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

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ISSN: 2414-3146

5-Nitro-N2,N3-bis­[(1R,2R,4R)-1,7,7-tri­methylbi­cyclo[2.2.1]heptan-2-yl]isophthalamide di­chloro­methane hemisolvate

aApicore Pharmaceuticals Pvt Ltd, Block No. 252–253, Dhobikuva Village, Padra-Jambusar Highway, Padra Taluka, Vadodara 391 440, India, bDepartment of Chemistry, Amet University, 135, East Coast Road, Kanathur, Chennai 603 112, India, and cDepartment of Chemistry, Faculty of Science, M. S. University of Baroda, Vadodara 390 002, India
*Correspondence e-mail: avbedekar@yahoo.co.in

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 7 May 2018; accepted 16 May 2018; online 22 May 2018)

The asymmetric unit of the title hemisolvate, C28H39N3O4·0.5CH2Cl2 contains two isophthalamide camphor derivatives and one di­chloro­methane solvent mol­ecule. In the crystal, the chiral mol­ecules are connected into [100] stacks by N—H⋯O and C—H⋯O hydrogen bonds. The stacks are consolidated by C—H⋯N and C—H⋯Cl as well as further C—H⋯O inter­actions.

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

Structure description

The determination of the optical purity of chiral compounds by nuclear magnetic resonance spectroscopy (Laaksonen et al., 2015[Laaksonen, T. S., Heikkinen, S. & Wähälä, K. (2015). Org. Biomol. Chem. 13, 10548-10555.]; Li et al., 2016[Li, G., Cao, J., Zong, W., Lei, X. & Tan, R. (2016). Org. Chem. Front. 3, 96-102.]; Pal et al., 2014[Pal, I., Chaudhari, S. R. & Suryaprakash, N. (2014). New J. Chem. 38, 4908-4912.]) with an aid of suitable homochiral additives has gained importance in recent years. The principle of the separation of signals for the enanti­omers of the analyte is based on supra­molecular inter­actions with the chiral additive such as hydrogen bonding, C—H⋯π, ππ inter­actions, etc. We have recently reported a chiral camphor-based Kagan's amide and explored its activity for estimation of enanti­omer ratios of a wide variety of functionalized mol­ecules (Kannappan et al., 2015[Kannappan, J., Jain, N. & Bedekar, A. V. (2015). Tetrahedron Asymmetry, 26, 1102-1107.], 2017[Kannappan, J., Khanvilkar, A. N., Upadhyay, G. M. & Bedekar, A. V. (2017). Tetrahedron Asymmetry, 28, 1297-1303.]). As part of our ongoing studies in this area, we now report the synthesis and structure of the title compound (Fig. 1[link]).

[Figure 1]
Figure 1
Asymmetric unit of title compound showing displacement ellipsoids drawn at the 40% probability level. Hydrogen atoms are omitted for clarity.

The asymmetric unit contains two mol­ecules, A (containing C1) and B (containing C30), of the chiral isopthalimide compound and one di­chloro­methane solvent mol­ecule (Fig. 1[link]). In the extended structure, the main mol­ecules are linked by N—H⋯O hydrogen bonds (Table 1[link]) to generate [100] stacks (Fig. 2[link]) of alternating A and B mol­ecules, with an approximate rotation of 60° between adjacent mol­ecules in the stack. The structure is consolidated by C—H⋯O, C—H⋯Cl and C—H⋯N inter­actions (which also involve the solvent mol­ecules as both donors and acceptors), which consolidate the chains into ribbon-like networks.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2A⋯O7 0.86 (1) 2.07 (1) 2.881 (5) 158 (1)
N3—H3⋯O8 0.86 (1) 2.21 (1) 3.047 (5) 165 (1)
N6—H6A⋯O4i 0.86 (1) 2.13 (1) 2.970 (4) 165 (1)
C17—H17B⋯O8 0.96 (2) 2.55 (3) 3.445 (8) 156 (2)
C17—H17B⋯N3 0.96 (2) 2.55 (1) 3.260 (7) 131 (2)
C24—H24B⋯Cl1ii 0.97 (1) 2.77 (1) 3.388 (8) 123 (1)
C27—H27B⋯O7 0.96 (4) 2.56 (4) 3.491 (8) 164 (2)
C27—H27B⋯N2 0.96 (4) 2.60 (3) 3.218 (8) 122 (3)
C29—H29A⋯O6iii 0.97 (2) 2.49 (1) 3.229 (14) 133 (1)
C29—H29B⋯O3iv 0.97 (2) 2.41 (1) 3.046 (14) 123 (1)
C44—H44B⋯N6 0.96 (3) 2.62 (3) 2.940 (7) 100 (2)
C47—H47B⋯O4i 0.96 (3) 2.42 (3) 3.331 (8) 158 (1)
C50—H50B⋯Cl2 0.97 (1) 2.72 (1) 3.617 (9) 154 (1)
Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z-1; (iii) x-1, y, z+1; (iv) x, y, z+1.
[Figure 2]
Figure 2
Detail of the extended structure showing [100] stacked layer formation of the C1 (green) and C30 (blue) mol­ecules due to N—H⋯O and C—H⋯O hydrogen bonds

