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
CCDC references: 718192; 718193; 718194; 718195; 718196; 718197; 718198; 718199
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
C9H10O2 | F(000) = 160 |
Mr = 150.17 | Dx = 1.286 Mg m−3 |
Monoclinic, P21 | Melting point = 302–303 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 6.3758 (13) Å | Cell parameters from 6231 reflections |
b = 7.1703 (14) Å | θ = 0.4–28.3° |
c = 8.6281 (17) Å | µ = 0.09 mm−1 |
β = 100.64 (3)° | T = 173 K |
V = 387.66 (13) Å3 | Spheroid, colourless |
Z = 2 | 0.55 × 0.46 × 0.4 mm |
Data collection top
Nonius KappaCCD area-detector diffractometer | 910 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
2.0° φ and ω scans | θmax = 28.0°, θmin = 3.3° |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | h = −8→8 |
Tmin = 0.953, Tmax = 0.967 | k = −9→9 |
6058 measured reflections | l = −9→11 |
1001 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.090 | H 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 parameters | Δρmax = 0.13 e Å−3 |
1 restraint | Δρmin = −0.19 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.6538 (3) | 0.5545 (3) | 0.08956 (18) | 0.0237 (3) | |
C2 | 0.8021 (3) | 0.7030 (2) | 0.16964 (19) | 0.0249 (4) | |
H2 | 0.7528 | 0.8253 | 0.1202 | 0.03* | |
C3 | 1.0271 (3) | 0.6683 (3) | 0.1400 (2) | 0.0348 (4) | |
H3A | 1.0772 | 0.5464 | 0.1831 | 0.052* | |
H3B | 1.1228 | 0.766 | 0.1916 | 0.052* | |
H3C | 1.0261 | 0.6701 | 0.0263 | 0.052* | |
C5 | 0.7817 (3) | 0.7122 (2) | 0.3423 (2) | 0.0238 (4) | |
C6 | 0.9270 (3) | 0.6319 (3) | 0.4617 (2) | 0.0291 (4) | |
H6 | 1.0486 | 0.5696 | 0.4377 | 0.035* | |
C7 | 0.8968 (3) | 0.6413 (3) | 0.6170 (2) | 0.0351 (4) | |
H7 | 0.9991 | 0.5871 | 0.6985 | 0.042* | |
C8 | 0.7209 (3) | 0.7282 (3) | 0.6535 (2) | 0.0361 (5) | |
H8 | 0.7003 | 0.7325 | 0.7597 | 0.043* | |
C9 | 0.5741 (3) | 0.8090 (3) | 0.5359 (2) | 0.0357 (5) | |
H9 | 0.4516 | 0.8691 | 0.5605 | 0.043* | |
C10 | 0.6057 (3) | 0.8025 (3) | 0.3811 (2) | 0.0300 (4) | |
H10 | 0.5055 | 0.8607 | 0.3004 | 0.036* | |
O1 | 0.7108 (2) | 0.38422 (18) | 0.13490 (16) | 0.0327 (3) | |
H1 | 0.625 (4) | 0.295 (4) | 0.075 (3) | 0.039* | |
O2 | 0.4949 (2) | 0.5860 (2) | −0.00660 (17) | 0.0336 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0271 (8) | 0.0231 (8) | 0.0216 (7) | 0.0008 (6) | 0.0063 (6) | −0.0003 (7) |
C2 | 0.0265 (8) | 0.0222 (8) | 0.0254 (8) | −0.0021 (6) | 0.0030 (6) | 0.0001 (7) |
C3 | 0.0292 (9) | 0.0409 (12) | 0.0361 (9) | −0.0043 (8) | 0.0104 (7) | −0.0009 (8) |
C5 | 0.0237 (8) | 0.0191 (8) | 0.0276 (8) | −0.0035 (7) | 0.0023 (6) | −0.0026 (7) |
C6 | 0.0304 (9) | 0.0260 (9) | 0.0296 (9) | 0.0023 (7) | 0.0016 (7) | −0.0003 (8) |
C7 | 0.0466 (11) | 0.0268 (9) | 0.0295 (9) | 0.0000 (8) | 0.0009 (8) | 0.0021 (8) |
C8 | 0.0500 (11) | 0.0301 (11) | 0.0297 (9) | −0.0063 (9) | 0.0115 (8) | −0.0042 (8) |
C9 | 0.0348 (10) | 0.0338 (11) | 0.0403 (10) | 0.0011 (8) | 0.0116 (8) | −0.0078 (9) |
C10 | 0.0277 (9) | 0.0272 (10) | 0.0341 (9) | 0.0029 (7) | 0.0031 (7) | −0.0032 (7) |
O1 | 0.0349 (7) | 0.0204 (7) | 0.0377 (7) | 0.0020 (5) | −0.0070 (6) | −0.0008 (5) |
O2 | 0.0340 (7) | 0.0249 (7) | 0.0361 (6) | −0.0001 (6) | −0.0083 (5) | 0.0006 (5) |
Geometric parameters (Å, º) top
C1—O2 | 1.206 (2) | C6—C7 | 1.390 (2) |
C1—O1 | 1.313 (2) | C6—H6 | 0.95 |
C1—C2 | 1.505 (2) | C7—C8 | 1.369 (3) |
C2—C5 | 1.520 (2) | C7—H7 | 0.95 |
C2—C3 | 1.523 (2) | C8—C9 | 1.375 (3) |
C2—H2 | 1 | C8—H8 | 0.95 |
C3—H3A | 0.98 | C9—C10 | 1.388 (3) |
C3—H3B | 0.98 | C9—H9 | 0.95 |
C3—H3C | 0.98 | C10—H10 | 0.95 |
C5—C6 | 1.378 (2) | O1—H1 | 0.93 (3) |
C5—C10 | 1.389 (2) | | |
| | | |
O2—C1—O1 | 122.04 (17) | C10—C5—C2 | 118.37 (15) |
O2—C1—C2 | 124.06 (17) | C5—C6—C7 | 120.45 (17) |
O1—C1—C2 | 113.90 (15) | C5—C6—H6 | 119.8 |
C1—C2—C5 | 108.68 (13) | C7—C6—H6 | 119.8 |
C1—C2—C3 | 109.80 (15) | C8—C7—C6 | 120.57 (18) |
C5—C2—C3 | 115.16 (15) | C8—C7—H7 | 119.7 |
C1—C2—H2 | 107.6 | C6—C7—H7 | 119.7 |
C5—C2—H2 | 107.6 | C7—C8—C9 | 119.80 (18) |
C3—C2—H2 | 107.6 | C7—C8—H8 | 120.1 |
C2—C3—H3A | 109.5 | C9—C8—H8 | 120.1 |
C2—C3—H3B | 109.5 | C8—C9—C10 | 119.73 (19) |
H3A—C3—H3B | 109.5 | C8—C9—H9 | 120.1 |
C2—C3—H3C | 109.5 | C10—C9—H9 | 120.1 |
H3A—C3—H3C | 109.5 | C9—C10—C5 | 120.98 (17) |
H3B—C3—H3C | 109.5 | C9—C10—H10 | 119.5 |
C6—C5—C10 | 118.45 (16) | C5—C10—H10 | 119.5 |
C6—C5—C2 | 123.17 (15) | C1—O1—H1 | 111.8 (15) |
| | | |
O2—C1—C2—C5 | 110.42 (19) | C10—C5—C6—C7 | 0.1 (3) |
O1—C1—C2—C5 | −68.86 (18) | C2—C5—C6—C7 | −178.48 (16) |
O2—C1—C2—C3 | −122.81 (19) | C5—C6—C7—C8 | 0.9 (3) |
O1—C1—C2—C3 | 57.91 (19) | C6—C7—C8—C9 | −0.9 (3) |
C1—C2—C5—C6 | 100.99 (19) | C7—C8—C9—C10 | −0.2 (3) |
C3—C2—C5—C6 | −22.6 (2) | C8—C9—C10—C5 | 1.3 (3) |
C1—C2—C5—C10 | −77.62 (19) | C6—C5—C10—C9 | −1.2 (3) |
C3—C2—C5—C10 | 158.75 (17) | C2—C5—C10—C9 | 177.45 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.93 (3) | 1.74 (3) | 2.643 (2) | 163 (2) |
C2—H2···O2ii | 1.00 | 2.53 | 3.482 (2) | 160 |
Symmetry codes: (i) −x+1, y−1/2, −z; (ii) −x+1, y+1/2, −z. |
(II) (
S)-2-phenylpropionic acid
top
Crystal data top
C9H10O2 | F(000) = 160 |
Mr = 150.17 | Dx = 1.268 Mg m−3 |
Monoclinic, P21 | Melting point = 302–303 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 6.4280 (13) Å | Cell parameters from 5429 reflections |
b = 7.1935 (14) Å | θ = 0.4–28.3° |
c = 8.6507 (17) Å | µ = 0.09 mm−1 |
β = 100.41 (3)° | T = 173 K |
V = 393.43 (13) Å3 | Spheroid, colourless |
Z = 2 | 0.45 × 0.4 × 0.38 mm |
Data collection top
Nonius KappaCCD area-detector diffractometer | 676 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
2.0° φ and ω scans | θmax = 25.5°, θmin = 3.7° |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | h = −7→7 |
Tmin = 0.963, Tmax = 0.970 | k = −8→8 |
4966 measured reflections | l = −10→10 |
801 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.1 | H 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 parameters | Δρmax = 0.17 e Å−3 |
1 restraint | Δρmin = −0.19 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.3467 (4) | 0.4456 (4) | 0.9103 (3) | 0.0305 (6) | |
C2 | 0.1981 (4) | 0.2967 (3) | 0.8299 (3) | 0.0313 (6) | |
H2 | 0.2468 | 0.1747 | 0.8788 | 0.038* | |
C3 | −0.0265 (5) | 0.3313 (4) | 0.8603 (3) | 0.0421 (7) | |
H3A | −0.076 | 0.4531 | 0.8181 | 0.063* | |
H3B | −0.0256 | 0.3286 | 0.9737 | 0.063* | |
H3C | −0.1213 | 0.2342 | 0.8086 | 0.063* | |
C5 | 0.2182 (4) | 0.2879 (3) | 0.6577 (3) | 0.0305 (6) | |
C6 | 0.0732 (4) | 0.3683 (4) | 0.5385 (3) | 0.0356 (7) | |
H6 | −0.0474 | 0.4303 | 0.5627 | 0.043* | |
C7 | 0.1034 (5) | 0.3586 (4) | 0.3835 (3) | 0.0404 (8) | |
H7 | 0.002 | 0.4124 | 0.3024 | 0.048* | |
C8 | 0.2788 (5) | 0.2718 (4) | 0.3466 (3) | 0.0421 (8) | |
H8 | 0.2993 | 0.2674 | 0.2407 | 0.051* | |
C9 | 0.4252 (5) | 0.1911 (4) | 0.4643 (3) | 0.0412 (7) | |
H9 | 0.5473 | 0.1318 | 0.4397 | 0.049* | |
C10 | 0.3927 (5) | 0.1974 (4) | 0.6187 (3) | 0.0361 (7) | |
H10 | 0.4913 | 0.1388 | 0.699 | 0.043* | |
O1 | 0.2893 (3) | 0.6159 (2) | 0.8649 (2) | 0.0398 (6) | |
H1 | 0.382 (5) | 0.702 (5) | 0.927 (4) | 0.048* | |
O2 | 0.5046 (3) | 0.4142 (3) | 1.0067 (2) | 0.0396 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0375 (16) | 0.0252 (13) | 0.0296 (13) | 0.0017 (11) | 0.0086 (12) | 0.0005 (11) |
C2 | 0.0353 (15) | 0.0223 (12) | 0.0358 (14) | −0.0016 (11) | 0.0049 (12) | 0.0002 (11) |
C3 | 0.0412 (17) | 0.0417 (17) | 0.0442 (16) | −0.0054 (13) | 0.0095 (13) | −0.0009 (13) |
C5 | 0.0363 (15) | 0.0183 (13) | 0.0359 (14) | −0.0036 (12) | 0.0037 (12) | −0.0025 (11) |
C6 | 0.0421 (17) | 0.0247 (14) | 0.0388 (15) | 0.0039 (12) | 0.0034 (13) | −0.0016 (12) |
C7 | 0.0555 (19) | 0.0270 (14) | 0.0356 (15) | 0.0006 (13) | 0.0000 (14) | 0.0015 (12) |
C8 | 0.061 (2) | 0.0294 (16) | 0.0384 (15) | −0.0043 (15) | 0.0154 (15) | −0.0053 (13) |
C9 | 0.0420 (17) | 0.0349 (17) | 0.0485 (17) | 0.0003 (13) | 0.0126 (14) | −0.0060 (14) |
C10 | 0.0353 (16) | 0.0285 (16) | 0.0426 (15) | −0.0004 (12) | 0.0021 (12) | −0.0035 (12) |
O1 | 0.0459 (12) | 0.0218 (10) | 0.0463 (12) | 0.0021 (9) | −0.0063 (9) | −0.0002 (9) |
O2 | 0.0429 (11) | 0.0258 (10) | 0.0442 (10) | 0.0006 (9) | −0.0077 (9) | 0.0004 (8) |
Geometric parameters (Å, º) top
C1—O2 | 1.213 (3) | C6—C7 | 1.390 (4) |
C1—O1 | 1.318 (3) | C6—H6 | 0.95 |
C1—C2 | 1.518 (4) | C7—C8 | 1.376 (4) |
C2—C5 | 1.519 (4) | C7—H7 | 0.95 |
C2—C3 | 1.533 (4) | C8—C9 | 1.383 (4) |
C2—H2 | 1 | C8—H8 | 0.95 |
C3—H3A | 0.98 | C9—C10 | 1.390 (4) |
C3—H3B | 0.98 | C9—H9 | 0.95 |
C3—H3C | 0.98 | C10—H10 | 0.95 |
C5—C6 | 1.386 (4) | O1—H1 | 0.96 (3) |
C5—C10 | 1.390 (4) | | |
| | | |
O2—C1—O1 | 122.2 (3) | C10—C5—C2 | 118.2 (2) |
O2—C1—C2 | 124.3 (3) | C5—C6—C7 | 120.3 (3) |
O1—C1—C2 | 113.6 (2) | C5—C6—H6 | 119.9 |
C1—C2—C5 | 108.7 (2) | C7—C6—H6 | 119.9 |
C1—C2—C3 | 109.9 (2) | C8—C7—C6 | 120.6 (3) |
C5—C2—C3 | 115.1 (2) | C8—C7—H7 | 119.7 |
C1—C2—H2 | 107.6 | C6—C7—H7 | 119.7 |
C5—C2—H2 | 107.6 | C7—C8—C9 | 119.8 (3) |
C3—C2—H2 | 107.6 | C7—C8—H8 | 120.1 |
C2—C3—H3A | 109.5 | C9—C8—H8 | 120.1 |
C2—C3—H3B | 109.5 | C8—C9—C10 | 119.5 (3) |
H3A—C3—H3B | 109.5 | C8—C9—H9 | 120.2 |
C2—C3—H3C | 109.5 | C10—C9—H9 | 120.2 |
H3A—C3—H3C | 109.5 | C5—C10—C9 | 121.1 (3) |
H3B—C3—H3C | 109.5 | C5—C10—H10 | 119.4 |
C6—C5—C10 | 118.6 (2) | C9—C10—H10 | 119.4 |
C6—C5—C2 | 123.2 (2) | C1—O1—H1 | 109 (2) |
| | | |
O2—C1—C2—C5 | −110.7 (3) | C10—C5—C6—C7 | −0.3 (4) |
O1—C1—C2—C5 | 68.9 (3) | C2—C5—C6—C7 | 178.6 (2) |
O2—C1—C2—C3 | 122.5 (3) | C5—C6—C7—C8 | −1.0 (4) |
O1—C1—C2—C3 | −58.0 (3) | C6—C7—C8—C9 | 0.9 (4) |
C1—C2—C5—C6 | −101.2 (3) | C7—C8—C9—C10 | 0.5 (5) |
C3—C2—C5—C6 | 22.6 (4) | C6—C5—C10—C9 | 1.6 (4) |
C1—C2—C5—C10 | 77.6 (3) | C2—C5—C10—C9 | −177.2 (3) |
C3—C2—C5—C10 | −158.5 (2) | C8—C9—C10—C5 | −1.8 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.96 (3) | 1.74 (4) | 2.657 (3) | 159 (3) |
C2—H2···O2ii | 1.00 | 2.54 | 3.500 (3) | 160 |
Symmetry codes: (i) −x+1, y+1/2, −z+2; (ii) −x+1, y−1/2, −z+2. |
(III) (
RS)-2-phenylbutyric acid
top
Crystal data top
