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The crystal structures of co-crystals of two systems of chiral carboxylic acids, optically active and racemic 2-phenylpropionic acid and 2-phenylbutyric acid, with isonicotinamide are reported to investigate the effects of the chirality of the chiral carboxylic acids on the melting point of the co-crystal complexes. It was found that the racemic co-crystal has a higher melting point than the optically active co-crystal, which correlates with the denser packing arrangement inherent in centrosymmetric space groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768108034526/bs5070sup1.cif
Contains datablocks I, II, III, IV, V, VII, VIII, IX

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768108034526/bs5070sup2.pdf
X-ray diffraction patterns and DSC traces

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108034526/bs5070Isup3.fcf
Contains datablock I

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108034526/bs5070IIsup4.fcf
Contains datablock II

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108034526/bs5070IIIsup5.fcf
Contains datablock III

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108034526/bs5070IVsup6.fcf
Contains datablock IV

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108034526/bs5070Vsup7.fcf
Contains datablock V

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108034526/bs5070VIIsup8.fcf
Contains datablock VII

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108034526/bs5070VIIIsup9.fcf
Contains datablock VIII

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108034526/bs5070IXsup10.fcf
Contains datablock IX

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768108034526/bs5070IVsup11.pdf
Raw XRD data fo IV

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768108034526/bs5070Vsup12.pdf
Raw XRD data for V

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768108034526/bs5070VIsup13.pdf
Raw XRD data for VI

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768108034526/bs5070VIIsup14.pdf
Raw XRD data for VII

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768108034526/bs5070VIIIsup15.pdf
Raw XRD data for VIII

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768108034526/bs5070IXsup16.pdf
Raw XRD data for IX

CCDC references: 718192; 718193; 718194; 718195; 718196; 718197; 718198; 718199

Computing details top

For all compounds, data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002).

(I) (R)-2-phenylpropionic acid top
Crystal data top
C9H10O2F(000) = 160
Mr = 150.17Dx = 1.286 Mg m3
Monoclinic, P21Melting point = 302–303 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 6.3758 (13) ÅCell parameters from 6231 reflections
b = 7.1703 (14) Åθ = 0.4–28.3°
c = 8.6281 (17) ŵ = 0.09 mm1
β = 100.64 (3)°T = 173 K
V = 387.66 (13) Å3Spheroid, colourless
Z = 20.55 × 0.46 × 0.4 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
910 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
2.0° φ and ω scansθmax = 28.0°, θmin = 3.3°
Absorption correction: multi-scan
SADABS (Sheldrick, 1996)
h = 88
Tmin = 0.953, Tmax = 0.967k = 99
6058 measured reflectionsl = 911
1001 independent 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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 0.98 w = 1/[σ2(Fo2) + (0.0628P)2 + 0.0427P]
where P = (Fo2 + 2Fc2)/3
1001 reflections(Δ/σ)max = 0.035
104 parametersΔρmax = 0.13 e Å3
1 restraintΔρmin = 0.19 e Å3
Special details top

Experimental. absorption corrections were made using the program SADABS (Sheldrick, 1996).

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
C10.6538 (3)0.5545 (3)0.08956 (18)0.0237 (3)
C20.8021 (3)0.7030 (2)0.16964 (19)0.0249 (4)
H20.75280.82530.12020.03*
C31.0271 (3)0.6683 (3)0.1400 (2)0.0348 (4)
H3A1.07720.54640.18310.052*
H3B1.12280.7660.19160.052*
H3C1.02610.67010.02630.052*
C50.7817 (3)0.7122 (2)0.3423 (2)0.0238 (4)
C60.9270 (3)0.6319 (3)0.4617 (2)0.0291 (4)
H61.04860.56960.43770.035*
C70.8968 (3)0.6413 (3)0.6170 (2)0.0351 (4)
H70.99910.58710.69850.042*
C80.7209 (3)0.7282 (3)0.6535 (2)0.0361 (5)
H80.70030.73250.75970.043*
C90.5741 (3)0.8090 (3)0.5359 (2)0.0357 (5)
H90.45160.86910.56050.043*
C100.6057 (3)0.8025 (3)0.3811 (2)0.0300 (4)
H100.50550.86070.30040.036*
O10.7108 (2)0.38422 (18)0.13490 (16)0.0327 (3)
H10.625 (4)0.295 (4)0.075 (3)0.039*
O20.4949 (2)0.5860 (2)0.00660 (17)0.0336 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0271 (8)0.0231 (8)0.0216 (7)0.0008 (6)0.0063 (6)0.0003 (7)
C20.0265 (8)0.0222 (8)0.0254 (8)0.0021 (6)0.0030 (6)0.0001 (7)
C30.0292 (9)0.0409 (12)0.0361 (9)0.0043 (8)0.0104 (7)0.0009 (8)
C50.0237 (8)0.0191 (8)0.0276 (8)0.0035 (7)0.0023 (6)0.0026 (7)
C60.0304 (9)0.0260 (9)0.0296 (9)0.0023 (7)0.0016 (7)0.0003 (8)
C70.0466 (11)0.0268 (9)0.0295 (9)0.0000 (8)0.0009 (8)0.0021 (8)
C80.0500 (11)0.0301 (11)0.0297 (9)0.0063 (9)0.0115 (8)0.0042 (8)
C90.0348 (10)0.0338 (11)0.0403 (10)0.0011 (8)0.0116 (8)0.0078 (9)
C100.0277 (9)0.0272 (10)0.0341 (9)0.0029 (7)0.0031 (7)0.0032 (7)
O10.0349 (7)0.0204 (7)0.0377 (7)0.0020 (5)0.0070 (6)0.0008 (5)
O20.0340 (7)0.0249 (7)0.0361 (6)0.0001 (6)0.0083 (5)0.0006 (5)
Geometric parameters (Å, º) top
C1—O21.206 (2)C6—C71.390 (2)
C1—O11.313 (2)C6—H60.95
C1—C21.505 (2)C7—C81.369 (3)
C2—C51.520 (2)C7—H70.95
C2—C31.523 (2)C8—C91.375 (3)
C2—H21C8—H80.95
C3—H3A0.98C9—C101.388 (3)
C3—H3B0.98C9—H90.95
C3—H3C0.98C10—H100.95
C5—C61.378 (2)O1—H10.93 (3)
C5—C101.389 (2)
O2—C1—O1122.04 (17)C10—C5—C2118.37 (15)
O2—C1—C2124.06 (17)C5—C6—C7120.45 (17)
O1—C1—C2113.90 (15)C5—C6—H6119.8
C1—C2—C5108.68 (13)C7—C6—H6119.8
C1—C2—C3109.80 (15)C8—C7—C6120.57 (18)
C5—C2—C3115.16 (15)C8—C7—H7119.7
C1—C2—H2107.6C6—C7—H7119.7
C5—C2—H2107.6C7—C8—C9119.80 (18)
C3—C2—H2107.6C7—C8—H8120.1
C2—C3—H3A109.5C9—C8—H8120.1
C2—C3—H3B109.5C8—C9—C10119.73 (19)
H3A—C3—H3B109.5C8—C9—H9120.1
C2—C3—H3C109.5C10—C9—H9120.1
H3A—C3—H3C109.5C9—C10—C5120.98 (17)
H3B—C3—H3C109.5C9—C10—H10119.5
C6—C5—C10118.45 (16)C5—C10—H10119.5
C6—C5—C2123.17 (15)C1—O1—H1111.8 (15)
O2—C1—C2—C5110.42 (19)C10—C5—C6—C70.1 (3)
O1—C1—C2—C568.86 (18)C2—C5—C6—C7178.48 (16)
O2—C1—C2—C3122.81 (19)C5—C6—C7—C80.9 (3)
O1—C1—C2—C357.91 (19)C6—C7—C8—C90.9 (3)
C1—C2—C5—C6100.99 (19)C7—C8—C9—C100.2 (3)
C3—C2—C5—C622.6 (2)C8—C9—C10—C51.3 (3)
C1—C2—C5—C1077.62 (19)C6—C5—C10—C91.2 (3)
C3—C2—C5—C10158.75 (17)C2—C5—C10—C9177.45 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.93 (3)1.74 (3)2.643 (2)163 (2)
C2—H2···O2ii1.002.533.482 (2)160
Symmetry codes: (i) x+1, y1/2, z; (ii) x+1, y+1/2, z.
(II) (S)-2-phenylpropionic acid top
Crystal data top
C9H10O2F(000) = 160
Mr = 150.17Dx = 1.268 Mg m3
Monoclinic, P21Melting point = 302–303 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 6.4280 (13) ÅCell parameters from 5429 reflections
b = 7.1935 (14) Åθ = 0.4–28.3°
c = 8.6507 (17) ŵ = 0.09 mm1
β = 100.41 (3)°T = 173 K
V = 393.43 (13) Å3Spheroid, colourless
Z = 20.45 × 0.4 × 0.38 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
676 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
2.0° φ and ω scansθmax = 25.5°, θmin = 3.7°
Absorption correction: multi-scan
SADABS (Sheldrick, 1996)
h = 77
Tmin = 0.963, Tmax = 0.970k = 88
4966 measured reflectionsl = 1010
801 independent 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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.1H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0613P)2 + 0.0318P]
where P = (Fo2 + 2Fc2)/3
801 reflections(Δ/σ)max = 0.004
104 parametersΔρmax = 0.17 e Å3
1 restraintΔρmin = 0.19 e Å3
Special details top

Experimental. absorption corrections were made using the program SADABS (Sheldrick, 1996).

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
C10.3467 (4)0.4456 (4)0.9103 (3)0.0305 (6)
C20.1981 (4)0.2967 (3)0.8299 (3)0.0313 (6)
H20.24680.17470.87880.038*
C30.0265 (5)0.3313 (4)0.8603 (3)0.0421 (7)
H3A0.0760.45310.81810.063*
H3B0.02560.32860.97370.063*
H3C0.12130.23420.80860.063*
C50.2182 (4)0.2879 (3)0.6577 (3)0.0305 (6)
C60.0732 (4)0.3683 (4)0.5385 (3)0.0356 (7)
H60.04740.43030.56270.043*
C70.1034 (5)0.3586 (4)0.3835 (3)0.0404 (8)
H70.0020.41240.30240.048*
C80.2788 (5)0.2718 (4)0.3466 (3)0.0421 (8)
H80.29930.26740.24070.051*
C90.4252 (5)0.1911 (4)0.4643 (3)0.0412 (7)
H90.54730.13180.43970.049*
C100.3927 (5)0.1974 (4)0.6187 (3)0.0361 (7)
H100.49130.13880.6990.043*
O10.2893 (3)0.6159 (2)0.8649 (2)0.0398 (6)
H10.382 (5)0.702 (5)0.927 (4)0.048*
O20.5046 (3)0.4142 (3)1.0067 (2)0.0396 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0375 (16)0.0252 (13)0.0296 (13)0.0017 (11)0.0086 (12)0.0005 (11)
C20.0353 (15)0.0223 (12)0.0358 (14)0.0016 (11)0.0049 (12)0.0002 (11)
C30.0412 (17)0.0417 (17)0.0442 (16)0.0054 (13)0.0095 (13)0.0009 (13)
C50.0363 (15)0.0183 (13)0.0359 (14)0.0036 (12)0.0037 (12)0.0025 (11)
C60.0421 (17)0.0247 (14)0.0388 (15)0.0039 (12)0.0034 (13)0.0016 (12)
C70.0555 (19)0.0270 (14)0.0356 (15)0.0006 (13)0.0000 (14)0.0015 (12)
C80.061 (2)0.0294 (16)0.0384 (15)0.0043 (15)0.0154 (15)0.0053 (13)
C90.0420 (17)0.0349 (17)0.0485 (17)0.0003 (13)0.0126 (14)0.0060 (14)
C100.0353 (16)0.0285 (16)0.0426 (15)0.0004 (12)0.0021 (12)0.0035 (12)
O10.0459 (12)0.0218 (10)0.0463 (12)0.0021 (9)0.0063 (9)0.0002 (9)
O20.0429 (11)0.0258 (10)0.0442 (10)0.0006 (9)0.0077 (9)0.0004 (8)
Geometric parameters (Å, º) top
C1—O21.213 (3)C6—C71.390 (4)
C1—O11.318 (3)C6—H60.95
C1—C21.518 (4)C7—C81.376 (4)
C2—C51.519 (4)C7—H70.95
C2—C31.533 (4)C8—C91.383 (4)
C2—H21C8—H80.95
C3—H3A0.98C9—C101.390 (4)
C3—H3B0.98C9—H90.95
C3—H3C0.98C10—H100.95
C5—C61.386 (4)O1—H10.96 (3)
C5—C101.390 (4)
O2—C1—O1122.2 (3)C10—C5—C2118.2 (2)
O2—C1—C2124.3 (3)C5—C6—C7120.3 (3)
O1—C1—C2113.6 (2)C5—C6—H6119.9
C1—C2—C5108.7 (2)C7—C6—H6119.9
C1—C2—C3109.9 (2)C8—C7—C6120.6 (3)
C5—C2—C3115.1 (2)C8—C7—H7119.7
C1—C2—H2107.6C6—C7—H7119.7
C5—C2—H2107.6C7—C8—C9119.8 (3)
C3—C2—H2107.6C7—C8—H8120.1
C2—C3—H3A109.5C9—C8—H8120.1
C2—C3—H3B109.5C8—C9—C10119.5 (3)
H3A—C3—H3B109.5C8—C9—H9120.2
C2—C3—H3C109.5C10—C9—H9120.2
H3A—C3—H3C109.5C5—C10—C9121.1 (3)
H3B—C3—H3C109.5C5—C10—H10119.4
C6—C5—C10118.6 (2)C9—C10—H10119.4
C6—C5—C2123.2 (2)C1—O1—H1109 (2)
O2—C1—C2—C5110.7 (3)C10—C5—C6—C70.3 (4)
O1—C1—C2—C568.9 (3)C2—C5—C6—C7178.6 (2)
O2—C1—C2—C3122.5 (3)C5—C6—C7—C81.0 (4)
O1—C1—C2—C358.0 (3)C6—C7—C8—C90.9 (4)
C1—C2—C5—C6101.2 (3)C7—C8—C9—C100.5 (5)
C3—C2—C5—C622.6 (4)C6—C5—C10—C91.6 (4)
C1—C2—C5—C1077.6 (3)C2—C5—C10—C9177.2 (3)
C3—C2—C5—C10158.5 (2)C8—C9—C10—C51.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.96 (3)1.74 (4)2.657 (3)159 (3)
C2—H2···O2ii1.002.543.500 (3)160
Symmetry codes: (i) x+1, y+1/2, z+2; (ii) x+1, y1/2, z+2.
(III) (RS)-2-phenylbutyric acid top
Crystal data top
C10H12O2Dx = 1.208 Mg m3
Mr = 164.2Melting point = 312–315 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 11813 reflections
a = 9.1724 (18) Åθ = 0.4–28.3°
b = 7.1850 (14) ŵ = 0.08 mm1
c = 27.407 (6) ÅT = 173 K
V = 1806.2 (6) Å3Block, colourless
Z = 80.4 × 0.32 × 0.2 mm
F(000) = 704
Data collection top
Nonius KappaCCD area-detector
diffractometer
1329 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
0.9° φ and ω scansθmax = 25.5°, θmin = 3.0°
Absorption correction: multi-scan
SADABS (Sheldrick, 1996)
h = 118
Tmin = 0.968, Tmax = 0.984k = 88
9148 measured reflectionsl = 3329
1669 independent 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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0324P)2 + 0.4861P]
where P = (Fo2 + 2Fc2)/3
1669 reflections(Δ/σ)max = 0.001
114 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.14 e Å3
Special details top

Experimental. absorption corrections were made using the program SADABS (Sheldrick, 1996).

