Crystal structure of quinolinium 2-carboxy-6-nitro­benzoate monohydrate

Mohana, J.; Divya Bharathi, M.; Ahila, G.; Chakkaravarthi, G.; Anbalagan, G.

doi:10.1107/S2056989015006052

organic compounds

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ISSN: 2056-9890

Volume 71| Part 5| May 2015| Pages o270-o271

https://doi.org/10.1107/S2056989015006052

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Crystal structure of quinolinium 2-carboxy-6-nitrobenzoate monohydrate

J. Mohana,^a M. Divya Bharathi,^a G. Ahila,^a G. Chakkaravarthi ^b ^* and G. Anbalagan ^a ^*

^aDepartment of Physics, Presidency College, Chennai 600 005, India, and ^bDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com, anbu24663@yahoo.co.in

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 22 March 2015; accepted 25 March 2015; online 2 April 2015)

In the anion of the title hydrated molecular salt, C₉H₈N⁺·C₈H₄NO₆⁻·H₂O, the protonated carboxyl and nitro groups makes dihedral angles of 27.56 (5) and 6.86 (8)°, respectively, with the attached benzene ring, whereas the deprotonated carboxy group is almost orthogonal to it with a dihedral angle of 80.21 (1)°. In the crystal, the components are linked by O—H⋯O and N—H⋯O hydrogen bonds, generating [001] chains. The packing is consolidated by weak C—H⋯N and C—H⋯O interactions as well as aromatic π–π stacking [centroid-to-centroid distances: 3.7023 (8) & 3.6590 (9)Å] interactions, resulting in a three-dimensional network.

Keywords: crystal structure; molecular salt; quinolinium; 2-carboxy-6-nitrobenzoate; hydrogen bonding; π–π stacking interactions.

CCDC reference: 1015219

1. Related literature

For the biological activity of quinoline derivatives, see: Font et al. (1997 ); Sloboda et al. (1991 ). For similar structures, see: Castañeda et al. (2014 ); Kafka et al. (2012 ); Li & Chai (2007 ); Divya Bharathi et al. (2015 ).

2. Experimental

2.1. Crystal data

C₉H₈N⁺·C₈H₄NO₆⁻·H₂O
M_r = 358.30
Monoclinic, P 2₁ /c
a = 14.7622 (8) Å
b = 14.2461 (8) Å
c = 7.6395 (4) Å
β = 104.434 (2)°
V = 1555.90 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 295 K
0.26 × 0.24 × 0.18 mm

2.2. Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.969, T_max = 0.979
32650 measured reflections
4728 independent reflections
3394 reflections with I > 2σ(I)
R_int = 0.025

2.3. Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.115
S = 1.04
4728 reflections
248 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7A⋯O4	0.83 (1)	1.92 (1)	2.7416 (14)	171 (19)
O7—H7B⋯O4ⁱ	0.84 (1)	2.02 (1)	2.8459 (14)	169 (18)
O1—H1A⋯O7ⁱⁱ	0.84 (1)	1.75 (1)	2.5818 (14)	173 (2)
N2—H2A⋯O3ⁱⁱⁱ	0.91 (1)	1.74 (1)	2.6425 (14)	176 (18)
C16—H16⋯O4ⁱⁱⁱ	0.93	2.49	3.1166 (17)	125
C16—H16⋯O2^iv	0.93	2.39	3.1278 (17)	136
C12—H12⋯N1	0.93	2.61	3.4866 (19)	157
Symmetry codes: (i) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x, y, z+1; (iii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) -x+2, -y, -z+1.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 1015219

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015006052/hb7390sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015006052/hb7390Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015006052/hb7390Isup3.cml

checkCIF report

Chemical context top

The quinoline derivatives are known to exhibit wide range of pharmacological activities such as antibacterial (Benzerka, et al.2012), anti-viral (Font et al., 1997) and anti-inflammatory (Sloboda et al., 1991). In view of the above importance, we have synthesized the title compound and report herein on its crystal structure.

Structural commentary top

The ORTEP diagram of the title compound (I) is shown in Fig.1. The asymmetric unit of the title compound consists of C₉ H₈ N⁺ cation, C₈ H₄ N O₆^- anion and a water molecule. The geometric parameters of (I) (Fig. 1) are well agreed with the similar reported structures [Castañeda et al., 2014; Kafka et al., 2012; Li & Chai (2007)].

The quinolinium ring system is planar [r.m.s deviation = 0.0133 (12)Å] and protonated at N2 atom. In the anion, the carboxyl (O1/C7/O2), nitro (O5/N1/O6) and carboxy (O3/C8/O4) groups are inclined at an angle of 27.56 (5), 6.86 (8) and 80.21 (1)°, respectively with the attached benzene ring (C1—C6). The dihedral angle between the quinolinium ring system and benzene ring is 89.91 (5)°.

Supramolecular features top

The molecular structure is stabilized by weak intramolecular O—H···O and C—H···N hydrogen bonds (Table 1). The crystal structure is stabilized by weak intermolecular N—H···O, O—H···O and C—H···O hydrogen bonds (Table 1 & Fig. 2) which link adjacent anions and cations through water molecules into infinite one-dimensional chains along [001]. The crystal structure is further stabilized by weak π···π [Cg1···Cg1ⁱ = 3.7023 (8); Cg3···Cg2ⁱⁱ = 3.6590 (9)Å; (i) 1-x,-y,-z; (ii) x,1/2-y,-1/2+z; Cg1, Cg2 and Cg3 are the centroids of the rings (C1—C6), (C13/C14/C15/C16/c17/N2) and (C9—C13/c17), respectively] interactions.

Synthesis and crystallization top

Quinoline (3.22 g, 0.99 mol) was dissolved in hot water (25 ml) and after half an hour, a solution of 3-nitrophthalic acid (5.278 g, 0.38 mol) in methanol (25 ml) was added and stirred for about one hour. A white colour powder was formed. The product was dissolved in aqueous methanol solution (210 ml). Single crystals suitable for X-ray diffraction were obtained from the slow evaporation method at room temperature within a few days.

Refinement top

C-bound H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). H atoms for O atoms were located from Fourier map and refined with Uiso(H) = 1.5 Ueq(O). Distance restraints were applied for the distance O—H = 0.82 (1)Å. H atom for N atom was located from Fourier map and refined freely with distance restraint N—H = 0.88 (1)Å.

Related literature top

For the biological activity of quinoline derivatives, see: Font et al. (1997); Sloboda et al. (1991). For similar structures, see: Castañeda et al. (2014); Kafka et al. (2012); Li & Chai (2007); Divya Bharathi et al. (2015).

Structure description top

For the biological activity of quinoline derivatives, see: Font et al. (1997); Sloboda et al. (1991). For similar structures, see: Castañeda et al. (2014); Kafka et al. (2012); Li & Chai (2007); Divya Bharathi et al. (2015).

Synthesis and crystallization top

Refinement details top

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: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of (I), viewed down C face. Intermolecular Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

Quinolinium 2-carboxy-6-nitrobenzoate monohydrate top

Crystal data top

C₉H₈N⁺·C₈H₄NO₆⁻·H₂O	F(000) = 744
M_r = 358.30	D_x = 1.530 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9970 reflections
a = 14.7622 (8) Å	θ = 2.8–30.4°
b = 14.2461 (8) Å	µ = 0.12 mm⁻¹
c = 7.6395 (4) Å	T = 295 K
β = 104.434 (2)°	Block, colourless
V = 1555.90 (15) Å³	0.26 × 0.24 × 0.18 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	4728 independent reflections
Radiation source: fine-focus sealed tube	3394 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω and φ scans	θ_max = 30.8°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −21→21
T_min = 0.969, T_max = 0.979	k = −20→20
32650 measured reflections	l = −10→9

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0472P)² + 0.4484P] where P = (F_o² + 2F_c²)/3
4728 reflections	(Δ/σ)_max < 0.001
248 parameters	Δρ_max = 0.29 e Å⁻³
4 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₉H₈N⁺·C₈H₄NO₆⁻·H₂O	V = 1555.90 (15) Å³
M_r = 358.30	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.7622 (8) Å	µ = 0.12 mm⁻¹
b = 14.2461 (8) Å	T = 295 K
c = 7.6395 (4) Å	0.26 × 0.24 × 0.18 mm
β = 104.434 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4728 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	3394 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.979	R_int = 0.025
32650 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	4 restraints
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.29 e Å⁻³
4728 reflections	Δρ_min = −0.20 e Å⁻³
248 parameters

Special details top

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
C1	0.64273 (8)	0.07483 (8)	−0.05905 (16)	0.0309 (2)
C2	0.57907 (9)	0.14414 (9)	−0.04652 (19)	0.0386 (3)
H2	0.5629	0.1900	−0.1354	0.046*
C3	0.54012 (9)	0.14429 (9)	0.09892 (19)	0.0405 (3)
H3	0.4982	0.1912	0.1106	0.049*
C4	0.56333 (9)	0.07465 (9)	0.22753 (18)	0.0361 (3)
H4	0.5351	0.0735	0.3236	0.043*
C5	0.62851 (8)	0.00608 (8)	0.21529 (16)	0.0295 (2)
C6	0.67125 (8)	0.00565 (8)	0.07151 (15)	0.0276 (2)
C7	0.65254 (8)	−0.06752 (8)	0.35872 (16)	0.0321 (2)
C8	0.74316 (8)	−0.06939 (8)	0.06354 (16)	0.0305 (2)
C9	0.95815 (10)	0.39076 (10)	0.1010 (2)	0.0450 (3)
H9	0.9905	0.4451	0.1463	0.054*
C10	0.87001 (11)	0.39591 (13)	−0.0086 (2)	0.0563 (4)
H10	0.8421	0.4543	−0.0379	0.068*
C11	0.82119 (11)	0.31475 (15)	−0.0772 (2)	0.0617 (5)
H11	0.7610	0.3196	−0.1515	0.074*
C12	0.86022 (10)	0.22927 (13)	−0.0373 (2)	0.0552 (4)
H12	0.8268	0.1759	−0.0848	0.066*
C13	0.95129 (9)	0.22011 (10)	0.07584 (19)	0.0387 (3)
C14	0.99619 (11)	0.13384 (10)	0.1225 (2)	0.0488 (4)
H14	0.9653	0.0784	0.0797	0.059*
C15	1.08465 (11)	0.13063 (10)	0.2302 (2)	0.0497 (4)
H15	1.1152	0.0734	0.2584	0.060*
C16	1.12878 (9)	0.21365 (10)	0.2974 (2)	0.0429 (3)
H16	1.1887	0.2117	0.3734	0.051*
C17	0.99937 (8)	0.30253 (9)	0.14427 (17)	0.0331 (3)
N1	0.67819 (8)	0.07495 (8)	−0.22213 (15)	0.0389 (3)
H2A	1.1177 (11)	0.3480 (9)	0.304 (2)	0.060 (5)*
N2	1.08727 (7)	0.29511 (8)	0.25544 (16)	0.0364 (2)
O1	0.58421 (7)	−0.08353 (8)	0.43610 (14)	0.0457 (2)
H1A	0.6007 (14)	−0.1247 (11)	0.516 (2)	0.069*
O2	0.72664 (7)	−0.10794 (7)	0.39726 (13)	0.0445 (2)
O3	0.82733 (6)	−0.04668 (7)	0.11938 (14)	0.0408 (2)
O4	0.71315 (7)	−0.14892 (6)	0.01135 (13)	0.0386 (2)
O5	0.65803 (10)	0.14023 (9)	−0.32691 (17)	0.0659 (4)
O6	0.72700 (9)	0.01019 (9)	−0.24593 (16)	0.0611 (3)
O7	0.62094 (7)	−0.21451 (7)	−0.32298 (13)	0.0420 (2)
H7A	0.6537 (12)	−0.1934 (13)	−0.2261 (17)	0.063*
H7B	0.6482 (12)	−0.2591 (10)	−0.359 (2)	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0293 (5)	0.0308 (6)	0.0300 (6)	−0.0029 (4)	0.0026 (4)	0.0001 (4)
C2	0.0368 (6)	0.0332 (6)	0.0406 (7)	0.0043 (5)	0.0001 (5)	0.0069 (5)
C3	0.0350 (6)	0.0363 (7)	0.0469 (8)	0.0107 (5)	0.0042 (5)	−0.0002 (5)
C4	0.0322 (6)	0.0386 (6)	0.0368 (6)	0.0049 (5)	0.0073 (5)	−0.0027 (5)
C5	0.0273 (5)	0.0287 (5)	0.0296 (6)	0.0008 (4)	0.0014 (4)	−0.0015 (4)
C6	0.0245 (5)	0.0256 (5)	0.0300 (6)	−0.0016 (4)	0.0017 (4)	−0.0027 (4)
C7	0.0341 (6)	0.0325 (6)	0.0281 (6)	0.0010 (5)	0.0047 (5)	−0.0021 (5)
C8	0.0328 (6)	0.0293 (5)	0.0290 (6)	0.0023 (4)	0.0068 (4)	−0.0014 (4)
C9	0.0443 (7)	0.0386 (7)	0.0511 (8)	0.0053 (6)	0.0100 (6)	0.0017 (6)
C10	0.0489 (9)	0.0593 (10)	0.0580 (10)	0.0201 (7)	0.0085 (7)	0.0066 (8)
C11	0.0353 (7)	0.0846 (13)	0.0584 (10)	0.0099 (8)	−0.0011 (7)	−0.0028 (9)
C12	0.0359 (7)	0.0647 (10)	0.0604 (10)	−0.0080 (7)	0.0031 (7)	−0.0138 (8)
C13	0.0316 (6)	0.0414 (7)	0.0437 (7)	−0.0041 (5)	0.0105 (5)	−0.0058 (6)
C14	0.0479 (8)	0.0350 (7)	0.0644 (10)	−0.0077 (6)	0.0157 (7)	−0.0050 (6)
C15	0.0469 (8)	0.0350 (7)	0.0684 (10)	0.0049 (6)	0.0166 (7)	0.0093 (7)
C16	0.0311 (6)	0.0444 (7)	0.0519 (8)	0.0019 (5)	0.0080 (6)	0.0107 (6)
C17	0.0282 (5)	0.0364 (6)	0.0355 (6)	−0.0006 (5)	0.0094 (5)	0.0014 (5)
N1	0.0401 (6)	0.0412 (6)	0.0338 (6)	−0.0060 (5)	0.0061 (5)	0.0015 (5)
N2	0.0289 (5)	0.0362 (5)	0.0429 (6)	−0.0049 (4)	0.0068 (4)	0.0021 (5)
O1	0.0425 (5)	0.0521 (6)	0.0446 (6)	0.0056 (4)	0.0148 (4)	0.0143 (4)
O2	0.0439 (5)	0.0486 (6)	0.0404 (5)	0.0147 (4)	0.0095 (4)	0.0113 (4)
O3	0.0286 (4)	0.0385 (5)	0.0539 (6)	0.0020 (4)	0.0078 (4)	−0.0039 (4)
O4	0.0459 (5)	0.0293 (4)	0.0388 (5)	0.0001 (4)	0.0071 (4)	−0.0059 (4)
O5	0.0789 (9)	0.0694 (8)	0.0530 (7)	0.0109 (6)	0.0232 (6)	0.0290 (6)
O6	0.0824 (9)	0.0594 (7)	0.0506 (6)	0.0141 (6)	0.0338 (6)	0.0025 (5)
O7	0.0478 (6)	0.0417 (5)	0.0355 (5)	0.0014 (4)	0.0086 (4)	0.0010 (4)

Geometric parameters (Å, º) top

C1—C2	1.3828 (17)	C10—H10	0.9300
C1—C6	1.3907 (16)	C11—C12	1.349 (3)
C1—N1	1.4666 (16)	C11—H11	0.9300
C2—C3	1.372 (2)	C12—C13	1.4114 (19)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.3780 (19)	C13—C14	1.400 (2)
C3—H3	0.9300	C13—C17	1.4039 (18)
C4—C5	1.3906 (16)	C14—C15	1.360 (2)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.3965 (17)	C15—C16	1.386 (2)
C5—C7	1.4940 (16)	C15—H15	0.9300
C6—C8	1.5184 (16)	C16—N2	1.3141 (17)
C7—O2	1.2060 (15)	C16—H16	0.9300
C7—O1	1.3101 (16)	C17—N2	1.3663 (16)
C8—O4	1.2453 (14)	N1—O6	1.2120 (16)
C8—O3	1.2516 (14)	N1—O5	1.2146 (15)
C9—C10	1.362 (2)	N2—H2A	0.908 (9)
C9—C17	1.3996 (19)	O1—H1A	0.840 (9)
C9—H9	0.9300	O7—H7A	0.833 (9)
C10—C11	1.394 (3)	O7—H7B	0.836 (9)

C2—C1—C6	123.08 (12)	C12—C11—C10	120.79 (14)
C2—C1—N1	116.78 (11)	C12—C11—H11	119.6
C6—C1—N1	120.12 (11)	C10—C11—H11	119.6
C3—C2—C1	119.09 (12)	C11—C12—C13	120.66 (15)
C3—C2—H2	120.5	C11—C12—H12	119.7
C1—C2—H2	120.5	C13—C12—H12	119.7
C2—C3—C4	119.75 (12)	C14—C13—C17	118.44 (12)
C2—C3—H3	120.1	C14—C13—C12	123.75 (13)
C4—C3—H3	120.1	C17—C13—C12	117.82 (13)
C3—C4—C5	120.73 (12)	C15—C14—C13	120.41 (13)
C3—C4—H4	119.6	C15—C14—H14	119.8
C5—C4—H4	119.6	C13—C14—H14	119.8
C4—C5—C6	120.78 (11)	C14—C15—C16	119.16 (13)
C4—C5—C7	119.05 (11)	C14—C15—H15	120.4
C6—C5—C7	120.17 (10)	C16—C15—H15	120.4
C1—C6—C5	116.47 (10)	N2—C16—C15	121.06 (12)
C1—C6—C8	124.05 (11)	N2—C16—H16	119.5
C5—C6—C8	119.47 (10)	C15—C16—H16	119.5
O2—C7—O1	124.07 (12)	N2—C17—C9	120.40 (12)
O2—C7—C5	123.32 (11)	N2—C17—C13	118.71 (11)
O1—C7—C5	112.60 (10)	C9—C17—C13	120.89 (12)
O4—C8—O3	126.02 (11)	O6—N1—O5	122.75 (13)
O4—C8—C6	117.19 (10)	O6—N1—C1	118.55 (11)
O3—C8—C6	116.67 (10)	O5—N1—C1	118.69 (12)
C10—C9—C17	119.08 (14)	C16—N2—C17	122.19 (11)
C10—C9—H9	120.5	C16—N2—H2A	118.7 (12)
C17—C9—H9	120.5	C17—N2—H2A	119.1 (12)
C9—C10—C11	120.77 (15)	C7—O1—H1A	109.7 (14)
C9—C10—H10	119.6	H7A—O7—H7B	110.4 (18)
C11—C10—H10	119.6

C6—C1—C2—C3	−1.47 (19)	C17—C9—C10—C11	−0.1 (3)
N1—C1—C2—C3	176.70 (11)	C9—C10—C11—C12	−0.2 (3)
C1—C2—C3—C4	−1.4 (2)	C10—C11—C12—C13	0.3 (3)
C2—C3—C4—C5	2.4 (2)	C11—C12—C13—C14	−179.82 (16)
C3—C4—C5—C6	−0.64 (18)	C11—C12—C13—C17	−0.1 (2)
C3—C4—C5—C7	179.28 (12)	C17—C13—C14—C15	−0.7 (2)
C2—C1—C6—C5	3.15 (17)	C12—C13—C14—C15	179.01 (16)
N1—C1—C6—C5	−174.97 (10)	C13—C14—C15—C16	1.9 (2)
C2—C1—C6—C8	−178.10 (11)	C14—C15—C16—N2	−1.5 (2)
N1—C1—C6—C8	3.78 (17)	C10—C9—C17—N2	−179.26 (14)
C4—C5—C6—C1	−2.06 (16)	C10—C9—C17—C13	0.3 (2)
C7—C5—C6—C1	178.02 (10)	C14—C13—C17—N2	−0.92 (19)
C4—C5—C6—C8	179.13 (11)	C12—C13—C17—N2	179.37 (13)
C7—C5—C6—C8	−0.78 (16)	C14—C13—C17—C9	179.54 (14)
C4—C5—C7—O2	−153.38 (13)	C12—C13—C17—C9	−0.2 (2)
C6—C5—C7—O2	26.54 (18)	C2—C1—N1—O6	−173.03 (12)
C4—C5—C7—O1	27.15 (16)	C6—C1—N1—O6	5.20 (17)
C6—C5—C7—O1	−152.93 (11)	C2—C1—N1—O5	7.53 (17)
C1—C6—C8—O4	−100.90 (14)	C6—C1—N1—O5	−174.24 (12)
C5—C6—C8—O4	77.82 (14)	C15—C16—N2—C17	−0.1 (2)
C1—C6—C8—O3	82.81 (15)	C9—C17—N2—C16	−179.12 (13)
C5—C6—C8—O3	−98.48 (13)	C13—C17—N2—C16	1.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O4	0.83 (1)	1.92 (1)	2.7416 (14)	171 (19)
O7—H7B···O4ⁱ	0.84 (1)	2.02 (1)	2.8459 (14)	169 (18)
O1—H1A···O7ⁱⁱ	0.84 (1)	1.75 (1)	2.5818 (14)	173 (2)
N2—H2A···O3ⁱⁱⁱ	0.91 (1)	1.74 (1)	2.6425 (14)	176 (18)
C16—H16···O4ⁱⁱⁱ	0.93	2.49	3.1166 (17)	125
C16—H16···O2^iv	0.93	2.39	3.1278 (17)	136
C12—H12···N1	0.93	2.61	3.4866 (19)	157

Symmetry codes: (i) x, −y−1/2, z−1/2; (ii) x, y, z+1; (iii) −x+2, y+1/2, −z+1/2; (iv) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O4	0.833 (9)	1.915 (10)	2.7416 (14)	171 (19)
O7—H7B···O4ⁱ	0.836 (9)	2.021 (10)	2.8459 (14)	169 (18)
O1—H1A···O7ⁱⁱ	0.840 (9)	1.745 (10)	2.5818 (14)	173 (2)
N2—H2A···O3ⁱⁱⁱ	0.908 (9)	1.736 (9)	2.6425 (14)	176 (18)
C16—H16···O4ⁱⁱⁱ	0.93	2.49	3.1166 (17)	125
C16—H16···O2^iv	0.93	2.39	3.1278 (17)	136
C12—H12···N1	0.93	2.61	3.4866 (19)	157

Symmetry codes: (i) x, −y−1/2, z−1/2; (ii) x, y, z+1; (iii) −x+2, y+1/2, −z+1/2; (iv) −x+2, −y, −z+1.

Acknowledgements

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

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Volume 71| Part 5| May 2015| Pages o270-o271

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