Abstract
The asymmetric unit of the title compound, C30H24N2O2, contains two independent molecules, which both lie on centers of inversion. The central phenylene ring is inclined at 61.4 (2)° with respect to the flanking aromatic ring [dihedral angle = 70.7 (3)° in the second molecule].
Related literature
For the only reported crystal structure of a compound possessing a propylylamino unit, see: Steiner et al. (1999 ▶). For the structure of 1,4-bis(4-aminophenoxl)benzene, see: Shemsi et al. (2008 ▶).
Experimental
Crystal data
C30H24N2O2
M r = 444.51
Triclinic,
a = 9.8766 (7) Å
b = 11.1635 (6) Å
c = 12.1531 (9) Å
α = 68.687 (6)°
β = 69.601 (7)°
γ = 88.529 (5)°
V = 1162.19 (13) Å3
Z = 2
Mo Kα radiation
μ = 0.08 mm−1
T = 100 K
0.30 × 0.10 × 0.05 mm
Data collection
Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.712, T max = 1.000
9192 measured reflections
5142 independent reflections
3245 reflections with I > 2σ(I)
R int = 0.051
Refinement
R[F 2 > 2σ(F 2)] = 0.063
wR(F 2) = 0.172
S = 1.06
5142 reflections
323 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρmax = 0.24 e Å−3
Δρmin = −0.33 e Å−3
Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 2010 ▶).
Supplementary Material
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811003862/jh2263sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003862/jh2263Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
We thank the Higher Education Commission of Pakistan and the University of Malaya for supporting this study.
supplementary crystallographic information
Comment
1,4-Bis(4-aminophenoxy)benzene is a precusor for the synthesis of polyamides owing the functional amino –NH2 group that will condense with carboxylic acids (Shemsi et al., 2008). The amino group can be also converted to a dialkylamino group by reaction with an alkyl halide in the presence of potassium carbonate. This strategy is used for the synthesis of the nitrogen–propargyl bond. The unit cell has two independent molecules of C30H24N2O2 (Scheme I) that both lie on a center-of-inversion (Fig. 1). The central phenylene ring is aligned at 61.4 (2) ° with respect to the flanking aromatic ring (the dihedral angle is 70.7 (3) ° for the second molecule). There is only one reported example of the nitrogen-parpargyl bond (Steiner et al., 1999).
Experimental
1,4-Bis(4-aminophenoxy)benzene (1 g, 2.2 mmol) was dissolved in ethanl (30 ml) followed by the addition of potassium carbonate (3 g, 21 mmol). The mixture was heated for 1 h. Propargyl bromide (1.5 ml, 15 mmol) was added and the heating was continued for another 8 h. The solvent was evaporated under reduced pressure and the residue was dissolved in a mixture of water (50 ml) and dichloromethane (50 ml). The aqueous layer was extracted three times with dichloromethane and concentrated. The product was recrystallized from ethanol; yield 60%.
Refinement
Carbon-bound H-atoms were placed in calculated positions [C—H 0.95 to 0.99 Å, Uiso(H) 1.2Ueq(C)] and were included in the refinement in the riding model approximation.
The acetylenic H-atoms were located in a difference Fourier map, and were refined with a distance restraint of C–H 0.95±0.01 Å; their temperature factors were refined.
