2-(3,5-Dioxo-4-aza­tri­cyclo­[5.2.1.02,6]dec-8-en-4-yl)acetic acid

Akkurt, M.; Jarrahpour, A.; Shirvani, P.; Tahir, M.N.

doi:10.1107/S1600536813021764

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 9| September 2013| Page o1404

doi:10.1107/S1600536813021764

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2-(3,5-Dioxo-4-azatricyclo[5.2.1.0^2,6]dec-8-en-4-yl)acetic acid

Mehmet Akkurt,^a Aliasghar Jarrahpour,^b Pouria Shirvani ^b and Muhammad Nawaz Tahir ^c ^*

^aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bDepartment of Chemistry, College of Sciences, Shiraz University, 71454 Shiraz, Iran, and ^cDepartment of Physics, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 31 July 2013; accepted 4 August 2013; online 10 August 2013)

The asymmetric unit of the title compound, C₁₁H₁₁NO₄, contains two molecules, A and B, with different conformations: in molecule A, the norborne and carboxylic acid groups lie to the same side of the heterocycle, whereas in a molecule B, they lie on opposite sides. In the crystal, the A molecules form R₂²(8) carboxylic acid inversion dimers, linked by pairs of O—H⋯O hydrogen bonds. The B molecules link to one of the ketone O atoms of the A molecule by an O—H⋯O interaction, resulting in tetramers (two A and two B molecules). The tetramers are linked by weak C—H⋯O interactions, generating a three-dimensional network.

Related literature

For a related structure, see: Bartkowska et al. (1997 ). For further synthetic details, see: Biagini et al. (1995 ).

Experimental

Crystal data

C₁₁H₁₁NO₄
M_r = 221.21
Triclinic, $[P \overline 1]$
a = 6.5060 (3) Å
b = 11.8417 (4) Å
c = 14.1794 (5) Å
α = 104.385 (2)°
β = 97.905 (2)°
γ = 99.549 (2)°
V = 1025.07 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.28 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.970, T_max = 0.983
15543 measured reflections
3985 independent reflections
3245 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.107
S = 1.03
3985 reflections
292 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.82	1.84	2.6504 (18)	170
O5—H5A⋯O3ⁱⁱ	0.82	1.86	2.6509 (18)	163
C11—H11⋯O8ⁱⁱⁱ	0.93	2.57	3.440 (2)	156
C15—H15⋯O8^iv	0.98	2.33	3.201 (2)	147
C16—H16⋯O1^iv	0.98	2.48	3.1473 (19)	125
Symmetry codes: (i) -x-1, -y+1, -z+1; (ii) -x, -y+2, -z+1; (iii) -x, -y+1, -z+1; (iv) x+1, y, z.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); 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 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813021764/hb7113sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813021764/hb7113Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813021764/hb7113Isup3.cml

checkCIF report

Comment top

As shown in Fig. 1, the asymmetric unit of the title compound contains two independently molecules 1 (with N1) and 2 (with N2). The norbornene units of the molecules 1 and 2 are bound endo with respect to acetic acid. The sum of the three C—N—C angles at the imide N atom is 359.61 (13)° for molecule 1 and 359.88 (15) ° for molecule 2. In molecule 1, the N1—C2 bond length [1.448 (2) Å] is longer than the N1—C3 [1.3663 (19) Å] and N1—C6 [1.4044 (19) Å] bond lengths. In molecule 2, the corresponding bond lengths are N2—C13 of 1.442 (2) Å, N2—C17 of 1.377 (2) Å and N2—C14 of 1.384 (2) Å, respectively. As expected, this indicates a delocalized π-electron system along the imide parts of the molecules, as in a similar structure (Bartkowska et al., 1997).

In the crystal, pairs of molecules generate a dimer of the R²₂(8) motif by O—H···O hydrogen bonds; these two molecules are linked to the other two molecules by O—H···O hydrogen bonds (Table 1, Fig. 2). In addition, C—H···O hydrogen bonds contribute to the overall crystal packing.