C10H12O2 | Dx = 1.208 Mg m−3 |
Mr = 164.2 | Melting point = 312–315 K |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 11813 reflections |
a = 9.1724 (18) Å | θ = 0.4–28.3° |
b = 7.1850 (14) Å | µ = 0.08 mm−1 |
c = 27.407 (6) Å | T = 173 K |
V = 1806.2 (6) Å3 | Block, colourless |
Z = 8 | 0.4 × 0.32 × 0.2 mm |
F(000) = 704 | |
Data collection top
Nonius KappaCCD area-detector diffractometer | 1329 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
0.9° φ and ω scans | θmax = 25.5°, θmin = 3.0° |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | h = −11→8 |
Tmin = 0.968, Tmax = 0.984 | k = −8→8 |
9148 measured reflections | l = −33→29 |
1669 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.088 | H 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 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.47389 (15) | 0.20367 (18) | 0.54433 (4) | 0.0325 (3) | |
C2 | 0.45134 (15) | 0.36459 (17) | 0.57918 (4) | 0.0330 (3) | |
H2 | 0.3542 | 0.4215 | 0.5719 | 0.04* | |
C3 | 0.56779 (16) | 0.51464 (17) | 0.57210 (5) | 0.0397 (4) | |
H3A | 0.6629 | 0.4662 | 0.5835 | 0.048* | |
H3B | 0.5769 | 0.543 | 0.5369 | 0.048* | |
C4 | 0.53235 (19) | 0.69257 (19) | 0.59955 (6) | 0.0538 (4) | |
H4A | 0.4368 | 0.7389 | 0.5892 | 0.081* | |
H4B | 0.6069 | 0.7865 | 0.5925 | 0.081* | |
H4C | 0.5305 | 0.6671 | 0.6347 | 0.081* | |
C5 | 0.44733 (15) | 0.28926 (16) | 0.63121 (4) | 0.0322 (3) | |
C6 | 0.55964 (17) | 0.17759 (18) | 0.64840 (5) | 0.0410 (4) | |
H6 | 0.6392 | 0.1481 | 0.6276 | 0.049* | |
C7 | 0.5568 (2) | 0.1088 (2) | 0.69559 (5) | 0.0512 (4) | |
H7 | 0.634 | 0.0318 | 0.7069 | 0.061* | |
C8 | 0.4427 (2) | 0.1516 (2) | 0.72612 (5) | 0.0528 (4) | |
H8 | 0.441 | 0.1046 | 0.7585 | 0.063* | |
C9 | 0.33069 (19) | 0.2629 (2) | 0.70961 (5) | 0.0485 (4) | |
H9 | 0.2519 | 0.2927 | 0.7307 | 0.058* | |
C10 | 0.33266 (16) | 0.33182 (18) | 0.66214 (5) | 0.0387 (4) | |
H10 | 0.2551 | 0.4083 | 0.6509 | 0.046* | |
O1 | 0.35461 (11) | 0.11185 (14) | 0.53405 (4) | 0.0448 (3) | |
O2 | 0.59328 (11) | 0.16295 (14) | 0.52786 (3) | 0.0442 (3) | |
H1 | 0.382 (2) | 0.016 (3) | 0.5101 (7) | 0.092 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0322 (8) | 0.0364 (7) | 0.0288 (6) | −0.0030 (6) | −0.0019 (6) | 0.0066 (5) |
C2 | 0.0318 (8) | 0.0318 (6) | 0.0354 (7) | 0.0018 (6) | −0.0027 (6) | 0.0019 (5) |
C3 | 0.0405 (8) | 0.0340 (7) | 0.0446 (8) | −0.0033 (6) | −0.0014 (7) | 0.0044 (6) |
C4 | 0.0548 (11) | 0.0340 (7) | 0.0725 (11) | −0.0053 (7) | 0.0010 (8) | −0.0029 (7) |
C5 | 0.0361 (8) | 0.0277 (6) | 0.0328 (7) | −0.0031 (6) | −0.0018 (6) | −0.0032 (5) |
C6 | 0.0457 (9) | 0.0407 (7) | 0.0367 (7) | 0.0057 (7) | −0.0034 (6) | −0.0009 (6) |
C7 | 0.0674 (12) | 0.0454 (8) | 0.0408 (8) | 0.0054 (8) | −0.0132 (8) | 0.0032 (6) |
C8 | 0.0810 (13) | 0.0465 (8) | 0.0307 (7) | −0.0118 (9) | −0.0040 (8) | −0.0008 (6) |
C9 | 0.0617 (11) | 0.0466 (8) | 0.0373 (8) | −0.0114 (8) | 0.0104 (7) | −0.0100 (6) |
C10 | 0.0414 (9) | 0.0338 (7) | 0.0407 (8) | −0.0027 (6) | 0.0013 (6) | −0.0067 (6) |
O1 | 0.0336 (6) | 0.0514 (6) | 0.0493 (6) | −0.0086 (5) | 0.0030 (5) | −0.0129 (5) |
O2 | 0.0334 (6) | 0.0499 (6) | 0.0493 (6) | −0.0058 (5) | 0.0042 (5) | −0.0117 (4) |
Geometric parameters (Å, º) top
C1—O2 | 1.2201 (16) | C5—C10 | 1.3851 (19) |
C1—O1 | 1.3083 (16) | C5—C6 | 1.3881 (19) |
C1—C2 | 1.5139 (18) | C6—C7 | 1.385 (2) |
C2—C5 | 1.5258 (17) | C6—H6 | 0.95 |
C2—C3 | 1.5300 (18) | C7—C8 | 1.375 (2) |
C2—H2 | 1 | C7—H7 | 0.95 |
C3—C4 | 1.5186 (19) | C8—C9 | 1.378 (2) |
C3—H3A | 0.99 | C8—H8 | 0.95 |
C3—H3B | 0.99 | C9—C10 | 1.3922 (19) |
C4—H4A | 0.98 | C9—H9 | 0.95 |
C4—H4B | 0.98 | C10—H10 | 0.95 |
C4—H4C | 0.98 | O1—H1 | 0.99 (2) |
| | | |
O2—C1—O1 | 123.38 (12) | H4B—C4—H4C | 109.5 |
O2—C1—C2 | 122.62 (12) | C10—C5—C6 | 118.90 (12) |
O1—C1—C2 | 114.00 (12) | C10—C5—C2 | 120.80 (12) |
C1—C2—C5 | 108.79 (10) | C6—C5—C2 | 120.30 (12) |
C1—C2—C3 | 111.27 (11) | C7—C6—C5 | 120.63 (14) |
C5—C2—C3 | 112.66 (11) | C7—C6—H6 | 119.7 |
C1—C2—H2 | 108 | C5—C6—H6 | 119.7 |
C5—C2—H2 | 108 | C8—C7—C6 | 120.17 (15) |
C3—C2—H2 | 108 | C8—C7—H7 | 119.9 |
C4—C3—C2 | 112.39 (12) | C6—C7—H7 | 119.9 |
C4—C3—H3A | 109.1 | C7—C8—C9 | 119.84 (14) |
C2—C3—H3A | 109.1 | C7—C8—H8 | 120.1 |
C4—C3—H3B | 109.1 | C9—C8—H8 | 120.1 |
C2—C3—H3B | 109.1 | C8—C9—C10 | 120.24 (14) |
H3A—C3—H3B | 107.9 | C8—C9—H9 | 119.9 |
C3—C4—H4A | 109.5 | C10—C9—H9 | 119.9 |
C3—C4—H4B | 109.5 | C5—C10—C9 | 120.22 (14) |
H4A—C4—H4B | 109.5 | C5—C10—H10 | 119.9 |
C3—C4—H4C | 109.5 | C9—C10—H10 | 119.9 |
H4A—C4—H4C | 109.5 | C1—O1—H1 | 106.7 (12) |
| | | |
O2—C1—C2—C5 | −97.82 (14) | C3—C2—C5—C6 | −70.79 (15) |
O1—C1—C2—C5 | 81.43 (14) | C10—C5—C6—C7 | 0.4 (2) |
O2—C1—C2—C3 | 26.86 (17) | C2—C5—C6—C7 | 179.96 (13) |
O1—C1—C2—C3 | −153.88 (11) | C5—C6—C7—C8 | −0.4 (2) |
C1—C2—C3—C4 | 169.29 (12) | C6—C7—C8—C9 | 0.2 (2) |
C5—C2—C3—C4 | −68.23 (15) | C7—C8—C9—C10 | 0.1 (2) |
C1—C2—C5—C10 | −127.38 (13) | C6—C5—C10—C9 | −0.14 (19) |
C3—C2—C5—C10 | 108.76 (14) | C2—C5—C10—C9 | −179.70 (12) |
C1—C2—C5—C6 | 53.07 (16) | C8—C9—C10—C5 | −0.1 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.99 (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·C6H6N2O | F(000) = 1152 |
Mr = 272.3 | Dx = 1.282 Mg m−3 |
Monoclinic, C2/c | Melting point: 364 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 31.899 (3) Å | Cell parameters from 20822 reflections |
b = 5.4007 (5) Å | θ = 0.4–27.5° |
c = 20.8815 (16) Å | µ = 0.09 mm−1 |
β = 128.319 (3)° | T = 173 K |
V = 2822.4 (4) Å3 | Block, colourless |
Z = 8 | 0.49 × 0.08 × 0.06 mm |
Data collection top
Nonius KappaCCD area-detector diffractometer | 1930 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.074 |
1.5° φ and ω scans | θmax = 27.5°, θmin = 3.7° |
Absorption correction: integration Bruker XPREP (Bruker, 1999) | h = −40→40 |
Tmin = 0.961, Tmax = 0.994 | k = −7→6 |
19532 measured reflections | l = −27→25 |
3204 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.155 | H 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 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.61761 (7) | −0.2669 (3) | 0.90172 (11) | 0.0385 (4) | |
C2 | 0.64899 (8) | −0.4338 (3) | 0.97622 (11) | 0.0453 (5) | |
H2A | 0.623 | −0.5192 | 0.9805 | 0.054* | 0.621 (4) |
H2B | 0.6721 | −0.546 | 0.9719 | 0.054* | 0.379 (4) |
C3A | 0.68132 (15) | −0.6336 (6) | 0.97128 (19) | 0.0588 (11) | 0.621 (4) |
H3A1 | 0.6568 | −0.7447 | 0.9254 | 0.088* | 0.621 (4) |
H3A2 | 0.7024 | −0.7288 | 1.0222 | 0.088* | 0.621 (4) |
H3A3 | 0.7053 | −0.5542 | 0.9631 | 0.088* | 0.621 (4) |
C3B | 0.6076 (2) | −0.5947 (10) | 0.9749 (3) | 0.0583 (17) | 0.379 (4) |
H3B1 | 0.5843 | −0.4863 | 0.9781 | 0.087* | 0.379 (4) |
H3B2 | 0.6267 | −0.708 | 1.0216 | 0.087* | 0.379 (4) |
H3B3 | 0.5859 | −0.6905 | 0.9241 | 0.087* | 0.379 (4) |
C5 | 0.68469 (7) | −0.2700 (3) | 1.05113 (11) | 0.0434 (5) | |
C6 | 0.73938 (8) | −0.2590 (4) | 1.09397 (12) | 0.0539 (5) | |
H6 | 0.7556 | −0.3592 | 1.0773 | 0.065* | |
C7 | 0.77084 (9) | −0.1044 (5) | 1.16065 (12) | 0.0631 (6) | |
H7 | 0.8084 | −0.1003 | 1.1894 | 0.076* | |
C8 | 0.74847 (9) | 0.0432 (4) | 1.18572 (12) | 0.0628 (6) | |
H8 | 0.7702 | 0.1493 | 1.2316 | 0.075* | |
C9 | 0.69432 (9) | 0.0357 (4) | 1.14376 (13) | 0.0659 (6) | |
H9 | 0.6784 | 0.1384 | 1.1603 | 0.079* | |
C10 | 0.66273 (9) | −0.1202 (4) | 1.07754 (13) | 0.0580 (6) | |
H10 | 0.6253 | −0.125 | 1.0496 | 0.07* | |
O1 | 0.64343 (5) | −0.2103 (3) | 0.87385 (8) | 0.0541 (4) | |
H1 | 0.6219 (8) | −0.077 (4) | 0.8248 (12) | 0.065* | |
O2 | 0.57275 (5) | −0.1904 (3) | 0.87031 (7) | 0.0476 (4) | |
C11 | 0.55156 (6) | 0.5115 (3) | 0.64484 (9) | 0.0346 (4) | |
C12 | 0.53463 (8) | 0.4591 (4) | 0.69053 (11) | 0.0494 (5) | |
H12 | 0.5074 | 0.5557 | 0.6843 | 0.059* | |
C13 | 0.55773 (8) | 0.2655 (4) | 0.74507 (11) | 0.0492 (5) | |
H13 | 0.5456 | 0.2311 | 0.7757 | 0.059* | |
C14 | 0.61241 (8) | 0.1754 (4) | 0.71302 (12) | 0.0481 (5) | |
H14 | 0.6398 | 0.0763 | 0.7206 | 0.058* | |
C15 | 0.59129 (7) | 0.3650 (3) | 0.65722 (11) | 0.0432 (5) | |
H15 | 0.6041 | 0.395 | 0.6272 | 0.052* | |
C16 | 0.52975 (7) | 0.7187 (3) | 0.58370 (10) | 0.0383 (4) | |
N1 | 0.48989 (6) | 0.8536 (3) | 0.56910 (10) | 0.0441 (4) | |
H1S | 0.4777 (8) | 0.980 (4) | 0.5332 (12) | 0.053* | |
H1A | 0.4760 (8) | 0.829 (4) | 0.5929 (11) | 0.053* | |
N2 | 0.59612 (6) | 0.1242 (3) | 0.75713 (9) | 0.0420 (4) | |
O3 | 0.55010 (5) | 0.7572 (2) | 0.54989 (8) | 0.0507 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0437 (11) | 0.0359 (10) | 0.0447 (10) | −0.0044 (8) | 0.0318 (9) | −0.0027 (8) |
C2 | 0.0530 (12) | 0.0401 (11) | 0.0484 (10) | −0.0016 (9) | 0.0341 (10) | 0.0070 (8) |
C3A | 0.078 (3) | 0.0387 (19) | 0.0459 (18) | 0.0033 (17) | 0.0314 (18) | 0.0049 (14) |
C3B | 0.072 (4) | 0.047 (3) | 0.060 (3) | 0.003 (3) | 0.043 (3) | 0.016 (3) |
C5 | 0.0505 (11) | 0.0431 (11) | 0.0448 (10) | 0.0000 (9) | 0.0336 (10) | 0.0095 (8) |
C6 | 0.0511 (12) | 0.0586 (14) | 0.0549 (12) | 0.0088 (10) | 0.0343 (11) | 0.0058 (10) |
C7 | 0.0484 (12) | 0.0767 (16) | 0.0540 (12) | 0.0006 (11) | 0.0267 (11) | −0.0013 (11) |
C8 | 0.0672 (15) | 0.0738 (16) | 0.0488 (11) | −0.0115 (12) | 0.0367 (12) | −0.0076 (11) |
C9 | 0.0684 (15) | 0.0841 (17) | 0.0654 (13) | −0.0098 (13) | 0.0516 (13) | −0.0171 (12) |
C10 | 0.0544 (12) | 0.0741 (15) | 0.0615 (12) | −0.0087 (11) | 0.0438 (11) | −0.0074 (11) |
O1 | 0.0505 (8) | 0.0617 (9) | 0.0674 (9) | 0.0189 (7) | 0.0452 (8) | 0.0293 (7) |
O2 | 0.0401 (8) | 0.0619 (9) | 0.0475 (7) | −0.0021 (6) | 0.0305 (6) | 0.0011 (6) |
C11 | 0.0344 (9) | 0.0366 (10) | 0.0329 (8) | −0.0008 (8) | 0.0209 (8) | −0.0004 (7) |
C12 | 0.0518 (12) | 0.0592 (13) | 0.0516 (10) | 0.0207 (10) | 0.0392 (10) | 0.0189 (9) |
C13 | 0.0509 (12) | 0.0622 (13) | 0.0481 (11) | 0.0122 (10) | 0.0374 (10) | 0.0151 (9) |
C14 | 0.0474 (11) | 0.0468 (12) | 0.0631 (12) | 0.0100 (9) | 0.0406 (11) | 0.0130 (10) |
C15 | 0.0463 (11) | 0.0447 (11) | 0.0512 (10) | 0.0047 (9) | 0.0364 (9) | 0.0080 (9) |
