5-Meth­oxy-2-[(2-morpholinoeth­yl)­iminio­meth­yl]phenolate

Mohd Lair, N.; Mohd Ali, H.; Ng, S.W.

doi:10.1107/S1600536809013786

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1067

doi:10.1107/S1600536809013786

Open

access

5-Methoxy-2-[(2-morpholinoethyl)iminiomethyl]phenolate

Nooraziah Mohd Lair,^a Hapipah Mohd Ali ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 12 April 2009; accepted 13 April 2009; online 18 April 2009)

Each of the two independent molecules of the title comound, C₁₄H₂₀N₂O₃, exists in the zwitterionic form as the imino N atoms are protonated. The =N—H unit forms an intramolecular hydrogen bond to the negatively charged O atom, and also a weaker intermolecular N—H⋯O bond, the latter resulting in inversion dimers.

Related literature

For the structure of 2-[(2-morpholinoethylimino)methyl]phenol, see: Petek et al. (2005 ).

Experimental

Crystal data

C₁₄H₂₀N₂O₃
M_r = 264.32
Triclinic, $[P \overline 1]$
a = 10.4022 (2) Å
b = 10.7340 (2) Å
c = 14.3497 (3) Å
α = 83.523 (1)°
β = 74.810 (1)°
γ = 60.768 (1)°
V = 1349.13 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.25 × 0.25 × 0.25 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
9402 measured reflections
5948 independent reflections
4990 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.122
S = 1.04
5948 reflections
353 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.88 (1)	1.96 (1)	2.6489 (15)	133 (2)
N1—H1⋯O1ⁱ	0.88 (1)	2.32 (1)	2.9570 (18)	129 (1)
N3—H3⋯O4	0.89 (1)	2.02 (1)	2.6930 (15)	132 (1)
N3—H3⋯O4ⁱⁱ	0.89 (1)	2.29 (1)	2.9505 (18)	132 (1)
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+3, -y, -z-1.

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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809013786/tk2422sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809013786/tk2422Isup2.hkl

checkCIF report

Related literature top

For the structure of 2-(2-morpholinylethyliminimethyl)phenol, see: Petek et al. (2005).

Experimental top

2-Hydroxy-4-methoxybenzaldehyde (0.3 g, 2 mmol) and N-(2-aminoethyl)morpholine (0.26 g, 2 mmol) were heated in acidified ethanol (50 ml) for 8 h. The solvent was removed to give an oil; crystals appeared in the oil after several days.

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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the two independent molecules of C₁₄H₂₀N₂O₃ at the 70% probability level. H atoms are drawn as spheres of arbitrary radius.

5-Methoxy-2-[(2-morpholinoethyl)iminiomethyl]phenolate top

Crystal data top

C₁₄H₂₀N₂O₃	Z = 4
M_r = 264.32	F(000) = 568
Triclinic, P1	D_x = 1.301 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.4022 (2) Å	Cell parameters from 4712 reflections
b = 10.7340 (2) Å	θ = 2.3–28.3°
c = 14.3497 (3) Å	µ = 0.09 mm⁻¹
α = 83.523 (1)°	T = 100 K
β = 74.810 (1)°	Block, yellow
γ = 60.768 (1)°	0.25 × 0.25 × 0.25 mm
V = 1349.13 (5) Å³

Data collection top

Bruker SMART APEX diffractometer	4990 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.019
Graphite monochromator	θ_max = 27.5°, θ_min = 1.5°
ω scans	h = −13→13
9402 measured reflections	k = −13→13
5948 independent reflections	l = −18→16

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0696P)² + 0.3249P] where P = (F_o² + 2F_c²)/3
5948 reflections	(Δ/σ)_max = 0.001
353 parameters	Δρ_max = 0.31 e Å⁻³
2 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₄H₂₀N₂O₃	γ = 60.768 (1)°
M_r = 264.32	V = 1349.13 (5) Å³
Triclinic, P1	Z = 4
a = 10.4022 (2) Å	Mo Kα radiation
b = 10.7340 (2) Å	µ = 0.09 mm⁻¹
c = 14.3497 (3) Å	T = 100 K
α = 83.523 (1)°	0.25 × 0.25 × 0.25 mm
β = 74.810 (1)°