Figures
Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C30H24N2O2 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Crystal data
| C30H24N2O2 | Z = 2 |
| Mr = 444.51 | F(000) = 468 |
| Triclinic, P1 | Dx = 1.270 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 9.8766 (7) Å | Cell parameters from 2448 reflections |
| b = 11.1635 (6) Å | θ = 2.2–29.2° |
| c = 12.1531 (9) Å | µ = 0.08 mm−1 |
| α = 68.687 (6)° | T = 100 K |
| β = 69.601 (7)° | Prism, colorless |
| γ = 88.529 (5)° | 0.30 × 0.10 × 0.05 mm |
| V = 1162.19 (13) Å3 |
Data collection
| Agilent SuperNova Dual diffractometer with an Atlas detector | 5142 independent reflections |
| Radiation source: SuperNova (Mo) X-ray Source | 3245 reflections with I > 2σ(I) |
| Mirror | Rint = 0.051 |
| Detector resolution: 10.4041 pixels mm-1 | θmax = 27.5°, θmin = 2.2° |
| ω scans | h = −12→12 |
| Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) | k = −12→14 |
| Tmin = 0.712, Tmax = 1.000 | l = −13→15 |
| 9192 measured reflections |
Refinement
| 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)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.172 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.06 | w = 1/[σ2(Fo2) + (0.0626P)2] where P = (Fo2 + 2Fc2)/3 |
| 5142 reflections | (Δ/σ)max = 0.001 |
| 323 parameters | Δρmax = 0.24 e Å−3 |
| 4 restraints | Δρmin = −0.33 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.51131 (17) | 0.20860 (14) | 0.78479 (13) | 0.0252 (4) | |
| O2 | 1.00539 (17) | 0.19216 (14) | 0.77617 (13) | 0.0247 (4) | |
| N1 | 0.7243 (2) | 0.72196 (18) | 0.64767 (16) | 0.0242 (5) | |
| N2 | 1.2235 (2) | 0.70018 (18) | 0.65456 (17) | 0.0240 (5) | |
| C1 | 0.6093 (2) | −0.0128 (2) | 1.0493 (2) | 0.0223 (5) | |
| H1 | 0.6838 | −0.0217 | 1.0835 | 0.027* | |
| C2 | 0.6174 (2) | 0.0957 (2) | 0.9431 (2) | 0.0243 (5) | |
| H2 | 0.6977 | 0.1611 | 0.9038 | 0.029* | |
| C3 | 0.5073 (2) | 0.1073 (2) | 0.89530 (19) | 0.0211 (5) | |
| C4 | 0.5691 (2) | 0.3332 (2) | 0.7564 (2) | 0.0212 (5) | |
| C5 | 0.6303 (2) | 0.4110 (2) | 0.6295 (2) | 0.0220 (5) | |
| H5 | 0.6387 | 0.3760 | 0.5671 | 0.026* | |
| C6 | 0.6796 (2) | 0.5397 (2) | 0.5924 (2) | 0.0216 (5) | |
| H6 | 0.7206 | 0.5927 | 0.5047 | 0.026* | |
| C7 | 0.6698 (2) | 0.5927 (2) | 0.68269 (19) | 0.0205 (5) | |
| C8 | 0.6062 (2) | 0.5121 (2) | 0.8109 (2) | 0.0225 (5) | |
| H8 | 0.5976 | 0.5460 | 0.8739 | 0.027* | |
| C9 | 0.5554 (2) | 0.3838 (2) | 0.8474 (2) | 0.0232 (5) | |
| H9 | 0.5114 | 0.3308 | 0.9348 | 0.028* | |
| C10 | 0.7819 (3) | 0.8070 (2) | 0.5142 (2) | 0.0249 (5) | |
| H10A | 0.8515 | 0.7620 | 0.4663 | 0.030* | |
| H10B | 0.8367 | 0.8851 | 0.5052 | 0.030* | |
| C11 | 0.6713 (3) | 0.8483 (2) | 0.4560 (2) | 0.0257 (5) | |
| C12 | 0.5809 (3) | 0.8773 (3) | 0.4114 (2) | 0.0346 (6) | |
| C13 | 0.6654 (3) | 0.7857 (2) | 0.7376 (2) | 0.0264 (6) | |
| H13A | 0.5603 | 0.7558 | 0.7841 | 0.032* | |
| H13B | 0.6760 | 0.8803 | 0.6901 | 0.032* | |
| C14 | 0.7383 (3) | 0.7593 (2) | 0.8296 (2) | 0.0280 (6) | |
| C15 | 0.7930 (3) | 0.7348 (3) | 0.9058 (3) | 0.0416 (7) | |
| C16 | 1.0318 (2) | −0.1219 (2) | 1.0003 (2) | 0.0219 (5) | |
| H16 | 1.0540 | −0.2052 | 1.0006 | 0.026* | |
| C17 | 1.0369 (2) | −0.0226 (2) | 0.8889 (2) | 0.0231 (5) | |
| H17 | 1.0618 | −0.0381 | 0.8128 | 0.028* | |
| C18 | 1.0058 (2) | 0.0986 (2) | 0.88900 (19) | 0.0212 (5) | |
| C19 | 1.0600 (2) | 0.3185 (2) | 0.74796 (19) | 0.0212 (5) | |
| C20 | 0.9869 (2) | 0.4191 (2) | 0.69923 (19) | 0.0236 (5) | |
| H20 | 0.9004 | 0.4016 | 0.6876 | 0.028* | |
| C21 | 1.0402 (2) | 0.5458 (2) | 0.6673 (2) | 0.0244 (5) | |
| H21 | 0.9900 | 0.6148 | 0.6333 | 0.029* | |
| C22 | 1.1676 (2) | 0.5732 (2) | 0.68473 (19) | 0.0204 (5) | |
| C23 | 1.2417 (2) | 0.4694 (2) | 0.73047 (19) | 0.0220 (5) | |
| H23 | 1.3296 | 0.4859 | 0.7406 | 0.026* | |
| C24 | 1.1894 (2) | 0.3433 (2) | 0.76112 (19) | 0.0222 (5) | |
| H24 | 1.2416 | 0.2740 | 0.7910 | 0.027* | |
| C25 | 1.1369 (3) | 0.8061 (2) | 0.6209 (2) | 0.0268 (6) | |
| H25A | 1.1674 | 0.8791 | 0.6381 | 0.032* | |
| H25B | 1.0332 | 0.7765 | 0.6748 | 0.032* | |
| C26 | 1.1529 (2) | 0.8513 (2) | 0.4870 (2) | 0.0239 (5) | |
| C27 | 1.1667 (3) | 0.8879 (2) | 0.3791 (2) | 0.0323 (6) | |
| C28 | 1.3208 (3) | 0.7176 (2) | 0.7156 (2) | 0.0273 (6) | |
| H28A | 1.3485 | 0.8115 | 0.6881 | 0.033* | |
| H28B | 1.4106 | 0.6782 | 0.6865 | 0.033* | |
| C29 | 1.2574 (3) | 0.6603 (2) | 0.8560 (2) | 0.0308 (6) | |
| C30 | 1.2069 (4) | 0.6076 (3) | 0.9671 (3) | 0.0454 (8) | |
| H12 | 0.506 (2) | 0.895 (3) | 0.377 (2) | 0.055 (9)* | |
| H15 | 0.838 (3) | 0.720 (3) | 0.966 (2) | 0.055 (9)* | |
| H27 | 1.177 (3) | 0.911 (3) | 0.2929 (12) | 0.059 (9)* | |
| H30 | 1.167 (3) | 0.570 (3) | 1.0577 (10) | 0.075 (11)* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0315 (9) | 0.0200 (8) | 0.0219 (9) | 0.0000 (7) | −0.0140 (7) | −0.0015 (6) |
| O2 | 0.0334 (9) | 0.0205 (9) | 0.0209 (9) | 0.0019 (7) | −0.0148 (7) | −0.0039 (6) |
| N1 | 0.0316 (11) | 0.0219 (10) | 0.0180 (10) | 0.0034 (9) | −0.0101 (8) | −0.0054 (8) |
| N2 | 0.0283 (11) | 0.0203 (10) | 0.0230 (10) | 0.0053 (9) | −0.0135 (9) | −0.0039 (8) |
| C1 | 0.0214 (12) | 0.0224 (12) | 0.0256 (12) | 0.0055 (10) | −0.0126 (10) | −0.0082 (9) |
| C2 | 0.0210 (12) | 0.0222 (12) | 0.0249 (13) | −0.0025 (10) | −0.0069 (10) | −0.0049 (9) |
| C3 | 0.0226 (12) | 0.0210 (12) | 0.0184 (12) | 0.0029 (10) | −0.0088 (10) | −0.0046 (9) |
| C4 | 0.0198 (11) | 0.0215 (12) | 0.0211 (12) | 0.0029 (10) | −0.0100 (9) | −0.0043 (9) |
| C5 | 0.0223 (12) | 0.0249 (13) | 0.0209 (12) | 0.0063 (10) | −0.0095 (10) | −0.0099 (9) |
| C6 | 0.0223 (12) | 0.0245 (12) | 0.0153 (11) | 0.0063 (10) | −0.0068 (9) | −0.0049 (9) |
| C7 | 0.0195 (11) | 0.0203 (12) | 0.0197 (12) | 0.0059 (10) | −0.0094 (9) | −0.0035 (9) |
| C8 | 0.0222 (12) | 0.0275 (13) | 0.0201 (12) | 0.0089 (10) | −0.0105 (10) | −0.0094 (9) |
| C9 | 0.0209 (12) | 0.0263 (13) | 0.0169 (12) | 0.0039 (10) | −0.0061 (9) | −0.0029 (9) |
| C10 | 0.0272 (13) | 0.0220 (12) | 0.0232 (12) | 0.0003 (10) | −0.0094 (10) | −0.0057 (9) |
| C11 | 0.0305 (14) | 0.0217 (12) | 0.0215 (12) | 0.0025 (11) | −0.0099 (10) | −0.0038 (9) |
| C12 | 0.0382 (16) | 0.0354 (15) | 0.0340 (15) | 0.0100 (13) | −0.0195 (13) | −0.0115 (12) |
| C13 | 0.0298 (13) | 0.0209 (12) | 0.0283 (13) | 0.0044 (11) | −0.0116 (11) | −0.0081 (10) |
| C14 | 0.0234 (13) | 0.0341 (14) | 0.0246 (13) | −0.0012 (11) | −0.0039 (10) | −0.0135 (11) |
| C15 | 0.0351 (16) | 0.061 (2) | 0.0308 (15) | −0.0072 (14) | −0.0113 (13) | −0.0200 (14) |
| C16 | 0.0236 (12) | 0.0189 (12) | 0.0252 (12) | 0.0062 (10) | −0.0110 (10) | −0.0090 (9) |
| C17 | 0.0234 (12) | 0.0268 (13) | 0.0193 (12) | 0.0038 (10) | −0.0070 (10) | −0.0099 (10) |
| C18 | 0.0179 (11) | 0.0254 (13) | 0.0193 (12) | 0.0019 (10) | −0.0088 (9) | −0.0051 (9) |
| C19 | 0.0246 (12) | 0.0211 (12) | 0.0148 (11) | −0.0003 (10) | −0.0057 (9) | −0.0045 (9) |
| C20 | 0.0198 (12) | 0.0291 (13) | 0.0184 (12) | 0.0035 (10) | −0.0086 (9) | −0.0036 (9) |
| C21 | 0.0241 (12) | 0.0255 (13) | 0.0194 (12) | 0.0085 (10) | −0.0092 (10) | −0.0032 (9) |
| C22 | 0.0213 (12) | 0.0215 (12) | 0.0135 (11) | 0.0029 (10) | −0.0054 (9) | −0.0021 (9) |
| C23 | 0.0193 (12) | 0.0278 (13) | 0.0195 (12) | 0.0056 (10) | −0.0096 (9) | −0.0073 (9) |
| C24 | 0.0232 (12) | 0.0254 (13) | 0.0180 (12) | 0.0072 (10) | −0.0099 (9) | −0.0061 (9) |
| C25 | 0.0311 (14) | 0.0238 (13) | 0.0223 (12) | 0.0069 (11) | −0.0085 (10) | −0.0065 (10) |
| C26 | 0.0216 (12) | 0.0218 (12) | 0.0269 (13) | 0.0054 (10) | −0.0092 (10) | −0.0074 (10) |
| C27 | 0.0332 (15) | 0.0343 (15) | 0.0312 (16) | 0.0047 (12) | −0.0151 (12) | −0.0114 (12) |
| C28 | 0.0250 (13) | 0.0241 (13) | 0.0332 (14) | 0.0040 (10) | −0.0126 (11) | −0.0093 (10) |
| C29 | 0.0367 (14) | 0.0318 (14) | 0.0358 (16) | 0.0162 (12) | −0.0211 (12) | −0.0193 (12) |
| C30 | 0.067 (2) | 0.0478 (18) | 0.0350 (18) | 0.0323 (16) | −0.0280 (16) | −0.0231 (14) |
Geometric parameters (Å, °)
| O1—C4 | 1.391 (3) | C13—C14 | 1.472 (3) |
| O1—C3 | 1.395 (2) | C13—H13A | 0.9900 |
| O2—C18 | 1.391 (2) | C13—H13B | 0.9900 |
| O2—C19 | 1.399 (3) | C14—C15 | 1.175 (3) |
| N1—C7 | 1.410 (3) | C15—H15 | 0.95 (1) |
| N1—C10 | 1.457 (3) | C16—C18ii | 1.384 (3) |
| N1—C13 | 1.463 (3) | C16—C17 | 1.389 (3) |
| N2—C22 | 1.404 (3) | C16—H16 | 0.9500 |
| N2—C28 | 1.458 (3) | C17—C18 | 1.380 (3) |
| N2—C25 | 1.461 (3) | C17—H17 | 0.9500 |
| C1—C3i | 1.378 (3) | C18—C16ii | 1.384 (3) |
| C1—C2 | 1.391 (3) | C19—C20 | 1.380 (3) |
| C1—H1 | 0.9500 | C19—C24 | 1.388 (3) |
| C2—C3 | 1.384 (3) | C20—C21 | 1.388 (3) |
| C2—H2 | 0.9500 | C20—H20 | 0.9500 |
| C3—C1i | 1.378 (3) | C21—C22 | 1.405 (3) |
| C4—C5 | 1.379 (3) | C21—H21 | 0.9500 |
| C4—C9 | 1.381 (3) | C22—C23 | 1.399 (3) |
| C5—C6 | 1.385 (3) | C23—C24 | 1.382 (3) |
| C5—H5 | 0.9500 | C23—H23 | 0.9500 |
| C6—C7 | 1.399 (3) | C24—H24 | 0.9500 |
| C6—H6 | 0.9500 | C25—C26 | 1.467 (3) |
| C7—C8 | 1.400 (3) | C25—H25A | 0.9900 |
| C8—C9 | 1.385 (3) | C25—H25B | 0.9900 |
| C8—H8 | 0.9500 | C26—C27 | 1.181 (3) |
| C9—H9 | 0.9500 | C27—H27 | 0.950 (10) |
| C10—C11 | 1.477 (3) | C28—C29 | 1.481 (3) |
| C10—H10A | 0.9900 | C28—H28A | 0.9900 |
| C10—H10B | 0.9900 | C28—H28B | 0.9900 |
| C11—C12 | 1.180 (3) | C29—C30 | 1.178 (4) |
| C12—H12 | 0.96 (1) | C30—H30 | 0.956 (10) |
| C4—O1—C3 | 120.48 (16) | C14—C13—H13B | 109.1 |
| C18—O2—C19 | 116.42 (16) | H13A—C13—H13B | 107.8 |
| C7—N1—C10 | 119.60 (18) | C15—C14—C13 | 177.7 (3) |
| C7—N1—C13 | 118.73 (18) | C14—C15—H15 | 177.1 (18) |
| C10—N1—C13 | 115.86 (18) | C18ii—C16—C17 | 119.6 (2) |
| C22—N2—C28 | 117.61 (17) | C18ii—C16—H16 | 120.2 |
| C22—N2—C25 | 119.25 (19) | C17—C16—H16 | 120.2 |
| C28—N2—C25 | 116.15 (19) | C18—C17—C16 | 119.9 (2) |
| C3i—C1—C2 | 119.6 (2) | C18—C17—H17 | 120.0 |
| C3i—C1—H1 | 120.2 | C16—C17—H17 | 120.0 |
| C2—C1—H1 | 120.2 | C17—C18—C16ii | 120.50 (19) |
| C3—C2—C1 | 119.4 (2) | C17—C18—O2 | 117.25 (19) |
| C3—C2—H2 | 120.3 | C16ii—C18—O2 | 122.1 (2) |
| C1—C2—H2 | 120.3 | C20—C19—C24 | 120.5 (2) |
| C1i—C3—C2 | 121.0 (2) | C20—C19—O2 | 118.4 (2) |
| C1i—C3—O1 | 115.80 (19) | C24—C19—O2 | 121.0 (2) |
| C2—C3—O1 | 123.04 (19) | C19—C20—C21 | 119.8 (2) |
| C5—C4—C9 | 120.1 (2) | C19—C20—H20 | 120.1 |
| C5—C4—O1 | 116.31 (19) | C21—C20—H20 | 120.1 |
| C9—C4—O1 | 123.34 (19) | C20—C21—C22 | 120.8 (2) |
| C4—C5—C6 | 120.4 (2) | C20—C21—H21 | 119.6 |
| C4—C5—H5 | 119.8 | C22—C21—H21 | 119.6 |
| C6—C5—H5 | 119.8 | C23—C22—N2 | 119.9 (2) |
| C5—C6—C7 | 120.7 (2) | C23—C22—C21 | 118.0 (2) |
| C5—C6—H6 | 119.7 | N2—C22—C21 | 122.11 (19) |
| C7—C6—H6 | 119.7 | C24—C23—C22 | 121.2 (2) |
| C6—C7—C8 | 117.8 (2) | C24—C23—H23 | 119.4 |
| C6—C7—N1 | 121.92 (19) | C22—C23—H23 | 119.4 |
| C8—C7—N1 | 120.2 (2) | C23—C24—C19 | 119.6 (2) |
| C9—C8—C7 | 121.2 (2) | C23—C24—H24 | 120.2 |
| C9—C8—H8 | 119.4 | C19—C24—H24 | 120.2 |
| C7—C8—H8 | 119.4 | N2—C25—C26 | 112.17 (19) |
| C4—C9—C8 | 119.8 (2) | N2—C25—H25A | 109.2 |
| C4—C9—H9 | 120.1 | C26—C25—H25A | 109.2 |
| C8—C9—H9 | 120.1 | N2—C25—H25B | 109.2 |
| N1—C10—C11 | 114.87 (19) | C26—C25—H25B | 109.2 |
| N1—C10—H10A | 108.5 | H25A—C25—H25B | 107.9 |
| C11—C10—H10A | 108.5 | C27—C26—C25 | 179.6 (3) |
| N1—C10—H10B | 108.5 | C26—C27—H27 | 175.8 (18) |
| C11—C10—H10B | 108.5 | N2—C28—C29 | 113.99 (19) |
| H10A—C10—H10B | 107.5 | N2—C28—H28A | 108.8 |
| C12—C11—C10 | 177.9 (3) | C29—C28—H28A | 108.8 |
| C11—C12—H12 | 176.0 (17) | N2—C28—H28B | 108.8 |
| N1—C13—C14 | 112.7 (2) | C29—C28—H28B | 108.8 |
| N1—C13—H13A | 109.1 | H28A—C28—H28B | 107.6 |
| C14—C13—H13A | 109.1 | C30—C29—C28 | 176.1 (3) |
| N1—C13—H13B | 109.1 | C29—C30—H30 | 177 (2) |
| C3i—C1—C2—C3 | 0.5 (4) | C18ii—C16—C17—C18 | 0.6 (4) |
| C1—C2—C3—C1i | −0.5 (4) | C16—C17—C18—C16ii | −0.6 (4) |
| C1—C2—C3—O1 | −175.8 (2) | C16—C17—C18—O2 | −176.80 (19) |
| C4—O1—C3—C1i | 146.9 (2) | C19—O2—C18—C17 | −142.9 (2) |
| C4—O1—C3—C2 | −37.5 (3) | C19—O2—C18—C16ii | 41.0 (3) |
| C3—O1—C4—C5 | 151.1 (2) | C18—O2—C19—C20 | −138.0 (2) |
| C3—O1—C4—C9 | −35.0 (3) | C18—O2—C19—C24 | 45.9 (3) |
| C9—C4—C5—C6 | 0.6 (3) | C24—C19—C20—C21 | −2.3 (3) |
| O1—C4—C5—C6 | 174.64 (18) | O2—C19—C20—C21 | −178.41 (18) |
| C4—C5—C6—C7 | 0.8 (3) | C19—C20—C21—C22 | −0.4 (3) |
| C5—C6—C7—C8 | −1.3 (3) | C28—N2—C22—C23 | −23.4 (3) |
| C5—C6—C7—N1 | 177.5 (2) | C25—N2—C22—C23 | −173.04 (19) |
| C10—N1—C7—C6 | 5.2 (3) | C28—N2—C22—C21 | 158.4 (2) |
| C13—N1—C7—C6 | 157.2 (2) | C25—N2—C22—C21 | 8.8 (3) |
| C10—N1—C7—C8 | −176.13 (19) | C20—C21—C22—C23 | 2.4 (3) |
| C13—N1—C7—C8 | −24.1 (3) | C20—C21—C22—N2 | −179.4 (2) |
| C6—C7—C8—C9 | 0.5 (3) | N2—C22—C23—C24 | 179.92 (19) |
| N1—C7—C8—C9 | −178.26 (19) | C21—C22—C23—C24 | −1.8 (3) |
| C5—C4—C9—C8 | −1.3 (3) | C22—C23—C24—C19 | −0.8 (3) |
| O1—C4—C9—C8 | −174.98 (19) | C20—C19—C24—C23 | 2.9 (3) |
| C7—C8—C9—C4 | 0.8 (3) | O2—C19—C24—C23 | 178.92 (18) |
| C7—N1—C10—C11 | 72.2 (3) | C22—N2—C25—C26 | −82.9 (2) |
| C13—N1—C10—C11 | −80.6 (3) | C28—N2—C25—C26 | 127.0 (2) |
| C7—N1—C13—C14 | 85.2 (2) | C22—N2—C28—C29 | −56.4 (3) |
| C10—N1—C13—C14 | −121.7 (2) | C25—N2—C28—C29 | 94.1 (2) |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+2, −y, −z+2.
Hydrogen-bond geometry (Å, °)
| D—H···A | D—H | H···A | D···A | D—H···A |
| C12—H12···O1iii | 0.96 (1) | 2.66 (3) | 3.263 (3) | 121 (2) |
| C27—H27···O2iv | 0.95 (1) | 2.68 (2) | 3.285 (3) | 122 (2) |
Symmetry codes: (iii) −x+1, −y+1, −z+1; (iv) −x+2, −y+1, −z+1.
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2263).
References
- Agilent (2010). CrysAlis PRO Agilent Technologies, Yarnton, England.
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- Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.
Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811003862/jh2263sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003862/jh2263Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report