Related literature top

For a related structure, see: Bartkowska et al. (1997). For further synthetic details, see: Biagini et al. (1995).

Experimental top

To endo-5-norbornene-2,3-dicarboxylic anhydride (16.41 g, 100.0 mmol) dissolved in DMF (30 ml) was added glycine (7.50 g, 100.0 mmol). The reaction mixture was refluxed for 24 h, coolded to room temperature, diluted with ethyl acetate (70 ml), and washed with saturated aqueous ammonium chloride solution (5×50 ml). The organic phase was dried on anhydrous Na₂SO₄, filtered and evaporated in vacuo. The residue was recrystallized (5 times) from etheyl acetate giving N-5-norbornene-2,3-dicarboxyloylglycine as a white crystalline solid (yield 61%); mp: 422–424 K (Biagini et al., 1995).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the two molecules of the title compound in the asymmetric unit. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
	Fig. 2. View of the dimer and C—H···O hydrogen bonds of the title compound along the a axis.

2-(3,5-Dioxo-4-azatricyclo[5.2.1.0^2,6]dec-8-en-4-yl)acetic acid top

Crystal data top

C₁₁H₁₁NO₄	Z = 4
M_r = 221.21	F(000) = 464
Triclinic, P1	D_x = 1.433 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.5060 (3) Å	Cell parameters from 318 reflections
b = 11.8417 (4) Å	θ = 3.1–22.5°
c = 14.1794 (5) Å	µ = 0.11 mm⁻¹
α = 104.385 (2)°	T = 296 K
β = 97.905 (2)°	Plate, colourless
γ = 99.549 (2)°	0.28 × 0.20 × 0.16 mm
V = 1025.07 (7) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	3985 independent reflections
Radiation source: fine-focus sealed tube	3245 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω scans	θ_max = 26.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
T_min = 0.970, T_max = 0.983	k = −14→12
15543 measured reflections	l = −17→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0458P)² + 0.3164P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3985 reflections	Δρ_max = 0.30 e Å⁻³
292 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), FC^*=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.031 (3)

