Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
Heme oxygenase-1 (HO-1) inhibition is associated with antitumor activity. Imidazole-based analogues show effective and selective inhibitory potency of HO-1. In this work, five single-crystal structures of four imidazole-based compounds are presented, with an in-depth structural analysis. In order to study the influence of the conformation of the ligands on binding to protein, conformational data from crystallography are compared with quantum mechanics analysis and molecular docking studies. Molecular docking of imidazole-based analogues in the active site of HO-1 is in good agreement with the experimental structures. Inhibitors interact with the heme cofactor and a hydrophobic pocket (Met34, Phe37, Val50, Leu147 and Phe214) in the HO-1 binding site. An alternate binding mode can be hypothesized for some inhibitors in the series.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520615010410/lo5002sup1.cif
Contains datablocks 1aHClH2O, 1b, 1bHClH2O, 1c3H2O, 2aHCl

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520615010410/lo50021aHClH2Osup2.hkl
Contains datablock jw_ac_hsg05

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520615010410/lo50021bsup3.hkl
Contains datablock bn_sgh05

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520615010410/lo50021bHClH2Osup4.hkl
Contains datablock bn_ca-sg05

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520615010410/lo50021c3H2Osup5.hkl
Contains datablock jw_ac_no2sg05

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520615010410/lo50022aHClsup6.hkl
Contains datablock bn_sgh03a-hcl-b

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520615010410/lo5002sup7.pdf
Details of CSD search

CCDC references: 1020040; 1020041; 1020042; 1020043; 1020044

Computing details top

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).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
(1aHClH2O) top
Crystal data top
C11H11N2O·Cl·H2ODx = 1.347 Mg m3
Mr = 240.68Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PcabCell parameters from 895 reflections
a = 5.1830 (6) Åθ = 4.2–21.3°
b = 16.808 (7) ŵ = 0.31 mm1
c = 27.247 (3) ÅT = 293 K
V = 2373.7 (11) Å3Needle-like, colourless
Z = 80.35 × 0.15 × 0.05 mm
F(000) = 1008
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
2083 independent reflections
Radiation source: fine-focus sealed tube1332 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.076
Detector resolution: 10.3712 pixels mm-1θmax = 25.0°, θmin = 3.9°
ω scansh = 56
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 = 1912
Tmin = 0.946, Tmax = 0.985l = 2832
6343 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H 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 parametersΔρmax = 0.19 e Å3
3 restraintsΔρmin = 0.16 e Å3
Crystal data top
C11H11N2O·Cl·H2OV = 2373.7 (11) Å3
Mr = 240.68Z = 8
Orthorhombic, PcabMo Kα radiation
a = 5.1830 (6) ŵ = 0.31 mm1
b = 16.808 (7) ÅT = 293 K
c = 27.247 (3) Å0.35 × 0.15 × 0.05 mm
Data collection top
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 = 0.985Rint = 0.076
6343 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0613 restraints
wR(F2) = 0.110H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.19 e Å3
1986 reflectionsΔρmin = 0.16 e Å3
153 parameters
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
xyzUiso*/Ueq
O10.8942 (4)0.18538 (15)0.11090 (7)0.0541 (7)
N10.5206 (4)0.11706 (18)0.05702 (9)0.0463 (7)
C50.7475 (5)0.1448 (2)0.13474 (10)0.0374 (8)
C110.6126 (5)0.0862 (2)0.21558 (11)0.0462 (9)
H110.47790.05960.20010.055*
C70.9792 (5)0.1712 (2)0.21171 (11)0.0455 (9)
H71.09370.20210.19360.055*
C100.6457 (6)0.0788 (2)0.26558 (12)0.0553 (10)
H100.53350.04730.28380.066*
C60.7787 (5)0.13299 (19)0.18821 (10)0.0342 (7)
C40.5233 (5)0.1041 (2)0.10980 (10)0.0483 (9)
H4B0.53230.04740.11620.058*
H4A0.36340.12380.12370.058*
C90.8433 (6)0.1178 (3)0.28833 (12)0.0552 (10)
H90.86420.11300.32210.066*
C81.0118 (6)0.1642 (2)0.26184 (12)0.0531 (9)
H81.14630.19050.27750.064*
C20.3604 (6)0.1671 (2)0.03172 (12)0.0560 (11)
H20.22920.19810.04500.067*
N20.6292 (5)0.1116 (2)0.01854 (10)0.0575 (8)
H2N0.70890.09890.04510.069*
C30.4269 (6)0.1632 (3)0.01550 (13)0.0591 (10)
H30.35010.19040.04140.071*
C10.6837 (6)0.0841 (2)0.02569 (12)0.0563 (11)
H10.81350.04800.03340.068*
Cl10.96604 (15)0.03832 (6)0.09885 (3)0.0548 (3)
O20.1390 (6)0.2143 (2)0.87505 (12)0.0786 (9)
H2O0.004 (4)0.2391 (19)0.873 (2)0.15 (3)*
