organic compounds
Conformational isomers in (2RS,3SR,6SR)-3-ethyl-2,6-diphenyl-1-phenylacetyl-4-piperidone determined from synchrotron data at 120 K
aSchool of Chemistry, Bharathidasan University, Tiruchirappalli, Tamil Nadu 620 024, India, bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, and cSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland
*Correspondence e-mail: cg@st-andrews.ac.uk
In the title compound, C27H27NO2, the conformations of the two independent molecules differ in the shape of the piperidone rings, the orientation of the N-acyl substituents and the axial/equatorial disposition of the ethyl and phenyl groups. The molecules are linked into complex chains by four independent C—H⋯O hydrogen bonds.
Comment
In piperidone derivatives containing N-chloroacetyl or N-ethoxycarbonyl substituents, the piperidone rings generally adopt distorted boat conformations (Ponnuswamy et al., 2002; Nallini et al., 2003). This study of the title compound, (I) (Figs. 1 and 2), was undertaken to investigate the effect of an N-phenylacetyl substituent upon the molecular conformation of the piperidone ring.
Compound (I) forms extremely small crystals of rather indifferent quality, and synchrotron radiation was necessary to obtain usable diffraction data. It crystallizes with Z′ = 2 in the P21/c (Figs. 1 and 2): molecules 1 and 2 contain atoms N11 and N21, respectively. The conformations of the two independent molecules are significantly different. Firstly, the ring-puckering parameters (Cremer & Pople, 1975) for the piperidone rings are, for the atom sequences Nn1—Cn2—Cn3—Cn4—Cn5—Cn6, θ = 94.0 (8)° and φ = 254.6 (8)° when n = 1, and θ = 88.3 (7)° and φ = 124.1 (7)° when n = 2, indicating an almost ideal twist-boat conformation in molecule 2, but a conformation midway between boat and twist-boat for molecule 1. Secondly, the orientation of the N-acyl substituent is entirely different in the two molecules, as indicated by the leading torsion angles (Table 1). Finally, in molecule 1, the substituents at C12 and C13 are axial and that at C16 is equatorial; in molecule 2 the substituents at C22 and C23 are equatorial and that at C26 is axial (Figs. 1 and 2, and Table 1). The two molecules are thus conformational isomers and this in itself precludes the possibility of any additional crystallographic symmetry.
The molecules are linked into rather complex chains by a combination of four C—H⋯O hydrogen bonds (Table 2). Atoms C22 and C28 in the type 2 molecule at (x, y, z) both act as hydrogen-bond donors to atom O24 in the type 2 molecule at (x, − y, + z), so forming a C(4)C(5)[R21(7)] chain of rings (Bernstein et al., 1995) along [001]. This chain is formed by type 2 molecule only and the type 1 molecules are pendent from it. Atoms C13 and C222 at (x, y, z) act as hydrogen-bond donors respectively to atoms O24 and O14 at (1 − x, 1 − y, 1 − z), so forming a non-centrosymmetric R22(11) ring (Fig. 3). Antiparallel pairs of these chains, related to one another by inversion, are weakly linked by a single C—H⋯π(arene) interaction (Table 2).
Experimental
The title compound was prepared by the condensation of equimolar quantities of phenylacetyl chloride and 3-ethyl-2,6-diphenylpiperidin-4-one in anhydrous benzene, in the presence of triethylamine as the base. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of a solution in aqueous ethanol (m.p. 368–371 K).
Crystal data
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Data collection
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Refinement
