organic compounds
4,6-Di-tert-butyl-2-({[4-(diethylamino)phenyl]imino}methyl)phenol
aDepartment of Chemistry, Vaigai College of Engineering, Madurai 625 122, Tamil Nadu, India, bDepartment of Chemistry, University of Pitesti, Pitesti 11040, Romania, cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and dPG & Research Department of Chemistry, Chikkanna Government Arts College, Tiruppur 641 602, Tamil Nadu, India
*Correspondence e-mail: chakkaravarthi_2005@yahoo.com, rajagopal18@yahoo.com
The title compound, C25H36N2O, adopts an E conformation about the C=N bond. The dihedral angle between the aromatic rings is 35.6 (6)°. The molecular structure is stabilized by an O—H⋯N hydrogen bond, which forms an S(6) loop, and weak C—H⋯O contacts. Weak intermolecular C—H⋯π interactions are observed in the crystal packing. The diethylamino group has rotational disorder with site occupancies of 0.85 (2) and 0.15 (2) for the major and minor components, respectively. The structure was refined as a three-component twin.
CCDC reference: 982393
Structure description
Schiff base derivatives are a biologically versatile class of compounds possessing diverse activities, such as anti-inflammatory (Alam et al., 2012), anti-bacterial (Sondhi et al., 2006), anti-fungal (Jarrahpour et al., 2007). We herein, report the synthesis and of the title compound (Fig. 1). The bond distances are comparable with similar structures (Rani et al., 2015, 2017).
The dihedral angle between the best planes through the aromatic rings (C5–C10 and C12–C17) is 35.6 (6)°. The C11=N2 bond adopts the E conformation, which allows formation of an intramolecular O1—H1⋯N2 hydrogen bond, resulting in an S(6) ring-motif (Fig. 1 and Table 1). The molecular structure is stabilized by an O—H⋯N hydrogen bond and weak C—H⋯O contacts (Table 1). Weak intermolecular C—H⋯π interactions are also observed in the crystal packing (Table 1).
Synthesis and crystallization
An ethanolic solution of N1,N1-diethylbenzene-1,4-diamine (5 mmol) was magnetically stirred in a round-bottom flask followed by dropwise addition of 3,5-di-tert-butyl-2-hydroxybenzaldehyde (5 mmol) containing 2–3 drops of glacial acetic acid. The reaction mixture was then refluxed for 3 h and upon cooling to room temperature, a yellow precipitate was separated out from the mixture. The precipitate was washed with ethanol and dried in vacuo over anhydrous CaCl2. Single crystals suitable for X–ray diffraction were obtained by slow evaporation of a solution of the title compound in DMF at room temperature.
Refinement
Crystal data, data collection and structure . The diethylamine group has rotational disorder with occupancies of 0.85 (2) for the major component (atoms C1–C4) and 0.15 (2) for the minor component (atoms C1′–C4′). The command DFIX was used to restrain the N—C and C—C bond lengths involving these atoms to 1.43 (1) and 1.55 (1) Å, respectively. The same anisotropic displacement parameters were used for the disordered equivalent C atoms (C1 & C1′, C2 & C2′, C3 & C3′ and C4 & C4′) using the EADP command. Rigid bond restraints were used for N1—C2′, N1—C4′, N1—C2, N1—C4, N2—C8, C3′-C4′, C5—C6, C3—C4, C6—C7, C18—C21, C15—C16, and C1—C2 bonds, using the DELU command. The structure was refined as a three-component twin. In the absence of significant effects, the parameter is meaningless. Reflections (20), (10) and (05) were omitted in the final cycles of refinement.
