Pyrrolidinium-2-carboxyl­ate–4-nitro­phenol (1/2)

Sowmya, N.S.; Vidyalakshmi, Y.; Sampathkrishnan, S.; Srinivasan, T.; Velmurugan, D.

doi:10.1107/S1600536813028742

organic compounds

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ISSN: 2056-9890

Volume 69| Part 11| November 2013| Page o1723

doi:10.1107/S1600536813028742

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Pyrrolidinium-2-carboxylate–4-nitrophenol (1/2)

Narayanan Swarna Sowmya,^a Yechuri Vidyalakshmi,^b Sadasivam Sampathkrishnan,^a Thothadri Srinivasan ^c and Devadasan Velmurugan ^c ^*

^aSri Venkateswara College of Engineering, Pennalur, Irungattukottai 602 117, Sriperumbudur Taluk, Tamilnadu, India, ^bDepartment of Physics, Anna University, Adyar, Chennai 600 025, Tamilnadu, India, and ^cCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: shirai2011@gmail.com

(Received 9 October 2013; accepted 19 October 2013; online 31 October 2013)

In the title compound, C₅H₉NO₂·2C₆H₅NO₃, the pyrrolidine ring of the pyrrolidinium-2-carboxylate zwitterion adopts a twisted conformation on the –CH₂—CH₂– bond adjacent to the N atom. The mean plane of this pyrrolidine ring forms dihedral angles of 25.3 (3) and 32.1 (3)° with the two nitrophenol rings. An intramolecular N—H⋯O hydrogen bond occurs in the pyrrolidinium-2-carboxylate molecule. In the crystal, molecules are linked via O—H⋯O and N—H⋯O hydrogen bonds, enclosing R³₂(8) ring motifs, forming chains running parallel to the a axis. These chains are further cross-linked by O—H⋯O and C—H⋯O hydrogen bonds, forming undulating two-dimensional networks lying parallel to (001).

CCDC reference: 954997

Related literature

For the use of nitro-aromatics as intermediates in explosives, dyestuffs, pesticides and organic synthesis, see: Yan et al. (2006 ). For the occurrence of nitro-aromatics in industrial wastes and as direct pollutants in the environment, see: Yan et al. (2006); Soojhawon et al. (2005 ). For ring puckering analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₅H₉NO₂·2C₆H₅NO₃
M_r = 393.35
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.9045 (3) Å
b = 15.6099 (7) Å
c = 20.0424 (9) Å
V = 1847.28 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.35 × 0.25 × 0.25 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.961, T_max = 0.972
17765 measured reflections
3572 independent reflections
2987 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.094
S = 1.06
3572 reflections
261 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O8	0.94 (6)	2.03 (6)	2.606 (6)	118 (5)
N3—H3B⋯O7ⁱ	0.93 (5)	1.87 (6)	2.766 (6)	160 (7)
O3—H3C⋯O7ⁱ	0.82	1.92	2.656 (5)	148
O6—H6A⋯O8ⁱⁱ	0.82	1.82	2.604 (5)	159
C11—H11⋯O1ⁱ	0.93	2.59	3.503 (8)	169
Symmetry codes: (i) x-1, y, z; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 954997

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813028742/su2657sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813028742/su2657Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813028742/su2657Isup3.cml

checkCIF report

Comment top

Nitro-aromatics are widely used either as materials or as intermediates in explosives, dyestuffs, pesticides and organic synthesis (Yan et al., 2006). They also occur as industrial wastes and direct pollutants in the environment. They are relatively soluble in water and detectable in rivers, ponds and soil (Yan et al., 2006; Soojhawon et al., 2005).

The title compound was synthesized by mixing eqimolar amounts of pyrrolidine carboxylic acid and para-nitrophenol in water. The crystals obtained were found to be composed of one molecule of pyrrolidinium-2-carboxylate, in the zwitterion form, and two molecules of para-nitrophenol, Fig. 1. The pyrrolidine ring (N3/C14-C17) adopts a twisted conformation on bond C17-C15, with puckering parameters (Cremer & Pople, 1975) q₂ = 0.373 (7) Å and ϕ₂ = 312.3 (11)°. The hydroxy group O atoms, O3 and O6, deviate slightly by -0.0380 (3) and 0.0160 (5) Å, respectively, from the mean planes of the benzene rings to which they are attached, (C1–C6) and (C7–C12).

The mean plane of the pyrrolidine ring (N3/C14-C17) forms dihedral angles of 25.3 (3)° and 32.1 (3)° with the nitro-phenol rings (C1-C6) and (C7-C12), respectively.