C16 | 0.0395 (10) | 0.0416 (10) | 0.0371 (9) | 0.0021 (8) | 0.0254 (9) | 0.0030 (8) |
N1 | 0.0458 (9) | 0.0495 (10) | 0.0477 (9) | 0.0120 (8) | 0.0343 (8) | 0.0150 (8) |
N2 | 0.0376 (8) | 0.0461 (9) | 0.0427 (8) | 0.0025 (7) | 0.0251 (7) | 0.0071 (7) |
O3 | 0.0567 (8) | 0.0564 (9) | 0.0590 (8) | 0.0162 (6) | 0.0459 (7) | 0.0203 (6) |
Geometric parameters (Å, º) top
C1—O2 | 1.219 (2) | C8—C9 | 1.370 (3) |
C1—O1 | 1.3059 (19) | C8—H8 | 0.95 |
C1—C2 | 1.518 (3) | C9—C10 | 1.382 (3) |
C2—C5 | 1.522 (3) | C9—H9 | 0.95 |
C2—C3A | 1.540 (4) | C10—H10 | 0.95 |
C2—C3B | 1.567 (6) | O1—H1 | 1.08 (2) |
C2—H2A | 1 | C11—C15 | 1.375 (2) |
C2—H2B | 1 | C11—C12 | 1.386 (2) |
C3A—H2B | 0.5616 | C11—C16 | 1.505 (2) |
C3A—H3A1 | 0.98 | C12—C13 | 1.376 (3) |
C3A—H3A2 | 0.98 | C12—H12 | 0.95 |
C3A—H3A3 | 0.98 | C13—N2 | 1.328 (2) |
C3B—H3B1 | 0.98 | C13—H13 | 0.95 |
C3B—H3B2 | 0.98 | C14—N2 | 1.337 (2) |
C3B—H3B3 | 0.98 | C14—C15 | 1.374 (3) |
C5—C6 | 1.383 (3) | C14—H14 | 0.95 |
C5—C10 | 1.388 (3) | C15—H15 | 0.95 |
C6—C7 | 1.382 (3) | C16—O3 | 1.2375 (19) |
C6—H6 | 0.95 | C16—N1 | 1.327 (2) |
C7—C8 | 1.372 (3) | N1—H1S | 0.90 (2) |
C7—H7 | 0.95 | N1—H1A | 0.86 (2) |
| | | |
O2—C1—O1 | 122.37 (16) | C8—C7—H7 | 119.6 |
O2—C1—C2 | 124.13 (15) | C6—C7—H7 | 119.6 |
O1—C1—C2 | 113.49 (15) | C9—C8—C7 | 119.1 (2) |
C1—C2—C5 | 107.82 (15) | C9—C8—H8 | 120.4 |
C1—C2—C3A | 113.00 (17) | C7—C8—H8 | 120.4 |
C5—C2—C3A | 111.8 (2) | C8—C9—C10 | 120.4 (2) |
C1—C2—C3B | 107.4 (2) | C8—C9—H9 | 119.8 |
C5—C2—C3B | 115.2 (2) | C10—C9—H9 | 119.8 |
C3A—C2—C3B | 101.7 (3) | C9—C10—C5 | 121.2 (2) |
C1—C2—H2A | 108 | C9—C10—H10 | 119.4 |
C5—C2—H2A | 108 | C5—C10—H10 | 119.4 |
C3A—C2—H2A | 108 | C1—O1—H1 | 111.9 (11) |
C1—C2—H2B | 108.8 | C15—C11—C12 | 117.39 (15) |
C5—C2—H2B | 108.8 | C15—C11—C16 | 118.33 (14) |
C3B—C2—H2B | 108.8 | C12—C11—C16 | 124.28 (15) |
C2—C3A—H3A1 | 109.5 | C13—C12—C11 | 119.19 (16) |
H2B—C3A—H3A1 | 115.2 | C13—C12—H12 | 120.4 |
C2—C3A—H3A2 | 109.5 | C11—C12—H12 | 120.4 |
H2B—C3A—H3A2 | 115.8 | N2—C13—C12 | 123.47 (16) |
C2—C3A—H3A3 | 109.5 | N2—C13—H13 | 118.3 |
H2B—C3A—H3A3 | 96.6 | C12—C13—H13 | 118.3 |
C2—C3B—H3B1 | 109.5 | N2—C14—C15 | 122.86 (17) |
C2—C3B—H3B2 | 109.5 | N2—C14—H14 | 118.6 |
H3B1—C3B—H3B2 | 109.5 | C15—C14—H14 | 118.6 |
C2—C3B—H3B3 | 109.5 | C14—C15—C11 | 119.90 (16) |
H3B1—C3B—H3B3 | 109.5 | C14—C15—H15 | 120.1 |
H3B2—C3B—H3B3 | 109.5 | C11—C15—H15 | 120.1 |
C6—C5—C10 | 117.58 (19) | O3—C16—N1 | 122.92 (16) |
C6—C5—C2 | 121.96 (17) | O3—C16—C11 | 118.61 (15) |
C10—C5—C2 | 120.44 (18) | N1—C16—C11 | 118.47 (15) |
C7—C6—C5 | 120.93 (19) | C16—N1—H1S | 117.7 (12) |
C7—C6—H6 | 119.5 | C16—N1—H1A | 123.3 (14) |
C5—C6—H6 | 119.5 | H1S—N1—H1A | 119.0 (19) |
C8—C7—C6 | 120.7 (2) | C13—N2—C14 | 117.20 (15) |
| | | |
O2—C1—C2—C5 | −94.7 (2) | C7—C8—C9—C10 | 0.6 (3) |
O1—C1—C2—C5 | 84.95 (19) | C8—C9—C10—C5 | −0.9 (3) |
O2—C1—C2—C3A | 141.3 (2) | C6—C5—C10—C9 | 0.6 (3) |
O1—C1—C2—C3A | −39.1 (3) | C2—C5—C10—C9 | −177.82 (18) |
O2—C1—C2—C3B | 30.0 (3) | C15—C11—C12—C13 | −0.3 (3) |
O1—C1—C2—C3B | −150.4 (3) | C16—C11—C12—C13 | −179.61 (17) |
C1—C2—C5—C6 | −107.39 (19) | C11—C12—C13—N2 | 0.4 (3) |
C3A—C2—C5—C6 | 17.4 (3) | N2—C14—C15—C11 | −0.1 (3) |
C3B—C2—C5—C6 | 132.8 (3) | C12—C11—C15—C14 | 0.1 (3) |
C1—C2—C5—C10 | 70.9 (2) | C16—C11—C15—C14 | 179.51 (17) |
C3A—C2—C5—C10 | −164.3 (2) | C15—C11—C16—O3 | −3.5 (2) |
C3B—C2—C5—C10 | −48.9 (3) | C12—C11—C16—O3 | 175.80 (17) |
C10—C5—C6—C7 | 0.1 (3) | C15—C11—C16—N1 | 177.20 (17) |
C2—C5—C6—C7 | 178.42 (18) | C12—C11—C16—N1 | −3.5 (3) |
C5—C6—C7—C8 | −0.4 (3) | C12—C13—N2—C14 | −0.3 (3) |
C6—C7—C8—C9 | 0.0 (3) | C15—C14—N2—C13 | 0.2 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2 | 1.08 (2) | 1.55 (2) | 2.631 (2) | 175 (2) |
N1—H1S···O3i | 0.90 (2) | 1.98 (2) | 2.879 (2) | 177 (2) |
N1—H1A···O2ii | 0.86 (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·C6H6N2O | F(000) = 1152 |
Mr = 272.3 | Dx = 1.27 Mg m−3 |
Monoclinic, C2 | Melting point: 360 K |
Hall symbol: C 2y | Mo Kα radiation, λ = 0.71073 Å |
a = 32.006 (2) Å | Cell parameters from 21845 reflections |
b = 5.4698 (4) Å | θ = 1–28.3° |
c = 20.8451 (10) Å | µ = 0.09 mm−1 |
β = 128.690 (3)° | T = 173 K |
V = 2848.4 (3) Å3 | Plate, colourless |
Z = 8 | 0.38 × 0.15 × 0.03 mm |
Data collection top
Nonius KappaCCD area-detector diffractometer | 2254 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.072 |
2.0° φ and ω scans | θmax = 28.0°, θmin = 1.3° |
Absorption correction: integration Bruker XPREP (Bruker, 1999) | h = −42→39 |
Tmin = 0.973, Tmax = 0.997 | k = −7→7 |
21632 measured reflections | l = −27→27 |
3784 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H 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 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1A | 0.61768 (12) | −0.3452 (9) | 1.14879 (17) | 0.0307 (8) | |
C2A | 0.64893 (13) | −0.5225 (9) | 1.22036 (17) | 0.0361 (9) | |
H2A | 0.6711 | −0.6287 | 1.2129 | 0.043* | |
C3A | 0.61174 (14) | −0.6868 (9) | 1.2238 (2) | 0.0519 (10) | |
H3A1 | 0.5884 | −0.5854 | 1.2282 | 0.078* | |
H3A2 | 0.6332 | −0.7945 | 1.2718 | 0.078* | |
H3A3 | 0.5899 | −0.7859 | 1.1737 | 0.078* | |
C5A | 0.68656 (13) | −0.3754 (10) | 1.29905 (18) | 0.0361 (8) | |
C6A | 0.74102 (13) | −0.3651 (10) | 1.33889 (19) | 0.0466 (10) | |
H6A | 0.7552 | −0.4557 | 1.3176 | 0.056* | |
C7A | 0.77517 (15) | −0.2258 (11) | 1.4090 (2) | 0.0540 (10) | |
H7A | 0.8123 | −0.2201 | 1.435 | 0.065* | |
C8A | 0.75527 (14) | −0.0953 (10) | 1.44124 (19) | 0.0486 (10) | |
H8A | 0.7786 | −0.0013 | 1.4898 | 0.058* | |
C9A | 0.70121 (14) | −0.1020 (10) | 1.40238 (18) | 0.0465 (10) | |
H9A | 0.6872 | −0.011 | 1.4239 | 0.056* | |
C10A | 0.66737 (14) | −0.2404 (10) | 1.33236 (19) | 0.0398 (9) | |
H10A | 0.6302 | −0.2437 | 1.3063 | 0.048* | |
O1A | 0.64482 (9) | −0.2758 (8) | 1.12384 (13) | 0.0464 (7) | |
H1A | 0.6240 (13) | −0.153 (8) | 1.0793 (19) | 0.056* | |
O2A | 0.57279 (8) | −0.2705 (8) | 1.11774 (11) | 0.0359 (6) | |
C1B | 0.38415 (13) | 2.1759 (9) | 0.34686 (18) | 0.0330 (8) | |
C2B | 0.35274 (13) | 2.3342 (10) | 0.26988 (17) | 0.0401 (9) | |
H2B | 0.3789 | 2.4108 | 0.2647 | 0.048* | |
C3B | 0.32344 (16) | 2.5389 (10) | 0.2766 (2) | 0.0599 (11) | |
H3B1 | 0.2992 | 2.4686 | 0.2853 | 0.09* | |
H3B2 | 0.3028 | 2.635 | 0.2257 | 0.09* | |
H3B3 | 0.3495 | 2.645 | 0.323 | 0.09* | |
C5B | 0.31642 (13) | 2.1665 (8) | 0.19631 (17) | 0.0331 (8) | |
C6B | 0.26221 (13) | 2.1551 (9) | 0.15475 (18) | 0.0439 (9) | |
H6B | 0.2463 | 2.256 | 0.1712 | 0.053* | |
C7B | 0.23050 (14) | 1.9958 (10) | 0.0884 (2) | 0.0516 (10) | |
H7B | 0.1929 | 1.9905 | 0.0594 | 0.062* | |
C8B | 0.25335 (15) | 1.8464 (10) | 0.06486 (19) | 0.0493 (10) | |
H8B | 0.2316 | 1.738 | 0.0197 | 0.059* | |
C9B | 0.30771 (13) | 1.8546 (10) | 0.10681 (18) | 0.0454 (9) | |
H9B | 0.3236 | 1.7508 | 0.091 | 0.054* | |
C10B | 0.33913 (14) | 2.0139 (10) | 0.17207 (18) | 0.0421 (9) | |
H10B | 0.3766 | 2.0193 | 0.2007 | 0.051* | |
O1B | 0.35785 (8) | 2.1233 (8) | 0.37419 (12) | 0.0378 (6) | |
H1B | 0.3767 (12) | 1.997 (7) | 0.4220 (17) | 0.045* | |
O2B | 0.42915 (9) | 2.1016 (9) | 0.37963 (12) | 0.0454 (7) | |
C11A | 0.55096 (12) | 0.4412 (9) | 0.89403 (17) | 0.0303 (8) | |
C12A | 0.53557 (13) | 0.3932 (10) | 0.94211 (18) | 0.0396 (9) | |
H12A | 0.5094 | 0.4917 | 0.9377 | 0.048* | |
C13A | 0.55914 (13) | 0.1995 (10) | 0.99634 (18) | 0.0405 (9) | |
H13A | 0.548 | 0.1663 | 1.0283 | 0.049* | |
C14A | 0.61086 (13) | 0.1045 (10) | 0.96029 (18) | 0.0384 (8) | |
H14A | 0.6375 | 0.0043 | 0.9666 | 0.046* | |
C15A | 0.58925 (12) | 0.2918 (9) | 0.90374 (17) | 0.0356 (8) | |
H15A | 0.6006 | 0.3179 | 0.8717 | 0.043* | |
C16A | 0.52861 (13) | 0.6466 (10) | 0.83209 (17) | 0.0323 (8) | |
N1A | 0.48951 (11) | 0.7829 (8) | 0.81860 (15) | 0.0356 (7) | |
H1AS | 0.4708 (11) | 0.919 (7) | 0.7695 (17) | 0.043* | |
H1AA | 0.4744 (12) | 0.757 (7) | 0.8418 (17) | 0.043* | |
N2A | 0.59638 (10) | 0.0566 (9) | 1.00663 (15) | 0.0358 (7) | |
O3A | 0.54818 (8) | 0.6831 (8) | 0.79701 (12) | 0.0429 (6) | |
C11B | 0.44883 (12) | 1.4143 (9) | 0.60505 (16) | 0.0288 (7) | |
C12B | 0.46707 (13) | 1.4695 (10) | 0.56214 (19) | 0.0458 (10) | |
H12B | 0.4951 | 1.3767 | 0.5701 | 0.055* | |
C13B | 0.44411 (14) | 1.6618 (10) | 0.5072 (2) | 0.0482 (10) | |
H13B | 0.4572 | 1.6986 | 0.478 | 0.058* | |
C14B | 0.38684 (13) | 1.7415 (10) | 0.53397 (18) | 0.0404 (9) | |
H14B | 0.3583 | 1.8346 | 0.5241 | 0.048* | |
C15B | 0.40811 (13) | 1.5528 (10) | 0.59034 (18) | 0.0389 (9) | |
H15B | 0.3944 | 1.5195 | 0.6188 | 0.047* | |
C16B | 0.47000 (12) | 1.2063 (9) | 0.66554 (17) | 0.0319 (8) | |
N1B | 0.50995 (11) | 1.0747 (9) | 0.68074 (15) | 0.0367 (7) | |
H1BS | 0.5220 (13) | 0.954 (7) | 0.7141 (19) | 0.044* | |
H1BA | 0.5277 (12) | 1.101 (7) | 0.6577 (16) | 0.044* | |
N2B | 0.40484 (10) | 1.7978 (9) | 0.49295 (14) | 0.0342 (7) | |
O3B | 0.44947 (9) | 1.1679 (8) | 0.69884 (13) | 0.0472 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1A | 0.0326 (19) | 0.0313 (19) | 0.0277 (15) | −0.0010 (16) | 0.0185 (15) | 0.0011 (15) |
C2A | 0.043 (2) | 0.031 (2) | 0.0346 (17) | 0.0057 (16) | 0.0238 (16) | 0.0045 (15) |
C3A | 0.064 (2) | 0.037 (2) | 0.0502 (18) | −0.0009 (19) | 0.0335 (18) | 0.0094 (17) |
C5A | 0.038 (2) | 0.0346 (19) | 0.0362 (17) | 0.0065 (16) | 0.0235 (15) | 0.0109 (16) |
C6A | 0.042 (2) | 0.055 (2) | 0.0440 (18) | 0.0080 (19) | 0.0274 (17) | 0.0043 (19) |
C7A | 0.041 (2) | 0.065 (3) | 0.051 (2) | −0.002 (2) | 0.0265 (18) | −0.007 (2) |
C8A | 0.050 (2) | 0.051 (2) | 0.0421 (19) | 0.002 (2) | 0.0276 (18) | 0.0009 (19) |
C9A | 0.053 (2) | 0.054 (2) | 0.0421 (18) | 0.009 (2) | 0.0343 (17) | 0.0043 (18) |
C10A | 0.0395 (19) | 0.044 (2) | 0.0406 (17) | 0.0047 (17) | 0.0274 (16) | 0.0062 (17) |
O1A | 0.0406 (15) | 0.0589 (19) | 0.0490 (14) | 0.0149 (15) | 0.0325 (13) | 0.0263 (15) |
O2A | 0.0325 (13) | 0.0407 (14) | 0.0380 (12) | 0.0031 (12) | 0.0239 (10) | 0.0047 (11) |
C1B | 0.038 (2) | 0.034 (2) | 0.0336 (17) | −0.0105 (17) | 0.0259 (16) | −0.0057 (16) |
