Crystal structure of 2,2-dimethyl-N-(5-methyl­pyridin-2-yl)propanamide

El-Hiti, G.A.; Smith, K.; Hegazy, A.S.; Alanazi, S.A.; Kariuki, B.M.

doi:10.1107/S2056989015009378

organic compounds

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ISSN: 2056-9890

Volume 71| Part 6| June 2015| Pages o419-o420

doi:10.1107/S2056989015009378

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Crystal structure of 2,2-dimethyl-N-(5-methylpyridin-2-yl)propanamide

Gamal A. El-Hiti,^a ^* Keith Smith,^b Amany S. Hegazy,^b Saud A. Alanazi ^a and Benson M. Kariuki ^b ^*

^aCornea Research Chair, Department of Optometry, College of Applied Medical Sciences, King Saud University, PO Box 10219, Riyadh 11433, Saudi Arabia, and ^bSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, Wales
^*Correspondence e-mail: gelhiti@ksu.edu.sa, kariukib@cardiff.ac.uk

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 16 May 2015; accepted 17 May 2015; online 23 May 2015)

There are two molecules in the asymmetric unit of the title compound, C₁₁H₁₆N₂O. The pyridine rings and amide groups overlap almost perfectly (r.m.s. overlay fit = 0.053 Å), but the tertiary butyl groups have different orientations: in one molecule, one of the methyl C atoms is syn to the amide O atom [O—C—C—C = −0.8 (3)°] and in the other the equivalent torsion angle is 31.0 (2)°. In the crystal, the two independent molecules are linked by a pair of N—H⋯N hydrogen bonds in the form of an R₂²(8) loop to form a dimer. A C—H⋯O interaction connects the dimers into [100] chains.

Keywords: crystal structure; propanamide; hydrogen bonding.

CCDC reference: 1401551

1. Related literature

For the synthesis and spectroscopic data, see: Turner (1983 ). For related compounds, see: El-Hiti et al. (2015a ,b ); de Candia et al. (2013 ); Smith et al. (2013 , 2012 ); Abdel-Megeed et al. (2012 ); Joule & Mills (2000 ). For the crystal structures of related compounds, see: El-Hiti et al. (2014 ); Seidler et al. (2011 ); Koch et al. (2008 ).

2. Experimental

2.1. Crystal data

C₁₁H₁₆N₂O
M_r = 192.26
Monoclinic, P 2₁ /n
a = 11.1969 (2) Å
b = 8.6439 (2) Å
c = 23.8844 (5) Å
β = 94.549 (2)°
V = 2304.37 (8) Å³
Z = 8
Cu Kα radiation
μ = 0.57 mm⁻¹
T = 296 K
0.47 × 0.33 × 0.11 mm

2.2. Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014 ) T_min = 0.925, T_max = 0.975
8391 measured reflections
4503 independent reflections
3684 reflections with I > 2σ(I)
R_int = 0.021

2.3. Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.148
S = 1.04
4503 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.27 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
N2—H2A⋯N3	0.86	2.31	3.1192 (16)	156
N4—H4A⋯N1	0.86	2.25	3.0837 (16)	163
C4—H4⋯O2ⁱ	0.93	2.43	3.3262 (19)	160
Symmetry code: (i) x+1, y, z.

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2015 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

CCDC reference: 1401551

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S2056989015009378/hb7430sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015009378/hb7430Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015009378/hb7430Isup3.cml

checkCIF report

Introduction top

Substituted pyridines are important compounds (Joule & Mills, 2000) and show a range of biological activities (de Candia et al., 2013; Abdel-Megeed et al., 2012). The pyridine ring system has been modified using various efficient and simple procedures that include the use of lithium reagents as intermediates (El-Hiti et al., 2015; Smith et al., 2013, Smith et al., 2012; Turner, 1983). The X-ray crystal structures of related compounds have been reported (El-Hiti et al., 2015; El-Hiti et al., 2014; Seidler et al., 2011; Koch et al., 2008).