H2P0.101 (7)0.1656 (6)0.8792 (19)0.13 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0528 (12)0.063 (2)0.0463 (13)0.0127 (12)0.0053 (11)0.0107 (12)
N10.0432 (14)0.056 (2)0.0394 (15)0.0027 (14)0.0009 (13)0.0011 (15)
C50.0354 (16)0.037 (2)0.0399 (18)0.0049 (15)0.0026 (15)0.0040 (17)
C110.0490 (18)0.044 (3)0.046 (2)0.0082 (17)0.0010 (15)0.0044 (17)
C70.0446 (17)0.044 (2)0.047 (2)0.0029 (16)0.0051 (15)0.0012 (17)
C100.058 (2)0.063 (3)0.044 (2)0.0015 (19)0.0072 (18)0.0137 (19)
C60.0339 (15)0.026 (2)0.0423 (17)0.0025 (14)0.0033 (14)0.0006 (15)
C40.0491 (18)0.059 (3)0.0364 (18)0.0079 (18)0.0033 (14)0.0018 (17)
C90.066 (2)0.062 (3)0.0368 (18)0.014 (2)0.0001 (18)0.0009 (19)
C80.0538 (19)0.055 (3)0.051 (2)0.0039 (19)0.0049 (18)0.0069 (19)
C20.0536 (19)0.069 (3)0.045 (2)0.014 (2)0.0051 (17)0.004 (2)
N20.0719 (18)0.065 (3)0.0360 (16)0.0002 (18)0.0061 (14)0.0077 (16)
C30.068 (2)0.061 (3)0.049 (2)0.012 (2)0.0121 (18)0.000 (2)
C10.059 (2)0.068 (3)0.042 (2)0.0138 (19)0.0019 (18)0.005 (2)
Cl10.0702 (5)0.0481 (6)0.0459 (5)0.0082 (5)0.0014 (4)0.0022 (5)
O20.0796 (18)0.059 (3)0.097 (2)0.0085 (18)0.0066 (16)0.0090 (19)
Geometric parameters (Å, º) top
O1—C51.211 (3)C4—H4B0.9700
N1—C11.323 (4)C4—H4A0.9700
N1—C21.368 (4)C9—C81.375 (5)
N1—C41.455 (4)C9—H90.9300
C5—C61.479 (4)C8—H80.9300
C5—C41.510 (4)C2—C31.334 (4)
C11—C101.379 (4)C2—H20.9300
C11—C61.384 (4)N2—C11.321 (4)
C11—H110.9300N2—C31.363 (4)
C7—C61.380 (4)N2—H2N0.8600
C7—C81.381 (4)C3—H30.9300
C7—H70.9300C1—H10.9300
C10—C91.365 (4)O2—H2O0.8500 (11)
C10—H100.9300O2—H2P0.8501 (13)
C1—N1—C2108.7 (3)C5—C4—H4A109.1
C1—N1—C4124.6 (3)H4B—C4—H4A107.8
C2—N1—C4126.6 (3)C10—C9—C8120.7 (3)
O1—C5—C6122.4 (3)C10—C9—H9119.7
O1—C5—C4119.8 (3)C8—C9—H9119.7
C6—C5—C4117.8 (3)C9—C8—C7119.4 (3)
C10—C11—C6120.4 (3)C9—C8—H8120.3
C10—C11—H11119.8C7—C8—H8120.3
C6—C11—H11119.8C3—C2—N1107.4 (3)
C6—C7—C8120.7 (3)C3—C2—H2126.3
C6—C7—H7119.6N1—C2—H2126.3
C8—C7—H7119.6C1—N2—C3109.4 (3)
C9—C10—C11119.9 (3)C1—N2—H2N125.3
C9—C10—H10120.0C3—N2—H2N125.3
C11—C10—H10120.0C2—C3—N2106.8 (3)
C7—C6—C11118.9 (3)C2—C3—H3126.6
C7—C6—C5118.5 (3)N2—C3—H3126.6
C11—C6—C5122.6 (3)N2—C1—N1107.8 (3)
N1—C4—C5112.6 (2)N2—C1—H1126.1
N1—C4—H4B109.1N1—C1—H1126.1
C5—C4—H4B109.1H2O—O2—H2P106.24 (19)
N1—C4—H4A109.1
C6—C11—C10—C90.0 (5)C6—C5—C4—N1177.2 (3)
C8—C7—C6—C111.1 (5)C11—C10—C9—C80.4 (6)
C8—C7—C6—C5177.9 (3)C10—C9—C8—C70.2 (6)
C10—C11—C6—C70.8 (5)C6—C7—C8—C90.6 (5)
C10—C11—C6—C5178.2 (3)C1—N1—C2—C30.7 (4)
O1—C5—C6—C71.5 (5)C4—N1—C2—C3178.0 (3)
C4—C5—C6—C7178.6 (3)N1—C2—C3—N20.7 (4)
O1—C5—C6—C11179.5 (3)C1—N2—C3—C20.5 (4)
C4—C5—C6—C110.4 (4)C3—N2—C1—N10.1 (4)
C1—N1—C4—C572.4 (4)C2—N1—C1—N20.4 (4)
C2—N1—C4—C5104.5 (4)C4—N1—C1—N2177.8 (3)
O1—C5—C4—N12.7 (4)
(1b) top
Crystal data top
C11H9BrN2ODx = 1.696 Mg m3
Mr = 265.10Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 2524 reflections
a = 10.1389 (7) Åθ = 3.4–28.1°
b = 7.5691 (5) ŵ = 3.93 mm1
c = 27.0498 (15) ÅT = 293 K
V = 2075.9 (2) Å3Needle-like, colourless
Z = 80.40 × 0.08 × 0.05 mm
F(000) = 1056
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
1826 independent reflections
Radiation source: fine-focus sealed tube1505 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
Detector resolution: 10.3712 pixels mm-1θmax = 25.0°, θmin = 3.4°
ω scansh = 912
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 = 79
Tmin = 0.692, Tmax = 0.822l = 2932
7194 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H-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 reflectionsΔρmax = 0.43 e Å3
137 parametersΔρmin = 0.27 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0030 (3)
Crystal data top
C11H9BrN2OV = 2075.9 (2) Å3
Mr = 265.10Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 10.1389 (7) ŵ = 3.93 mm1
b = 7.5691 (5) ÅT = 293 K
c = 27.0498 (15) Å0.40 × 0.08 × 0.05 mm
Data collection top
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 = 0.822Rint = 0.034
7194 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.076H-atom parameters constrained
S = 1.07Δρmax = 0.43 e Å3
1821 reflectionsΔρmin = 0.27 e Å3
137 parameters
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
xyzUiso*/Ueq
C10.9710 (3)0.3077 (4)0.53886 (10)0.0416 (7)
H11.04420.37740.53190.050*
C20.8099 (3)0.1211 (3)0.52966 (10)0.0394 (7)
H20.75030.04010.51660.047*
C30.8128 (3)0.1835 (4)0.57615 (10)0.0445 (7)
H30.75440.15060.60100.053*
C40.9478 (3)0.1782 (4)0.45398 (9)0.0357 (6)
H4A0.94390.05350.44590.043*
H4B1.03810.21720.44920.043*
C50.8589 (3)0.2791 (3)0.41889 (9)0.0324 (6)
C60.8756 (2)0.2468 (3)0.36502 (9)0.0305 (6)
C70.7789 (3)0.3063 (4)0.33305 (10)0.0395 (7)