C2B | 0.051 (2) | 0.037 (2) | 0.0343 (17) | −0.0096 (18) | 0.0278 (17) | 0.0021 (16) |
C3B | 0.087 (3) | 0.0314 (19) | 0.0427 (18) | 0.004 (2) | 0.0319 (19) | 0.0036 (17) |
C5B | 0.041 (2) | 0.0306 (18) | 0.0296 (15) | −0.0035 (16) | 0.0233 (15) | 0.0040 (15) |
C6B | 0.042 (2) | 0.044 (2) | 0.0443 (18) | 0.0021 (18) | 0.0265 (17) | 0.0015 (18) |
C7B | 0.035 (2) | 0.062 (3) | 0.047 (2) | −0.0044 (19) | 0.0203 (17) | −0.002 (2) |
C8B | 0.056 (2) | 0.051 (3) | 0.0367 (17) | −0.011 (2) | 0.0266 (17) | −0.0089 (17) |
C9B | 0.050 (2) | 0.053 (2) | 0.0419 (18) | −0.0021 (19) | 0.0335 (17) | −0.0049 (18) |
C10B | 0.0383 (19) | 0.058 (2) | 0.0340 (16) | −0.0027 (18) | 0.0246 (15) | 0.0022 (18) |
O1B | 0.0378 (14) | 0.0423 (15) | 0.0410 (12) | 0.0081 (12) | 0.0284 (12) | 0.0116 (13) |
O2B | 0.0339 (14) | 0.0674 (18) | 0.0387 (12) | −0.0029 (14) | 0.0246 (11) | 0.0012 (13) |
C11A | 0.0289 (18) | 0.033 (2) | 0.0272 (15) | −0.0030 (16) | 0.0168 (14) | −0.0024 (15) |
C12A | 0.041 (2) | 0.046 (2) | 0.0412 (17) | 0.0086 (19) | 0.0303 (16) | 0.0050 (18) |
C13A | 0.041 (2) | 0.051 (2) | 0.0337 (16) | 0.0082 (19) | 0.0251 (16) | 0.0125 (18) |
C14A | 0.036 (2) | 0.040 (2) | 0.0482 (19) | 0.0042 (18) | 0.0302 (17) | 0.0038 (19) |
C15A | 0.042 (2) | 0.037 (2) | 0.0385 (17) | 0.0002 (18) | 0.0300 (16) | 0.0019 (17) |
C16A | 0.0322 (19) | 0.036 (2) | 0.0312 (16) | 0.0008 (16) | 0.0209 (15) | 0.0038 (16) |
N1A | 0.0366 (17) | 0.0383 (18) | 0.0377 (15) | 0.0030 (15) | 0.0260 (13) | 0.0045 (15) |
N2A | 0.0354 (17) | 0.0377 (17) | 0.0363 (14) | 0.0028 (15) | 0.0233 (14) | 0.0060 (14) |
O3A | 0.0480 (15) | 0.0476 (16) | 0.0490 (13) | 0.0101 (13) | 0.0382 (12) | 0.0144 (13) |
C11B | 0.0268 (18) | 0.0323 (18) | 0.0276 (15) | 0.0016 (16) | 0.0171 (14) | 0.0025 (15) |
C12B | 0.043 (2) | 0.060 (3) | 0.0479 (19) | 0.020 (2) | 0.0355 (17) | 0.020 (2) |
C13B | 0.046 (2) | 0.063 (3) | 0.055 (2) | 0.017 (2) | 0.0408 (19) | 0.021 (2) |
C14B | 0.041 (2) | 0.045 (2) | 0.0453 (19) | 0.0118 (19) | 0.0321 (18) | 0.0130 (19) |
C15B | 0.045 (2) | 0.040 (2) | 0.047 (2) | 0.0094 (19) | 0.0360 (18) | 0.0096 (19) |
C16B | 0.0335 (19) | 0.035 (2) | 0.0288 (16) | 0.0005 (17) | 0.0204 (16) | 0.0005 (15) |
N1B | 0.0375 (18) | 0.0399 (18) | 0.0399 (16) | 0.0116 (15) | 0.0278 (15) | 0.0131 (15) |
N2B | 0.0304 (16) | 0.0399 (17) | 0.0310 (13) | 0.0027 (15) | 0.0186 (13) | 0.0049 (14) |
O3B | 0.0552 (16) | 0.0534 (17) | 0.0552 (14) | 0.0211 (14) | 0.0454 (13) | 0.0226 (14) |
Geometric parameters (Å, º) top
C1A—O2A | 1.220 (3) | C8B—C9B | 1.375 (4) |
C1A—O1A | 1.317 (4) | C8B—H8B | 0.95 |
C1A—C2A | 1.517 (4) | C9B—C10B | 1.382 (5) |
C2A—C5A | 1.523 (4) | C9B—H9B | 0.95 |
C2A—C3A | 1.529 (5) | C10B—H10B | 0.95 |
C2A—H2A | 1 | O1B—H1B | 1.04 (3) |
C3A—H3A1 | 0.98 | C11A—C15A | 1.378 (4) |
C3A—H3A2 | 0.98 | C11A—C12A | 1.390 (4) |
C3A—H3A3 | 0.98 | C11A—C16A | 1.512 (5) |
C5A—C6A | 1.386 (4) | C12A—C13A | 1.380 (5) |
C5A—C10A | 1.392 (5) | C12A—H12A | 0.95 |
C6A—C7A | 1.384 (5) | C13A—N2A | 1.326 (4) |
C6A—H6A | 0.95 | C13A—H13A | 0.95 |
C7A—C8A | 1.378 (5) | C14A—N2A | 1.333 (4) |
C7A—H7A | 0.95 | C14A—C15A | 1.378 (5) |
C8A—C9A | 1.378 (5) | C14A—H14A | 0.95 |
C8A—H8A | 0.95 | C15A—H15A | 0.95 |
C9A—C10A | 1.378 (5) | C16A—O3A | 1.241 (3) |
C9A—H9A | 0.95 | C16A—N1A | 1.327 (4) |
C10A—H10A | 0.95 | N1A—H1AS | 1.09 (3) |
O1A—H1A | 0.99 (4) | N1A—H1AA | 0.88 (3) |
C1B—O2B | 1.215 (4) | C11B—C15B | 1.367 (4) |
C1B—O1B | 1.310 (3) | C11B—C12B | 1.373 (4) |
C1B—C2B | 1.523 (4) | C11B—C16B | 1.508 (5) |
C2B—C5B | 1.522 (4) | C12B—C13B | 1.381 (5) |
C2B—C3B | 1.522 (5) | C12B—H12B | 0.95 |
C2B—H2B | 1 | C13B—N2B | 1.325 (4) |
C3B—H3B1 | 0.98 | C13B—H13B | 0.95 |
C3B—H3B2 | 0.98 | C14B—N2B | 1.332 (4) |
C3B—H3B3 | 0.98 | C14B—C15B | 1.381 (5) |
C5B—C6B | 1.373 (4) | C14B—H14B | 0.95 |
C5B—C10B | 1.393 (5) | C15B—H15B | 0.95 |
C6B—C7B | 1.395 (5) | C16B—O3B | 1.236 (3) |
C6B—H6B | 0.95 | C16B—N1B | 1.322 (4) |
C7B—C8B | 1.376 (5) | N1B—H1BS | 0.86 (4) |
C7B—H7B | 0.95 | N1B—H1BA | 0.96 (3) |
| | | |
O2A—C1A—O1A | 122.9 (3) | C8B—C7B—H7B | 119.8 |
O2A—C1A—C2A | 124.8 (3) | C6B—C7B—H7B | 119.8 |
O1A—C1A—C2A | 112.4 (3) | C9B—C8B—C7B | 119.8 (3) |
C1A—C2A—C5A | 108.2 (3) | C9B—C8B—H8B | 120.1 |
C1A—C2A—C3A | 111.6 (3) | C7B—C8B—H8B | 120.1 |
C5A—C2A—C3A | 112.0 (2) | C8B—C9B—C10B | 120.0 (3) |
C1A—C2A—H2A | 108.3 | C8B—C9B—H9B | 120 |
C5A—C2A—H2A | 108.3 | C10B—C9B—H9B | 120 |
C3A—C2A—H2A | 108.3 | C9B—C10B—C5B | 120.7 (3) |
C2A—C3A—H3A1 | 109.5 | C9B—C10B—H10B | 119.6 |
C2A—C3A—H3A2 | 109.5 | C5B—C10B—H10B | 119.6 |
H3A1—C3A—H3A2 | 109.5 | C1B—O1B—H1B | 114.7 (17) |
C2A—C3A—H3A3 | 109.5 | C15A—C11A—C12A | 117.8 (3) |
H3A1—C3A—H3A3 | 109.5 | C15A—C11A—C16A | 117.9 (3) |
H3A2—C3A—H3A3 | 109.5 | C12A—C11A—C16A | 124.3 (3) |
C6A—C5A—C10A | 117.5 (3) | C13A—C12A—C11A | 118.5 (3) |
C6A—C5A—C2A | 121.2 (3) | C13A—C12A—H12A | 120.8 |
C10A—C5A—C2A | 121.3 (3) | C11A—C12A—H12A | 120.8 |
C7A—C6A—C5A | 121.5 (3) | N2A—C13A—C12A | 124.1 (3) |
C7A—C6A—H6A | 119.3 | N2A—C13A—H13A | 117.9 |
C5A—C6A—H6A | 119.3 | C12A—C13A—H13A | 117.9 |
C8A—C7A—C6A | 120.0 (4) | N2A—C14A—C15A | 123.4 (3) |
C8A—C7A—H7A | 120 | N2A—C14A—H14A | 118.3 |
C6A—C7A—H7A | 120 | C15A—C14A—H14A | 118.3 |
C9A—C8A—C7A | 119.5 (3) | C14A—C15A—C11A | 119.4 (3) |
C9A—C8A—H8A | 120.2 | C14A—C15A—H15A | 120.3 |
C7A—C8A—H8A | 120.2 | C11A—C15A—H15A | 120.3 |
C8A—C9A—C10A | 120.3 (3) | O3A—C16A—N1A | 122.8 (3) |
C8A—C9A—H9A | 119.9 | O3A—C16A—C11A | 118.6 (3) |
C10A—C9A—H9A | 119.9 | N1A—C16A—C11A | 118.6 (3) |
C9A—C10A—C5A | 121.3 (3) | C16A—N1A—H1AS | 118.2 (16) |
C9A—C10A—H10A | 119.3 | C16A—N1A—H1AA | 124 (2) |
C5A—C10A—H10A | 119.3 | H1AS—N1A—H1AA | 117 (3) |
C1A—O1A—H1A | 109.9 (19) | C13A—N2A—C14A | 116.8 (3) |
O2B—C1B—O1B | 122.7 (3) | C15B—C11B—C12B | 117.8 (3) |
O2B—C1B—C2B | 123.5 (3) | C15B—C11B—C16B | 118.2 (3) |
O1B—C1B—C2B | 113.8 (3) | C12B—C11B—C16B | 124.0 (3) |
C5B—C2B—C3B | 114.2 (3) | C11B—C12B—C13B | 119.0 (3) |
C5B—C2B—C1B | 107.7 (3) | C11B—C12B—H12B | 120.5 |
C3B—C2B—C1B | 111.1 (2) | C13B—C12B—H12B | 120.5 |
C5B—C2B—H2B | 107.9 | N2B—C13B—C12B | 123.5 (3) |
C3B—C2B—H2B | 107.9 | N2B—C13B—H13B | 118.2 |
C1B—C2B—H2B | 107.9 | C12B—C13B—H13B | 118.2 |
C2B—C3B—H3B1 | 109.5 | N2B—C14B—C15B | 122.5 (3) |
C2B—C3B—H3B2 | 109.5 | N2B—C14B—H14B | 118.7 |
H3B1—C3B—H3B2 | 109.5 | C15B—C14B—H14B | 118.7 |
C2B—C3B—H3B3 | 109.5 | C11B—C15B—C14B | 119.9 (3) |
H3B1—C3B—H3B3 | 109.5 | C11B—C15B—H15B | 120 |
H3B2—C3B—H3B3 | 109.5 | C14B—C15B—H15B | 120 |
C6B—C5B—C10B | 118.9 (3) | O3B—C16B—N1B | 123.2 (3) |
C6B—C5B—C2B | 122.1 (3) | O3B—C16B—C11B | 118.6 (3) |
C10B—C5B—C2B | 118.9 (3) | N1B—C16B—C11B | 118.2 (3) |
C5B—C6B—C7B | 120.2 (3) | C16B—N1B—H1BS | 119 (2) |
C5B—C6B—H6B | 119.9 | C16B—N1B—H1BA | 126 (2) |
C7B—C6B—H6B | 119.9 | H1BS—N1B—H1BA | 115 (3) |
C8B—C7B—C6B | 120.3 (4) | C13B—N2B—C14B | 117.2 (3) |
| | | |
O2A—C1A—C2A—C5A | −96.8 (4) | C7B—C8B—C9B—C10B | −0.5 (5) |
O1A—C1A—C2A—C5A | 82.2 (3) | C8B—C9B—C10B—C5B | 0.3 (5) |
O2A—C1A—C2A—C3A | 26.9 (5) | C6B—C5B—C10B—C9B | 0.5 (5) |
O1A—C1A—C2A—C3A | −154.1 (3) | C2B—C5B—C10B—C9B | 178.4 (3) |
C1A—C2A—C5A—C6A | −105.0 (4) | C15A—C11A—C12A—C13A | −0.3 (5) |
C3A—C2A—C5A—C6A | 131.6 (3) | C16A—C11A—C12A—C13A | 180.0 (3) |
C1A—C2A—C5A—C10A | 73.1 (4) | C11A—C12A—C13A—N2A | 1.0 (6) |
C3A—C2A—C5A—C10A | −50.4 (4) | N2A—C14A—C15A—C11A | 0.6 (5) |
C10A—C5A—C6A—C7A | −0.1 (5) | C12A—C11A—C15A—C14A | −0.5 (5) |
C2A—C5A—C6A—C7A | 178.0 (3) | C16A—C11A—C15A—C14A | 179.3 (3) |
C5A—C6A—C7A—C8A | 0.7 (6) | C15A—C11A—C16A—O3A | −5.0 (5) |
C6A—C7A—C8A—C9A | −0.9 (6) | C12A—C11A—C16A—O3A | 174.7 (3) |
C7A—C8A—C9A—C10A | 0.7 (6) | C15A—C11A—C16A—N1A | 176.1 (3) |
C8A—C9A—C10A—C5A | −0.2 (5) | C12A—C11A—C16A—N1A | −4.1 (5) |
C6A—C5A—C10A—C9A | −0.1 (5) | C12A—C13A—N2A—C14A | −0.9 (5) |
C2A—C5A—C10A—C9A | −178.3 (3) | C15A—C14A—N2A—C13A | 0.1 (5) |
O2B—C1B—C2B—C5B | 96.3 (4) | C15B—C11B—C12B—C13B | 0.6 (5) |
O1B—C1B—C2B—C5B | −82.7 (3) | C16B—C11B—C12B—C13B | 178.9 (3) |
O2B—C1B—C2B—C3B | −137.9 (4) | C11B—C12B—C13B—N2B | −0.2 (6) |
O1B—C1B—C2B—C3B | 43.1 (4) | C12B—C11B—C15B—C14B | −0.1 (5) |
C3B—C2B—C5B—C6B | −18.2 (4) | C16B—C11B—C15B—C14B | −178.5 (3) |
C1B—C2B—C5B—C6B | 105.7 (3) | N2B—C14B—C15B—C11B | −0.7 (5) |
C3B—C2B—C5B—C10B | 164.0 (3) | C15B—C11B—C16B—O3B | 0.6 (5) |
C1B—C2B—C5B—C10B | −72.1 (3) | C12B—C11B—C16B—O3B | −177.7 (3) |
C10B—C5B—C6B—C7B | −1.1 (5) | C15B—C11B—C16B—N1B | −178.9 (3) |
C2B—C5B—C6B—C7B | −179.0 (3) | C12B—C11B—C16B—N1B | 2.8 (5) |
C5B—C6B—C7B—C8B | 0.9 (5) | C12B—C13B—N2B—C14B | −0.6 (6) |
C6B—C7B—C8B—C9B | −0.1 (6) | C15B—C14B—N2B—C13B | 1.1 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···N2A | 0.99 (4) | 1.65 (4) | 2.635 (4) | 173 (3) |
O1B—H1B···N2B | 1.04 (3) | 1.59 (4) | 2.628 (3) | 178 (3) |
N1A—H1AS···O3B | 1.09 (3) | 1.80 (3) | 2.883 (4) | 171 (3) |
N1A—H1AA···O2Ai | 0.88 (3) | 2.15 (3) | 3.022 (3) | 171 (3) |
N1B—H1BS···O3A | 0.86 (4) | 2.02 (4) | 2.873 (4) | 175 (3) |
N1B—H1BA···O2Bii | 0.96 (3) | 1.97 (3) | 2.911 (3) | 170 (3) |
Symmetry codes: (i) −x+1, y+1, −z+2; (ii) −x+1, y−1, −z+1. |
(VII) ((
RS)-2-phenylbutyric acid).(iso-nicotinamide)
top
Crystal data top
C10H12O2·C6H6N2O | Z = 2 |
Mr = 286.32 | F(000) = 304 |
Triclinic, P1 | Dx = 1.313 Mg m−3 |
Hall symbol: -P 1 | Melting point: 377 K |
a = 5.7543 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.6867 (8) Å | Cell parameters from 12733 reflections |
c = 13.7434 (12) Å | θ = 0.4–28.7° |
α = 102.056 (5)° | µ = 0.09 mm−1 |
β = 93.206 (4)° | T = 173 K |
γ = 103.524 (5)° | Block, colourless |
V = 723.95 (11) Å3 | 0.4 × 0.16 × 0.13 mm |
Data collection top
Nonius KappaCCD area-detector diffractometer | 2674 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.061 |
2.0° φ and ω scans | θmax = 28.0°, θmin = 3.0° |
Absorption correction: integration Bruker XPREP (Bruker, 1999) | h = −7→6 |
Tmin = 0.970, Tmax = 0.994 | k = −12→12 |
12417 measured reflections | l = −18→18 |