Data collection top

Bruker SMART APEX diffractometer	4990 reflections with I > 2σ(I)
9402 measured reflections	R_int = 0.019
5948 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	2 restraints
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.31 e Å⁻³
5948 reflections	Δρ_min = −0.28 e Å⁻³
353 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.98316 (10)	0.43387 (9)	0.41326 (7)	0.0206 (2)
O2	0.96310 (10)	0.15768 (9)	0.18272 (6)	0.0212 (2)
O3	0.38917 (12)	0.92759 (12)	0.95202 (8)	0.0352 (3)
O4	1.50070 (10)	−0.11554 (10)	−0.55972 (7)	0.0248 (2)
O5	1.47841 (10)	−0.36606 (9)	−0.80663 (6)	0.0207 (2)
O6	0.93660 (11)	0.37780 (10)	−0.02785 (6)	0.0226 (2)
N1	0.77639 (12)	0.49804 (11)	0.57933 (8)	0.0179 (2)
H1	0.8542 (15)	0.5066 (19)	0.5426 (11)	0.039 (5)*
N2	0.60959 (11)	0.75546 (11)	0.78788 (7)	0.0168 (2)
N3	1.23596 (12)	0.09777 (11)	−0.46514 (8)	0.0201 (2)
H3	1.3361 (10)	0.0512 (16)	−0.4734 (12)	0.034 (5)*
N4	1.02064 (11)	0.24956 (10)	−0.21452 (7)	0.0163 (2)
C1	0.91918 (13)	0.37426 (12)	0.38550 (9)	0.0157 (2)
C2	0.98177 (13)	0.29765 (12)	0.29480 (9)	0.0165 (2)
H2	1.0732	0.2909	0.2540	0.020*
C3	0.91073 (14)	0.23419 (12)	0.26664 (9)	0.0165 (2)
C4	0.77322 (14)	0.24178 (12)	0.32475 (9)	0.0178 (3)
H4	0.7249	0.1988	0.3032	0.021*
C5	0.71188 (13)	0.31159 (12)	0.41178 (9)	0.0174 (2)
H5	0.6208	0.3158	0.4512	0.021*
C6	0.78113 (13)	0.37826 (12)	0.44499 (9)	0.0157 (2)
C7	1.11022 (15)	0.12990 (14)	0.12544 (9)	0.0226 (3)
H7A	1.1382	0.0687	0.0699	0.034*
H7B	1.1850	0.0817	0.1647	0.034*
H7C	1.1080	0.2203	0.1026	0.034*
C8	0.72030 (14)	0.43854 (12)	0.53895 (9)	0.0171 (2)
H8	0.6315	0.4357	0.5759	0.021*
C9	0.72088 (15)	0.54438 (13)	0.68036 (9)	0.0193 (3)
H9A	0.8066	0.5011	0.7122	0.023*
H9B	0.6470	0.5115	0.7139	0.023*
C10	0.64529 (14)	0.70646 (13)	0.68841 (9)	0.0180 (3)
H10A	0.7136	0.7401	0.6460	0.022*
H10B	0.5506	0.7489	0.6657	0.022*
C11	0.54085 (16)	0.91155 (14)	0.78853 (10)	0.0248 (3)
H11A	0.4522	0.9524	0.7595	0.030*
H11B	0.6154	0.9399	0.7486	0.030*
C12	0.49055 (17)	0.97165 (15)	0.88980 (10)	0.0297 (3)
H12A	0.5807	0.9394	0.9161	0.036*
H12B	0.4397	1.0772	0.8877	0.036*
C13	0.46395 (18)	0.77580 (18)	0.95435 (10)	0.0333 (4)
H13A	0.3965	0.7439	0.9998	0.040*