Crystal data top

C₁₁H₁₁NO₄	γ = 99.549 (2)°
M_r = 221.21	V = 1025.07 (7) Å³
Triclinic, P1	Z = 4
a = 6.5060 (3) Å	Mo Kα radiation
b = 11.8417 (4) Å	µ = 0.11 mm⁻¹
c = 14.1794 (5) Å	T = 296 K
α = 104.385 (2)°	0.28 × 0.20 × 0.16 mm
β = 97.905 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3985 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3245 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.983	R_int = 0.032
15543 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.03	Δρ_max = 0.30 e Å⁻³
3985 reflections	Δρ_min = −0.21 e Å⁻³
292 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
O1	−0.35166 (19)	0.60085 (12)	0.60965 (8)	0.0532 (4)
O2	−0.34179 (18)	0.59322 (10)	0.45144 (8)	0.0457 (4)
O3	−0.18607 (17)	0.89261 (10)	0.44282 (8)	0.0444 (4)
O4	0.2190 (2)	0.64574 (12)	0.52862 (10)	0.0615 (5)
N1	0.00738 (18)	0.77624 (10)	0.50666 (9)	0.0330 (3)
C1	−0.2816 (2)	0.64006 (14)	0.54167 (11)	0.0370 (5)
C2	−0.1179 (3)	0.75396 (14)	0.57948 (11)	0.0398 (5)
C3	−0.0349 (2)	0.84335 (12)	0.44353 (10)	0.0326 (4)
C4	0.1310 (2)	0.84417 (13)	0.37965 (11)	0.0367 (4)
C5	0.2676 (2)	0.75925 (14)	0.40793 (11)	0.0392 (5)
C6	0.1738 (2)	0.71746 (14)	0.48685 (11)	0.0386 (5)
C7	0.2420 (3)	0.66135 (15)	0.30761 (13)	0.0483 (6)
C8	0.2424 (3)	0.74010 (16)	0.23690 (13)	0.0518 (6)
C9	0.0474 (3)	0.78668 (16)	0.26604 (12)	0.0488 (6)
C10	−0.0999 (3)	0.67172 (19)	0.25673 (13)	0.0596 (7)
C11	0.0136 (3)	0.59804 (16)	0.28153 (14)	0.0595 (6)
O5	0.2685 (2)	1.02427 (13)	0.71240 (10)	0.0613 (5)
O6	0.4902 (2)	0.91401 (12)	0.65030 (10)	0.0590 (5)
O7	0.8866 (3)	0.94587 (15)	0.86157 (14)	0.0927 (7)
O8	0.2460 (2)	0.69605 (13)	0.78880 (11)	0.0682 (5)
N2	0.5459 (2)	0.83974 (12)	0.82437 (10)	0.0422 (4)
C12	0.4055 (3)	0.95414 (13)	0.71640 (12)	0.0413 (5)
C13	0.4395 (3)	0.93605 (16)	0.81844 (13)	0.0537 (6)
C14	0.7635 (3)	0.85293 (17)	0.84901 (14)	0.0524 (6)
C15	0.8085 (3)	0.73603 (18)	0.85732 (13)	0.0520 (6)
C16	0.5937 (3)	0.65205 (14)	0.83248 (11)	0.0439 (5)
C17	0.4369 (3)	0.72531 (14)	0.81157 (11)	0.0399 (5)
C18	0.5844 (3)	0.60936 (17)	0.92804 (13)	0.0589 (7)
C19	0.8155 (4)	0.60299 (19)	0.95558 (15)	0.0725 (9)
C20	0.8975 (3)	0.73413 (19)	0.96526 (15)	0.0611 (7)
C21	0.7602 (4)	0.79025 (19)	1.03067 (13)	0.0604 (7)
C22	0.5757 (4)	0.7165 (2)	1.00967 (13)	0.0620 (7)
H1	−0.44970	0.54320	0.58450	0.0800*
H2A	−0.18820	0.81980	0.59930	0.0480*
H2B	−0.02410	0.75070	0.63770	0.0480*
H4	0.21650	0.92460	0.39260	0.0440*
H5	0.41620	0.80040	0.43240	0.0470*
H7	0.34670	0.61050	0.30410	0.0580*
H8A	0.21900	0.69480	0.16780	0.0620*
H8B	0.36930	0.80250	0.25300	0.0620*
H9	−0.00640	0.83860	0.22880	0.0590*
H10	−0.24660	0.65520	0.23680	0.0720*
H11	−0.03840	0.52050	0.28270	0.0710*
H5A	0.26000	1.04120	0.65950	0.0920*