3488 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H 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 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1 | 1.0993 (2) | 1.27176 (13) | 0.27501 (9) | 0.0223 (3) | |
C2 | 1.2119 (2) | 1.37726 (13) | 0.21221 (9) | 0.0230 (3) | |
H2 | 1.1204 | 1.454 | 0.2175 | 0.028* | |
C3 | 1.4736 (2) | 1.45377 (14) | 0.25103 (10) | 0.0272 (3) | |
H3A | 1.4834 | 1.5026 | 0.3226 | 0.033* | |
H3B | 1.5686 | 1.38 | 0.2461 | 0.033* | |
C4 | 1.5827 (3) | 1.56634 (15) | 0.19302 (11) | 0.0341 (3) | |
H4A | 1.576 | 1.5183 | 0.1223 | 0.051* | |
H4B | 1.7506 | 1.6121 | 0.2204 | 0.051* | |
H4C | 1.4919 | 1.641 | 0.199 | 0.051* | |
C5 | 1.1762 (2) | 1.29438 (13) | 0.10261 (9) | 0.0233 (3) | |
C6 | 1.0000 (3) | 1.31167 (16) | 0.03669 (10) | 0.0314 (3) | |
H6 | 0.9041 | 1.3768 | 0.0597 | 0.038* | |
C7 | 0.9617 (3) | 1.23514 (17) | −0.06253 (11) | 0.0370 (3) | |
H7 | 0.8397 | 1.248 | −0.1068 | 0.044* | |
C8 | 1.1004 (3) | 1.14029 (16) | −0.09719 (11) | 0.0335 (3) | |
H8 | 1.0745 | 1.088 | −0.1651 | 0.04* | |
C9 | 1.2771 (3) | 1.12223 (16) | −0.03219 (11) | 0.0358 (3) | |
H9 | 1.3728 | 1.0571 | −0.0555 | 0.043* | |
C10 | 1.3155 (3) | 1.19900 (15) | 0.06721 (10) | 0.0312 (3) | |
H10 | 1.4379 | 1.1862 | 0.1113 | 0.037* | |
O1 | 0.86748 (17) | 1.21733 (11) | 0.24787 (7) | 0.0296 (2) | |
H1 | 0.802 (3) | 1.1491 (19) | 0.2822 (13) | 0.036* | |
O2 | 1.20778 (18) | 1.23927 (11) | 0.34169 (8) | 0.0349 (3) | |
C11 | 0.3800 (2) | 0.78402 (13) | 0.41102 (9) | 0.0205 (3) | |
C12 | 0.6229 (2) | 0.84249 (14) | 0.44203 (10) | 0.0247 (3) | |
H12 | 0.7031 | 0.8073 | 0.4903 | 0.03* | |
C13 | 0.7465 (2) | 0.95373 (14) | 0.40092 (10) | 0.0262 (3) | |
H13 | 0.9131 | 0.9934 | 0.4222 | 0.031* | |
C14 | 0.4102 (2) | 0.94987 (14) | 0.30258 (10) | 0.0258 (3) | |
H14 | 0.3352 | 0.9867 | 0.2538 | 0.031* | |
C15 | 0.2726 (2) | 0.83796 (14) | 0.33904 (9) | 0.0243 (3) | |
H15 | 0.1071 | 0.7987 | 0.3151 | 0.029* | |
C16 | 0.2221 (2) | 0.66348 (13) | 0.44988 (9) | 0.0235 (3) | |
N1 | 0.3105 (2) | 0.62706 (13) | 0.52944 (9) | 0.0286 (3) | |
H1S | 0.209 (3) | 0.5544 (18) | 0.5524 (12) | 0.034* | |
H1A | 0.453 (3) | 0.6752 (18) | 0.5621 (12) | 0.034* | |
N2 | 0.6436 (2) | 1.00800 (12) | 0.33303 (8) | 0.0244 (3) | |
O3 | 0.01871 (18) | 0.60392 (11) | 0.40584 (8) | 0.0366 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0244 (6) | 0.0228 (6) | 0.0194 (6) | 0.0056 (5) | 0.0022 (5) | 0.0042 (5) |
C2 | 0.0245 (7) | 0.0223 (6) | 0.0237 (6) | 0.0059 (5) | 0.0027 (5) | 0.0085 (5) |
C3 | 0.0279 (7) | 0.0243 (6) | 0.0272 (7) | 0.0032 (5) | 0.0007 (5) | 0.0051 (5) |
C4 | 0.0336 (8) | 0.0282 (7) | 0.0365 (8) | −0.0010 (6) | 0.0052 (6) | 0.0082 (6) |
C5 | 0.0237 (6) | 0.0222 (6) | 0.0233 (6) | 0.0005 (5) | 0.0038 (5) | 0.0092 (5) |
C6 | 0.0302 (7) | 0.0373 (8) | 0.0282 (7) | 0.0115 (6) | 0.0028 (6) | 0.0074 (6) |
C7 | 0.0351 (8) | 0.0486 (9) | 0.0265 (7) | 0.0116 (7) | −0.0042 (6) | 0.0081 (6) |
C8 | 0.0382 (8) | 0.0360 (7) | 0.0215 (6) | 0.0029 (6) | 0.0036 (6) | 0.0032 (6) |
C9 | 0.0421 (9) | 0.0332 (8) | 0.0340 (8) | 0.0141 (7) | 0.0071 (6) | 0.0058 (6) |
C10 | 0.0350 (8) | 0.0324 (7) | 0.0282 (7) | 0.0109 (6) | −0.0004 (6) | 0.0093 (6) |
O1 | 0.0241 (5) | 0.0355 (5) | 0.0311 (5) | 0.0015 (4) | 0.0022 (4) | 0.0184 (4) |
O2 | 0.0305 (5) | 0.0406 (6) | 0.0348 (6) | 0.0028 (4) | −0.0040 (4) | 0.0200 (5) |
C11 | 0.0226 (6) | 0.0195 (6) | 0.0183 (6) | 0.0036 (5) | 0.0030 (5) | 0.0034 (5) |
C12 | 0.0226 (6) | 0.0280 (6) | 0.0232 (6) | 0.0039 (5) | −0.0004 (5) | 0.0087 (5) |
C13 | 0.0214 (6) | 0.0304 (7) | 0.0249 (7) | 0.0014 (5) | 0.0011 (5) | 0.0081 (5) |
C14 | 0.0291 (7) | 0.0253 (6) | 0.0228 (6) | 0.0050 (5) | −0.0009 (5) | 0.0082 (5) |
C15 | 0.0225 (6) | 0.0244 (6) | 0.0241 (6) | 0.0025 (5) | −0.0012 (5) | 0.0059 (5) |
C16 | 0.0238 (7) | 0.0226 (6) | 0.0228 (6) | 0.0025 (5) | 0.0019 (5) | 0.0064 (5) |
N1 | 0.0260 (6) | 0.0297 (6) | 0.0279 (6) | −0.0027 (5) | −0.0020 (5) | 0.0143 (5) |
N2 | 0.0262 (6) | 0.0241 (5) | 0.0212 (5) | 0.0021 (4) | 0.0024 (4) | 0.0061 (4) |
O3 | 0.0267 (5) | 0.0411 (6) | 0.0378 (6) | −0.0078 (4) | −0.0074 (4) | 0.0209 (5) |
Geometric parameters (Å, º) top
C1—O2 | 1.2153 (15) | C9—C10 | 1.390 (2) |
C1—O1 | 1.3152 (16) | C9—H9 | 0.95 |
C1—C2 | 1.5265 (17) | C10—H10 | 0.95 |
C2—C3 | 1.5248 (18) | O1—H1 | 0.914 (19) |
C2—C5 | 1.5294 (17) | C11—C12 | 1.3853 (18) |
C2—H2 | 1 | C11—C15 | 1.3900 (17) |
C3—C4 | 1.5224 (19) | C11—C16 | 1.5143 (17) |
C3—H3A | 0.99 | C12—C13 | 1.3880 (18) |
C3—H3B | 0.99 | C12—H12 | 0.95 |
C4—H4A | 0.98 | C13—N2 | 1.3365 (17) |
C4—H4B | 0.98 | C13—H13 | 0.95 |
C4—H4C | 0.98 | C14—N2 | 1.3342 (17) |
C5—C6 | 1.3843 (19) | C14—C15 | 1.3869 (18) |
C5—C10 | 1.3912 (19) | C14—H14 | 0.95 |
C6—C7 | 1.388 (2) | C15—H15 | 0.95 |
C6—H6 | 0.95 | C16—O3 | 1.2359 (16) |
C7—C8 | 1.382 (2) | C16—N1 | 1.3275 (17) |
C7—H7 | 0.95 | N1—H1S | 0.925 (18) |
C8—C9 | 1.382 (2) | N1—H1A | 0.886 (18) |
C8—H8 | 0.95 | | |
| | | |
O2—C1—O1 | 123.06 (12) | C9—C8—H8 | 120.3 |
O2—C1—C2 | 125.04 (12) | C7—C8—H8 | 120.3 |
O1—C1—C2 | 111.90 (10) | C8—C9—C10 | 120.31 (13) |
C3—C2—C1 | 112.04 (10) | C8—C9—H9 | 119.8 |
C3—C2—C5 | 113.61 (11) | C10—C9—H9 | 119.8 |
C1—C2—C5 | 108.45 (10) | C9—C10—C5 | 120.52 (13) |
C3—C2—H2 | 107.5 | C9—C10—H10 | 119.7 |
C1—C2—H2 | 107.5 | C5—C10—H10 | 119.7 |
C5—C2—H2 | 107.5 | C1—O1—H1 | 112.0 (10) |
C4—C3—C2 | 112.43 (11) | C12—C11—C15 | 118.41 (11) |
C4—C3—H3A | 109.1 | C12—C11—C16 | 124.27 (11) |
C2—C3—H3A | 109.1 | C15—C11—C16 | 117.32 (11) |
C4—C3—H3B | 109.1 | C11—C12—C13 | 118.42 (12) |
C2—C3—H3B | 109.1 | C11—C12—H12 | 120.8 |
H3A—C3—H3B | 107.8 | C13—C12—H12 | 120.8 |
C3—C4—H4A | 109.5 | N2—C13—C12 | 123.54 (12) |
C3—C4—H4B | 109.5 | N2—C13—H13 | 118.2 |
H4A—C4—H4B | 109.5 | C12—C13—H13 | 118.2 |
C3—C4—H4C | 109.5 | N2—C14—C15 | 122.82 (12) |
H4A—C4—H4C | 109.5 | N2—C14—H14 | 118.6 |
H4B—C4—H4C | 109.5 | C15—C14—H14 | 118.6 |
C6—C5—C10 | 118.60 (12) | C14—C15—C11 | 119.10 (12) |
C6—C5—C2 | 120.08 (12) | C14—C15—H15 | 120.5 |
C10—C5—C2 | 121.31 (11) | C11—C15—H15 | 120.5 |
C5—C6—C7 | 120.91 (13) | O3—C16—N1 | 123.52 (12) |
C5—C6—H6 | 119.5 | O3—C16—C11 | 118.48 (11) |
C7—C6—H6 | 119.5 | N1—C16—C11 | 118.00 (11) |
C8—C7—C6 | 120.20 (13) | C16—N1—H1S | 116.2 (10) |
C8—C7—H7 | 119.9 | C16—N1—H1A | 121.8 (11) |
C6—C7—H7 | 119.9 | H1S—N1—H1A | 121.7 (14) |
C9—C8—C7 | 119.46 (13) | C14—N2—C13 | 117.69 (11) |
| | | |
O2—C1—C2—C3 | −7.26 (18) | C8—C9—C10—C5 | 0.3 (2) |
O1—C1—C2—C3 | 173.45 (10) | C6—C5—C10—C9 | −0.4 (2) |
O2—C1—C2—C5 | 118.94 (14) | C2—C5—C10—C9 | 178.63 (12) |
O1—C1—C2—C5 | −60.35 (13) | C15—C11—C12—C13 | 1.03 (18) |
C1—C2—C3—C4 | −176.32 (11) | C16—C11—C12—C13 | −179.45 (12) |
C5—C2—C3—C4 | 60.34 (14) | C11—C12—C13—N2 | 0.2 (2) |
C3—C2—C5—C6 | −131.88 (13) | N2—C14—C15—C11 | 0.6 (2) |
C1—C2—C5—C6 | 102.84 (14) | C12—C11—C15—C14 | −1.37 (18) |
C3—C2—C5—C10 | 49.13 (16) | C16—C11—C15—C14 | 179.07 (11) |
C1—C2—C5—C10 | −76.15 (15) | C12—C11—C16—O3 | −168.58 (12) |
C10—C5—C6—C7 | 0.3 (2) | C15—C11—C16—O3 | 10.94 (18) |
C2—C5—C6—C7 | −178.67 (13) | C12—C11—C16—N1 | 11.12 (19) |
C5—C6—C7—C8 | −0.2 (2) | C15—C11—C16—N1 | −169.35 (12) |
C6—C7—C8—C9 | 0.1 (2) | C15—C14—N2—C13 | 0.63 (19) |
C7—C8—C9—C10 | −0.1 (2) | C12—C13—N2—C14 | −1.00 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2 | 0.91 (2) | 1.75 (2) | 2.661 (2) | 172 (2) |
N1—H1S···O3i | 0.93 (2) | 1.98 (2) | 2.902 (2) | 177 (2) |
N1—H1A···O2ii | 0.89 (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·C6H6N2O | Z = 2 |
Mr = 286.32 | F(000) = 304 |
Triclinic, P1 | Dx = 1.299 Mg m−3 |
Hall symbol: P 1 | Melting point: 361 K |
a = 5.6984 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.7762 (10) Å | Cell parameters from 18331 reflections |
c = 13.8553 (13) Å | θ = 0.4–28.3° |
α = 100.011 (3)° | µ = 0.09 mm−1 |
β = 94.302 (5)° | T = 173 K |
γ = 103.919 (5)° | Plate, colourless |
V = 732.26 (11) Å3 | 0.21 × 0.09 × 0.03 mm |
Data collection top
Nonius KappaCCD area-detector diffractometer | 2350 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.073 |
2.0° φ and ω scans | θmax = 28°, θmin = 2.2° |
Absorption correction: integration Bruker XPREP (Bruker, 1999) | h = −7→7 |
Tmin = 0.983, Tmax = 0.997 | k = −12→12 |
18175 measured reflections | l = −18→18 |
3541 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.109 | H 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 parameters | Δρmax = 0.18 e Å−3 |
3 restraints | Δρmin = −0.22 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1A | 1.8863 (6) | 1.4248 (4) | 0.2156 (2) | 0.0315 (7) | |
C2A | 2.0644 (6) | 1.4978 (4) | 0.1523 (2) | 0.0348 (7) | |
H2A | 2.2249 | 1.4792 | 0.1713 | 0.042* | |
C3A | 2.0990 (7) | 1.6594 (4) | 0.1803 (3) | 0.0443 (8) | |
H3A1 | 2.1343 | 1.6899 | 0.253 | 0.053* | |
H3A2 | 1.9457 | 1.6829 | 0.1596 | 0.053* | |
C4A | 2.3071 (8) | 1.7438 (4) | 0.1324 (3) | 0.0550 (10) | |
H4A1 | 2.4609 | 1.7248 | 0.1554 | 0.082* | |
H4A2 | 2.3194 | 1.8469 | 0.151 | 0.082* | |
H4A3 | 2.2738 | 1.7135 | 0.0604 | 0.082* | |
C5A | 1.9964 (5) | 1.4355 (3) | 0.0422 (2) | 0.0315 (7) | |
C6A | 1.8067 (6) | 1.4643 (4) | −0.0140 (3) | 0.0386 (8) | |
H6A | 1.7169 | 1.5268 | 0.016 | 0.046* | |
C7A | 1.7493 (6) | 1.4026 (4) | −0.1128 (3) | 0.0420 (9) | |
H7A | 1.6202 | 1.4227 | −0.1506 | 0.05* | |
C8A | 1.8781 (6) | 1.3117 (4) | −0.1570 (3) | 0.0410 (9) | |
H8A | 1.8362 | 1.2682 | −0.225 | 0.049* | |
C9A | 2.0674 (7) | 1.2838 (4) | −0.1029 (3) | 0.0436 (9) | |
H9A | 2.1575 | 1.2219 | −0.1335 | 0.052* | |
C10A | 2.1261 (6) | 1.3460 (4) | −0.0039 (3) | 0.0390 (8) | |
H10A | 2.2577 | 1.3269 | 0.0331 | 0.047* | |
O1A | 1.6596 (4) | 1.3758 (3) | 0.17604 (18) | 0.0434 (6) | |
H1A | 1.564 (7) | 1.323 (4) | 0.218 (3) | 0.052* | |
O2A | 1.9539 (4) | 1.4127 (3) | 0.29776 (19) | 0.0510 (7) | |
C1B | −0.3343 (5) | −0.0976 (3) | 0.6660 (2) | 0.0280 (7) | |
C2B | −0.4460 (5) | −0.2040 (3) | 0.7276 (2) | 0.0273 (7) | |
H2B | −0.3523 | −0.2788 | 0.7234 | 0.033* | |
C3B | −0.7118 (5) | −0.2808 (3) | 0.6887 (2) | 0.0310 (7) | |
H3B1 | −0.7225 | −0.3262 | 0.6183 | 0.037* | |
