organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2414-3146

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

CROSSMARK_Color_square_no_text.svg

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.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

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[link]). 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[Fun, H.-K., Yeap, C. S., Siddegowda, M. S., Yathirajan, H. S. & Narayana, B. (2011). Acta Cryst. E67, o1584.]; Mani et al., 2015[Mani, A., Kumar, P. P. & Chakkaravarthi, G. (2015). Acta Cryst. E71, o643-o644.]; Mathlouthi et al., 2014[Mathlouthi, M., Janzen, D. E., Rzaigui, M. & Smirani Sta, W. (2014). Acta Cryst. E70, o1183-o1184.]).

[Figure 1]
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[link] and Fig. 2[link]).

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 DA 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.
[Figure 2]
Figure 2
Hydrogen bonds within the asymmetric unit.

In 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[link]] hydrogen bonds generate [R_{4}^{4}](20) and [R_{4}^{4}](24) ring-motifs, respectively (Fig. 3[link]), which generate a three-dimensional network (Fig. 4[link]). The crystal structure also features weak C—H⋯π inter­actions.

[Figure 3]
Figure 3
Partial crystal packing, showing the ring motif.
[Figure 4]
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[link].

Table 2
Experimental details

Crystal data
Chemical formula C8H12N+·C7H5O3·C8H11N·C7H6O3
Mr 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)
V3) 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[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.688, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections 35698, 7024, 4026
Rint 0.070
(sin θ/λ)max−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
Δρmax, Δρmin (e Å−3) 0.26, −0.30
Computer programs: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2016/4 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Structural data