H13A	0.52280	1.00910	0.86500	0.0650*
H13B	0.30300	0.91990	0.83800	0.0650*
H15	0.90050	0.70730	0.81150	0.0620*
H16	0.58550	0.58470	0.77470	0.0530*
H18	0.47950	0.53660	0.92080	0.0710*
H19A	0.86390	0.55010	0.90330	0.0870*
H19B	0.84650	0.58260	1.01740	0.0870*
H20	1.05070	0.76360	0.98820	0.0730*
H21	0.79850	0.86410	1.07780	0.0720*
H22	0.45980	0.72830	1.03990	0.0740*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0539 (8)	0.0664 (8)	0.0356 (6)	−0.0085 (6)	0.0056 (5)	0.0229 (6)
O2	0.0508 (7)	0.0526 (7)	0.0333 (6)	0.0019 (5)	0.0073 (5)	0.0175 (5)
O3	0.0453 (7)	0.0463 (6)	0.0503 (7)	0.0215 (5)	0.0128 (5)	0.0195 (5)
O4	0.0726 (9)	0.0697 (9)	0.0627 (8)	0.0401 (7)	0.0168 (7)	0.0368 (7)
N1	0.0329 (6)	0.0351 (6)	0.0331 (6)	0.0077 (5)	0.0074 (5)	0.0124 (5)
C1	0.0351 (8)	0.0458 (8)	0.0362 (8)	0.0120 (6)	0.0090 (6)	0.0189 (7)
C2	0.0453 (9)	0.0434 (8)	0.0334 (8)	0.0094 (7)	0.0113 (7)	0.0131 (6)
C3	0.0350 (8)	0.0269 (7)	0.0339 (7)	0.0048 (6)	0.0035 (6)	0.0077 (6)
C4	0.0413 (8)	0.0308 (7)	0.0405 (8)	0.0061 (6)	0.0126 (7)	0.0125 (6)
C5	0.0313 (8)	0.0454 (9)	0.0413 (8)	0.0097 (6)	0.0073 (6)	0.0112 (7)
C6	0.0368 (8)	0.0416 (8)	0.0383 (8)	0.0130 (7)	0.0032 (6)	0.0117 (7)
C7	0.0581 (11)	0.0466 (9)	0.0472 (9)	0.0235 (8)	0.0203 (8)	0.0116 (7)
C8	0.0610 (11)	0.0535 (10)	0.0441 (9)	0.0114 (8)	0.0228 (8)	0.0128 (8)
C9	0.0600 (11)	0.0591 (10)	0.0361 (9)	0.0240 (9)	0.0126 (8)	0.0199 (8)
C10	0.0478 (11)	0.0783 (14)	0.0369 (9)	−0.0007 (10)	0.0035 (8)	−0.0012 (9)
C11	0.0791 (14)	0.0413 (9)	0.0468 (10)	−0.0051 (9)	0.0195 (9)	−0.0011 (8)
O5	0.0718 (9)	0.0707 (9)	0.0633 (8)	0.0422 (7)	0.0204 (7)	0.0363 (7)
O6	0.0687 (9)	0.0656 (8)	0.0545 (8)	0.0322 (7)	0.0190 (7)	0.0223 (6)
O7	0.0668 (10)	0.0869 (11)	0.1180 (14)	−0.0239 (9)	−0.0078 (9)	0.0567 (10)
O8	0.0395 (8)	0.0742 (9)	0.0841 (10)	0.0003 (6)	0.0055 (7)	0.0205 (8)
N2	0.0412 (8)	0.0410 (7)	0.0485 (8)	0.0115 (6)	0.0040 (6)	0.0203 (6)
C12	0.0409 (9)	0.0343 (8)	0.0495 (9)	0.0085 (7)	0.0041 (7)	0.0151 (7)
C13	0.0706 (12)	0.0478 (10)	0.0494 (10)	0.0263 (9)	0.0084 (9)	0.0178 (8)
C14	0.0411 (10)	0.0630 (11)	0.0569 (11)	0.0010 (8)	0.0048 (8)	0.0324 (9)
C15	0.0426 (10)	0.0765 (12)	0.0533 (10)	0.0278 (9)	0.0183 (8)	0.0327 (9)
C16	0.0615 (11)	0.0407 (8)	0.0338 (8)	0.0192 (8)	0.0130 (7)	0.0106 (7)
C17	0.0405 (9)	0.0451 (9)	0.0351 (8)	0.0077 (7)	0.0103 (7)	0.0119 (7)
C18	0.0848 (14)	0.0483 (10)	0.0469 (10)	0.0084 (9)	0.0091 (9)	0.0244 (8)
C19	0.1114 (19)	0.0709 (14)	0.0522 (11)	0.0530 (13)	0.0125 (11)	0.0271 (10)
C20	0.0496 (11)	0.0810 (14)	0.0597 (12)	0.0251 (10)	−0.0006 (9)	0.0307 (10)
C21	0.0796 (15)	0.0617 (12)	0.0375 (9)	0.0257 (11)	−0.0025 (9)	0.0094 (8)
C22	0.0779 (14)	0.0836 (14)	0.0408 (10)	0.0317 (12)	0.0274 (10)	0.0281 (10)