H3B2 | −0.8092 | −0.2092 | 0.693 | 0.037* | |
C4B | −0.8200 (6) | −0.3959 (4) | 0.7464 (3) | 0.0411 (8) | |
H4B1 | −0.7218 | −0.4659 | 0.7439 | 0.062* | |
H4B2 | −0.9874 | −0.4451 | 0.717 | 0.062* | |
H4B3 | −0.82 | −0.3506 | 0.8153 | 0.062* | |
C5B | −0.4123 (5) | −0.1273 (3) | 0.8348 (2) | 0.0270 (7) | |
C6B | −0.2392 (6) | −0.1479 (4) | 0.9032 (2) | 0.0368 (8) | |
H6B | −0.1435 | −0.2126 | 0.8831 | 0.044* | |
C7B | −0.2048 (6) | −0.0748 (4) | 1.0007 (3) | 0.0447 (9) | |
H7B | −0.0848 | −0.0894 | 1.0464 | 0.054* | |
C8B | −0.3421 (6) | 0.0181 (4) | 1.0318 (3) | 0.0390 (9) | |
H8B | −0.3181 | 0.0678 | 1.0985 | 0.047* | |
C9B | −0.5164 (6) | 0.0387 (4) | 0.9644 (3) | 0.0405 (9) | |
H9B | −0.6122 | 0.103 | 0.9851 | 0.049* | |
C10B | −0.5517 (6) | −0.0340 (4) | 0.8673 (2) | 0.0352 (8) | |
H10B | −0.6733 | −0.0197 | 0.8222 | 0.042* | |
O1B | −0.0987 (4) | −0.0435 (2) | 0.69316 (17) | 0.0348 (6) | |
H1B | −0.025 (6) | 0.029 (4) | 0.657 (3) | 0.042* | |
O2B | −0.4458 (4) | −0.0612 (3) | 0.60057 (18) | 0.0397 (6) | |
C11A | 1.1220 (5) | 0.9745 (3) | 0.3541 (2) | 0.0254 (7) | |
C12A | 1.3681 (5) | 1.0364 (3) | 0.3871 (2) | 0.0319 (7) | |
H12A | 1.4483 | 1.0056 | 0.4387 | 0.038* | |
C13A | 1.4926 (6) | 1.1435 (4) | 0.3429 (2) | 0.0335 (8) | |
H13A | 1.6597 | 1.1863 | 0.3663 | 0.04* | |
C14A | 1.1582 (6) | 1.1285 (3) | 0.2371 (2) | 0.0332 (8) | |
H14A | 1.0842 | 1.1595 | 0.1841 | 0.04* | |
C15A | 1.0182 (6) | 1.0222 (3) | 0.2765 (2) | 0.0330 (8) | |
H15A | 0.8517 | 0.9815 | 0.251 | 0.04* | |
C16A | 0.9634 (6) | 0.8573 (3) | 0.3957 (2) | 0.0294 (7) | |
N1A | 1.0613 (5) | 0.8149 (3) | 0.4720 (2) | 0.0360 (7) | |
H1AS | 0.981 (7) | 0.741 (4) | 0.493 (3) | 0.043* | |
H1AA | 1.225 (7) | 0.857 (4) | 0.506 (3) | 0.043* | |
N2A | 1.3926 (5) | 1.1908 (3) | 0.26920 (19) | 0.0321 (6) | |
O3A | 0.7502 (4) | 0.8062 (3) | 0.35843 (18) | 0.0440 (6) | |
C11B | 0.3813 (5) | 0.3986 (3) | 0.5332 (2) | 0.0255 (7) | |
C12B | 0.1338 (5) | 0.3394 (3) | 0.5038 (2) | 0.0317 (7) | |
H12B | 0.0481 | 0.3767 | 0.4576 | 0.038* | |
C13B | 0.0148 (6) | 0.2252 (4) | 0.5431 (3) | 0.0335 (8) | |
H13B | −0.1538 | 0.184 | 0.5217 | 0.04* | |
C14B | 0.3601 (6) | 0.2292 (4) | 0.6391 (3) | 0.0339 (8) | |
H14B | 0.44 | 0.1919 | 0.6872 | 0.041* | |
C15B | 0.4937 (5) | 0.3423 (3) | 0.6029 (2) | 0.0307 (7) | |
H15B | 0.662 | 0.3814 | 0.6258 | 0.037* | |
C16B | 0.5336 (6) | 0.5214 (4) | 0.4951 (2) | 0.0308 (7) | |
N1B | 0.4400 (5) | 0.5591 (3) | 0.4165 (2) | 0.0378 (7) | |
H1BS | 0.548 (7) | 0.629 (4) | 0.397 (3) | 0.045* | |
H1BA | 0.305 (7) | 0.513 (4) | 0.389 (3) | 0.045* | |
N2B | 0.1236 (5) | 0.1696 (3) | 0.60956 (19) | 0.0312 (6) | |
O3B | 0.7383 (4) | 0.5835 (3) | 0.53946 (17) | 0.0419 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1A | 0.0290 (16) | 0.0338 (18) | 0.0277 (19) | 0.0002 (14) | 0.0011 (14) | 0.0076 (15) |
C2A | 0.0305 (16) | 0.0373 (19) | 0.0347 (18) | 0.0043 (13) | 0.0051 (13) | 0.0078 (15) |
C3A | 0.048 (2) | 0.040 (2) | 0.041 (2) | 0.0044 (16) | 0.0116 (16) | 0.0058 (16) |
C4A | 0.057 (2) | 0.041 (2) | 0.061 (3) | −0.0044 (19) | 0.016 (2) | 0.015 (2) |
C5A | 0.0288 (16) | 0.0328 (18) | 0.0292 (17) | −0.0021 (14) | 0.0036 (13) | 0.0103 (14) |
C6A | 0.0353 (18) | 0.043 (2) | 0.040 (2) | 0.0120 (15) | 0.0084 (15) | 0.0104 (16) |
C7A | 0.0316 (18) | 0.059 (2) | 0.035 (2) | 0.0074 (17) | −0.0020 (14) | 0.0168 (18) |
C8A | 0.036 (2) | 0.051 (2) | 0.030 (2) | −0.0002 (17) | 0.0022 (15) | 0.0096 (17) |
C9A | 0.045 (2) | 0.046 (2) | 0.040 (2) | 0.0140 (17) | 0.0023 (16) | 0.0072 (17) |
C10A | 0.0377 (18) | 0.042 (2) | 0.038 (2) | 0.0094 (16) | 0.0019 (15) | 0.0104 (16) |
O1A | 0.0283 (13) | 0.0601 (16) | 0.0366 (14) | −0.0068 (11) | −0.0026 (10) | 0.0242 (12) |
O2A | 0.0396 (13) | 0.0676 (18) | 0.0390 (15) | −0.0047 (13) | −0.0075 (11) | 0.0236 (13) |
C1B | 0.0300 (17) | 0.0276 (18) | 0.0267 (17) | 0.0077 (14) | 0.0032 (13) | 0.0055 (14) |
C2B | 0.0227 (14) | 0.0286 (17) | 0.0302 (17) | 0.0034 (13) | 0.0005 (12) | 0.0104 (13) |
C3B | 0.0248 (15) | 0.0291 (17) | 0.0368 (17) | 0.0020 (12) | 0.0020 (12) | 0.0077 (14) |
C4B | 0.0349 (18) | 0.038 (2) | 0.044 (2) | −0.0024 (15) | 0.0031 (15) | 0.0088 (16) |
C5B | 0.0258 (15) | 0.0256 (16) | 0.0290 (17) | 0.0015 (12) | 0.0036 (12) | 0.0109 (13) |
C6B | 0.0332 (17) | 0.045 (2) | 0.0336 (19) | 0.0131 (15) | 0.0019 (14) | 0.0086 (16) |
C7B | 0.0357 (18) | 0.063 (2) | 0.034 (2) | 0.0126 (18) | −0.0056 (15) | 0.0113 (18) |
C8B | 0.042 (2) | 0.040 (2) | 0.030 (2) | 0.0018 (17) | 0.0027 (16) | 0.0053 (16) |
C9B | 0.045 (2) | 0.040 (2) | 0.038 (2) | 0.0139 (17) | 0.0074 (16) | 0.0075 (16) |
C10B | 0.0383 (19) | 0.0369 (19) | 0.0312 (19) | 0.0109 (15) | −0.0006 (14) | 0.0096 (15) |
O1B | 0.0245 (11) | 0.0415 (14) | 0.0382 (14) | 0.0005 (10) | 0.0028 (10) | 0.0189 (11) |
O2B | 0.0333 (12) | 0.0463 (15) | 0.0399 (13) | 0.0033 (11) | −0.0022 (10) | 0.0220 (11) |
C11A | 0.0292 (16) | 0.0227 (16) | 0.0239 (16) | 0.0060 (13) | 0.0042 (13) | 0.0041 (13) |
C12A | 0.0274 (16) | 0.0336 (18) | 0.0320 (18) | 0.0037 (14) | −0.0025 (13) | 0.0077 (15) |
C13A | 0.0281 (17) | 0.040 (2) | 0.0287 (18) | 0.0010 (15) | 0.0007 (13) | 0.0093 (15) |
C14A | 0.0339 (18) | 0.0310 (18) | 0.0316 (19) | 0.0004 (15) | −0.0025 (14) | 0.0118 (15) |
C15A | 0.0283 (17) | 0.0349 (19) | 0.0316 (18) | 0.0013 (15) | −0.0032 (13) | 0.0081 (15) |
C16A | 0.0250 (16) | 0.0300 (17) | 0.0298 (17) | −0.0004 (13) | 0.0018 (13) | 0.0082 (14) |
N1A | 0.0326 (16) | 0.0371 (17) | 0.0361 (17) | −0.0007 (14) | −0.0015 (13) | 0.0169 (14) |
N2A | 0.0314 (14) | 0.0347 (16) | 0.0266 (15) | 0.0004 (13) | 0.0020 (11) | 0.0081 (12) |
O3A | 0.0292 (12) | 0.0492 (15) | 0.0481 (15) | −0.0069 (11) | −0.0058 (11) | 0.0235 (12) |
C11B | 0.0244 (16) | 0.0259 (16) | 0.0236 (16) | 0.0023 (14) | 0.0042 (12) | 0.0035 (13) |
C12B | 0.0292 (17) | 0.0362 (19) | 0.0297 (18) | 0.0055 (14) | 0.0020 (13) | 0.0114 (15) |
C13B | 0.0226 (16) | 0.0377 (19) | 0.037 (2) | 0.0008 (15) | 0.0013 (14) | 0.0087 (15) |
C14B | 0.0280 (17) | 0.0349 (19) | 0.0368 (19) | 0.0038 (15) | −0.0008 (14) | 0.0102 (15) |
C15B | 0.0231 (15) | 0.0304 (18) | 0.0362 (19) | 0.0027 (14) | −0.0005 (13) | 0.0079 (15) |
C16B | 0.0274 (17) | 0.0319 (18) | 0.0325 (18) | 0.0042 (14) | 0.0042 (14) | 0.0094 (14) |
N1B | 0.0264 (15) | 0.0417 (18) | 0.0391 (18) | −0.0080 (13) | −0.0039 (13) | 0.0181 (15) |
N2B | 0.0306 (15) | 0.0337 (15) | 0.0277 (15) | 0.0034 (12) | 0.0032 (11) | 0.0085 (12) |
O3B | 0.0303 (12) | 0.0459 (14) | 0.0424 (14) | −0.0082 (11) | −0.0059 (10) | 0.0198 (11) |
Geometric parameters (Å, º) top
C1A—O2A | 1.208 (4) | C6B—H6B | 0.95 |
C1A—O1A | 1.305 (4) | C7B—C8B | 1.371 (5) |
C1A—C2A | 1.520 (5) | C7B—H7B | 0.95 |
C2A—C3A | 1.520 (5) | C8B—C9B | 1.385 (5) |
C2A—C5A | 1.525 (5) | C8B—H8B | 0.95 |
C2A—H2A | 1 | C9B—C10B | 1.383 (5) |
C3A—C4A | 1.538 (5) | C9B—H9B | 0.95 |
C3A—H3A1 | 0.99 | C10B—H10B | 0.95 |
C3A—H3A2 | 0.99 | O1B—H1B | 0.97 (4) |
C4A—H4A1 | 0.98 | C11A—C15A | 1.391 (4) |
C4A—H4A2 | 0.98 | C11A—C12A | 1.393 (4) |
C4A—H4A3 | 0.98 | C11A—C16A | 1.507 (4) |
C5A—C10A | 1.382 (4) | C12A—C13A | 1.381 (5) |
C5A—C6A | 1.396 (4) | C12A—H12A | 0.95 |
C6A—C7A | 1.376 (5) | C13A—N2A | 1.335 (4) |
C6A—H6A | 0.95 | C13A—H13A | 0.95 |
C7A—C8A | 1.377 (5) | C14A—N2A | 1.334 (4) |
C7A—H7A | 0.95 | C14A—C15A | 1.370 (5) |
C8A—C9A | 1.376 (5) | C14A—H14A | 0.95 |
C8A—H8A | 0.95 | C15A—H15A | 0.95 |
C9A—C10A | 1.380 (5) | C16A—O3A | 1.232 (4) |
C9A—H9A | 0.95 | C16A—N1A | 1.332 (4) |
C10A—H10A | 0.95 | N1A—H1AS | 0.87 (4) |
O1A—H1A | 0.95 (4) | N1A—H1AA | 0.97 (4) |
C1B—O2B | 1.219 (4) | C11B—C15B | 1.381 (4) |
C1B—O1B | 1.318 (4) | C11B—C12B | 1.389 (4) |
C1B—C2B | 1.512 (4) | C11B—C16B | 1.503 (5) |
C2B—C5B | 1.518 (4) | C12B—C13B | 1.380 (5) |
C2B—C3B | 1.529 (4) | C12B—H12B | 0.95 |
C2B—H2B | 1 | C13B—N2B | 1.334 (4) |
C3B—C4B | 1.529 (5) | C13B—H13B | 0.95 |
C3B—H3B1 | 0.99 | C14B—N2B | 1.334 (4) |
C3B—H3B2 | 0.99 | C14B—C15B | 1.378 (5) |
C4B—H4B1 | 0.98 | C14B—H14B | 0.95 |
C4B—H4B2 | 0.98 | C15B—H15B | 0.95 |
C4B—H4B3 | 0.98 | C16B—O3B | 1.236 (4) |
C5B—C10B | 1.388 (4) | C16B—N1B | 1.323 (4) |
C5B—C6B | 1.390 (4) | N1B—H1BS | 0.89 (4) |
C6B—C7B | 1.390 (5) | N1B—H1BA | 0.82 (4) |
| | | |
O2A—C1A—O1A | 122.5 (3) | C10B—C5B—C2B | 121.2 (3) |
O2A—C1A—C2A | 121.1 (3) | C6B—C5B—C2B | 120.8 (3) |
O1A—C1A—C2A | 116.3 (3) | C5B—C6B—C7B | 120.7 (3) |
C3A—C2A—C1A | 108.8 (3) | C5B—C6B—H6B | 119.7 |
C3A—C2A—C5A | 114.5 (3) | C7B—C6B—H6B | 119.7 |
C1A—C2A—C5A | 113.2 (3) | C8B—C7B—C6B | 120.8 (3) |
C3A—C2A—H2A | 106.6 | C8B—C7B—H7B | 119.6 |
C1A—C2A—H2A | 106.6 | C6B—C7B—H7B | 119.6 |
C5A—C2A—H2A | 106.6 | C7B—C8B—C9B | 119.1 (3) |
C2A—C3A—C4A | 112.4 (3) | C7B—C8B—H8B | 120.5 |
C2A—C3A—H3A1 | 109.1 | C9B—C8B—H8B | 120.5 |
C4A—C3A—H3A1 | 109.1 | C10B—C9B—C8B | 120.4 (3) |
C2A—C3A—H3A2 | 109.1 | C10B—C9B—H9B | 119.8 |
C4A—C3A—H3A2 | 109.1 | C8B—C9B—H9B | 119.8 |
H3A1—C3A—H3A2 | 107.9 | C9B—C10B—C5B | 121.1 (3) |
C3A—C4A—H4A1 | 109.5 | C9B—C10B—H10B | 119.5 |
C3A—C4A—H4A2 | 109.5 | C5B—C10B—H10B | 119.5 |
H4A1—C4A—H4A2 | 109.5 | C1B—O1B—H1B | 113 (2) |
C3A—C4A—H4A3 | 109.5 | C15A—C11A—C12A | 117.7 (3) |
H4A1—C4A—H4A3 | 109.5 | C15A—C11A—C16A | 118.2 (3) |
H4A2—C4A—H4A3 | 109.5 | C12A—C11A—C16A | 124.1 (3) |
C10A—C5A—C6A | 118.5 (3) | C13A—C12A—C11A | 118.4 (3) |
C10A—C5A—C2A | 118.8 (3) | C13A—C12A—H12A | 120.8 |
C6A—C5A—C2A | 122.7 (3) | C11A—C12A—H12A | 120.8 |
C7A—C6A—C5A | 120.3 (3) | N2A—C13A—C12A | 124.1 (3) |
C7A—C6A—H6A | 119.9 | N2A—C13A—H13A | 118 |
C5A—C6A—H6A | 119.9 | C12A—C13A—H13A | 118 |
C6A—C7A—C8A | 120.3 (3) | N2A—C14A—C15A | 123.6 (3) |
C6A—C7A—H7A | 119.8 | N2A—C14A—H14A | 118.2 |
C8A—C7A—H7A | 119.8 | C15A—C14A—H14A | 118.2 |
C9A—C8A—C7A | 120.0 (4) | C14A—C15A—C11A | 119.4 (3) |
C9A—C8A—H8A | 120 | C14A—C15A—H15A | 120.3 |
C7A—C8A—H8A | 120 | C11A—C15A—H15A | 120.3 |
C8A—C9A—C10A | 119.8 (3) | O3A—C16A—N1A | 123.2 (3) |
C8A—C9A—H9A | 120.1 | O3A—C16A—C11A | 118.8 (3) |
C10A—C9A—H9A | 120.1 | N1A—C16A—C11A | 118.0 (3) |
C9A—C10A—C5A | 121.0 (3) | C16A—N1A—H1AS | 120 (3) |
C9A—C10A—H10A | 119.5 | C16A—N1A—H1AA | 125 (2) |
C5A—C10A—H10A | 119.5 | H1AS—N1A—H1AA | 114 (3) |
C1A—O1A—H1A | 111 (2) | C14A—N2A—C13A | 116.9 (3) |
O2B—C1B—O1B | 122.8 (3) | C15B—C11B—C12B | 117.8 (3) |
O2B—C1B—C2B | 125.2 (3) | C15B—C11B—C16B | 118.0 (3) |
O1B—C1B—C2B | 112.0 (2) | C12B—C11B—C16B | 124.2 (3) |
C1B—C2B—C5B | 108.9 (2) | C13B—C12B—C11B | 118.7 (3) |
C1B—C2B—C3B | 112.3 (2) | C13B—C12B—H12B | 120.6 |
C5B—C2B—C3B | 112.9 (2) | C11B—C12B—H12B | 120.6 |
C1B—C2B—H2B | 107.5 | N2B—C13B—C12B | 123.5 (3) |
C5B—C2B—H2B | 107.5 | N2B—C13B—H13B | 118.2 |
C3B—C2B—H2B | 107.5 | C12B—C13B—H13B | 118.2 |
C2B—C3B—C4B | 112.4 (3) | N2B—C14B—C15B | 122.9 (3) |
C2B—C3B—H3B1 | 109.1 | N2B—C14B—H14B | 118.6 |
C4B—C3B—H3B1 | 109.1 | C15B—C14B—H14B | 118.6 |
C2B—C3B—H3B2 | 109.1 | C14B—C15B—C11B | 119.6 (3) |
C4B—C3B—H3B2 | 109.1 | C14B—C15B—H15B | 120.2 |
H3B1—C3B—H3B2 | 107.8 | C11B—C15B—H15B | 120.2 |
C3B—C4B—H4B1 | 109.5 | O3B—C16B—N1B | 123.3 (3) |
C3B—C4B—H4B2 | 109.5 | O3B—C16B—C11B | 118.5 (3) |
H4B1—C4B—H4B2 | 109.5 | N1B—C16B—C11B | 118.2 (3) |
C3B—C4B—H4B3 | 109.5 | C16B—N1B—H1BS | 112 (2) |
H4B1—C4B—H4B3 | 109.5 | C16B—N1B—H1BA | 119 (3) |
H4B2—C4B—H4B3 | 109.5 | H1BS—N1B—H1BA | 129 (4) |
C10B—C5B—C6B | 118.0 (3) | C13B—N2B—C14B | 117.4 (3) |
| | | |
O2A—C1A—C2A—C3A | −83.7 (4) | C5B—C6B—C7B—C8B | 0.6 (5) |
O1A—C1A—C2A—C3A | 96.7 (3) | C6B—C7B—C8B—C9B | −0.1 (6) |
O2A—C1A—C2A—C5A | 147.8 (3) | C7B—C8B—C9B—C10B | 0.2 (6) |
O1A—C1A—C2A—C5A | −31.7 (4) | C8B—C9B—C10B—C5B | −0.8 (5) |
C1A—C2A—C3A—C4A | 170.6 (3) | C6B—C5B—C10B—C9B | 1.3 (5) |
C5A—C2A—C3A—C4A | −61.6 (4) | C2B—C5B—C10B—C9B | −178.3 (3) |
C3A—C2A—C5A—C10A | 130.3 (3) | C15A—C11A—C12A—C13A | 1.7 (4) |
C1A—C2A—C5A—C10A | −104.2 (3) | C16A—C11A—C12A—C13A | −179.7 (3) |
C3A—C2A—C5A—C6A | −50.3 (4) | C11A—C12A—C13A—N2A | −0.9 (5) |
C1A—C2A—C5A—C6A | 75.2 (4) | N2A—C14A—C15A—C11A | −0.1 (5) |
C10A—C5A—C6A—C7A | 1.0 (5) | C12A—C11A—C15A—C14A | −1.2 (4) |
C2A—C5A—C6A—C7A | −178.5 (3) | C16A—C11A—C15A—C14A | −179.9 (3) |
C5A—C6A—C7A—C8A | 0.1 (5) | C15A—C11A—C16A—O3A | 1.5 (4) |
C6A—C7A—C8A—C9A | −0.9 (6) | C12A—C11A—C16A—O3A | −177.1 (3) |
C7A—C8A—C9A—C10A | 0.7 (6) | C15A—C11A—C16A—N1A | −178.0 (3) |
C8A—C9A—C10A—C5A | 0.4 (6) | C12A—C11A—C16A—N1A | 3.4 (4) |
C6A—C5A—C10A—C9A | −1.2 (5) | C15A—C14A—N2A—C13A | 0.9 (5) |
C2A—C5A—C10A—C9A | 178.2 (3) | C12A—C13A—N2A—C14A | −0.4 (5) |
O2B—C1B—C2B—C5B | −116.9 (3) | C15B—C11B—C12B—C13B | −2.0 (4) |
O1B—C1B—C2B—C5B | 61.1 (3) | C16B—C11B—C12B—C13B | 179.0 (3) |
O2B—C1B—C2B—C3B | 8.9 (4) | C11B—C12B—C13B—N2B | 1.2 (5) |
O1B—C1B—C2B—C3B | −173.0 (3) | N2B—C14B—C15B—C11B | 0.2 (5) |
C1B—C2B—C3B—C4B | 176.0 (3) | C12B—C11B—C15B—C14B | 1.3 (4) |
C5B—C2B—C3B—C4B | −60.4 (3) | C16B—C11B—C15B—C14B | −179.6 (3) |
C1B—C2B—C5B—C10B | 74.6 (3) | C15B—C11B—C16B—O3B | −12.8 (4) |
C3B—C2B—C5B—C10B | −50.8 (4) | C12B—C11B—C16B—O3B | 166.2 (3) |
C1B—C2B—C5B—C6B | −105.0 (3) | C15B—C11B—C16B—N1B | 168.2 (3) |
C3B—C2B—C5B—C6B | 129.6 (3) | C12B—C11B—C16B—N1B | −12.8 (5) |
C10B—C5B—C6B—C7B | −1.2 (5) | C12B—C13B—N2B—C14B | 0.3 (5) |
C2B—C5B—C6B—C7B | 178.4 (3) | C15B—C14B—N2B—C13B | −1.0 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···N2A | 0.95 (4) | 1.72 (4) | 2.653 (4) | 165 (4) |
O1B—H1B···N2B | 0.97 (4) | 1.69 (4) | 2.661 (4) | 172 (3) |
N1A—H1AS···O3B | 0.87 (4) | 2.03 (4) | 2.893 (4) | 169 (3) |
N1A—H1AA···O2Bi | 0.97 (4) | 2.10 (4) | 3.065 (4) | 171 (3) |
N1B—H1BS···O3A | 0.89 (4) | 2.02 (4) | 2.905 (4) | 170 (3) |
N1B—H1BA···O2Aii | 0.82 (4) | 2.20 (4) | 3.003 (4) | 170 (4) |
Symmetry codes: (i) x+2, y+1, z; (ii) x−2, y−1, z. |
(IX) ((
S)-2-phenylbutyric acid).(iso-nicotinamide)
top
Crystal data top
C10H12O2·C6H6N2O | Z = 2 |
Mr = 286.32 | F(000) = 304 |
Triclinic, P1 | Dx = 1.3 Mg m−3 |
Hall symbol: P 1 | Melting point: 361 K |
a = 5.7059 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.7727 (4) Å | Cell parameters from 18951 reflections |
c = 13.8321 (7) Å | θ = 0.4–28.3° |
α = 100.323 (3)° | µ = 0.09 mm−1 |
β = 94.090 (2)° | T = 173 K |
γ = 103.881 (3)° | Block, colourless |
V = 731.36 (6) Å3 | 0.47 × 0.2 × 0.09 mm |
Data collection top
Nonius KappaCCD area-detector diffractometer | 3151 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.068 |
2.0° φ and ω scans | θmax = 28°, θmin = 3.4° |
Absorption correction: integration Bruker XPREP (Bruker, 1999) | h = −7→7 |
Tmin = 0.953, Tmax = 0.992 | k = −12→12 |
18714 measured reflections | l = −18→18 |
3529 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.151 | H 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 parameters | Δρmax = 0.78 e Å−3 |
3 restraints | Δρmin = −0.27 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1A | −0.8824 (6) | −0.4274 (3) | 0.7841 (2) | 0.0321 (6) | |
C2A | −1.0648 (6) | −0.4973 (4) | 0.8485 (2) | 0.0384 (7) | |
H2A | −1.224 | −0.4771 | 0.8301 | 0.046* | |
C3A | −1.0988 (8) | −0.6603 (4) | 0.8191 (3) | 0.0473 (8) | |
H3A1 | −0.9467 | −0.6845 | 0.8402 | 0.057* | |
H3A2 | −1.1333 | −0.6909 | 0.7462 | 0.057* | |
C4A | −1.3115 (9) | −0.7427 (4) | 0.8679 (3) | 0.0532 (10) | |
H4A1 | −1.4629 | −0.7212 | 0.8454 | 0.08* | |
H4A2 | −1.2774 | −0.7124 | 0.9401 | 0.08* | |
H4A3 | −1.3281 | −0.8465 | 0.849 | 0.08* | |
C5A | −0.9925 (6) | −0.4372 (3) | 0.9583 (2) | 0.0357 (7) | |
C6A | −0.8009 (6) | −0.4654 (4) | 1.0146 (3) | 0.0412 (7) | |
H6A | −0.7096 | −0.5271 | 0.9841 | 0.049* | |
C7A | −0.7454 (6) | −0.4032 (4) | 1.1143 (2) | 0.0386 (7) | |
H7A | −0.6182 | −0.4235 | 1.153 | 0.046* | |
C8A | −0.8763 (6) | −0.3116 (4) | 1.1571 (2) | 0.0374 (7) | |
H8A | −0.8355 | −0.2668 | 1.2251 | 0.045* | |
C9A | −1.0637 (7) | −0.2844 (4) | 1.1031 (3) | 0.0434 (8) | |
H9A | −1.1539 | −0.2223 | 1.1338 | 0.052* | |
C10A | −1.1220 (7) | −0.3473 (4) | 1.0036 (3) | 0.0417 (7) | |
H10A | −1.2526 | −0.3283 | 0.9663 | 0.05* | |
O1A | −0.6557 (4) | −0.3786 (3) | 0.82201 (17) | 0.0418 (6) | |
H1A | −0.575 (9) | −0.321 (5) | 0.787 (3) | 0.05* | |
O2A | −0.9572 (5) | −0.4127 (3) | 0.70373 (19) | 0.0487 (6) | |
C1B | 1.3344 (5) | 1.0972 (3) | 0.3337 (2) | 0.0256 (5) | |
C2B | 1.4471 (4) | 1.2045 (3) | 0.27201 (19) | 0.0222 (5) | |
H2B | 1.3538 | 1.2795 | 0.2765 | 0.027* | |
C3B | 1.7133 (5) | 1.2811 (3) | 0.3114 (2) | 0.0267 (5) | |
H3B1 | 1.7237 | 1.3272 | 0.382 | 0.032* | |
H3B2 | 1.8105 | 1.2093 | 0.3071 | 0.032* | |
C4B | 1.8195 (6) | 1.3951 (3) | 0.2532 (2) | 0.0364 (7) | |
H4B1 | 1.7241 | 1.4666 | 0.2576 | 0.055* | |
H4B2 | 1.8143 | 1.3493 | 0.1837 | 0.055* | |
H4B3 | 1.9885 | 1.4427 | 0.2808 | 0.055* | |
C5B | 1.4123 (5) | 1.1266 (3) | 0.16454 (19) | 0.0246 (5) | |
C6B | 1.2391 (5) | 1.1464 (4) | 0.0965 (2) | 0.0336 (6) | |
H6B | 1.1434 | 1.2111 | 0.1172 | 0.04* | |
C7B | 1.2031 (6) | 1.0727 (4) | −0.0019 (2) | 0.0421 (7) | |
H7B | 1.0825 | 1.0867 | −0.0474 | 0.051* | |
C8B | 1.3420 (6) | 0.9802 (4) | −0.0328 (2) | 0.0370 (7) | |
H8B | 1.3184 | 0.9306 | −0.0999 | 0.044* | |
C9B | 1.5170 (6) | 0.9592 (4) | 0.0338 (2) | 0.0370 (7) | |
H9B | 1.6122 | 0.8945 | 0.0126 | 0.044* | |
C10B | 1.5533 (6) | 1.0330 (3) | 0.1318 (2) | 0.0315 (6) | |
H10B | 1.6754 | 1.0195 | 0.1769 | 0.038* | |
O1B | 1.1004 (4) | 1.0436 (2) | 0.30739 (16) | 0.0317 (5) | |
H1B | 1.027 (7) | 1.006 (4) | 0.349 (3) | 0.038* | |
O2B | 1.4456 (4) | 1.0613 (3) | 0.39959 (17) | 0.0369 (5) | |
C11A | −0.1255 (5) | 0.0271 (3) | 0.64573 (19) | 0.0233 (5) | |
C12A | −0.3707 (5) | −0.0339 (3) | 0.6133 (2) | 0.0293 (6) | |
H12A | −0.4511 | −0.0024 | 0.5623 | 0.035* | |
C13A | −0.4955 (5) | −0.1424 (3) | 0.6572 (2) | 0.0311 (6) | |
H13A | −0.6626 | −0.1848 | 0.6343 | 0.037* | |
C14A | −0.1609 (5) | −0.1288 (3) | 0.7625 (2) | 0.0300 (6) | |
H14A | −0.088 | −0.1597 | 0.8157 | 0.036* | |
C15A | −0.0189 (5) | −0.0212 (3) | 0.7223 (2) | 0.0296 (6) | |
H15A | 0.1481 | 0.0187 | 0.7467 | 0.035* | |
C16A | 0.0339 (5) | 0.1445 (3) | 0.6047 (2) | 0.0285 (6) | |
N1A | −0.0632 (5) | 0.1866 (3) | 0.52813 (19) | 0.0316 (5) | |
H1AS | 0.011 (8) | 0.252 (5) | 0.510 (3) | 0.038* | |
H1AA | −0.232 (8) | 0.146 (4) | 0.494 (3) | 0.038* | |
N2A | −0.3938 (5) | −0.1903 (3) | 0.72990 (18) | 0.0295 (5) | |
O3A | 0.2463 (4) | 0.1961 (3) | 0.64189 (18) | 0.0438 (6) | |
C11B | 0.6188 (5) | 0.6023 (3) | 0.4671 (2) | 0.0240 (5) | |
C12B | 0.8660 (5) | 0.6611 (3) | 0.4972 (2) | 0.0286 (6) | |
H12B | 0.9503 | 0.6242 | 0.544 | 0.034* | |
C13B | 0.9860 (5) | 0.7747 (3) | 0.4572 (2) | 0.0300 (6) | |
H13B | 1.1546 | 0.8153 | 0.4782 | 0.036* | |
C14B | 0.6413 (5) | 0.7719 (3) | 0.3611 (2) | 0.0293 (6) | |
H14B | 0.5621 | 0.8102 | 0.3137 | 0.035* | |
C15B | 0.5056 (5) | 0.6572 (3) | 0.3968 (2) | 0.0283 (6) | |
H15B | 0.3382 | 0.6172 | 0.3733 | 0.034* | |
C16B | 0.4643 (5) | 0.4784 (3) | 0.5048 (2) | 0.0268 (5) | |
N1B | 0.5576 (5) | 0.4426 (3) | 0.5847 (2) | 0.0340 (6) | |
H1BS | 0.437 (8) | 0.380 (5) | 0.604 (3) | 0.041* | |
H1BA | 0.688 (8) | 0.492 (5) | 0.616 (3) | 0.041* | |
N2B | 0.8772 (4) | 0.8304 (2) | 0.39062 (17) | 0.0268 (5) | |
O3B | 0.2612 (4) | 0.4178 (3) | 0.46077 (17) | 0.0379 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1A | 0.0328 (14) | 0.0333 (14) | 0.0243 (13) | −0.0019 (12) | 0.0004 (11) | 0.0061 (11) |
C2A | 0.0366 (15) | 0.0417 (16) | 0.0352 (15) | 0.0070 (13) | 0.0046 (12) | 0.0073 (13) |
C3A | 0.056 (2) | 0.0348 (16) | 0.0444 (19) | −0.0001 (15) | 0.0120 (16) | 0.0049 (13) |
C4A | 0.067 (3) | 0.0344 (17) | 0.050 (2) | −0.0063 (17) | 0.0145 (19) | 0.0100 (15) |
C5A | 0.0360 (16) | 0.0381 (16) | 0.0249 (13) | −0.0085 (13) | 0.0027 (11) | 0.0104 (12) |
C6A | 0.0394 (17) | 0.0480 (19) | 0.0329 (16) | 0.0054 (14) | 0.0076 (13) | 0.0065 (13) |
C7A | 0.0322 (15) | 0.0533 (18) | 0.0300 (15) | 0.0094 (14) | −0.0009 (12) | 0.0116 (13) |
C8A | 0.0369 (16) | 0.0439 (17) | 0.0264 (14) | 0.0021 (14) | 0.0015 (12) | 0.0068 (12) |
C9A | 0.0450 (19) | 0.0452 (18) | 0.0390 (17) | 0.0114 (15) | 0.0021 (14) | 0.0076 (14) |
C10A | 0.0410 (18) | 0.0429 (17) | 0.0383 (17) | 0.0029 (14) | −0.0047 (13) | 0.0151 (14) |