Experimental top

Synthesis and crystallization top

2,2-Dimethyl-N-(5-methylpyridin-2-yl)propanamide was obtained in 83% yield from reaction of 2-amino-5-methylpyridine with trimethylacetyl chloride in the presence of triethylamine in dichloromethane at 0 °C for 15 minutes and then at room temperature for 2 h (Turner, 1983). The crude product was purified by column chromatography (silica gel; dichloromethane) followed by crystallization from hexane to give colourless crystals of the title compound. The NMR spectral data and elemental analyses for the title compound were identical with those previously reported (Turner, 1983).

Refinement top

H atoms were positioned geometrically and refined using a riding model with U_iso(H) constrained to be 1.2 times U_eq for the atom it is bonded to except for methyl groups where it was 1.5 times with free rotation about the C—C bond.

Results and discussion top

The asymmetric unit (Figure 1) consists of two independent molecules of C₁₁H₁₆N₂O. The amide group and pyridine ring within the molecule are not co-planar as indicated by the torsion angles [N1—C1—N2—C7 = 142.20 (14), N3—C12—N4—C18 = 148.58 (15)]. The two independent molecules are linked by a pair of N—H···N hydrogen bonds (Table 1, Figure 2) to form an R₂²(8) ring.

Related literature top

For the synthesis and spectroscopic data, see: Turner (1983). For related compounds, see: El-Hiti et al. (2015a,b); de Candia et al. (2013); Smith et al. (2013, 2012); Abdel-Megeed et al. (2012). Joule & Mills (2000). For the crystal structures of related compounds, see: El-Hiti et al. (2014); Seidler et al. (2011); Koch et al. (2008).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2015); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. The asymmetric unit of C₁₁H₁₆N₂O with 50% probability displacement ellipsoids for nonhydrogen atoms.
	Fig. 2. The asymmetric unit showing N—H···N interactions as dotted lines.

2,2-Dimethyl-N-(5-methylpyridin-2-yl)propanamide top

Crystal data top

C₁₁H₁₆N₂O	F(000) = 832
M_r = 192.26	D_x = 1.108 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
a = 11.1969 (2) Å	Cell parameters from 3890 reflections
b = 8.6439 (2) Å	θ = 3.9–73.6°
c = 23.8844 (5) Å	µ = 0.57 mm⁻¹
β = 94.549 (2)°	T = 296 K
V = 2304.37 (8) Å³	Plate, colourless
Z = 8	0.47 × 0.33 × 0.11 mm

Data collection top

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	4503 independent reflections
Radiation source: sealed X-ray tube, SuperNova (Cu) X-ray Source	3684 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.021
ω scans	θ_max = 74.0°, θ_min = 3.7°
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014)	h = −13→13
T_min = 0.925, T_max = 0.975	k = −9→10
8391 measured reflections	l = −29→24

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.047	w = 1/[σ²(F_o²) + (0.081P)² + 0.208P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.148	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.27 e Å⁻³
4503 reflections	Δρ_min = −0.21 e Å⁻³
262 parameters	Extinction correction: SHELXL2013 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0075 (6)

Crystal data top

C₁₁H₁₆N₂O	V = 2304.37 (8) Å³
M_r = 192.26	Z = 8
Monoclinic, P2₁/n	Cu Kα radiation
a = 11.1969 (2) Å	µ = 0.57 mm⁻¹
b = 8.6439 (2) Å	T = 296 K
c = 23.8844 (5) Å	0.47 × 0.33 × 0.11 mm
β = 94.549 (2)°

Data collection top

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	4503 independent reflections
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014)	3684 reflections with I > 2σ(I)
T_min = 0.925, T_max = 0.975	R_int = 0.021
8391 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.148	H-atom parameters constrained
S = 1.04	Δρ_max = 0.27 e Å⁻³
4503 reflections	Δρ_min = −0.21 e Å⁻³
262 parameters