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
C10.47389 (15)0.20367 (18)0.54433 (4)0.0325 (3)
C20.45134 (15)0.36459 (17)0.57918 (4)0.0330 (3)
H20.35420.42150.57190.04*
C30.56779 (16)0.51464 (17)0.57210 (5)0.0397 (4)
H3A0.66290.46620.58350.048*
H3B0.57690.5430.53690.048*
C40.53235 (19)0.69257 (19)0.59955 (6)0.0538 (4)
H4A0.43680.73890.58920.081*
H4B0.60690.78650.59250.081*
H4C0.53050.66710.63470.081*
C50.44733 (15)0.28926 (16)0.63121 (4)0.0322 (3)
C60.55964 (17)0.17759 (18)0.64840 (5)0.0410 (4)
H60.63920.14810.62760.049*
C70.5568 (2)0.1088 (2)0.69559 (5)0.0512 (4)
H70.6340.03180.70690.061*
C80.4427 (2)0.1516 (2)0.72612 (5)0.0528 (4)
H80.4410.10460.75850.063*
C90.33069 (19)0.2629 (2)0.70961 (5)0.0485 (4)
H90.25190.29270.73070.058*
C100.33266 (16)0.33182 (18)0.66214 (5)0.0387 (4)
H100.25510.40830.65090.046*
O10.35461 (11)0.11185 (14)0.53405 (4)0.0448 (3)
O20.59328 (11)0.16295 (14)0.52786 (3)0.0442 (3)
H10.382 (2)0.016 (3)0.5101 (7)0.092 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0322 (8)0.0364 (7)0.0288 (6)0.0030 (6)0.0019 (6)0.0066 (5)
C20.0318 (8)0.0318 (6)0.0354 (7)0.0018 (6)0.0027 (6)0.0019 (5)
C30.0405 (8)0.0340 (7)0.0446 (8)0.0033 (6)0.0014 (7)0.0044 (6)
C40.0548 (11)0.0340 (7)0.0725 (11)0.0053 (7)0.0010 (8)0.0029 (7)
C50.0361 (8)0.0277 (6)0.0328 (7)0.0031 (6)0.0018 (6)0.0032 (5)
C60.0457 (9)0.0407 (7)0.0367 (7)0.0057 (7)0.0034 (6)0.0009 (6)
C70.0674 (12)0.0454 (8)0.0408 (8)0.0054 (8)0.0132 (8)0.0032 (6)
C80.0810 (13)0.0465 (8)0.0307 (7)0.0118 (9)0.0040 (8)0.0008 (6)
C90.0617 (11)0.0466 (8)0.0373 (8)0.0114 (8)0.0104 (7)0.0100 (6)
C100.0414 (9)0.0338 (7)0.0407 (8)0.0027 (6)0.0013 (6)0.0067 (6)
O10.0336 (6)0.0514 (6)0.0493 (6)0.0086 (5)0.0030 (5)0.0129 (5)
O20.0334 (6)0.0499 (6)0.0493 (6)0.0058 (5)0.0042 (5)0.0117 (4)
Geometric parameters (Å, º) top
C1—O21.2201 (16)C5—C101.3851 (19)
C1—O11.3083 (16)C5—C61.3881 (19)
C1—C21.5139 (18)C6—C71.385 (2)
C2—C51.5258 (17)C6—H60.95
C2—C31.5300 (18)C7—C81.375 (2)
C2—H21C7—H70.95
C3—C41.5186 (19)C8—C91.378 (2)
C3—H3A0.99C8—H80.95
C3—H3B0.99C9—C101.3922 (19)
C4—H4A0.98C9—H90.95
C4—H4B0.98C10—H100.95
C4—H4C0.98O1—H10.99 (2)
O2—C1—O1123.38 (12)H4B—C4—H4C109.5
O2—C1—C2122.62 (12)C10—C5—C6118.90 (12)
O1—C1—C2114.00 (12)C10—C5—C2120.80 (12)
C1—C2—C5108.79 (10)C6—C5—C2120.30 (12)
C1—C2—C3111.27 (11)C7—C6—C5120.63 (14)
C5—C2—C3112.66 (11)C7—C6—H6119.7
C1—C2—H2108C5—C6—H6119.7
C5—C2—H2108C8—C7—C6120.17 (15)
C3—C2—H2108C8—C7—H7119.9
C4—C3—C2112.39 (12)C6—C7—H7119.9
C4—C3—H3A109.1C7—C8—C9119.84 (14)
C2—C3—H3A109.1C7—C8—H8120.1
C4—C3—H3B109.1C9—C8—H8120.1
C2—C3—H3B109.1C8—C9—C10120.24 (14)
H3A—C3—H3B107.9C8—C9—H9119.9
C3—C4—H4A109.5C10—C9—H9119.9
C3—C4—H4B109.5C5—C10—C9120.22 (14)
H4A—C4—H4B109.5C5—C10—H10119.9
C3—C4—H4C109.5C9—C10—H10119.9
H4A—C4—H4C109.5C1—O1—H1106.7 (12)
O2—C1—C2—C597.82 (14)C3—C2—C5—C670.79 (15)
O1—C1—C2—C581.43 (14)C10—C5—C6—C70.4 (2)
O2—C1—C2—C326.86 (17)C2—C5—C6—C7179.96 (13)
O1—C1—C2—C3153.88 (11)C5—C6—C7—C80.4 (2)
C1—C2—C3—C4169.29 (12)C6—C7—C8—C90.2 (2)
C5—C2—C3—C468.23 (15)C7—C8—C9—C100.1 (2)
C1—C2—C5—C10127.38 (13)C6—C5—C10—C90.14 (19)
C3—C2—C5—C10108.76 (14)C2—C5—C10—C9179.70 (12)
C1—C2—C5—C653.07 (16)C8—C9—C10—C50.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.99 (2)1.67 (2)2.6469 (14)172.1 (19)
Symmetry code: (i) x+1, y, z+1.
(IV) ((RS)-2-phenylpropionic acid).(iso-nicotinamide) top
Crystal data top
C9H10O2·C6H6N2OF(000) = 1152
Mr = 272.3Dx = 1.282 Mg m3
Monoclinic, C2/cMelting point: 364 K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 31.899 (3) ÅCell parameters from 20822 reflections
b = 5.4007 (5) Åθ = 0.4–27.5°
c = 20.8815 (16) ŵ = 0.09 mm1
β = 128.319 (3)°T = 173 K
V = 2822.4 (4) Å3Block, colourless
Z = 80.49 × 0.08 × 0.06 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
1930 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.074
1.5° φ and ω scansθmax = 27.5°, θmin = 3.7°
Absorption correction: integration
Bruker XPREP (Bruker, 1999)
h = 4040
Tmin = 0.961, Tmax = 0.994k = 76
19532 measured reflectionsl = 2725
3204 independent 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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0857P)2]
where P = (Fo2 + 2Fc2)/3
3204 reflections(Δ/σ)max = 0.001
202 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.24 e Å3
Special details top

Experimental. Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 1999).

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*/UeqOcc. (<1)
C10.61761 (7)0.2669 (3)0.90172 (11)0.0385 (4)
C20.64899 (8)0.4338 (3)0.97622 (11)0.0453 (5)
H2A0.6230.51920.98050.054*0.621 (4)
H2B0.67210.5460.97190.054*0.379 (4)
C3A0.68132 (15)0.6336 (6)0.97128 (19)0.0588 (11)0.621 (4)
H3A10.65680.74470.92540.088*0.621 (4)
H3A20.70240.72881.02220.088*0.621 (4)
H3A30.70530.55420.96310.088*0.621 (4)
C3B0.6076 (2)0.5947 (10)0.9749 (3)0.0583 (17)0.379 (4)
H3B10.58430.48630.97810.087*0.379 (4)
H3B20.62670.7081.02160.087*0.379 (4)
H3B30.58590.69050.92410.087*0.379 (4)
C50.68469 (7)0.2700 (3)1.05113 (11)0.0434 (5)
C60.73938 (8)0.2590 (4)1.09397 (12)0.0539 (5)
H60.75560.35921.07730.065*
C70.77084 (9)0.1044 (5)1.16065 (12)0.0631 (6)
H70.80840.10031.18940.076*
C80.74847 (9)0.0432 (4)1.18572 (12)0.0628 (6)
H80.77020.14931.23160.075*
C90.69432 (9)0.0357 (4)1.14376 (13)0.0659 (6)
H90.67840.13841.16030.079*
C100.66273 (9)0.1202 (4)1.07754 (13)0.0580 (6)
H100.62530.1251.04960.07*
O10.64343 (5)0.2103 (3)0.87385 (8)0.0541 (4)
H10.6219 (8)0.077 (4)0.8248 (12)0.065*
O20.57275 (5)0.1904 (3)0.87031 (7)0.0476 (4)
C110.55156 (6)0.5115 (3)0.64484 (9)0.0346 (4)
C120.53463 (8)0.4591 (4)0.69053 (11)0.0494 (5)
H120.50740.55570.68430.059*
C130.55773 (8)0.2655 (4)0.74507 (11)0.0492 (5)
H130.54560.23110.77570.059*
C140.61241 (8)0.1754 (4)0.71302 (12)0.0481 (5)
H140.63980.07630.72060.058*
C150.59129 (7)0.3650 (3)0.65722 (11)0.0432 (5)
H150.60410.3950.62720.052*
C160.52975 (7)0.7187 (3)0.58370 (10)0.0383 (4)
N10.48989 (6)0.8536 (3)0.56910 (10)0.0441 (4)
H1S0.4777 (8)0.980 (4)0.5332 (12)0.053*
H1A0.4760 (8)0.829 (4)0.5929 (11)0.053*
N20.59612 (6)0.1242 (3)0.75713 (9)0.0420 (4)
O30.55010 (5)0.7572 (2)0.54989 (8)0.0507 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0437 (11)0.0359 (10)0.0447 (10)0.0044 (8)0.0318 (9)0.0027 (8)
C20.0530 (12)0.0401 (11)0.0484 (10)0.0016 (9)0.0341 (10)0.0070 (8)
C3A0.078 (3)0.0387 (19)0.0459 (18)0.0033 (17)0.0314 (18)0.0049 (14)
C3B0.072 (4)0.047 (3)0.060 (3)0.003 (3)0.043 (3)0.016 (3)
C50.0505 (11)0.0431 (11)0.0448 (10)0.0000 (9)0.0336 (10)0.0095 (8)
C60.0511 (12)0.0586 (14)0.0549 (12)0.0088 (10)0.0343 (11)0.0058 (10)
C70.0484 (12)0.0767 (16)0.0540 (12)0.0006 (11)0.0267 (11)0.0013 (11)
C80.0672 (15)0.0738 (16)0.0488 (11)0.0115 (12)0.0367 (12)0.0076 (11)
C90.0684 (15)0.0841 (17)0.0654 (13)0.0098 (13)0.0516 (13)0.0171 (12)
C100.0544 (12)0.0741 (15)0.0615 (12)0.0087 (11)0.0438 (11)0.0074 (11)
O10.0505 (8)0.0617 (9)0.0674 (9)0.0189 (7)0.0452 (8)0.0293 (7)
O20.0401 (8)0.0619 (9)0.0475 (7)0.0021 (6)0.0305 (6)0.0011 (6)
C110.0344 (9)0.0366 (10)0.0329 (8)0.0008 (8)0.0209 (8)0.0004 (7)
C120.0518 (12)0.0592 (13)0.0516 (10)0.0207 (10)0.0392 (10)0.0189 (9)
C130.0509 (12)0.0622 (13)0.0481 (11)0.0122 (10)0.0374 (10)0.0151 (9)
C140.0474 (11)0.0468 (12)0.0631 (12)0.0100 (9)0.0406 (11)0.0130 (10)
C150.0463 (11)0.0447 (11)0.0512 (10)0.0047 (9)0.0364 (9)0.0080 (9)
C160.0395 (10)0.0416 (10)0.0371 (9)0.0021 (8)0.0254 (9)0.0030 (8)
N10.0458 (9)0.0495 (10)0.0477 (9)0.0120 (8)0.0343 (8)0.0150 (8)
N20.0376 (8)0.0461 (9)0.0427 (8)0.0025 (7)0.0251 (7)0.0071 (7)
O30.0567 (8)0.0564 (9)0.0590 (8)0.0162 (6)0.0459 (7)0.0203 (6)
Geometric parameters (Å, º) top
C1—O21.219 (2)C8—C91.370 (3)
C1—O11.3059 (19)C8—H80.95
C1—C21.518 (3)C9—C101.382 (3)
C2—C51.522 (3)C9—H90.95
C2—C3A1.540 (4)C10—H100.95
C2—C3B1.567 (6)O1—H11.08 (2)
C2—H2A1C11—C151.375 (2)
C2—H2B1C11—C121.386 (2)
C3A—H2B0.5616C11—C161.505 (2)
C3A—H3A10.98C12—C131.376 (3)
C3A—H3A20.98C12—H120.95
C3A—H3A30.98C13—N21.328 (2)
C3B—H3B10.98C13—H130.95
C3B—H3B20.98C14—N21.337 (2)
C3B—H3B30.98C14—C151.374 (3)
C5—C61.383 (3)C14—H140.95
C5—C101.388 (3)C15—H150.95
C6—C71.382 (3)C16—O31.2375 (19)
C6—H60.95C16—N11.327 (2)
C7—C81.372 (3)N1—H1S0.90 (2)
C7—H70.95N1—H1A0.86 (2)
O2—C1—O1122.37 (16)C8—C7—H7119.6
O2—C1—C2124.13 (15)C6—C7—H7119.6
O1—C1—C2113.49 (15)C9—C8—C7119.1 (2)
C1—C2—C5107.82 (15)C9—C8—H8120.4
C1—C2—C3A113.00 (17)C7—C8—H8120.4
C5—C2—C3A111.8 (2)C8—C9—C10120.4 (2)
C1—C2—C3B107.4 (2)C8—C9—H9119.8
C5—C2—C3B115.2 (2)C10—C9—H9119.8
C3A—C2—C3B101.7 (3)C9—C10—C5121.2 (2)
C1—C2—H2A108C9—C10—H10119.4
C5—C2—H2A108C5—C10—H10119.4
C3A—C2—H2A108C1—O1—H1111.9 (11)
C1—C2—H2B108.8C15—C11—C12117.39 (15)
C5—C2—H2B108.8C15—C11—C16118.33 (14)
C3B—C2—H2B108.8C12—C11—C16124.28 (15)
C2—C3A—H3A1109.5C13—C12—C11119.19 (16)
H2B—C3A—H3A1115.2C13—C12—H12120.4
C2—C3A—H3A2109.5C11—C12—H12120.4
H2B—C3A—H3A2115.8N2—C13—C12123.47 (16)
C2—C3A—H3A3109.5N2—C13—H13118.3
H2B—C3A—H3A396.6C12—C13—H13118.3
C2—C3B—H3B1109.5N2—C14—C15122.86 (17)
C2—C3B—H3B2109.5N2—C14—H14118.6
H3B1—C3B—H3B2109.5C15—C14—H14118.6
C2—C3B—H3B3109.5C14—C15—C11119.90 (16)
H3B1—C3B—H3B3109.5C14—C15—H15120.1
H3B2—C3B—H3B3109.5C11—C15—H15120.1
C6—C5—C10117.58 (19)O3—C16—N1122.92 (16)
C6—C5—C2121.96 (17)O3—C16—C11118.61 (15)
C10—C5—C2120.44 (18)N1—C16—C11118.47 (15)
C7—C6—C5120.93 (19)C16—N1—H1S117.7 (12)
C7—C6—H6119.5C16—N1—H1A123.3 (14)
C5—C6—H6119.5H1S—N1—H1A119.0 (19)
C8—C7—C6120.7 (2)C13—N2—C14117.20 (15)
O2—C1—C2—C594.7 (2)C7—C8—C9—C100.6 (3)
O1—C1—C2—C584.95 (19)C8—C9—C10—C50.9 (3)
O2—C1—C2—C3A141.3 (2)C6—C5—C10—C90.6 (3)
O1—C1—C2—C3A39.1 (3)C2—C5—C10—C9177.82 (18)
O2—C1—C2—C3B30.0 (3)C15—C11—C12—C130.3 (3)
O1—C1—C2—C3B150.4 (3)C16—C11—C12—C13179.61 (17)
C1—C2—C5—C6107.39 (19)C11—C12—C13—N20.4 (3)
C3A—C2—C5—C617.4 (3)N2—C14—C15—C110.1 (3)
C3B—C2—C5—C6132.8 (3)C12—C11—C15—C140.1 (3)
C1—C2—C5—C1070.9 (2)C16—C11—C15—C14179.51 (17)
C3A—C2—C5—C10164.3 (2)C15—C11—C16—O33.5 (2)
C3B—C2—C5—C1048.9 (3)C12—C11—C16—O3175.80 (17)
C10—C5—C6—C70.1 (3)C15—C11—C16—N1177.20 (17)
C2—C5—C6—C7178.42 (18)C12—C11—C16—N13.5 (3)
C5—C6—C7—C80.4 (3)C12—C13—N2—C140.3 (3)
C6—C7—C8—C90.0 (3)C15—C14—N2—C130.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N21.08 (2)1.55 (2)2.631 (2)175 (2)
N1—H1S···O3i0.90 (2)1.98 (2)2.879 (2)177 (2)
N1—H1A···O2ii0.86 (2)2.12 (2)2.964 (2)167 (2)
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+1, y+1, z+3/2.
(V) ((R)-2-phenylpropionic acid).(iso-nicotinamide) top
Crystal data top
C9H10O2·C6H6N2OF(000) = 1152
Mr = 272.3Dx = 1.27 Mg m3
Monoclinic, C2Melting point: 360 K
Hall symbol: C 2yMo Kα radiation, λ = 0.71073 Å
a = 32.006 (2) ÅCell parameters from 21845 reflections
b = 5.4698 (4) Åθ = 1–28.3°
c = 20.8451 (10) ŵ = 0.09 mm1
β = 128.690 (3)°T = 173 K
V = 2848.4 (3) Å3Plate, colourless
Z = 80.38 × 0.15 × 0.03 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
2254 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.072
2.0° φ and ω scansθmax = 28.0°, θmin = 1.3°
Absorption correction: integration
Bruker XPREP (Bruker, 1999)
h = 4239
Tmin = 0.973, Tmax = 0.997k = 77
21632 measured reflectionsl = 2727
3784 independent 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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0587P)2 + 0.0245P]
where P = (Fo2 + 2Fc2)/3
3784 reflections(Δ/σ)max = 0.001
380 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.28 e Å3
Special details top

Experimental. Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 1999).

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
C1A0.61768 (12)0.3452 (9)1.14879 (17)0.0307 (8)
C2A0.64893 (13)0.5225 (9)1.22036 (17)0.0361 (9)
H2A0.67110.62871.21290.043*
C3A0.61174 (14)0.6868 (9)1.2238 (2)0.0519 (10)
H3A10.58840.58541.22820.078*
H3A20.63320.79451.27180.078*
H3A30.58990.78591.17370.078*
C5A0.68656 (13)0.3754 (10)1.29905 (18)0.0361 (8)
C6A0.74102 (13)0.3651 (10)1.33889 (19)0.0466 (10)
H6A0.75520.45571.31760.056*
C7A0.77517 (15)0.2258 (11)1.4090 (2)0.0540 (10)
H7A0.81230.22011.4350.065*
C8A0.75527 (14)0.0953 (10)1.44124 (19)0.0486 (10)
H8A0.77860.00131.48980.058*
C9A0.70121 (14)0.1020 (10)1.40238 (18)0.0465 (10)
H9A0.68720.0111.42390.056*
C10A0.66737 (14)0.2404 (10)1.33236 (19)0.0398 (9)
H10A0.63020.24371.30630.048*
O1A0.64482 (9)0.2758 (8)1.12384 (13)0.0464 (7)
H1A0.6240 (13)0.153 (8)1.0793 (19)0.056*
O2A0.57279 (8)0.2705 (8)1.11774 (11)0.0359 (6)
C1B0.38415 (13)2.1759 (9)0.34686 (18)0.0330 (8)
C2B0.35274 (13)2.3342 (10)0.26988 (17)0.0401 (9)
H2B0.37892.41080.26470.048*
C3B0.32344 (16)2.5389 (10)0.2766 (2)0.0599 (11)
H3B10.29922.46860.28530.09*
H3B20.30282.6350.22570.09*
H3B30.34952.6450.3230.09*
C5B0.31642 (13)2.1665 (8)0.19631 (17)0.0331 (8)
C6B0.26221 (13)2.1551 (9)0.15475 (18)0.0439 (9)
H6B0.24632.2560.17120.053*
C7B0.23050 (14)1.9958 (10)0.0884 (2)0.0516 (10)
H7B0.19291.99050.05940.062*
C8B0.25335 (15)1.8464 (10)0.06486 (19)0.0493 (10)
H8B0.23161.7380.01970.059*
C9B0.30771 (13)1.8546 (10)0.10681 (18)0.0454 (9)
H9B0.32361.75080.0910.054*
C10B0.33913 (14)2.0139 (10)0.17207 (18)0.0421 (9)
H10B0.37662.01930.20070.051*
O1B0.35785 (8)2.1233 (8)0.37419 (12)0.0378 (6)
H1B0.3767 (12)1.997 (7)0.4220 (17)0.045*
O2B0.42915 (9)2.1016 (9)0.37963 (12)0.0454 (7)
C11A0.55096 (12)0.4412 (9)0.89403 (17)0.0303 (8)
C12A0.53557 (13)0.3932 (10)0.94211 (18)0.0396 (9)
H12A0.50940.49170.93770.048*
C13A0.55914 (13)0.1995 (10)0.99634 (18)0.0405 (9)
H13A0.5480.16631.02830.049*
C14A0.61086 (13)0.1045 (10)0.96029 (18)0.0384 (8)
H14A0.63750.00430.96660.046*
C15A0.58925 (12)0.2918 (9)0.90374 (17)0.0356 (8)
H15A0.60060.31790.87170.043*
C16A0.52861 (13)0.6466 (10)0.83209 (17)0.0323 (8)
N1A0.48951 (11)0.7829 (8)0.81860 (15)0.0356 (7)
H1AS0.4708 (11)0.919 (7)0.7695 (17)0.043*
H1AA0.4744 (12)0.757 (7)0.8418 (17)0.043*
N2A0.59638 (10)0.0566 (9)1.00663 (15)0.0358 (7)
O3A0.54818 (8)0.6831 (8)0.79701 (12)0.0429 (6)
C11B0.44883 (12)1.4143 (9)0.60505 (16)0.0288 (7)
C12B0.46707 (13)1.4695 (10)0.56214 (19)0.0458 (10)
H12B0.49511.37670.57010.055*
C13B0.44411 (14)1.6618 (10)0.5072 (2)0.0482 (10)
H13B0.45721.69860.4780.058*
C14B0.38684 (13)1.7415 (10)0.53397 (18)0.0404 (9)
H14B0.35831.83460.52410.048*
C15B0.40811 (13)1.5528 (10)0.59034 (18)0.0389 (9)
H15B0.39441.51950.61880.047*
C16B0.47000 (12)1.2063 (9)0.66554 (17)0.0319 (8)
N1B0.50995 (11)1.0747 (9)0.68074 (15)0.0367 (7)
H1BS0.5220 (13)0.954 (7)0.7141 (19)0.044*
H1BA0.5277 (12)1.101 (7)0.6577 (16)0.044*
N2B0.40484 (10)1.7978 (9)0.49295 (14)0.0342 (7)
O3B0.44947 (9)1.1679 (8)0.69884 (13)0.0472 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0326 (19)0.0313 (19)0.0277 (15)0.0010 (16)0.0185 (15)0.0011 (15)
C2A0.043 (2)0.031 (2)0.0346 (17)0.0057 (16)0.0238 (16)0.0045 (15)
C3A0.064 (2)0.037 (2)0.0502 (18)0.0009 (19)0.0335 (18)0.0094 (17)
C5A0.038 (2)0.0346 (19)0.0362 (17)0.0065 (16)0.0235 (15)0.0109 (16)
C6A0.042 (2)0.055 (2)0.0440 (18)0.0080 (19)0.0274 (17)0.0043 (19)
C7A0.041 (2)0.065 (3)0.051 (2)0.002 (2)0.0265 (18)0.007 (2)
C8A0.050 (2)0.051 (2)0.0421 (19)0.002 (2)0.0276 (18)0.0009 (19)
C9A0.053 (2)0.054 (2)0.0421 (18)0.009 (2)0.0343 (17)0.0043 (18)
C10A0.0395 (19)0.044 (2)0.0406 (17)0.0047 (17)0.0274 (16)0.0062 (17)
O1A0.0406 (15)0.0589 (19)0.0490 (14)0.0149 (15)0.0325 (13)0.0263 (15)
O2A0.0325 (13)0.0407 (14)0.0380 (12)0.0031 (12)0.0239 (10)0.0047 (11)
C1B0.038 (2)0.034 (2)0.0336 (17)0.0105 (17)0.0259 (16)0.0057 (16)
C2B0.051 (2)0.037 (2)0.0343 (17)0.0096 (18)0.0278 (17)0.0021 (16)
C3B0.087 (3)0.0314 (19)0.0427 (18)0.004 (2)0.0319 (19)0.0036 (17)
C5B0.041 (2)0.0306 (18)0.0296 (15)0.0035 (16)0.0233 (15)0.0040 (15)
C6B0.042 (2)0.044 (2)0.0443 (18)0.0021 (18)0.0265 (17)0.0015 (18)
C7B0.035 (2)0.062 (3)0.047 (2)0.0044 (19)0.0203 (17)0.002 (2)
C8B0.056 (2)0.051 (3)0.0367 (17)0.011 (2)0.0266 (17)0.0089 (17)
C9B0.050 (2)0.053 (2)0.0419 (18)0.0021 (19)0.0335 (17)0.0049 (18)
C10B0.0383 (19)0.058 (2)0.0340 (16)0.0027 (18)0.0246 (15)0.0022 (18)
O1B0.0378 (14)0.0423 (15)0.0410 (12)0.0081 (12)0.0284 (12)0.0116 (13)
O2B0.0339 (14)0.0674 (18)0.0387 (12)0.0029 (14)0.0246 (11)0.0012 (13)
C11A0.0289 (18)0.033 (2)0.0272 (15)0.0030 (16)0.0168 (14)0.0024 (15)
C12A0.041 (2)0.046 (2)0.0412 (17)0.0086 (19)0.0303 (16)0.0050 (18)
C13A0.041 (2)0.051 (2)0.0337 (16)0.0082 (19)0.0251 (16)0.0125 (18)
C14A0.036 (2)0.040 (2)0.0482 (19)0.0042 (18)0.0302 (17)0.0038 (19)
C15A0.042 (2)0.037 (2)0.0385 (17)0.0002 (18)0.0300 (16)0.0019 (17)
C16A0.0322 (19)0.036 (2)0.0312 (16)0.0008 (16)0.0209 (15)0.0038 (16)
N1A0.0366 (17)0.0383 (18)0.0377 (15)0.0030 (15)0.0260 (13)0.0045 (15)
N2A0.0354 (17)0.0377 (17)0.0363 (14)0.0028 (15)0.0233 (14)0.0060 (14)
O3A0.0480 (15)0.0476 (16)0.0490 (13)0.0101 (13)0.0382 (12)0.0144 (13)
C11B0.0268 (18)0.0323 (18)0.0276 (15)0.0016 (16)0.0171 (14)0.0025 (15)
C12B0.043 (2)0.060 (3)0.0479 (19)0.020 (2)0.0355 (17)0.020 (2)
C13B0.046 (2)0.063 (3)0.055 (2)0.017 (2)0.0408 (19)0.021 (2)
C14B0.041 (2)0.045 (2)0.0453 (19)0.0118 (19)0.0321 (18)0.0130 (19)
C15B0.045 (2)0.040 (2)0.047 (2)0.0094 (19)0.0360 (18)0.0096 (19)
C16B0.0335 (19)0.035 (2)0.0288 (16)0.0005 (17)0.0204 (16)0.0005 (15)
N1B0.0375 (18)0.0399 (18)0.0399 (16)0.0116 (15)0.0278 (15)0.0131 (15)
N2B0.0304 (16)0.0399 (17)0.0310 (13)0.0027 (15)0.0186 (13)0.0049 (14)
O3B0.0552 (16)0.0534 (17)0.0552 (14)0.0211 (14)0.0454 (13)0.0226 (14)
Geometric parameters (Å, º) top
C1A—O2A1.220 (3)C8B—C9B1.375 (4)
C1A—O1A1.317 (4)C8B—H8B0.95
C1A—C2A1.517 (4)C9B—C10B1.382 (5)
C2A—C5A1.523 (4)C9B—H9B0.95
C2A—C3A1.529 (5)C10B—H10B0.95
C2A—H2A1O1B—H1B1.04 (3)
C3A—H3A10.98C11A—C15A1.378 (4)
C3A—H3A20.98C11A—C12A1.390 (4)
C3A—H3A30.98C11A—C16A1.512 (5)
C5A—C6A1.386 (4)C12A—C13A1.380 (5)
C5A—C10A1.392 (5)C12A—H12A0.95
C6A—C7A1.384 (5)C13A—N2A1.326 (4)
C6A—H6A0.95C13A—H13A0.95
C7A—C8A1.378 (5)C14A—N2A1.333 (4)
C7A—H7A0.95C14A—C15A1.378 (5)
C8A—C9A1.378 (5)C14A—H14A0.95
C8A—H8A0.95C15A—H15A0.95
C9A—C10A1.378 (5)C16A—O3A1.241 (3)
C9A—H9A0.95C16A—N1A1.327 (4)
C10A—H10A0.95N1A—H1AS1.09 (3)
O1A—H1A0.99 (4)N1A—H1AA0.88 (3)
C1B—O2B1.215 (4)C11B—C15B1.367 (4)
C1B—O1B1.310 (3)C11B—C12B1.373 (4)
C1B—C2B1.523 (4)C11B—C16B1.508 (5)
C2B—C5B1.522 (4)C12B—C13B1.381 (5)
C2B—C3B1.522 (5)C12B—H12B0.95
C2B—H2B1C13B—N2B1.325 (4)
C3B—H3B10.98C13B—H13B0.95
C3B—H3B20.98C14B—N2B1.332 (4)
C3B—H3B30.98C14B—C15B1.381 (5)
C5B—C6B1.373 (4)C14B—H14B0.95
C5B—C10B1.393 (5)C15B—H15B0.95
C6B—C7B1.395 (5)C16B—O3B1.236 (3)
C6B—H6B0.95C16B—N1B1.322 (4)
C7B—C8B1.376 (5)N1B—H1BS0.86 (4)
C7B—H7B0.95N1B—H1BA0.96 (3)
O2A—C1A—O1A122.9 (3)C8B—C7B—H7B119.8
O2A—C1A—C2A124.8 (3)C6B—C7B—H7B119.8
O1A—C1A—C2A112.4 (3)C9B—C8B—C7B119.8 (3)
C1A—C2A—C5A108.2 (3)C9B—C8B—H8B120.1
C1A—C2A—C3A111.6 (3)C7B—C8B—H8B120.1
C5A—C2A—C3A112.0 (2)C8B—C9B—C10B120.0 (3)
C1A—C2A—H2A108.3C8B—C9B—H9B120
C5A—C2A—H2A108.3C10B—C9B—H9B120
C3A—C2A—H2A108.3C9B—C10B—C5B120.7 (3)
C2A—C3A—H3A1109.5C9B—C10B—H10B119.6
C2A—C3A—H3A2109.5C5B—C10B—H10B119.6
H3A1—C3A—H3A2109.5C1B—O1B—H1B114.7 (17)
C2A—C3A—H3A3109.5C15A—C11A—C12A117.8 (3)
H3A1—C3A—H3A3109.5C15A—C11A—C16A117.9 (3)
H3A2—C3A—H3A3109.5C12A—C11A—C16A124.3 (3)
C6A—C5A—C10A117.5 (3)C13A—C12A—C11A118.5 (3)
C6A—C5A—C2A121.2 (3)C13A—C12A—H12A120.8
C10A—C5A—C2A121.3 (3)C11A—C12A—H12A120.8
C7A—C6A—C5A121.5 (3)N2A—C13A—C12A124.1 (3)
C7A—C6A—H6A119.3N2A—C13A—H13A117.9
C5A—C6A—H6A119.3C12A—C13A—H13A117.9
C8A—C7A—C6A120.0 (4)N2A—C14A—C15A123.4 (3)
C8A—C7A—H7A120N2A—C14A—H14A118.3
C6A—C7A—H7A120C15A—C14A—H14A118.3
C9A—C8A—C7A119.5 (3)C14A—C15A—C11A119.4 (3)
C9A—C8A—H8A120.2C14A—C15A—H15A120.3
C7A—C8A—H8A120.2C11A—C15A—H15A120.3
C8A—C9A—C10A120.3 (3)O3A—C16A—N1A122.8 (3)
C8A—C9A—H9A119.9O3A—C16A—C11A118.6 (3)
C10A—C9A—H9A119.9N1A—C16A—C11A118.6 (3)
C9A—C10A—C5A121.3 (3)C16A—N1A—H1AS118.2 (16)
C9A—C10A—H10A119.3C16A—N1A—H1AA124 (2)
C5A—C10A—H10A119.3H1AS—N1A—H1AA117 (3)
C1A—O1A—H1A109.9 (19)C13A—N2A—C14A116.8 (3)
O2B—C1B—O1B122.7 (3)C15B—C11B—C12B117.8 (3)
O2B—C1B—C2B123.5 (3)C15B—C11B—C16B118.2 (3)
O1B—C1B—C2B113.8 (3)C12B—C11B—C16B124.0 (3)
C5B—C2B—C3B114.2 (3)C11B—C12B—C13B119.0 (3)
C5B—C2B—C1B107.7 (3)C11B—C12B—H12B120.5
C3B—C2B—C1B111.1 (2)C13B—C12B—H12B120.5
C5B—C2B—H2B107.9N2B—C13B—C12B123.5 (3)
C3B—C2B—H2B107.9N2B—C13B—H13B118.2
C1B—C2B—H2B107.9C12B—C13B—H13B118.2
C2B—C3B—H3B1109.5N2B—C14B—C15B122.5 (3)
C2B—C3B—H3B2109.5N2B—C14B—H14B118.7
H3B1—C3B—H3B2109.5C15B—C14B—H14B118.7
C2B—C3B—H3B3109.5C11B—C15B—C14B119.9 (3)
H3B1—C3B—H3B3109.5C11B—C15B—H15B120
H3B2—C3B—H3B3109.5C14B—C15B—H15B120
C6B—C5B—C10B118.9 (3)O3B—C16B—N1B123.2 (3)
C6B—C5B—C2B122.1 (3)O3B—C16B—C11B118.6 (3)
C10B—C5B—C2B118.9 (3)N1B—C16B—C11B118.2 (3)
C5B—C6B—C7B120.2 (3)C16B—N1B—H1BS119 (2)
C5B—C6B—H6B119.9C16B—N1B—H1BA126 (2)
C7B—C6B—H6B119.9H1BS—N1B—H1BA115 (3)
C8B—C7B—C6B120.3 (4)C13B—N2B—C14B117.2 (3)
O2A—C1A—C2A—C5A96.8 (4)C7B—C8B—C9B—C10B0.5 (5)
O1A—C1A—C2A—C5A82.2 (3)C8B—C9B—C10B—C5B0.3 (5)
O2A—C1A—C2A—C3A26.9 (5)C6B—C5B—C10B—C9B0.5 (5)
O1A—C1A—C2A—C3A154.1 (3)C2B—C5B—C10B—C9B178.4 (3)
C1A—C2A—C5A—C6A105.0 (4)C15A—C11A—C12A—C13A0.3 (5)
C3A—C2A—C5A—C6A131.6 (3)C16A—C11A—C12A—C13A180.0 (3)
C1A—C2A—C5A—C10A73.1 (4)C11A—C12A—C13A—N2A1.0 (6)
C3A—C2A—C5A—C10A50.4 (4)N2A—C14A—C15A—C11A0.6 (5)
C10A—C5A—C6A—C7A0.1 (5)C12A—C11A—C15A—C14A0.5 (5)
C2A—C5A—C6A—C7A178.0 (3)C16A—C11A—C15A—C14A179.3 (3)
C5A—C6A—C7A—C8A0.7 (6)C15A—C11A—C16A—O3A5.0 (5)
C6A—C7A—C8A—C9A0.9 (6)C12A—C11A—C16A—O3A174.7 (3)
C7A—C8A—C9A—C10A0.7 (6)C15A—C11A—C16A—N1A176.1 (3)
C8A—C9A—C10A—C5A0.2 (5)C12A—C11A—C16A—N1A4.1 (5)
C6A—C5A—C10A—C9A0.1 (5)C12A—C13A—N2A—C14A0.9 (5)
C2A—C5A—C10A—C9A178.3 (3)C15A—C14A—N2A—C13A0.1 (5)
O2B—C1B—C2B—C5B96.3 (4)C15B—C11B—C12B—C13B0.6 (5)
O1B—C1B—C2B—C5B82.7 (3)C16B—C11B—C12B—C13B178.9 (3)
O2B—C1B—C2B—C3B137.9 (4)C11B—C12B—C13B—N2B0.2 (6)
O1B—C1B—C2B—C3B43.1 (4)C12B—C11B—C15B—C14B0.1 (5)
C3B—C2B—C5B—C6B18.2 (4)C16B—C11B—C15B—C14B178.5 (3)
C1B—C2B—C5B—C6B105.7 (3)N2B—C14B—C15B—C11B0.7 (5)
C3B—C2B—C5B—C10B164.0 (3)C15B—C11B—C16B—O3B0.6 (5)
C1B—C2B—C5B—C10B72.1 (3)C12B—C11B—C16B—O3B177.7 (3)
C10B—C5B—C6B—C7B1.1 (5)C15B—C11B—C16B—N1B178.9 (3)
C2B—C5B—C6B—C7B179.0 (3)C12B—C11B—C16B—N1B2.8 (5)
C5B—C6B—C7B—C8B0.9 (5)C12B—C13B—N2B—C14B0.6 (6)
C6B—C7B—C8B—C9B0.1 (6)C15B—C14B—N2B—C13B1.1 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A···N2A0.99 (4)1.65 (4)2.635 (4)173 (3)
O1B—H1B···N2B1.04 (3)1.59 (4)2.628 (3)178 (3)
N1A—H1AS···O3B1.09 (3)1.80 (3)2.883 (4)171 (3)
N1A—H1AA···O2Ai0.88 (3)2.15 (3)3.022 (3)171 (3)
N1B—H1BS···O3A0.86 (4)2.02 (4)2.873 (4)175 (3)
N1B—H1BA···O2Bii0.96 (3)1.97 (3)2.911 (3)170 (3)
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+1, y1, z+1.
(VII) ((RS)-2-phenylbutyric acid).(iso-nicotinamide) top
Crystal data top
C10H12O2·C6H6N2OZ = 2
Mr = 286.32F(000) = 304
Triclinic, P1Dx = 1.313 Mg m3
Hall symbol: -P 1Melting point: 377 K
a = 5.7543 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.6867 (8) ÅCell parameters from 12733 reflections
c = 13.7434 (12) Åθ = 0.4–28.7°
α = 102.056 (5)°µ = 0.09 mm1
β = 93.206 (4)°T = 173 K
γ = 103.524 (5)°Block, colourless
V = 723.95 (11) Å30.4 × 0.16 × 0.13 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
2674 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.061
2.0° φ and ω scansθmax = 28.0°, θmin = 3.0°
Absorption correction: integration
Bruker XPREP (Bruker, 1999)
h = 76
Tmin = 0.970, Tmax = 0.994k = 1212
12417 measured reflectionsl = 1818
3488 independent 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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0588P)2 + 0.1607P]
where P = (Fo2 + 2Fc2)/3
3488 reflections(Δ/σ)max < 0.001
200 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.21 e Å3
Special details top

Experimental. Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 1999).

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
C11.0993 (2)1.27176 (13)0.27501 (9)0.0223 (3)
C21.2119 (2)1.37726 (13)0.21221 (9)0.0230 (3)
H21.12041.4540.21750.028*
C31.4736 (2)1.45377 (14)0.25103 (10)0.0272 (3)
H3A1.48341.50260.32260.033*
H3B1.56861.380.24610.033*
C41.5827 (3)1.56634 (15)0.19302 (11)0.0341 (3)
H4A1.5761.51830.12230.051*
H4B1.75061.61210.22040.051*
H4C1.49191.6410.1990.051*
C51.1762 (2)1.29438 (13)0.10261 (9)0.0233 (3)
C61.0000 (3)1.31167 (16)0.03669 (10)0.0314 (3)
H60.90411.37680.05970.038*
C70.9617 (3)1.23514 (17)0.06253 (11)0.0370 (3)
H70.83971.2480.10680.044*
C81.1004 (3)1.14029 (16)0.09719 (11)0.0335 (3)
H81.07451.0880.16510.04*
C91.2771 (3)1.12223 (16)0.03219 (11)0.0358 (3)
H91.37281.05710.05550.043*
C101.3155 (3)1.19900 (15)0.06721 (10)0.0312 (3)
H101.43791.18620.11130.037*
O10.86748 (17)1.21733 (11)0.24787 (7)0.0296 (2)
H10.802 (3)1.1491 (19)0.2822 (13)0.036*
O21.20778 (18)1.23927 (11)0.34169 (8)0.0349 (3)
C110.3800 (2)0.78402 (13)0.41102 (9)0.0205 (3)
C120.6229 (2)0.84249 (14)0.44203 (10)0.0247 (3)
H120.70310.80730.49030.03*
C130.7465 (2)0.95373 (14)0.40092 (10)0.0262 (3)
H130.91310.99340.42220.031*
C140.4102 (2)0.94987 (14)0.30258 (10)0.0258 (3)
H140.33520.98670.25380.031*
C150.2726 (2)0.83796 (14)0.33904 (9)0.0243 (3)
H150.10710.79870.31510.029*
C160.2221 (2)0.66348 (13)0.44988 (9)0.0235 (3)
N10.3105 (2)0.62706 (13)0.52944 (9)0.0286 (3)
H1S0.209 (3)0.5544 (18)0.5524 (12)0.034*
H1A0.453 (3)0.6752 (18)0.5621 (12)0.034*
N20.6436 (2)1.00800 (12)0.33303 (8)0.0244 (3)
O30.01871 (18)0.60392 (11)0.40584 (8)0.0366 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0244 (6)0.0228 (6)0.0194 (6)0.0056 (5)0.0022 (5)0.0042 (5)
C20.0245 (7)0.0223 (6)0.0237 (6)0.0059 (5)0.0027 (5)0.0085 (5)
C30.0279 (7)0.0243 (6)0.0272 (7)0.0032 (5)0.0007 (5)0.0051 (5)
C40.0336 (8)0.0282 (7)0.0365 (8)0.0010 (6)0.0052 (6)0.0082 (6)
C50.0237 (6)0.0222 (6)0.0233 (6)0.0005 (5)0.0038 (5)0.0092 (5)
C60.0302 (7)0.0373 (8)0.0282 (7)0.0115 (6)0.0028 (6)0.0074 (6)
C70.0351 (8)0.0486 (9)0.0265 (7)0.0116 (7)0.0042 (6)0.0081 (6)
C80.0382 (8)0.0360 (7)0.0215 (6)0.0029 (6)0.0036 (6)0.0032 (6)
C90.0421 (9)0.0332 (8)0.0340 (8)0.0141 (7)0.0071 (6)0.0058 (6)
C100.0350 (8)0.0324 (7)0.0282 (7)0.0109 (6)0.0004 (6)0.0093 (6)
O10.0241 (5)0.0355 (5)0.0311 (5)0.0015 (4)0.0022 (4)0.0184 (4)
O20.0305 (5)0.0406 (6)0.0348 (6)0.0028 (4)0.0040 (4)0.0200 (5)
C110.0226 (6)0.0195 (6)0.0183 (6)0.0036 (5)0.0030 (5)0.0034 (5)
C120.0226 (6)0.0280 (6)0.0232 (6)0.0039 (5)0.0004 (5)0.0087 (5)
C130.0214 (6)0.0304 (7)0.0249 (7)0.0014 (5)0.0011 (5)0.0081 (5)
C140.0291 (7)0.0253 (6)0.0228 (6)0.0050 (5)0.0009 (5)0.0082 (5)
C150.0225 (6)0.0244 (6)0.0241 (6)0.0025 (5)0.0012 (5)0.0059 (5)
C160.0238 (7)0.0226 (6)0.0228 (6)0.0025 (5)0.0019 (5)0.0064 (5)
N10.0260 (6)0.0297 (6)0.0279 (6)0.0027 (5)0.0020 (5)0.0143 (5)
N20.0262 (6)0.0241 (5)0.0212 (5)0.0021 (4)0.0024 (4)0.0061 (4)
O30.0267 (5)0.0411 (6)0.0378 (6)0.0078 (4)0.0074 (4)0.0209 (5)
Geometric parameters (Å, º) top
C1—O21.2153 (15)C9—C101.390 (2)
C1—O11.3152 (16)C9—H90.95
C1—C21.5265 (17)C10—H100.95
C2—C31.5248 (18)O1—H10.914 (19)
C2—C51.5294 (17)C11—C121.3853 (18)
C2—H21C11—C151.3900 (17)
C3—C41.5224 (19)C11—C161.5143 (17)
C3—H3A0.99C12—C131.3880 (18)
C3—H3B0.99C12—H120.95
C4—H4A0.98C13—N21.3365 (17)
C4—H4B0.98C13—H130.95
C4—H4C0.98C14—N21.3342 (17)
C5—C61.3843 (19)C14—C151.3869 (18)
C5—C101.3912 (19)C14—H140.95
C6—C71.388 (2)C15—H150.95
C6—H60.95C16—O31.2359 (16)
C7—C81.382 (2)C16—N11.3275 (17)
C7—H70.95N1—H1S0.925 (18)
C8—C91.382 (2)N1—H1A0.886 (18)
C8—H80.95
O2—C1—O1123.06 (12)C9—C8—H8120.3
O2—C1—C2125.04 (12)C7—C8—H8120.3
O1—C1—C2111.90 (10)C8—C9—C10120.31 (13)
C3—C2—C1112.04 (10)C8—C9—H9119.8
C3—C2—C5113.61 (11)C10—C9—H9119.8
C1—C2—C5108.45 (10)C9—C10—C5120.52 (13)
C3—C2—H2107.5C9—C10—H10119.7
C1—C2—H2107.5C5—C10—H10119.7
C5—C2—H2107.5C1—O1—H1112.0 (10)
C4—C3—C2112.43 (11)C12—C11—C15118.41 (11)
C4—C3—H3A109.1C12—C11—C16124.27 (11)
C2—C3—H3A109.1C15—C11—C16117.32 (11)
C4—C3—H3B109.1C11—C12—C13118.42 (12)
C2—C3—H3B109.1C11—C12—H12120.8
H3A—C3—H3B107.8C13—C12—H12120.8
C3—C4—H4A109.5N2—C13—C12123.54 (12)
C3—C4—H4B109.5N2—C13—H13118.2
H4A—C4—H4B109.5C12—C13—H13118.2
C3—C4—H4C109.5N2—C14—C15122.82 (12)
H4A—C4—H4C109.5N2—C14—H14118.6
H4B—C4—H4C109.5C15—C14—H14118.6
C6—C5—C10118.60 (12)C14—C15—C11119.10 (12)
C6—C5—C2120.08 (12)C14—C15—H15120.5
C10—C5—C2121.31 (11)C11—C15—H15120.5
C5—C6—C7120.91 (13)O3—C16—N1123.52 (12)
C5—C6—H6119.5O3—C16—C11118.48 (11)
C7—C6—H6119.5N1—C16—C11118.00 (11)
C8—C7—C6120.20 (13)C16—N1—H1S116.2 (10)
C8—C7—H7119.9C16—N1—H1A121.8 (11)
C6—C7—H7119.9H1S—N1—H1A121.7 (14)
C9—C8—C7119.46 (13)C14—N2—C13117.69 (11)
O2—C1—C2—C37.26 (18)C8—C9—C10—C50.3 (2)
O1—C1—C2—C3173.45 (10)C6—C5—C10—C90.4 (2)
O2—C1—C2—C5118.94 (14)C2—C5—C10—C9178.63 (12)
O1—C1—C2—C560.35 (13)C15—C11—C12—C131.03 (18)
C1—C2—C3—C4176.32 (11)C16—C11—C12—C13179.45 (12)
C5—C2—C3—C460.34 (14)C11—C12—C13—N20.2 (2)
C3—C2—C5—C6131.88 (13)N2—C14—C15—C110.6 (2)
C1—C2—C5—C6102.84 (14)C12—C11—C15—C141.37 (18)
C3—C2—C5—C1049.13 (16)C16—C11—C15—C14179.07 (11)
C1—C2—C5—C1076.15 (15)C12—C11—C16—O3168.58 (12)
C10—C5—C6—C70.3 (2)C15—C11—C16—O310.94 (18)
C2—C5—C6—C7178.67 (13)C12—C11—C16—N111.12 (19)
C5—C6—C7—C80.2 (2)C15—C11—C16—N1169.35 (12)
C6—C7—C8—C90.1 (2)C15—C14—N2—C130.63 (19)
C7—C8—C9—C100.1 (2)C12—C13—N2—C141.00 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N20.91 (2)1.75 (2)2.661 (2)172 (2)
N1—H1S···O3i0.93 (2)1.98 (2)2.902 (2)177 (2)
N1—H1A···O2ii0.89 (2)2.18 (2)3.051 (2)169 (2)
Symmetry codes: (i) x, y+1, z+1; (ii) x+2, y+2, z+1.
(VIII) ((R)-2-phenylbutyric acid).(iso-nicotinamide) top
Crystal data top
C10H12O2·C6H6N2OZ = 2
Mr = 286.32F(000) = 304
Triclinic, P1Dx = 1.299 Mg m3
Hall symbol: P 1Melting point: 361 K
a = 5.6984 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.7762 (10) ÅCell parameters from 18331 reflections
c = 13.8553 (13) Åθ = 0.4–28.3°
α = 100.011 (3)°µ = 0.09 mm1
β = 94.302 (5)°T = 173 K
γ = 103.919 (5)°Plate, colourless
V = 732.26 (11) Å30.21 × 0.09 × 0.03 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
2350 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.073
2.0° φ and ω scansθmax = 28°, θmin = 2.2°
Absorption correction: integration
Bruker XPREP (Bruker, 1999)
h = 77
Tmin = 0.983, Tmax = 0.997k = 1212
18175 measured reflectionsl = 1818
3541 independent 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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.057P)2]
where P = (Fo2 + 2Fc2)/3
3541 reflections(Δ/σ)max = 0.001
399 parametersΔρmax = 0.18 e Å3
3 restraintsΔρmin = 0.22 e Å3
Special details top

Experimental. Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 1999).

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
C1A1.8863 (6)1.4248 (4)0.2156 (2)0.0315 (7)
C2A2.0644 (6)1.4978 (4)0.1523 (2)0.0348 (7)
H2A2.22491.47920.17130.042*
C3A2.0990 (7)1.6594 (4)0.1803 (3)0.0443 (8)
H3A12.13431.68990.2530.053*
H3A21.94571.68290.15960.053*
C4A2.3071 (8)1.7438 (4)0.1324 (3)0.0550 (10)
H4A12.46091.72480.15540.082*
H4A22.31941.84690.1510.082*
H4A32.27381.71350.06040.082*
C5A1.9964 (5)1.4355 (3)0.0422 (2)0.0315 (7)
C6A1.8067 (6)1.4643 (4)0.0140 (3)0.0386 (8)
H6A1.71691.52680.0160.046*
C7A1.7493 (6)1.4026 (4)0.1128 (3)0.0420 (9)
H7A1.62021.42270.15060.05*
C8A1.8781 (6)1.3117 (4)0.1570 (3)0.0410 (9)
H8A1.83621.26820.2250.049*
C9A2.0674 (7)1.2838 (4)0.1029 (3)0.0436 (9)
H9A2.15751.22190.13350.052*
C10A2.1261 (6)1.3460 (4)0.0039 (3)0.0390 (8)
H10A2.25771.32690.03310.047*
O1A1.6596 (4)1.3758 (3)0.17604 (18)0.0434 (6)
H1A1.564 (7)1.323 (4)0.218 (3)0.052*
O2A1.9539 (4)1.4127 (3)0.29776 (19)0.0510 (7)
C1B0.3343 (5)0.0976 (3)0.6660 (2)0.0280 (7)
C2B0.4460 (5)0.2040 (3)0.7276 (2)0.0273 (7)
H2B0.35230.27880.72340.033*
C3B0.7118 (5)0.2808 (3)0.6887 (2)0.0310 (7)
H3B10.72250.32620.61830.037*
H3B20.80920.20920.6930.037*
C4B0.8200 (6)0.3959 (4)0.7464 (3)0.0411 (8)
H4B10.72180.46590.74390.062*
H4B20.98740.44510.7170.062*
H4B30.820.35060.81530.062*
C5B0.4123 (5)0.1273 (3)0.8348 (2)0.0270 (7)
C6B0.2392 (6)0.1479 (4)0.9032 (2)0.0368 (8)
H6B0.14350.21260.88310.044*
C7B0.2048 (6)0.0748 (4)1.0007 (3)0.0447 (9)
H7B0.08480.08941.04640.054*
C8B0.3421 (6)0.0181 (4)1.0318 (3)0.0390 (9)
H8B0.31810.06781.09850.047*
C9B0.5164 (6)0.0387 (4)0.9644 (3)0.0405 (9)
H9B0.61220.1030.98510.049*
C10B0.5517 (6)0.0340 (4)0.8673 (2)0.0352 (8)
H10B0.67330.01970.82220.042*
O1B0.0987 (4)0.0435 (2)0.69316 (17)0.0348 (6)
H1B0.025 (6)0.029 (4)0.657 (3)0.042*
O2B0.4458 (4)0.0612 (3)0.60057 (18)0.0397 (6)
C11A1.1220 (5)0.9745 (3)0.3541 (2)0.0254 (7)
C12A1.3681 (5)1.0364 (3)0.3871 (2)0.0319 (7)
H12A1.44831.00560.43870.038*
C13A1.4926 (6)1.1435 (4)0.3429 (2)0.0335 (8)
H13A1.65971.18630.36630.04*
C14A1.1582 (6)1.1285 (3)0.2371 (2)0.0332 (8)
H14A1.08421.15950.18410.04*
C15A1.0182 (6)1.0222 (3)0.2765 (2)0.0330 (8)
H15A0.85170.98150.2510.04*
C16A0.9634 (6)0.8573 (3)0.3957 (2)0.0294 (7)
N1A1.0613 (5)0.8149 (3)0.4720 (2)0.0360 (7)
H1AS0.981 (7)0.741 (4)0.493 (3)0.043*
H1AA1.225 (7)0.857 (4)0.506 (3)0.043*
N2A1.3926 (5)1.1908 (3)0.26920 (19)0.0321 (6)
O3A0.7502 (4)0.8062 (3)0.35843 (18)0.0440 (6)
C11B0.3813 (5)0.3986 (3)0.5332 (2)0.0255 (7)
C12B0.1338 (5)0.3394 (3)0.5038 (2)0.0317 (7)
H12B0.04810.37670.45760.038*
C13B0.0148 (6)0.2252 (4)0.5431 (3)0.0335 (8)
H13B0.15380.1840.52170.04*
C14B0.3601 (6)0.2292 (4)0.6391 (3)0.0339 (8)
H14B0.440.19190.68720.041*
C15B0.4937 (5)0.3423 (3)0.6029 (2)0.0307 (7)
H15B0.6620.38140.62580.037*
C16B0.5336 (6)0.5214 (4)0.4951 (2)0.0308 (7)
N1B0.4400 (5)0.5591 (3)0.4165 (2)0.0378 (7)
H1BS0.548 (7)0.629 (4)0.397 (3)0.045*
H1BA0.305 (7)0.513 (4)0.389 (3)0.045*
N2B0.1236 (5)0.1696 (3)0.60956 (19)0.0312 (6)
O3B0.7383 (4)0.5835 (3)0.53946 (17)0.0419 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0290 (16)0.0338 (18)0.0277 (19)0.0002 (14)0.0011 (14)0.0076 (15)
C2A0.0305 (16)0.0373 (19)0.0347 (18)0.0043 (13)0.0051 (13)0.0078 (15)
C3A0.048 (2)0.040 (2)0.041 (2)0.0044 (16)0.0116 (16)0.0058 (16)
C4A0.057 (2)0.041 (2)0.061 (3)0.0044 (19)0.016 (2)0.015 (2)
C5A0.0288 (16)0.0328 (18)0.0292 (17)0.0021 (14)0.0036 (13)0.0103 (14)
C6A0.0353 (18)0.043 (2)0.040 (2)0.0120 (15)0.0084 (15)0.0104 (16)
C7A0.0316 (18)0.059 (2)0.035 (2)0.0074 (17)0.0020 (14)0.0168 (18)
C8A0.036 (2)0.051 (2)0.030 (2)0.0002 (17)0.0022 (15)0.0096 (17)
C9A0.045 (2)0.046 (2)0.040 (2)0.0140 (17)0.0023 (16)0.0072 (17)
C10A0.0377 (18)0.042 (2)0.038 (2)0.0094 (16)0.0019 (15)0.0104 (16)
O1A0.0283 (13)0.0601 (16)0.0366 (14)0.0068 (11)0.0026 (10)0.0242 (12)
O2A0.0396 (13)0.0676 (18)0.0390 (15)0.0047 (13)0.0075 (11)0.0236 (13)
C1B0.0300 (17)0.0276 (18)0.0267 (17)0.0077 (14)0.0032 (13)0.0055 (14)
C2B0.0227 (14)0.0286 (17)0.0302 (17)0.0034 (13)0.0005 (12)0.0104 (13)
C3B0.0248 (15)0.0291 (17)0.0368 (17)0.0020 (12)0.0020 (12)0.0077 (14)
C4B0.0349 (18)0.038 (2)0.044 (2)0.0024 (15)0.0031 (15)0.0088 (16)
C5B0.0258 (15)0.0256 (16)0.0290 (17)0.0015 (12)0.0036 (12)0.0109 (13)
C6B0.0332 (17)0.045 (2)0.0336 (19)0.0131 (15)0.0019 (14)0.0086 (16)
C7B0.0357 (18)0.063 (2)0.034 (2)0.0126 (18)0.0056 (15)0.0113 (18)
C8B0.042 (2)0.040 (2)0.030 (2)0.0018 (17)0.0027 (16)0.0053 (16)
C9B0.045 (2)0.040 (2)0.038 (2)0.0139 (17)0.0074 (16)0.0075 (16)
C10B0.0383 (19)0.0369 (19)0.0312 (19)0.0109 (15)0.0006 (14)0.0096 (15)
O1B0.0245 (11)0.0415 (14)0.0382 (14)0.0005 (10)0.0028 (10)0.0189 (11)
O2B0.0333 (12)0.0463 (15)0.0399 (13)0.0033 (11)0.0022 (10)0.0220 (11)
C11A0.0292 (16)0.0227 (16)0.0239 (16)0.0060 (13)0.0042 (13)0.0041 (13)
C12A0.0274 (16)0.0336 (18)0.0320 (18)0.0037 (14)0.0025 (13)0.0077 (15)
C13A0.0281 (17)0.040 (2)0.0287 (18)0.0010 (15)0.0007 (13)0.0093 (15)
C14A0.0339 (18)0.0310 (18)0.0316 (19)0.0004 (15)0.0025 (14)0.0118 (15)
C15A0.0283 (17)0.0349 (19)0.0316 (18)0.0013 (15)0.0032 (13)0.0081 (15)
C16A0.0250 (16)0.0300 (17)0.0298 (17)0.0004 (13)0.0018 (13)0.0082 (14)
N1A0.0326 (16)0.0371 (17)0.0361 (17)0.0007 (14)0.0015 (13)0.0169 (14)
N2A0.0314 (14)0.0347 (16)0.0266 (15)0.0004 (13)0.0020 (11)0.0081 (12)
O3A0.0292 (12)0.0492 (15)0.0481 (15)0.0069 (11)0.0058 (11)0.0235 (12)
C11B0.0244 (16)0.0259 (16)0.0236 (16)0.0023 (14)0.0042 (12)0.0035 (13)
C12B0.0292 (17)0.0362 (19)0.0297 (18)0.0055 (14)0.0020 (13)0.0114 (15)
C13B0.0226 (16)0.0377 (19)0.037 (2)0.0008 (15)0.0013 (14)0.0087 (15)
C14B0.0280 (17)0.0349 (19)0.0368 (19)0.0038 (15)0.0008 (14)0.0102 (15)
C15B0.0231 (15)0.0304 (18)0.0362 (19)0.0027 (14)0.0005 (13)0.0079 (15)
C16B0.0274 (17)0.0319 (18)0.0325 (18)0.0042 (14)0.0042 (14)0.0094 (14)
N1B0.0264 (15)0.0417 (18)0.0391 (18)0.0080 (13)0.0039 (13)0.0181 (15)
N2B0.0306 (15)0.0337 (15)0.0277 (15)0.0034 (12)0.0032 (11)0.0085 (12)
O3B0.0303 (12)0.0459 (14)0.0424 (14)0.0082 (11)0.0059 (10)0.0198 (11)
Geometric parameters (Å, º) top
C1A—O2A1.208 (4)C6B—H6B0.95
C1A—O1A1.305 (4)C7B—C8B1.371 (5)
C1A—C2A1.520 (5)C7B—H7B0.95
C2A—C3A1.520 (5)C8B—C9B1.385 (5)
C2A—C5A1.525 (5)C8B—H8B0.95
C2A—H2A1C9B—C10B1.383 (5)
C3A—C4A1.538 (5)C9B—H9B0.95
C3A—H3A10.99C10B—H10B0.95
C3A—H3A20.99O1B—H1B0.97 (4)
C4A—H4A10.98C11A—C15A1.391 (4)
C4A—H4A20.98C11A—C12A1.393 (4)
C4A—H4A30.98C11A—C16A1.507 (4)
C5A—C10A1.382 (4)C12A—C13A1.381 (5)
C5A—C6A1.396 (4)C12A—H12A0.95
C6A—C7A1.376 (5)C13A—N2A1.335 (4)
C6A—H6A0.95C13A—H13A0.95
C7A—C8A1.377 (5)C14A—N2A1.334 (4)
C7A—H7A0.95C14A—C15A1.370 (5)
C8A—C9A1.376 (5)C14A—H14A0.95
C8A—H8A0.95C15A—H15A0.95
C9A—C10A1.380 (5)C16A—O3A1.232 (4)
C9A—H9A0.95C16A—N1A1.332 (4)
C10A—H10A0.95N1A—H1AS0.87 (4)
O1A—H1A0.95 (4)N1A—H1AA0.97 (4)
C1B—O2B1.219 (4)C11B—C15B1.381 (4)
C1B—O1B1.318 (4)C11B—C12B1.389 (4)
C1B—C2B1.512 (4)C11B—C16B1.503 (5)
C2B—C5B1.518 (4)C12B—C13B1.380 (5)
C2B—C3B1.529 (4)C12B—H12B0.95
C2B—H2B1C13B—N2B1.334 (4)
C3B—C4B1.529 (5)C13B—H13B0.95
C3B—H3B10.99C14B—N2B1.334 (4)
C3B—H3B20.99C14B—C15B1.378 (5)
C4B—H4B10.98C14B—H14B0.95
C4B—H4B20.98C15B—H15B0.95
C4B—H4B30.98C16B—O3B1.236 (4)
C5B—C10B1.388 (4)C16B—N1B1.323 (4)
C5B—C6B1.390 (4)N1B—H1BS0.89 (4)
C6B—C7B1.390 (5)N1B—H1BA0.82 (4)
O2A—C1A—O1A122.5 (3)C10B—C5B—C2B121.2 (3)
O2A—C1A—C2A121.1 (3)C6B—C5B—C2B120.8 (3)
O1A—C1A—C2A116.3 (3)C5B—C6B—C7B120.7 (3)
C3A—C2A—C1A108.8 (3)C5B—C6B—H6B119.7
C3A—C2A—C5A114.5 (3)C7B—C6B—H6B119.7
C1A—C2A—C5A113.2 (3)C8B—C7B—C6B120.8 (3)
C3A—C2A—H2A106.6C8B—C7B—H7B119.6
C1A—C2A—H2A106.6C6B—C7B—H7B119.6
C5A—C2A—H2A106.6C7B—C8B—C9B119.1 (3)
C2A—C3A—C4A112.4 (3)C7B—C8B—H8B120.5
C2A—C3A—H3A1109.1C9B—C8B—H8B120.5
C4A—C3A—H3A1109.1C10B—C9B—C8B120.4 (3)
C2A—C3A—H3A2109.1C10B—C9B—H9B119.8
C4A—C3A—H3A2109.1C8B—C9B—H9B119.8
H3A1—C3A—H3A2107.9C9B—C10B—C5B121.1 (3)
C3A—C4A—H4A1109.5C9B—C10B—H10B119.5
C3A—C4A—H4A2109.5C5B—C10B—H10B119.5
H4A1—C4A—H4A2109.5C1B—O1B—H1B113 (2)
C3A—C4A—H4A3109.5C15A—C11A—C12A117.7 (3)
H4A1—C4A—H4A3109.5C15A—C11A—C16A118.2 (3)
H4A2—C4A—H4A3109.5C12A—C11A—C16A124.1 (3)
C10A—C5A—C6A118.5 (3)C13A—C12A—C11A118.4 (3)
C10A—C5A—C2A118.8 (3)C13A—C12A—H12A120.8
C6A—C5A—C2A122.7 (3)C11A—C12A—H12A120.8
C7A—C6A—C5A120.3 (3)N2A—C13A—C12A124.1 (3)
C7A—C6A—H6A119.9N2A—C13A—H13A118
C5A—C6A—H6A119.9C12A—C13A—H13A118
C6A—C7A—C8A120.3 (3)N2A—C14A—C15A123.6 (3)
C6A—C7A—H7A119.8N2A—C14A—H14A118.2
C8A—C7A—H7A119.8C15A—C14A—H14A118.2
C9A—C8A—C7A120.0 (4)C14A—C15A—C11A119.4 (3)
C9A—C8A—H8A120C14A—C15A—H15A120.3
C7A—C8A—H8A120C11A—C15A—H15A120.3
C8A—C9A—C10A119.8 (3)O3A—C16A—N1A123.2 (3)
C8A—C9A—H9A120.1O3A—C16A—C11A118.8 (3)
C10A—C9A—H9A120.1N1A—C16A—C11A118.0 (3)
C9A—C10A—C5A121.0 (3)C16A—N1A—H1AS120 (3)
C9A—C10A—H10A119.5C16A—N1A—H1AA125 (2)
C5A—C10A—H10A119.5H1AS—N1A—H1AA114 (3)
C1A—O1A—H1A111 (2)C14A—N2A—C13A116.9 (3)
O2B—C1B—O1B122.8 (3)C15B—C11B—C12B117.8 (3)
O2B—C1B—C2B125.2 (3)C15B—C11B—C16B118.0 (3)
O1B—C1B—C2B112.0 (2)C12B—C11B—C16B124.2 (3)
C1B—C2B—C5B108.9 (2)C13B—C12B—C11B118.7 (3)
C1B—C2B—C3B112.3 (2)C13B—C12B—H12B120.6
C5B—C2B—C3B112.9 (2)C11B—C12B—H12B120.6
C1B—C2B—H2B107.5N2B—C13B—C12B123.5 (3)
C5B—C2B—H2B107.5N2B—C13B—H13B118.2
C3B—C2B—H2B107.5C12B—C13B—H13B118.2
C2B—C3B—C4B112.4 (3)N2B—C14B—C15B122.9 (3)
C2B—C3B—H3B1109.1N2B—C14B—H14B118.6
C4B—C3B—H3B1109.1C15B—C14B—H14B118.6
C2B—C3B—H3B2109.1C14B—C15B—C11B119.6 (3)
C4B—C3B—H3B2109.1C14B—C15B—H15B120.2
H3B1—C3B—H3B2107.8C11B—C15B—H15B120.2
C3B—C4B—H4B1109.5O3B—C16B—N1B123.3 (3)
C3B—C4B—H4B2109.5O3B—C16B—C11B118.5 (3)
H4B1—C4B—H4B2109.5N1B—C16B—C11B118.2 (3)
C3B—C4B—H4B3109.5C16B—N1B—H1BS112 (2)
H4B1—C4B—H4B3109.5C16B—N1B—H1BA119 (3)
H4B2—C4B—H4B3109.5H1BS—N1B—H1BA129 (4)
C10B—C5B—C6B118.0 (3)C13B—N2B—C14B117.4 (3)
O2A—C1A—C2A—C3A83.7 (4)C5B—C6B—C7B—C8B0.6 (5)
O1A—C1A—C2A—C3A96.7 (3)C6B—C7B—C8B—C9B0.1 (6)
O2A—C1A—C2A—C5A147.8 (3)C7B—C8B—C9B—C10B0.2 (6)
O1A—C1A—C2A—C5A31.7 (4)C8B—C9B—C10B—C5B0.8 (5)
C1A—C2A—C3A—C4A170.6 (3)C6B—C5B—C10B—C9B1.3 (5)
C5A—C2A—C3A—C4A61.6 (4)C2B—C5B—C10B—C9B178.3 (3)
C3A—C2A—C5A—C10A130.3 (3)C15A—C11A—C12A—C13A1.7 (4)
C1A—C2A—C5A—C10A104.2 (3)C16A—C11A—C12A—C13A179.7 (3)
C3A—C2A—C5A—C6A50.3 (4)C11A—C12A—C13A—N2A0.9 (5)
C1A—C2A—C5A—C6A75.2 (4)N2A—C14A—C15A—C11A0.1 (5)
C10A—C5A—C6A—C7A1.0 (5)C12A—C11A—C15A—C14A1.2 (4)
C2A—C5A—C6A—C7A178.5 (3)C16A—C11A—C15A—C14A179.9 (3)
C5A—C6A—C7A—C8A0.1 (5)C15A—C11A—C16A—O3A1.5 (4)
C6A—C7A—C8A—C9A0.9 (6)C12A—C11A—C16A—O3A177.1 (3)
C7A—C8A—C9A—C10A0.7 (6)C15A—C11A—C16A—N1A178.0 (3)
C8A—C9A—C10A—C5A0.4 (6)C12A—C11A—C16A—N1A3.4 (4)
C6A—C5A—C10A—C9A1.2 (5)C15A—C14A—N2A—C13A0.9 (5)
C2A—C5A—C10A—C9A178.2 (3)C12A—C13A—N2A—C14A0.4 (5)
O2B—C1B—C2B—C5B116.9 (3)C15B—C11B—C12B—C13B2.0 (4)
O1B—C1B—C2B—C5B61.1 (3)C16B—C11B—C12B—C13B179.0 (3)
O2B—C1B—C2B—C3B8.9 (4)C11B—C12B—C13B—N2B1.2 (5)
O1B—C1B—C2B—C3B173.0 (3)N2B—C14B—C15B—C11B0.2 (5)
C1B—C2B—C3B—C4B176.0 (3)C12B—C11B—C15B—C14B1.3 (4)
C5B—C2B—C3B—C4B60.4 (3)C16B—C11B—C15B—C14B179.6 (3)
C1B—C2B—C5B—C10B74.6 (3)C15B—C11B—C16B—O3B12.8 (4)
C3B—C2B—C5B—C10B50.8 (4)C12B—C11B—C16B—O3B166.2 (3)
C1B—C2B—C5B—C6B105.0 (3)C15B—C11B—C16B—N1B168.2 (3)
C3B—C2B—C5B—C6B129.6 (3)C12B—C11B—C16B—N1B12.8 (5)
C10B—C5B—C6B—C7B1.2 (5)C12B—C13B—N2B—C14B0.3 (5)
C2B—C5B—C6B—C7B178.4 (3)C15B—C14B—N2B—C13B1.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A···N2A0.95 (4)1.72 (4)2.653 (4)165 (4)
O1B—H1B···N2B0.97 (4)1.69 (4)2.661 (4)172 (3)
N1A—H1AS···O3B0.87 (4)2.03 (4)2.893 (4)169 (3)
N1A—H1AA···O2Bi0.97 (4)2.10 (4)3.065 (4)171 (3)
N1B—H1BS···O3A0.89 (4)2.02 (4)2.905 (4)170 (3)
N1B—H1BA···O2Aii0.82 (4)2.20 (4)3.003 (4)170 (4)
Symmetry codes: (i) x+2, y+1, z; (ii) x2, y1, z.
(IX) ((S)-2-phenylbutyric acid).(iso-nicotinamide) top
Crystal data top
C10H12O2·C6H6N2OZ = 2
Mr = 286.32F(000) = 304
Triclinic, P1Dx = 1.3 Mg m3
Hall symbol: P 1Melting point: 361 K
a = 5.7059 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.7727 (4) ÅCell parameters from 18951 reflections
c = 13.8321 (7) Åθ = 0.4–28.3°
α = 100.323 (3)°µ = 0.09 mm1
β = 94.090 (2)°T = 173 K
γ = 103.881 (3)°Block, colourless
V = 731.36 (6) Å30.47 × 0.2 × 0.09 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
3151 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.068
2.0° φ and ω scansθmax = 28°, θmin = 3.4°
Absorption correction: integration
Bruker XPREP (Bruker, 1999)
h = 77
Tmin = 0.953, Tmax = 0.992k = 1212
18714 measured reflectionsl = 1818
3529 independent 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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.1071P)2 + 0.108P]
where P = (Fo2 + 2Fc2)/3
3529 reflections(Δ/σ)max < 0.001
399 parametersΔρmax = 0.78 e Å3
3 restraintsΔρmin = 0.27 e Å3
Special details top

Experimental. Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 1999).

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
C1A0.8824 (6)0.4274 (3)0.7841 (2)0.0321 (6)
C2A1.0648 (6)0.4973 (4)0.8485 (2)0.0384 (7)
H2A1.2240.47710.83010.046*
C3A1.0988 (8)0.6603 (4)0.8191 (3)0.0473 (8)
H3A10.94670.68450.84020.057*
H3A21.13330.69090.74620.057*
C4A1.3115 (9)0.7427 (4)0.8679 (3)0.0532 (10)
H4A11.46290.72120.84540.08*
H4A21.27740.71240.94010.08*
H4A31.32810.84650.8490.08*
C5A0.9925 (6)0.4372 (3)0.9583 (2)0.0357 (7)
C6A0.8009 (6)0.4654 (4)1.0146 (3)0.0412 (7)
H6A0.70960.52710.98410.049*
C7A0.7454 (6)0.4032 (4)1.1143 (2)0.0386 (7)
H7A0.61820.42351.1530.046*
C8A0.8763 (6)0.3116 (4)1.1571 (2)0.0374 (7)
H8A0.83550.26681.22510.045*
C9A1.0637 (7)0.2844 (4)1.1031 (3)0.0434 (8)
H9A1.15390.22231.13380.052*
C10A1.1220 (7)0.3473 (4)1.0036 (3)0.0417 (7)
H10A1.25260.32830.96630.05*
O1A0.6557 (4)0.3786 (3)0.82201 (17)0.0418 (6)
H1A0.575 (9)0.321 (5)0.787 (3)0.05*
O2A0.9572 (5)0.4127 (3)0.70373 (19)0.0487 (6)
C1B1.3344 (5)1.0972 (3)0.3337 (2)0.0256 (5)
C2B1.4471 (4)1.2045 (3)0.27201 (19)0.0222 (5)
H2B1.35381.27950.27650.027*
C3B1.7133 (5)1.2811 (3)0.3114 (2)0.0267 (5)
H3B11.72371.32720.3820.032*
H3B21.81051.20930.30710.032*
C4B1.8195 (6)1.3951 (3)0.2532 (2)0.0364 (7)
H4B11.72411.46660.25760.055*
H4B21.81431.34930.18370.055*
H4B31.98851.44270.28080.055*
C5B1.4123 (5)1.1266 (3)0.16454 (19)0.0246 (5)
C6B1.2391 (5)1.1464 (4)0.0965 (2)0.0336 (6)
H6B1.14341.21110.11720.04*
C7B1.2031 (6)1.0727 (4)0.0019 (2)0.0421 (7)
H7B1.08251.08670.04740.051*
C8B1.3420 (6)0.9802 (4)0.0328 (2)0.0370 (7)
H8B1.31840.93060.09990.044*
C9B1.5170 (6)0.9592 (4)0.0338 (2)0.0370 (7)
H9B1.61220.89450.01260.044*
C10B1.5533 (6)1.0330 (3)0.1318 (2)0.0315 (6)
H10B1.67541.01950.17690.038*
O1B1.1004 (4)1.0436 (2)0.30739 (16)0.0317 (5)
H1B1.027 (7)1.006 (4)0.349 (3)0.038*
O2B1.4456 (4)1.0613 (3)0.39959 (17)0.0369 (5)
C11A0.1255 (5)0.0271 (3)0.64573 (19)0.0233 (5)
C12A0.3707 (5)0.0339 (3)0.6133 (2)0.0293 (6)
H12A0.45110.00240.56230.035*
C13A0.4955 (5)0.1424 (3)0.6572 (2)0.0311 (6)
H13A0.66260.18480.63430.037*
C14A0.1609 (5)0.1288 (3)0.7625 (2)0.0300 (6)
H14A0.0880.15970.81570.036*
C15A0.0189 (5)0.0212 (3)0.7223 (2)0.0296 (6)
H15A0.14810.01870.74670.035*
C16A0.0339 (5)0.1445 (3)0.6047 (2)0.0285 (6)
N1A0.0632 (5)0.1866 (3)0.52813 (19)0.0316 (5)
H1AS0.011 (8)0.252 (5)0.510 (3)0.038*
H1AA0.232 (8)0.146 (4)0.494 (3)0.038*
N2A0.3938 (5)0.1903 (3)0.72990 (18)0.0295 (5)
O3A0.2463 (4)0.1961 (3)0.64189 (18)0.0438 (6)
C11B0.6188 (5)0.6023 (3)0.4671 (2)0.0240 (5)
C12B0.8660 (5)0.6611 (3)0.4972 (2)0.0286 (6)
H12B0.95030.62420.5440.034*
C13B0.9860 (5)0.7747 (3)0.4572 (2)0.0300 (6)
H13B1.15460.81530.47820.036*
C14B0.6413 (5)0.7719 (3)0.3611 (2)0.0293 (6)
H14B0.56210.81020.31370.035*
C15B0.5056 (5)0.6572 (3)0.3968 (2)0.0283 (6)
H15B0.33820.61720.37330.034*
C16B0.4643 (5)0.4784 (3)0.5048 (2)0.0268 (5)
N1B0.5576 (5)0.4426 (3)0.5847 (2)0.0340 (6)
H1BS0.437 (8)0.380 (5)0.604 (3)0.041*
H1BA0.688 (8)0.492 (5)0.616 (3)0.041*
N2B0.8772 (4)0.8304 (2)0.39062 (17)0.0268 (5)
O3B0.2612 (4)0.4178 (3)0.46077 (17)0.0379 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0328 (14)0.0333 (14)0.0243 (13)0.0019 (12)0.0004 (11)0.0061 (11)
C2A0.0366 (15)0.0417 (16)0.0352 (15)0.0070 (13)0.0046 (12)0.0073 (13)
C3A0.056 (2)0.0348 (16)0.0444 (19)0.0001 (15)0.0120 (16)0.0049 (13)
C4A0.067 (3)0.0344 (17)0.050 (2)0.0063 (17)0.0145 (19)0.0100 (15)
C5A0.0360 (16)0.0381 (16)0.0249 (13)0.0085 (13)0.0027 (11)0.0104 (12)
C6A0.0394 (17)0.0480 (19)0.0329 (16)0.0054 (14)0.0076 (13)0.0065 (13)
C7A0.0322 (15)0.0533 (18)0.0300 (15)0.0094 (14)0.0009 (12)0.0116 (13)
C8A0.0369 (16)0.0439 (17)0.0264 (14)0.0021 (14)0.0015 (12)0.0068 (12)
C9A0.0450 (19)0.0452 (18)0.0390 (17)0.0114 (15)0.0021 (14)0.0076 (14)
C10A0.0410 (18)0.0429 (17)0.0383 (17)0.0029 (14)0.0047 (13)0.0151 (14)
O1A0.0354 (12)0.0535 (14)0.0302 (12)0.0079 (10)0.0049 (9)0.0218 (10)
O2A0.0363 (13)0.0617 (16)0.0392 (13)0.0079 (11)0.0094 (10)0.0207 (11)
C1B0.0295 (14)0.0232 (12)0.0243 (12)0.0061 (11)0.0031 (10)0.0062 (10)
C2B0.0203 (11)0.0219 (11)0.0225 (11)0.0002 (9)0.0005 (9)0.0074 (9)
C3B0.0224 (12)0.0273 (12)0.0273 (12)0.0001 (10)0.0011 (9)0.0077 (10)
C4B0.0353 (16)0.0308 (14)0.0367 (16)0.0054 (12)0.0041 (12)0.0095 (12)
C5B0.0246 (12)0.0230 (11)0.0241 (12)0.0004 (10)0.0011 (10)0.0081 (10)
C6B0.0298 (14)0.0437 (16)0.0272 (14)0.0109 (12)0.0014 (11)0.0065 (12)
C7B0.0388 (16)0.056 (2)0.0301 (16)0.0136 (15)0.0063 (13)0.0062 (14)
C8B0.0400 (17)0.0381 (16)0.0268 (14)0.0011 (13)0.0013 (12)0.0037 (12)
C9B0.0461 (18)0.0327 (15)0.0329 (16)0.0136 (13)0.0061 (13)0.0034 (12)
C10B0.0351 (15)0.0332 (14)0.0268 (13)0.0109 (12)0.0023 (11)0.0068 (11)
O1B0.0244 (10)0.0380 (11)0.0337 (11)0.0017 (8)0.0018 (8)0.0189 (9)
O2B0.0324 (11)0.0428 (12)0.0356 (11)0.0035 (9)0.0045 (8)0.0201 (9)
C11A0.0241 (13)0.0241 (12)0.0193 (12)0.0024 (10)0.0020 (9)0.0035 (9)
C12A0.0263 (14)0.0322 (14)0.0270 (14)0.0026 (11)0.0012 (11)0.0078 (11)
C13A0.0249 (14)0.0359 (15)0.0271 (14)0.0029 (11)0.0003 (11)0.0082 (11)
C14A0.0324 (15)0.0289 (13)0.0248 (13)0.0011 (12)0.0026 (11)0.0070 (11)
C15A0.0259 (13)0.0294 (14)0.0290 (14)0.0012 (11)0.0020 (11)0.0080 (11)
C16A0.0262 (13)0.0270 (13)0.0278 (13)0.0028 (10)0.0006 (10)0.0076 (10)
N1A0.0294 (13)0.0325 (12)0.0292 (13)0.0039 (10)0.0028 (10)0.0150 (10)
N2A0.0315 (13)0.0309 (12)0.0235 (11)0.0019 (10)0.0030 (9)0.0071 (9)
O3A0.0291 (11)0.0505 (14)0.0450 (13)0.0098 (10)0.0087 (10)0.0247 (11)
C11B0.0253 (14)0.0232 (12)0.0228 (12)0.0050 (10)0.0038 (10)0.0046 (10)
C12B0.0251 (13)0.0340 (15)0.0258 (13)0.0033 (11)0.0008 (10)0.0105 (11)
C13B0.0223 (13)0.0351 (14)0.0294 (14)0.0005 (11)0.0003 (10)0.0088 (11)
C14B0.0302 (14)0.0286 (13)0.0286 (14)0.0047 (11)0.0017 (11)0.0103 (11)
C15B0.0220 (12)0.0300 (14)0.0296 (14)0.0012 (11)0.0029 (10)0.0072 (11)
C16B0.0262 (13)0.0259 (12)0.0270 (13)0.0021 (10)0.0021 (10)0.0083 (10)
N1B0.0295 (13)0.0337 (13)0.0343 (14)0.0049 (11)0.0033 (11)0.0158 (11)
N2B0.0292 (12)0.0257 (11)0.0228 (11)0.0012 (9)0.0015 (9)0.0064 (9)
O3B0.0297 (11)0.0399 (11)0.0375 (12)0.0074 (9)0.0066 (9)0.0173 (9)
Geometric parameters (Å, º) top
C1A—O2A1.208 (4)C6B—H6B0.95
C1A—O1A1.301 (4)C7B—C8B1.372 (5)
C1A—C2A1.533 (4)C7B—H7B0.95
C2A—C5A1.516 (4)C8B—C9B1.387 (5)
C2A—C3A1.533 (5)C8B—H8B0.95
C2A—H2A1C9B—C10B1.392 (4)
C3A—C4A1.556 (5)C9B—H9B0.95
C3A—H3A10.99C10B—H10B0.95
C3A—H3A20.99O1B—H1B0.83 (4)
C4A—H4A10.98C11A—C12A1.389 (4)
C4A—H4A20.98C11A—C15A1.393 (4)
C4A—H4A30.98C11A—C16A1.507 (4)
C5A—C10A1.374 (5)C12A—C13A1.389 (4)
C5A—C6A1.406 (5)C12A—H12A0.95
C6A—C7A1.385 (5)C13A—N2A1.335 (4)
C6A—H6A0.95C13A—H13A0.95
C7A—C8A1.380 (5)C14A—N2A1.328 (4)
C7A—H7A0.95C14A—C15A1.391 (4)
C8A—C9A1.366 (5)C14A—H14A0.95
C8A—H8A0.95C15A—H15A0.95
C9A—C10A1.384 (5)C16A—O3A1.230 (4)
C9A—H9A0.95C16A—N1A1.334 (4)
C10A—H10A0.95N1A—H1AS0.77 (4)
O1A—H1A0.88 (5)N1A—H1AA1.00 (4)
C1B—O2B1.223 (4)C11B—C15B1.383 (4)
C1B—O1B1.310 (3)C11B—C12B1.391 (4)
C1B—C2B1.522 (3)C11B—C16B1.516 (4)
C2B—C5B1.519 (3)C12B—C13B1.385 (4)
C2B—C3B1.535 (3)C12B—H12B0.95
C2B—H2B1C13B—N2B1.338 (4)
C3B—C4B1.525 (4)C13B—H13B0.95
C3B—H3B10.99C14B—N2B1.332 (4)
C3B—H3B20.99C14B—C15B1.391 (4)
C4B—H4B10.98C14B—H14B0.95
C4B—H4B20.98C15B—H15B0.95
C4B—H4B30.98C16B—O3B1.227 (4)
C5B—C6B1.387 (4)C16B—N1B1.330 (4)
C5B—C10B1.395 (4)N1B—H1BS0.90 (5)
C6B—C7B1.397 (4)N1B—H1BA0.82 (5)
O2A—C1A—O1A123.2 (3)C6B—C5B—C2B120.9 (2)
O2A—C1A—C2A118.8 (3)C10B—C5B—C2B120.8 (2)
O1A—C1A—C2A117.8 (3)C5B—C6B—C7B121.0 (3)
C5A—C2A—C3A113.8 (3)C5B—C6B—H6B119.5
C5A—C2A—C1A113.2 (3)C7B—C6B—H6B119.5
C3A—C2A—C1A107.0 (3)C8B—C7B—C6B120.0 (3)
C5A—C2A—H2A107.5C8B—C7B—H7B120
C3A—C2A—H2A107.5C6B—C7B—H7B120
C1A—C2A—H2A107.5C7B—C8B—C9B119.9 (3)
C2A—C3A—C4A110.9 (3)C7B—C8B—H8B120
C2A—C3A—H3A1109.5C9B—C8B—H8B120
C4A—C3A—H3A1109.5C8B—C9B—C10B120.0 (3)
C2A—C3A—H3A2109.5C8B—C9B—H9B120
C4A—C3A—H3A2109.5C10B—C9B—H9B120
H3A1—C3A—H3A2108C9B—C10B—C5B120.7 (3)
C3A—C4A—H4A1109.5C9B—C10B—H10B119.7
C3A—C4A—H4A2109.5C5B—C10B—H10B119.7
H4A1—C4A—H4A2109.5C1B—O1B—H1B114 (3)
C3A—C4A—H4A3109.5C12A—C11A—C15A118.2 (2)
H4A1—C4A—H4A3109.5C12A—C11A—C16A124.4 (2)
H4A2—C4A—H4A3109.5C15A—C11A—C16A117.3 (2)
C10A—C5A—C6A119.1 (3)C13A—C12A—C11A118.3 (3)
C10A—C5A—C2A116.7 (3)C13A—C12A—H12A120.8
C6A—C5A—C2A124.1 (3)C11A—C12A—H12A120.8
C7A—C6A—C5A119.9 (3)N2A—C13A—C12A123.7 (3)
C7A—C6A—H6A120N2A—C13A—H13A118.1
C5A—C6A—H6A120C12A—C13A—H13A118.1
C8A—C7A—C6A119.4 (3)N2A—C14A—C15A123.0 (3)
C8A—C7A—H7A120.3N2A—C14A—H14A118.5
C6A—C7A—H7A120.3C15A—C14A—H14A118.5
C9A—C8A—C7A120.9 (3)C14A—C15A—C11A118.9 (3)
C9A—C8A—H8A119.5C14A—C15A—H15A120.5
C7A—C8A—H8A119.5C11A—C15A—H15A120.5
C8A—C9A—C10A120.0 (3)O3A—C16A—N1A122.9 (3)
C8A—C9A—H9A120O3A—C16A—C11A119.3 (3)
C10A—C9A—H9A120N1A—C16A—C11A117.8 (3)
C5A—C10A—C9A120.6 (3)C16A—N1A—H1AS119 (3)
C5A—C10A—H10A119.7C16A—N1A—H1AA126 (2)
C9A—C10A—H10A119.7H1AS—N1A—H1AA115 (4)
C1A—O1A—H1A110 (3)C14A—N2A—C13A117.7 (3)
O2B—C1B—O1B122.6 (3)C15B—C11B—C12B118.7 (2)
O2B—C1B—C2B125.1 (3)C15B—C11B—C16B117.3 (2)
O1B—C1B—C2B112.3 (2)C12B—C11B—C16B124.0 (2)
C5B—C2B—C1B108.4 (2)C13B—C12B—C11B118.3 (3)
C5B—C2B—C3B113.4 (2)C13B—C12B—H12B120.9
C1B—C2B—C3B112.1 (2)C11B—C12B—H12B120.9
C5B—C2B—H2B107.6N2B—C13B—C12B123.5 (3)
C1B—C2B—H2B107.6N2B—C13B—H13B118.3
C3B—C2B—H2B107.6C12B—C13B—H13B118.3
C4B—C3B—C2B111.6 (2)N2B—C14B—C15B122.9 (3)
C4B—C3B—H3B1109.3N2B—C14B—H14B118.5
C2B—C3B—H3B1109.3C15B—C14B—H14B118.5
C4B—C3B—H3B2109.3C11B—C15B—C14B118.9 (3)
C2B—C3B—H3B2109.3C11B—C15B—H15B120.6
H3B1—C3B—H3B2108C14B—C15B—H15B120.6
C3B—C4B—H4B1109.5O3B—C16B—N1B124.0 (3)
C3B—C4B—H4B2109.5O3B—C16B—C11B118.4 (3)
H4B1—C4B—H4B2109.5N1B—C16B—C11B117.6 (3)
C3B—C4B—H4B3109.5C16B—N1B—H1BS107 (3)
H4B1—C4B—H4B3109.5C16B—N1B—H1BA121 (3)
H4B2—C4B—H4B3109.5H1BS—N1B—H1BA129 (4)
C6B—C5B—C10B118.3 (3)C14B—N2B—C13B117.7 (2)
O2A—C1A—C2A—C5A146.6 (3)C5B—C6B—C7B—C8B0.7 (5)
O1A—C1A—C2A—C5A29.2 (4)C6B—C7B—C8B—C9B0.4 (5)
O2A—C1A—C2A—C3A87.2 (4)C7B—C8B—C9B—C10B0.6 (5)
O1A—C1A—C2A—C3A97.0 (4)C8B—C9B—C10B—C5B1.1 (5)
C5A—C2A—C3A—C4A63.4 (4)C6B—C5B—C10B—C9B1.4 (4)
C1A—C2A—C3A—C4A170.8 (3)C2B—C5B—C10B—C9B178.5 (3)
C3A—C2A—C5A—C10A131.4 (3)C15A—C11A—C12A—C13A1.5 (4)
C1A—C2A—C5A—C10A106.1 (3)C16A—C11A—C12A—C13A179.5 (3)
C3A—C2A—C5A—C6A50.0 (4)C11A—C12A—C13A—N2A0.8 (5)
C1A—C2A—C5A—C6A72.5 (4)N2A—C14A—C15A—C11A1.4 (4)
C10A—C5A—C6A—C7A0.2 (5)C12A—C11A—C15A—C14A0.5 (4)
C2A—C5A—C6A—C7A178.8 (3)C16A—C11A—C15A—C14A179.6 (3)
C5A—C6A—C7A—C8A1.3 (5)C12A—C11A—C16A—O3A176.5 (3)
C6A—C7A—C8A—C9A1.7 (5)C15A—C11A—C16A—O3A2.5 (4)
C7A—C8A—C9A—C10A1.0 (6)C12A—C11A—C16A—N1A4.2 (4)
C6A—C5A—C10A—C9A0.5 (5)C15A—C11A—C16A—N1A176.8 (3)
C2A—C5A—C10A—C9A178.2 (3)C15A—C14A—N2A—C13A2.1 (4)
C8A—C9A—C10A—C5A0.1 (6)C12A—C13A—N2A—C14A1.0 (5)
O2B—C1B—C2B—C5B117.6 (3)C15B—C11B—C12B—C13B1.7 (4)
O1B—C1B—C2B—C5B61.4 (3)C16B—C11B—C12B—C13B179.7 (3)
O2B—C1B—C2B—C3B8.3 (4)C11B—C12B—C13B—N2B0.5 (5)
O1B—C1B—C2B—C3B172.7 (2)C12B—C11B—C15B—C14B2.0 (4)
C5B—C2B—C3B—C4B60.5 (3)C16B—C11B—C15B—C14B179.4 (3)
C1B—C2B—C3B—C4B176.4 (2)N2B—C14B—C15B—C11B1.0 (4)
C1B—C2B—C5B—C6B104.7 (3)C15B—C11B—C16B—O3B11.7 (4)
C3B—C2B—C5B—C6B130.1 (3)C12B—C11B—C16B—O3B166.8 (3)
C1B—C2B—C5B—C10B75.1 (3)C15B—C11B—C16B—N1B167.8 (3)
C3B—C2B—C5B—C10B50.0 (3)C12B—C11B—C16B—N1B13.7 (4)
C10B—C5B—C6B—C7B1.2 (5)C15B—C14B—N2B—C13B0.3 (4)
C2B—C5B—C6B—C7B178.7 (3)C12B—C13B—N2B—C14B0.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A···N2A0.88 (5)1.78 (5)2.652 (3)173 (4)
O1B—H1B···N2B0.83 (4)1.93 (4)2.662 (3)147 (4)
N1A—H1AS···O3B0.77 (4)2.13 (5)2.897 (3)171 (4)
N1A—H1AA···O2Bi1.00 (4)2.08 (4)3.062 (3)169 (3)
N1B—H1BS···O3A0.90 (5)2.04 (5)2.901 (3)160 (4)
N1B—H1BA···O2Aii0.82 (5)2.19 (5)3.002 (4)170 (4)
Symmetry codes: (i) x2, y1, z; (ii) x+2, y+1, z.
 

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