organic compounds
2,5-Dimethylanilinium 4-hydroxybenzoate–2,5-dimethylaniline–4-hydroxybenzoic acid (1/1/1)
aDepartment of Physics, Sri Venkateswaraa College of Technology, Sriperumbudur 602 105, India, bDepartment of Physics, Presidency College, Chennai 600 005, India, cDepartment of Physics, AMET University, Chennai 603 112, India, and dDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India
*Correspondence e-mail: ppkpresidency@gmail.com, chakkaravarthi_2005@yahoo.com
The 8H12N+·C7H5O3−·C8H11N·C7H6O3, contains a 2,5-dimethylanilinium cation, 4-hydroxybenzoate anion and neutral 2,5-dimethylaniline and 4-hydroxybenzoic acid molecules. The components are connected by N—H⋯O, O—H⋯O and N—H⋯N hydrogen bonds, which generate R22(8), R44(20) and R44(24) loops, as part of a three-dimensional network. The also features weak C—H⋯π interactions.
of the title compound, CKeywords: crystal structure; hydrogen bonding,.
CCDC reference: 1509213
Structure description
We report the synthesis and structure of the title compound which comprises a 2,5-dimethylanilinium cation, a 4-hydroxybenzoate anion and neutral 2,5-dimethylaniline and 4-hydroxybenzoic acid molecules (Fig. 1). The benzene rings of the cation (C1–C6) and anion (C17–C22) are inclined at an angle of 15.00 (9) Å while the benzene rings of the neutral molecules (C9–C14) and (C24–C29) are inclined at an angle of 11.08 (9) Å. The bond lengths of the ions and molecules are comparable with those in previously reported structures (Fun et al., 2011; Mani et al., 2015; Mathlouthi et al., 2014).
In the arbitrarily chosen B⋯O2 hydrogen bond and the ions are connected to the 4-hydroxybenzoic acid molecule through N1—H1A⋯O5 and O4—H4A⋯O2 hydrogen bonds, forming an (8) loop. Further, the 2,5-dimethylanilinium cation and 2,5-dimethylaniline molecule are connected through an N1—H1A⋯N2 hydrogen bond (Table 1 and Fig. 2).
the anion and cation are connected by an N1—H1In the extended structure, pairs of O—H⋯O [(O3—H3A⋯O6iv and O6—H6A⋯O1iii) and (O6—H6A⋯O1iii and O4—H4A⋯O2); for symmetry codes, see Table 1] hydrogen bonds generate (20) and (24) ring-motifs, respectively (Fig. 3), which generate a three-dimensional network (Fig. 4). The also features weak C—H⋯π interactions.
Synthesis and crystallization
A mixture of 2,5-xylidine and 4-hydroxybenzoic acid dissolved in ethanol (molar ratio 1:1:1) was stirred for 4 h and then kept at room temperature. After three weeks, colourless blocks were obtained.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
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Structural data
CCDC reference: 1509213
https://doi.org/10.1107/S2414314616016072/hb4085sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616016072/hb4085Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314616016072/hb4085Isup3.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: SHELXL2016/4 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2016/4 (Sheldrick, 2015) and PLATON (Spek, 2009).C8H12N+·C7H5O3−·C8H11N·C7H6O3 | Z = 2 |
Mr = 518.59 | F(000) = 552 |
Triclinic, P1 | Dx = 1.304 Mg m−3 |
a = 9.6854 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.9169 (6) Å | Cell parameters from 6719 reflections |
c = 13.1450 (7) Å | θ = 2.3–29.4° |
α = 79.029 (4)° | µ = 0.09 mm−1 |
β = 75.615 (3)° | T = 295 K |
γ = 85.345 (4)° | Block, colourless |
V = 1320.86 (13) Å3 | 0.26 × 0.24 × 0.20 mm |
Bruker Kappa APEXII CCD diffractometer | 4026 reflections with I > 2σ(I) |
ω and φ scan | Rint = 0.070 |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | θmax = 29.5°, θmin = 2.2° |
Tmin = 0.688, Tmax = 0.746 | h = −13→13 |
35698 measured reflections | k = −15→15 |
7024 independent reflections | l = −18→18 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.059 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.145 | w = 1/[σ2(Fo2) + (0.0575P)2 + 0.3498P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
7024 reflections | Δρmax = 0.26 e Å−3 |
376 parameters | Δρmin = −0.30 e Å−3 |
8 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.86255 (19) | 0.17699 (16) | 0.55783 (14) | 0.0292 (4) | |
C2 | 0.72606 (19) | 0.22707 (16) | 0.59077 (14) | 0.0277 (4) | |
C3 | 0.6211 (2) | 0.16170 (17) | 0.66719 (14) | 0.0323 (4) | |
H3 | 0.529843 | 0.197520 | 0.685334 | 0.039* | |
C4 | 0.6513 (2) | 0.04190 (18) | 0.71738 (15) | 0.0377 (5) | |
C5 | 0.7887 (2) | −0.00660 (18) | 0.68915 (16) | 0.0406 (5) | |
H5 | 0.812282 | −0.085084 | 0.723802 | 0.049* | |
C6 | 0.8915 (2) | 0.05903 (17) | 0.61069 (15) | 0.0358 (4) | |
H6 | 0.982781 | 0.023265 | 0.592701 | 0.043* | |
C7 | 0.9738 (2) | 0.24619 (19) | 0.46942 (16) | 0.0400 (5) | |
H7A | 1.060098 | 0.195534 | 0.457843 | 0.060* | |
H7B | 0.992273 | 0.322696 | 0.488735 | 0.060* | |
H7C | 0.940066 | 0.264569 | 0.405190 | 0.060* | |
C8 | 0.5368 (3) | −0.0305 (2) | 0.8010 (2) | 0.0635 (7) | |
H8A | 0.503145 | −0.092472 | 0.771013 | 0.095* | |
H8B | 0.459104 | 0.025493 | 0.825236 | 0.095* | |
H8C | 0.575279 | −0.070556 | 0.860116 | 0.095* | |
C9 | 0.7449 (2) | 0.49451 (19) | 0.82967 (18) | 0.0437 (5) | |
C10 | 0.6808 (2) | 0.4508 (2) | 0.93580 (18) | 0.0498 (6) | |
H10 | 0.632124 | 0.507313 | 0.978034 | 0.060* | |
C11 | 0.6869 (2) | 0.3264 (2) | 0.98062 (17) | 0.0492 (6) | |
H11 | 0.643147 | 0.300354 | 1.052185 | 0.059* | |
C12 | 0.7577 (2) | 0.24010 (19) | 0.91973 (16) | 0.0405 (5) | |
C13 | 0.8226 (2) | 0.28259 (18) | 0.81374 (15) | 0.0360 (4) | |
H13 | 0.869464 | 0.225492 | 0.771407 | 0.043* | |
C14 | 0.8192 (2) | 0.40806 (18) | 0.76934 (15) | 0.0355 (5) | |
C15 | 0.7351 (3) | 0.6308 (2) | 0.7828 (2) | 0.0734 (8) | |
H15A | 0.672759 | 0.674199 | 0.834325 | 0.110* | |
H15B | 0.698040 | 0.640291 | 0.720302 | 0.110* | |
H15C | 0.828262 | 0.664817 | 0.763670 | 0.110* | |
C16 | 0.7672 (3) | 0.1037 (2) | 0.9659 (2) | 0.0704 (8) | |
H16A | 0.854196 | 0.085435 | 0.989195 | 0.106* | |
H16B | 0.765939 | 0.055034 | 0.912536 | 0.106* | |
H16C | 0.687379 | 0.083353 | 1.025583 | 0.106* | |
C17 | 0.29119 (19) | 0.44302 (15) | 0.80120 (13) | 0.0267 (4) | |
C18 | 0.1466 (2) | 0.45138 (17) | 0.84845 (15) | 0.0332 (4) | |
H18 | 0.089970 | 0.513913 | 0.818656 | 0.040* | |
C19 | 0.0851 (2) | 0.36894 (17) | 0.93867 (15) | 0.0356 (5) | |
H19 | −0.012149 | 0.375521 | 0.968950 | 0.043* | |
C20 | 0.1690 (2) | 0.27650 (17) | 0.98379 (15) | 0.0365 (5) | |
C21 | 0.3135 (2) | 0.26666 (17) | 0.93802 (15) | 0.0398 (5) | |
H21 | 0.369889 | 0.204221 | 0.968234 | 0.048* | |
C22 | 0.3739 (2) | 0.34920 (16) | 0.84780 (14) | 0.0324 (4) | |
H22 | 0.471145 | 0.342192 | 0.817592 | 0.039* | |
C23 | 0.3543 (2) | 0.53064 (16) | 0.70188 (14) | 0.0293 (4) | |
C24 | 0.73147 (18) | 0.84066 (16) | 0.39196 (14) | 0.0283 (4) | |
C25 | 0.82153 (19) | 0.85457 (17) | 0.29055 (15) | 0.0321 (4) | |
H25 | 0.858731 | 0.784245 | 0.261371 | 0.039* | |
C26 | 0.8563 (2) | 0.97198 (17) | 0.23265 (15) | 0.0348 (4) | |
H26 | 0.916804 | 0.980486 | 0.164794 | 0.042* | |
C27 | 0.80129 (19) | 1.07684 (16) | 0.27555 (14) | 0.0303 (4) | |
C28 | 0.70977 (19) | 1.06454 (16) | 0.37624 (15) | 0.0321 (4) | |
H28 | 0.671854 | 1.135002 | 0.404962 | 0.039* | |
C29 | 0.67551 (19) | 0.94683 (17) | 0.43341 (15) | 0.0326 (4) | |
H29 | 0.613906 | 0.938508 | 0.500819 | 0.039* | |
C30 | 0.6966 (2) | 0.71342 (17) | 0.45436 (15) | 0.0319 (4) | |
N1 | 0.69424 (19) | 0.35629 (15) | 0.54491 (14) | 0.0348 (4) | |
N2 | 0.8895 (2) | 0.44564 (19) | 0.66002 (15) | 0.0488 (5) | |
O1 | 0.28132 (14) | 0.62590 (11) | 0.67266 (10) | 0.0380 (3) | |
O2 | 0.47869 (14) | 0.50631 (11) | 0.64920 (10) | 0.0391 (3) | |
O3 | 0.11541 (18) | 0.19274 (14) | 1.07406 (13) | 0.0578 (5) | |
O4 | 0.57699 (16) | 0.71376 (13) | 0.52863 (13) | 0.0515 (4) | |
O5 | 0.77000 (15) | 0.62033 (12) | 0.43902 (12) | 0.0455 (4) | |
O6 | 0.83921 (16) | 1.19187 (12) | 0.21635 (11) | 0.0446 (4) | |
H1A | 0.755 (2) | 0.4040 (18) | 0.5552 (18) | 0.057 (7)* | |
H1B | 0.6106 (14) | 0.379 (2) | 0.5801 (16) | 0.052 (7)* | |
H1C | 0.698 (3) | 0.363 (2) | 0.4768 (9) | 0.063 (8)* | |
H2A | 0.898 (3) | 0.5244 (10) | 0.643 (2) | 0.080 (9)* | |
H2B | 0.9714 (16) | 0.409 (2) | 0.644 (2) | 0.077 (10)* | |
H3A | 0.0300 (14) | 0.206 (3) | 1.099 (3) | 0.116* | |
H4A | 0.555 (3) | 0.6430 (15) | 0.564 (2) | 0.116* | |
H6A | 0.798 (3) | 1.248 (2) | 0.248 (2) | 0.116* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0304 (10) | 0.0291 (9) | 0.0274 (9) | −0.0006 (8) | −0.0047 (7) | −0.0066 (7) |
C2 | 0.0305 (10) | 0.0246 (9) | 0.0270 (9) | 0.0016 (7) | −0.0079 (7) | −0.0017 (7) |
C3 | 0.0280 (10) | 0.0344 (10) | 0.0321 (10) | 0.0014 (8) | −0.0061 (8) | −0.0024 (8) |
C4 | 0.0402 (12) | 0.0352 (10) | 0.0346 (11) | −0.0067 (9) | −0.0087 (9) | 0.0033 (8) |
C5 | 0.0507 (13) | 0.0272 (10) | 0.0431 (12) | 0.0037 (9) | −0.0168 (10) | 0.0016 (8) |
C6 | 0.0351 (11) | 0.0340 (10) | 0.0386 (11) | 0.0106 (8) | −0.0108 (9) | −0.0094 (8) |
C7 | 0.0324 (11) | 0.0423 (11) | 0.0404 (11) | −0.0010 (9) | −0.0002 (9) | −0.0066 (9) |
C8 | 0.0565 (16) | 0.0587 (15) | 0.0611 (16) | −0.0163 (12) | −0.0068 (12) | 0.0209 (12) |
C9 | 0.0435 (13) | 0.0386 (11) | 0.0511 (13) | 0.0002 (9) | −0.0115 (10) | −0.0137 (10) |
C10 | 0.0416 (13) | 0.0555 (14) | 0.0532 (14) | 0.0027 (11) | −0.0014 (10) | −0.0263 (12) |
C11 | 0.0422 (13) | 0.0647 (15) | 0.0369 (12) | −0.0092 (11) | 0.0037 (9) | −0.0137 (11) |
C12 | 0.0399 (12) | 0.0432 (11) | 0.0370 (11) | −0.0069 (9) | −0.0063 (9) | −0.0054 (9) |
C13 | 0.0364 (11) | 0.0356 (10) | 0.0353 (11) | −0.0017 (9) | −0.0044 (8) | −0.0099 (8) |
C14 | 0.0334 (11) | 0.0396 (11) | 0.0343 (10) | −0.0070 (9) | −0.0060 (8) | −0.0089 (9) |
C15 | 0.099 (2) | 0.0411 (14) | 0.078 (2) | 0.0072 (14) | −0.0171 (17) | −0.0165 (13) |
C16 | 0.096 (2) | 0.0541 (15) | 0.0500 (15) | −0.0076 (14) | −0.0086 (14) | 0.0071 (12) |
C17 | 0.0291 (10) | 0.0227 (8) | 0.0254 (9) | −0.0010 (7) | −0.0025 (7) | −0.0021 (7) |
C18 | 0.0308 (10) | 0.0305 (9) | 0.0348 (10) | 0.0013 (8) | −0.0058 (8) | −0.0007 (8) |
C19 | 0.0267 (10) | 0.0370 (10) | 0.0372 (11) | −0.0046 (8) | 0.0034 (8) | −0.0053 (8) |
C20 | 0.0438 (12) | 0.0292 (10) | 0.0300 (10) | −0.0079 (9) | 0.0010 (8) | 0.0011 (8) |
C21 | 0.0426 (12) | 0.0315 (10) | 0.0363 (11) | 0.0069 (9) | −0.0038 (9) | 0.0055 (8) |
C22 | 0.0284 (10) | 0.0324 (10) | 0.0312 (10) | 0.0037 (8) | −0.0015 (8) | −0.0025 (8) |
C23 | 0.0328 (10) | 0.0235 (9) | 0.0287 (9) | −0.0025 (8) | −0.0032 (8) | −0.0021 (7) |
C24 | 0.0236 (9) | 0.0265 (9) | 0.0325 (10) | −0.0014 (7) | −0.0054 (7) | −0.0009 (7) |
C25 | 0.0303 (10) | 0.0279 (9) | 0.0356 (10) | 0.0022 (8) | −0.0031 (8) | −0.0073 (8) |
C26 | 0.0350 (11) | 0.0338 (10) | 0.0288 (10) | 0.0009 (8) | 0.0025 (8) | −0.0030 (8) |
C27 | 0.0266 (10) | 0.0280 (9) | 0.0314 (10) | −0.0020 (7) | −0.0036 (7) | 0.0027 (7) |
C28 | 0.0320 (10) | 0.0257 (9) | 0.0356 (10) | 0.0019 (8) | −0.0025 (8) | −0.0064 (8) |
C29 | 0.0284 (10) | 0.0326 (10) | 0.0311 (10) | 0.0001 (8) | 0.0004 (8) | −0.0018 (8) |
C30 | 0.0288 (10) | 0.0296 (10) | 0.0363 (10) | −0.0041 (8) | −0.0084 (8) | −0.0011 (8) |
N1 | 0.0363 (10) | 0.0284 (9) | 0.0343 (10) | 0.0036 (8) | −0.0029 (8) | −0.0013 (7) |
N2 | 0.0612 (14) | 0.0395 (11) | 0.0398 (11) | −0.0093 (10) | −0.0009 (9) | −0.0037 (9) |
O1 | 0.0447 (8) | 0.0263 (7) | 0.0345 (7) | 0.0083 (6) | −0.0022 (6) | 0.0023 (5) |
O2 | 0.0354 (8) | 0.0313 (7) | 0.0373 (8) | 0.0019 (6) | 0.0073 (6) | 0.0044 (6) |
O3 | 0.0618 (11) | 0.0443 (9) | 0.0462 (9) | −0.0062 (8) | 0.0100 (8) | 0.0156 (7) |
O4 | 0.0413 (9) | 0.0330 (8) | 0.0599 (10) | −0.0007 (7) | 0.0115 (7) | 0.0101 (7) |
O5 | 0.0466 (9) | 0.0274 (7) | 0.0550 (9) | 0.0009 (6) | −0.0031 (7) | −0.0017 (6) |
O6 | 0.0520 (9) | 0.0282 (7) | 0.0404 (8) | −0.0031 (7) | 0.0064 (7) | 0.0036 (6) |
C1—C6 | 1.385 (2) | C17—C18 | 1.387 (2) |
C1—C2 | 1.386 (3) | C17—C22 | 1.392 (2) |
C1—C7 | 1.503 (2) | C17—C23 | 1.489 (2) |
C2—C3 | 1.375 (2) | C18—C19 | 1.379 (2) |
C2—N1 | 1.465 (2) | C18—H18 | 0.9300 |
C3—C4 | 1.392 (3) | C19—C20 | 1.381 (3) |
C3—H3 | 0.9300 | C19—H19 | 0.9300 |
C4—C5 | 1.380 (3) | C20—O3 | 1.368 (2) |
C4—C8 | 1.506 (3) | C20—C21 | 1.384 (3) |
C5—C6 | 1.376 (3) | C21—C22 | 1.376 (2) |
C5—H5 | 0.9300 | C21—H21 | 0.9300 |
C6—H6 | 0.9300 | C22—H22 | 0.9300 |
C7—H7A | 0.9600 | C23—O1 | 1.262 (2) |
C7—H7B | 0.9600 | C23—O2 | 1.267 (2) |
C7—H7C | 0.9600 | C24—C29 | 1.388 (2) |
C8—H8A | 0.9600 | C24—C25 | 1.388 (2) |
C8—H8B | 0.9600 | C24—C30 | 1.490 (2) |
C8—H8C | 0.9600 | C25—C26 | 1.381 (2) |
C9—C10 | 1.387 (3) | C25—H25 | 0.9300 |
C9—C14 | 1.389 (3) | C26—C27 | 1.382 (3) |
C9—C15 | 1.503 (3) | C26—H26 | 0.9300 |
C10—C11 | 1.376 (3) | C27—O6 | 1.371 (2) |
C10—H10 | 0.9300 | C27—C28 | 1.387 (2) |
C11—C12 | 1.381 (3) | C28—C29 | 1.380 (2) |
C11—H11 | 0.9300 | C28—H28 | 0.9300 |
C12—C13 | 1.385 (3) | C29—H29 | 0.9300 |
C12—C16 | 1.502 (3) | C30—O5 | 1.212 (2) |
C13—C14 | 1.384 (3) | C30—O4 | 1.317 (2) |
C13—H13 | 0.9300 | N1—H1A | 0.869 (9) |
C14—N2 | 1.425 (3) | N1—H1B | 0.871 (9) |
C15—H15A | 0.9600 | N1—H1C | 0.876 (10) |
C15—H15B | 0.9600 | N2—H2A | 0.852 (10) |
C15—H15C | 0.9600 | N2—H2B | 0.856 (10) |
C16—H16A | 0.9600 | O3—H3A | 0.824 (10) |
C16—H16B | 0.9600 | O4—H4A | 0.834 (10) |
C16—H16C | 0.9600 | O6—H6A | 0.830 (10) |
C6—C1—C2 | 116.45 (16) | C12—C16—H16C | 109.5 |
C6—C1—C7 | 121.39 (17) | H16A—C16—H16C | 109.5 |
C2—C1—C7 | 122.15 (16) | H16B—C16—H16C | 109.5 |
C3—C2—C1 | 122.61 (16) | C18—C17—C22 | 118.19 (16) |
C3—C2—N1 | 118.80 (17) | C18—C17—C23 | 120.40 (16) |
C1—C2—N1 | 118.55 (16) | C22—C17—C23 | 121.39 (16) |
C2—C3—C4 | 119.97 (18) | C19—C18—C17 | 121.40 (17) |
C2—C3—H3 | 120.0 | C19—C18—H18 | 119.3 |
C4—C3—H3 | 120.0 | C17—C18—H18 | 119.3 |
C5—C4—C3 | 117.97 (17) | C18—C19—C20 | 119.55 (17) |
C5—C4—C8 | 121.70 (19) | C18—C19—H19 | 120.2 |
C3—C4—C8 | 120.3 (2) | C20—C19—H19 | 120.2 |
C6—C5—C4 | 121.20 (17) | O3—C20—C19 | 122.63 (18) |
C6—C5—H5 | 119.4 | O3—C20—C21 | 117.39 (18) |
C4—C5—H5 | 119.4 | C19—C20—C21 | 119.98 (16) |
C5—C6—C1 | 121.67 (18) | C22—C21—C20 | 120.05 (18) |
C5—C6—H6 | 119.2 | C22—C21—H21 | 120.0 |
C1—C6—H6 | 119.2 | C20—C21—H21 | 120.0 |
C1—C7—H7A | 109.5 | C21—C22—C17 | 120.83 (17) |
C1—C7—H7B | 109.5 | C21—C22—H22 | 119.6 |
H7A—C7—H7B | 109.5 | C17—C22—H22 | 119.6 |
C1—C7—H7C | 109.5 | O1—C23—O2 | 122.37 (16) |
H7A—C7—H7C | 109.5 | O1—C23—C17 | 118.75 (16) |
H7B—C7—H7C | 109.5 | O2—C23—C17 | 118.87 (16) |
C4—C8—H8A | 109.5 | C29—C24—C25 | 118.81 (16) |
C4—C8—H8B | 109.5 | C29—C24—C30 | 121.15 (16) |
H8A—C8—H8B | 109.5 | C25—C24—C30 | 120.04 (16) |
C4—C8—H8C | 109.5 | C26—C25—C24 | 120.55 (17) |
H8A—C8—H8C | 109.5 | C26—C25—H25 | 119.7 |
H8B—C8—H8C | 109.5 | C24—C25—H25 | 119.7 |
C10—C9—C14 | 117.50 (19) | C25—C26—C27 | 119.99 (17) |
C10—C9—C15 | 120.9 (2) | C25—C26—H26 | 120.0 |
C14—C9—C15 | 121.6 (2) | C27—C26—H26 | 120.0 |
C11—C10—C9 | 122.1 (2) | O6—C27—C26 | 118.45 (16) |
C11—C10—H10 | 118.9 | O6—C27—C28 | 121.39 (16) |
C9—C10—H10 | 118.9 | C26—C27—C28 | 120.16 (16) |
C10—C11—C12 | 120.2 (2) | C29—C28—C27 | 119.41 (17) |
C10—C11—H11 | 119.9 | C29—C28—H28 | 120.3 |
C12—C11—H11 | 119.9 | C27—C28—H28 | 120.3 |
C11—C12—C13 | 118.20 (19) | C28—C29—C24 | 121.08 (17) |
C11—C12—C16 | 121.8 (2) | C28—C29—H29 | 119.5 |
C13—C12—C16 | 120.0 (2) | C24—C29—H29 | 119.5 |
C14—C13—C12 | 121.52 (19) | O5—C30—O4 | 123.77 (16) |
C14—C13—H13 | 119.2 | O5—C30—C24 | 124.02 (17) |
C12—C13—H13 | 119.2 | O4—C30—C24 | 112.21 (16) |
C13—C14—C9 | 120.33 (18) | C2—N1—H1A | 108.4 (16) |
C13—C14—N2 | 118.65 (18) | C2—N1—H1B | 108.7 (15) |
C9—C14—N2 | 120.99 (19) | H1A—N1—H1B | 106 (2) |
C9—C15—H15A | 109.5 | C2—N1—H1C | 110.5 (16) |
C9—C15—H15B | 109.5 | H1A—N1—H1C | 111 (2) |
H15A—C15—H15B | 109.5 | H1B—N1—H1C | 111 (2) |
C9—C15—H15C | 109.5 | C14—N2—H2A | 112.1 (19) |
H15A—C15—H15C | 109.5 | C14—N2—H2B | 112.1 (19) |
H15B—C15—H15C | 109.5 | H2A—N2—H2B | 109 (3) |
C12—C16—H16A | 109.5 | C20—O3—H3A | 113 (2) |
C12—C16—H16B | 109.5 | C30—O4—H4A | 113 (2) |
H16A—C16—H16B | 109.5 | C27—O6—H6A | 111 (2) |
C6—C1—C2—C3 | −3.8 (3) | C23—C17—C18—C19 | 178.08 (17) |
C7—C1—C2—C3 | 176.07 (18) | C17—C18—C19—C20 | 0.5 (3) |
C6—C1—C2—N1 | 173.96 (17) | C18—C19—C20—O3 | 179.08 (19) |
C7—C1—C2—N1 | −6.1 (3) | C18—C19—C20—C21 | −0.4 (3) |
C1—C2—C3—C4 | 2.3 (3) | O3—C20—C21—C22 | −179.26 (18) |
N1—C2—C3—C4 | −175.54 (18) | C19—C20—C21—C22 | 0.3 (3) |
C2—C3—C4—C5 | 1.1 (3) | C20—C21—C22—C17 | −0.2 (3) |
C2—C3—C4—C8 | −179.88 (19) | C18—C17—C22—C21 | 0.3 (3) |
C3—C4—C5—C6 | −2.7 (3) | C23—C17—C22—C21 | −178.23 (17) |
C8—C4—C5—C6 | 178.3 (2) | C18—C17—C23—O1 | 13.0 (3) |
C4—C5—C6—C1 | 1.0 (3) | C22—C17—C23—O1 | −168.48 (17) |
C2—C1—C6—C5 | 2.2 (3) | C18—C17—C23—O2 | −166.33 (17) |
C7—C1—C6—C5 | −177.70 (18) | C22—C17—C23—O2 | 12.2 (3) |
C14—C9—C10—C11 | −1.3 (3) | C29—C24—C25—C26 | 0.9 (3) |
C15—C9—C10—C11 | 179.4 (2) | C30—C24—C25—C26 | −179.00 (17) |
C9—C10—C11—C12 | −0.4 (4) | C24—C25—C26—C27 | −0.1 (3) |
C10—C11—C12—C13 | 0.6 (3) | C25—C26—C27—O6 | 179.34 (17) |
C10—C11—C12—C16 | 179.7 (2) | C25—C26—C27—C28 | −0.7 (3) |
C11—C12—C13—C14 | 0.9 (3) | O6—C27—C28—C29 | −179.42 (17) |
C16—C12—C13—C14 | −178.2 (2) | C26—C27—C28—C29 | 0.7 (3) |
C12—C13—C14—C9 | −2.6 (3) | C27—C28—C29—C24 | 0.2 (3) |
C12—C13—C14—N2 | 179.36 (19) | C25—C24—C29—C28 | −1.0 (3) |
C10—C9—C14—C13 | 2.7 (3) | C30—C24—C29—C28 | 178.92 (17) |
C15—C9—C14—C13 | −177.9 (2) | C29—C24—C30—O5 | −157.41 (19) |
C10—C9—C14—N2 | −179.3 (2) | C25—C24—C30—O5 | 22.5 (3) |
C15—C9—C14—N2 | 0.1 (3) | C29—C24—C30—O4 | 22.3 (2) |
C22—C17—C18—C19 | −0.5 (3) | C25—C24—C30—O4 | −157.83 (18) |
Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C9–C14 and C24–C29 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O5 | 0.87 (1) | 2.55 (2) | 3.015 (2) | 114 (2) |
N1—H1A···N2 | 0.87 (1) | 2.24 (2) | 3.016 (3) | 149 (2) |
N1—H1B···O2 | 0.87 (1) | 2.00 (1) | 2.792 (2) | 151 (2) |
O4—H4A···O2 | 0.83 (1) | 1.78 (1) | 2.6041 (17) | 169 (3) |
N1—H1C···O1i | 0.88 (1) | 1.91 (1) | 2.781 (2) | 176 (2) |
N2—H2B···O5ii | 0.86 (1) | 2.49 (1) | 3.306 (3) | 159 (2) |
O3—H3A···O6iii | 0.82 (1) | 2.09 (2) | 2.858 (2) | 156 (3) |
O6—H6A···O1iv | 0.83 (1) | 1.88 (1) | 2.7075 (19) | 175 (3) |
C13—H13···Cg1 | 0.93 | 2.80 | 3.437 (2) | 127 |
C6—H6···Cg3ii | 0.93 | 2.87 | 3.554 (2) | 132 |
C19—H19···Cg2v | 0.93 | 2.87 | 3.532 (2) | 129 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+1; (iii) x−1, y−1, z+1; (iv) −x+1, −y+2, −z+1; (v) x−1, y, z. |
Acknowledgements
The authors acknowledge the SAIF, IIT, Madras, for the data collection.
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