details are summarized in Table 2Structural data
CCDC reference: 982393
https://doi.org/10.1107/S2414314617005727/vm4022sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617005727/vm4022Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617005727/vm4022Isup3.cml
Data collection: APEX2 (Bruker, 2004); cell
SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015) and PLATON (Spek, 2009).C25H36N2O | F(000) = 416 |
Mr = 380.56 | Dx = 1.079 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.9303 (15) Å | Cell parameters from 3084 reflections |
b = 15.572 (3) Å | θ = 2.4–20.5° |
c = 9.4824 (16) Å | µ = 0.07 mm−1 |
β = 117.320 (8)° | T = 295 K |
V = 1171.6 (3) Å3 | Block, yellow |
Z = 2 | 0.30 × 0.28 × 0.24 mm |
Bruker APEXII CCD diffractometer | 8432 independent reflections |
Radiation source: fine-focus sealed tube | 6509 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.000 |
ω and φ scan | θmax = 22.9°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −9→9 |
Tmin = 0.921, Tmax = 0.984 | k = −17→17 |
8432 measured reflections | l = −10→10 |
Refinement on F2 | 26 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.062 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.189 | w = 1/[σ2(Fo2) + (0.0973P)2 + 0.2985P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
8432 reflections | Δρmax = 0.20 e Å−3 |
277 parameters | Δρmin = −0.22 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 3-component twin. The H atom for the hydroxy group was located in a difference-Fourier map and refined with a distance restraint of 0.82 (1) Å, with Uiso(H) = 1.5Ueq(O). All other H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic CH, C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for CH2 and C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for CH3. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | −0.077 (3) | 0.5191 (13) | −0.506 (3) | 0.150 (9) | 0.85 (2) |
H1A | −0.177280 | 0.485250 | −0.557143 | 0.225* | 0.85 (2) |
H1B | −0.010074 | 0.512597 | −0.560645 | 0.225* | 0.85 (2) |
H1C | −0.012806 | 0.500182 | −0.397779 | 0.225* | 0.85 (2) |
C2 | −0.1242 (18) | 0.6139 (12) | −0.507 (2) | 0.094 (5) | 0.85 (2) |
H2A | −0.190115 | 0.632881 | −0.616152 | 0.113* | 0.85 (2) |
H2B | −0.192852 | 0.620445 | −0.453017 | 0.113* | 0.85 (2) |
C3 | −0.016 (4) | 0.7921 (17) | −0.593 (3) | 0.186 (12) | 0.85 (2) |
H3A | 0.015996 | 0.820295 | −0.665562 | 0.278* | 0.85 (2) |
H3B | −0.134618 | 0.780981 | −0.645328 | 0.278* | 0.85 (2) |
H3C | 0.011559 | 0.828409 | −0.502735 | 0.278* | 0.85 (2) |
C4 | 0.081 (2) | 0.7066 (14) | −0.5381 (18) | 0.107 (6) | 0.85 (2) |
H4A | 0.054761 | 0.669186 | −0.628333 | 0.128* | 0.85 (2) |
H4B | 0.201674 | 0.716854 | −0.485022 | 0.128* | 0.85 (2) |
C1' | −0.175 (19) | 0.563 (10) | −0.587 (14) | 0.150 (9) | 0.15 (2) |
H1'1 | −0.271543 | 0.530082 | −0.598955 | 0.225* | 0.15 (2) |
H1'2 | −0.205138 | 0.598040 | −0.678834 | 0.225* | 0.15 (2) |
H1'3 | −0.085701 | 0.524662 | −0.574063 | 0.225* | 0.15 (2) |
C2' | −0.116 (11) | 0.621 (8) | −0.438 (12) | 0.094 (5) | 0.15 (2) |
H2'1 | −0.205060 | 0.660315 | −0.448596 | 0.113* | 0.15 (2) |
H2'2 | −0.084905 | 0.586495 | −0.343194 | 0.113* | 0.15 (2) |
C3' | 0.08 (3) | 0.818 (8) | −0.517 (19) | 0.186 (12) | 0.15 (2) |
H3'1 | 0.043755 | 0.849312 | −0.613457 | 0.278* | 0.15 (2) |
H3'2 | 0.035306 | 0.847736 | −0.451956 | 0.278* | 0.15 (2) |
H3'3 | 0.196242 | 0.813633 | −0.460255 | 0.278* | 0.15 (2) |
C4' | −0.002 (14) | 0.727 (6) | −0.556 (9) | 0.107 (6) | 0.15 (2) |
H4'1 | −0.123560 | 0.733489 | −0.616586 | 0.128* | 0.15 (2) |
H4'2 | 0.036441 | 0.699583 | −0.624836 | 0.128* | 0.15 (2) |
C5 | 0.1139 (15) | 0.6770 (9) | −0.2706 (11) | 0.057 (3) | |
C6 | 0.2514 (14) | 0.7334 (8) | −0.2004 (12) | 0.067 (3) | |
H6 | 0.286148 | 0.764161 | −0.264162 | 0.080* | |
C7 | 0.3341 (14) | 0.7435 (8) | −0.0403 (12) | 0.063 (3) | |
H7 | 0.425305 | 0.780968 | 0.001366 | 0.075* | |
C8 | 0.2911 (14) | 0.7014 (7) | 0.0652 (11) | 0.052 (3) | |
C9 | 0.1524 (15) | 0.6488 (9) | −0.0054 (13) | 0.070 (3) | |
H9 | 0.115149 | 0.620270 | 0.058848 | 0.084* | |
C10 | 0.0672 (13) | 0.6366 (8) | −0.1654 (14) | 0.066 (3) | |
H10 | −0.025512 | 0.600110 | −0.206012 | 0.079* | |
C11 | 0.4023 (13) | 0.6582 (7) | 0.3275 (12) | 0.057 (3) | |
H11 | 0.354071 | 0.604812 | 0.289394 | 0.069* | |
C12 | 0.4924 (14) | 0.6693 (7) | 0.4952 (12) | 0.051 (3) | |
C13 | 0.5096 (14) | 0.6016 (7) | 0.5958 (13) | 0.060 (3) | |
H13 | 0.460269 | 0.549358 | 0.550738 | 0.072* | |
C14 | 0.5948 (13) | 0.6069 (7) | 0.7577 (13) | 0.051 (3) | |
C15 | 0.6630 (15) | 0.6864 (7) | 0.8231 (11) | 0.052 (2) | |
H15 | 0.721045 | 0.691959 | 0.932885 | 0.063* | |
C16 | 0.6464 (12) | 0.7588 (6) | 0.7274 (11) | 0.050 (3) | |
C17 | 0.5607 (12) | 0.7496 (7) | 0.5649 (11) | 0.049 (3) | |
C18 | 0.6143 (16) | 0.5287 (8) | 0.8651 (13) | 0.065 (3) | |
C19 | 0.4436 (17) | 0.4872 (10) | 0.8153 (16) | 0.094 (4) | |
H19A | 0.395662 | 0.470994 | 0.705493 | 0.141* | |
H19B | 0.370156 | 0.527204 | 0.829953 | 0.141* | |
H19C | 0.456973 | 0.437040 | 0.878934 | 0.141* | |
C20 | 0.7227 (17) | 0.4621 (10) | 0.8346 (17) | 0.093 (4) | |
H20A | 0.675752 | 0.451327 | 0.722708 | 0.140* | |
H20B | 0.724633 | 0.409644 | 0.888660 | 0.140* | |
H20C | 0.835444 | 0.483593 | 0.873406 | 0.140* | |
C21 | 0.693 (2) | 0.5511 (10) | 1.0374 (14) | 0.113 (6) | |
H21A | 0.708759 | 0.499740 | 1.098732 | 0.170* | |
H21B | 0.620636 | 0.589810 | 1.056491 | 0.170* | |
H21C | 0.800130 | 0.578005 | 1.067742 | 0.170* | |
C22 | 0.7209 (14) | 0.8462 (7) | 0.8094 (12) | 0.055 (3) | |
C23 | 0.8412 (17) | 0.8824 (9) | 0.7467 (17) | 0.084 (4) | |
H23A | 0.781027 | 0.888380 | 0.633457 | 0.126* | |
H23B | 0.934110 | 0.843646 | 0.773981 | 0.126* | |
H23C | 0.882885 | 0.937421 | 0.794029 | 0.126* | |
C24 | 0.5703 (16) | 0.9104 (9) | 0.7627 (16) | 0.078 (4) | |
H24A | 0.519704 | 0.921425 | 0.650623 | 0.117* | |
H24B | 0.611075 | 0.963319 | 0.819554 | 0.117* | |
H24C | 0.487803 | 0.885891 | 0.789197 | 0.117* | |
C25 | 0.8121 (18) | 0.8411 (8) | 0.9828 (13) | 0.079 (4) | |
H25A | 0.863737 | 0.895478 | 1.024963 | 0.119* | |
H25B | 0.897574 | 0.797584 | 1.013385 | 0.119* | |
H25C | 0.734835 | 0.826746 | 1.023648 | 0.119* | |
N1 | 0.0275 (13) | 0.6674 (8) | −0.4291 (11) | 0.088 (3) | |
N2 | 0.3832 (11) | 0.7164 (6) | 0.2262 (10) | 0.058 (2) | |
O1 | 0.5431 (11) | 0.8175 (5) | 0.4662 (9) | 0.072 (2) | |
H1 | 0.488 (16) | 0.799 (9) | 0.375 (7) | 0.107* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.14 (2) | 0.143 (15) | 0.113 (16) | −0.027 (15) | 0.016 (16) | −0.044 (15) |
C2 | 0.072 (8) | 0.149 (12) | 0.057 (10) | −0.021 (7) | 0.027 (8) | −0.018 (10) |
C3 | 0.27 (4) | 0.139 (16) | 0.107 (18) | −0.010 (10) | 0.05 (2) | 0.043 (13) |
C4 | 0.073 (10) | 0.182 (14) | 0.064 (8) | −0.016 (9) | 0.029 (7) | 0.005 (7) |
C1' | 0.14 (2) | 0.143 (15) | 0.113 (16) | −0.027 (15) | 0.016 (16) | −0.044 (15) |
C2' | 0.072 (8) | 0.149 (12) | 0.057 (10) | −0.021 (7) | 0.027 (8) | −0.018 (10) |
C3' | 0.27 (4) | 0.139 (16) | 0.107 (18) | −0.010 (10) | 0.05 (2) | 0.043 (13) |
C4' | 0.073 (10) | 0.182 (14) | 0.064 (8) | −0.016 (9) | 0.029 (7) | 0.005 (7) |
C5 | 0.061 (5) | 0.070 (8) | 0.044 (5) | 0.000 (5) | 0.026 (4) | −0.004 (5) |
C6 | 0.078 (7) | 0.071 (9) | 0.060 (4) | −0.011 (5) | 0.040 (5) | −0.005 (6) |
C7 | 0.068 (6) | 0.058 (8) | 0.064 (4) | −0.016 (6) | 0.031 (5) | −0.011 (6) |
C8 | 0.066 (6) | 0.036 (7) | 0.054 (4) | 0.004 (6) | 0.028 (5) | −0.005 (5) |
C9 | 0.069 (7) | 0.079 (10) | 0.070 (8) | −0.008 (7) | 0.038 (6) | 0.009 (7) |
C10 | 0.052 (6) | 0.069 (10) | 0.069 (8) | −0.019 (6) | 0.022 (6) | −0.005 (6) |
C11 | 0.077 (7) | 0.032 (7) | 0.064 (7) | 0.001 (6) | 0.033 (6) | 0.000 (6) |
C12 | 0.065 (6) | 0.036 (7) | 0.055 (6) | 0.003 (5) | 0.029 (5) | 0.001 (5) |
C13 | 0.076 (8) | 0.035 (7) | 0.076 (8) | 0.005 (6) | 0.041 (6) | 0.010 (6) |
C14 | 0.066 (7) | 0.038 (7) | 0.058 (7) | 0.014 (6) | 0.036 (6) | 0.015 (5) |
C15 | 0.066 (6) | 0.037 (6) | 0.056 (6) | −0.004 (5) | 0.030 (5) | −0.005 (4) |
C16 | 0.057 (6) | 0.040 (6) | 0.062 (6) | −0.003 (6) | 0.036 (5) | −0.001 (4) |
C17 | 0.061 (6) | 0.044 (7) | 0.048 (6) | 0.002 (6) | 0.028 (5) | 0.003 (5) |
C18 | 0.079 (8) | 0.043 (7) | 0.074 (5) | 0.002 (7) | 0.037 (6) | 0.015 (6) |
C19 | 0.100 (9) | 0.080 (12) | 0.117 (10) | −0.010 (8) | 0.062 (8) | 0.029 (8) |
C20 | 0.092 (10) | 0.062 (10) | 0.127 (11) | 0.020 (8) | 0.053 (9) | 0.033 (8) |
C21 | 0.160 (15) | 0.089 (12) | 0.069 (5) | −0.024 (11) | 0.034 (9) | 0.022 (7) |
C22 | 0.070 (7) | 0.044 (8) | 0.056 (7) | −0.011 (6) | 0.034 (6) | −0.010 (5) |
C23 | 0.093 (9) | 0.067 (10) | 0.106 (10) | −0.027 (8) | 0.057 (8) | −0.009 (7) |
C24 | 0.099 (10) | 0.041 (8) | 0.108 (9) | 0.000 (7) | 0.059 (8) | −0.004 (6) |
C25 | 0.103 (10) | 0.061 (9) | 0.069 (8) | −0.025 (8) | 0.035 (7) | −0.021 (6) |
N1 | 0.081 (5) | 0.121 (9) | 0.063 (6) | −0.019 (6) | 0.035 (5) | −0.017 (5) |
N2 | 0.065 (5) | 0.049 (6) | 0.056 (4) | −0.001 (5) | 0.024 (4) | −0.004 (5) |
O1 | 0.096 (6) | 0.046 (5) | 0.067 (5) | −0.006 (5) | 0.033 (5) | 0.008 (4) |
C1—C2 | 1.53 (2) | C11—C12 | 1.425 (14) |
C1—H1A | 0.9600 | C11—H11 | 0.9300 |
C1—H1B | 0.9600 | C12—C13 | 1.383 (15) |
C1—H1C | 0.9600 | C12—C17 | 1.416 (14) |
C2—N1 | 1.468 (15) | C13—C14 | 1.368 (12) |
C2—H2A | 0.9700 | C13—H13 | 0.9300 |
C2—H2B | 0.9700 | C14—C15 | 1.393 (15) |
C3—C4 | 1.54 (2) | C14—C18 | 1.545 (16) |
C3—H3A | 0.9600 | C15—C16 | 1.411 (15) |
C3—H3B | 0.9600 | C15—H15 | 0.9300 |
C3—H3C | 0.9600 | C16—C17 | 1.377 (12) |
C4—N1 | 1.458 (16) | C16—C22 | 1.557 (14) |
C4—H4A | 0.9700 | C17—O1 | 1.372 (12) |
C4—H4B | 0.9700 | C18—C21 | 1.493 (17) |
C1'—C2' | 1.55 (2) | C18—C19 | 1.518 (17) |
C1'—H1'1 | 0.9600 | C18—C20 | 1.534 (18) |
C1'—H1'2 | 0.9600 | C19—H19A | 0.9600 |
C1'—H1'3 | 0.9600 | C19—H19B | 0.9600 |
C2'—N1 | 1.44 (2) | C19—H19C | 0.9600 |
C2'—H2'1 | 0.9700 | C20—H20A | 0.9600 |
C2'—H2'2 | 0.9700 | C20—H20B | 0.9600 |
C3'—C4' | 1.55 (2) | C20—H20C | 0.9600 |
C3'—H3'1 | 0.9600 | C21—H21A | 0.9600 |
C4'—N1 | 1.44 (2) | C21—H21B | 0.9600 |
C4'—H4'1 | 0.9700 | C21—H21C | 0.9600 |
C4'—H4'2 | 0.9700 | C22—C25 | 1.464 (14) |
C5—N1 | 1.346 (12) | C22—C23 | 1.553 (16) |
C5—C10 | 1.394 (16) | C22—C24 | 1.569 (17) |
C5—C6 | 1.404 (17) | C23—H23A | 0.9600 |
C6—C7 | 1.359 (14) | C23—H23B | 0.9600 |
C6—H6 | 0.9300 | C23—H23C | 0.9600 |
C7—C8 | 1.389 (15) | C24—H24A | 0.9600 |
C7—H7 | 0.9300 | C24—H24B | 0.9600 |
C8—C9 | 1.375 (15) | C24—H24C | 0.9600 |
C8—N2 | 1.382 (12) | C25—H25A | 0.9600 |
C9—C10 | 1.363 (15) | C25—H25B | 0.9600 |
C9—H9 | 0.9300 | C25—H25C | 0.9600 |
C10—H10 | 0.9300 | O1—H1 | 0.83 (2) |
C11—N2 | 1.273 (12) | ||
C2—C1—H1A | 109.5 | C12—C13—H13 | 118.1 |
C2—C1—H1B | 109.5 | C13—C14—C15 | 117.2 (9) |
H1A—C1—H1B | 109.5 | C13—C14—C18 | 121.9 (10) |
C2—C1—H1C | 109.5 | C15—C14—C18 | 120.9 (9) |
H1A—C1—H1C | 109.5 | C14—C15—C16 | 121.9 (9) |
H1B—C1—H1C | 109.5 | C14—C15—H15 | 119.1 |
N1—C2—C1 | 110.7 (15) | C16—C15—H15 | 119.1 |
N1—C2—H2A | 109.5 | C17—C16—C15 | 118.5 (9) |
C1—C2—H2A | 109.5 | C17—C16—C22 | 122.7 (8) |
N1—C2—H2B | 109.5 | C15—C16—C22 | 118.8 (8) |
C1—C2—H2B | 109.5 | O1—C17—C16 | 120.9 (9) |
H2A—C2—H2B | 108.1 | O1—C17—C12 | 118.2 (8) |
C4—C3—H3A | 109.5 | C16—C17—C12 | 120.9 (9) |
C4—C3—H3B | 109.5 | C21—C18—C19 | 109.9 (11) |
H3A—C3—H3B | 109.5 | C21—C18—C20 | 110.1 (11) |
C4—C3—H3C | 109.5 | C19—C18—C20 | 106.5 (11) |
H3A—C3—H3C | 109.5 | C21—C18—C14 | 113.0 (11) |
H3B—C3—H3C | 109.5 | C19—C18—C14 | 109.7 (9) |
N1—C4—C3 | 106.6 (19) | C20—C18—C14 | 107.4 (10) |
N1—C4—H4A | 110.4 | C18—C19—H19A | 109.5 |
C3—C4—H4A | 110.4 | C18—C19—H19B | 109.5 |
N1—C4—H4B | 110.4 | H19A—C19—H19B | 109.5 |
C3—C4—H4B | 110.4 | C18—C19—H19C | 109.5 |
H4A—C4—H4B | 108.6 | H19A—C19—H19C | 109.5 |
C2'—C1'—H1'1 | 109.5 | H19B—C19—H19C | 109.5 |
C2'—C1'—H1'2 | 109.5 | C18—C20—H20A | 109.5 |
H1'1—C1'—H1'2 | 109.5 | C18—C20—H20B | 109.5 |
C2'—C1'—H1'3 | 109.5 | H20A—C20—H20B | 109.5 |
H1'1—C1'—H1'3 | 109.5 | C18—C20—H20C | 109.5 |
H1'2—C1'—H1'3 | 109.5 | H20A—C20—H20C | 109.5 |
N1—C2'—C1' | 105 (8) | H20B—C20—H20C | 109.5 |
N1—C2'—H2'1 | 110.6 | C18—C21—H21A | 109.5 |
C1'—C2'—H2'1 | 110.6 | C18—C21—H21B | 109.5 |
N1—C2'—H2'2 | 110.6 | H21A—C21—H21B | 109.5 |
C1'—C2'—H2'2 | 110.6 | C18—C21—H21C | 109.5 |
H2'1—C2'—H2'2 | 108.8 | H21A—C21—H21C | 109.5 |
C4'—C3'—H3'1 | 109.5 | H21B—C21—H21C | 109.5 |
C4'—C3'—H3'3 | 109.5 | C25—C22—C23 | 108.9 (10) |
H3'2—C3'—H3'3 | 109.5 | C25—C22—C16 | 113.8 (9) |
N1—C4'—C3' | 120 (9) | C23—C22—C16 | 109.7 (8) |
N1—C4'—H4'1 | 107.3 | C25—C22—C24 | 108.4 (10) |
N1—C4'—H4'2 | 107.3 | C23—C22—C24 | 108.3 (9) |
C3'—C4'—H4'2 | 107.3 | C16—C22—C24 | 107.6 (9) |
H4'1—C4'—H4'2 | 106.9 | C22—C23—H23A | 109.5 |
N1—C5—C10 | 122.8 (11) | C22—C23—H23B | 109.5 |
N1—C5—C6 | 121.8 (10) | H23A—C23—H23B | 109.5 |
C10—C5—C6 | 115.2 (9) | C22—C23—H23C | 109.5 |
C7—C6—C5 | 120.8 (11) | H23A—C23—H23C | 109.5 |
C7—C6—H6 | 119.6 | H23B—C23—H23C | 109.5 |
C5—C6—H6 | 119.6 | C22—C24—H24A | 109.5 |
C6—C7—C8 | 124.1 (11) | C22—C24—H24B | 109.5 |
C6—C7—H7 | 117.9 | H24A—C24—H24B | 109.5 |
C8—C7—H7 | 117.9 | C22—C24—H24C | 109.5 |
C9—C8—N2 | 125.8 (9) | H24A—C24—H24C | 109.5 |
C9—C8—C7 | 114.6 (9) | H24B—C24—H24C | 109.5 |
N2—C8—C7 | 119.6 (10) | C22—C25—H25A | 109.5 |
C10—C9—C8 | 122.8 (10) | C22—C25—H25B | 109.5 |
C10—C9—H9 | 118.6 | H25A—C25—H25B | 109.5 |
C8—C9—H9 | 118.6 | C22—C25—H25C | 109.5 |
C9—C10—C5 | 122.5 (11) | H25A—C25—H25C | 109.5 |
C9—C10—H10 | 118.8 | H25B—C25—H25C | 109.5 |
C5—C10—H10 | 118.8 | C5—N1—C4' | 131 (5) |
N2—C11—C12 | 124.6 (10) | C5—N1—C2' | 99 (4) |
N2—C11—H11 | 117.7 | C4'—N1—C2' | 117 (7) |
C12—C11—H11 | 117.7 | C5—N1—C4 | 122.6 (11) |
C13—C12—C17 | 117.6 (9) | C5—N1—C2 | 123.4 (11) |
C13—C12—C11 | 120.3 (10) | C4—N1—C2 | 114.0 (11) |
C17—C12—C11 | 122.0 (9) | C11—N2—C8 | 121.3 (9) |
C14—C13—C12 | 123.8 (11) | C17—O1—H1 | 106 (10) |
C14—C13—H13 | 118.1 | ||
N1—C5—C6—C7 | 178.4 (11) | C13—C14—C18—C19 | −49.8 (15) |
C10—C5—C6—C7 | 2.6 (18) | C15—C14—C18—C19 | 129.6 (12) |
C5—C6—C7—C8 | −0.8 (18) | C13—C14—C18—C20 | 65.5 (13) |
C6—C7—C8—C9 | −1.6 (17) | C15—C14—C18—C20 | −115.1 (12) |
C6—C7—C8—N2 | −179.8 (11) | C17—C16—C22—C25 | −178.0 (10) |
N2—C8—C9—C10 | −179.9 (11) | C15—C16—C22—C25 | 3.9 (15) |
C7—C8—C9—C10 | 2.1 (17) | C17—C16—C22—C23 | −55.7 (13) |
C8—C9—C10—C5 | −0.2 (19) | C15—C16—C22—C23 | 126.1 (11) |
N1—C5—C10—C9 | −177.9 (13) | C17—C16—C22—C24 | 61.9 (12) |
C6—C5—C10—C9 | −2.2 (18) | C15—C16—C22—C24 | −116.2 (10) |
N2—C11—C12—C13 | −178.5 (11) | C10—C5—N1—C4' | 146 (7) |
N2—C11—C12—C17 | 4.3 (17) | C6—C5—N1—C4' | −29 (7) |
C17—C12—C13—C14 | −3.1 (17) | C10—C5—N1—C2' | 8 (6) |
C11—C12—C13—C14 | 179.6 (11) | C6—C5—N1—C2' | −167 (6) |
C12—C13—C14—C15 | 2.1 (16) | C10—C5—N1—C4 | −177.2 (16) |
C12—C13—C14—C18 | −178.4 (11) | C6—C5—N1—C4 | 7 (2) |
C13—C14—C15—C16 | −0.4 (17) | C10—C5—N1—C2 | 0 (2) |
C18—C14—C15—C16 | −179.8 (10) | C6—C5—N1—C2 | −175.3 (15) |
C14—C15—C16—C17 | −0.2 (16) | C3'—C4'—N1—C5 | 2 (19) |
C14—C15—C16—C22 | 178.0 (9) | C3'—C4'—N1—C2' | 134 (15) |
C15—C16—C17—O1 | −179.0 (9) | C1'—C2'—N1—C5 | −149 (10) |
C22—C16—C17—O1 | 2.9 (14) | C1'—C2'—N1—C4' | 65 (13) |
C15—C16—C17—C12 | −0.8 (14) | C3—C4—N1—C5 | −95 (2) |
C22—C16—C17—C12 | −178.9 (9) | C3—C4—N1—C2 | 87.3 (19) |
C13—C12—C17—O1 | −179.4 (10) | C1—C2—N1—C5 | −82 (2) |
C11—C12—C17—O1 | −2.1 (15) | C1—C2—N1—C4 | 96 (2) |
C13—C12—C17—C16 | 2.3 (15) | C12—C11—N2—C8 | −178.7 (10) |
C11—C12—C17—C16 | 179.6 (10) | C9—C8—N2—C11 | 33.1 (16) |
C13—C14—C18—C21 | −172.9 (12) | C7—C8—N2—C11 | −149.0 (11) |
C15—C14—C18—C21 | 6.5 (16) |
Cg2 is the centroid of the C12–C17 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2 | 0.83 (7) | 1.82 (11) | 2.591 (12) | 155 (14) |
C23—H23A···O1 | 0.96 | 2.27 | 2.947 (17) | 127 |
C24—H24A···O1 | 0.96 | 2.46 | 3.071 (16) | 121 |
C2—H2B···Cg2i | 0.97 | 2.87 | 3.810 (19) | 166 |
C2′—H2′1···Cg2i | 0.97 | 2.60 | 3.39 (11) | 139 |
Symmetry code: (i) x−1, y, z−1. |
Acknowledgements
The authors acknowledge the SAIF, IIT, Madras, for the data collection.
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