O1A | 0.0354 (12) | 0.0535 (14) | 0.0302 (12) | −0.0079 (10) | −0.0049 (9) | 0.0218 (10) |
O2A | 0.0363 (13) | 0.0617 (16) | 0.0392 (13) | −0.0079 (11) | −0.0094 (10) | 0.0207 (11) |
C1B | 0.0295 (14) | 0.0232 (12) | 0.0243 (12) | 0.0061 (11) | 0.0031 (10) | 0.0062 (10) |
C2B | 0.0203 (11) | 0.0219 (11) | 0.0225 (11) | 0.0002 (9) | 0.0005 (9) | 0.0074 (9) |
C3B | 0.0224 (12) | 0.0273 (12) | 0.0273 (12) | 0.0001 (10) | −0.0011 (9) | 0.0077 (10) |
C4B | 0.0353 (16) | 0.0308 (14) | 0.0367 (16) | −0.0054 (12) | 0.0041 (12) | 0.0095 (12) |
C5B | 0.0246 (12) | 0.0230 (11) | 0.0241 (12) | 0.0004 (10) | 0.0011 (10) | 0.0081 (10) |
C6B | 0.0298 (14) | 0.0437 (16) | 0.0272 (14) | 0.0109 (12) | −0.0014 (11) | 0.0065 (12) |
C7B | 0.0388 (16) | 0.056 (2) | 0.0301 (16) | 0.0136 (15) | −0.0063 (13) | 0.0062 (14) |
C8B | 0.0400 (17) | 0.0381 (16) | 0.0268 (14) | 0.0011 (13) | 0.0013 (12) | 0.0037 (12) |
C9B | 0.0461 (18) | 0.0327 (15) | 0.0329 (16) | 0.0136 (13) | 0.0061 (13) | 0.0034 (12) |
C10B | 0.0351 (15) | 0.0332 (14) | 0.0268 (13) | 0.0109 (12) | −0.0023 (11) | 0.0068 (11) |
O1B | 0.0244 (10) | 0.0380 (11) | 0.0337 (11) | 0.0017 (8) | 0.0018 (8) | 0.0189 (9) |
O2B | 0.0324 (11) | 0.0428 (12) | 0.0356 (11) | 0.0035 (9) | −0.0045 (8) | 0.0201 (9) |
C11A | 0.0241 (13) | 0.0241 (12) | 0.0193 (12) | 0.0024 (10) | 0.0020 (9) | 0.0035 (9) |
C12A | 0.0263 (14) | 0.0322 (14) | 0.0270 (14) | 0.0026 (11) | −0.0012 (11) | 0.0078 (11) |
C13A | 0.0249 (14) | 0.0359 (15) | 0.0271 (14) | −0.0029 (11) | 0.0003 (11) | 0.0082 (11) |
C14A | 0.0324 (15) | 0.0289 (13) | 0.0248 (13) | 0.0011 (12) | −0.0026 (11) | 0.0070 (11) |
C15A | 0.0259 (13) | 0.0294 (14) | 0.0290 (14) | −0.0012 (11) | −0.0020 (11) | 0.0080 (11) |
C16A | 0.0262 (13) | 0.0270 (13) | 0.0278 (13) | −0.0028 (10) | 0.0006 (10) | 0.0076 (10) |
N1A | 0.0294 (13) | 0.0325 (12) | 0.0292 (13) | −0.0039 (10) | −0.0028 (10) | 0.0150 (10) |
N2A | 0.0315 (13) | 0.0309 (12) | 0.0235 (11) | 0.0019 (10) | 0.0030 (9) | 0.0071 (9) |
O3A | 0.0291 (11) | 0.0505 (14) | 0.0450 (13) | −0.0098 (10) | −0.0087 (10) | 0.0247 (11) |
C11B | 0.0253 (14) | 0.0232 (12) | 0.0228 (12) | 0.0050 (10) | 0.0038 (10) | 0.0046 (10) |
C12B | 0.0251 (13) | 0.0340 (15) | 0.0258 (13) | 0.0033 (11) | −0.0008 (10) | 0.0105 (11) |
C13B | 0.0223 (13) | 0.0351 (14) | 0.0294 (14) | 0.0005 (11) | −0.0003 (10) | 0.0088 (11) |
C14B | 0.0302 (14) | 0.0286 (13) | 0.0286 (14) | 0.0047 (11) | −0.0017 (11) | 0.0103 (11) |
C15B | 0.0220 (12) | 0.0300 (14) | 0.0296 (14) | 0.0012 (11) | −0.0029 (10) | 0.0072 (11) |
C16B | 0.0262 (13) | 0.0259 (12) | 0.0270 (13) | 0.0021 (10) | 0.0021 (10) | 0.0083 (10) |
N1B | 0.0295 (13) | 0.0337 (13) | 0.0343 (14) | −0.0049 (11) | −0.0033 (11) | 0.0158 (11) |
N2B | 0.0292 (12) | 0.0257 (11) | 0.0228 (11) | 0.0012 (9) | 0.0015 (9) | 0.0064 (9) |
O3B | 0.0297 (11) | 0.0399 (11) | 0.0375 (12) | −0.0074 (9) | −0.0066 (9) | 0.0173 (9) |
Geometric parameters (Å, º) top
C1A—O2A | 1.208 (4) | C6B—H6B | 0.95 |
C1A—O1A | 1.301 (4) | C7B—C8B | 1.372 (5) |
C1A—C2A | 1.533 (4) | C7B—H7B | 0.95 |
C2A—C5A | 1.516 (4) | C8B—C9B | 1.387 (5) |
C2A—C3A | 1.533 (5) | C8B—H8B | 0.95 |
C2A—H2A | 1 | C9B—C10B | 1.392 (4) |
C3A—C4A | 1.556 (5) | C9B—H9B | 0.95 |
C3A—H3A1 | 0.99 | C10B—H10B | 0.95 |
C3A—H3A2 | 0.99 | O1B—H1B | 0.83 (4) |
C4A—H4A1 | 0.98 | C11A—C12A | 1.389 (4) |
C4A—H4A2 | 0.98 | C11A—C15A | 1.393 (4) |
C4A—H4A3 | 0.98 | C11A—C16A | 1.507 (4) |
C5A—C10A | 1.374 (5) | C12A—C13A | 1.389 (4) |
C5A—C6A | 1.406 (5) | C12A—H12A | 0.95 |
C6A—C7A | 1.385 (5) | C13A—N2A | 1.335 (4) |
C6A—H6A | 0.95 | C13A—H13A | 0.95 |
C7A—C8A | 1.380 (5) | C14A—N2A | 1.328 (4) |
C7A—H7A | 0.95 | C14A—C15A | 1.391 (4) |
C8A—C9A | 1.366 (5) | C14A—H14A | 0.95 |
C8A—H8A | 0.95 | C15A—H15A | 0.95 |
C9A—C10A | 1.384 (5) | C16A—O3A | 1.230 (4) |
C9A—H9A | 0.95 | C16A—N1A | 1.334 (4) |
C10A—H10A | 0.95 | N1A—H1AS | 0.77 (4) |
O1A—H1A | 0.88 (5) | N1A—H1AA | 1.00 (4) |
C1B—O2B | 1.223 (4) | C11B—C15B | 1.383 (4) |
C1B—O1B | 1.310 (3) | C11B—C12B | 1.391 (4) |
C1B—C2B | 1.522 (3) | C11B—C16B | 1.516 (4) |
C2B—C5B | 1.519 (3) | C12B—C13B | 1.385 (4) |
C2B—C3B | 1.535 (3) | C12B—H12B | 0.95 |
C2B—H2B | 1 | C13B—N2B | 1.338 (4) |
C3B—C4B | 1.525 (4) | C13B—H13B | 0.95 |
C3B—H3B1 | 0.99 | C14B—N2B | 1.332 (4) |
C3B—H3B2 | 0.99 | C14B—C15B | 1.391 (4) |
C4B—H4B1 | 0.98 | C14B—H14B | 0.95 |
C4B—H4B2 | 0.98 | C15B—H15B | 0.95 |
C4B—H4B3 | 0.98 | C16B—O3B | 1.227 (4) |
C5B—C6B | 1.387 (4) | C16B—N1B | 1.330 (4) |
C5B—C10B | 1.395 (4) | N1B—H1BS | 0.90 (5) |
C6B—C7B | 1.397 (4) | N1B—H1BA | 0.82 (5) |
| | | |
O2A—C1A—O1A | 123.2 (3) | C6B—C5B—C2B | 120.9 (2) |
O2A—C1A—C2A | 118.8 (3) | C10B—C5B—C2B | 120.8 (2) |
O1A—C1A—C2A | 117.8 (3) | C5B—C6B—C7B | 121.0 (3) |
C5A—C2A—C3A | 113.8 (3) | C5B—C6B—H6B | 119.5 |
C5A—C2A—C1A | 113.2 (3) | C7B—C6B—H6B | 119.5 |
C3A—C2A—C1A | 107.0 (3) | C8B—C7B—C6B | 120.0 (3) |
C5A—C2A—H2A | 107.5 | C8B—C7B—H7B | 120 |
C3A—C2A—H2A | 107.5 | C6B—C7B—H7B | 120 |
C1A—C2A—H2A | 107.5 | C7B—C8B—C9B | 119.9 (3) |
C2A—C3A—C4A | 110.9 (3) | C7B—C8B—H8B | 120 |
C2A—C3A—H3A1 | 109.5 | C9B—C8B—H8B | 120 |
C4A—C3A—H3A1 | 109.5 | C8B—C9B—C10B | 120.0 (3) |
C2A—C3A—H3A2 | 109.5 | C8B—C9B—H9B | 120 |
C4A—C3A—H3A2 | 109.5 | C10B—C9B—H9B | 120 |
H3A1—C3A—H3A2 | 108 | C9B—C10B—C5B | 120.7 (3) |
C3A—C4A—H4A1 | 109.5 | C9B—C10B—H10B | 119.7 |
C3A—C4A—H4A2 | 109.5 | C5B—C10B—H10B | 119.7 |
H4A1—C4A—H4A2 | 109.5 | C1B—O1B—H1B | 114 (3) |
C3A—C4A—H4A3 | 109.5 | C12A—C11A—C15A | 118.2 (2) |
H4A1—C4A—H4A3 | 109.5 | C12A—C11A—C16A | 124.4 (2) |
H4A2—C4A—H4A3 | 109.5 | C15A—C11A—C16A | 117.3 (2) |
C10A—C5A—C6A | 119.1 (3) | C13A—C12A—C11A | 118.3 (3) |
C10A—C5A—C2A | 116.7 (3) | C13A—C12A—H12A | 120.8 |
C6A—C5A—C2A | 124.1 (3) | C11A—C12A—H12A | 120.8 |
C7A—C6A—C5A | 119.9 (3) | N2A—C13A—C12A | 123.7 (3) |
C7A—C6A—H6A | 120 | N2A—C13A—H13A | 118.1 |
C5A—C6A—H6A | 120 | C12A—C13A—H13A | 118.1 |
C8A—C7A—C6A | 119.4 (3) | N2A—C14A—C15A | 123.0 (3) |
C8A—C7A—H7A | 120.3 | N2A—C14A—H14A | 118.5 |
C6A—C7A—H7A | 120.3 | C15A—C14A—H14A | 118.5 |
C9A—C8A—C7A | 120.9 (3) | C14A—C15A—C11A | 118.9 (3) |
C9A—C8A—H8A | 119.5 | C14A—C15A—H15A | 120.5 |
C7A—C8A—H8A | 119.5 | C11A—C15A—H15A | 120.5 |
C8A—C9A—C10A | 120.0 (3) | O3A—C16A—N1A | 122.9 (3) |
C8A—C9A—H9A | 120 | O3A—C16A—C11A | 119.3 (3) |
C10A—C9A—H9A | 120 | N1A—C16A—C11A | 117.8 (3) |
C5A—C10A—C9A | 120.6 (3) | C16A—N1A—H1AS | 119 (3) |
C5A—C10A—H10A | 119.7 | C16A—N1A—H1AA | 126 (2) |
C9A—C10A—H10A | 119.7 | H1AS—N1A—H1AA | 115 (4) |
C1A—O1A—H1A | 110 (3) | C14A—N2A—C13A | 117.7 (3) |
O2B—C1B—O1B | 122.6 (3) | C15B—C11B—C12B | 118.7 (2) |
O2B—C1B—C2B | 125.1 (3) | C15B—C11B—C16B | 117.3 (2) |
O1B—C1B—C2B | 112.3 (2) | C12B—C11B—C16B | 124.0 (2) |
C5B—C2B—C1B | 108.4 (2) | C13B—C12B—C11B | 118.3 (3) |
C5B—C2B—C3B | 113.4 (2) | C13B—C12B—H12B | 120.9 |
C1B—C2B—C3B | 112.1 (2) | C11B—C12B—H12B | 120.9 |
C5B—C2B—H2B | 107.6 | N2B—C13B—C12B | 123.5 (3) |
C1B—C2B—H2B | 107.6 | N2B—C13B—H13B | 118.3 |
C3B—C2B—H2B | 107.6 | C12B—C13B—H13B | 118.3 |
C4B—C3B—C2B | 111.6 (2) | N2B—C14B—C15B | 122.9 (3) |
C4B—C3B—H3B1 | 109.3 | N2B—C14B—H14B | 118.5 |
C2B—C3B—H3B1 | 109.3 | C15B—C14B—H14B | 118.5 |
C4B—C3B—H3B2 | 109.3 | C11B—C15B—C14B | 118.9 (3) |
C2B—C3B—H3B2 | 109.3 | C11B—C15B—H15B | 120.6 |
H3B1—C3B—H3B2 | 108 | C14B—C15B—H15B | 120.6 |
C3B—C4B—H4B1 | 109.5 | O3B—C16B—N1B | 124.0 (3) |
C3B—C4B—H4B2 | 109.5 | O3B—C16B—C11B | 118.4 (3) |
H4B1—C4B—H4B2 | 109.5 | N1B—C16B—C11B | 117.6 (3) |
C3B—C4B—H4B3 | 109.5 | C16B—N1B—H1BS | 107 (3) |
H4B1—C4B—H4B3 | 109.5 | C16B—N1B—H1BA | 121 (3) |
H4B2—C4B—H4B3 | 109.5 | H1BS—N1B—H1BA | 129 (4) |
C6B—C5B—C10B | 118.3 (3) | C14B—N2B—C13B | 117.7 (2) |
| | | |
O2A—C1A—C2A—C5A | −146.6 (3) | C5B—C6B—C7B—C8B | −0.7 (5) |
O1A—C1A—C2A—C5A | 29.2 (4) | C6B—C7B—C8B—C9B | 0.4 (5) |
O2A—C1A—C2A—C3A | 87.2 (4) | C7B—C8B—C9B—C10B | −0.6 (5) |
O1A—C1A—C2A—C3A | −97.0 (4) | C8B—C9B—C10B—C5B | 1.1 (5) |
C5A—C2A—C3A—C4A | 63.4 (4) | C6B—C5B—C10B—C9B | −1.4 (4) |
C1A—C2A—C3A—C4A | −170.8 (3) | C2B—C5B—C10B—C9B | 178.5 (3) |
C3A—C2A—C5A—C10A | −131.4 (3) | C15A—C11A—C12A—C13A | −1.5 (4) |
C1A—C2A—C5A—C10A | 106.1 (3) | C16A—C11A—C12A—C13A | 179.5 (3) |
C3A—C2A—C5A—C6A | 50.0 (4) | C11A—C12A—C13A—N2A | 0.8 (5) |
C1A—C2A—C5A—C6A | −72.5 (4) | N2A—C14A—C15A—C11A | 1.4 (4) |
C10A—C5A—C6A—C7A | 0.2 (5) | C12A—C11A—C15A—C14A | 0.5 (4) |
C2A—C5A—C6A—C7A | 178.8 (3) | C16A—C11A—C15A—C14A | 179.6 (3) |
C5A—C6A—C7A—C8A | −1.3 (5) | C12A—C11A—C16A—O3A | 176.5 (3) |
C6A—C7A—C8A—C9A | 1.7 (5) | C15A—C11A—C16A—O3A | −2.5 (4) |
C7A—C8A—C9A—C10A | −1.0 (6) | C12A—C11A—C16A—N1A | −4.2 (4) |
C6A—C5A—C10A—C9A | 0.5 (5) | C15A—C11A—C16A—N1A | 176.8 (3) |
C2A—C5A—C10A—C9A | −178.2 (3) | C15A—C14A—N2A—C13A | −2.1 (4) |
C8A—C9A—C10A—C5A | −0.1 (6) | C12A—C13A—N2A—C14A | 1.0 (5) |
O2B—C1B—C2B—C5B | 117.6 (3) | C15B—C11B—C12B—C13B | 1.7 (4) |
O1B—C1B—C2B—C5B | −61.4 (3) | C16B—C11B—C12B—C13B | −179.7 (3) |
O2B—C1B—C2B—C3B | −8.3 (4) | C11B—C12B—C13B—N2B | −0.5 (5) |
O1B—C1B—C2B—C3B | 172.7 (2) | C12B—C11B—C15B—C14B | −2.0 (4) |
C5B—C2B—C3B—C4B | 60.5 (3) | C16B—C11B—C15B—C14B | 179.4 (3) |
C1B—C2B—C3B—C4B | −176.4 (2) | N2B—C14B—C15B—C11B | 1.0 (4) |
C1B—C2B—C5B—C6B | 104.7 (3) | C15B—C11B—C16B—O3B | 11.7 (4) |
C3B—C2B—C5B—C6B | −130.1 (3) | C12B—C11B—C16B—O3B | −166.8 (3) |
C1B—C2B—C5B—C10B | −75.1 (3) | C15B—C11B—C16B—N1B | −167.8 (3) |
C3B—C2B—C5B—C10B | 50.0 (3) | C12B—C11B—C16B—N1B | 13.7 (4) |
C10B—C5B—C6B—C7B | 1.2 (5) | C15B—C14B—N2B—C13B | 0.3 (4) |
C2B—C5B—C6B—C7B | −178.7 (3) | C12B—C13B—N2B—C14B | −0.5 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···N2A | 0.88 (5) | 1.78 (5) | 2.652 (3) | 173 (4) |
O1B—H1B···N2B | 0.83 (4) | 1.93 (4) | 2.662 (3) | 147 (4) |
N1A—H1AS···O3B | 0.77 (4) | 2.13 (5) | 2.897 (3) | 171 (4) |
N1A—H1AA···O2Bi | 1.00 (4) | 2.08 (4) | 3.062 (3) | 169 (3) |
N1B—H1BS···O3A | 0.90 (5) | 2.04 (5) | 2.901 (3) | 160 (4) |
N1B—H1BA···O2Aii | 0.82 (5) | 2.19 (5) | 3.002 (4) | 170 (4) |
Symmetry codes: (i) x−2, y−1, z; (ii) x+2, y+1, z. |