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·C7H6O3Z = 2
Mr = 518.59F(000) = 552
Triclinic, P1Dx = 1.304 Mg m3
a = 9.6854 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.9169 (6) ÅCell parameters from 6719 reflections
c = 13.1450 (7) Åθ = 2.3–29.4°
α = 79.029 (4)°µ = 0.09 mm1
β = 75.615 (3)°T = 295 K
γ = 85.345 (4)°Block, colourless
V = 1320.86 (13) Å30.26 × 0.24 × 0.20 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
4026 reflections with I > 2σ(I)
ω and φ scanRint = 0.070
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
θmax = 29.5°, θmin = 2.2°
Tmin = 0.688, Tmax = 0.746h = 1313
35698 measured reflectionsk = 1515
7024 independent reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.059H 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 reflectionsΔρmax = 0.26 e Å3
376 parametersΔρmin = 0.30 e Å3
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
xyzUiso*/Ueq
C10.86255 (19)0.17699 (16)0.55783 (14)0.0292 (4)
C20.72606 (19)0.22707 (16)0.59077 (14)0.0277 (4)
C30.6211 (2)0.16170 (17)0.66719 (14)0.0323 (4)
H30.5298430.1975200.6853340.039*
C40.6513 (2)0.04190 (18)0.71738 (15)0.0377 (5)
C50.7887 (2)0.00660 (18)0.68915 (16)0.0406 (5)
H50.8122820.0850840.7238020.049*
C60.8915 (2)0.05903 (17)0.61069 (15)0.0358 (4)
H60.9827810.0232650.5927010.043*
C70.9738 (2)0.24619 (19)0.46942 (16)0.0400 (5)
H7A1.0600980.1955340.4578430.060*
H7B0.9922730.3226960.4887350.060*
H7C0.9400660.2645690.4051900.060*
C80.5368 (3)0.0305 (2)0.8010 (2)0.0635 (7)
H8A0.5031450.0924720.7710130.095*
H8B0.4591040.0254930.8252360.095*
H8C0.5752790.0705560.8601160.095*
C90.7449 (2)0.49451 (19)0.82967 (18)0.0437 (5)
C100.6808 (2)0.4508 (2)0.93580 (18)0.0498 (6)
H100.6321240.5073130.9780340.060*
C110.6869 (2)0.3264 (2)0.98062 (17)0.0492 (6)
H110.6431470.3003541.0521850.059*
C120.7577 (2)0.24010 (19)0.91973 (16)0.0405 (5)
C130.8226 (2)0.28259 (18)0.81374 (15)0.0360 (4)
H130.8694640.2254920.7714070.043*
C140.8192 (2)0.40806 (18)0.76934 (15)0.0355 (5)
C150.7351 (3)0.6308 (2)0.7828 (2)0.0734 (8)
H15A0.6727590.6741990.8343250.110*
H15B0.6980400.6402910.7203020.110*
H15C0.8282620.6648170.7636700.110*
C160.7672 (3)0.1037 (2)0.9659 (2)0.0704 (8)
H16A0.8541960.0854350.9891950.106*
H16B0.7659390.0550340.9125360.106*
H16C0.6873790.0833531.0255830.106*
C170.29119 (19)0.44302 (15)0.80120 (13)0.0267 (4)
C180.1466 (2)0.45138 (17)0.84845 (15)0.0332 (4)
H180.0899700.5139130.8186560.040*
C190.0851 (2)0.36894 (17)0.93867 (15)0.0356 (5)
H190.0121490.3755210.9689500.043*
C200.1690 (2)0.27650 (17)0.98379 (15)0.0365 (5)
C210.3135 (2)0.26666 (17)0.93802 (15)0.0398 (5)
H210.3698890.2042210.9682340.048*
C220.3739 (2)0.34920 (16)0.84780 (14)0.0324 (4)
H220.4711450.3421920.8175920.039*
C230.3543 (2)0.53064 (16)0.70188 (14)0.0293 (4)
C240.73147 (18)0.84066 (16)0.39196 (14)0.0283 (4)
C250.82153 (19)0.85457 (17)0.29055 (15)0.0321 (4)
H250.8587310.7842450.2613710.039*
C260.8563 (2)0.97198 (17)0.23265 (15)0.0348 (4)
H260.9168040.9804860.1647940.042*
C270.80129 (19)1.07684 (16)0.27555 (14)0.0303 (4)
C280.70977 (19)1.06454 (16)0.37624 (15)0.0321 (4)
H280.6718541.1350020.4049620.039*
C290.67551 (19)0.94683 (17)0.43341 (15)0.0326 (4)
H290.6139060.9385080.5008190.039*
C300.6966 (2)0.71342 (17)0.45436 (15)0.0319 (4)
N10.69424 (19)0.35629 (15)0.54491 (14)0.0348 (4)
N20.8895 (2)0.44564 (19)0.66002 (15)0.0488 (5)
O10.28132 (14)0.62590 (11)0.67266 (10)0.0380 (3)
O20.47869 (14)0.50631 (11)0.64920 (10)0.0391 (3)
O30.11541 (18)0.19274 (14)1.07406 (13)0.0578 (5)
O40.57699 (16)0.71376 (13)0.52863 (13)0.0515 (4)
O50.77000 (15)0.62033 (12)0.43902 (12)0.0455 (4)
O60.83921 (16)1.19187 (12)0.21635 (11)0.0446 (4)
H1A0.755 (2)0.4040 (18)0.5552 (18)0.057 (7)*
H1B0.6106 (14)0.379 (2)0.5801 (16)0.052 (7)*
H1C0.698 (3)0.363 (2)0.4768 (9)0.063 (8)*
H2A0.898 (3)0.5244 (10)0.643 (2)0.080 (9)*
H2B0.9714 (16)0.409 (2)0.644 (2)0.077 (10)*
H3A0.0300 (14)0.206 (3)1.099 (3)0.116*
H4A0.555 (3)0.6430 (15)0.564 (2)0.116*
H6A0.798 (3)1.248 (2)0.248 (2)0.116*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0304 (10)0.0291 (9)0.0274 (9)0.0006 (8)0.0047 (7)0.0066 (7)
C20.0305 (10)0.0246 (9)0.0270 (9)0.0016 (7)0.0079 (7)0.0017 (7)
C30.0280 (10)0.0344 (10)0.0321 (10)0.0014 (8)0.0061 (8)0.0024 (8)
C40.0402 (12)0.0352 (10)0.0346 (11)0.0067 (9)0.0087 (9)0.0033 (8)
C50.0507 (13)0.0272 (10)0.0431 (12)0.0037 (9)0.0168 (10)0.0016 (8)
C60.0351 (11)0.0340 (10)0.0386 (11)0.0106 (8)0.0108 (9)0.0094 (8)
C70.0324 (11)0.0423 (11)0.0404 (11)0.0010 (9)0.0002 (9)0.0066 (9)
C80.0565 (16)0.0587 (15)0.0611 (16)0.0163 (12)0.0068 (12)0.0209 (12)
C90.0435 (13)0.0386 (11)0.0511 (13)0.0002 (9)0.0115 (10)0.0137 (10)
C100.0416 (13)0.0555 (14)0.0532 (14)0.0027 (11)0.0014 (10)0.0263 (12)
C110.0422 (13)0.0647 (15)0.0369 (12)0.0092 (11)0.0037 (9)0.0137 (11)
C120.0399 (12)0.0432 (11)0.0370 (11)0.0069 (9)0.0063 (9)0.0054 (9)
C130.0364 (11)0.0356 (10)0.0353 (11)0.0017 (9)0.0044 (8)0.0099 (8)
C140.0334 (11)0.0396 (11)0.0343 (10)0.0070 (9)0.0060 (8)0.0089 (9)
C150.099 (2)0.0411 (14)0.078 (2)0.0072 (14)0.0171 (17)0.0165 (13)
C160.096 (2)0.0541 (15)0.0500 (15)0.0076 (14)0.0086 (14)0.0071 (12)
C170.0291 (10)0.0227 (8)0.0254 (9)0.0010 (7)0.0025 (7)0.0021 (7)
C180.0308 (10)0.0305 (9)0.0348 (10)0.0013 (8)0.0058 (8)0.0007 (8)
C190.0267 (10)0.0370 (10)0.0372 (11)0.0046 (8)0.0034 (8)0.0053 (8)
C200.0438 (12)0.0292 (10)0.0300 (10)0.0079 (9)0.0010 (8)0.0011 (8)
C210.0426 (12)0.0315 (10)0.0363 (11)0.0069 (9)0.0038 (9)0.0055 (8)
C220.0284 (10)0.0324 (10)0.0312 (10)0.0037 (8)0.0015 (8)0.0025 (8)
C230.0328 (10)0.0235 (9)0.0287 (9)0.0025 (8)0.0032 (8)0.0021 (7)
C240.0236 (9)0.0265 (9)0.0325 (10)0.0014 (7)0.0054 (7)0.0009 (7)
C250.0303 (10)0.0279 (9)0.0356 (10)0.0022 (8)0.0031 (8)0.0073 (8)
C260.0350 (11)0.0338 (10)0.0288 (10)0.0009 (8)0.0025 (8)0.0030 (8)
C270.0266 (10)0.0280 (9)0.0314 (10)0.0020 (7)0.0036 (7)0.0027 (7)
C280.0320 (10)0.0257 (9)0.0356 (10)0.0019 (8)0.0025 (8)0.0064 (8)
C290.0284 (10)0.0326 (10)0.0311 (10)0.0001 (8)0.0004 (8)0.0018 (8)
C300.0288 (10)0.0296 (10)0.0363 (10)0.0041 (8)0.0084 (8)0.0011 (8)
N10.0363 (10)0.0284 (9)0.0343 (10)0.0036 (8)0.0029 (8)0.0013 (7)
N20.0612 (14)0.0395 (11)0.0398 (11)0.0093 (10)0.0009 (9)0.0037 (9)
O10.0447 (8)0.0263 (7)0.0345 (7)0.0083 (6)0.0022 (6)0.0023 (5)
O20.0354 (8)0.0313 (7)0.0373 (8)0.0019 (6)0.0073 (6)0.0044 (6)
O30.0618 (11)0.0443 (9)0.0462 (9)0.0062 (8)0.0100 (8)0.0156 (7)
O40.0413 (9)0.0330 (8)0.0599 (10)0.0007 (7)0.0115 (7)0.0101 (7)
O50.0466 (9)0.0274 (7)0.0550 (9)0.0009 (6)0.0031 (7)0.0017 (6)
O60.0520 (9)0.0282 (7)0.0404 (8)0.0031 (7)0.0064 (7)0.0036 (6)
Geometric parameters (Å, º) top
C1—C61.385 (2)C17—C181.387 (2)
C1—C21.386 (3)C17—C221.392 (2)
C1—C71.503 (2)C17—C231.489 (2)
C2—C31.375 (2)C18—C191.379 (2)
C2—N11.465 (2)C18—H180.9300
C3—C41.392 (3)C19—C201.381 (3)
C3—H30.9300C19—H190.9300
C4—C51.380 (3)C20—O31.368 (2)
C4—C81.506 (3)C20—C211.384 (3)
C5—C61.376 (3)C21—C221.376 (2)
C5—H50.9300C21—H210.9300
C6—H60.9300C22—H220.9300
C7—H7A0.9600C23—O11.262 (2)
C7—H7B0.9600C23—O21.267 (2)
C7—H7C0.9600C24—C291.388 (2)
C8—H8A0.9600C24—C251.388 (2)
C8—H8B0.9600C24—C301.490 (2)
C8—H8C0.9600C25—C261.381 (2)
C9—C101.387 (3)C25—H250.9300
C9—C141.389 (3)C26—C271.382 (3)
C9—C151.503 (3)C26—H260.9300
C10—C111.376 (3)C27—O61.371 (2)
C10—H100.9300C27—C281.387 (2)
C11—C121.381 (3)C28—C291.380 (2)
C11—H110.9300C28—H280.9300
C12—C131.385 (3)C29—H290.9300
C12—C161.502 (3)C30—O51.212 (2)
C13—C141.384 (3)C30—O41.317 (2)
C13—H130.9300N1—H1A0.869 (9)
C14—N21.425 (3)N1—H1B0.871 (9)
C15—H15A0.9600N1—H1C0.876 (10)
C15—H15B0.9600N2—H2A0.852 (10)
C15—H15C0.9600N2—H2B0.856 (10)
C16—H16A0.9600O3—H3A0.824 (10)
C16—H16B0.9600O4—H4A0.834 (10)
C16—H16C0.9600O6—H6A0.830 (10)
C6—C1—C2116.45 (16)C12—C16—H16C109.5
C6—C1—C7121.39 (17)H16A—C16—H16C109.5
C2—C1—C7122.15 (16)H16B—C16—H16C109.5
C3—C2—C1122.61 (16)C18—C17—C22118.19 (16)
C3—C2—N1118.80 (17)C18—C17—C23120.40 (16)
C1—C2—N1118.55 (16)C22—C17—C23121.39 (16)
C2—C3—C4119.97 (18)C19—C18—C17121.40 (17)
C2—C3—H3120.0C19—C18—H18119.3
C4—C3—H3120.0C17—C18—H18119.3
C5—C4—C3117.97 (17)C18—C19—C20119.55 (17)
C5—C4—C8121.70 (19)C18—C19—H19120.2
C3—C4—C8120.3 (2)C20—C19—H19120.2
C6—C5—C4121.20 (17)O3—C20—C19122.63 (18)
C6—C5—H5119.4O3—C20—C21117.39 (18)
C4—C5—H5119.4C19—C20—C21119.98 (16)
C5—C6—C1121.67 (18)C22—C21—C20120.05 (18)
C5—C6—H6119.2C22—C21—H21120.0
C1—C6—H6119.2C20—C21—H21120.0
C1—C7—H7A109.5C21—C22—C17120.83 (17)
C1—C7—H7B109.5C21—C22—H22119.6
H7A—C7—H7B109.5C17—C22—H22119.6
C1—C7—H7C109.5O1—C23—O2122.37 (16)
H7A—C7—H7C109.5O1—C23—C17118.75 (16)
H7B—C7—H7C109.5O2—C23—C17118.87 (16)
C4—C8—H8A109.5C29—C24—C25118.81 (16)
C4—C8—H8B109.5C29—C24—C30121.15 (16)
H8A—C8—H8B109.5C25—C24—C30120.04 (16)
C4—C8—H8C109.5C26—C25—C24120.55 (17)
H8A—C8—H8C109.5C26—C25—H25119.7
H8B—C8—H8C109.5C24—C25—H25119.7
C10—C9—C14117.50 (19)C25—C26—C27119.99 (17)
C10—C9—C15120.9 (2)C25—C26—H26120.0
C14—C9—C15121.6 (2)C27—C26—H26120.0
C11—C10—C9122.1 (2)O6—C27—C26118.45 (16)
C11—C10—H10118.9O6—C27—C28121.39 (16)
C9—C10—H10118.9C26—C27—C28120.16 (16)
C10—C11—C12120.2 (2)C29—C28—C27119.41 (17)
C10—C11—H11119.9C29—C28—H28120.3
C12—C11—H11119.9C27—C28—H28120.3
C11—C12—C13118.20 (19)C28—C29—C24121.08 (17)
C11—C12—C16121.8 (2)C28—C29—H29119.5
C13—C12—C16120.0 (2)C24—C29—H29119.5
C14—C13—C12121.52 (19)O5—C30—O4123.77 (16)
C14—C13—H13119.2O5—C30—C24124.02 (17)
C12—C13—H13119.2O4—C30—C24112.21 (16)
C13—C14—C9120.33 (18)C2—N1—H1A108.4 (16)
C13—C14—N2118.65 (18)C2—N1—H1B108.7 (15)
C9—C14—N2120.99 (19)H1A—N1—H1B106 (2)
C9—C15—H15A109.5C2—N1—H1C110.5 (16)
C9—C15—H15B109.5H1A—N1—H1C111 (2)
H15A—C15—H15B109.5H1B—N1—H1C111 (2)
C9—C15—H15C109.5C14—N2—H2A112.1 (19)
H15A—C15—H15C109.5C14—N2—H2B112.1 (19)
H15B—C15—H15C109.5H2A—N2—H2B109 (3)
C12—C16—H16A109.5C20—O3—H3A113 (2)
C12—C16—H16B109.5C30—O4—H4A113 (2)
H16A—C16—H16B109.5C27—O6—H6A111 (2)
C6—C1—C2—C33.8 (3)C23—C17—C18—C19178.08 (17)
C7—C1—C2—C3176.07 (18)C17—C18—C19—C200.5 (3)
C6—C1—C2—N1173.96 (17)C18—C19—C20—O3179.08 (19)
C7—C1—C2—N16.1 (3)C18—C19—C20—C210.4 (3)
C1—C2—C3—C42.3 (3)O3—C20—C21—C22179.26 (18)
N1—C2—C3—C4175.54 (18)C19—C20—C21—C220.3 (3)
C2—C3—C4—C51.1 (3)C20—C21—C22—C170.2 (3)
C2—C3—C4—C8179.88 (19)C18—C17—C22—C210.3 (3)
C3—C4—C5—C62.7 (3)C23—C17—C22—C21178.23 (17)
C8—C4—C5—C6178.3 (2)C18—C17—C23—O113.0 (3)
C4—C5—C6—C11.0 (3)C22—C17—C23—O1168.48 (17)
C2—C1—C6—C52.2 (3)C18—C17—C23—O2166.33 (17)
C7—C1—C6—C5177.70 (18)C22—C17—C23—O212.2 (3)
C14—C9—C10—C111.3 (3)C29—C24—C25—C260.9 (3)
C15—C9—C10—C11179.4 (2)C30—C24—C25—C26179.00 (17)
C9—C10—C11—C120.4 (4)C24—C25—C26—C270.1 (3)
C10—C11—C12—C130.6 (3)C25—C26—C27—O6179.34 (17)
C10—C11—C12—C16179.7 (2)C25—C26—C27—C280.7 (3)
C11—C12—C13—C140.9 (3)O6—C27—C28—C29179.42 (17)
C16—C12—C13—C14178.2 (2)C26—C27—C28—C290.7 (3)
C12—C13—C14—C92.6 (3)C27—C28—C29—C240.2 (3)
C12—C13—C14—N2179.36 (19)C25—C24—C29—C281.0 (3)
C10—C9—C14—C132.7 (3)C30—C24—C29—C28178.92 (17)
C15—C9—C14—C13177.9 (2)C29—C24—C30—O5157.41 (19)
C10—C9—C14—N2179.3 (2)C25—C24—C30—O522.5 (3)
C15—C9—C14—N20.1 (3)C29—C24—C30—O422.3 (2)
C22—C17—C18—C190.5 (3)C25—C24—C30—O4157.83 (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···AD—HH···AD···AD—H···A
N1—H1A···O50.87 (1)2.55 (2)3.015 (2)114 (2)
N1—H1A···N20.87 (1)2.24 (2)3.016 (3)149 (2)
N1—H1B···O20.87 (1)2.00 (1)2.792 (2)151 (2)
O4—H4A···O20.83 (1)1.78 (1)2.6041 (17)169 (3)
N1—H1C···O1i0.88 (1)1.91 (1)2.781 (2)176 (2)
N2—H2B···O5ii0.86 (1)2.49 (1)3.306 (3)159 (2)
O3—H3A···O6iii0.82 (1)2.09 (2)2.858 (2)156 (3)
O6—H6A···O1iv0.83 (1)1.88 (1)2.7075 (19)175 (3)
C13—H13···Cg10.932.803.437 (2)127
C6—H6···Cg3ii0.932.873.554 (2)132
C19—H19···Cg2v0.932.873.532 (2)129
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y+1, z+1; (iii) x1, y1, z+1; (iv) x+1, y+2, z+1; (v) x1, y, z.
 

Acknowledgements

The authors acknowledge the SAIF, IIT, Madras, for the data collection.

References

First citationBruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFun, H.-K., Yeap, C. S., Siddegowda, M. S., Yathirajan, H. S. & Narayana, B. (2011). Acta Cryst. E67, o1584.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationMani, A., Kumar, P. P. & Chakkaravarthi, G. (2015). Acta Cryst. E71, o643–o644.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationMathlouthi, M., Janzen, D. E., Rzaigui, M. & Smirani Sta, W. (2014). Acta Cryst. E70, o1183–o1184.  CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015). Acta Cryst. A71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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