supplementary materials
5-Methoxy-2-[(2-morpholinoethyl)iminiomethyl]phenolate
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.
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.
H atoms were placed at calculated positions (C—H = 0.95–0.99 Å) and
were treated as riding on their parent C atoms, with U(H) set to
1.2–1.5 times Ueq(C). The iminium H atoms were located in a
difference Fourier map, and were refined with a distance restraint of N—H =
0.88 (1) Å; their temperature factors were refined.
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).
5-Methoxy-2-[(2-morpholinoethyl)iminiomethyl]phenolate
top
Crystal data top
| C14H20N2O3 | Z = 4 |
| Mr = 264.32 | F(000) = 568 |
| Triclinic, P1 | Dx = 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 | Rint = 0.019 |
| graphite | θmax = 27.5°, θmin = 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(Fo2) + (0.0696P)2 + 0.3249P]
where P = (Fo2 + 2Fc2)/3 |
| 5948 reflections | (Δ/σ)max = 0.001 |
| 353 parameters | Δρmax = 0.31 e Å−3 |
| 2 restraints | Δρmin = −0.28 e Å−3 |
Crystal data top
| C14H20N2O3 | γ = 60.768 (1)° |
| Mr = 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 | Rint = 0.019 |
| 5948 independent reflections | θmax = 27.5° |
Refinement top
| R[F2 > 2σ(F2)] = 0.040 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.122 | Δρmax = 0.31 e Å−3 |
| S = 1.04 | Δρmin = −0.28 e Å−3 |
| 5948 reflections | Absolute structure: ? |
| 353 parameters | Flack parameter: ? |
| 2 restraints | Rogers parameter: ? |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top| | x | y | z | Uiso*/Ueq | |
| 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, °) 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, °) 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. |
Table 1
Hydrogen-bond geometry (Å, °) 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. |
The authors thank the University of Malaya for supporting this study.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Petek, H., Albayrak, C., İskeleli, N. O., Ağar, E. & Şenel, I. (2005). Acta Cryst. E61, o3990–o3991.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Westrip, S. P. (2009). publCIF. In preparation.
![[Figure 1]](./tk2422fig1thm.gif)
