



Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015014887/xu5865sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2056989015014887/xu5865Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015014887/xu5865Isup3.cml |
CCDC reference: 1023392
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.050
- wR factor = 0.147
- Data-to-parameter ratio = 19.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ... -10.901 Report PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 5 Report
Alert level G PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT230_ALERT_2_G Hirshfeld Test Diff for C2 -- C24 .. 5.6 su PLAT793_ALERT_4_G The Model has Chirality at C3 (Centro SPGR) R Verify PLAT793_ALERT_4_G The Model has Chirality at C4 (Centro SPGR) R Verify PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 142 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 5 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound 5-benzoyl-2,4-diphenyl-4,5-dihydrofuran-3-carbonitrile (I) is a dihydrofuran carbonitrile derivative. Dihydrofurans belong to an important class of heterocycles and are known for distinct insect antifeedant activities (Gebbinck et al., 1999). Dihydrofurans have also been found to possess antifungal (Pour et al., 2003) and anti-inflammatory properties (Kumar et al., 2003). The dihydrofuran derivatives with their reactive functional groups like methoxy, carbonyl etc. may prove to be promising candidates for the synthesis of novel heterocyclic compounds. The in vitro antibacterial and antifungal activities of some furan derivatives, specifically, 4,5-dihydrofuran-3-carbonitriles were investigated against some bacteria and fungi and were found to show activity against bacteria better than some known antibiotics (Loğoğlu et al., 2010).
A mixture of benzoylacetonitrile (1.0 mmol), benzaldehyde (1.0 mmol) and imidazolium salt (1-methyl-3-(2-oxo-2-phenylethyl)-1H-imidazol-3-ium bromide) (1.0 mmol) were dissolved in EtOH (10 mL) then Et3N(triethylamine) (1.0 mmol) was added slowly and refluxed on a water bath. The consumption of starting material was monitored by TLC. After 3hours the reaction mixture was cooled and the precipitated solid product was filtered and washed. Crystals of (1) suitable for diffraction were obtained.
All H atoms were included into the model at geometrically calculated positions (C—H target distance = 0.98 Å for methine H atoms and 0.93 Å for all other aromatic H atoms) and refined using a riding model. The Uiso values of all H atoms were constrained to 1.2 times Ueq of the respective atom to which the H atom binds.
The carbonyl O of the benzoyl group is cis with the furanyl O atom with the value of the associated torsion angle being 4.62°. The puckering of the hydrofuran ring is close to twisted (4T5) with parameters Q = 0.1856 (16) Å and φ = 313.5 (5)°. The angle between the mean plane about the furan ring atoms and the 2-phenyl ring is 22.5 (1)° while those with respect to the 4-phenyl and the 5-benzoyl group atoms are 88.6 (1) and 78.4 (1)°, respectively.
A search in the CSD [version 5.53, update 3, May 2013] for organic nonpolymeric single crystal structures for which 3D coordinates determined with no disorder, no ions and no other errors with R-factors less than 0.05 revealed 6287 structures of which 2498 had the furan O involved in C—H···O interactions with the H···A ranging from 2.127 to 2.720 Å. Also, four structures bearing close relationships to the title compound with refcodes LEFJUD (Suresh et al., 2012a), YAXGOV (Suresh et al., 2012b), ZARBEB (Suresh et al., 2012c) and EDUZAG (Rajni Rajni et al., 2012) were found. These structures differ by an indole ring replaced by a phenyl in the title compound and interestingly none display any change in the crystal system or lattice type. However, there are drastic differences in the intermolecular interaction patterns. The molecules are interconnected via a C—H···N and a C—H···O hydrogen-bond leading to a layers parallel to the (200) plane and characterized by R44(28) and R44(36) graph-set motifs. The furan O atom does not participate in the intermolecular hydrogen bonding. The crystal lattice encompasses a solvent accessible void of 24.7 (8) Å3.