H70.70660.36740.34550.047*
C80.7887 (3)0.2760 (4)0.28289 (10)0.0411 (7)
H80.72300.31590.26160.049*
C90.8958 (3)0.1869 (3)0.26456 (9)0.0357 (6)
C100.9941 (3)0.1265 (3)0.29573 (10)0.0386 (7)
H101.06660.06670.28300.046*
C110.9835 (3)0.1559 (3)0.34578 (10)0.0355 (6)
H111.04900.11480.36690.043*
N10.9126 (2)0.2011 (3)0.50543 (8)0.0339 (5)
N20.9137 (2)0.3022 (4)0.58199 (9)0.0495 (7)
O10.7774 (2)0.3806 (3)0.43462 (7)0.0522 (6)
Br10.90954 (3)0.14638 (4)0.195554 (10)0.04969 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0430 (17)0.0470 (16)0.0347 (16)0.0041 (13)0.0094 (14)0.0014 (13)
C20.0307 (15)0.0510 (16)0.0366 (15)0.0001 (12)0.0001 (12)0.0029 (13)
C30.0418 (18)0.0593 (18)0.0323 (15)0.0071 (15)0.0028 (13)0.0046 (14)
C40.0362 (15)0.0452 (15)0.0257 (13)0.0047 (12)0.0001 (12)0.0009 (11)
C50.0313 (14)0.0363 (14)0.0297 (14)0.0001 (12)0.0006 (12)0.0031 (12)
C60.0347 (15)0.0301 (13)0.0267 (13)0.0027 (11)0.0026 (11)0.0004 (11)
C70.0437 (18)0.0421 (14)0.0326 (14)0.0133 (13)0.0038 (13)0.0061 (12)
C80.0469 (18)0.0441 (15)0.0322 (14)0.0095 (13)0.0090 (13)0.0028 (13)
C90.0481 (17)0.0367 (14)0.0222 (13)0.0033 (13)0.0019 (12)0.0021 (11)
C100.0385 (16)0.0424 (15)0.0348 (15)0.0043 (12)0.0062 (13)0.0010 (12)
C110.0330 (15)0.0415 (15)0.0320 (14)0.0049 (12)0.0033 (12)0.0031 (11)
N10.0335 (13)0.0434 (12)0.0248 (11)0.0013 (10)0.0021 (9)0.0013 (10)
N20.0588 (17)0.0623 (16)0.0274 (13)0.0016 (13)0.0053 (12)0.0052 (12)
O10.0575 (14)0.0650 (13)0.0342 (11)0.0278 (11)0.0027 (10)0.0088 (9)
Br10.0671 (3)0.0558 (2)0.0262 (2)0.00046 (15)0.00192 (13)0.00478 (12)
Geometric parameters (Å, º) top
C1—N21.304 (4)C5—C61.487 (3)
C1—N11.349 (3)C6—C71.382 (3)
C1—H10.9300C6—C111.394 (4)
C2—C31.344 (4)C7—C81.379 (4)
C2—N11.372 (3)C7—H70.9300
C2—H20.9300C8—C91.372 (4)
C3—N21.371 (4)C8—H80.9300
C3—H30.9300C9—C101.382 (4)
C4—N11.447 (3)C9—Br11.897 (3)
C4—C51.516 (4)C10—C111.376 (4)
C4—H4A0.9700C10—H100.9300
C4—H4B0.9700C11—H110.9300
C5—O11.205 (3)
N2—C1—N1112.7 (3)C11—C6—C5122.4 (2)
N2—C1—H1123.7C8—C7—C6120.7 (2)
N1—C1—H1123.7C8—C7—H7119.7
C3—C2—N1106.0 (3)C6—C7—H7119.7
C3—C2—H2127.0C9—C8—C7119.6 (2)
N1—C2—H2127.0C9—C8—H8120.2
C2—C3—N2110.8 (3)C7—C8—H8120.2
C2—C3—H3124.6C8—C9—C10120.8 (2)
N2—C3—H3124.6C8—C9—Br1119.5 (2)
N1—C4—C5113.3 (2)C10—C9—Br1119.6 (2)
N1—C4—H4A108.9C11—C10—C9119.4 (3)
C5—C4—H4A108.9C11—C10—H10120.3
N1—C4—H4B108.9C9—C10—H10120.3
C5—C4—H4B108.9C10—C11—C6120.5 (2)
H4A—C4—H4B107.7C10—C11—H11119.7
O1—C5—C6121.9 (2)C6—C11—H11119.7
O1—C5—C4120.5 (2)C1—N1—C2106.1 (2)
C6—C5—C4117.6 (2)C1—N1—C4127.5 (2)
C7—C6—C11119.0 (2)C2—N1—C4126.4 (2)
C7—C6—C5118.6 (2)C1—N2—C3104.5 (2)
N1—C2—C3—N20.6 (3)Br1—C9—C10—C11179.86 (19)
N1—C4—C5—O17.1 (4)C9—C10—C11—C60.5 (4)
N1—C4—C5—C6172.4 (2)C7—C6—C11—C100.3 (4)
O1—C5—C6—C713.2 (4)C5—C6—C11—C10179.0 (2)
C4—C5—C6—C7166.3 (2)N2—C1—N1—C20.2 (3)
O1—C5—C6—C11168.0 (3)N2—C1—N1—C4178.2 (2)
C4—C5—C6—C1112.4 (4)C3—C2—N1—C10.2 (3)
C11—C6—C7—C80.2 (4)C3—C2—N1—C4178.7 (2)
C5—C6—C7—C8178.6 (2)C5—C4—N1—C1101.0 (3)
C6—C7—C8—C90.4 (4)C5—C4—N1—C277.1 (3)
C7—C8—C9—C100.2 (4)N1—C1—N2—C30.6 (3)
C7—C8—C9—Br1179.7 (2)C2—C3—N2—C10.7 (3)
C8—C9—C10—C110.3 (4)
(1bHClH2O) top
Crystal data top
C11H10BrN2O·Cl·H2OZ = 2
Mr = 319.58F(000) = 320
Triclinic, P1Dx = 1.636 Mg m3
a = 6.845 (5) ÅCu Kα radiation, λ = 1.54178 Å
b = 7.141 (5) ÅCell parameters from 1215 reflections
c = 13.905 (5) Åθ = 3.2–65.8°
α = 101.723 (5)°µ = 6.16 mm1
β = 95.164 (5)°T = 293 K
γ = 100.511 (5)°Needle-like, colourless
V = 648.6 (7) Å30.40 × 0.25 × 0.10 mm
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
2355 independent reflections
Radiation source: fine-focus sealed tube1749 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
Detector resolution: 10.3712 pixels mm-1θmax = 67.7°, θmin = 3.3°
ω scansh = 84
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 = 88
Tmin = 0.197, Tmax = 0.543l = 1616
2920 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H 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 parametersΔρmax = 0.50 e Å3
0 restraintsΔρmin = 0.52 e Å3
Crystal data top
C11H10BrN2O·Cl·H2Oγ = 100.511 (5)°
Mr = 319.58V = 648.6 (7) Å3
Triclinic, P1Z = 2
a = 6.845 (5) ÅCu Kα radiation
b = 7.141 (5) ŵ = 6.16 mm1
c = 13.905 (5) ÅT = 293 K
α = 101.723 (5)°0.40 × 0.25 × 0.10 mm
β = 95.164 (5)°
Data collection top
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 = 0.543Rint = 0.039
2920 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.121H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.50 e Å3
2143 reflectionsΔρmin = 0.52 e Å3
166 parameters