Special details top

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
C1	0.20122 (11)	0.54209 (16)	0.13526 (5)	0.0525 (3)
C2	0.19343 (14)	0.77138 (18)	0.08875 (7)	0.0650 (4)
H2	0.1480	0.8535	0.0736	0.097*
C3	0.31560 (14)	0.77581 (19)	0.08401 (7)	0.0670 (4)
C4	0.38057 (13)	0.6528 (2)	0.10739 (7)	0.0701 (4)
H4	0.4632	0.6499	0.1055	0.105*
C5	0.32450 (12)	0.5351 (2)	0.13327 (7)	0.0654 (4)
H5	0.3681	0.4524	0.1492	0.098*
C6	0.3730 (2)	0.9087 (3)	0.05543 (12)	0.1036 (7)
H6A	0.4566	0.9132	0.0677	0.155*
H6B	0.3349	1.0037	0.0649	0.155*
H6C	0.3639	0.8939	0.0155	0.155*
C7	0.15945 (14)	0.27433 (18)	0.16115 (6)	0.0618 (4)
C8	0.07563 (15)	0.16852 (19)	0.19135 (7)	0.0689 (4)
C9	0.1450 (2)	0.0226 (2)	0.21008 (9)	0.0942 (6)
H9A	0.1777	−0.0243	0.1782	0.141*
H9B	0.0920	−0.0490	0.2263	0.141*
H9C	0.2090	0.0496	0.2375	0.141*
C10	0.0273 (2)	0.2443 (2)	0.24272 (9)	0.0918 (6)
H10A	−0.0163	0.1692	0.2626	0.138*
H10B	−0.0250	0.3280	0.2309	0.138*
H10C	0.0929	0.2832	0.2670	0.138*
C11	−0.0263 (2)	0.1254 (3)	0.14762 (12)	0.1106 (8)
H11A	0.0066	0.0838	0.1149	0.166*
H11B	−0.0726	0.2160	0.1374	0.166*
H11C	−0.0768	0.0494	0.1631	0.166*
C12	−0.12246 (11)	0.71207 (16)	0.19991 (6)	0.0520 (3)
C13	−0.02137 (14)	0.65237 (19)	0.28397 (6)	0.0650 (4)
H13	0.0409	0.5995	0.3037	0.098*
C14	−0.09434 (14)	0.74294 (19)	0.31429 (6)	0.0634 (4)
C15	−0.18413 (15)	0.8222 (2)	0.28376 (7)	0.0710 (4)
H15	−0.2350	0.8861	0.3023	0.106*
C16	−0.19970 (14)	0.8082 (2)	0.22610 (7)	0.0660 (4)
H16	−0.2603	0.8618	0.2054	0.099*
C17	−0.0774 (2)	0.7526 (3)	0.37741 (7)	0.0909 (6)
H17A	−0.0997	0.8538	0.3894	0.136*
H17B	0.0051	0.7335	0.3895	0.136*
H17C	−0.1268	0.6765	0.3936	0.136*
C18	−0.22818 (13)	0.6925 (2)	0.10586 (6)	0.0671 (4)
C19	−0.21118 (14)	0.6626 (2)	0.04398 (6)	0.0714 (4)
C20	−0.1518 (2)	0.5048 (3)	0.03776 (9)	0.1036 (7)
H20A	−0.0736	0.5054	0.0575	0.155*
H20B	−0.1445	0.4838	−0.0013	0.155*
H20C	−0.1999	0.4260	0.0532	0.155*
C21	−0.1325 (2)	0.7892 (3)	0.02172 (9)	0.1074 (8)
H21A	−0.1659	0.8887	0.0293	0.161*
H21B	−0.1291	0.7767	−0.0181	0.161*
H21C	−0.0532	0.7819	0.0400	0.161*
C22	−0.33408 (17)	0.6641 (3)	0.01113 (8)	0.0955 (7)
H22A	−0.3810	0.5790	0.0230	0.143*
H22B	−0.3242	0.6546	−0.0283	0.143*
H22C	−0.3742	0.7596	0.0180	0.143*
N1	0.13561 (10)	0.65829 (14)	0.11338 (5)	0.0578 (3)
N2	0.13689 (10)	0.42840 (14)	0.16285 (5)	0.0577 (3)
H2A	0.0795	0.4589	0.1821	0.086*
N3	−0.03374 (10)	0.63507 (14)	0.22795 (5)	0.0589 (3)
N4	−0.12739 (10)	0.69100 (15)	0.14133 (5)	0.0585 (3)
H4A	−0.0606	0.6758	0.1267	0.088*
O1	0.23876 (14)	0.22212 (15)	0.13479 (7)	0.0942 (4)
O2	−0.32545 (10)	0.7145 (3)	0.12290 (6)	0.1234 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0471 (6)	0.0604 (7)	0.0506 (6)	−0.0005 (5)	0.0069 (5)	−0.0061 (5)
C2	0.0609 (8)	0.0606 (8)	0.0750 (9)	0.0020 (6)	0.0152 (7)	0.0019 (7)
C3	0.0619 (8)	0.0670 (9)	0.0739 (9)	−0.0103 (7)	0.0180 (7)	−0.0082 (7)
C4	0.0458 (7)	0.0872 (11)	0.0783 (10)	−0.0058 (7)	0.0111 (6)	−0.0054 (8)
C5	0.0476 (7)	0.0792 (10)	0.0695 (9)	0.0046 (7)	0.0061 (6)	0.0024 (7)
C6	0.0929 (14)	0.0845 (13)	0.139 (2)	−0.0182 (11)	0.0419 (13)	0.0105 (12)
C7	0.0633 (8)	0.0634 (8)	0.0595 (8)	0.0033 (7)	0.0093 (6)	−0.0058 (6)
C8	0.0743 (10)	0.0600 (8)	0.0730 (9)	−0.0017 (7)	0.0096 (8)	0.0039 (7)
C9	0.1260 (17)	0.0716 (11)	0.0864 (12)	0.0159 (11)	0.0172 (12)	0.0096 (9)
C10	0.1089 (15)	0.0753 (11)	0.0977 (13)	0.0020 (10)	0.0486 (12)	0.0135 (10)
C11	0.0982 (15)	0.1086 (17)	0.1210 (18)	−0.0325 (13)	−0.0168 (14)	0.0207 (14)
C12	0.0441 (6)	0.0584 (7)	0.0541 (7)	−0.0037 (5)	0.0082 (5)	−0.0028 (5)
C13	0.0649 (8)	0.0748 (9)	0.0553 (8)	0.0084 (7)	0.0041 (6)	0.0003 (7)
C14	0.0628 (8)	0.0718 (9)	0.0566 (8)	−0.0045 (7)	0.0101 (6)	−0.0074 (6)
C15	0.0643 (9)	0.0830 (10)	0.0672 (9)	0.0103 (8)	0.0145 (7)	−0.0160 (8)
C16	0.0574 (8)	0.0769 (9)	0.0643 (8)	0.0125 (7)	0.0078 (6)	−0.0056 (7)
C17	0.0947 (13)	0.1195 (16)	0.0590 (9)	0.0039 (12)	0.0092 (9)	−0.0124 (10)
C18	0.0479 (7)	0.0957 (11)	0.0581 (8)	−0.0060 (7)	0.0062 (6)	−0.0059 (7)
C19	0.0574 (8)	0.1030 (12)	0.0540 (8)	−0.0056 (8)	0.0058 (6)	−0.0037 (8)
C20	0.1021 (15)	0.1323 (18)	0.0765 (12)	0.0172 (14)	0.0078 (10)	−0.0312 (12)
C21	0.0894 (13)	0.161 (2)	0.0718 (11)	−0.0318 (14)	0.0046 (10)	0.0262 (13)
C22	0.0681 (10)	0.153 (2)	0.0636 (10)	−0.0080 (12)	−0.0058 (8)	−0.0082 (11)
N1	0.0483 (6)	0.0612 (6)	0.0649 (7)	0.0024 (5)	0.0111 (5)	−0.0014 (5)
N2	0.0517 (6)	0.0616 (7)	0.0612 (6)	0.0020 (5)	0.0141 (5)	0.0003 (5)
N3	0.0564 (6)	0.0654 (7)	0.0555 (6)	0.0082 (5)	0.0078 (5)	−0.0030 (5)
N4	0.0464 (6)	0.0772 (8)	0.0526 (6)	0.0019 (5)	0.0081 (5)	−0.0045 (5)
O1	0.1027 (10)	0.0738 (8)	0.1127 (10)	0.0100 (7)	0.0496 (8)	−0.0114 (7)
O2	0.0451 (6)	0.250 (2)	0.0754 (8)	−0.0005 (9)	0.0067 (5)	−0.0370 (11)

Geometric parameters (Å, º) top

C1—N1	1.3269 (18)	C12—C16	1.384 (2)
C1—C5	1.3862 (19)	C12—N4	1.4077 (17)
C1—N2	1.4122 (17)	C13—N3	1.3427 (19)
C2—N1	1.3346 (19)	C13—C14	1.378 (2)
C2—C3	1.382 (2)	C13—H13	0.9300
C2—H2	0.9300	C14—C15	1.377 (2)
C3—C4	1.381 (2)	C14—C17	1.507 (2)
C3—C6	1.506 (2)	C15—C16	1.380 (2)
C4—C5	1.368 (2)	C15—H15	0.9300
C4—H4	0.9300	C16—H16	0.9300
C5—H5	0.9300	C17—H17A	0.9600
C6—H6A	0.9600	C17—H17B	0.9600
C6—H6B	0.9600	C17—H17C	0.9600
C6—H6C	0.9600	C18—O2	1.208 (2)
C7—O1	1.2155 (19)	C18—N4	1.3565 (19)
C7—N2	1.3567 (19)	C18—C19	1.527 (2)
C7—C8	1.531 (2)	C19—C21	1.526 (3)
C8—C10	1.527 (3)	C19—C22	1.529 (2)
C8—C9	1.529 (3)	C19—C20	1.531 (3)
C8—C11	1.531 (3)	C20—H20A	0.9600
C9—H9A	0.9600	C20—H20B	0.9600
C9—H9B	0.9600	C20—H20C	0.9600
C9—H9C	0.9600	C21—H21A	0.9600
C10—H10A	0.9600	C21—H21B	0.9600
C10—H10B	0.9600	C21—H21C	0.9600
C10—H10C	0.9600	C22—H22A	0.9600
C11—H11A	0.9600	C22—H22B	0.9600
C11—H11B	0.9600	C22—H22C	0.9600
C11—H11C	0.9600	N2—H2A	0.8600
C12—N3	1.3314 (18)	N4—H4A	0.8600

N1—C1—C5	122.76 (13)	N3—C13—H13	117.7
N1—C1—N2	115.06 (11)	C14—C13—H13	117.7
C5—C1—N2	122.13 (13)	C15—C14—C13	116.30 (14)
N1—C2—C3	125.05 (15)	C15—C14—C17	122.08 (15)
N1—C2—H2	117.5	C13—C14—C17	121.62 (16)
C3—C2—H2	117.5	C14—C15—C16	120.94 (14)
C4—C3—C2	116.01 (14)	C14—C15—H15	119.5
C4—C3—C6	122.73 (16)	C16—C15—H15	119.5
C2—C3—C6	121.25 (17)	C15—C16—C12	118.01 (14)
C5—C4—C3	120.60 (14)	C15—C16—H16	121.0
C5—C4—H4	119.7	C12—C16—H16	121.0
C3—C4—H4	119.7	C14—C17—H17A	109.5
C4—C5—C1	118.49 (15)	C14—C17—H17B	109.5
C4—C5—H5	120.8	H17A—C17—H17B	109.5
C1—C5—H5	120.8	C14—C17—H17C	109.5
C3—C6—H6A	109.5	H17A—C17—H17C	109.5
C3—C6—H6B	109.5	H17B—C17—H17C	109.5
H6A—C6—H6B	109.5	O2—C18—N4	121.25 (14)
C3—C6—H6C	109.5	O2—C18—C19	122.54 (14)
H6A—C6—H6C	109.5	N4—C18—C19	116.20 (13)
H6B—C6—H6C	109.5	C21—C19—C18	109.61 (16)
O1—C7—N2	121.70 (15)	C21—C19—C22	109.63 (17)
O1—C7—C8	121.50 (15)	C18—C19—C22	108.60 (14)
N2—C7—C8	116.72 (13)	C21—C19—C20	109.78 (18)
C10—C8—C9	108.82 (16)	C18—C19—C20	109.45 (16)
C10—C8—C11	111.11 (19)	C22—C19—C20	109.75 (18)
C9—C8—C11	109.45 (17)	C19—C20—H20A	109.5
C10—C8—C7	113.06 (14)	C19—C20—H20B	109.5
C9—C8—C7	108.31 (15)	H20A—C20—H20B	109.5
C11—C8—C7	106.00 (15)	C19—C20—H20C	109.5
C8—C9—H9A	109.5	H20A—C20—H20C	109.5
C8—C9—H9B	109.5	H20B—C20—H20C	109.5
H9A—C9—H9B	109.5	C19—C21—H21A	109.5
C8—C9—H9C	109.5	C19—C21—H21B	109.5
H9A—C9—H9C	109.5	H21A—C21—H21B	109.5
H9B—C9—H9C	109.5	C19—C21—H21C	109.5
C8—C10—H10A	109.5	H21A—C21—H21C	109.5
C8—C10—H10B	109.5	H21B—C21—H21C	109.5
H10A—C10—H10B	109.5	C19—C22—H22A	109.5
C8—C10—H10C	109.5	C19—C22—H22B	109.5
H10A—C10—H10C	109.5	H22A—C22—H22B	109.5
H10B—C10—H10C	109.5	C19—C22—H22C	109.5
C8—C11—H11A	109.5	H22A—C22—H22C	109.5
C8—C11—H11B	109.5	H22B—C22—H22C	109.5
H11A—C11—H11B	109.5	C1—N1—C2	117.08 (12)
C8—C11—H11C	109.5	C7—N2—C1	124.47 (12)
H11A—C11—H11C	109.5	C7—N2—H2A	117.8
H11B—C11—H11C	109.5	C1—N2—H2A	117.8
N3—C12—C16	122.75 (13)	C12—N3—C13	117.35 (12)
N3—C12—N4	113.83 (11)	C18—N4—C12	125.79 (12)
C16—C12—N4	123.38 (13)	C18—N4—H4A	117.1
N3—C13—C14	124.64 (14)	C12—N4—H4A	117.1

N1—C2—C3—C4	−0.6 (3)	O2—C18—C19—C21	119.0 (2)
N1—C2—C3—C6	−179.97 (18)	N4—C18—C19—C21	−61.9 (2)
C2—C3—C4—C5	0.2 (2)	O2—C18—C19—C22	−0.8 (3)
C6—C3—C4—C5	179.56 (18)	N4—C18—C19—C22	178.35 (18)
C3—C4—C5—C1	0.3 (2)	O2—C18—C19—C20	−120.6 (2)
N1—C1—C5—C4	−0.3 (2)	N4—C18—C19—C20	58.5 (2)
N2—C1—C5—C4	−177.72 (14)	C5—C1—N1—C2	0.0 (2)
O1—C7—C8—C10	151.67 (19)	N2—C1—N1—C2	177.54 (12)
N2—C7—C8—C10	−31.6 (2)	C3—C2—N1—C1	0.5 (2)
O1—C7—C8—C9	31.0 (2)	O1—C7—N2—C1	−0.2 (2)
N2—C7—C8—C9	−152.30 (15)	C8—C7—N2—C1	−176.94 (13)
O1—C7—C8—C11	−86.4 (2)	N1—C1—N2—C7	142.20 (14)
N2—C7—C8—C11	90.33 (19)	C5—C1—N2—C7	−40.2 (2)
N3—C13—C14—C15	−1.3 (3)	C16—C12—N3—C13	0.6 (2)
N3—C13—C14—C17	177.95 (17)	N4—C12—N3—C13	178.41 (13)
C13—C14—C15—C16	0.9 (3)	C14—C13—N3—C12	0.5 (2)
C17—C14—C15—C16	−178.27 (18)	O2—C18—N4—C12	0.7 (3)
C14—C15—C16—C12	0.1 (3)	C19—C18—N4—C12	−178.44 (15)
N3—C12—C16—C15	−0.9 (2)	N3—C12—N4—C18	148.58 (15)
N4—C12—C16—C15	−178.46 (15)	C16—C12—N4—C18	−33.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N3	0.86	2.31	3.1192 (16)	156
N4—H4A···N1	0.86	2.25	3.0837 (16)	163
C4—H4···O2ⁱ	0.93	2.43	3.3262 (19)	160

Symmetry code: (i) x+1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N3	0.86	2.31	3.1192 (16)	156
N4—H4A···N1	0.86	2.25	3.0837 (16)	163
C4—H4···O2ⁱ	0.93	2.43	3.3262 (19)	160

Symmetry code: (i) x+1, y, z.

Acknowledgements

The authors extend their appreciation to the Cornea Research Chair, Department of Optometry, College of Applied Medical Sciences, King Saud University, for funding this research.

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Volume 71| Part 6| June 2015| Pages o419-o420

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