H13B	0.5568	0.7415	0.9780	0.040*
C14	0.50611 (16)	0.71168 (16)	0.85489 (10)	0.0271 (3)
H14A	0.5558	0.6062	0.8584	0.032*
H14B	0.4134	0.7446	0.8313	0.032*
C15	1.42646 (14)	−0.13723 (13)	−0.60736 (9)	0.0178 (3)
C16	1.49985 (14)	−0.24612 (12)	−0.68219 (9)	0.0176 (3)
H16	1.6069	−0.3044	−0.6959	0.021*
C17	1.41790 (14)	−0.26689 (12)	−0.73376 (9)	0.0168 (2)
C18	1.25664 (14)	−0.18526 (13)	−0.71453 (9)	0.0187 (3)
H18	1.2014	−0.2031	−0.7497	0.022*
C19	1.18346 (14)	−0.08089 (13)	−0.64448 (9)	0.0184 (3)
H19	1.0762	−0.0254	−0.6318	0.022*
C20	1.26264 (14)	−0.05270 (12)	−0.59010 (9)	0.0172 (2)
C21	1.64017 (15)	−0.44652 (14)	−0.83657 (10)	0.0248 (3)
H21A	1.6685	−0.5143	−0.8881	0.037*
H21B	1.6807	−0.4988	−0.7815	0.037*
H21C	1.6821	−0.3815	−0.8606	0.037*
C22	1.17933 (14)	0.05782 (13)	−0.51997 (9)	0.0185 (3)
H22	1.0723	0.1080	−0.5116	0.022*
C23	1.14126 (15)	0.21047 (13)	−0.39115 (9)	0.0216 (3)
H23A	1.0390	0.2691	−0.4037	0.026*
H23B	1.1866	0.2735	−0.3935	0.026*
C24	1.12827 (14)	0.14453 (12)	−0.29159 (9)	0.0181 (3)
H24A	1.0959	0.0721	−0.2928	0.022*
H24B	1.2295	0.0951	−0.2769	0.022*
C25	1.07626 (14)	0.34487 (13)	−0.19663 (9)	0.0192 (3)
H25A	1.0905	0.3981	−0.2560	0.023*
H25B	1.1758	0.2874	−0.1802	0.023*
C26	0.96492 (15)	0.44957 (13)	−0.11458 (9)	0.0208 (3)
H26A	1.0061	0.5105	−0.1025	0.025*
H26B	0.8682	0.5123	−0.1335	0.025*
C27	0.88279 (15)	0.28513 (14)	−0.04521 (9)	0.0222 (3)
H27A	0.7851	0.3425	−0.0640	0.027*
H27B	0.8647	0.2350	0.0150	0.027*
C28	0.99553 (15)	0.17629 (13)	−0.12430 (9)	0.0197 (3)
H28A	1.0928	0.1171	−0.1052	0.024*
H28B	0.9562	0.1126	−0.1341	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0209 (5)	0.0253 (5)	0.0202 (5)	−0.0151 (4)	−0.0019 (4)	−0.0037 (4)
O2	0.0215 (5)	0.0235 (4)	0.0180 (5)	−0.0106 (4)	−0.0018 (4)	−0.0062 (4)
O3	0.0228 (5)	0.0519 (7)	0.0277 (6)	−0.0175 (5)	0.0070 (4)	−0.0198 (5)
O4	0.0196 (5)	0.0286 (5)	0.0258 (5)	−0.0094 (4)	−0.0061 (4)	−0.0070 (4)
O5	0.0196 (5)	0.0214 (4)	0.0209 (5)	−0.0100 (4)	−0.0010 (4)	−0.0069 (4)
O6	0.0290 (5)	0.0254 (5)	0.0166 (5)	−0.0158 (4)	−0.0034 (4)	−0.0028 (4)
N1	0.0177 (5)	0.0197 (5)	0.0152 (5)	−0.0093 (4)	−0.0004 (4)	−0.0020 (4)
N2	0.0167 (5)	0.0195 (5)	0.0132 (5)	−0.0089 (4)	−0.0008 (4)	−0.0013 (4)
N3	0.0181 (5)	0.0199 (5)	0.0174 (5)	−0.0061 (4)	−0.0012 (4)	−0.0033 (4)
N4	0.0173 (5)	0.0173 (5)	0.0141 (5)	−0.0087 (4)	−0.0014 (4)	−0.0028 (4)
C1	0.0158 (6)	0.0148 (5)	0.0162 (6)	−0.0071 (4)	−0.0045 (5)	0.0014 (4)
C2	0.0153 (6)	0.0170 (5)	0.0158 (6)	−0.0074 (5)	−0.0022 (5)	0.0007 (4)
C3	0.0174 (6)	0.0140 (5)	0.0151 (6)	−0.0047 (4)	−0.0048 (5)	−0.0003 (4)
C4	0.0172 (6)	0.0178 (5)	0.0216 (6)	−0.0095 (5)	−0.0074 (5)	0.0008 (5)
C5	0.0142 (5)	0.0172 (5)	0.0194 (6)	−0.0072 (5)	−0.0037 (5)	0.0027 (5)
C6	0.0144 (5)	0.0149 (5)	0.0160 (6)	−0.0060 (4)	−0.0031 (4)	0.0008 (4)
C7	0.0221 (6)	0.0224 (6)	0.0182 (6)	−0.0087 (5)	0.0009 (5)	−0.0033 (5)
C8	0.0146 (6)	0.0164 (5)	0.0180 (6)	−0.0066 (5)	−0.0022 (5)	0.0011 (4)
C9	0.0224 (6)	0.0213 (6)	0.0139 (6)	−0.0115 (5)	−0.0012 (5)	−0.0015 (5)
C10	0.0171 (6)	0.0209 (6)	0.0139 (6)	−0.0079 (5)	−0.0021 (5)	−0.0015 (5)
C11	0.0258 (7)	0.0208 (6)	0.0200 (7)	−0.0048 (5)	−0.0047 (5)	−0.0034 (5)
C12	0.0300 (7)	0.0288 (7)	0.0245 (7)	−0.0109 (6)	0.0001 (6)	−0.0090 (6)
C13	0.0389 (8)	0.0540 (9)	0.0177 (7)	−0.0346 (8)	0.0055 (6)	−0.0074 (6)
C14	0.0290 (7)	0.0415 (8)	0.0183 (7)	−0.0251 (7)	0.0019 (5)	−0.0056 (6)
C15	0.0190 (6)	0.0188 (5)	0.0159 (6)	−0.0099 (5)	−0.0034 (5)	0.0011 (4)
C16	0.0146 (6)	0.0178 (5)	0.0189 (6)	−0.0073 (5)	−0.0021 (5)	−0.0004 (5)
C17	0.0199 (6)	0.0151 (5)	0.0150 (6)	−0.0093 (5)	−0.0014 (5)	0.0001 (4)
C18	0.0187 (6)	0.0213 (6)	0.0191 (6)	−0.0110 (5)	−0.0063 (5)	0.0013 (5)
C19	0.0158 (6)	0.0184 (6)	0.0187 (6)	−0.0071 (5)	−0.0037 (5)	0.0029 (5)
C20	0.0176 (6)	0.0170 (5)	0.0152 (6)	−0.0078 (5)	−0.0026 (5)	0.0013 (4)
C21	0.0208 (6)	0.0220 (6)	0.0275 (7)	−0.0086 (5)	0.0008 (5)	−0.0084 (5)
C22	0.0176 (6)	0.0188 (6)	0.0170 (6)	−0.0080 (5)	−0.0031 (5)	0.0026 (5)
C23	0.0216 (6)	0.0195 (6)	0.0188 (6)	−0.0061 (5)	−0.0023 (5)	−0.0051 (5)
C24	0.0168 (6)	0.0170 (5)	0.0183 (6)	−0.0055 (5)	−0.0044 (5)	−0.0038 (5)
C25	0.0199 (6)	0.0207 (6)	0.0185 (6)	−0.0115 (5)	−0.0021 (5)	−0.0024 (5)
C26	0.0253 (7)	0.0204 (6)	0.0187 (6)	−0.0127 (5)	−0.0035 (5)	−0.0028 (5)
C27	0.0242 (7)	0.0271 (6)	0.0183 (6)	−0.0158 (6)	−0.0016 (5)	−0.0017 (5)
C28	0.0237 (6)	0.0206 (6)	0.0178 (6)	−0.0128 (5)	−0.0048 (5)	0.0000 (5)