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
xyzUiso*/Ueq
C90.2121 (7)0.2946 (7)0.4204 (3)0.0346 (10)
C80.2076 (7)0.0957 (7)0.4009 (3)0.0329 (10)
H80.17990.02140.33620.039*
C70.2446 (6)0.0103 (7)0.4782 (3)0.0321 (10)
H70.24350.12290.46540.039*
C60.2840 (6)0.1182 (6)0.5762 (3)0.0305 (10)
C110.2854 (7)0.3166 (7)0.5947 (3)0.0357 (11)
H110.31040.39020.65950.043*
C100.2496 (7)0.4060 (7)0.5170 (3)0.0399 (11)
H100.25080.53920.52940.048*
C50.3216 (6)0.0156 (7)0.6566 (3)0.0312 (10)
C40.3774 (7)0.1366 (7)0.7623 (3)0.0339 (10)
H4A0.50760.22220.76880.041*
H4B0.27960.21690.77800.041*
C20.2223 (7)0.0738 (7)0.8726 (3)0.0375 (11)
H20.09590.04300.86920.045*
C30.2821 (7)0.2050 (7)0.9191 (4)0.0431 (12)
H30.20590.28090.95480.052*
C10.5354 (7)0.0781 (7)0.8505 (3)0.0400 (12)
H10.66120.05190.83000.048*
N10.3829 (5)0.0068 (5)0.8309 (3)0.0322 (8)
N20.4772 (6)0.2056 (6)0.9040 (3)0.0392 (10)
O10.3131 (5)0.1593 (5)0.6410 (2)0.0425 (8)
O20.2485 (7)0.3911 (8)1.0329 (4)0.0662 (14)
Br10.16581 (8)0.42138 (8)0.31623 (3)0.0433 (2)
Cl10.06891 (17)0.28466 (17)0.84308 (8)0.0382 (3)
H2N0.556 (8)0.292 (7)0.928 (4)0.048 (15)*
H2O0.201 (9)0.444 (10)1.069 (5)0.06 (2)*
H2P0.166 (9)0.351 (9)0.980 (5)0.062 (19)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C90.038 (3)0.038 (3)0.030 (2)0.011 (2)0.0003 (19)0.012 (2)
C80.036 (2)0.033 (3)0.029 (2)0.010 (2)0.0012 (18)0.0036 (19)
C70.032 (2)0.031 (3)0.033 (2)0.0103 (19)0.0028 (19)0.0033 (19)
C60.024 (2)0.032 (3)0.036 (2)0.0070 (18)0.0009 (18)0.0092 (19)
C110.050 (3)0.030 (3)0.025 (2)0.010 (2)0.002 (2)0.0046 (19)
C100.057 (3)0.029 (3)0.032 (2)0.012 (2)0.003 (2)0.0030 (19)
C50.031 (2)0.031 (3)0.034 (2)0.0106 (19)0.0034 (19)0.0080 (19)
C40.040 (3)0.031 (2)0.033 (2)0.010 (2)0.000 (2)0.0130 (19)
C20.037 (3)0.040 (3)0.042 (3)0.012 (2)0.004 (2)0.019 (2)
C30.041 (3)0.045 (3)0.047 (3)0.011 (2)0.005 (2)0.018 (2)
C10.039 (3)0.048 (3)0.040 (3)0.018 (2)0.004 (2)0.017 (2)
N10.036 (2)0.032 (2)0.0314 (19)0.0129 (17)0.0001 (16)0.0101 (16)
N20.049 (2)0.036 (2)0.037 (2)0.0194 (19)0.0021 (19)0.0107 (18)
O10.058 (2)0.0320 (19)0.0372 (18)0.0118 (16)0.0008 (16)0.0080 (14)
O20.072 (3)0.084 (4)0.046 (2)0.055 (3)0.011 (2)0.005 (2)
Br10.0547 (4)0.0453 (4)0.0335 (3)0.0137 (2)0.0003 (2)0.0165 (2)
Cl10.0453 (7)0.0380 (7)0.0351 (6)0.0183 (5)0.0016 (5)0.0099 (5)
Geometric parameters (Å, º) top
C9—C81.385 (6)C4—N11.461 (5)
C9—C101.390 (7)C4—H4A0.9700
C9—Br11.890 (4)C4—H4B0.9700
C8—C71.367 (6)C2—C31.343 (7)
C8—H80.9300C2—N11.377 (6)
C7—C61.397 (6)C2—H20.9300
C7—H70.9300C3—N21.371 (6)
C6—C111.386 (6)C3—H30.9300
C6—C51.485 (6)C1—N21.318 (6)
C11—C101.388 (6)C1—N11.334 (6)
C11—H110.9300C1—H10.9300
C10—H100.9300N2—H2N0.98 (5)
C5—O11.213 (5)O2—H2O0.70 (6)
C5—C41.521 (6)O2—H2P0.85 (6)
C8—C9—C10120.9 (4)N1—C4—H4A109.8
C8—C9—Br1120.8 (3)C5—C4—H4A109.8
C10—C9—Br1118.3 (4)N1—C4—H4B109.8
C7—C8—C9118.9 (4)C5—C4—H4B109.8
C7—C8—H8120.5H4A—C4—H4B108.2
C9—C8—H8120.5C3—C2—N1107.2 (4)
C8—C7—C6121.6 (4)C3—C2—H2126.4
C8—C7—H7119.2N1—C2—H2126.4
C6—C7—H7119.2C2—C3—N2106.8 (4)
C11—C6—C7118.8 (4)C2—C3—H3126.6
C11—C6—C5122.4 (4)N2—C3—H3126.6
C7—C6—C5118.7 (4)N2—C1—N1108.2 (4)
C10—C11—C6120.3 (4)N2—C1—H1125.9
C10—C11—H11119.8N1—C1—H1125.9
C6—C11—H11119.8C1—N1—C2108.3 (4)
C11—C10—C9119.4 (4)C1—N1—C4125.1 (4)
C11—C10—H10120.3C2—N1—C4125.8 (4)
C9—C10—H10120.3C1—N2—C3109.4 (4)
O1—C5—C6122.6 (4)C1—N2—H2N127 (3)
O1—C5—C4119.1 (4)C3—N2—H2N124 (3)
C6—C5—C4118.3 (4)H2O—O2—H2P107 (7)
N1—C4—C5109.6 (4)
C10—C9—C8—C71.2 (7)C7—C6—C5—C4176.2 (4)
Br1—C9—C8—C7179.1 (3)O1—C5—C4—N18.4 (6)
C9—C8—C7—C60.8 (7)C6—C5—C4—N1172.9 (3)
C8—C7—C6—C110.0 (7)N1—C2—C3—N21.0 (6)
C8—C7—C6—C5179.6 (4)N2—C1—N1—C21.0 (6)
C7—C6—C11—C100.5 (7)N2—C1—N1—C4171.1 (4)
C5—C6—C11—C10179.9 (4)C3—C2—N1—C11.2 (6)
C6—C11—C10—C90.1 (7)C3—C2—N1—C4171.3 (4)
C8—C9—C10—C110.8 (8)C5—C4—N1—C180.7 (6)
Br1—C9—C10—C11179.6 (4)C5—C4—N1—C287.7 (5)
C11—C6—C5—O1177.1 (4)N1—C1—N2—C30.4 (6)
C7—C6—C5—O12.5 (6)C2—C3—N2—C10.4 (6)
C11—C6—C5—C44.2 (6)
(1c3H2O) top
Crystal data top
C11H9N3O3·3(H2O)Z = 2
Mr = 285.26F(000) = 300
Triclinic, P1Dx = 1.405 Mg m3
a = 7.0408 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.4596 (5) ÅCell parameters from 3247 reflections
c = 11.4455 (7) Åθ = 3.5–27.0°
α = 89.438 (5)°µ = 0.12 mm1
β = 86.904 (4)°T = 293 K
γ = 82.072 (4)°Needle-like, colourless
V = 674.22 (6) Å30.45 × 0.32 × 0.10 mm
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
2860 independent reflections
Radiation source: fine-focus sealed tube2238 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
Detector resolution: 10.3712 pixels mm-1θmax = 28.1°, θmin = 3.3°