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Diffraction data were collected at the Daresbury SRS, station 9.8, UK (Cernik et al., 1997; Clegg, 2000). The very small crystal size and weak diffraction led to a relatively high Rint and to a low 2θmax for the data used in the All H atoms were located in difference maps and then treated as riding atoms, with C—H = 0.95 (aromatic), 0.98 (CH3), 0.99 (CH2) or 1.00 Å (aliphatic CH), and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) for the methyl groups.
Data collection: APEX2 (Bruker, 2003); cell APEX2 and SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).
Supporting information
https://doi.org/10.1107/S1600536806009184/lh2021sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536806009184/lh2021Isup2.hkl
Data collection: APEX2 (Bruker, 2003); cell
APEX2 and SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).C27H27NO2 | F(000) = 1696 |
Mr = 397.50 | Dx = 1.205 Mg m−3 |
Monoclinic, P21/c | Synchrotron radiation, λ = 0.6712 Å |
Hall symbol: -P 2ybc | Cell parameters from 1257 reflections |
a = 19.355 (6) Å | θ = 2.6–18.5° |
b = 22.944 (8) Å | µ = 0.08 mm−1 |
c = 9.959 (3) Å | T = 120 K |
β = 97.905 (6)° | Lath, colourless |
V = 4381 (2) Å3 | 0.08 × 0.02 × 0.002 mm |
Z = 8 |
Bruker SMART APEX2 CCD diffractometer | 2533 reflections with I > 2σ(I) |
Radiation source: Daresbury SRS station 9.8 | Rint = 0.123 |
Silicon 111 monochromator | θmax = 20.7°, θmin = 2.5° |
fine–slice ω scans | h = −19→20 |
16316 measured reflections | k = −24→24 |
5346 independent reflections | l = −10→10 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.108 | H-atom parameters constrained |
wR(F2) = 0.338 | w = 1/[σ2(Fo2) + (0.195P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.002 |
5346 reflections | Δρmax = 0.81 e Å−3 |
526 parameters | Δρmin = −0.29 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.030 (5) |
x | y | z | Uiso*/Ueq | ||
N11 | 0.6763 (3) | 0.3221 (3) | 0.9826 (6) | 0.0563 (19) | |
C12 | 0.6095 (4) | 0.3205 (5) | 1.0347 (8) | 0.069 (3) | |
C111 | 0.5988 (4) | 0.3713 (5) | 1.1295 (8) | 0.075 (3) | |
C116 | 0.6501 (4) | 0.3807 (5) | 1.2418 (9) | 0.088 (3) | |
C115 | 0.6409 (6) | 0.4260 (6) | 1.3317 (10) | 0.104 (4) | |
C114 | 0.5824 (7) | 0.4597 (6) | 1.3165 (11) | 0.110 (4) | |
C113 | 0.5314 (6) | 0.4504 (6) | 1.2081 (12) | 0.118 (4) | |
C112 | 0.5390 (5) | 0.4058 (5) | 1.1154 (11) | 0.101 (4) | |
C13 | 0.5503 (4) | 0.3123 (5) | 0.9160 (9) | 0.071 (3) | |
C137 | 0.5544 (5) | 0.2550 (5) | 0.8515 (10) | 0.079 (3) | |
C138 | 0.5403 (6) | 0.2030 (5) | 0.9362 (11) | 0.104 (4) | |
C14 | 0.5511 (4) | 0.3595 (5) | 0.8117 (9) | 0.082 (3) | |
O14 | 0.4994 (3) | 0.3714 (3) | 0.7273 (6) | 0.099 (2) | |
C15 | 0.6148 (4) | 0.3930 (4) | 0.8189 (8) | 0.075 (3) | |
C16 | 0.6838 (4) | 0.3582 (4) | 0.8596 (8) | 0.058 (2) | |
C121 | 0.7431 (4) | 0.4012 (3) | 0.8795 (8) | 0.054 (2) | |
C122 | 0.7574 (4) | 0.4338 (4) | 1.0009 (8) | 0.059 (2) | |
C123 | 0.8106 (5) | 0.4738 (4) | 1.0139 (10) | 0.070 (3) | |
C124 | 0.8494 (4) | 0.4850 (4) | 0.9134 (10) | 0.063 (2) | |
C125 | 0.8363 (4) | 0.4526 (4) | 0.7949 (9) | 0.062 (2) | |
C126 | 0.7838 (4) | 0.4103 (4) | 0.7785 (8) | 0.060 (2) | |
C17 | 0.7275 (4) | 0.2832 (4) | 1.0293 (8) | 0.054 (2) | |
O17 | 0.7193 (3) | 0.2498 (3) | 1.1245 (6) | 0.0755 (19) | |
C18 | 0.7936 (4) | 0.2809 (3) | 0.9635 (8) | 0.056 (2) | |
C131 | 0.8359 (4) | 0.2263 (4) | 0.9909 (8) | 0.054 (2) | |
C132 | 0.8311 (4) | 0.1809 (4) | 0.8988 (9) | 0.066 (3) | |
C133 | 0.8698 (5) | 0.1317 (4) | 0.9191 (9) | 0.075 (3) | |
C134 | 0.9187 (4) | 0.1258 (4) | 1.0353 (9) | 0.068 (3) | |
C135 | 0.9243 (4) | 0.1694 (4) | 1.1271 (9) | 0.061 (2) | |