In the crystal, molecules are linked via O—H···O and N—H···O intra- and inter-molecular hydrogen bonds (Table 1 and Fig. 2), with R³₂(8) ring motifs, forming chains running parallel to the a axis. These chains are further cross-linked by O—H···O and C—H···O hydrogen bond forming undulating two-dimensional networks lying parallel to the ab plane (Table 1 and Fig. 2).

Related literature top

For the use of nitro-aromatics as intermediates in explosives, dyestuffs, pesticides and organic synthesis, see: Yan et al. (2006). For the occurrence of nitro-aromatics in industrial wastes and as direct pollutants in the environment, see: Yan et al. (2006); Soojhawon et al. (2005). For ring puckering analysis, see: Cremer & Pople (1975).

Experimental top

An equimolar (1:1:1) ratio of pyrrolidine carboxylic acid and para-nitrophenol were added to distilled water as solvent and the mixture stirred for 1 h, giving a clear solution. The solution was filtered into a clean beaker and sealed with parafilm and kept at room temperature for three days, after which block-like colourless crystals suitable for X-ray diffraction analysis were obtained.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound viewed along the c axis. The hydrogen bonds are shown as dashed lines (see Table 1 for details; H atoms not involved in hydrogen bonding have been excluded for clarity).

Pyrrolidinium-2-carboxylate–4-nitrophenol (1/2) top

Crystal data top

C₅H₉NO₂·2C₆H₅NO₃	F(000) = 824
M_r = 393.35	D_x = 1.414 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3572 reflections
a = 5.9045 (3) Å	θ = 2.4–25.9°
b = 15.6099 (7) Å	µ = 0.11 mm⁻¹
c = 20.0424 (9) Å	T = 293 K
V = 1847.28 (15) Å³	Block, colourless
Z = 4	0.35 × 0.25 × 0.25 mm

Data collection top

Bruker SMART APEXII area-detector diffractometer	3572 independent reflections
Radiation source: fine-focus sealed tube	2987 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω and ϕ scans	θ_max = 25.9°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −7→7
T_min = 0.961, T_max = 0.972	k = −17→19
17765 measured reflections	l = −23→24

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0434P)² + 0.2454P] where P = (F_o² + 2F_c²)/3
3572 reflections	(Δ/σ)_max < 0.001
261 parameters	Δρ_max = 0.23 e Å⁻³
2 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₅H₉NO₂·2C₆H₅NO₃	V = 1847.28 (15) Å³
M_r = 393.35	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.9045 (3) Å	µ = 0.11 mm⁻¹
b = 15.6099 (7) Å	T = 293 K
c = 20.0424 (9) Å	0.35 × 0.25 × 0.25 mm

Data collection top

Bruker SMART APEXII area-detector diffractometer	3572 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2987 reflections with I > 2σ(I)
T_min = 0.961, T_max = 0.972	R_int = 0.029
17765 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	2 restraints
wR(F²) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.23 e Å⁻³
3572 reflections	Δρ_min = −0.15 e Å⁻³
261 parameters

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.

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	0.7666 (9)	0.5876 (3)	0.5668 (3)	0.0468 (13)
C2	0.6897 (10)	0.5897 (3)	0.6313 (3)	0.0502 (13)
H2	0.7673	0.5610	0.6649	0.060*
C3	0.4946 (9)	0.6351 (3)	0.6455 (2)	0.0469 (12)
H3	0.4380	0.6362	0.6887	0.056*
C4	0.3835 (9)	0.6789 (3)	0.5951 (2)	0.0455 (12)
C5	0.4649 (11)	0.6750 (4)	0.5306 (3)	0.0556 (15)
H5	0.3892	0.7039	0.4967	0.067*
C6	0.6561 (11)	0.6291 (4)	0.5163 (3)	0.0552 (14)
H6	0.7103	0.6262	0.4728	0.066*
C7	0.7088 (10)	0.3784 (3)	0.4091 (3)	0.0491 (13)
C8	0.8784 (10)	0.3384 (4)	0.4433 (3)	0.0518 (14)
H8	1.0042	0.3175	0.4207	0.062*
C9	0.8621 (9)	0.3292 (3)	0.5114 (3)	0.0474 (12)
H9	0.9778	0.3028	0.5352	0.057*
C10	0.6715 (8)	0.3596 (3)	0.5440 (2)	0.0404 (11)
C11	0.5015 (10)	0.3997 (4)	0.5088 (3)	0.0508 (13)
H11	0.3744	0.4202	0.5311	0.061*
C12	0.5193 (11)	0.4094 (4)	0.4411 (3)	0.0549 (14)
H12	0.4051	0.4364	0.4171	0.066*
C13	1.0014 (8)	0.7956 (3)	0.7647 (2)	0.0421 (12)
C14	0.7877 (8)	0.8049 (3)	0.7237 (2)	0.0401 (12)
H14	0.7464	0.7489	0.7054	0.048*
C15	0.5588 (13)	0.9273 (4)	0.7485 (4)	0.0726 (19)
H15A	0.6620	0.9654	0.7718	0.087*
H15B	0.4042	0.9442	0.7583	0.087*
C16	0.8030 (11)	0.8693 (5)	0.6673 (3)	0.0729 (19)
H16A	0.9432	0.9014	0.6702	0.087*
H16B	0.7977	0.8404	0.6245	0.087*
C17	0.6028 (15)	0.9278 (5)	0.6752 (4)	0.094 (3)
H17A	0.6379	0.9851	0.6596	0.113*
H17B	0.4729	0.9063	0.6507	0.113*
N1	0.9739 (9)	0.5403 (3)	0.5517 (3)	0.0627 (13)
N2	0.7296 (12)	0.3891 (4)	0.3376 (3)	0.0710 (16)
N3	0.5998 (7)	0.8362 (3)	0.7673 (2)	0.0465 (11)
O1	1.0691 (9)	0.5029 (3)	0.5975 (3)	0.0833 (15)
O2	1.0428 (9)	0.5400 (3)	0.4942 (3)	0.0866 (15)
O3	0.1964 (7)	0.7261 (3)	0.60652 (19)	0.0642 (12)
H3C	0.1632	0.7234	0.6462	0.096*
O4	0.8932 (11)	0.3577 (4)	0.3096 (2)	0.0953 (18)
O5	0.5857 (13)	0.4289 (4)	0.3074 (3)	0.119 (2)
O6	0.6447 (6)	0.3513 (3)	0.61037 (16)	0.0571 (10)
H6A	0.7548	0.3265	0.6262	0.086*
O7	1.1759 (6)	0.7746 (3)	0.73339 (18)	0.0570 (10)
O8	0.9884 (7)	0.8096 (3)	0.82530 (17)	0.0648 (12)
H3A	0.653 (11)	0.832 (4)	0.811 (3)	0.064 (17)*
H3B	0.470 (11)	0.804 (5)	0.760 (4)	0.10 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.045 (3)	0.038 (3)	0.057 (3)	−0.005 (2)	0.004 (2)	−0.007 (3)
C2	0.050 (3)	0.046 (3)	0.055 (3)	−0.004 (3)	−0.008 (3)	0.004 (3)
C3	0.048 (3)	0.053 (3)	0.039 (3)	−0.003 (3)	0.002 (2)	0.001 (2)
C4	0.043 (3)	0.050 (3)	0.044 (3)	−0.002 (2)	−0.001 (2)	−0.003 (2)
C5	0.064 (4)	0.064 (4)	0.039 (3)	0.009 (3)	−0.001 (3)	0.001 (3)
C6	0.063 (4)	0.057 (3)	0.045 (3)	−0.001 (3)	0.010 (3)	−0.006 (3)
C7	0.067 (4)	0.046 (3)	0.034 (3)	−0.007 (3)	0.001 (2)	−0.002 (2)
C8	0.051 (3)	0.055 (3)	0.049 (3)	0.002 (3)	0.014 (3)	−0.008 (3)
C9	0.040 (3)	0.054 (3)	0.047 (3)	0.006 (2)	−0.002 (2)	−0.003 (3)
C10	0.037 (3)	0.049 (3)	0.036 (2)	−0.004 (2)	0.000 (2)	−0.004 (2)
C11	0.043 (3)	0.061 (3)	0.049 (3)	0.009 (3)	0.003 (2)	−0.001 (3)
C12	0.056 (4)	0.057 (3)	0.051 (3)	0.008 (3)	−0.013 (3)	0.006 (3)
C13	0.031 (2)	0.055 (3)	0.040 (3)	−0.002 (2)	0.003 (2)	−0.005 (2)
C14	0.028 (2)	0.057 (3)	0.035 (2)	0.001 (2)	0.0025 (19)	−0.005 (2)
C15	0.066 (4)	0.064 (4)	0.087 (5)	0.013 (3)	0.014 (4)	−0.005 (4)
C16	0.058 (4)	0.104 (5)	0.057 (4)	0.017 (4)	0.015 (3)	0.022 (4)
C17	0.076 (5)	0.103 (6)	0.104 (6)	0.025 (4)	0.020 (4)	0.046 (5)
N1	0.051 (3)	0.049 (3)	0.088 (4)	−0.005 (2)	0.006 (3)	−0.012 (3)
N2	0.103 (5)	0.067 (4)	0.042 (3)	−0.013 (3)	0.004 (3)	−0.001 (3)
N3	0.030 (2)	0.068 (3)	0.041 (2)	0.004 (2)	0.0055 (18)	0.002 (2)
O1	0.065 (3)	0.075 (3)	0.110 (4)	0.019 (2)	−0.008 (3)	−0.001 (3)
O2	0.074 (3)	0.092 (3)	0.094 (4)	0.011 (3)	0.028 (3)	−0.012 (3)
O3	0.055 (2)	0.089 (3)	0.048 (2)	0.022 (2)	0.0020 (19)	0.000 (2)
O4	0.135 (5)	0.101 (4)	0.050 (3)	−0.013 (4)	0.030 (3)	−0.009 (3)
O5	0.158 (6)	0.145 (6)	0.052 (3)	0.023 (5)	−0.014 (4)	0.028 (3)
O6	0.042 (2)	0.092 (3)	0.0365 (19)	0.003 (2)	0.0030 (16)	0.0015 (19)
O7	0.0301 (18)	0.089 (3)	0.052 (2)	0.0065 (19)	0.0028 (16)	−0.010 (2)
O8	0.042 (2)	0.113 (4)	0.039 (2)	0.005 (2)	−0.0036 (17)	−0.015 (2)

Geometric parameters (Å, º) top

C1—C6	1.368 (8)	C13—O8	1.237 (6)
C1—C2	1.369 (8)	C13—O7	1.250 (6)
C1—N1	1.461 (8)	C13—C14	1.512 (7)
C2—C3	1.382 (8)	C14—N3	1.493 (6)
C2—H2	0.9300	C14—C16	1.514 (8)
C3—C4	1.385 (7)	C14—H14	0.9800
C3—H3	0.9300	C15—N3	1.491 (8)
C4—O3	1.347 (6)	C15—C17	1.493 (11)
C4—C5	1.380 (7)	C15—H15A	0.9700
C5—C6	1.367 (8)	C15—H15B	0.9700
C5—H5	0.9300	C16—C17	1.502 (10)
C6—H6	0.9300	C16—H16A	0.9700
C7—C8	1.364 (8)	C16—H16B	0.9700
C7—C12	1.377 (8)	C17—H17A	0.9700
C7—N2	1.449 (7)	C17—H17B	0.9700
C8—C9	1.375 (7)	N1—O2	1.223 (7)
C8—H8	0.9300	N1—O1	1.225 (7)
C9—C10	1.385 (7)	N2—O5	1.213 (8)
C9—H9	0.9300	N2—O4	1.219 (8)
C10—O6	1.347 (6)	N3—H3A	0.94 (6)
C10—C11	1.377 (7)	N3—H3B	0.93 (5)
C11—C12	1.370 (7)	O3—H3C	0.8200
C11—H11	0.9300	O6—H6A	0.8200
C12—H12	0.9300

C6—C1—C2	121.9 (5)	N3—C14—C13	109.5 (4)
C6—C1—N1	119.0 (5)	N3—C14—C16	105.3 (4)
C2—C1—N1	119.0 (5)	C13—C14—C16	114.8 (5)
C1—C2—C3	118.8 (5)	N3—C14—H14	109.0
C1—C2—H2	120.6	C13—C14—H14	109.0
C3—C2—H2	120.6	C16—C14—H14	109.0
C2—C3—C4	119.9 (5)	N3—C15—C17	102.9 (5)
C2—C3—H3	120.1	N3—C15—H15A	111.2
C4—C3—H3	120.1	C17—C15—H15A	111.2
O3—C4—C5	118.0 (5)	N3—C15—H15B	111.2
O3—C4—C3	122.3 (5)	C17—C15—H15B	111.2
C5—C4—C3	119.8 (5)	H15A—C15—H15B	109.1
C6—C5—C4	120.4 (5)	C17—C16—C14	106.1 (5)
C6—C5—H5	119.8	C17—C16—H16A	110.5
C4—C5—H5	119.8	C14—C16—H16A	110.5
C5—C6—C1	119.1 (5)	C17—C16—H16B	110.5
C5—C6—H6	120.4	C14—C16—H16B	110.5
C1—C6—H6	120.4	H16A—C16—H16B	108.7
C8—C7—C12	121.6 (5)	C15—C17—C16	103.7 (6)
C8—C7—N2	119.2 (6)	C15—C17—H17A	111.0
C12—C7—N2	119.3 (6)	C16—C17—H17A	111.0
C7—C8—C9	119.7 (5)	C15—C17—H17B	111.0
C7—C8—H8	120.2	C16—C17—H17B	111.0
C9—C8—H8	120.2	H17A—C17—H17B	109.0
C8—C9—C10	119.2 (5)	O2—N1—O1	123.5 (6)
C8—C9—H9	120.4	O2—N1—C1	118.5 (6)
C10—C9—H9	120.4	O1—N1—C1	118.0 (6)
O6—C10—C11	117.6 (5)	O5—N2—O4	122.1 (6)
O6—C10—C9	121.9 (5)	O5—N2—C7	119.5 (6)
C11—C10—C9	120.5 (4)	O4—N2—C7	118.4 (6)
C12—C11—C10	120.1 (5)	C15—N3—C14	106.6 (4)
C12—C11—H11	120.0	C15—N3—H3A	111 (4)
C10—C11—H11	120.0	C14—N3—H3A	106 (4)
C11—C12—C7	119.0 (5)	C15—N3—H3B	110 (5)
C11—C12—H12	120.5	C14—N3—H3B	110 (5)
C7—C12—H12	120.5	H3A—N3—H3B	112 (6)
O8—C13—O7	126.2 (5)	C4—O3—H3C	109.5
O8—C13—C14	117.7 (4)	C10—O6—H6A	109.5
O7—C13—C14	116.1 (4)

C6—C1—C2—C3	0.0 (8)	O8—C13—C14—N3	3.8 (7)
N1—C1—C2—C3	179.4 (5)	O7—C13—C14—N3	−176.0 (5)
C1—C2—C3—C4	−1.4 (8)	O8—C13—C14—C16	121.9 (6)
C2—C3—C4—O3	−178.1 (5)	O7—C13—C14—C16	−57.8 (7)
C2—C3—C4—C5	1.7 (8)	N3—C14—C16—C17	−7.9 (7)
O3—C4—C5—C6	179.0 (5)	C13—C14—C16—C17	−128.4 (6)
C3—C4—C5—C6	−0.8 (8)	N3—C15—C17—C16	−39.1 (8)
C4—C5—C6—C1	−0.5 (9)	C14—C16—C17—C15	29.2 (8)
C2—C1—C6—C5	0.9 (9)	C6—C1—N1—O2	0.4 (8)
N1—C1—C6—C5	−178.5 (5)	C2—C1—N1—O2	−179.0 (5)
C12—C7—C8—C9	−0.7 (9)	C6—C1—N1—O1	−179.3 (5)
N2—C7—C8—C9	178.9 (5)	C2—C1—N1—O1	1.3 (7)
C7—C8—C9—C10	1.0 (8)	C8—C7—N2—O5	−175.9 (6)
C8—C9—C10—O6	179.1 (5)	C12—C7—N2—O5	3.7 (9)
C8—C9—C10—C11	−0.9 (8)	C8—C7—N2—O4	3.9 (8)
O6—C10—C11—C12	−179.6 (5)	C12—C7—N2—O4	−176.5 (6)
C9—C10—C11—C12	0.3 (8)	C17—C15—N3—C14	34.8 (7)
C10—C11—C12—C7	0.1 (9)	C13—C14—N3—C15	107.3 (5)
C8—C7—C12—C11	0.1 (9)	C16—C14—N3—C15	−16.6 (6)
N2—C7—C12—C11	−179.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O8	0.94 (6)	2.03 (6)	2.606 (6)	118 (5)
N3—H3B···O7ⁱ	0.93 (5)	1.87 (6)	2.766 (6)	160 (7)
O3—H3C···O7ⁱ	0.82	1.92	2.656 (5)	148
O6—H6A···O8ⁱⁱ	0.82	1.82	2.604 (5)	159
C11—H11···O1ⁱ	0.93	2.59	3.503 (8)	169

Symmetry codes: (i) x−1, y, z; (ii) −x+2, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O8	0.94 (6)	2.03 (6)	2.606 (6)	118 (5)
N3—H3B···O7ⁱ	0.93 (5)	1.87 (6)	2.766 (6)	160 (7)
O3—H3C···O7ⁱ	0.82	1.92	2.656 (5)	148
O6—H6A···O8ⁱⁱ	0.82	1.82	2.604 (5)	159
C11—H11···O1ⁱ	0.93	2.59	3.503 (8)	169

Symmetry codes: (i) x−1, y, z; (ii) −x+2, y−1/2, −z+3/2.

Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. TS also thanks DST Inspire for financial assistance.

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