ω scansh = 99
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 = 1110
Tmin = 0.809, Tmax = 1.000l = 1514
9754 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-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 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C11H9N3O3·3(H2O)γ = 82.072 (4)°
Mr = 285.26V = 674.22 (6) Å3
Triclinic, P1Z = 2
a = 7.0408 (3) ÅMo Kα radiation
b = 8.4596 (5) ŵ = 0.12 mm1
c = 11.4455 (7) ÅT = 293 K
α = 89.438 (5)°0.45 × 0.32 × 0.10 mm
β = 86.904 (4)°
Data collection top
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 = 1.000Rint = 0.025
9754 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.123H-atom parameters constrained
S = 1.05Δρmax = 0.15 e Å3
2860 reflectionsΔρmin = 0.28 e Å3
181 parameters
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
xyzUiso*/Ueq
N10.46324 (19)0.57267 (17)0.65054 (12)0.0414 (4)
N20.2276 (2)0.4374 (2)0.61396 (15)0.0563 (4)
N31.2329 (2)0.81633 (18)1.07608 (14)0.0454 (4)
O10.47025 (16)0.60934 (15)0.88362 (11)0.0485 (3)
O21.2617 (2)0.7520 (2)1.17057 (13)0.0706 (5)
O31.33078 (19)0.91217 (17)1.03256 (13)0.0591 (4)
C10.3947 (3)0.4327 (2)0.65951 (17)0.0526 (5)
H10.45880.34230.69430.063*
C30.1868 (3)0.5896 (2)0.57362 (17)0.0537 (5)
H30.07610.62940.53620.064*
C20.3289 (3)0.6744 (2)0.59545 (17)0.0515 (5)
H20.33460.78100.57680.062*
C40.6381 (2)0.6111 (2)0.69843 (15)0.0424 (4)
H4A0.67300.70740.66130.051*
H4B0.74170.52510.68110.051*
C50.6144 (2)0.63593 (19)0.82961 (14)0.0358 (4)
C60.7773 (2)0.68798 (18)0.89114 (14)0.0338 (4)
C70.7817 (2)0.6637 (2)1.01146 (15)0.0406 (4)
H70.68290.61931.05110.049*
C80.9308 (2)0.7049 (2)1.07242 (15)0.0424 (4)
H80.93620.68631.15250.051*
C91.0720 (2)0.77451 (19)1.01137 (15)0.0371 (4)
C101.0712 (2)0.8032 (2)0.89326 (15)0.0414 (4)
H101.16750.85220.85500.050*
C110.9229 (2)0.7571 (2)0.83234 (15)0.0406 (4)
H110.92100.77260.75180.049*
O990.1349 (2)0.12450 (17)0.62347 (13)0.0642 (4)
O980.4506 (2)0.00097 (18)0.75108 (12)0.0637 (4)
O970.2217 (2)0.0003 (2)0.39699 (13)0.0722 (5)
H99A0.15430.22990.62040.050*
H97A0.46670.03150.83140.050*
H98B0.12480.05650.38640.050*
H97B0.56620.00900.70150.050*
H98A0.19480.03770.47930.050*
H99B0.24250.08560.66760.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0397 (7)0.0469 (8)0.0407 (8)0.0126 (6)0.0110 (6)0.0026 (6)
N20.0515 (9)0.0647 (11)0.0585 (10)0.0221 (8)0.0183 (8)0.0040 (8)
N30.0367 (8)0.0479 (9)0.0531 (9)0.0068 (7)0.0099 (7)0.0106 (7)
O10.0378 (6)0.0623 (8)0.0492 (7)0.0205 (6)0.0024 (5)0.0014 (6)
O20.0667 (9)0.0919 (12)0.0602 (9)0.0248 (8)0.0329 (7)0.0109 (8)
O30.0504 (8)0.0624 (9)0.0709 (9)0.0267 (7)0.0123 (7)0.0072 (7)
C10.0548 (11)0.0473 (11)0.0608 (12)0.0178 (9)0.0208 (9)0.0036 (9)
C30.0460 (10)0.0633 (13)0.0526 (11)0.0033 (9)0.0194 (9)0.0086 (9)
C20.0560 (11)0.0462 (11)0.0535 (11)0.0056 (9)0.0189 (9)0.0017 (9)
C40.0374 (8)0.0508 (10)0.0422 (10)0.0155 (8)0.0067 (7)0.0037 (8)
C50.0328 (8)0.0340 (8)0.0421 (9)0.0091 (7)0.0047 (7)0.0017 (7)
C60.0301 (8)0.0339 (8)0.0381 (9)0.0057 (6)0.0041 (6)0.0022 (7)
C70.0377 (9)0.0461 (10)0.0402 (9)0.0143 (7)0.0001 (7)0.0005 (7)
C80.0437 (9)0.0494 (10)0.0355 (9)0.0101 (8)0.0057 (7)0.0021 (7)
C90.0302 (8)0.0364 (9)0.0454 (10)0.0048 (7)0.0079 (7)0.0067 (7)
C100.0340 (8)0.0475 (10)0.0455 (10)0.0146 (7)0.0029 (7)0.0031 (8)
C110.0369 (8)0.0509 (10)0.0362 (9)0.0126 (7)0.0047 (7)0.0026 (7)
O990.0636 (9)0.0654 (9)0.0702 (10)0.0253 (7)0.0200 (7)0.0047 (7)
O980.0592 (8)0.0769 (10)0.0603 (9)0.0240 (7)0.0123 (7)0.0083 (7)
O970.0731 (10)0.0947 (12)0.0566 (9)0.0379 (9)0.0064 (7)0.0001 (8)
Geometric parameters (Å, º) top
N1—C11.340 (2)C6—C111.389 (2)
N1—C21.365 (2)C6—C71.392 (2)
N1—C41.452 (2)C7—C81.377 (2)
N2—C11.308 (2)C7—H70.9300
N2—C31.362 (3)C8—C91.378 (2)
N3—O21.220 (2)C8—H80.9300
N3—O31.2206 (19)C9—C101.371 (2)
N3—C91.471 (2)C10—C111.387 (2)
O1—C51.2066 (19)C10—H100.9300
C1—H10.9300C11—H110.9300
C3—C21.344 (3)O99—H99A0.9205
C3—H30.9300O99—H99B0.9522
C2—H20.9300O98—H97A0.9789
C4—C51.515 (2)O98—H97B0.9798
C4—H4A0.9700O97—H98B0.9014
C4—H4B0.9700O97—H98A0.9967
C5—C61.496 (2)
C1—N1—C2106.24 (15)O1—C5—C4120.80 (14)
C1—N1—C4126.56 (15)C6—C5—C4118.35 (13)
C2—N1—C4127.03 (15)C11—C6—C7119.68 (14)
C1—N2—C3104.60 (15)C11—C6—C5122.38 (14)
O2—N3—O3123.52 (14)C7—C6—C5117.94 (14)
O2—N3—C9117.83 (15)C8—C7—C6120.62 (15)
O3—N3—C9118.64 (15)C8—C7—H7119.7
N2—C1—N1112.50 (17)C6—C7—H7119.7
N2—C1—H1123.8C7—C8—C9118.09 (15)
N1—C1—H1123.8C7—C8—H8121.0
C2—C3—N2110.52 (16)C9—C8—H8121.0
C2—C3—H3124.7C10—C9—C8123.15 (14)
N2—C3—H3124.7C10—C9—N3118.71 (14)
C3—C2—N1106.15 (17)C8—C9—N3118.12 (15)