C136 | 0.8838 (4) | 0.2203 (4) | 1.1092 (8) | 0.059 (2) | |
N21 | 0.7780 (3) | 0.7033 (3) | 0.3650 (6) | 0.0510 (17) | |
C22 | 0.7804 (4) | 0.6604 (4) | 0.2513 (8) | 0.0643 (13) | |
C211 | 0.8336 (4) | 0.6127 (3) | 0.2872 (8) | 0.048 (2) | |
C212 | 0.8316 (5) | 0.5773 (4) | 0.3979 (8) | 0.061 (2) | |
C213 | 0.8800 (5) | 0.5343 (4) | 0.4243 (9) | 0.072 (3) | |
C214 | 0.9309 (5) | 0.5248 (4) | 0.3449 (10) | 0.068 (3) | |
C215 | 0.9344 (4) | 0.5603 (3) | 0.2308 (8) | 0.056 (2) | |
C216 | 0.8855 (4) | 0.6039 (3) | 0.2027 (8) | 0.050 (2) | |
C23 | 0.7057 (4) | 0.6369 (4) | 0.2075 (8) | 0.0643 (13) | |
C237 | 0.7021 (4) | 0.6025 (4) | 0.0778 (8) | 0.064 (2) | |
C238 | 0.6417 (5) | 0.5574 (5) | 0.0659 (10) | 0.096 (3) | |
C24 | 0.6532 (4) | 0.6883 (4) | 0.1948 (8) | 0.0643 (13) | |
O24 | 0.6163 (3) | 0.6997 (3) | 0.0870 (5) | 0.082 (2) | |
C25 | 0.6523 (4) | 0.7261 (4) | 0.3121 (7) | 0.0643 (13) | |
C26 | 0.7137 (4) | 0.7120 (4) | 0.4259 (7) | 0.057 (2) | |
C221 | 0.7030 (4) | 0.6645 (4) | 0.5269 (7) | 0.062 (2) | |
C226 | 0.7553 (4) | 0.6584 (4) | 0.6401 (8) | 0.063 (2) | |
C225 | 0.7513 (5) | 0.6144 (4) | 0.7334 (9) | 0.072 (3) | |
C224 | 0.6975 (5) | 0.5751 (5) | 0.7195 (9) | 0.088 (3) | |
C223 | 0.6433 (5) | 0.5819 (5) | 0.6104 (9) | 0.095 (4) | |
C222 | 0.6475 (4) | 0.6263 (5) | 0.5169 (8) | 0.080 (3) | |
C27 | 0.8332 (4) | 0.7413 (4) | 0.4046 (8) | 0.052 (2) | |
O27 | 0.8300 (3) | 0.7766 (3) | 0.4954 (5) | 0.0628 (16) | |
C28 | 0.8982 (4) | 0.7358 (3) | 0.3368 (7) | 0.047 (2) | |
C231 | 0.9411 (4) | 0.7912 (4) | 0.3484 (8) | 0.051 (2) | |
C232 | 0.9853 (4) | 0.8049 (4) | 0.4697 (7) | 0.055 (2) | |
C233 | 1.0237 (4) | 0.8554 (4) | 0.4775 (8) | 0.059 (2) | |
C234 | 1.0202 (4) | 0.8941 (4) | 0.3692 (8) | 0.065 (2) | |
C235 | 0.9773 (5) | 0.8794 (4) | 0.2489 (9) | 0.077 (3) | |
C236 | 0.9397 (4) | 0.8286 (4) | 0.2419 (8) | 0.060 (2) | |
H12 | 0.6101 | 0.2844 | 1.0910 | 0.083* | |
H116 | 0.6905 | 0.3567 | 1.2563 | 0.106* | |
H115 | 0.6764 | 0.4335 | 1.4054 | 0.124* | |
H114 | 0.5769 | 0.4895 | 1.3804 | 0.132* | |
H113 | 0.4909 | 0.4743 | 1.1962 | 0.142* | |
H112 | 0.5030 | 0.3990 | 1.0422 | 0.121* | |
H13 | 0.5049 | 0.3145 | 0.9529 | 0.085* | |
H13A | 0.6016 | 0.2507 | 0.8250 | 0.095* | |
H13B | 0.5206 | 0.2544 | 0.7673 | 0.095* | |
H13C | 0.4948 | 0.2074 | 0.9674 | 0.156* | |
H13D | 0.5767 | 0.2001 | 1.0148 | 0.156* | |
H13E | 0.5404 | 0.1674 | 0.8815 | 0.156* | |
H15A | 0.6128 | 0.4249 | 0.8852 | 0.090* | |
H15B | 0.6166 | 0.4111 | 0.7292 | 0.090* | |
H16 | 0.6910 | 0.3314 | 0.7835 | 0.069* | |
H122 | 0.7305 | 0.4281 | 1.0727 | 0.071* | |
H123 | 0.8207 | 0.4946 | 1.0969 | 0.083* | |
H124 | 0.8846 | 0.5142 | 0.9237 | 0.076* | |
H125 | 0.8635 | 0.4592 | 0.7238 | 0.074* | |
H126 | 0.7762 | 0.3878 | 0.6977 | 0.073* | |
H18A | 0.7808 | 0.2851 | 0.8642 | 0.067* | |
H18B | 0.8232 | 0.3147 | 0.9955 | 0.067* | |
H132 | 0.7993 | 0.1844 | 0.8176 | 0.080* | |
H133 | 0.8636 | 0.1011 | 0.8543 | 0.089* | |
H134 | 0.9471 | 0.0920 | 1.0493 | 0.082* | |
H135 | 0.9570 | 0.1655 | 1.2070 | 0.073* | |
H136 | 0.8887 | 0.2502 | 1.1760 | 0.071* | |
H22 | 0.7945 | 0.6824 | 0.1727 | 0.077* | |
H212 | 0.7968 | 0.5828 | 0.4553 | 0.073* | |
H213 | 0.8783 | 0.5101 | 0.5011 | 0.086* | |
H214 | 0.9638 | 0.4943 | 0.3663 | 0.082* | |
H215 | 0.9697 | 0.5545 | 0.1745 | 0.068* | |
H216 | 0.8867 | 0.6282 | 0.1258 | 0.060* | |
H23 | 0.6937 | 0.6101 | 0.2801 | 0.077* | |
H23A | 0.7469 | 0.5819 | 0.0755 | 0.076* | |
H23B | 0.6949 | 0.6295 | −0.0005 | 0.076* | |
H23C | 0.6516 | 0.5280 | 0.1373 | 0.144* | |
H23D | 0.6374 | 0.5385 | −0.0230 | 0.144* | |
H23E | 0.5979 | 0.5774 | 0.0759 | 0.144* | |
H25A | 0.6075 | 0.7212 | 0.3482 | 0.077* | |