Synthesis and crystallization

To a dry 50 ml round-bottom flask containing a solution of (−)-iso-bornyl amine (0.25 g, 1.6 mmol) dissolved in dry chloro­form (5 ml), was added tri­ethyl­amine (0.57 ml, 4.1 mmol). The mixture was allowed to cool to 273 K and a solution of iso-phthaloyl acid chloride (0.89 g, 3.6 mmol) dissolved in chloro­form was added dropwise with a syringe. The reaction mixture was then stirred at room temperature for 4 h. The solvent was evaporated under vacuum and the residue was washed with sodium bicarbonate and extracted with di­chloro­methane (3 × 50 ml). The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by short column chromatography over silica gel (50% ethyl acetate–petroleum ether) resulting in a white solid. Thin plates were recrystallized from a solvent mixture of di­chloro­methane/methanol at room temperature.

1H NMR (400 MHz, CDCl3): δ 0.90 (3H, s), 0.94 (3H, s), 1.04 (3H, s), 1.21–1.29 (2H, m), 1.35–1.41 (1H, m), 1.63–1.79 (3H, m), 1.84–1.87 (1H, m), 1.96–2.02 (1H, m), 4.11–4.16 (1H, m), 6.21–6.23 (1H, d, J = 3.2 Hz), 8.39 (1H, s), 8.64 (2H, s).

13C NMR (100 MHz, CDCl3): δ 11.9, 20.2, 20.5, 27.0, 35.9, 38.9, 44.9, 47.3, 49.1, 57.9, 123.9, 130.6, 137.2, 148.3, 163.8.

IR (KBr): ν (cm−1) 3266, 3067, 2953, 1638, 1537, 1457, 1389, 1352, 1114, 979.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. Bond length restraints were applied to model the solvent mol­ecule.

Table 2
Experimental details

Crystal data
Chemical formula 2C28H39N3O4·CH2Cl2
Mr 1048.17
Crystal system, space group Triclinic, P1
Temperature (K) 293
a, b, c (Å) 7.2828 (4), 12.6801 (8), 16.9826 (9)
α, β, γ (°) 70.373 (5), 78.541 (5), 78.791 (5)
V3) 1433.81 (15)
Z 1
Radiation type Mo Kα
μ (mm−1) 0.17
Crystal size (mm) 0.25 × 0.12 × 0.08
 
Data collection
Diffractometer Agilent Xcalibur, Eos, Gemini
Absorption correction Multi-scan (CrysAlis PRO; Rigaku OD, 2017[Rigaku OD (2017). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.])
Tmin, Tmax 0.912, 1.000
No. of measured, independent and observed [I ≥ 2σ(I)] reflections 9570, 8140, 5575
Rint 0.025
(sin θ/λ)max−1) 0.684
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.072, 0.208, 1.07
No. of reflections 8140
No. of parameters 671
No. of restraints 7
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.37, −0.36
Absolute structure Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.])
Absolute structure parameter 0.1 (3)
Computer programs: CrysAlis PRO (Rigaku OD, 2017[Rigaku OD (2017). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]), SHELXD (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), olex2.refine (Bourhis et al., 2015[Bourhis, L. J., Dolomanov, O. V., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2015). Acta Cryst. A71, 59-75.]) and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

Structural data


Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2017); cell refinement: CrysAlis PRO (Rigaku OD, 2017); data reduction: CrysAlis PRO (Rigaku OD, 2017); program(s) used to solve structure: SHELXD (Sheldrick, 2008); program(s) used to refine structure: olex2.refine (Bourhis et al., 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

5-Nitro-N2,N3-bis[(1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl]isophthalamide dichloromethane hemisolvate top
Crystal data top
2C28H39N3O4·CH2Cl2Z = 1
Mr = 1048.17F(000) = 1433.81
Triclinic, P1Dx = 1.214 Mg m3
a = 7.2828 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.6801 (8) ÅCell parameters from 1895 reflections
c = 16.9826 (9) Åθ = 3.8–24.9°
α = 70.373 (5)°µ = 0.17 mm1
β = 78.541 (5)°T = 293 K
γ = 78.791 (5)°Plate, colourless
V = 1433.81 (15) Å30.25 × 0.12 × 0.08 mm
Data collection top
Agilent Xcalibur, Eos, Gemini
diffractometer
8140 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source5575 reflections with I 2σ(I)
Graphite monochromatorRint = 0.025
Detector resolution: 16.1702 pixels mm-1θmax = 29.1°, θmin = 3.4°
ω scansh = 98
Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2017)
k = 1516
Tmin = 0.912, Tmax = 1.000l = 2122
9570 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.072 w = 1/[σ2(Fo2) + (0.1179P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.208(Δ/σ)max = 0.003
S = 1.07Δρmax = 0.37 e Å3
8140 reflectionsΔρmin = 0.36 e Å3
671 parametersAbsolute structure: Flack (1983)
7 restraintsAbsolute structure parameter: 0.1 (3)
123 constraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C30.0709 (5)0.6303 (3)0.4855 (3)0.0378 (9)
O70.3557 (4)0.5252 (3)0.6951 (2)0.0519 (8)
C370.4311 (5)0.5267 (3)0.6350 (3)0.0374 (9)
N30.0898 (4)0.5098 (3)0.3990 (2)0.0432 (8)
H30.0138 (4)0.5626 (3)0.3701 (2)0.0518 (10)*
C310.4213 (5)0.6375 (4)0.4816 (3)0.0380 (9)
H310.3742 (5)0.5708 (4)0.4686 (3)0.0456 (11)*
C40.0434 (6)0.7339 (4)0.4242 (3)0.0453 (10)
H40.0639 (6)0.7397 (4)0.3672 (3)0.0544 (12)*
C300.4655 (5)0.6342 (3)0.5655 (3)0.0381 (9)
C320.4458 (6)0.7382 (4)0.4163 (3)0.0445 (10)
C10.0193 (5)0.7214 (4)0.5955 (3)0.0393 (9)
C20.0385 (5)0.6258 (4)0.5707 (3)0.0388 (9)
H20.0567 (5)0.5560 (4)0.6118 (3)0.0465 (11)*
C60.0454 (6)0.8266 (4)0.5334 (3)0.0480 (11)
H60.0819 (6)0.8929 (4)0.5479 (3)0.0576 (13)*
C330.5191 (6)0.8373 (4)0.4348 (3)0.0463 (11)
H330.5413 (6)0.9049 (4)0.3920 (3)0.0556 (13)*
C340.5589 (6)0.8337 (4)0.5190 (3)0.0461 (10)
O40.2644 (4)0.4548 (3)0.5058 (2)0.0537 (8)
N60.4826 (4)0.4350 (3)0.6288 (2)0.0390 (8)
H6a0.5362 (4)0.4417 (3)0.5863 (2)0.0468 (9)*
O80.2376 (5)0.6668 (3)0.3150 (2)0.0612 (9)
N20.1087 (5)0.6359 (3)0.7448 (2)0.0479 (9)
H2a0.1553 (5)0.5897 (3)0.7296 (2)0.0575 (11)*
C80.1496 (5)0.5243 (4)0.4641 (3)0.0388 (9)
C50.0159 (6)0.8289 (4)0.4508 (3)0.0460 (10)
N40.6336 (6)0.9388 (4)0.5380 (3)0.0668 (12)
C380.4524 (6)0.3238 (4)0.6909 (3)0.0440 (10)
H380.4527 (6)0.3341 (4)0.7456 (3)0.0529 (12)*
C70.0301 (6)0.7189 (4)0.6851 (3)0.0477 (11)
N10.0340 (7)0.9410 (4)0.3838 (3)0.0726 (13)
O30.0381 (5)0.7917 (3)0.6991 (2)0.0686 (10)
C360.3776 (6)0.7343 (4)0.3277 (3)0.0483 (11)
N50.4729 (5)0.8057 (4)0.2668 (3)0.0609 (11)
H50.5707 (5)0.8501 (4)0.2800 (3)0.0731 (14)*
C100.3277 (6)0.4052 (4)0.3073 (3)0.0526 (11)
C190.1209 (6)0.6182 (5)0.8350 (3)0.0537 (12)
H190.1230 (6)0.6918 (5)0.8425 (3)0.0645 (14)*
C90.1521 (6)0.4051 (4)0.3766 (3)0.0455 (10)
H90.1785 (6)0.3430 (4)0.4278 (3)0.0546 (12)*
C480.4155 (8)0.8101 (5)0.1790 (3)0.0683 (15)
H480.3501 (8)0.7353 (5)0.1777 (3)0.0820 (18)*
O60.6104 (7)0.9452 (4)0.6048 (4)0.1045 (16)
C390.2671 (7)0.2463 (4)0.6711 (3)0.0579 (13)
C200.0443 (6)0.5350 (5)0.8790 (3)0.0617 (14)
C430.6074 (7)0.2506 (4)0.7011 (3)0.0624 (14)
H43a0.6826 (7)0.2825 (4)0.6553 (3)0.0748 (16)*
H43b0.6902 (7)0.2435 (4)0.7545 (3)0.0748 (16)*
C160.2411 (7)0.4367 (4)0.2257 (3)0.0573 (12)
C130.1110 (8)0.3453 (5)0.2620 (4)0.0701 (15)
H130.0326 (8)0.3430 (5)0.2221 (4)0.0841 (18)*
O20.1482 (8)1.0153 (4)0.4026 (4)0.120 (2)
C490.2870 (8)0.8980 (6)0.1239 (4)0.0806 (19)
C140.0015 (7)0.3762 (5)0.3387 (3)0.0670 (15)
H14a0.0977 (7)0.4408 (5)0.3222 (3)0.0804 (18)*
H14b0.0612 (7)0.3131 (5)0.3785 (3)0.0804 (18)*
O50.7140 (7)1.0161 (4)0.4861 (4)0.1091 (17)
O10.0738 (7)0.9495 (4)0.3167 (3)0.0989 (15)
C420.4952 (9)0.1375 (4)0.6987 (4)0.0720 (16)
H420.5688 (9)0.0864 (4)0.6899 (4)0.0865 (19)*
C230.2189 (9)0.4713 (6)0.9612 (4)0.0805 (18)
H230.3068 (9)0.4169 (6)0.9929 (4)0.097 (2)*
C240.2968 (7)0.5675 (6)0.8901 (3)0.0726 (16)
H24a0.3625 (7)0.5401 (6)0.8581 (3)0.087 (2)*
H24b0.3834 (7)0.6232 (6)0.9117 (3)0.087 (2)*
C550.4306 (9)0.9997 (5)0.0804 (4)0.0755 (17)
C400.2408 (10)0.1600 (5)0.7582 (5)0.093 (2)
H40a0.2552 (10)0.1977 (5)0.8006 (5)0.112 (3)*
H40b0.1168 (10)0.1151 (5)0.7564 (5)0.112 (3)*
C450.3326 (8)0.1729 (5)0.6279 (4)0.0674 (14)
C250.2354 (7)0.5368 (7)0.8249 (5)0.098 (2)
H25a0.268 (4)0.6119 (13)0.806 (3)0.146 (4)*
H25b0.231 (2)0.514 (5)0.777 (2)0.146 (4)*
H25c0.3285 (16)0.486 (4)0.8575 (12)0.146 (4)*
C520.5194 (11)0.9291 (6)0.0480 (4)0.096 (2)
H520.6207 (11)0.9719 (6)0.0149 (4)0.116 (3)*
C440.0985 (7)0.3089 (6)0.6266 (5)0.093 (2)
H44a0.064 (5)0.343 (4)0.6634 (13)0.140 (3)*
H44b0.131 (3)0.367 (3)0.5761 (19)0.140 (3)*
H44c0.006 (3)0.2567 (11)0.612 (3)0.140 (3)*
C110.3923 (10)0.2764 (6)0.3238 (5)0.095 (2)
H11a0.3969 (10)0.2379 (6)0.3834 (5)0.114 (3)*
H11b0.5165 (10)0.2626 (6)0.2924 (5)0.114 (3)*
C170.1421 (9)0.5574 (5)0.1954 (4)0.0795 (17)
H17a0.2348 (9)0.6084 (6)0.173 (3)0.119 (3)*
H17b0.060 (5)0.5758 (15)0.2420 (7)0.119 (3)*
H17c0.069 (6)0.5641 (11)0.152 (2)0.119 (3)*
C150.4780 (7)0.4719 (6)0.3099 (4)0.083 (2)
H15a0.524 (5)0.440 (3)0.3634 (13)0.125 (3)*
H15b0.424 (2)0.5493 (11)0.303 (3)0.125 (3)*
H15c0.581 (3)0.468 (4)0.265 (2)0.125 (3)*
C260.0388 (8)0.4217 (5)0.9172 (4)0.0673 (14)
C210.0349 (9)0.5685 (6)0.9593 (4)0.087 (2)
H21a0.0267 (9)0.6497 (6)0.9457 (4)0.105 (2)*
H21b0.1453 (9)0.5323 (6)0.9871 (4)0.105 (2)*
C470.3889 (9)0.2378 (6)0.5404 (4)0.0818 (18)
H47a0.289 (3)0.280 (3)0.5059 (11)0.123 (3)*
H47b0.503 (4)0.289 (3)0.5460 (5)0.123 (3)*
H47c0.410 (7)0.1855 (6)0.5144 (13)0.123 (3)*
C180.3868 (9)0.4180 (7)0.1495 (4)0.099 (2)
H18a0.462 (6)0.346 (2)0.1671 (10)0.149 (4)*
H18b0.467 (5)0.476 (3)0.129 (2)0.149 (4)*
H18c0.3210 (9)0.421 (5)0.1050 (15)0.149 (4)*
C220.1465 (11)0.5258 (7)1.0155 (4)0.104 (3)
H22a0.1185 (11)0.4709 (7)1.0688 (4)0.125 (3)*
H22b0.2377 (11)0.5878 (7)1.0265 (4)0.125 (3)*
C410.3960 (11)0.0865 (5)0.7770 (5)0.105 (3)
H41a0.3433 (11)0.0081 (5)0.7838 (5)0.125 (3)*
H41b0.4822 (11)0.0911 (5)0.8276 (5)0.125 (3)*
C270.0718 (10)0.3712 (6)0.8505 (4)0.089 (2)
H27a0.0468 (14)0.355 (4)0.817 (2)0.134 (3)*
H27b0.156 (6)0.4246 (18)0.814 (2)0.134 (3)*
H27c0.127 (7)0.303 (2)0.8786 (4)0.134 (3)*
C120.2438 (11)0.2364 (6)0.2932 (5)0.097 (2)
H12a0.2994 (11)0.2045 (6)0.2478 (5)0.117 (3)*
H12b0.1788 (11)0.1806 (6)0.3388 (5)0.117 (3)*
C460.1869 (11)0.0719 (7)0.6189 (6)0.122 (3)
H46a0.154 (8)0.027 (3)0.6734 (9)0.183 (5)*
H46b0.076 (4)0.0983 (7)0.582 (4)0.183 (5)*
H46c0.239 (4)0.027 (3)0.596 (4)0.183 (5)*
C510.3585 (14)0.8722 (7)0.0006 (5)0.143 (4)
H51a0.3297 (14)0.9203 (7)0.0582 (5)0.172 (5)*
H51b0.3869 (14)0.8010 (7)0.0014 (5)0.172 (5)*
C280.0819 (11)0.3269 (7)0.9774 (5)0.116 (3)
H28a0.108 (8)0.354 (2)1.020 (3)0.174 (4)*
H28b0.199 (4)0.304 (4)0.9458 (9)0.174 (4)*
H28c0.014 (4)0.263 (2)1.004 (3)0.174 (4)*
C530.5879 (11)0.8391 (6)0.1297 (5)0.110 (3)
H53a0.7014 (11)0.8693 (6)0.1604 (5)0.133 (3)*
H53b0.6120 (11)0.7735 (6)0.1183 (5)0.133 (3)*
C560.5597 (14)1.0575 (7)0.1403 (5)0.136 (4)
H56a0.4850 (16)1.076 (6)0.173 (4)0.205 (6)*
H56b0.647 (8)1.008 (3)0.177 (4)0.205 (6)*
H56c0.629 (9)1.126 (4)0.1084 (6)0.205 (6)*
C540.1448 (10)0.9134 (9)0.1727 (5)0.148 (5)
H54a0.085 (10)0.8407 (10)0.203 (5)0.222 (7)*
H54b0.209 (3)0.953 (7)0.212 (5)0.222 (7)*
H54c0.051 (8)0.956 (7)0.1339 (8)0.222 (7)*
C350.5289 (6)0.7347 (4)0.5843 (3)0.0434 (10)
H350.5509 (6)0.7354 (4)0.6400 (3)0.0521 (12)*
C570.3378 (15)1.0945 (7)0.0075 (6)0.160 (5)
H57a0.4348 (15)1.151 (5)0.019 (4)0.241 (7)*
H57b0.259 (12)1.0626 (17)0.034 (3)0.241 (7)*
H57c0.262 (12)1.129 (6)0.0298 (12)0.241 (7)*
C500.2002 (12)0.8543 (9)0.0482 (5)0.143 (4)
H50a0.1500 (12)0.7747 (9)0.0675 (5)0.172 (5)*
H50b0.0990 (12)0.8961 (9)0.0136 (5)0.172 (5)*
Cl20.1590 (3)0.9594 (3)0.1272 (2)0.411 (7)
Cl10.4320 (3)0.8155 (3)0.1924 (3)0.400 (7)
C290.2136 (16)0.8913 (11)0.1980 (8)0.273 (12)
H29a0.2098 (16)0.9451 (11)0.2541 (8)0.327 (14)*
H29b0.1211 (16)0.8409 (11)0.1884 (8)0.327 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C30.033 (2)0.049 (2)0.038 (2)0.0048 (17)0.0108 (17)0.0196 (19)
O70.0617 (18)0.0554 (19)0.0487 (18)0.0157 (15)0.0255 (15)0.0151 (15)
C370.035 (2)0.042 (2)0.039 (2)0.0037 (16)0.0064 (17)0.0181 (18)
N30.0421 (19)0.052 (2)0.0399 (19)0.0040 (15)0.0147 (15)0.0207 (17)
C310.0269 (19)0.044 (2)0.045 (2)0.0029 (16)0.0063 (16)0.0171 (19)
C40.049 (2)0.054 (3)0.037 (2)0.0068 (19)0.0133 (19)0.015 (2)
C300.0282 (19)0.044 (2)0.045 (2)0.0062 (17)0.0096 (17)0.0145 (19)
C320.037 (2)0.047 (3)0.045 (2)0.0049 (18)0.0073 (18)0.009 (2)
C10.0301 (19)0.048 (2)0.045 (2)0.0043 (17)0.0059 (17)0.022 (2)
C20.038 (2)0.049 (2)0.035 (2)0.0053 (18)0.0104 (17)0.0180 (18)
C60.052 (3)0.042 (2)0.058 (3)0.0022 (19)0.015 (2)0.024 (2)
C330.040 (2)0.039 (2)0.052 (3)0.0037 (18)0.0091 (19)0.004 (2)
C340.041 (2)0.035 (2)0.061 (3)0.0061 (18)0.006 (2)0.014 (2)
O40.0506 (18)0.0557 (19)0.062 (2)0.0124 (14)0.0295 (16)0.0272 (16)
N60.0434 (18)0.0413 (18)0.0370 (18)0.0046 (14)0.0180 (14)0.0120 (15)
O80.065 (2)0.067 (2)0.0429 (18)0.0176 (17)0.0156 (15)0.0153 (16)
N20.052 (2)0.058 (2)0.047 (2)0.0166 (18)0.0068 (17)0.0286 (18)
C80.036 (2)0.049 (2)0.035 (2)0.0047 (18)0.0078 (17)0.0174 (18)
C50.050 (2)0.035 (2)0.052 (3)0.0025 (18)0.019 (2)0.008 (2)
N40.074 (3)0.046 (3)0.078 (3)0.002 (2)0.003 (3)0.023 (3)
C380.053 (2)0.048 (2)0.036 (2)0.0126 (19)0.0121 (18)0.0133 (19)
C70.045 (2)0.055 (3)0.053 (3)0.002 (2)0.016 (2)0.026 (2)
N10.103 (4)0.048 (3)0.068 (3)0.009 (3)0.030 (3)0.011 (2)
O30.090 (3)0.072 (2)0.066 (2)0.031 (2)0.0143 (19)0.0379 (19)
C360.053 (3)0.047 (2)0.038 (2)0.001 (2)0.017 (2)0.001 (2)
N50.055 (2)0.066 (3)0.049 (2)0.0038 (19)0.0124 (19)0.005 (2)
C100.041 (2)0.071 (3)0.055 (3)0.004 (2)0.015 (2)0.032 (2)
C190.055 (3)0.075 (3)0.045 (3)0.017 (2)0.004 (2)0.035 (2)
C90.052 (2)0.053 (3)0.039 (2)0.0063 (19)0.0105 (19)0.022 (2)
C480.096 (4)0.059 (3)0.046 (3)0.002 (3)0.026 (3)0.009 (2)
O60.156 (5)0.068 (3)0.106 (4)0.017 (3)0.014 (3)0.051 (3)
C390.057 (3)0.050 (3)0.068 (3)0.003 (2)0.032 (2)0.014 (2)
C200.046 (3)0.100 (4)0.048 (3)0.020 (3)0.013 (2)0.025 (3)
C430.062 (3)0.067 (3)0.060 (3)0.021 (2)0.005 (2)0.023 (3)
C160.052 (3)0.076 (3)0.046 (3)0.002 (2)0.006 (2)0.027 (3)
C130.078 (4)0.084 (4)0.071 (4)0.014 (3)0.015 (3)0.049 (3)
O20.171 (5)0.059 (3)0.111 (4)0.029 (3)0.039 (4)0.017 (3)
C490.069 (3)0.110 (5)0.047 (3)0.012 (3)0.007 (3)0.004 (3)
C140.061 (3)0.093 (4)0.065 (3)0.032 (3)0.001 (2)0.041 (3)
O50.142 (4)0.057 (3)0.115 (4)0.024 (3)0.024 (3)0.030 (3)
O10.154 (4)0.075 (3)0.057 (3)0.028 (3)0.009 (3)0.003 (2)
C420.115 (5)0.043 (3)0.066 (4)0.019 (3)0.029 (3)0.012 (3)
C230.085 (4)0.122 (5)0.048 (3)0.045 (4)0.002 (3)0.033 (3)
C240.046 (3)0.119 (5)0.062 (3)0.024 (3)0.004 (2)0.038 (3)
C550.098 (4)0.060 (3)0.056 (3)0.014 (3)0.011 (3)0.001 (3)
C400.140 (6)0.050 (3)0.098 (5)0.010 (3)0.082 (5)0.010 (3)
C450.085 (4)0.055 (3)0.067 (3)0.021 (3)0.033 (3)0.031 (3)
C250.044 (3)0.155 (7)0.090 (5)0.013 (3)0.017 (3)0.030 (5)
C520.136 (6)0.090 (5)0.061 (4)0.005 (4)0.053 (4)0.004 (4)
C440.037 (3)0.091 (4)0.147 (7)0.005 (3)0.012 (3)0.039 (4)
C110.114 (5)0.096 (5)0.080 (4)0.035 (4)0.023 (4)0.056 (4)
C170.089 (4)0.085 (4)0.056 (3)0.002 (3)0.014 (3)0.016 (3)
C150.042 (3)0.138 (6)0.091 (4)0.013 (3)0.004 (3)0.065 (4)
C260.072 (3)0.082 (4)0.056 (3)0.018 (3)0.017 (3)0.024 (3)
C210.106 (5)0.119 (6)0.057 (4)0.039 (4)0.023 (3)0.035 (4)
C470.099 (4)0.089 (4)0.070 (4)0.009 (3)0.023 (3)0.047 (3)
C180.085 (4)0.154 (7)0.058 (4)0.000 (4)0.005 (3)0.048 (4)
C220.129 (6)0.150 (7)0.047 (3)0.058 (5)0.012 (4)0.027 (4)
C410.172 (7)0.055 (4)0.082 (5)0.010 (4)0.063 (5)0.007 (3)
C270.133 (6)0.073 (4)0.072 (4)0.013 (4)0.032 (4)0.026 (3)
C120.139 (6)0.078 (4)0.093 (5)0.005 (4)0.020 (4)0.054 (4)
C460.129 (7)0.104 (6)0.155 (8)0.052 (5)0.062 (6)0.083 (6)
C510.256 (12)0.103 (6)0.052 (4)0.054 (7)0.052 (6)0.027 (4)
C280.137 (7)0.116 (6)0.095 (6)0.026 (5)0.059 (5)0.003 (5)
C530.147 (7)0.103 (5)0.087 (5)0.052 (5)0.065 (5)0.010 (4)
C560.217 (10)0.085 (5)0.079 (5)0.045 (6)0.022 (6)0.025 (4)
C540.101 (6)0.237 (11)0.095 (6)0.098 (7)0.024 (5)0.010 (7)
C350.038 (2)0.052 (3)0.047 (2)0.0126 (19)0.0033 (18)0.023 (2)
C570.274 (14)0.112 (7)0.088 (6)0.091 (8)0.025 (8)0.015 (5)
C500.146 (7)0.170 (9)0.060 (5)0.049 (7)0.009 (5)0.018 (5)
Cl20.201 (5)0.82 (2)0.249 (7)0.106 (9)0.013 (5)0.207 (11)
Cl10.445 (12)0.220 (6)0.561 (16)0.012 (7)0.333 (12)0.022 (8)
C290.50 (3)0.163 (12)0.243 (19)0.050 (16)0.25 (2)0.111 (13)
Geometric parameters (Å, º) top
C3—C41.383 (6)C19—C201.566 (7)
C3—C21.401 (5)C19—C241.539 (7)
C3—C81.489 (6)C9—C141.550 (6)
O7—C371.245 (5)C48—C491.533 (8)
C37—C301.489 (6)C48—C531.563 (9)
C37—N61.330 (5)C39—C401.538 (8)
N3—C81.342 (5)C39—C451.551 (8)
N3—C91.467 (6)C39—C441.522 (8)
C31—C301.386 (6)C20—C251.508 (8)
C31—C321.388 (6)C20—C261.551 (8)
C4—C51.389 (6)C20—C211.543 (8)
C30—C351.388 (6)C43—C421.516 (8)
C32—C331.379 (6)C16—C131.528 (8)
C32—C361.503 (7)C16—C171.522 (8)
C1—C21.378 (6)C16—C181.555 (7)
C1—C61.401 (6)C13—C141.521 (7)
C1—C71.497 (6)C13—C121.521 (9)
C6—C51.366 (7)C49—C551.563 (8)
C33—C341.388 (7)C49—C541.525 (10)
C34—N41.453 (6)C49—C501.543 (10)
C34—C351.382 (6)C42—C451.525 (8)
O4—C81.228 (5)C42—C411.527 (9)
N6—C381.456 (5)C23—C241.511 (9)
O8—C361.231 (5)C23—C261.510 (9)
N2—C71.323 (6)C23—C221.540 (9)
N2—C191.458 (6)C55—C521.489 (10)
C5—N11.494 (6)C55—C561.521 (10)
N4—O61.209 (7)C55—C571.555 (9)
N4—O51.218 (6)C40—C411.522 (10)
C38—C391.557 (6)C45—C471.531 (8)
C38—C431.545 (6)C45—C461.525 (8)
C7—O31.236 (5)C52—C511.504 (11)
N1—O21.213 (6)C52—C531.536 (9)
N1—O11.234 (7)C11—C121.520 (10)
C36—N51.335 (6)C26—C271.550 (9)
N5—C481.453 (7)C26—C281.544 (9)
C10—C91.556 (6)C21—C221.542 (9)
C10—C161.536 (7)C51—C501.489 (13)
C10—C111.554 (8)Cl2—C291.651 (9)
C10—C151.523 (7)Cl1—C291.693 (9)
C2—C3—C4119.1 (4)C44—C39—C38114.5 (4)
C8—C3—C4122.2 (4)C44—C39—C40114.7 (5)
C8—C3—C2118.5 (4)C44—C39—C45118.6 (5)
C30—C37—O7119.9 (4)C25—C20—C19115.1 (4)
N6—C37—O7122.9 (4)C26—C20—C19102.7 (4)
N6—C37—C30117.2 (4)C26—C20—C25118.7 (5)
C9—N3—C8121.0 (3)C21—C20—C19103.0 (5)
C32—C31—C30121.6 (4)C21—C20—C25114.2 (5)
C5—C4—C3117.6 (4)C21—C20—C26100.9 (4)
C31—C30—C37121.2 (4)C42—C43—C38103.2 (4)
C35—C30—C37119.8 (4)C13—C16—C1093.8 (4)
C35—C30—C31118.9 (4)C17—C16—C10115.8 (4)
C33—C32—C31119.7 (4)C17—C16—C13115.5 (4)
C36—C32—C31117.3 (4)C18—C16—C10113.4 (4)
C36—C32—C33122.9 (4)C18—C16—C13112.2 (5)
C6—C1—C2118.8 (4)C18—C16—C17106.2 (5)
C7—C1—C2122.2 (4)C14—C13—C16101.6 (4)
C7—C1—C6118.5 (4)C12—C13—C16104.3 (5)
C1—C2—C3122.2 (4)C12—C13—C14108.2 (5)
C5—C6—C1118.1 (4)C55—C49—C48102.8 (4)
C34—C33—C32118.4 (4)C54—C49—C48112.1 (5)
N4—C34—C33118.1 (4)C54—C49—C55121.3 (7)
C35—C34—C33122.3 (4)C50—C49—C48103.4 (6)
C35—C34—N4119.5 (4)C50—C49—C5599.5 (5)
C38—N6—C37123.0 (3)C50—C49—C54115.4 (7)
C19—N2—C7123.9 (4)C13—C14—C9102.8 (4)
N3—C8—C3117.5 (3)C45—C42—C43102.1 (4)
O4—C8—C3119.4 (4)C41—C42—C43108.6 (5)
O4—C8—N3123.2 (4)C41—C42—C45102.8 (5)
C6—C5—C4124.2 (4)C26—C23—C24102.9 (4)
N1—C5—C4117.1 (4)C22—C23—C24106.3 (6)
N1—C5—C6118.6 (4)C22—C23—C26103.1 (5)
O6—N4—C34117.9 (5)C23—C24—C19104.3 (4)
O5—N4—C34118.8 (5)C52—C55—C4993.5 (5)
O5—N4—O6123.3 (5)C56—C55—C49114.3 (5)
C39—C38—N6116.0 (4)C56—C55—C52116.3 (7)
C43—C38—N6112.9 (4)C57—C55—C49114.5 (6)
C43—C38—C39102.7 (4)C57—C55—C52112.0 (6)
N2—C7—C1117.2 (4)C57—C55—C56106.3 (6)
O3—C7—C1118.8 (4)C41—C40—C39104.4 (5)
O3—C7—N2124.0 (4)C42—C45—C3993.6 (4)
O2—N1—C5116.3 (5)C47—C45—C39114.4 (5)
O1—N1—C5116.7 (5)C47—C45—C42115.7 (5)
O1—N1—O2126.9 (5)C46—C45—C39113.7 (5)
O8—C36—C32118.8 (4)C46—C45—C42111.9 (6)
N5—C36—C32117.4 (4)C46—C45—C47107.3 (5)
N5—C36—O8123.7 (4)C51—C52—C55105.2 (7)
C48—N5—C36121.6 (4)C53—C52—C55102.2 (5)
C16—C10—C9103.6 (3)C53—C52—C51108.0 (7)
C11—C10—C9101.2 (4)C12—C11—C10104.7 (5)
C11—C10—C16101.2 (4)C23—C26—C2094.5 (5)
C15—C10—C9114.5 (4)C27—C26—C20114.2 (5)
C15—C10—C16118.8 (5)C27—C26—C23113.7 (5)
C15—C10—C11115.1 (5)C28—C26—C20114.4 (5)
C20—C19—N2115.8 (4)C28—C26—C23114.1 (5)
C24—C19—N2115.0 (4)C28—C26—C27106.0 (6)
C24—C19—C20102.2 (4)C22—C21—C20104.1 (5)
C10—C9—N3116.5 (4)C21—C22—C23102.4 (5)
C14—C9—N3111.7 (4)C40—C41—C42102.8 (5)
C14—C9—C10102.5 (4)C11—C12—C13102.2 (5)
C49—C48—N5117.2 (5)C50—C51—C52102.5 (6)
C53—C48—N5112.3 (5)C52—C53—C48101.6 (5)
C53—C48—C49103.0 (4)C34—C35—C30118.9 (4)
C40—C39—C38102.9 (5)C51—C50—C49105.4 (6)
C45—C39—C38103.1 (4)Cl1—C29—Cl2110.8 (6)
C45—C39—C40100.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O70.86 (1)2.07 (1)2.881 (5)158 (1)
N3—H3···O80.86 (1)2.21 (1)3.047 (5)165 (1)
N6—H6A···O4i0.86 (1)2.13 (1)2.970 (4)165 (1)
C17—H17B···O80.96 (2)2.55 (3)3.445 (8)156 (2)
C17—H17B···N30.96 (2)2.55 (1)3.260 (7)131 (2)
C24—H24B···Cl1ii0.97 (1)2.77 (1)3.388 (8)123 (1)
C27—H27B···O70.96 (4)2.56 (4)3.491 (8)164 (2)
C27—H27B···N20.96 (4)2.60 (3)3.218 (8)122 (3)
C29—H29A···O6iii0.97 (2)2.49 (1)3.229 (14)133 (1)
C29—H29B···O3iv0.97 (2)2.41 (1)3.046 (14)123 (1)
C44—H44B···N60.96 (3)2.62 (3)2.940 (7)100 (2)
C47—H47B···O4i0.96 (3)2.42 (3)3.331 (8)158 (1)
C50—H50B···Cl20.97 (1)2.72 (1)3.617 (9)154 (1)
Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z1; (iii) x1, y, z+1; (iv) x, y, z+1.
 

Acknowledgements

The authors thank the DST–PURSE Single Crystal X-ray Diffraction Facility at the Faculty of Science, The Maharaja Sayajirao University of Baroda, Vadodara. JK thanks Apicore Pharmaceuticals Pvt Ltd for providing the infrastructure.

Funding information

Funding for this research was provided by: Department of Science and Technology, Ministry of Science and Technology .

References

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