C3—C2—H2126.9C9—C10—C11118.18 (15)
N1—C2—H2126.9C9—C10—H10120.9
N1—C4—C5111.73 (14)C11—C10—H10120.9
N1—C4—H4A109.3C10—C11—C6120.25 (15)
C5—C4—H4A109.3C10—C11—H11119.9
N1—C4—H4B109.3C6—C11—H11119.9
C5—C4—H4B109.3H99A—O99—H99B97.5
H4A—C4—H4B107.9H97A—O98—H97B110.6
O1—C5—C6120.81 (15)H98B—O97—H98A102.3
C3—N2—C1—N10.1 (2)C11—C6—C7—C81.2 (3)
C2—N1—C1—N20.3 (2)C5—C6—C7—C8178.12 (15)
C4—N1—C1—N2175.80 (16)C6—C7—C8—C91.7 (3)
C1—N2—C3—C20.1 (2)C7—C8—C9—C100.5 (3)
N2—C3—C2—N10.3 (2)C7—C8—C9—N3179.09 (15)
C1—N1—C2—C30.3 (2)O2—N3—C9—C10159.83 (17)
C4—N1—C2—C3175.82 (17)O3—N3—C9—C1019.7 (2)
C1—N1—C4—C575.1 (2)O2—N3—C9—C818.8 (2)
C2—N1—C4—C599.5 (2)O3—N3—C9—C8161.64 (16)
N1—C4—C5—O16.7 (2)C8—C9—C10—C111.2 (3)
N1—C4—C5—C6175.66 (13)N3—C9—C10—C11177.34 (15)
O1—C5—C6—C11163.62 (16)C9—C10—C11—C61.8 (3)
C4—C5—C6—C1118.8 (2)C7—C6—C11—C100.6 (3)
O1—C5—C6—C717.1 (2)C5—C6—C11—C10179.88 (15)
C4—C5—C6—C7160.55 (15)
(2aHCl) top
Crystal data top
C11H12N3O3·ClF(000) = 1120
Mr = 269.69Dx = 1.431 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 21.9100 (7) ÅCell parameters from 10843 reflections
b = 8.0131 (3) Åθ = 3.3–29.3°
c = 14.3802 (4) ŵ = 0.31 mm1
β = 97.325 (3)°T = 293 K
V = 2504.09 (14) Å3Prim, colourless
Z = 80.30 × 0.20 × 0.10 mm
Data collection top
Xcalibur, Ruby, Gemini ultra
diffractometer
4428 independent reflections
Radiation source: fine-focus sealed tube3979 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
Detector resolution: 10.3712 pixels mm-1θmax = 25.0°, θmin = 3.4°
ω scansh = 2625
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 = 99
Tmin = 0.929, Tmax = 0.970l = 1617
20723 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H 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 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C11H12N3O3·ClV = 2504.09 (14) Å3
Mr = 269.69Z = 8
Monoclinic, P21/cMo Kα radiation
a = 21.9100 (7) ŵ = 0.31 mm1
b = 8.0131 (3) ÅT = 293 K
c = 14.3802 (4) Å0.30 × 0.20 × 0.10 mm
β = 97.325 (3)°
Data collection top
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 = 0.970Rint = 0.022
20723 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.093H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.23 e Å3
4418 reflectionsΔρmin = 0.24 e Å3
341 parameters
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
xyzUiso*/Ueq
C10.39014 (10)0.0380 (3)0.45781 (14)0.0554 (5)
H10.35720.03270.43900.066*
C20.45540 (10)0.2009 (2)0.54226 (15)0.0537 (5)
H20.47490.26200.59250.064*
C30.47310 (10)0.1880 (3)0.45663 (15)0.0573 (5)
H30.50710.23890.43610.069*
C40.36802 (10)0.0821 (3)0.62132 (14)0.0547 (5)
H4A0.37480.17630.66380.066*
H4B0.32440.07720.59860.066*
C50.38716 (8)0.0777 (2)0.67400 (12)0.0417 (4)
H50.43180.07690.69210.050*
C60.35520 (8)0.0891 (2)0.76181 (12)0.0403 (4)
C70.37933 (11)0.0035 (3)0.84130 (15)0.0638 (6)
H70.41570.05650.84110.077*
C80.35039 (11)0.0053 (3)0.92114 (15)0.0651 (6)
H80.36660.05350.97440.078*
C90.29737 (9)0.0956 (2)0.92004 (13)0.0474 (5)
C100.27354 (9)0.1870 (3)0.84388 (14)0.0511 (5)
H100.23830.25100.84560.061*
C110.30273 (9)0.1828 (3)0.76414 (13)0.0477 (4)
H110.28680.24380.71160.057*
C210.05533 (9)0.5727 (2)0.66467 (14)0.0492 (5)
H210.04470.56910.72520.059*
C220.09709 (10)0.5152 (3)0.53917 (14)0.0548 (5)
H220.12070.46390.49800.066*
C230.05931 (10)0.6451 (3)0.52014 (15)0.0615 (6)
H230.05180.70170.46340.074*
C240.12577 (8)0.3294 (2)0.67931 (12)0.0423 (4)
H24A0.12730.34450.74650.051*
H24B0.16770.32360.66460.051*
C250.09263 (8)0.1675 (2)0.65045 (12)0.0434 (4)
H250.08940.15530.58220.052*
C260.12888 (8)0.0227 (2)0.69673 (12)0.0411 (4)
C270.16951 (9)0.0648 (2)0.64883 (13)0.0480 (5)
H270.17220.03920.58640.058*
C280.20606 (9)0.1895 (3)0.69241 (14)0.0523 (5)
H280.23330.24840.66010.063*
C290.20123 (9)0.2242 (2)0.78475 (14)0.0479 (5)
C300.16019 (10)0.1435 (3)0.83352 (14)0.0549 (5)
H300.15700.17170.89540.066*
C310.12380 (9)0.0198 (3)0.78898 (13)0.0523 (5)
H310.09560.03580.82100.063*
N20.43193 (9)0.0867 (2)0.40558 (13)0.0579 (5)
N10.40301 (7)0.1068 (2)0.54169 (11)0.0479 (4)
N30.26493 (10)0.0946 (3)1.00319 (13)0.0648 (5)
N40.09446 (7)0.47182 (19)0.63073 (10)0.0400 (3)
N50.03384 (8)0.6791 (2)0.59943 (13)0.0534 (4)
N60.24265 (9)0.3485 (2)0.83428 (16)0.0687 (5)
O10.37147 (7)0.20963 (18)0.61034 (9)0.0507 (3)
O20.27864 (10)0.0119 (3)1.06269 (13)0.0946 (6)
O30.22527 (9)0.1998 (3)1.00893 (13)0.0938 (6)
O40.03272 (6)0.18148 (19)0.67729 (10)0.0539 (4)
O50.24127 (9)0.3696 (3)0.91796 (15)0.0950 (6)
O60.27855 (12)0.4200 (3)0.79039 (16)0.1221 (9)
Cl10.06934 (2)0.05900 (6)0.59702 (3)0.04943 (14)