Geometric parameters (Å, º) top

O1—C1	1.275 (2)	C4—H4	0.9800
O2—C1	1.2391 (18)	C5—H5	0.9800
O3—C3	1.2240 (18)	C7—H7	0.9800
O4—C6	1.201 (2)	C8—H8A	0.9700
O1—H1	0.8200	C8—H8B	0.9700
O5—C12	1.320 (2)	C9—H9	0.9800
O6—C12	1.190 (2)	C10—H10	0.9300
O7—C14	1.206 (3)	C11—H11	0.9300
O8—C17	1.208 (2)	C12—C13	1.507 (2)
O5—H5A	0.8200	C14—C15	1.491 (3)
N1—C6	1.4044 (19)	C15—C16	1.515 (3)
N1—C3	1.3663 (19)	C15—C20	1.567 (3)
N1—C2	1.448 (2)	C16—C18	1.565 (2)
N2—C14	1.384 (2)	C16—C17	1.490 (3)
N2—C17	1.377 (2)	C18—C19	1.520 (3)
N2—C13	1.442 (2)	C18—C22	1.505 (3)
C1—C2	1.499 (2)	C19—C20	1.521 (3)
C3—C4	1.5018 (19)	C20—C21	1.489 (3)
C4—C9	1.564 (2)	C21—C22	1.310 (4)
C4—C5	1.537 (2)	C13—H13A	0.9700
C5—C7	1.564 (2)	C13—H13B	0.9700
C5—C6	1.494 (2)	C15—H15	0.9800
C7—C11	1.500 (3)	C16—H16	0.9800
C7—C8	1.530 (3)	C18—H18	0.9800
C8—C9	1.532 (3)	C19—H19A	0.9700
C9—C10	1.494 (3)	C19—H19B	0.9700
C10—C11	1.313 (3)	C20—H20	0.9800
C2—H2B	0.9700	C21—H21	0.9300
C2—H2A	0.9700	C22—H22	0.9300