H25B | 0.6557 | 0.7673 | 0.2838 | 0.077* | |
H26 | 0.7215 | 0.7486 | 0.4807 | 0.069* | |
H226 | 0.7935 | 0.6848 | 0.6521 | 0.076* | |
H225 | 0.7868 | 0.6113 | 0.8092 | 0.087* | |
H224 | 0.6966 | 0.5440 | 0.7822 | 0.106* | |
H223 | 0.6044 | 0.5563 | 0.6008 | 0.114* | |
H222 | 0.6108 | 0.6305 | 0.4437 | 0.096* | |
H28A | 0.8847 | 0.7262 | 0.2398 | 0.057* | |
H28B | 0.9271 | 0.7033 | 0.3791 | 0.057* | |
H232 | 0.9884 | 0.7793 | 0.5452 | 0.066* | |
H233 | 1.0535 | 0.8642 | 0.5590 | 0.071* | |
H234 | 1.0460 | 0.9294 | 0.3766 | 0.078* | |
H235 | 0.9743 | 0.9045 | 0.1725 | 0.093* | |
H236 | 0.9115 | 0.8190 | 0.1590 | 0.072* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.033 (4) | 0.101 (5) | 0.031 (4) | 0.002 (4) | −0.009 (3) | 0.010 (3) |
C12 | 0.031 (5) | 0.127 (8) | 0.044 (5) | 0.000 (5) | −0.012 (4) | −0.004 (5) |
C111 | 0.042 (5) | 0.134 (9) | 0.045 (5) | −0.002 (5) | −0.009 (4) | −0.014 (6) |
C116 | 0.047 (6) | 0.160 (10) | 0.055 (6) | −0.012 (6) | −0.004 (5) | −0.016 (7) |
C115 | 0.078 (8) | 0.185 (12) | 0.047 (6) | −0.011 (8) | 0.005 (5) | −0.032 (7) |
C114 | 0.102 (9) | 0.154 (12) | 0.075 (8) | 0.012 (9) | 0.014 (7) | −0.044 (7) |
C113 | 0.086 (8) | 0.176 (13) | 0.090 (9) | 0.022 (8) | 0.003 (7) | −0.027 (9) |
C112 | 0.068 (7) | 0.148 (10) | 0.078 (8) | 0.019 (7) | −0.019 (6) | −0.039 (7) |
C13 | 0.046 (5) | 0.110 (8) | 0.051 (6) | −0.004 (5) | −0.007 (4) | −0.014 (6) |
C137 | 0.046 (5) | 0.098 (8) | 0.089 (7) | 0.004 (5) | −0.006 (5) | 0.006 (7) |
C138 | 0.111 (9) | 0.103 (9) | 0.097 (9) | 0.001 (7) | 0.007 (7) | 0.016 (7) |
C14 | 0.046 (6) | 0.158 (10) | 0.037 (5) | 0.009 (6) | −0.016 (4) | 0.000 (6) |
O14 | 0.061 (4) | 0.154 (7) | 0.070 (4) | 0.003 (4) | −0.031 (4) | 0.007 (4) |
C15 | 0.033 (5) | 0.137 (9) | 0.048 (5) | 0.015 (5) | −0.020 (4) | −0.006 (5) |
C16 | 0.041 (5) | 0.094 (7) | 0.034 (5) | 0.004 (4) | −0.008 (4) | 0.002 (4) |
C121 | 0.042 (5) | 0.071 (6) | 0.044 (5) | 0.009 (4) | −0.014 (4) | 0.003 (4) |
C122 | 0.050 (5) | 0.081 (6) | 0.045 (5) | 0.010 (5) | −0.002 (4) | −0.011 (4) |
C123 | 0.055 (6) | 0.082 (7) | 0.066 (6) | 0.013 (5) | −0.012 (5) | −0.011 (5) |
C124 | 0.050 (5) | 0.060 (6) | 0.072 (7) | 0.003 (4) | −0.018 (5) | 0.000 (5) |
C125 | 0.047 (5) | 0.080 (6) | 0.056 (6) | 0.005 (5) | −0.001 (4) | 0.014 (5) |
C126 | 0.053 (5) | 0.086 (7) | 0.039 (5) | 0.016 (5) | −0.005 (4) | 0.011 (4) |
C17 | 0.039 (5) | 0.087 (6) | 0.032 (4) | −0.009 (4) | −0.007 (4) | 0.006 (5) |
O17 | 0.047 (4) | 0.123 (5) | 0.051 (4) | −0.015 (3) | −0.012 (3) | 0.023 (4) |
C18 | 0.050 (5) | 0.068 (6) | 0.046 (5) | −0.006 (4) | −0.009 (4) | 0.012 (4) |
C131 | 0.039 (5) | 0.069 (6) | 0.050 (5) | −0.006 (4) | −0.012 (4) | 0.016 (5) |
C132 | 0.060 (6) | 0.075 (7) | 0.053 (5) | 0.002 (5) | −0.031 (4) | 0.006 (5) |
C133 | 0.080 (6) | 0.069 (6) | 0.064 (6) | 0.013 (5) | −0.028 (5) | −0.004 (5) |
C134 | 0.061 (6) | 0.064 (6) | 0.073 (7) | 0.006 (5) | −0.015 (5) | 0.005 (5) |
C135 | 0.041 (5) | 0.081 (7) | 0.055 (5) | −0.008 (5) | −0.015 (4) | 0.019 (5) |
C136 | 0.054 (5) | 0.075 (6) | 0.045 (5) | −0.007 (5) | −0.008 (4) | 0.006 (4) |
N21 | 0.032 (4) | 0.089 (5) | 0.031 (3) | 0.007 (3) | 0.000 (3) | 0.004 (3) |
C22 | 0.037 (2) | 0.115 (4) | 0.037 (2) | −0.006 (2) | −0.0076 (19) | 0.001 (2) |
C211 | 0.046 (5) | 0.055 (5) | 0.037 (5) | −0.004 (4) | −0.013 (4) | 0.003 (4) |
C212 | 0.076 (6) | 0.069 (6) | 0.034 (5) | 0.005 (5) | −0.006 (4) | −0.001 (4) |
C213 | 0.096 (7) | 0.082 (7) | 0.034 (5) | 0.001 (6) | −0.004 (5) | −0.004 (5) |
C214 | 0.077 (7) | 0.055 (6) | 0.064 (6) | 0.009 (5) | −0.023 (5) | −0.007 (5) |