Cl20.45182 (3)0.48449 (7)0.70812 (4)0.06535 (18)
H1O0.3900 (11)0.295 (3)0.6344 (17)0.070 (8)*
H4O0.0087 (13)0.104 (4)0.6494 (19)0.089 (9)*
H5N0.0057 (11)0.751 (3)0.6048 (16)0.066 (7)*
H1N0.4328 (11)0.053 (3)0.3500 (19)0.074 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0584 (12)0.0572 (12)0.0503 (11)0.0082 (10)0.0062 (10)0.0071 (10)
C20.0614 (13)0.0430 (11)0.0592 (12)0.0035 (10)0.0172 (10)0.0037 (9)
C30.0621 (13)0.0513 (12)0.0632 (13)0.0119 (11)0.0258 (11)0.0156 (10)
C40.0637 (13)0.0487 (11)0.0569 (12)0.0106 (10)0.0283 (10)0.0072 (9)
C50.0427 (10)0.0431 (10)0.0405 (9)0.0015 (8)0.0098 (8)0.0008 (8)
C60.0442 (10)0.0374 (9)0.0401 (9)0.0025 (8)0.0083 (7)0.0001 (8)
C70.0696 (14)0.0671 (14)0.0581 (13)0.0287 (12)0.0216 (11)0.0187 (11)
C80.0798 (15)0.0686 (14)0.0497 (12)0.0176 (13)0.0187 (11)0.0222 (11)
C90.0514 (11)0.0511 (11)0.0421 (10)0.0128 (9)0.0155 (8)0.0025 (8)
C100.0425 (10)0.0614 (13)0.0504 (11)0.0039 (9)0.0105 (8)0.0020 (9)
C110.0465 (10)0.0561 (12)0.0405 (9)0.0055 (9)0.0054 (8)0.0050 (9)
C210.0542 (11)0.0501 (11)0.0445 (10)0.0042 (10)0.0109 (9)0.0032 (9)
C220.0596 (12)0.0643 (13)0.0438 (10)0.0154 (11)0.0188 (9)0.0152 (9)
C230.0673 (14)0.0616 (13)0.0559 (12)0.0114 (11)0.0090 (10)0.0208 (11)
C240.0407 (9)0.0506 (11)0.0353 (9)0.0058 (8)0.0040 (7)0.0061 (8)
C250.0483 (10)0.0493 (11)0.0322 (8)0.0074 (9)0.0037 (7)0.0010 (8)
C260.0433 (10)0.0415 (10)0.0380 (9)0.0008 (8)0.0035 (7)0.0032 (8)
C270.0569 (11)0.0495 (11)0.0394 (9)0.0022 (9)0.0124 (8)0.0027 (8)
C280.0532 (11)0.0471 (11)0.0583 (12)0.0073 (9)0.0129 (9)0.0106 (9)
C290.0493 (11)0.0355 (9)0.0565 (11)0.0030 (8)0.0024 (9)0.0017 (8)
C300.0629 (13)0.0607 (13)0.0417 (10)0.0092 (11)0.0086 (9)0.0089 (9)
C310.0558 (12)0.0624 (13)0.0406 (10)0.0173 (10)0.0136 (9)0.0036 (9)
N20.0707 (12)0.0623 (12)0.0428 (10)0.0188 (10)0.0152 (9)0.0106 (9)
N10.0553 (10)0.0420 (9)0.0494 (9)0.0097 (8)0.0181 (7)0.0088 (7)
N30.0672 (12)0.0808 (14)0.0500 (10)0.0270 (11)0.0215 (9)0.0065 (10)
N40.0407 (8)0.0435 (8)0.0366 (7)0.0038 (7)0.0077 (6)0.0037 (6)
N50.0500 (10)0.0429 (9)0.0669 (11)0.0090 (8)0.0057 (8)0.0026 (8)
N60.0731 (13)0.0499 (11)0.0786 (14)0.0145 (10)0.0082 (11)0.0017 (10)
O10.0662 (9)0.0461 (8)0.0402 (7)0.0043 (7)0.0081 (6)0.0022 (6)
O20.1329 (17)0.0959 (14)0.0623 (11)0.0300 (13)0.0411 (11)0.0140 (10)
O30.0742 (12)0.1387 (18)0.0768 (12)0.0064 (13)0.0418 (10)0.0079 (12)
O40.0428 (7)0.0556 (9)0.0623 (9)0.0022 (7)0.0033 (6)0.0020 (7)
O50.0931 (14)0.1020 (15)0.0873 (14)0.0298 (11)0.0020 (11)0.0380 (12)
O60.153 (2)0.1093 (17)0.0980 (15)0.0890 (17)0.0069 (14)0.0156 (13)
Cl10.0551 (3)0.0540 (3)0.0388 (2)0.0064 (2)0.00474 (19)0.0020 (2)
Cl20.0797 (4)0.0661 (4)0.0524 (3)0.0229 (3)0.0167 (3)0.0063 (2)
Geometric parameters (Å, º) top
C1—N21.315 (3)C22—N41.370 (2)
C1—N11.323 (3)C22—H220.9300
C1—H10.9300C23—N51.359 (3)
C2—C31.341 (3)C23—H230.9300
C2—N11.372 (3)C24—N41.462 (2)
C2—H20.9300C24—C251.518 (3)
C3—N21.358 (3)C24—H24A0.9700
C3—H30.9300C24—H24B0.9700
C4—N11.470 (2)C25—O41.419 (2)
C4—C51.519 (3)C25—C261.512 (3)
C4—H4A0.9700C25—H250.9800
C4—H4B0.9700C26—C271.384 (3)
C5—O11.412 (2)C26—C311.388 (3)
C5—C61.523 (2)C27—C281.380 (3)
C5—H50.9800C27—H270.9300
C6—C111.377 (3)C28—C291.374 (3)
C6—C71.380 (3)C28—H280.9300
C7—C81.381 (3)C29—C301.371 (3)
C7—H70.9300C29—N61.469 (3)
C8—C91.367 (3)C30—C311.378 (3)
C8—H80.9300C30—H300.9300
C9—C101.365 (3)C31—H310.9300
C9—N31.467 (3)N2—H1N0.85 (3)
C10—C111.383 (3)N3—O21.219 (3)
C10—H100.9300N3—O31.221 (3)
C11—H110.9300N5—H5N0.85 (2)
C21—N51.310 (3)N6—O61.213 (3)
C21—N41.317 (2)N6—O51.219 (3)
C21—H210.9300O1—H1O0.84 (3)
C22—C231.336 (3)O4—H4O0.87 (3)
N2—C1—N1108.3 (2)N4—C24—H24A109.5
N2—C1—H1125.9C25—C24—H24A109.5
N1—C1—H1125.9N4—C24—H24B109.5
C3—C2—N1107.0 (2)C25—C24—H24B109.5
C3—C2—H2126.5H24A—C24—H24B108.0
N1—C2—H2126.5O4—C25—C26113.14 (15)
C2—C3—N2107.0 (2)O4—C25—C24106.57 (15)
C2—C3—H3126.5C26—C25—C24109.22 (14)
N2—C3—H3126.5O4—C25—H25109.3
N1—C4—C5111.31 (15)C26—C25—H25109.3
N1—C4—H4A109.4C24—C25—H25109.3
C5—C4—H4A109.4C27—C26—C31119.12 (17)
N1—C4—H4B109.4C27—C26—C25120.34 (16)
C5—C4—H4B109.4C31—C26—C25120.49 (16)
H4A—C4—H4B108.0C28—C27—C26120.91 (18)
O1—C5—C4106.19 (15)C28—C27—H27119.5
O1—C5—C6113.14 (15)C26—C27—H27119.5
C4—C5—C6109.70 (15)C29—C28—C27118.30 (18)
O1—C5—H5109.2C29—C28—H28120.8
C4—C5—H5109.2C27—C28—H28120.8
C6—C5—H5109.2C30—C29—C28122.34 (18)
C11—C6—C7118.95 (17)C30—C29—N6118.47 (19)
C11—C6—C5121.78 (16)C28—C29—N6119.16 (19)
C7—C6—C5119.27 (17)C29—C30—C31118.69 (18)
C6—C7—C8121.0 (2)C29—C30—H30120.7
C6—C7—H7119.5C31—C30—H30120.7
