 | C31—C30—H30 | 120.7 |
C8—C7—H7 | 119.5 | C30—C31—C26 | 120.57 (18) |
C9—C8—C7 | 118.41 (19) | C30—C31—H31 | 119.7 |
C9—C8—H8 | 120.8 | C26—C31—H31 | 119.7 |
C7—C8—H8 | 120.8 | C1—N2—C3 | 109.37 (19) |
C10—C9—C8 | 122.08 (18) | C1—N2—H1N | 123.1 (18) |
C10—C9—N3 | 118.76 (19) | C3—N2—H1N | 127.5 (17) |
C8—C9—N3 | 119.16 (19) | C1—N1—C2 | 108.38 (17) |
C9—C10—C11 | 118.82 (18) | C1—N1—C4 | 125.60 (19) |
C9—C10—H10 | 120.6 | C2—N1—C4 | 126.00 (18) |
C11—C10—H10 | 120.6 | O2—N3—O3 | 123.4 (2) |
C6—C11—C10 | 120.63 (18) | O2—N3—C9 | 118.3 (2) |
C6—C11—H11 | 119.7 | O3—N3—C9 | 118.3 (2) |
C10—C11—H11 | 119.7 | C21—N4—C22 | 108.02 (16) |
N5—C21—N4 | 109.00 (17) | C21—N4—C24 | 126.17 (15) |
N5—C21—H21 | 125.5 | C22—N4—C24 | 125.63 (15) |
N4—C21—H21 | 125.5 | C21—N5—C23 | 108.80 (18) |
C23—C22—N4 | 107.08 (18) | C21—N5—H5N | 124.9 (16) |
C23—C22—H22 | 126.5 | C23—N5—H5N | 126.1 (16) |
N4—C22—H22 | 126.5 | O6—N6—O5 | 123.2 (2) |
C22—C23—N5 | 107.09 (18) | O6—N6—C29 | 118.0 (2) |
C22—C23—H23 | 126.5 | O5—N6—C29 | 118.7 (2) |
N5—C23—H23 | 126.5 | C5—O1—H1O | 105.9 (17) |
N4—C24—C25 | 110.93 (14) | C25—O4—H4O | 110.0 (18) |
N1—C2—C3—N2 | 0.3 (2) | C28—C29—C30—C31 | −1.9 (3) |
N1—C4—C5—O1 | 63.6 (2) | N6—C29—C30—C31 | 176.16 (19) |
N1—C4—C5—C6 | −173.80 (16) | C29—C30—C31—C26 | −0.3 (3) |
O1—C5—C6—C11 | 20.0 (2) | C27—C26—C31—C30 | 2.2 (3) |
C4—C5—C6—C11 | −98.3 (2) | C25—C26—C31—C30 | −175.12 (19) |
O1—C5—C6—C7 | −159.94 (19) | N1—C1—N2—C3 | −0.5 (2) |
C4—C5—C6—C7 | 81.7 (2) | C2—C3—N2—C1 | 0.1 (2) |
C11—C6—C7—C8 | 2.6 (3) | N2—C1—N1—C2 | 0.7 (2) |
C5—C6—C7—C8 | −177.4 (2) | N2—C1—N1—C4 | 179.03 (17) |
C6—C7—C8—C9 | −0.6 (4) | C3—C2—N1—C1 | −0.6 (2) |
C7—C8—C9—C10 | −2.0 (4) | C3—C2—N1—C4 | −178.94 (17) |
C7—C8—C9—N3 | 178.1 (2) | C5—C4—N1—C1 | −82.8 (2) |
C8—C9—C10—C11 | 2.6 (3) | C5—C4—N1—C2 | 95.3 (2) |
N3—C9—C10—C11 | −177.49 (18) | C10—C9—N3—O2 | 165.1 (2) |
C7—C6—C11—C10 | −2.0 (3) | C8—C9—N3—O2 | −14.9 (3) |
C5—C6—C11—C10 | 178.03 (18) | C10—C9—N3—O3 | −14.4 (3) |
C9—C10—C11—C6 | −0.5 (3) | C8—C9—N3—O3 | 165.6 (2) |
N4—C22—C23—N5 | −0.4 (3) | N5—C21—N4—C22 | −0.9 (2) |
N4—C24—C25—O4 | −61.50 (17) | N5—C21—N4—C24 | −176.16 (17) |
N4—C24—C25—C26 | 175.96 (14) | C23—C22—N4—C21 | 0.8 (2) |
O4—C25—C26—C27 | 145.34 (18) | C23—C22—N4—C24 | 176.07 (18) |
C24—C25—C26—C27 | −96.1 (2) | C25—C24—N4—C21 | 97.9 (2) |
O4—C25—C26—C31 | −37.4 (2) | C25—C24—N4—C22 | −76.5 (2) |
C24—C25—C26—C31 | 81.2 (2) | N4—C21—N5—C23 | 0.7 (2) |
C31—C26—C27—C28 | −2.0 (3) | C22—C23—N5—C21 | −0.2 (3) |
C25—C26—C27—C28 | 175.37 (18) | C30—C29—N6—O6 | 179.6 (2) |
C26—C27—C28—C29 | −0.2 (3) | C28—C29—N6—O6 | −2.2 (3) |
C27—C28—C29—C30 | 2.2 (3) | C30—C29—N6—O5 | −3.6 (3) |
C27—C28—C29—N6 | −175.90 (18) | C28—C29—N6—O5 | 174.5 (2) |
Experimental details
(1aHClH2O) | (1b) | (1bHClH2O) | (1c3H2O) | |
Crystal data | ||||
Chemical formula | C11H11N2O·Cl·H2O | C11H9BrN2O | C11H10BrN2O·Cl·H2O | C11H9N3O3·3(H2O) |
Mr | 240.68 | 265.10 | 319.58 | 285.26 |
Crystal system, space group | Orthorhombic, Pcab | Orthorhombic, Pbca | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 293 | 293 | 293 | 293 |
a, b, c (Å) | 5.1830 (6), 16.808 (7), 27.247 (3) | 10.1389 (7), 7.5691 (5), 27.0498 (15) | 6.845 (5), 7.141 (5), 13.905 (5) | 7.0408 (3), 8.4596 (5), 11.4455 (7) |
α, β, γ (°) | 90, 90, 90 | 90, 90, 90 | 101.723 (5), 95.164 (5), 100.511 (5) | 89.438 (5), 86.904 (4), 82.072 (4) |
V (Å3) | 2373.7 (11) | 2075.9 (2) | 648.6 (7) | 674.22 (6) |
Z | 8 | 8 | 2 | 2 |
Radiation type | Mo Kα | Mo Kα | Cu Kα | Mo Kα |
µ (mm−1) | 0.31 | 3.93 | 6.16 | 0.12 |
Crystal size (mm) | 0.35 × 0.15 × 0.05 | 0.40 × 0.08 × 0.05 | 0.40 × 0.25 × 0.10 | 0.45 × 0.32 × 0.10 |
Data collection | ||||
Diffractometer | Xcalibur, Ruby, Gemini ultra diffractometer | Xcalibur, Ruby, Gemini ultra diffractometer | Xcalibur, Ruby, Gemini ultra diffractometer | Xcalibur, Ruby, Gemini ultra diffractometer |
Absorption correction | Multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | Multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | Multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | Multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
Tmin, Tmax | 0.946, 0.985 | 0.692, 0.822 | 0.197, 0.543 | 0.809, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6343, 2083, 1332 | 7194, 1826, 1505 | 2920, 2355, 1749 | 9754, 2860, 2238 |
Rint | 0.076 | 0.034 | 0.039 | 0.025 |
(sin θ/λ)max (Å−1) | 0.594 | 0.595 | 0.600 | 0.663 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.110, 1.08 | 0.032, 0.076, 1.07 | 0.044, 0.121, 1.06 | 0.046, 0.123, 1.05 |
No. of reflections | 1986 | 1821 | 2143 | 2860 |
No. of parameters | 153 | 137 | 166 | 181 |
No. of restraints | 3 | 0 | 0 | 0 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H-atom parameters constrained | H atoms treated by a mixture of independent and constrained refinement | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.16 | 0.43, −0.27 | 0.50, −0.52 | 0.15, −0.28 |
(2aHCl) | |
Crystal data | |
Chemical formula | C11H12N3O3·Cl |
Mr | 269.69 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 21.9100 (7), 8.0131 (3), 14.3802 (4) |
α, β, γ (°) | 90, 97.325 (3), 90 |
V (Å3) | 2504.09 (14) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.31 |
Crystal size (mm) | 0.30 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Xcalibur, Ruby, Gemini ultra diffractometer |
Absorption correction | Multi-scan CrysAlis PRO, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
Tmin, Tmax | 0.929, 0.970 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20723, 4428, 3979 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.093, 1.05 |
No. of reflections | 4418 |
No. of parameters | 341 |
No. of restraints | 0 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.23, −0.24 |
Computer programs: CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44), CrysAlis PRO, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46), SHELXL97 (Sheldrick, 1997).
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