The title compound 5-benzoyl-2,4-diphenyl-4,5-dihydrofuran-3-carbonitrile (I) is a dihydrofuran carbonitrile derivative. Dihydrofurans belong to an important class of heterocycles and are known for distinct insect antifeedant activities (Gebbinck et al., 1999). Dihydrofurans have also been found to possess antifungal (Pour et al., 2003) and anti-inflammatory properties (Kumar et al., 2003). The dihydrofuran derivatives with their reactive functional groups like methoxy, carbonyl etc. may prove to be promising candidates for the synthesis of novel heterocyclic compounds. The in vitro antibacterial and antifungal activities of some furan derivatives, specifically, 4,5-dihydrofuran-3-carbonitriles were investigated against some bacteria and fungi and were found to show activity against bacteria better than some known antibiotics (Loğoğlu et al., 2010).
The carbonyl O of the benzoyl group is cis with the furanyl O atom with the value of the associated torsion angle being 4.62°. The puckering of the hydrofuran ring is close to twisted (4T5) with parameters Q = 0.1856 (16) Å and φ = 313.5 (5)°. The angle between the mean plane about the furan ring atoms and the 2-phenyl ring is 22.5 (1)° while those with respect to the 4-phenyl and the 5-benzoyl group atoms are 88.6 (1) and 78.4 (1)°, respectively.
A search in the CSD [version 5.53, update 3, May 2013] for organic nonpolymeric single crystal structures for which 3D coordinates determined with no disorder, no ions and no other errors with R-factors less than 0.05 revealed 6287 structures of which 2498 had the furan O involved in C—H···O interactions with the H···A ranging from 2.127 to 2.720 Å. Also, four structures bearing close relationships to the title compound with refcodes LEFJUD (Suresh et al., 2012a), YAXGOV (Suresh et al., 2012b), ZARBEB (Suresh et al., 2012c) and EDUZAG (Rajni Rajni et al., 2012) were found. These structures differ by an indole ring replaced by a phenyl in the title compound and interestingly none display any change in the crystal system or lattice type. However, there are drastic differences in the intermolecular interaction patterns. The molecules are interconnected via a C—H···N and a C—H···O hydrogen-bond leading to a layers parallel to the (200) plane and characterized by R44(28) and R44(36) graph-set motifs. The furan O atom does not participate in the intermolecular hydrogen bonding. The crystal lattice encompasses a solvent accessible void of 24.7 (8) Å3.
For biological activity of dihydrofurans, see: Simmonds et al. (1990); Gebbinck et al. (1999); Ley et al. (1987); Kumar et al. (2003); Pour et al. (2003); Loğoğlu et al. (2010). For Cambridge Structural Database, see: Groom & Allen (2014). For graph-set motifs, see: Bernstein et al. (1995). For puckering of rings, see: Cremer & Pople (1975). For related structures, see: Rajni Swamy et al. (2012); Suresh et al. (2012a,b,c).
A mixture of benzoylacetonitrile (1.0 mmol), benzaldehyde (1.0 mmol) and imidazolium salt (1-methyl-3-(2-oxo-2-phenylethyl)-1H-imidazol-3-ium bromide) (1.0 mmol) were dissolved in EtOH (10 mL) then Et3N(triethylamine) (1.0 mmol) was added slowly and refluxed on a water bath. The consumption of starting material was monitored by TLC. After 3hours the reaction mixture was cooled and the precipitated solid product was filtered and washed. Crystals of (1) suitable for diffraction were obtained.
All H atoms were included into the model at geometrically calculated positions (C—H target distance = 0.98 Å for methine H atoms and 0.93 Å for all other aromatic H atoms) and refined using a riding model. The Uiso values of all H atoms were constrained to 1.2 times Ueq of the respective atom to which the H atom binds.
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).
C24H17NO2 | F(000) = 736 |
Mr = 351.38 | Dx = 1.252 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.0704 (7) Å | Cell parameters from 2305 reflections |
b = 15.7994 (12) Å | θ = 2.2–28.6° |
c = 11.8632 (9) Å | µ = 0.08 mm−1 |
β = 98.886 (3)° | T = 298 K |
V = 1864.9 (2) Å3 | Block, colourless |
Z = 4 | 0.35 × 0.24 × 0.08 mm |
Bruker SMART APEXII CCD diffractometer | 2305 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.063 |
ω and φ scans | θmax = 28.6°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −13→12 |
Tmin = 0.973, Tmax = 0.994 | k = −21→21 |
34345 measured reflections | l = −15→15 |
4648 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.050 | w = 1/[σ2(Fo2) + (0.0717P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.147 | (Δ/σ)max < 0.001 |
S = 0.99 | Δρmax = 0.15 e Å−3 |
4648 reflections | Δρmin = −0.16 e Å−3 |
245 parameters | Extinction correction: SHELXL2014 (Sheldrick 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0097 (17) |
C24H17NO2 | V = 1864.9 (2) Å3 |
Mr = 351.38 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.0704 (7) Å | µ = 0.08 mm−1 |
b = 15.7994 (12) Å | T = 298 K |
c = 11.8632 (9) Å | 0.35 × 0.24 × 0.08 mm |
β = 98.886 (3)° |
Bruker SMART APEXII CCD diffractometer | 4648 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 2305 reflections with I > 2σ(I) |
Tmin = 0.973, Tmax = 0.994 | Rint = 0.063 |
34345 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.147 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.15 e Å−3 |
4648 reflections | Δρmin = −0.16 e Å−3 |
245 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.65312 (11) | 0.12681 (7) | −0.07149 (10) | 0.0503 (3) | |
O2 | 0.63839 (11) | 0.02849 (7) | 0.10317 (10) | 0.0584 (4) | |
N1 | 0.84295 (18) | 0.37076 (11) | 0.11942 (17) | 0.0817 (6) | |
C1 | 0.74999 (16) | 0.18513 (10) | −0.03978 (14) | 0.0430 (4) | |
C2 | 0.70930 (15) | 0.24665 (10) | 0.02407 (13) | 0.0423 (4) | |
C3 | 0.56268 (15) | 0.23450 (9) | 0.03502 (13) | 0.0416 (4) | |
H3 | 0.5515 | 0.2365 | 0.1156 | 0.050* | |
C4 | 0.54406 (15) | 0.14312 (9) | −0.00964 (14) | 0.0432 (4) | |
H4 | 0.4586 | 0.1385 | −0.0614 | 0.052* | |
C5 | 0.54745 (15) | 0.07881 (10) | 0.08555 (14) | 0.0425 (4) | |
C6 | 0.43803 (15) | 0.08113 (10) | 0.15584 (14) | 0.0436 (4) | |
C7 | 0.32474 (17) | 0.13099 (11) | 0.12818 (16) | 0.0529 (5) | |
H7 | 0.3158 | 0.1651 | 0.0635 | 0.063* | |
C8 | 0.22520 (18) | 0.13050 (12) | 0.19565 (18) | 0.0639 (5) | |
H8 | 0.1487 | 0.1635 | 0.1759 | 0.077* | |
C9 | 0.23861 (19) | 0.08169 (13) | 0.29133 (18) | 0.0673 (6) | |
H9 | 0.1720 | 0.0821 | 0.3376 | 0.081* | |
C10 | 0.3498 (2) | 0.03227 (13) | 0.31933 (18) | 0.0690 (6) | |
H10 | 0.3584 | −0.0011 | 0.3846 | 0.083* | |
C11 | 0.44916 (18) | 0.03135 (11) | 0.25209 (16) | 0.0557 (5) | |
H11 | 0.5242 | −0.0030 | 0.2716 | 0.067* | |
C12 | 0.87832 (16) | 0.16935 (11) | −0.07951 (14) | 0.0466 (4) | |
C13 | 0.9140 (2) | 0.08775 (12) | −0.10240 (16) | 0.0633 (5) | |
H13 | 0.8558 | 0.0433 | −0.0941 | 0.076* | |
C14 | 1.0350 (2) | 0.07193 (15) | −0.13726 (19) | 0.0773 (6) | |
H14 | 1.0591 | 0.0165 | −0.1513 | 0.093* | |
C15 | 1.12049 (19) | 0.13654 (15) | −0.15166 (17) | 0.0702 (6) | |
H15 | 1.2021 | 0.1253 | −0.1760 | 0.084* | |
C16 | 1.08594 (19) | 0.21745 (15) | −0.13026 (17) | 0.0691 (6) | |
H16 | 1.1441 | 0.2616 | −0.1402 | 0.083* | |
C17 | 0.96536 (17) | 0.23435 (12) | −0.09402 (16) | 0.0594 (5) | |
H17 | 0.9425 | 0.2898 | −0.0793 | 0.071* | |
C18 | 0.47459 (14) | 0.29991 (9) | −0.03105 (13) | 0.0414 (4) | |
C19 | 0.44746 (16) | 0.29744 (10) | −0.14855 (15) | 0.0488 (4) | |
H19 | 0.4797 | 0.2527 | −0.1876 | 0.059* | |
C20 | 0.37323 (16) | 0.36044 (11) | −0.20860 (16) | 0.0565 (5) | |
H20 | 0.3551 | 0.3577 | −0.2878 | 0.068* | |
C21 | 0.32609 (18) | 0.42665 (12) | −0.15322 (19) | 0.0635 (5) | |
H21 | 0.2763 | 0.4692 | −0.1942 | 0.076* | |
C22 | 0.3523 (2) | 0.43001 (12) | −0.03784 (19) | 0.0745 (6) | |
H22 | 0.3207 | 0.4754 | 0.0003 | 0.089* | |
C23 | 0.42525 (19) | 0.36704 (11) | 0.02362 (17) | 0.0646 (5) | |
H23 | 0.4413 | 0.3699 | 0.1029 | 0.078* | |
C24 | 0.78533 (16) | 0.31484 (11) | 0.07499 (16) | 0.0513 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0546 (7) | 0.0452 (7) | 0.0539 (7) | −0.0099 (6) | 0.0172 (6) | −0.0127 (5) |
O2 | 0.0528 (7) | 0.0550 (8) | 0.0674 (9) | 0.0109 (6) | 0.0097 (6) | 0.0034 (6) |
N1 | 0.0806 (12) | 0.0659 (11) | 0.0966 (14) | −0.0206 (10) | 0.0077 (10) | −0.0269 (10) |
C1 | 0.0468 (9) | 0.0375 (9) | 0.0443 (10) | −0.0054 (8) | 0.0060 (8) | 0.0005 (8) |
C2 | 0.0430 (9) | 0.0367 (9) | 0.0463 (10) | −0.0020 (7) | 0.0035 (7) | −0.0019 (8) |
C3 | 0.0487 (9) | 0.0389 (9) | 0.0379 (9) | −0.0027 (7) | 0.0094 (7) | −0.0017 (7) |
C4 | 0.0427 (9) | 0.0431 (9) | 0.0445 (10) | −0.0044 (7) | 0.0089 (8) | −0.0045 (8) |
C5 | 0.0413 (9) | 0.0364 (9) | 0.0482 (10) | −0.0045 (8) | 0.0021 (8) | −0.0038 (8) |
C6 | 0.0445 (9) | 0.0393 (9) | 0.0466 (10) | −0.0038 (8) | 0.0059 (8) | 0.0007 (8) |
C7 | 0.0467 (10) | 0.0562 (11) | 0.0559 (11) | 0.0022 (9) | 0.0081 (9) | 0.0100 (9) |
C8 | 0.0515 (11) | 0.0690 (13) | 0.0716 (14) | 0.0094 (10) | 0.0111 (10) | 0.0070 (11) |
C9 | 0.0635 (13) | 0.0747 (13) | 0.0692 (14) | −0.0002 (11) | 0.0281 (11) | 0.0056 (11) |
C10 | 0.0703 (13) | 0.0761 (14) | 0.0635 (13) | 0.0015 (11) | 0.0192 (11) | 0.0218 (11) |
C11 | 0.0564 (11) | 0.0520 (11) | 0.0589 (12) | 0.0038 (9) | 0.0092 (9) | 0.0108 (9) |
C12 | 0.0482 (10) | 0.0476 (10) | 0.0445 (10) | 0.0023 (8) | 0.0084 (8) | 0.0031 (8) |
C13 | 0.0719 (13) | 0.0543 (12) | 0.0687 (14) | 0.0009 (10) | 0.0264 (10) | −0.0070 (10) |
C14 | 0.0773 (14) | 0.0734 (15) | 0.0873 (17) | 0.0169 (13) | 0.0319 (12) | −0.0070 (12) |
C15 | 0.0540 (12) | 0.1010 (18) | 0.0580 (13) | 0.0167 (13) | 0.0167 (10) | 0.0003 (12) |
C16 | 0.0489 (11) | 0.0859 (16) | 0.0743 (15) | −0.0054 (11) | 0.0151 (10) | 0.0106 (12) |
C17 | 0.0522 (11) | 0.0547 (11) | 0.0727 (14) | 0.0007 (9) | 0.0144 (10) | 0.0062 (10) |
C18 | 0.0399 (9) | 0.0406 (9) | 0.0450 (10) | −0.0033 (7) | 0.0106 (7) | −0.0037 (8) |
C19 | 0.0503 (10) | 0.0482 (10) | 0.0487 (11) | 0.0018 (8) | 0.0100 (8) | −0.0028 (8) |
C20 | 0.0543 (11) | 0.0626 (12) | 0.0510 (11) | −0.0020 (10) | 0.0032 (9) | 0.0056 (10) |
C21 | 0.0557 (11) | 0.0582 (12) | 0.0752 (15) | 0.0094 (10) | 0.0050 (10) | 0.0093 (11) |
C22 | 0.0857 (15) | 0.0630 (13) | 0.0764 (16) | 0.0308 (12) | 0.0173 (12) | −0.0053 (11) |
C23 | 0.0802 (13) | 0.0641 (12) | 0.0503 (12) | 0.0166 (11) | 0.0125 (10) | −0.0083 (10) |
C24 | 0.0503 (10) | 0.0459 (10) | 0.0564 (11) | −0.0014 (9) | 0.0047 (9) | −0.0047 (9) |
O1—C1 | 1.3523 (18) | C11—H11 | 0.9300 |
O1—C4 | 1.4352 (18) | C12—C13 | 1.377 (2) |
O2—C5 | 1.2064 (17) | C12—C17 | 1.378 (2) |
N1—C24 | 1.140 (2) | C13—C14 | 1.368 (3) |
C1—C2 | 1.335 (2) | C13—H13 | 0.9300 |
C1—C12 | 1.464 (2) | C14—C15 | 1.363 (3) |
C2—C24 | 1.403 (2) | C14—H14 | 0.9300 |
C2—C3 | 1.514 (2) | C15—C16 | 1.359 (3) |
C3—C18 | 1.502 (2) | C15—H15 | 0.9300 |
C3—C4 | 1.539 (2) | C16—C17 | 1.375 (2) |
C3—H3 | 0.9800 | C16—H16 | 0.9300 |
C4—C5 | 1.516 (2) | C17—H17 | 0.9300 |
C4—H4 | 0.9800 | C18—C23 | 1.375 (2) |
C5—C6 | 1.481 (2) | C18—C19 | 1.379 (2) |
C6—C11 | 1.377 (2) | C19—C20 | 1.376 (2) |
C6—C7 | 1.384 (2) | C19—H19 | 0.9300 |
C7—C8 | 1.376 (2) | C20—C21 | 1.359 (3) |
C7—H7 | 0.9300 | C20—H20 | 0.9300 |
C8—C9 | 1.362 (3) | C21—C22 | 1.354 (3) |
C8—H8 | 0.9300 | C21—H21 | 0.9300 |
C9—C10 | 1.363 (3) | C22—C23 | 1.377 (3) |
C9—H9 | 0.9300 | C22—H22 | 0.9300 |
C10—C11 | 1.373 (2) | C23—H23 | 0.9300 |
C10—H10 | 0.9300 | ||
C1—O1—C4 | 108.15 (11) | C6—C11—H11 | 119.9 |
C2—C1—O1 | 112.48 (14) | C13—C12—C17 | 118.86 (16) |
C2—C1—C12 | 132.09 (15) | C13—C12—C1 | 119.57 (16) |
O1—C1—C12 | 115.42 (13) | C17—C12—C1 | 121.57 (16) |
C1—C2—C24 | 127.47 (15) | C14—C13—C12 | 120.16 (19) |
C1—C2—C3 | 110.19 (13) | C14—C13—H13 | 119.9 |
C24—C2—C3 | 122.34 (14) | C12—C13—H13 | 119.9 |
C18—C3—C2 | 111.91 (12) | C15—C14—C13 | 120.7 (2) |
C18—C3—C4 | 115.79 (13) | C15—C14—H14 | 119.7 |
C2—C3—C4 | 99.09 (12) | C13—C14—H14 | 119.7 |
C18—C3—H3 | 109.9 | C16—C15—C14 | 119.74 (18) |
C2—C3—H3 | 109.9 | C16—C15—H15 | 120.1 |
C4—C3—H3 | 109.9 | C14—C15—H15 | 120.1 |
O1—C4—C5 | 109.25 (12) | C15—C16—C17 | 120.32 (19) |
O1—C4—C3 | 106.39 (12) | C15—C16—H16 | 119.8 |
C5—C4—C3 | 112.63 (13) | C17—C16—H16 | 119.8 |
O1—C4—H4 | 109.5 | C16—C17—C12 | 120.24 (18) |
C5—C4—H4 | 109.5 | C16—C17—H17 | 119.9 |
C3—C4—H4 | 109.5 | C12—C17—H17 | 119.9 |
O2—C5—C6 | 121.97 (15) | C23—C18—C19 | 117.96 (15) |
O2—C5—C4 | 120.00 (14) | C23—C18—C3 | 120.79 (15) |
C6—C5—C4 | 118.02 (14) | C19—C18—C3 | 121.13 (14) |
C11—C6—C7 | 118.72 (16) | C20—C19—C18 | 120.66 (16) |
C11—C6—C5 | 118.71 (15) | C20—C19—H19 | 119.7 |
C7—C6—C5 | 122.57 (15) | C18—C19—H19 | 119.7 |
C8—C7—C6 | 120.46 (17) | C21—C20—C19 | 120.59 (18) |
C8—C7—H7 | 119.8 | C21—C20—H20 | 119.7 |
C6—C7—H7 | 119.8 | C19—C20—H20 | 119.7 |
C9—C8—C7 | 120.05 (18) | C22—C21—C20 | 119.37 (18) |
C9—C8—H8 | 120.0 | C22—C21—H21 | 120.3 |
C7—C8—H8 | 120.0 | C20—C21—H21 | 120.3 |
C8—C9—C10 | 119.96 (18) | C21—C22—C23 | 120.77 (18) |
C8—C9—H9 | 120.0 | C21—C22—H22 | 119.6 |
C10—C9—H9 | 120.0 | C23—C22—H22 | 119.6 |
C9—C10—C11 | 120.62 (18) | C18—C23—C22 | 120.63 (18) |
C9—C10—H10 | 119.7 | C18—C23—H23 | 119.7 |
C11—C10—H10 | 119.7 | C22—C23—H23 | 119.7 |
C10—C11—C6 | 120.17 (17) | N1—C24—C2 | 177.0 (2) |
C10—C11—H11 | 119.9 | ||
C4—O1—C1—C2 | −9.45 (18) | C8—C9—C10—C11 | 0.2 (3) |
C4—O1—C1—C12 | 169.86 (13) | C9—C10—C11—C6 | 0.6 (3) |
O1—C1—C2—C24 | 177.16 (15) | C7—C6—C11—C10 | −0.6 (3) |
C12—C1—C2—C24 | −2.0 (3) | C5—C6—C11—C10 | 179.74 (17) |
O1—C1—C2—C3 | −3.50 (19) | C2—C1—C12—C13 | 153.06 (19) |
C12—C1—C2—C3 | 177.34 (16) | O1—C1—C12—C13 | −26.1 (2) |
C1—C2—C3—C18 | −109.07 (15) | C2—C1—C12—C17 | −26.5 (3) |
C24—C2—C3—C18 | 70.31 (19) | O1—C1—C12—C17 | 154.34 (15) |
C1—C2—C3—C4 | 13.56 (16) | C17—C12—C13—C14 | 1.0 (3) |
C24—C2—C3—C4 | −167.06 (15) | C1—C12—C13—C14 | −178.61 (17) |
C1—O1—C4—C5 | −103.83 (13) | C12—C13—C14—C15 | −1.1 (3) |
C1—O1—C4—C3 | 18.00 (16) | C13—C14—C15—C16 | 0.6 (3) |
C18—C3—C4—O1 | 101.41 (15) | C14—C15—C16—C17 | 0.1 (3) |
C2—C3—C4—O1 | −18.39 (15) | C15—C16—C17—C12 | −0.2 (3) |
C18—C3—C4—C5 | −138.92 (14) | C13—C12—C17—C16 | −0.3 (3) |
C2—C3—C4—C5 | 101.28 (14) | C1—C12—C17—C16 | 179.27 (16) |
O1—C4—C5—O2 | 4.62 (19) | C2—C3—C18—C23 | −103.03 (18) |
C3—C4—C5—O2 | −113.38 (16) | C4—C3—C18—C23 | 144.42 (16) |
O1—C4—C5—C6 | −176.36 (12) | C2—C3—C18—C19 | 72.97 (17) |
C3—C4—C5—C6 | 65.64 (17) | C4—C3—C18—C19 | −39.6 (2) |
O2—C5—C6—C11 | 7.9 (2) | C23—C18—C19—C20 | 0.0 (2) |
C4—C5—C6—C11 | −171.09 (15) | C3—C18—C19—C20 | −176.12 (14) |
O2—C5—C6—C7 | −171.69 (15) | C18—C19—C20—C21 | 0.5 (3) |
C4—C5—C6—C7 | 9.3 (2) | C19—C20—C21—C22 | −0.3 (3) |
C11—C6—C7—C8 | −0.1 (3) | C20—C21—C22—C23 | −0.4 (3) |
C5—C6—C7—C8 | 179.46 (16) | C19—C18—C23—C22 | −0.7 (3) |
C6—C7—C8—C9 | 1.0 (3) | C3—C18—C23—C22 | 175.45 (16) |
C7—C8—C9—C10 | −1.0 (3) | C21—C22—C23—C18 | 0.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···N1i | 0.93 | 2.63 | 3.487 (2) | 154 |
C21—H21···O2ii | 0.93 | 2.58 | 3.277 (2) | 132 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···N1i | 0.93 | 2.63 | 3.487 (2) | 153.9 |
C21—H21···O2ii | 0.93 | 2.58 | 3.277 (2) | 131.7 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2. |