C1—O1—H1	109.00	C9—C10—H10	126.00
C12—O5—H5A	109.00	C11—C10—H10	126.00
C2—N1—C6	121.45 (13)	C10—C11—H11	126.00
C2—N1—C3	125.13 (13)	C7—C11—H11	126.00
C3—N1—C6	113.03 (12)	O5—C12—C13	108.83 (15)
C14—N2—C17	113.13 (15)	O6—C12—C13	126.08 (17)
C13—N2—C17	122.36 (15)	O5—C12—O6	125.09 (16)
C13—N2—C14	124.39 (15)	N2—C13—C12	113.30 (15)
O1—C1—O2	125.28 (15)	O7—C14—C15	128.9 (2)
O1—C1—C2	114.07 (13)	N2—C14—C15	107.95 (16)
O2—C1—C2	120.63 (14)	O7—C14—N2	123.17 (19)
N1—C2—C1	112.87 (12)	C14—C15—C20	114.56 (16)
O3—C3—N1	122.95 (13)	C16—C15—C20	103.08 (15)
O3—C3—C4	128.30 (13)	C14—C15—C16	105.36 (16)
N1—C3—C4	108.75 (12)	C15—C16—C18	102.94 (14)
C5—C4—C9	103.06 (13)	C17—C16—C18	115.33 (15)
C3—C4—C5	104.78 (12)	C15—C16—C17	105.32 (15)
C3—C4—C9	115.48 (12)	O8—C17—N2	122.86 (17)
C6—C5—C7	115.17 (14)	O8—C17—C16	128.93 (17)
C4—C5—C7	102.83 (12)	N2—C17—C16	108.20 (15)
C4—C5—C6	105.18 (11)	C16—C18—C19	99.66 (16)
O4—C6—N1	122.08 (14)	C16—C18—C22	106.71 (16)
N1—C6—C5	107.86 (13)	C19—C18—C22	99.66 (17)
O4—C6—C5	130.05 (14)	C18—C19—C20	93.79 (17)
C5—C7—C8	99.37 (14)	C15—C20—C19	99.08 (16)
C5—C7—C11	106.49 (15)	C15—C20—C21	107.11 (17)
C8—C7—C11	100.24 (15)	C19—C20—C21	100.74 (18)
C7—C8—C9	93.90 (14)	C20—C21—C22	107.46 (19)
C8—C9—C10	100.08 (15)	C18—C22—C21	107.9 (2)
C4—C9—C8	99.71 (13)	N2—C13—H13A	109.00
C4—C9—C10	105.91 (14)	N2—C13—H13B	109.00
C9—C10—C11	108.17 (17)	C12—C13—H13A	109.00
C7—C11—C10	107.79 (17)	C12—C13—H13B	109.00
N1—C2—H2A	109.00	H13A—C13—H13B	108.00
C1—C2—H2A	109.00	C14—C15—H15	111.00
C1—C2—H2B	109.00	C16—C15—H15	111.00
N1—C2—H2B	109.00	C20—C15—H15	111.00
H2A—C2—H2B	108.00	C15—C16—H16	111.00
C9—C4—H4	111.00	C17—C16—H16	111.00
C3—C4—H4	111.00	C18—C16—H16	111.00
C5—C4—H4	111.00	C16—C18—H18	116.00
C6—C5—H5	111.00	C19—C18—H18	116.00
C7—C5—H5	111.00	C22—C18—H18	116.00
C4—C5—H5	111.00	C18—C19—H19A	113.00
C11—C7—H7	116.00	C18—C19—H19B	113.00
C8—C7—H7	116.00	C20—C19—H19A	113.00
C5—C7—H7	116.00	C20—C19—H19B	113.00
C7—C8—H8B	113.00	H19A—C19—H19B	110.00
H8A—C8—H8B	110.00	C15—C20—H20	116.00
C9—C8—H8B	113.00	C19—C20—H20	116.00
C7—C8—H8A	113.00	C21—C20—H20	116.00
C9—C8—H8A	113.00	C20—C21—H21	126.00
C10—C9—H9	116.00	C22—C21—H21	126.00
C8—C9—H9	116.00	C18—C22—H22	126.00
C4—C9—H9	116.00	C21—C22—H22	126.00

C3—N1—C6—C5	6.13 (17)	C4—C5—C7—C8	38.05 (16)
C2—N1—C6—C5	179.33 (13)	C8—C7—C11—C10	−32.68 (19)
C3—N1—C2—C1	94.00 (18)	C5—C7—C11—C10	70.38 (19)
C6—N1—C2—C1	−78.35 (18)	C5—C7—C8—C9	−59.54 (15)
C2—N1—C3—O3	0.3 (2)	C11—C7—C8—C9	49.25 (16)
C6—N1—C3—O3	173.21 (14)	C7—C8—C9—C4	58.76 (15)
C2—N1—C3—C4	−179.72 (13)	C7—C8—C9—C10	−49.47 (15)
C6—N1—C3—C4	−6.82 (16)	C4—C9—C10—C11	−69.91 (19)
C3—N1—C6—O4	−172.69 (15)	C8—C9—C10—C11	33.32 (18)
C2—N1—C6—O4	0.5 (2)	C9—C10—C11—C7	−0.4 (2)
C14—N2—C17—C16	1.95 (18)	O5—C12—C13—N2	166.23 (15)
C13—N2—C14—C15	174.18 (15)	O6—C12—C13—N2	−15.0 (3)
C14—N2—C13—C12	91.2 (2)	O7—C14—C15—C16	−179.5 (2)
C17—N2—C14—C15	−2.1 (2)	N2—C14—C15—C16	1.29 (19)
C14—N2—C17—O8	−179.16 (16)	N2—C14—C15—C20	−111.26 (18)
C13—N2—C17—C16	−174.38 (14)	O7—C14—C15—C20	68.0 (3)
C13—N2—C17—O8	4.5 (2)	C14—C15—C16—C17	−0.18 (17)
C17—N2—C14—O7	178.64 (19)	C14—C15—C20—C21	47.5 (2)
C17—N2—C13—C12	−92.86 (19)	C16—C15—C20—C19	37.85 (19)
C13—N2—C14—O7	−5.1 (3)	C16—C15—C20—C21	−66.4 (2)
O1—C1—C2—N1	161.11 (14)	C20—C15—C16—C18	−0.96 (19)
O2—C1—C2—N1	−20.5 (2)	C14—C15—C16—C18	−121.38 (15)
N1—C3—C4—C9	117.19 (14)	C20—C15—C16—C17	120.24 (15)
O3—C3—C4—C9	−62.8 (2)	C14—C15—C20—C19	151.75 (18)
N1—C3—C4—C5	4.57 (15)	C15—C16—C17—O8	−179.80 (17)
O3—C3—C4—C5	−175.46 (15)	C15—C16—C18—C22	66.9 (2)
C5—C4—C9—C10	67.62 (16)	C17—C16—C18—C19	−150.46 (16)
C3—C4—C5—C6	−0.97 (15)	C17—C16—C18—C22	−47.2 (2)
C5—C4—C9—C8	−35.88 (16)	C15—C16—C17—N2	−1.00 (17)
C3—C4—C9—C8	−149.51 (14)	C18—C16—C17—O8	−67.1 (2)
C3—C4—C9—C10	−46.00 (19)	C18—C16—C17—N2	111.74 (16)
C3—C4—C5—C7	119.94 (13)	C15—C16—C18—C19	−36.34 (18)
C9—C4—C5—C6	−122.17 (13)	C16—C18—C19—C20	59.13 (16)
C9—C4—C5—C7	−1.26 (15)	C22—C18—C19—C20	−49.82 (17)
C4—C5—C6—N1	−2.81 (16)	C16—C18—C22—C21	−69.3 (2)
C4—C5—C6—O4	175.88 (17)	C19—C18—C22—C21	33.9 (2)
C6—C5—C7—C11	48.16 (18)	C18—C19—C20—C15	−59.50 (16)
C6—C5—C7—C8	151.85 (14)	C18—C19—C20—C21	49.99 (17)
C7—C5—C6—O4	63.5 (2)	C15—C20—C21—C22	70.5 (2)
C4—C5—C7—C11	−65.65 (16)	C19—C20—C21—C22	−32.6 (2)
C7—C5—C6—N1	−115.25 (15)	C20—C21—C22—C18	−0.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.84	2.6504 (18)	170
O5—H5A···O3ⁱⁱ	0.82	1.86	2.6509 (18)	163
C11—H11···O8ⁱⁱⁱ	0.93	2.57	3.440 (2)	156
C15—H15···O8^iv	0.98	2.33	3.201 (2)	147
C16—H16···O1^iv	0.98	2.48	3.1473 (19)	125

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.84	2.6504 (18)	170
O5—H5A···O3ⁱⁱ	0.82	1.86	2.6509 (18)	163
C11—H11···O8ⁱⁱⁱ	0.93	2.57	3.440 (2)	156
C15—H15···O8^iv	0.98	2.33	3.201 (2)	147
C16—H16···O1^iv	0.98	2.48	3.1473 (19)	125

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

Acknowledgements

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. AJ and PS thanks Shiraz University Research Council for financial support (grant No. 91-GR—SC-23).

References

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