2,5-Di­methyl­anilinium 4-hy­droxy­benzoate–2,5-di­methyl­aniline–4-hy­droxy­benzoic acid (1/1/1)

Mani, A.; Rajesh, K.; Kumar, P.P.; Chakkaravarthi, G.

doi:10.1107/S2414314616016072

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 10| October 2016| x161607

https://doi.org/10.1107/S2414314616016072

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2,5-Dimethylanilinium 4-hydroxybenzoate–2,5-dimethylaniline–4-hydroxybenzoic acid (1/1/1)

A. Mani,^a,^b K. Rajesh,^c P. Praveen Kumar ^b ^* and G. Chakkaravarthi ^d ^*

^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

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 9 October 2016; accepted 11 October 2016; online 14 October 2016)

The asymmetric unit of the title compound, C₈H₁₂N⁺·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 crystal structure also features weak C—H⋯π interactions.

Keywords: 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 ).

Figure 1
The molecular structure of the title compound, with 30% probability displacement ellipsoids.

In the arbitrarily chosen asymmetric unit, the anion and cation are connected by an N1—H1B⋯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 $[R_{2}^{2}]$ (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).

Table 1
Hydrogen-bond geometry (Å, °)

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⋯O1^iv	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⋯Cg2^v	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.

Figure 2
Hydrogen bonds within the asymmetric unit.

In the extended structure, pairs of O—H⋯O [(O3—H3A⋯O6^iv and O6—H6A⋯O1ⁱⁱⁱ) and (O6—H6A⋯O1ⁱⁱⁱ and O4—H4A⋯O2); for symmetry codes, see Table 1] hydrogen bonds generate $[R_{4}^{4}]$ (20) and $[R_{4}^{4}]$ (24) ring-motifs, respectively (Fig. 3), which generate a three-dimensional network (Fig. 4). The crystal structure also features weak C—H⋯π interactions.

Figure 3
Partial crystal packing, showing the ring motif.

Figure 4
The crystal packing of the title compound viewed along the a axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

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 refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₈H₁₂N⁺·C₇H₅O₃⁻·C₈H₁₁N·C₇H₆O₃
M_r	518.59
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	295
a, b, c (Å)	9.6854 (5), 10.9169 (6), 13.1450 (7)
α, β, γ (°)	79.029 (4), 75.615 (3), 85.345 (4)
V (Å³)	1320.86 (13)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.26 × 0.24 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004 )
T_min, T_max	0.688, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	35698, 7024, 4026
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.693

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.145, 1.01
No. of reflections	7024
No. of parameters	376
No. of restraints	8
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.30
Computer programs: APEX2 and SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008 ), SHELXL2016/4 (Sheldrick, 2015 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1509213

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314616016072/hb4085sup1.cif

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

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: 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).

2,5-Dimethylanilinium 4-hydroxybenzoate–2,5-dimethylaniline–4-hydroxybenzoic acid (1/1/1) top

Crystal data top

C₈H₁₂N⁺·C₇H₅O₃⁻·C₈H₁₁N·C₇H₆O₃	Z = 2
M_r = 518.59	F(000) = 552
Triclinic, P1	D_x = 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

Data collection top

Bruker Kappa APEXII CCD diffractometer	4026 reflections with I > 2σ(I)
ω and φ scan	R_int = 0.070
Absorption correction: multi-scan (SADABS; Bruker, 2004)	θ_max = 29.5°, θ_min = 2.2°
T_min = 0.688, T_max = 0.746	h = −13→13
35698 measured reflections	k = −15→15
7024 independent reflections	l = −18→18

Refinement top

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(F_o²) + (0.0575P)² + 0.3498P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
7024 reflections	Δρ_max = 0.26 e Å⁻³
376 parameters	Δρ_min = −0.30 e Å⁻³
8 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O1^iv	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···Cg2^v	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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