C215 | 0.055 (5) | 0.053 (5) | 0.054 (5) | −0.002 (4) | −0.017 (4) | −0.007 (4) |
C216 | 0.033 (4) | 0.067 (6) | 0.044 (5) | −0.006 (4) | −0.015 (4) | 0.007 (4) |
C23 | 0.037 (2) | 0.115 (4) | 0.037 (2) | −0.006 (2) | −0.0076 (19) | 0.001 (2) |
C237 | 0.050 (5) | 0.098 (7) | 0.041 (5) | −0.002 (5) | 0.000 (4) | −0.005 (4) |
C238 | 0.072 (7) | 0.127 (9) | 0.082 (7) | −0.017 (6) | −0.014 (5) | −0.036 (6) |
C24 | 0.037 (2) | 0.115 (4) | 0.037 (2) | −0.006 (2) | −0.0076 (19) | 0.001 (2) |
O24 | 0.056 (4) | 0.139 (6) | 0.045 (3) | 0.001 (3) | −0.014 (3) | 0.013 (3) |
C25 | 0.037 (2) | 0.115 (4) | 0.037 (2) | −0.006 (2) | −0.0076 (19) | 0.001 (2) |
C26 | 0.039 (5) | 0.099 (7) | 0.032 (4) | 0.006 (4) | −0.002 (4) | 0.012 (4) |
C221 | 0.032 (5) | 0.120 (8) | 0.031 (5) | −0.003 (5) | −0.004 (4) | 0.004 (5) |
C226 | 0.048 (5) | 0.104 (7) | 0.034 (5) | −0.004 (5) | −0.007 (4) | 0.001 (5) |
C225 | 0.066 (6) | 0.108 (8) | 0.040 (5) | −0.002 (6) | −0.004 (4) | 0.002 (5) |
C224 | 0.097 (8) | 0.123 (9) | 0.041 (6) | −0.022 (7) | −0.002 (5) | 0.016 (5) |
C223 | 0.085 (7) | 0.151 (10) | 0.047 (6) | −0.051 (7) | −0.002 (5) | 0.005 (7) |
C222 | 0.052 (6) | 0.153 (10) | 0.033 (5) | −0.018 (6) | −0.005 (4) | 0.004 (6) |
C27 | 0.041 (5) | 0.076 (6) | 0.036 (5) | 0.006 (4) | −0.011 (4) | 0.016 (5) |
O27 | 0.065 (4) | 0.084 (4) | 0.038 (3) | 0.009 (3) | 0.002 (3) | −0.014 (3) |
C28 | 0.044 (5) | 0.056 (5) | 0.038 (4) | 0.001 (4) | −0.008 (4) | −0.001 (4) |
C231 | 0.034 (4) | 0.069 (6) | 0.045 (5) | 0.006 (4) | −0.007 (4) | −0.012 (4) |
C232 | 0.044 (5) | 0.084 (6) | 0.033 (4) | 0.005 (5) | −0.008 (4) | −0.004 (4) |
C233 | 0.038 (5) | 0.091 (7) | 0.046 (5) | −0.006 (5) | −0.006 (4) | −0.021 (5) |
C234 | 0.056 (5) | 0.080 (6) | 0.053 (6) | −0.007 (5) | −0.015 (4) | −0.001 (5) |
C235 | 0.075 (6) | 0.082 (7) | 0.065 (6) | −0.022 (5) | −0.027 (5) | 0.011 (5) |
C236 | 0.063 (6) | 0.070 (6) | 0.039 (5) | −0.010 (5) | −0.020 (4) | 0.005 (5) |
N11—C17 | 1.366 (10) | N21—C27 | 1.393 (10) |
N11—C12 | 1.457 (9) | N21—C26 | 1.473 (9) |
N11—C16 | 1.502 (9) | N21—C22 | 1.504 (10) |
C12—C111 | 1.531 (13) | C22—C211 | 1.512 (11) |
C12—C13 | 1.541 (10) | C22—C23 | 1.549 (10) |
C12—H12 | 1.00 | C22—H22 | 1.00 |
C111—C112 | 1.393 (13) | C211—C212 | 1.374 (11) |
C111—C116 | 1.407 (11) | C211—C216 | 1.410 (11) |
C116—C115 | 1.400 (14) | C212—C213 | 1.360 (12) |
C116—H116 | 0.95 | C212—H212 | 0.95 |
C115—C114 | 1.362 (14) | C213—C214 | 1.363 (12) |
C115—H115 | 0.95 | C213—H213 | 0.95 |
C114—C113 | 1.376 (15) | C214—C215 | 1.408 (12) |
C114—H114 | 0.95 | C214—H214 | 0.95 |
C113—C112 | 1.399 (15) | C215—C216 | 1.379 (10) |
C113—H113 | 0.95 | C215—H215 | 0.95 |
C112—H112 | 0.95 | C216—H216 | 0.95 |
C13—C137 | 1.469 (12) | C23—C237 | 1.507 (11) |
C13—C14 | 1.501 (13) | C23—C24 | 1.552 (12) |
C13—H13 | 1.00 | C23—H23 | 1.00 |
C137—C138 | 1.509 (13) | C237—C238 | 1.554 (12) |
C137—H13A | 0.99 | C237—H23A | 0.99 |
C137—H13B | 0.99 | C237—H23B | 0.99 |
C138—H13C | 0.98 | C238—H23C | 0.98 |
C138—H13D | 0.98 | C238—H23D | 0.98 |
C138—H13E | 0.98 | C238—H23E | 0.98 |
C14—O14 | 1.246 (9) | C24—O24 | 1.233 (9) |
C14—C15 | 1.446 (12) | C24—C25 | 1.457 (11) |
C15—C16 | 1.562 (11) | C25—C26 | 1.559 (10) |
C15—H15A | 0.99 | C25—H25A | 0.99 |
C15—H15B | 0.99 | C25—H25B | 0.99 |
C16—C121 | 1.506 (11) | C26—C221 | 1.517 (11) |
C16—H16 | 1.00 | C26—H26 | 1.00 |
C121—C126 | 1.376 (11) | C221—C222 | 1.380 (12) |
C121—C122 | 1.417 (11) | C221—C226 | 1.415 (10) |
C122—C123 | 1.372 (12) | C226—C225 | 1.382 (11) |
C122—H122 | 0.95 | C226—H226 | 0.95 |
C123—C124 | 1.356 (12) | C225—C224 | 1.370 (12) |
C123—H123 | 0.95 | C225—H225 | 0.95 |
C124—C125 | 1.389 (11) | C224—C223 | 1.411 (13) |
C124—H124 | 0.95 | C224—H224 | 0.95 |
C125—C126 | 1.400 (11) | C223—C222 | 1.390 (13) |
C125—H125 | 0.95 | C223—H223 | 0.95 |
C126—H126 | 0.95 | C222—H222 | 0.95 |
C17—O17 | 1.246 (9) | C27—O27 | 1.221 (9) |
C17—C18 | 1.517 (11) | C27—C28 | 1.514 (11) |
C18—C131 | 1.502 (11) | C28—C231 | 1.514 (10) |
C18—H18A | 0.99 | C28—H28A | 0.99 |
C18—H18B | 0.99 | C28—H28B | 0.99 |
C131—C132 | 1.382 (11) | C231—C236 | 1.361 (11) |
C131—C136 | 1.401 (10) | C231—C232 | 1.417 (10) |
C132—C133 | 1.354 (11) | C232—C233 | 1.373 (11) |
C132—H132 | 0.95 | C232—H232 | 0.95 |
C133—C134 | 1.397 (11) | C233—C234 | 1.390 (11) |
C133—H133 | 0.95 | C233—H233 | 0.95 |
C134—C135 | 1.349 (11) | C234—C235 | 1.402 (11) |
C134—H134 | 0.95 | C234—H234 | 0.95 |
C135—C136 | 1.405 (11) | C235—C236 | 1.371 (11) |
C135—H135 | 0.95 | C235—H235 | 0.95 |
C136—H136 | 0.95 | C236—H236 | 0.95 |
C17—N11—C12 | 120.0 (7) | C27—N21—C26 | 117.1 (7) |
C17—N11—C16 | 119.3 (6) | C27—N21—C22 | 121.4 (6) |
C12—N11—C16 | 119.6 (6) | C26—N21—C22 | 121.0 (6) |
N11—C12—C111 | 113.8 (7) | N21—C22—C211 | 112.7 (6) |
N11—C12—C13 | 109.4 (7) | N21—C22—C23 | 108.4 (6) |
C111—C12—C13 | 114.6 (7) | C211—C22—C23 | 113.1 (7) |
N11—C12—H12 | 106.1 | N21—C22—H22 | 107.5 |
C111—C12—H12 | 106.1 | C211—C22—H22 | 107.5 |
C13—C12—H12 | 106.1 | C23—C22—H22 | 107.5 |
C112—C111—C116 | 118.6 (9) | C212—C211—C216 | 119.7 (7) |
C112—C111—C12 | 123.5 (7) | C212—C211—C22 | 121.7 (8) |
C116—C111—C12 | 117.7 (9) | C216—C211—C22 | 118.6 (7) |
C115—C116—C111 | 118.9 (10) | C213—C212—C211 | 119.3 (9) |
C115—C116—H116 | 120.5 | C213—C212—H212 | 120.4 |
C111—C116—H116 | 120.5 | C211—C212—H212 | 120.4 |
C114—C115—C116 | 121.9 (9) | C212—C213—C214 | 122.5 (9) |
C114—C115—H115 | 119.0 | C212—C213—H213 | 118.7 |
C116—C115—H115 | 119.0 | C214—C213—H213 | 118.7 |
C115—C114—C113 | 119.6 (11) | C213—C214—C215 | 119.6 (8) |
C115—C114—H114 | 120.2 | C213—C214—H214 | 120.2 |
C113—C114—H114 | 120.2 | C215—C214—H214 | 120.2 |
C114—C113—C112 | 120.1 (11) | C216—C215—C214 | 118.4 (8) |
C114—C113—H113 | 119.9 | C216—C215—H215 | 120.8 |
C112—C113—H113 | 119.9 | C214—C215—H215 | 120.8 |
C111—C112—C113 | 120.7 (9) | C215—C216—C211 | 120.5 (7) |
C111—C112—H112 | 119.7 | C215—C216—H216 | 119.8 |
C113—C112—H112 | 119.7 | C211—C216—H216 | 119.8 |
C137—C13—C14 | 109.7 (8) | C237—C23—C22 | 110.8 (7) |
C137—C13—C12 | 111.5 (8) | C237—C23—C24 | 112.1 (6) |
C14—C13—C12 | 111.4 (8) | C22—C23—C24 | 109.4 (7) |
C137—C13—H13 | 108.0 | C237—C23—H23 | 108.1 |
C14—C13—H13 | 108.0 | C22—C23—H23 | 108.1 |
C12—C13—H13 | 108.0 | C24—C23—H23 | 108.1 |
C13—C137—C138 | 116.0 (9) | C23—C237—C238 | 111.0 (7) |
C13—C137—H13A | 108.3 | C23—C237—H23A | 109.4 |
C138—C137—H13A | 108.3 | C238—C237—H23A | 109.4 |
C13—C137—H13B | 108.3 | C23—C237—H23B | 109.4 |
C138—C137—H13B | 108.3 | C238—C237—H23B | 109.4 |
H13A—C137—H13B | 107.4 | H23A—C237—H23B | 108.0 |
C137—C138—H13C | 109.5 | C237—C238—H23C | 109.5 |
C137—C138—H13D | 109.5 | C237—C238—H23D | 109.5 |
H13C—C138—H13D | 109.5 | H23C—C238—H23D | 109.5 |
C137—C138—H13E | 109.5 | C237—C238—H23E | 109.5 |
H13C—C138—H13E | 109.5 | H23C—C238—H23E | 109.5 |
H13D—C138—H13E | 109.5 | H23D—C238—H23E | 109.5 |
O14—C14—C15 | 121.2 (10) | O24—C24—C25 | 120.1 (8) |
O14—C14—C13 | 122.8 (9) | O24—C24—C23 | 121.8 (8) |
C15—C14—C13 | 116.0 (7) | C25—C24—C23 | 117.8 (7) |
C14—C15—C16 | 115.8 (8) | C24—C25—C26 | 111.6 (7) |
C14—C15—H15A | 108.3 | C24—C25—H25A | 109.3 |
C16—C15—H15A | 108.3 | C26—C25—H25A | 109.3 |
C14—C15—H15B | 108.3 | C24—C25—H25B | 109.3 |
C16—C15—H15B | 108.3 | C26—C25—H25B | 109.3 |
H15A—C15—H15B | 107.4 | H25A—C25—H25B | 108.0 |
N11—C16—C121 | 114.3 (6) | N21—C26—C221 | 112.0 (6) |
N11—C16—C15 | 108.5 (6) | N21—C26—C25 | 109.4 (6) |
C121—C16—C15 | 107.9 (7) | C221—C26—C25 | 118.1 (7) |
N11—C16—H16 | 108.6 | N21—C26—H26 | 105.4 |
C121—C16—H16 | 108.6 | C221—C26—H26 | 105.4 |
C15—C16—H16 | 108.6 | C25—C26—H26 | 105.4 |
C126—C121—C122 | 118.6 (8) | C222—C221—C226 | 117.4 (8) |
C126—C121—C16 | 120.3 (7) | C222—C221—C26 | 125.8 (7) |
C122—C121—C16 | 121.0 (8) | C226—C221—C26 | 116.8 (8) |
C123—C122—C121 | 119.4 (9) | C225—C226—C221 | 120.5 (8) |
C123—C122—H122 | 120.3 | C225—C226—H226 | 119.8 |
C121—C122—H122 | 120.3 | C221—C226—H226 | 119.8 |
C124—C123—C122 | 122.8 (8) | C224—C225—C226 | 121.7 (8) |
C124—C123—H123 | 118.6 | C224—C225—H225 | 119.2 |
C122—C123—H123 | 118.6 | C226—C225—H225 | 119.2 |
C123—C124—C125 | 118.1 (8) | C225—C224—C223 | 118.7 (10) |
C123—C124—H124 | 120.9 | C225—C224—H224 | 120.7 |
C125—C124—H124 | 120.9 | C223—C224—H224 | 120.7 |
C124—C125—C126 | 121.0 (9) | C222—C223—C224 | 119.4 (9) |
C124—C125—H125 | 119.5 | C222—C223—H223 | 120.3 |
C126—C125—H125 | 119.5 | C224—C223—H223 | 120.3 |
C121—C126—C125 | 120.0 (8) | C221—C222—C223 | 122.3 (8) |
C121—C126—H126 | 120.0 | C221—C222—H222 | 118.9 |
C125—C126—H126 | 120.0 | C223—C222—H222 | 118.9 |
O17—C17—N11 | 119.9 (7) | O27—C27—N21 | 120.7 (7) |
O17—C17—C18 | 120.7 (7) | O27—C27—C28 | 120.9 (7) |
N11—C17—C18 | 119.4 (7) | N21—C27—C28 | 118.2 (8) |
C131—C18—C17 | 115.0 (7) | C27—C28—C231 | 112.1 (6) |
C131—C18—H18A | 108.5 | C27—C28—H28A | 109.2 |
C17—C18—H18A | 108.5 | C231—C28—H28A | 109.2 |
C131—C18—H18B | 108.5 | C27—C28—H28B | 109.2 |
C17—C18—H18B | 108.5 | C231—C28—H28B | 109.2 |
H18A—C18—H18B | 107.5 | H28A—C28—H28B | 107.9 |
C132—C131—C136 | 117.5 (8) | C236—C231—C232 | 118.0 (8) |
C132—C131—C18 | 121.5 (7) | C236—C231—C28 | 121.2 (7) |
C136—C131—C18 | 121.0 (8) | C232—C231—C28 | 120.8 (8) |
C133—C132—C131 | 122.9 (7) | C233—C232—C231 | 119.6 (8) |
C133—C132—H132 | 118.6 | C233—C232—H232 | 120.2 |
C131—C132—H132 | 118.6 | C231—C232—H232 | 120.2 |
C132—C133—C134 | 120.1 (9) | C232—C233—C234 | 121.7 (7) |
C132—C133—H133 | 119.9 | C232—C233—H233 | 119.1 |
C134—C133—H133 | 119.9 | C234—C233—H233 | 119.1 |
C135—C134—C133 | 118.2 (8) | C233—C234—C235 | 118.0 (8) |
C135—C134—H134 | 120.9 | C233—C234—H234 | 121.0 |
C133—C134—H134 | 120.9 | C235—C234—H234 | 121.0 |
C134—C135—C136 | 122.6 (7) | C236—C235—C234 | 119.7 (8) |
C134—C135—H135 | 118.7 | C236—C235—H235 | 120.1 |
C136—C135—H135 | 118.7 | C234—C235—H235 | 120.1 |
C131—C136—C135 | 118.7 (8) | C231—C236—C235 | 122.9 (7) |
C131—C136—H136 | 120.6 | C231—C236—H236 | 118.6 |
C135—C136—H136 | 120.6 | C235—C236—H236 | 118.6 |
C17—N11—C12—C111 | 107.5 (9) | C27—N21—C22—C211 | 68.9 (9) |
C16—N11—C12—C111 | −84.3 (8) | C26—N21—C22—C211 | −119.5 (7) |
C17—N11—C12—C13 | −122.9 (8) | C27—N21—C22—C23 | −165.2 (6) |
C16—N11—C12—C13 | 45.3 (11) | C26—N21—C22—C23 | 6.4 (10) |
C12—C13—C137—C138 | 67.5 (11) | C22—C23—C237—C238 | 154.9 (7) |
N11—C12—C111—C112 | 130.2 (10) | N21—C22—C211—C212 | 57.0 (10) |
N11—C16—C121—C122 | −41.2 (10) | N21—C26—C221—C222 | −118.6 (9) |
C12—N11—C17—C18 | 173.3 (7) | C22—N21—C27—C28 | −4.2 (9) |
N11—C17—C18—C131 | −162.0 (7) | N21—C27—C28—C231 | 158.6 (6) |
C17—C18—C131—C132 | 98.1 (9) | C27—C28—C231—C232 | 79.2 (8) |
C13—C12—C111—C112 | 3.3 (14) | C23—C22—C211—C212 | −66.4 (9) |
N11—C12—C111—C116 | −54.3 (11) | N21—C22—C211—C216 | −124.2 (7) |
C13—C12—C111—C116 | 178.7 (9) | C23—C22—C211—C216 | 112.4 (8) |
C112—C111—C116—C115 | −2.9 (16) | C216—C211—C212—C213 | 0.1 (11) |
C12—C111—C116—C115 | −178.6 (9) | C22—C211—C212—C213 | 178.9 (7) |
C111—C116—C115—C114 | 2.6 (17) | C211—C212—C213—C214 | 0.0 (13) |
C116—C115—C114—C113 | −2 (2) | C212—C213—C214—C215 | 0.1 (13) |
C115—C114—C113—C112 | 1 (2) | C213—C214—C215—C216 | −0.4 (11) |
C116—C111—C112—C113 | 2.5 (17) | C214—C215—C216—C211 | 0.5 (10) |
C12—C111—C112—C113 | 177.9 (11) | C212—C211—C216—C215 | −0.4 (11) |
C114—C113—C112—C111 | −1.6 (19) | C22—C211—C216—C215 | −179.2 (6) |
N11—C12—C13—C137 | 65.9 (11) | N21—C22—C23—C237 | 169.5 (7) |
C111—C12—C13—C137 | −165.0 (8) | C211—C22—C23—C237 | −64.8 (9) |
N11—C12—C13—C14 | −57.0 (10) | N21—C22—C23—C24 | 45.4 (8) |
C111—C12—C13—C14 | 72.1 (10) | C211—C22—C23—C24 | 171.1 (7) |
C14—C13—C137—C138 | −168.7 (8) | C24—C23—C237—C238 | −82.5 (9) |
C137—C13—C14—O14 | 75.7 (12) | C237—C23—C24—O24 | −3.3 (12) |
C12—C13—C14—O14 | −160.4 (9) | C22—C23—C24—O24 | 120.1 (8) |
C137—C13—C14—C15 | −107.3 (9) | C237—C23—C24—C25 | −178.5 (7) |
C12—C13—C14—C15 | 16.6 (12) | C22—C23—C24—C25 | −55.2 (10) |
O14—C14—C15—C16 | −146.4 (9) | O24—C24—C25—C26 | −167.3 (7) |
C13—C14—C15—C16 | 36.6 (11) | C23—C24—C25—C26 | 8.0 (11) |
C17—N11—C16—C121 | −66.1 (9) | C27—N21—C26—C221 | −108.4 (8) |
C12—N11—C16—C121 | 125.7 (7) | C22—N21—C26—C221 | 79.6 (8) |
C17—N11—C16—C15 | 173.4 (7) | C27—N21—C26—C25 | 118.6 (7) |
C12—N11—C16—C15 | 5.2 (10) | C22—N21—C26—C25 | −53.3 (10) |
C14—C15—C16—N11 | −48.2 (9) | C24—C25—C26—N21 | 43.3 (10) |
C14—C15—C16—C121 | −172.7 (7) | C24—C25—C26—C221 | −86.3 (9) |
N11—C16—C121—C126 | 139.8 (7) | C25—C26—C221—C222 | 9.9 (13) |
C15—C16—C121—C126 | −99.3 (8) | N21—C26—C221—C226 | 60.5 (10) |
C15—C16—C121—C122 | 79.7 (8) | C25—C26—C221—C226 | −171.0 (8) |
C126—C121—C122—C123 | 0.8 (11) | C222—C221—C226—C225 | 2.3 (13) |
C16—C121—C122—C123 | −178.2 (7) | C26—C221—C226—C225 | −176.9 (8) |
C121—C122—C123—C124 | 1.9 (12) | C221—C226—C225—C224 | 0.5 (14) |
C122—C123—C124—C125 | −2.9 (12) | C226—C225—C224—C223 | −3.0 (15) |
C123—C124—C125—C126 | 1.1 (11) | C225—C224—C223—C222 | 2.8 (16) |
C122—C121—C126—C125 | −2.4 (11) | C226—C221—C222—C223 | −2.5 (15) |
C16—C121—C126—C125 | 176.6 (7) | C26—C221—C222—C223 | 176.6 (9) |
C124—C125—C126—C121 | 1.5 (11) | C224—C223—C222—C221 | 0.0 (17) |
C12—N11—C17—O17 | −6.0 (11) | C26—N21—C27—O27 | 6.7 (10) |
C16—N11—C17—O17 | −174.2 (7) | C22—N21—C27—O27 | 178.7 (7) |
C16—N11—C17—C18 | 5.1 (10) | C26—N21—C27—C28 | −176.1 (6) |
O17—C17—C18—C131 | 17.3 (11) | O27—C27—C28—C231 | −24.2 (9) |
C17—C18—C131—C136 | −84.2 (9) | C27—C28—C231—C236 | −102.5 (8) |
C136—C131—C132—C133 | 0.7 (13) | C236—C231—C232—C233 | 1.6 (11) |
C18—C131—C132—C133 | 178.4 (8) | C28—C231—C232—C233 | 179.9 (7) |
C131—C132—C133—C134 | −2.0 (15) | C231—C232—C233—C234 | 0.4 (12) |
C132—C133—C134—C135 | 2.0 (14) | C232—C233—C234—C235 | −1.7 (13) |
C133—C134—C135—C136 | −0.8 (13) | C233—C234—C235—C236 | 1.1 (14) |
C132—C131—C136—C135 | 0.6 (12) | C232—C231—C236—C235 | −2.3 (13) |
C18—C131—C136—C135 | −177.2 (7) | C28—C231—C236—C235 | 179.4 (8) |
C134—C135—C136—C131 | −0.5 (12) | C234—C235—C236—C231 | 1.0 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···O24i | 1.00 | 2.35 | 3.232 (10) | 147 |
C22—H22···O27ii | 1.00 | 2.19 | 3.190 (10) | 175 |
C28—H28A···O27ii | 0.99 | 2.52 | 3.486 (9) | 165 |
C222—H222···O14i | 0.95 | 2.54 | 3.478 (10) | 169 |
C123—H123···Cgiii | 0.95 | 2.89 | 3.811 (10) | 165 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+3/2, z−1/2; (iii) x, y, z+1. |
Acknowledgements
X-ray data were collected through the EPSRC X-ray Crystallographic Service at Daresbury SRS station 9.8, UK. The authors thank the staff for all their help and advice.
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