C8—C7—H7119.5C30—C31—C26120.57 (18)
C9—C8—C7118.41 (19)C30—C31—H31119.7
C9—C8—H8120.8C26—C31—H31119.7
C7—C8—H8120.8C1—N2—C3109.37 (19)
C10—C9—C8122.08 (18)C1—N2—H1N123.1 (18)
C10—C9—N3118.76 (19)C3—N2—H1N127.5 (17)
C8—C9—N3119.16 (19)C1—N1—C2108.38 (17)
C9—C10—C11118.82 (18)C1—N1—C4125.60 (19)
C9—C10—H10120.6C2—N1—C4126.00 (18)
C11—C10—H10120.6O2—N3—O3123.4 (2)
C6—C11—C10120.63 (18)O2—N3—C9118.3 (2)
C6—C11—H11119.7O3—N3—C9118.3 (2)
C10—C11—H11119.7C21—N4—C22108.02 (16)
N5—C21—N4109.00 (17)C21—N4—C24126.17 (15)
N5—C21—H21125.5C22—N4—C24125.63 (15)
N4—C21—H21125.5C21—N5—C23108.80 (18)
C23—C22—N4107.08 (18)C21—N5—H5N124.9 (16)
C23—C22—H22126.5C23—N5—H5N126.1 (16)
N4—C22—H22126.5O6—N6—O5123.2 (2)
C22—C23—N5107.09 (18)O6—N6—C29118.0 (2)
C22—C23—H23126.5O5—N6—C29118.7 (2)
N5—C23—H23126.5C5—O1—H1O105.9 (17)
N4—C24—C25110.93 (14)C25—O4—H4O110.0 (18)
N1—C2—C3—N20.3 (2)C28—C29—C30—C311.9 (3)
N1—C4—C5—O163.6 (2)N6—C29—C30—C31176.16 (19)
N1—C4—C5—C6173.80 (16)C29—C30—C31—C260.3 (3)
O1—C5—C6—C1120.0 (2)C27—C26—C31—C302.2 (3)
C4—C5—C6—C1198.3 (2)C25—C26—C31—C30175.12 (19)
O1—C5—C6—C7159.94 (19)N1—C1—N2—C30.5 (2)
C4—C5—C6—C781.7 (2)C2—C3—N2—C10.1 (2)
C11—C6—C7—C82.6 (3)N2—C1—N1—C20.7 (2)
C5—C6—C7—C8177.4 (2)N2—C1—N1—C4179.03 (17)
C6—C7—C8—C90.6 (4)C3—C2—N1—C10.6 (2)
C7—C8—C9—C102.0 (4)C3—C2—N1—C4178.94 (17)
C7—C8—C9—N3178.1 (2)C5—C4—N1—C182.8 (2)
C8—C9—C10—C112.6 (3)C5—C4—N1—C295.3 (2)
N3—C9—C10—C11177.49 (18)C10—C9—N3—O2165.1 (2)
C7—C6—C11—C102.0 (3)C8—C9—N3—O214.9 (3)
C5—C6—C11—C10178.03 (18)C10—C9—N3—O314.4 (3)
C9—C10—C11—C60.5 (3)C8—C9—N3—O3165.6 (2)
N4—C22—C23—N50.4 (3)N5—C21—N4—C220.9 (2)
N4—C24—C25—O461.50 (17)N5—C21—N4—C24176.16 (17)
N4—C24—C25—C26175.96 (14)C23—C22—N4—C210.8 (2)
O4—C25—C26—C27145.34 (18)C23—C22—N4—C24176.07 (18)
C24—C25—C26—C2796.1 (2)C25—C24—N4—C2197.9 (2)
O4—C25—C26—C3137.4 (2)C25—C24—N4—C2276.5 (2)
C24—C25—C26—C3181.2 (2)N4—C21—N5—C230.7 (2)
C31—C26—C27—C282.0 (3)C22—C23—N5—C210.2 (3)
C25—C26—C27—C28175.37 (18)C30—C29—N6—O6179.6 (2)
C26—C27—C28—C290.2 (3)C28—C29—N6—O62.2 (3)
C27—C28—C29—C302.2 (3)C30—C29—N6—O53.6 (3)
C27—C28—C29—N6175.90 (18)C28—C29—N6—O5174.5 (2)

Experimental details

(1aHClH2O)(1b)(1bHClH2O)(1c3H2O)
Crystal data
Chemical formulaC11H11N2O·Cl·H2OC11H9BrN2OC11H10BrN2O·Cl·H2OC11H9N3O3·3(H2O)
Mr240.68265.10319.58285.26
Crystal system, space groupOrthorhombic, PcabOrthorhombic, PbcaTriclinic, P1Triclinic, P1
Temperature (K)293293293293
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, 9090, 90, 90101.723 (5), 95.164 (5), 100.511 (5)89.438 (5), 86.904 (4), 82.072 (4)
V3)2373.7 (11)2075.9 (2)648.6 (7)674.22 (6)
Z8822
Radiation typeMo KαMo KαCu KαMo Kα
µ (mm1)0.313.936.160.12
Crystal size (mm)0.35 × 0.15 × 0.050.40 × 0.08 × 0.050.40 × 0.25 × 0.100.45 × 0.32 × 0.10
Data collection
DiffractometerXcalibur, Ruby, Gemini ultra
diffractometer
Xcalibur, Ruby, Gemini ultra
diffractometer
Xcalibur, Ruby, Gemini ultra
diffractometer
Xcalibur, Ruby, Gemini ultra
diffractometer
Absorption correctionMulti-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, Tmax0.946, 0.9850.692, 0.8220.197, 0.5430.809, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
6343, 2083, 1332 7194, 1826, 1505 2920, 2355, 1749 9754, 2860, 2238
Rint0.0760.0340.0390.025
(sin θ/λ)max1)0.5940.5950.6000.663
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 reflections1986182121432860
No. of parameters153137166181
No. of restraints3000
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH-atom parameters constrainedH atoms treated by a mixture of independent and constrained refinementH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.160.43, 0.270.50, 0.520.15, 0.28


(2aHCl)
Crystal data
Chemical formulaC11H12N3O3·Cl
Mr269.69
Crystal system, space groupMonoclinic, 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
V3)2504.09 (14)
Z8
Radiation typeMo Kα
µ (mm1)0.31
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerXcalibur, Ruby, Gemini ultra
diffractometer
Absorption correctionMulti-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, Tmax0.929, 0.970
No. of measured, independent and
observed [I > 2σ(I)] reflections
20723, 4428, 3979
Rint0.022
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.093, 1.05
No. of reflections4418
No. of parameters341
No. of restraints0
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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).

 

Subscribe to Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. B
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds