organic compounds
5-Benzoyl-2-(1H-indol-3-yl)-4-[4-(propan-2-yl)phenyl]-4,5-dihydrofuran-3-carbonitrile
aDepartment of Physics, Thiagarajar College, Madurai 625 009, India, and bSchool of Chemistry, Madurai Kamaraj University, Madurai 625 021, India
*Correspondence e-mail: mailtorvkk@yahoo.co.in
In the title compound, C29H24N2O2, the hydrofuran ring is twisted with puckering parameters Q = 0.1553 (16) Å and φ = 305.0 (6)°. In the crystal, the graph-set motifs of the interaction pattern are an R22(16) motif involving dimers through N—H⋯N hydrogen bonds across centres of inversion and a C(6) motif through C—H⋯O hydrogen-bond between glide-related molecules. Together, these generate [101] ladder-like chains.
Related literature
For related structures, see: Suresh et al. (2012a,b,c). For discussion on aromatic interactions, see: Bloom & Wheeler (2011); Martinez & Iverson (2012). For graph-set motifs, see: Bernstein et al. (1995). For puckering analysis, see: Cremer & Pople (1975).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536812046764/rz5022sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812046764/rz5022Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812046764/rz5022Isup3.cml
To a stirred mixture of 2-(1H-indole-3-carbonyl)-3-(4-isopropylphenyl)acrylonitrile (1.0 eq) and phenacylpyridinium bromide (1.0 eq) in water (10 ml) was added drop wise triethylamine (0.25 eq) at room temperature. The resulting clear solution, that slowly became turbid, was stirred at room temperature for 1.5 h. Then the separated free flowing solid was filtered and washed with methanol (3 ml) to afford the compound as pale yellow solid. Yield 87%; m.p. 508 K.
All hydrogen atoms except those participating in the hydrogen-bonding were included into the model at geometrically calculated positions (C—H target distance 0.96 Å for methyl hydrogen atoms, 0.93 Å for all others) and refined using a riding model. The torsion angle of the methyl groups involving C7 and C8 were allowed to refine. The Uiso values of all hydrogen atoms were constrained to 1.2 times Ueq (1.5 times for methyl H atoms) of the respective atom to which the hydrogen atom binds. The positions of the hydrogen atoms bound to N2, C33 and C56 were allowed to refine isotropically. A reflection (1 0 1) partially obstructed by the primary beam stop was omitted from the refinement.
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C29H24N2O2 | F(000) = 912 |
Mr = 432.50 | Dx = 1.251 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4455 reflections |
a = 17.1073 (4) Å | θ = 2.5–25.9° |
b = 8.1230 (2) Å | µ = 0.08 mm−1 |
c = 17.6160 (4) Å | T = 298 K |
β = 110.325 (1)° | Block, yellow |
V = 2295.55 (9) Å3 | 0.30 × 0.24 × 0.18 mm |
Z = 4 |
Bruker SMART APEXII CCD diffractometer | 4455 independent reflections |
Radiation source: fine-focus sealed tube | 2979 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ω and ϕ scans | θmax = 25.9°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −21→20 |
Tmin = 0.978, Tmax = 0.986 | k = −9→9 |
21711 measured reflections | l = −21→21 |
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)] = 0.040 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.115 | w = 1/[σ2(Fo2) + (0.0478P)2 + 0.3844P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
4455 reflections | Δρmax = 0.14 e Å−3 |
313 parameters | Δρmin = −0.15 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0037 (8) |
C29H24N2O2 | V = 2295.55 (9) Å3 |
Mr = 432.50 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 17.1073 (4) Å | µ = 0.08 mm−1 |
b = 8.1230 (2) Å | T = 298 K |
c = 17.6160 (4) Å | 0.30 × 0.24 × 0.18 mm |
β = 110.325 (1)° |
Bruker SMART APEXII CCD diffractometer | 4455 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 2979 reflections with I > 2σ(I) |
Tmin = 0.978, Tmax = 0.986 | Rint = 0.031 |
21711 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.115 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.14 e Å−3 |
4455 reflections | Δρmin = −0.15 e Å−3 |
313 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. |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.27185 (7) | 0.17860 (13) | 0.26234 (6) | 0.0553 (3) | |
O2 | 0.14529 (8) | 0.34499 (18) | 0.16547 (7) | 0.0792 (4) | |
N1 | 0.49191 (10) | 0.5602 (2) | 0.31131 (9) | 0.0752 (5) | |
N2 | 0.40406 (11) | 0.3263 (2) | 0.52408 (9) | 0.0694 (5) | |
H2 | 0.4434 (13) | 0.352 (3) | 0.5722 (13) | 0.088 (6)* | |
C38 | 0.41572 (11) | 0.3360 (2) | 0.45193 (10) | 0.0611 (5) | |
H38 | 0.4652 | 0.3669 | 0.4451 | 0.073* | |
C37 | 0.32392 (12) | 0.2788 (2) | 0.51144 (10) | 0.0623 (5) | |
C36 | 0.28453 (16) | 0.2536 (3) | 0.56731 (12) | 0.0808 (6) | |
H36 | 0.3124 | 0.2690 | 0.6224 | 0.097* | |
C35 | 0.20349 (17) | 0.2056 (3) | 0.53802 (15) | 0.0907 (7) | |
H35 | 0.1756 | 0.1862 | 0.5740 | 0.109* | |
C34 | 0.16088 (14) | 0.1847 (3) | 0.45517 (14) | 0.0828 (6) | |
H34 | 0.1051 | 0.1537 | 0.4371 | 0.099* | |
C33 | 0.20012 (12) | 0.2091 (2) | 0.39978 (12) | 0.0640 (5) | |
H33 | 0.1721 (10) | 0.194 (2) | 0.3426 (10) | 0.063 (5)* | |
C32 | 0.28362 (11) | 0.25594 (19) | 0.42818 (9) | 0.0527 (4) | |
C31 | 0.34395 (10) | 0.29363 (19) | 0.39077 (9) | 0.0510 (4) | |
C3 | 0.33352 (9) | 0.28117 (19) | 0.30620 (9) | 0.0481 (4) | |
C2 | 0.37493 (10) | 0.34966 (19) | 0.26182 (9) | 0.0486 (4) | |
C1 | 0.43942 (11) | 0.4654 (2) | 0.28977 (9) | 0.0544 (4) | |
C5 | 0.34552 (9) | 0.27757 (19) | 0.17735 (9) | 0.0477 (4) | |
H5 | 0.3302 | 0.3663 | 0.1371 | 0.057* | |
C4 | 0.26595 (9) | 0.18830 (19) | 0.17900 (8) | 0.0483 (4) | |
H4 | 0.2641 | 0.0769 | 0.1571 | 0.058* | |
C41 | 0.18682 (10) | 0.2796 (2) | 0.13117 (9) | 0.0505 (4) | |
C42 | 0.16376 (9) | 0.28783 (19) | 0.04210 (9) | 0.0472 (4) | |
C43 | 0.20139 (11) | 0.1912 (2) | 0.00015 (10) | 0.0613 (5) | |
H43 | 0.2440 | 0.1194 | 0.0281 | 0.074* | |
C44 | 0.17592 (13) | 0.2007 (3) | −0.08313 (11) | 0.0751 (6) | |
H44 | 0.2012 | 0.1348 | −0.1111 | 0.090* | |
C45 | 0.11360 (13) | 0.3069 (2) | −0.12478 (11) | 0.0725 (5) | |
H45 | 0.0966 | 0.3129 | −0.1809 | 0.087* | |
C46 | 0.07638 (12) | 0.4040 (3) | −0.08392 (11) | 0.0741 (5) | |
H46 | 0.0343 | 0.4767 | −0.1121 | 0.089* | |
C47 | 0.10122 (11) | 0.3943 (2) | −0.00096 (10) | 0.0633 (5) | |
H47 | 0.0755 | 0.4604 | 0.0265 | 0.076* | |
C51 | 0.41055 (9) | 0.16822 (19) | 0.16311 (9) | 0.0486 (4) | |
C52 | 0.44866 (12) | 0.2118 (2) | 0.10860 (11) | 0.0718 (5) | |
H52 | 0.4313 | 0.3059 | 0.0772 | 0.086* | |
C53 | 0.51201 (13) | 0.1176 (3) | 0.10024 (12) | 0.0803 (6) | |
H53 | 0.5365 | 0.1498 | 0.0630 | 0.096* | |
C54 | 0.54025 (11) | −0.0221 (2) | 0.14503 (10) | 0.0631 (5) | |
C55 | 0.49997 (10) | −0.0680 (2) | 0.19778 (10) | 0.0579 (4) | |
H55 | 0.5163 | −0.1640 | 0.2280 | 0.070* | |
C56 | 0.43633 (10) | 0.0251 (2) | 0.20650 (9) | 0.0518 (4) | |
H56 | 0.4086 (9) | −0.0097 (19) | 0.2440 (9) | 0.059 (4)* | |
C6 | 0.61471 (13) | −0.1150 (3) | 0.14021 (12) | 0.0827 (6) | |
H6 | 0.6245 | −0.0765 | 0.0916 | 0.099* | |
C7 | 0.69188 (13) | −0.0692 (4) | 0.21299 (13) | 0.1129 (9) | |
H7A | 0.6812 | −0.0901 | 0.2621 | 0.169* | |
H7B | 0.7043 | 0.0453 | 0.2101 | 0.169* | |
H7C | 0.7385 | −0.1343 | 0.2123 | 0.169* | |
C8 | 0.60164 (18) | −0.2977 (3) | 0.1318 (2) | 0.1309 (11) | |
H8A | 0.5946 | −0.3408 | 0.1797 | 0.196* | |
H8B | 0.6492 | −0.3484 | 0.1244 | 0.196* | |
H8C | 0.5528 | −0.3208 | 0.0857 | 0.196* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0631 (7) | 0.0602 (7) | 0.0400 (6) | −0.0138 (6) | 0.0145 (5) | −0.0035 (5) |
O2 | 0.0800 (9) | 0.1019 (10) | 0.0621 (8) | 0.0212 (8) | 0.0331 (7) | −0.0097 (7) |
N1 | 0.0769 (11) | 0.0719 (11) | 0.0629 (10) | −0.0211 (9) | 0.0067 (8) | −0.0012 (8) |
N2 | 0.0827 (12) | 0.0747 (11) | 0.0406 (9) | −0.0067 (9) | 0.0087 (8) | −0.0032 (7) |
C38 | 0.0699 (11) | 0.0623 (11) | 0.0458 (10) | −0.0031 (9) | 0.0134 (8) | −0.0008 (8) |
C37 | 0.0830 (14) | 0.0546 (10) | 0.0484 (10) | 0.0046 (10) | 0.0217 (9) | 0.0016 (8) |
C36 | 0.1129 (18) | 0.0812 (14) | 0.0558 (12) | 0.0064 (13) | 0.0389 (12) | 0.0030 (10) |
C35 | 0.1152 (19) | 0.0943 (17) | 0.0842 (16) | 0.0108 (15) | 0.0619 (15) | 0.0097 (13) |
C34 | 0.0788 (14) | 0.0842 (15) | 0.0955 (17) | 0.0055 (12) | 0.0432 (13) | 0.0062 (12) |
C33 | 0.0687 (12) | 0.0613 (11) | 0.0629 (12) | 0.0076 (9) | 0.0242 (10) | 0.0011 (9) |
C32 | 0.0651 (11) | 0.0443 (9) | 0.0472 (9) | 0.0069 (8) | 0.0176 (8) | 0.0011 (7) |
C31 | 0.0603 (10) | 0.0470 (9) | 0.0413 (9) | 0.0028 (8) | 0.0120 (7) | 0.0004 (7) |
C3 | 0.0512 (9) | 0.0442 (9) | 0.0435 (9) | 0.0018 (7) | 0.0094 (7) | −0.0024 (7) |
C2 | 0.0511 (9) | 0.0465 (9) | 0.0438 (8) | −0.0020 (8) | 0.0107 (7) | −0.0027 (7) |
C1 | 0.0584 (10) | 0.0531 (10) | 0.0450 (9) | −0.0036 (9) | 0.0095 (8) | −0.0004 (8) |
C5 | 0.0520 (9) | 0.0473 (9) | 0.0402 (8) | −0.0047 (7) | 0.0115 (7) | 0.0002 (7) |
C4 | 0.0556 (9) | 0.0490 (9) | 0.0394 (8) | −0.0055 (7) | 0.0155 (7) | −0.0059 (7) |
C41 | 0.0511 (9) | 0.0531 (9) | 0.0485 (9) | −0.0050 (8) | 0.0188 (8) | −0.0101 (7) |
C42 | 0.0453 (9) | 0.0486 (9) | 0.0460 (9) | −0.0057 (7) | 0.0137 (7) | −0.0074 (7) |
C43 | 0.0677 (11) | 0.0652 (11) | 0.0506 (10) | 0.0086 (9) | 0.0199 (8) | −0.0026 (8) |
C44 | 0.0912 (14) | 0.0846 (14) | 0.0548 (11) | 0.0057 (12) | 0.0320 (11) | −0.0082 (10) |
C45 | 0.0856 (14) | 0.0795 (14) | 0.0462 (10) | −0.0104 (11) | 0.0149 (10) | 0.0021 (10) |
C46 | 0.0728 (12) | 0.0755 (13) | 0.0581 (12) | 0.0063 (10) | 0.0030 (10) | 0.0016 (10) |
C47 | 0.0568 (10) | 0.0696 (12) | 0.0568 (11) | 0.0039 (9) | 0.0110 (8) | −0.0088 (9) |
C51 | 0.0525 (9) | 0.0532 (9) | 0.0392 (8) | −0.0068 (8) | 0.0148 (7) | −0.0013 (7) |
C52 | 0.0848 (13) | 0.0751 (13) | 0.0671 (12) | 0.0079 (11) | 0.0410 (11) | 0.0220 (10) |
C53 | 0.0857 (14) | 0.1008 (16) | 0.0742 (13) | 0.0119 (12) | 0.0528 (11) | 0.0227 (12) |
C54 | 0.0628 (11) | 0.0780 (13) | 0.0539 (10) | 0.0029 (10) | 0.0271 (9) | −0.0005 (9) |
C55 | 0.0620 (11) | 0.0598 (11) | 0.0529 (10) | 0.0034 (9) | 0.0212 (8) | 0.0046 (8) |
C56 | 0.0579 (10) | 0.0575 (10) | 0.0445 (9) | −0.0049 (8) | 0.0234 (8) | 0.0026 (8) |
C6 | 0.0760 (13) | 0.1117 (18) | 0.0713 (13) | 0.0184 (13) | 0.0393 (11) | 0.0067 (12) |
C7 | 0.0725 (15) | 0.190 (3) | 0.0792 (16) | 0.0226 (16) | 0.0300 (13) | 0.0053 (16) |
C8 | 0.125 (2) | 0.110 (2) | 0.182 (3) | 0.0356 (18) | 0.084 (2) | −0.005 (2) |
O1—C3 | 1.3557 (18) | C42—C43 | 1.381 (2) |
O1—C4 | 1.4384 (17) | C43—C44 | 1.380 (2) |
O2—C41 | 1.2043 (18) | C43—H43 | 0.9300 |
N1—C1 | 1.143 (2) | C44—C45 | 1.370 (3) |
N2—C38 | 1.356 (2) | C44—H44 | 0.9300 |
N2—C37 | 1.366 (2) | C45—C46 | 1.365 (3) |
N2—H2 | 0.91 (2) | C45—H45 | 0.9300 |
C38—C31 | 1.367 (2) | C46—C47 | 1.375 (2) |
C38—H38 | 0.9300 | C46—H46 | 0.9300 |
C37—C36 | 1.388 (3) | C47—H47 | 0.9300 |
C37—C32 | 1.399 (2) | C51—C56 | 1.377 (2) |
C36—C35 | 1.358 (3) | C51—C52 | 1.381 (2) |
C36—H36 | 0.9300 | C52—C53 | 1.376 (3) |
C35—C34 | 1.397 (3) | C52—H52 | 0.9300 |
C35—H35 | 0.9300 | C53—C54 | 1.371 (3) |
C34—C33 | 1.378 (3) | C53—H53 | 0.9300 |
C34—H34 | 0.9300 | C54—C55 | 1.387 (2) |
C33—C32 | 1.392 (2) | C54—C6 | 1.508 (3) |
C33—H33 | 0.961 (16) | C55—C56 | 1.377 (2) |
C32—C31 | 1.437 (2) | C55—H55 | 0.9300 |
C31—C3 | 1.441 (2) | C56—H56 | 0.978 (15) |
C3—C2 | 1.344 (2) | C6—C8 | 1.501 (3) |
C2—C1 | 1.402 (2) | C6—C7 | 1.533 (3) |
C2—C5 | 1.513 (2) | C6—H6 | 0.9800 |
C5—C51 | 1.511 (2) | C7—H7A | 0.9600 |
C5—C4 | 1.552 (2) | C7—H7B | 0.9600 |
C5—H5 | 0.9800 | C7—H7C | 0.9600 |
C4—C41 | 1.516 (2) | C8—H8A | 0.9600 |
C4—H4 | 0.9800 | C8—H8B | 0.9600 |
C41—C42 | 1.480 (2) | C8—H8C | 0.9600 |
C42—C47 | 1.380 (2) | ||
C3—O1—C4 | 108.23 (11) | C43—C42—C41 | 122.63 (15) |
C38—N2—C37 | 109.26 (16) | C44—C43—C42 | 120.21 (17) |
C38—N2—H2 | 124.0 (13) | C44—C43—H43 | 119.9 |
C37—N2—H2 | 126.6 (12) | C42—C43—H43 | 119.9 |
N2—C38—C31 | 109.88 (16) | C45—C44—C43 | 120.31 (17) |
N2—C38—H38 | 125.1 | C45—C44—H44 | 119.8 |
C31—C38—H38 | 125.1 | C43—C44—H44 | 119.8 |
N2—C37—C36 | 129.28 (18) | C46—C45—C44 | 120.01 (17) |
N2—C37—C32 | 108.03 (15) | C46—C45—H45 | 120.0 |
C36—C37—C32 | 122.68 (19) | C44—C45—H45 | 120.0 |
C35—C36—C37 | 117.1 (2) | C45—C46—C47 | 119.89 (18) |
C35—C36—H36 | 121.4 | C45—C46—H46 | 120.1 |
C37—C36—H36 | 121.4 | C47—C46—H46 | 120.1 |
C36—C35—C34 | 121.69 (19) | C46—C47—C42 | 120.99 (17) |
C36—C35—H35 | 119.2 | C46—C47—H47 | 119.5 |
C34—C35—H35 | 119.2 | C42—C47—H47 | 119.5 |
C33—C34—C35 | 121.1 (2) | C56—C51—C52 | 117.70 (15) |
C33—C34—H34 | 119.4 | C56—C51—C5 | 121.09 (13) |
C35—C34—H34 | 119.4 | C52—C51—C5 | 121.15 (15) |
C34—C33—C32 | 118.44 (19) | C53—C52—C51 | 120.76 (17) |
C34—C33—H33 | 122.3 (10) | C53—C52—H52 | 119.6 |
C32—C33—H33 | 119.2 (10) | C51—C52—H52 | 119.6 |
C33—C32—C37 | 118.90 (16) | C54—C53—C52 | 122.15 (16) |
C33—C32—C31 | 134.73 (15) | C54—C53—H53 | 118.9 |
C37—C32—C31 | 106.34 (15) | C52—C53—H53 | 118.9 |
C38—C31—C32 | 106.48 (14) | C53—C54—C55 | 116.79 (16) |
C38—C31—C3 | 125.98 (15) | C53—C54—C6 | 121.17 (16) |
C32—C31—C3 | 127.46 (15) | C55—C54—C6 | 121.95 (17) |
C2—C3—O1 | 112.70 (13) | C56—C55—C54 | 121.53 (17) |
C2—C3—C31 | 132.15 (15) | C56—C55—H55 | 119.2 |
O1—C3—C31 | 115.13 (13) | C54—C55—H55 | 119.2 |
C3—C2—C1 | 125.62 (14) | C51—C56—C55 | 121.00 (15) |
C3—C2—C5 | 110.44 (13) | C51—C56—H56 | 118.8 (9) |
C1—C2—C5 | 123.86 (14) | C55—C56—H56 | 120.2 (9) |
N1—C1—C2 | 178.90 (18) | C8—C6—C54 | 113.64 (18) |
C51—C5—C2 | 112.23 (12) | C8—C6—C7 | 112.2 (2) |
C51—C5—C4 | 115.45 (13) | C54—C6—C7 | 109.29 (17) |
C2—C5—C4 | 99.01 (11) | C8—C6—H6 | 107.1 |
C51—C5—H5 | 109.9 | C54—C6—H6 | 107.1 |
C2—C5—H5 | 109.9 | C7—C6—H6 | 107.1 |
C4—C5—H5 | 109.9 | C6—C7—H7A | 109.5 |
O1—C4—C41 | 109.06 (12) | C6—C7—H7B | 109.5 |
O1—C4—C5 | 107.08 (11) | H7A—C7—H7B | 109.5 |
C41—C4—C5 | 112.38 (12) | C6—C7—H7C | 109.5 |
O1—C4—H4 | 109.4 | H7A—C7—H7C | 109.5 |
C41—C4—H4 | 109.4 | H7B—C7—H7C | 109.5 |
C5—C4—H4 | 109.4 | C6—C8—H8A | 109.5 |
O2—C41—C42 | 121.68 (15) | C6—C8—H8B | 109.5 |
O2—C41—C4 | 120.35 (14) | H8A—C8—H8B | 109.5 |
C42—C41—C4 | 117.96 (13) | C6—C8—H8C | 109.5 |
C47—C42—C43 | 118.59 (15) | H8A—C8—H8C | 109.5 |
C47—C42—C41 | 118.78 (14) | H8B—C8—H8C | 109.5 |
C37—N2—C38—C31 | −0.6 (2) | C2—C5—C4—O1 | −15.46 (14) |
C38—N2—C37—C36 | −179.78 (19) | C51—C5—C4—C41 | −135.75 (13) |
C38—N2—C37—C32 | 0.6 (2) | C2—C5—C4—C41 | 104.28 (13) |
N2—C37—C36—C35 | −179.8 (2) | O1—C4—C41—O2 | 7.6 (2) |
C32—C37—C36—C35 | −0.3 (3) | C5—C4—C41—O2 | −110.94 (17) |
C37—C36—C35—C34 | −1.0 (3) | O1—C4—C41—C42 | −173.49 (12) |
C36—C35—C34—C33 | 1.3 (3) | C5—C4—C41—C42 | 67.93 (17) |
C35—C34—C33—C32 | −0.2 (3) | O2—C41—C42—C47 | 10.5 (2) |
C34—C33—C32—C37 | −1.0 (3) | C4—C41—C42—C47 | −168.32 (14) |
C34—C33—C32—C31 | −179.20 (18) | O2—C41—C42—C43 | −168.36 (17) |
N2—C37—C32—C33 | −179.12 (16) | C4—C41—C42—C43 | 12.8 (2) |
C36—C37—C32—C33 | 1.3 (3) | C47—C42—C43—C44 | −0.6 (3) |
N2—C37—C32—C31 | −0.42 (19) | C41—C42—C43—C44 | 178.27 (16) |
C36—C37—C32—C31 | 179.96 (16) | C42—C43—C44—C45 | 0.5 (3) |
N2—C38—C31—C32 | 0.32 (19) | C43—C44—C45—C46 | 0.0 (3) |
N2—C38—C31—C3 | −176.61 (15) | C44—C45—C46—C47 | −0.4 (3) |
C33—C32—C31—C38 | 178.46 (19) | C45—C46—C47—C42 | 0.3 (3) |
C37—C32—C31—C38 | 0.07 (18) | C43—C42—C47—C46 | 0.3 (3) |
C33—C32—C31—C3 | −4.7 (3) | C41—C42—C47—C46 | −178.69 (16) |
C37—C32—C31—C3 | 176.94 (15) | C2—C5—C51—C56 | 63.99 (19) |
C4—O1—C3—C2 | −5.21 (17) | C4—C5—C51—C56 | −48.45 (19) |
C4—O1—C3—C31 | 176.25 (13) | C2—C5—C51—C52 | −113.25 (17) |
C38—C31—C3—C2 | −23.4 (3) | C4—C5—C51—C52 | 134.30 (16) |
C32—C31—C3—C2 | 160.29 (17) | C56—C51—C52—C53 | −2.1 (3) |
C38—C31—C3—O1 | 154.78 (15) | C5—C51—C52—C53 | 175.27 (17) |
C32—C31—C3—O1 | −21.5 (2) | C51—C52—C53—C54 | −0.1 (3) |
O1—C3—C2—C1 | 177.33 (14) | C52—C53—C54—C55 | 2.1 (3) |
C31—C3—C2—C1 | −4.4 (3) | C52—C53—C54—C6 | −174.53 (19) |
O1—C3—C2—C5 | −5.75 (18) | C53—C54—C55—C56 | −1.9 (3) |
C31—C3—C2—C5 | 172.48 (16) | C6—C54—C55—C56 | 174.67 (17) |
C3—C2—C5—C51 | −109.41 (15) | C52—C51—C56—C55 | 2.2 (2) |
C1—C2—C5—C51 | 67.58 (19) | C5—C51—C56—C55 | −175.12 (14) |
C3—C2—C5—C4 | 12.92 (16) | C54—C55—C56—C51 | −0.2 (3) |
C1—C2—C5—C4 | −170.09 (15) | C53—C54—C6—C8 | −133.9 (2) |
C3—O1—C4—C41 | −108.29 (13) | C55—C54—C6—C8 | 49.6 (3) |
C3—O1—C4—C5 | 13.55 (15) | C53—C54—C6—C7 | 99.9 (2) |
C51—C5—C4—O1 | 104.52 (14) | C55—C54—C6—C7 | −76.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C33—H33···O1 | 0.961 (16) | 2.569 (15) | 3.081 (2) | 113.5 (11) |
N2—H2···N1i | 0.91 (2) | 2.09 (2) | 2.973 (2) | 165.2 (17) |
C56—H56···O2ii | 0.978 (15) | 2.411 (16) | 3.371 (2) | 166.9 (13) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1/2, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C29H24N2O2 |
Mr | 432.50 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 17.1073 (4), 8.1230 (2), 17.6160 (4) |
β (°) | 110.325 (1) |
V (Å3) | 2295.55 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.30 × 0.24 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.978, 0.986 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21711, 4455, 2979 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.615 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.115, 1.03 |
No. of reflections | 4455 |
No. of parameters | 313 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.14, −0.15 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C33—H33···O1 | 0.961 (16) | 2.569 (15) | 3.081 (2) | 113.5 (11) |
N2—H2···N1i | 0.91 (2) | 2.09 (2) | 2.973 (2) | 165.2 (17) |
C56—H56···O2ii | 0.978 (15) | 2.411 (16) | 3.371 (2) | 166.9 (13) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1/2, y−1/2, −z+1/2. |
Acknowledgements
The authors thank the SAIF, IIT, Chennai, for the data collection. PG thanks the CSIR, India, for a Research Fellowship. SP thanks the Department of Science and Technology, New Delhi, for funding the Indo-Spanish collaborative major research project (grant DST/INT/SPAIN/ 09).
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
In the molecule of the title compound (Fig. 1), the puckering (Cremer & Pople, 1975) of the furan ring is twisted (4T5) about the C4—C5 bond with Q = 0.1553 (16) Å and ϕ = 305.0 (6)°. The geometry of the N—H···N and C—H···O interactions that characterize the crystal packing (Table 1) are similar to its 4-phenyl analogue (Suresh et al., 2012a). The graph-set motifs (Bernstein et al., 1995) that characterize the intermolecular interaction pattern are a R22(16) involving dimers through N—H···N hydrogen bonds across centres of inversion and a C(6) motif through C—H···O hydrogen-bond between glide-related molecules (Fig. 2). The crystal structure may be visualized as zero-dimensional N—H···N mediated centrosymmetric dimeric units linked via C—H···O linkages to form a supramolecular ladder parallel to the b axis that extends along the [101] direction (Fig. 3). The non-covalent crystal packing interactions are closely related to that observed in the 4-phenyl analogue and distinctly differs from those of the 4-methylphenyl (Suresh et al., 2012b) and 4-bromophenyl (Suresh et al., 2012c) analogues. The intramolecular C—H···O hydrogen bond generates a S(6) motif and its geometry is similar to those observed in all of the above analogues. No significant weak non-covalent crystal packing interactions involving centroids of planar rings are observed. Though it has become an acceptable norm in describing weak non-covalent interactions in terms of C—H···π and π···π interactions, some recent views (Martinez & Iverson, 2012; Bloom & Wheeler, 2011) on these interactions calls for a careful analysis while describing them in crystal structures.
The crystal structure of the title compound together with those of its analogues demonstrate the effect of substituents in drastically altering the interaction patterns while retaining the crystal system and lattice type.