Geometric parameters (Å, º) top

O1—C1	1.2741 (15)	C10—H10B	0.9900
O2—C3	1.3652 (14)	C11—C12	1.5115 (18)
O2—C7	1.4342 (15)	C11—H11A	0.9900
O3—C13	1.423 (2)	C11—H11B	0.9900
O3—C12	1.4253 (18)	C12—H12A	0.9900
O4—C15	1.2673 (16)	C12—H12B	0.9900
O5—C17	1.3691 (14)	C13—C14	1.5172 (18)
O5—C21	1.4308 (15)	C13—H13A	0.9900
O6—C27	1.4274 (15)	C13—H13B	0.9900
O6—C26	1.4291 (15)	C14—H14A	0.9900
N1—C8	1.3071 (16)	C14—H14B	0.9900
N1—C9	1.4581 (16)	C15—C16	1.4436 (17)
N1—H1	0.883 (9)	C15—C20	1.4518 (17)
N2—C11	1.4657 (16)	C16—C17	1.3702 (18)
N2—C10	1.4673 (15)	C16—H16	0.9500
N2—C14	1.4676 (16)	C17—C18	1.4263 (17)
N3—C22	1.3097 (17)	C18—C19	1.3657 (17)
N3—C23	1.4625 (15)	C18—H18	0.9500
N3—H3	0.889 (9)	C19—C20	1.4187 (18)
N4—C24	1.4654 (15)	C19—H19	0.9500
N4—C28	1.4685 (16)	C20—C22	1.4068 (17)
N4—C25	1.4706 (15)	C21—H21A	0.9800
C1—C2	1.4383 (16)	C21—H21B	0.9800
C1—C6	1.4486 (16)	C21—H21C	0.9800
C2—C3	1.3724 (17)	C22—H22	0.9500
C2—H2	0.9500	C23—C24	1.5246 (18)
C3—C4	1.4229 (17)	C23—H23A	0.9900
C4—C5	1.3619 (17)	C23—H23B	0.9900
C4—H4	0.9500	C24—H24A	0.9900
C5—C6	1.4207 (17)	C24—H24B	0.9900
C5—H5	0.9500	C25—C26	1.5177 (17)
C6—C8	1.4096 (17)	C25—H25A	0.9900
C7—H7A	0.9800	C25—H25B	0.9900
C7—H7B	0.9800	C26—H26A	0.9900
C7—H7C	0.9800	C26—H26B	0.9900
C8—H8	0.9500	C27—C28	1.5138 (17)
C9—C10	1.5231 (16)	C27—H27A	0.9900
C9—H9A	0.9900	C27—H27B	0.9900
C9—H9B	0.9900	C28—H28A	0.9900
C10—H10A	0.9900	C28—H28B	0.9900

C3—O2—C7	117.10 (10)	C14—C13—H13B	109.4
C13—O3—C12	108.59 (10)	H13A—C13—H13B	108.0
C17—O5—C21	117.66 (10)	N2—C14—C13	109.57 (11)
C27—O6—C26	109.87 (9)	N2—C14—H14A	109.8
C8—N1—C9	123.55 (11)	C13—C14—H14A	109.8
C8—N1—H1	116.5 (12)	N2—C14—H14B	109.8
C9—N1—H1	119.9 (12)	C13—C14—H14B	109.8
C11—N2—C10	108.28 (10)	H14A—C14—H14B	108.2
C11—N2—C14	109.75 (10)	O4—C15—C16	122.00 (11)
C10—N2—C14	112.35 (10)	O4—C15—C20	121.65 (11)
C22—N3—C23	122.71 (11)	C16—C15—C20	116.34 (11)
C22—N3—H3	116.9 (11)	C17—C16—C15	121.19 (11)
C23—N3—H3	120.4 (11)	C17—C16—H16	119.4
C24—N4—C28	109.97 (9)	C15—C16—H16	119.4
C24—N4—C25	111.83 (9)	O5—C17—C16	124.99 (11)
C28—N4—C25	108.10 (10)	O5—C17—C18	113.13 (11)
O1—C1—C2	121.77 (11)	C16—C17—C18	121.87 (11)
O1—C1—C6	121.36 (11)	C19—C18—C17	118.51 (11)
C2—C1—C6	116.85 (11)	C19—C18—H18	120.7
C3—C2—C1	120.63 (11)	C17—C18—H18	120.7
C3—C2—H2	119.7	C18—C19—C20	122.08 (11)
C1—C2—H2	119.7	C18—C19—H19	119.0
O2—C3—C2	124.61 (11)	C20—C19—H19	119.0
O2—C3—C4	113.45 (10)	C22—C20—C19	118.70 (11)
C2—C3—C4	121.95 (11)	C22—C20—C15	121.32 (11)
C5—C4—C3	119.04 (11)	C19—C20—C15	119.98 (11)
C5—C4—H4	120.5	O5—C21—H21A	109.5
C3—C4—H4	120.5	O5—C21—H21B	109.5
C4—C5—C6	121.45 (11)	H21A—C21—H21B	109.5
C4—C5—H5	119.3	O5—C21—H21C	109.5
C6—C5—H5	119.3	H21A—C21—H21C	109.5
C8—C6—C5	119.15 (11)	H21B—C21—H21C	109.5
C8—C6—C1	120.63 (11)	N3—C22—C20	125.90 (12)
C5—C6—C1	120.06 (11)	N3—C22—H22	117.1
O2—C7—H7A	109.5	C20—C22—H22	117.1
O2—C7—H7B	109.5	N3—C23—C24	109.88 (10)
H7A—C7—H7B	109.5	N3—C23—H23A	109.7
O2—C7—H7C	109.5	C24—C23—H23A	109.7
H7A—C7—H7C	109.5	N3—C23—H23B	109.7
H7B—C7—H7C	109.5	C24—C23—H23B	109.7
N1—C8—C6	125.19 (11)	H23A—C23—H23B	108.2
N1—C8—H8	117.4	N4—C24—C23	113.23 (10)
C6—C8—H8	117.4	N4—C24—H24A	108.9
N1—C9—C10	110.56 (10)	C23—C24—H24A	108.9
N1—C9—H9A	109.5	N4—C24—H24B	108.9
C10—C9—H9A	109.5	C23—C24—H24B	108.9
N1—C9—H9B	109.5	H24A—C24—H24B	107.7
C10—C9—H9B	109.5	N4—C25—C26	110.72 (10)
H9A—C9—H9B	108.1	N4—C25—H25A	109.5
N2—C10—C9	111.97 (10)	C26—C25—H25A	109.5
N2—C10—H10A	109.2	N4—C25—H25B	109.5
C9—C10—H10A	109.2	C26—C25—H25B	109.5
N2—C10—H10B	109.2	H25A—C25—H25B	108.1
C9—C10—H10B	109.2	O6—C26—C25	111.69 (10)
H10A—C10—H10B	107.9	O6—C26—H26A	109.3
N2—C11—C12	111.64 (11)	C25—C26—H26A	109.3
N2—C11—H11A	109.3	O6—C26—H26B	109.3
C12—C11—H11A	109.3	C25—C26—H26B	109.3
N2—C11—H11B	109.3	H26A—C26—H26B	107.9
C12—C11—H11B	109.3	O6—C27—C28	111.39 (10)
H11A—C11—H11B	108.0	O6—C27—H27A	109.3
O3—C12—C11	111.69 (12)	C28—C27—H27A	109.3
O3—C12—H12A	109.3	O6—C27—H27B	109.3
C11—C12—H12A	109.3	C28—C27—H27B	109.3
O3—C12—H12B	109.3	H27A—C27—H27B	108.0
C11—C12—H12B	109.3	N4—C28—C27	109.79 (10)
H12A—C12—H12B	107.9	N4—C28—H28A	109.7
O3—C13—C14	111.10 (13)	C27—C28—H28A	109.7
O3—C13—H13A	109.4	N4—C28—H28B	109.7
C14—C13—H13A	109.4	C27—C28—H28B	109.7
O3—C13—H13B	109.4	H28A—C28—H28B	108.2

O1—C1—C2—C3	179.90 (11)	O4—C15—C16—C17	−179.19 (11)
C6—C1—C2—C3	1.07 (16)	C20—C15—C16—C17	0.26 (17)
C7—O2—C3—C2	6.74 (17)	C21—O5—C17—C16	−5.24 (18)
C7—O2—C3—C4	−172.62 (10)	C21—O5—C17—C18	175.49 (10)
C1—C2—C3—O2	−178.94 (10)	C15—C16—C17—O5	179.04 (10)
C1—C2—C3—C4	0.37 (18)	C15—C16—C17—C18	−1.75 (19)
O2—C3—C4—C5	178.02 (10)	O5—C17—C18—C19	−178.74 (10)
C2—C3—C4—C5	−1.36 (18)	C16—C17—C18—C19	1.96 (18)
C3—C4—C5—C6	0.81 (17)	C17—C18—C19—C20	−0.67 (18)
C4—C5—C6—C8	−174.64 (11)	C18—C19—C20—C22	179.23 (11)
C4—C5—C6—C1	0.66 (17)	C18—C19—C20—C15	−0.77 (18)
O1—C1—C6—C8	−5.18 (17)	O4—C15—C20—C22	0.43 (19)
C2—C1—C6—C8	173.65 (11)	C16—C15—C20—C22	−179.02 (11)
O1—C1—C6—C5	179.58 (11)	O4—C15—C20—C19	−179.57 (11)
C2—C1—C6—C5	−1.58 (16)	C16—C15—C20—C19	0.98 (17)
C9—N1—C8—C6	−172.63 (11)	C23—N3—C22—C20	−177.67 (11)
C5—C6—C8—N1	177.35 (11)	C19—C20—C22—N3	−179.06 (12)
C1—C6—C8—N1	2.07 (18)	C15—C20—C22—N3	0.94 (19)
C8—N1—C9—C10	−112.86 (13)	C22—N3—C23—C24	102.47 (14)
C11—N2—C10—C9	178.68 (11)	C28—N4—C24—C23	170.73 (10)
C14—N2—C10—C9	−59.94 (14)	C25—N4—C24—C23	−69.17 (13)
N1—C9—C10—N2	−171.02 (10)	N3—C23—C24—N4	−173.15 (10)
C10—N2—C11—C12	176.04 (11)	C24—N4—C25—C26	−178.31 (10)
C14—N2—C11—C12	53.07 (15)	C28—N4—C25—C26	−57.12 (13)
C13—O3—C12—C11	59.03 (15)	C27—O6—C26—C25	−56.66 (13)
N2—C11—C12—O3	−55.80 (16)	N4—C25—C26—O6	57.23 (14)
C12—O3—C13—C14	−61.84 (15)	C26—O6—C27—C28	58.34 (13)
C11—N2—C14—C13	−54.87 (15)	C24—N4—C28—C27	−179.29 (10)
C10—N2—C14—C13	−175.41 (11)	C25—N4—C28—C27	58.37 (13)
O3—C13—C14—N2	60.70 (16)	O6—C27—C28—N4	−60.28 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.88 (1)	1.96 (1)	2.6489 (15)	133 (2)
N1—H1···O1ⁱ	0.88 (1)	2.32 (1)	2.9570 (18)	129 (1)
N3—H3···O4	0.89 (1)	2.02 (1)	2.6930 (15)	132 (1)
N3—H3···O4ⁱⁱ	0.89 (1)	2.29 (1)	2.9505 (18)	132 (1)

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

Experimental details

Crystal data
Chemical formula	C₁₄H₂₀N₂O₃
M_r	264.32
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	10.4022 (2), 10.7340 (2), 14.3497 (3)
α, β, γ (°)	83.523 (1), 74.810 (1), 60.768 (1)
V (Å³)	1349.13 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.25 × 0.25

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9402, 5948, 4990
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.122, 1.04
No. of reflections	5948
No. of parameters	353
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.28

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.88 (1)	1.96 (1)	2.6489 (15)	133 (2)
N1—H1···O1ⁱ	0.88 (1)	2.32 (1)	2.9570 (18)	129 (1)
N3—H3···O4	0.89 (1)	2.02 (1)	2.6930 (15)	132 (1)
N3—H3···O4ⁱⁱ	0.89 (1)	2.29 (1)	2.9505 (18)	132 (1)

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

Acknowledgements

The authors thank the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Petek, H., Albayrak, C., İskeleli, N. O., Ağar, E. & Şenel, I. (2005). Acta Cryst. E61, o3990–o3991. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar