1,4-Bis{4-[bis­(prop-2-yn-1-yl)amino]­phen­oxy}benzene

Shah, K.; Raza Shah, M.; Ng, S.W.

doi:10.1107/S1600536811003862

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o567

doi:10.1107/S1600536811003862

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1,4-Bis{4-[bis(prop-2-yn-1-yl)amino]phenoxy}benzene

Kiramat Shah,^a M. Raza Shah ^a and Seik Weng Ng ^b ^*

^aH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 7527, Pakistan, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 29 January 2011; accepted 30 January 2011; online 5 February 2011)

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, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.063
wR(F²) = 0.172
S = 1.06
5142 reflections
323 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811003862/jh2263sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811003862/jh2263Isup2.hkl

checkCIF report

Comment top

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).

Related literature top

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 top

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%.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₃₀H₂₄N₂O₂ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

1,4-Bis{4-[bis(prop-2-yn-1-yl)amino]phenoxy}benzene top

Crystal data top

C₃₀H₂₄N₂O₂	Z = 2
M_r = 444.51	F(000) = 468
Triclinic, P1	D_x = 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 top

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 monochromator	R_int = 0.051
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.2°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −12→14
T_min = 0.712, T_max = 1.000	l = −13→15
9192 measured reflections

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)] = 0.063	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(F_o²) + (0.0626P)²] where P = (F_o² + 2F_c²)/3
5142 reflections	(Δ/σ)_max = 0.001
323 parameters	Δρ_max = 0.24 e Å⁻³
4 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₃₀H₂₄N₂O₂	γ = 88.529 (5)°
M_r = 444.51	V = 1162.19 (13) Å³
Triclinic, P1	Z = 2
a = 9.8766 (7) Å	Mo Kα radiation
b = 11.1635 (6) Å	µ = 0.08 mm⁻¹
c = 12.1531 (9) Å	T = 100 K
α = 68.687 (6)°	0.30 × 0.10 × 0.05 mm
β = 69.601 (7)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5142 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	3245 reflections with I > 2σ(I)
T_min = 0.712, T_max = 1.000	R_int = 0.051
9192 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	4 restraints
wR(F²) = 0.172	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.24 e Å⁻³
5142 reflections	Δρ_min = −0.33 e Å⁻³
323 parameters

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

	x	y	z	U_iso*/U_eq
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) top

	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, º) top

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, º) top

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···O2^iv	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.

Experimental details

Crystal data
Chemical formula	C₃₀H₂₄N₂O₂
M_r	444.51
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.8766 (7), 11.1635 (6), 12.1531 (9)
α, β, γ (°)	68.687 (6), 69.601 (7), 88.529 (5)
V (Å³)	1162.19 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.10 × 0.05

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.712, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9192, 5142, 3245
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.172, 1.06
No. of reflections	5142
No. of parameters	323
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.33

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

We thank the Higher Education Commission of Pakistan and the University of Malaya for supporting this study.

References

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