Bis{4-[(1,3-benzodioxol-5-yl)meth­yl]piperazin-1-yl}methane

Kavitha, C.N.; Jasinski, J.P.; Anderson, B.J.; Yathirajan, H.S.; Kaur, M.

doi:10.1107/S1600536813028109

organic compounds

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ISSN: 2056-9890

Volume 69| Part 11| November 2013| Page o1669

doi:10.1107/S1600536813028109

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Bis{4-[(1,3-benzodioxol-5-yl)methyl]piperazin-1-yl}methane

Channappa N. Kavitha,^a Jerry P. Jasinski,^b ^* Brian J. Anderson,^b H. S. Yathirajan ^a and Manpreet Kaur ^a

^aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
^*Correspondence e-mail: jjasinski@keene.edu

(Received 10 October 2013; accepted 13 October 2013; online 19 October 2013)

In the title compound, C₂₅H₃₂N₄O₄, both piperazine rings adopt a chair conformation. One of dioxolane ring systems is essentially planar [dihedral angle = 0.9 (2)°] while the other adopts a slightly disordered envelope conformation, the mean plane of the dioxolane ring being twisted by 3.6 (2)° from that of the benzene ring. The dihedral angle between the benzene rings is 69.9 (5)°. No classical hydrogen bonds were observed.

CCDC reference: 966213

Related literature

For the biological activity of piperazines, see: Choudhary et al. (2006 ); Kharb et al. (2012 ); Millan et al. (2001 ); Brockunier et al. (2004 ); Bogatcheva et al. (2006 ); Elliott (2011 ). For related structures, see: Capuano et al. (2000 ). For puckering parameters, see Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₅H₃₂N₄O₄
M_r = 452.55
Orthorhombic, P n 2₁ a
a = 38.8025 (10) Å
b = 9.7675 (2) Å
c = 6.09571 (13) Å
V = 2310.29 (10) Å³
Z = 4
Cu Kα radiation
μ = 0.72 mm⁻¹
T = 173 K
0.38 × 0.21 × 0.11 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ) T_min = 0.836, T_max = 1.000
13559 measured reflections
4199 independent reflections
3869 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.108
S = 1.02
4199 reflections
307 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.17 e Å⁻³
Absolute structure: Flack parameter determined using 1513 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons & Flack, 2004 )
Absolute structure parameter: −0.03 (15)

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

CCDC reference: 966213

Crystal structure: contains datablock I. DOI: 10.1107/S1600536813028109/fj2646sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813028109/fj2646Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813028109/fj2646Isup3.cml

checkCIF report

Comment top

1-(3,4-Methylenedioxybenzyl)piperazine or 1-piperonylpiperazine is a psychoactive drug of the piperazine class and is used to synthesise the drug, piribedil, an antiparkinsonian agent (Millan et al., 2001). The piperazine moiety is extensively employed to construct various bioactive molecules with anti-bacterial, antimalarial activity and as antipsychotic agents (Choudhary et al., 2006). A valuable insight into recent advances on antimicrobial activity of piperazine derivatives is reported (Kharb et al., 2012). Piperazines are among the most important building blocks in today's drug discovery and are found in biologically active compounds across a number of different therapeutic areas (Brockunier et al., 2004; Bogatcheva et al., 2006). A review on the current pharmacological and toxicological information for piperazine derivatives is described (Elliott, 2011). The crystal structure of N-piperonyl analogue of the atypical antipsychotic clozapine (Capuano et al., 2000) is reported. In view of the above importance of piperonyl piperazines, this paper reports the crystal structure of the title compound, (I), C₂₅H₃₂N₄O₄, an unexpected product obtained during crystallization.

The title compound, (I), C₂₅H₃₂N₄O₄, crystallizes with one independent molecule in the asymmetric unit (Fig. 1). In the molecule, both piperazine rings adopt chair conformations (puckering parameters (N1/C2/C3/N2/C4/C5) Q, θ, and ϕ = 0.590 (3)Å, 0.0 (3)° and 173 (23)°; (N3/C14/C15/N4/C16/C17) Q, θ, and ϕ = 0.586 (3)Å, 0.7 (3)° and 182 (10)°,respectively (Cremer & Pople, 1975). One of the two five-membered dioxolane rings is planar while the other is in a slightly disordered envelope conformation (ϕ = 331.0 (18)°) where the mean plane of the dioxolane ring is twisted by 3.6 (1)° from that of the benzene ring. The dihedral angle between the mean planes of the two benzene rings is 69.9 (5)°. No classical hydrogen bonds were observed.

Related literature top

For the biological activity of piperazines, see: Choudhary et al. (2006); Kharb et al. (2012); Millan et al. (2001); Brockunier et al. (2004); Bogatcheva et al. (2006); Elliott (2011). For related structures, see: Capuano et al. (2000). For puckering parameters, see Cremer & Pople (1975).

Experimental top

0.5 g of 1-piperonylpiperazine (Sigma-Aldrich) was dissolved in 5 ml of methanol at 333 K with stirring for 10 min and left for slow evaporation. After two days, crystal formation was not observed. For the same compound, 5 ml of dimethyl formamide was added at 333 K with stirring for 15 min and left for slow evaporation. X-ray quality crystals were obtained and were used as such (m.p.: 308-312 K.)

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

Fig. 1. ORTEP drawing of (I) (C₂₅H₃₂N₄O₄) showing the labeling scheme with 30% probability displacement ellipsoids.

Bis{4-[(1,3-benzodioxol-5-yl)methyl]piperazin-1-yl}methane top

Crystal data top

C₂₅H₃₂N₄O₄	D_x = 1.312 Mg m⁻³
M_r = 452.55	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pn2₁a	Cell parameters from 5154 reflections
a = 38.8025 (10) Å	θ = 4.5–72.4°
b = 9.7675 (2) Å	µ = 0.72 mm⁻¹
c = 6.09571 (13) Å	T = 173 K
V = 2310.29 (10) Å³	Irregular, colourless
Z = 4	0.38 × 0.21 × 0.11 mm
F(000) = 968

Data collection top

Agilent Xcalibur (Eos, Gemini) diffractometer	4199 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3869 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm^-1	R_int = 0.046
ω scans	θ_max = 72.6°, θ_min = 4.6°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	h = −43→48
T_min = 0.836, T_max = 1.000	k = −11→12
13559 measured reflections	l = −5→7

Refinement top

Refinement on F²	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0485P)² + 0.6698P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.041	(Δ/σ)_max < 0.001
wR(F²) = 0.108	Δρ_max = 0.22 e Å⁻³
S = 1.02	Δρ_min = −0.17 e Å⁻³
4199 reflections	Extinction correction: SHELXL2012 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
307 parameters	Extinction coefficient: 0.0016 (2)
1 restraint	Absolute structure: Flack parameter determined using 1513 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004)
Hydrogen site location: mixed	Absolute structure parameter: −0.03 (15)

Crystal data top

C₂₅H₃₂N₄O₄	V = 2310.29 (10) Å³
M_r = 452.55	Z = 4
Orthorhombic, Pn2₁a	Cu Kα radiation
a = 38.8025 (10) Å	µ = 0.72 mm⁻¹
b = 9.7675 (2) Å	T = 173 K
c = 6.09571 (13) Å	0.38 × 0.21 × 0.11 mm

Data collection top

Agilent Xcalibur (Eos, Gemini) diffractometer	4199 independent reflections
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	3869 reflections with I > 2σ(I)
T_min = 0.836, T_max = 1.000	R_int = 0.046
13559 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.108	Δρ_max = 0.22 e Å⁻³
S = 1.02	Δρ_min = −0.17 e Å⁻³
4199 reflections	Absolute structure: Flack parameter determined using 1513 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004)
307 parameters	Absolute structure parameter: −0.03 (15)
1 restraint

Special details top

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

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

	x	y	z	U_iso*/U_eq
O1	0.31516 (6)	0.5691 (3)	1.0003 (4)	0.0425 (5)
O2	0.31379 (7)	0.7799 (3)	0.8258 (4)	0.0534 (7)
O3	0.75845 (6)	0.5660 (3)	0.1266 (4)	0.0452 (6)
O4	0.77389 (6)	0.4101 (3)	−0.1424 (4)	0.0431 (6)
N1	0.50857 (6)	0.5885 (3)	0.2715 (4)	0.0316 (6)
N2	0.43489 (6)	0.5829 (3)	0.2856 (4)	0.0283 (5)
N3	0.56439 (6)	0.5613 (3)	0.1084 (4)	0.0305 (5)
N4	0.62717 (6)	0.6657 (3)	−0.0775 (4)	0.0287 (5)
C0AA	0.54264 (8)	0.5299 (4)	0.2949 (5)	0.0359 (7)
C2	0.48991 (8)	0.5896 (4)	0.4788 (5)	0.0388 (8)
H2A	0.5031	0.6394	0.5879	0.047*
H2B	0.4868	0.4965	0.5306	0.047*
C3	0.45513 (8)	0.6567 (4)	0.4487 (5)	0.0363 (7)
H3A	0.4429	0.6576	0.5875	0.044*
H3B	0.4583	0.7508	0.4018	0.044*
C4	0.45353 (7)	0.5831 (4)	0.0781 (4)	0.0320 (6)
H4A	0.4566	0.6766	0.0279	0.038*
H4B	0.4403	0.5341	−0.0317	0.038*
C5	0.48843 (8)	0.5158 (3)	0.1056 (5)	0.0335 (7)
H5A	0.4854	0.4211	0.1496	0.040*
H5B	0.5007	0.5169	−0.0332	0.040*
C6	0.40051 (8)	0.6420 (3)	0.2635 (5)	0.0336 (7)
H6A	0.3892	0.6021	0.1368	0.040*
H6B	0.4026	0.7397	0.2382	0.040*
C7	0.37846 (7)	0.6181 (3)	0.4645 (5)	0.0290 (6)
C8	0.37856 (7)	0.4919 (3)	0.5700 (5)	0.0291 (6)
H8	0.3930	0.4234	0.5177	0.035*
C9	0.35775 (7)	0.4641 (3)	0.7517 (5)	0.0304 (6)
H9	0.3578	0.3789	0.8197	0.036*
C10	0.33726 (7)	0.5687 (3)	0.8245 (4)	0.0297 (6)
C11	0.30024 (9)	0.7027 (4)	1.0040 (6)	0.0445 (8)
H11A	0.2754	0.6961	0.9910	0.053*
H11B	0.3056	0.7478	1.1416	0.053*
C12	0.33670 (8)	0.6945 (3)	0.7208 (5)	0.0331 (7)
C13	0.35674 (8)	0.7227 (3)	0.5419 (5)	0.0337 (7)
H13	0.3560	0.8079	0.4740	0.040*
C14	0.59693 (8)	0.4870 (3)	0.1253 (5)	0.0342 (7)
H14A	0.5924	0.3894	0.1294	0.041*
H14B	0.6085	0.5122	0.2605	0.041*
C15	0.62001 (8)	0.5196 (3)	−0.0679 (5)	0.0332 (7)
H15A	0.6415	0.4695	−0.0540	0.040*
H15B	0.6089	0.4909	−0.2027	0.040*
C16	0.59437 (7)	0.7386 (3)	−0.0990 (5)	0.0311 (6)
H16A	0.5830	0.7110	−0.2337	0.037*
H16B	0.5986	0.8364	−0.1065	0.037*
C17	0.57131 (7)	0.7078 (3)	0.0934 (5)	0.0320 (6)
H17A	0.5823	0.7388	0.2275	0.038*
H17B	0.5498	0.7570	0.0770	0.038*
C18	0.65041 (7)	0.7011 (3)	−0.2577 (5)	0.0341 (7)
H18A	0.6544	0.7991	−0.2567	0.041*
H18B	0.6395	0.6779	−0.3959	0.041*
C19	0.68447 (7)	0.6275 (3)	−0.2412 (5)	0.0310 (6)
C20	0.70492 (8)	0.6439 (4)	−0.0521 (5)	0.0333 (7)
H20	0.6987	0.7043	0.0590	0.040*
C21	0.73433 (7)	0.5672 (4)	−0.0390 (4)	0.0314 (6)
C22	0.78104 (9)	0.4551 (4)	0.0760 (6)	0.0439 (8)
H22A	0.7775	0.3806	0.1787	0.053*
H22B	0.8048	0.4848	0.0872	0.053*
C23	0.74391 (7)	0.4755 (3)	−0.2007 (5)	0.0323 (7)
C24	0.72513 (8)	0.4605 (4)	−0.3887 (5)	0.0367 (7)
H24	0.7320	0.4014	−0.4999	0.044*
C25	0.69508 (8)	0.5383 (3)	−0.4056 (5)	0.0325 (7)
H25	0.6817	0.5302	−0.5314	0.039*
H0AA	0.5513 (8)	0.564 (4)	0.426 (5)	0.031 (9)*
H0AB	0.5410 (9)	0.429 (4)	0.313 (6)	0.040 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0476 (13)	0.0446 (14)	0.0352 (11)	0.0079 (11)	0.0122 (10)	0.0003 (10)
O2	0.0654 (17)	0.0392 (15)	0.0557 (16)	0.0191 (12)	0.0233 (13)	0.0014 (12)
O3	0.0382 (12)	0.0574 (16)	0.0399 (12)	0.0129 (12)	−0.0079 (9)	−0.0052 (12)
O4	0.0318 (12)	0.0503 (14)	0.0471 (14)	0.0094 (10)	0.0022 (10)	−0.0030 (11)
N1	0.0285 (12)	0.0389 (15)	0.0275 (12)	−0.0058 (11)	−0.0001 (9)	0.0010 (11)
N2	0.0286 (12)	0.0321 (13)	0.0240 (11)	−0.0032 (10)	0.0007 (9)	−0.0009 (10)
N3	0.0267 (12)	0.0288 (13)	0.0361 (13)	−0.0029 (10)	−0.0018 (9)	0.0050 (11)
N4	0.0266 (12)	0.0259 (13)	0.0336 (13)	−0.0005 (10)	−0.0013 (9)	0.0018 (10)
C0AA	0.0338 (16)	0.0421 (19)	0.0318 (15)	−0.0032 (14)	−0.0035 (12)	0.0075 (14)
C2	0.0345 (15)	0.055 (2)	0.0270 (14)	−0.0094 (15)	−0.0037 (12)	−0.0020 (15)
C3	0.0354 (16)	0.0444 (19)	0.0290 (15)	−0.0069 (14)	0.0037 (12)	−0.0073 (13)
C4	0.0331 (15)	0.0372 (16)	0.0258 (13)	−0.0052 (13)	−0.0004 (11)	−0.0007 (13)
C5	0.0332 (15)	0.0394 (18)	0.0280 (15)	−0.0034 (13)	0.0005 (12)	−0.0041 (13)
C6	0.0344 (16)	0.0326 (16)	0.0338 (15)	0.0020 (13)	0.0008 (12)	0.0037 (13)
C7	0.0280 (13)	0.0308 (16)	0.0282 (14)	0.0000 (12)	−0.0032 (11)	−0.0020 (11)
C8	0.0259 (14)	0.0281 (16)	0.0333 (15)	0.0029 (11)	−0.0011 (11)	−0.0044 (11)
C9	0.0304 (15)	0.0276 (14)	0.0333 (16)	−0.0002 (12)	−0.0040 (12)	0.0019 (12)
C10	0.0262 (13)	0.0356 (16)	0.0273 (13)	−0.0020 (12)	−0.0006 (11)	−0.0027 (12)
C11	0.0441 (18)	0.044 (2)	0.0451 (19)	0.0063 (16)	0.0116 (15)	−0.0095 (16)
C12	0.0326 (15)	0.0330 (16)	0.0337 (15)	0.0053 (13)	−0.0020 (12)	−0.0068 (12)
C13	0.0359 (15)	0.0263 (15)	0.0387 (16)	0.0031 (13)	−0.0018 (13)	0.0010 (13)
C14	0.0326 (16)	0.0265 (15)	0.0435 (17)	−0.0010 (12)	−0.0020 (12)	0.0064 (13)
C15	0.0298 (15)	0.0261 (15)	0.0437 (17)	0.0030 (12)	0.0007 (13)	0.0031 (13)
C16	0.0299 (15)	0.0245 (15)	0.0389 (16)	0.0005 (11)	−0.0055 (12)	0.0038 (12)
C17	0.0269 (14)	0.0290 (16)	0.0401 (16)	0.0022 (12)	−0.0029 (12)	−0.0008 (13)
C18	0.0313 (15)	0.0340 (17)	0.0369 (16)	−0.0019 (13)	−0.0020 (12)	0.0048 (13)
C19	0.0292 (14)	0.0316 (15)	0.0323 (15)	−0.0042 (12)	0.0028 (11)	0.0048 (12)
C20	0.0321 (15)	0.0352 (17)	0.0325 (15)	0.0010 (13)	0.0024 (12)	−0.0015 (13)
C21	0.0313 (14)	0.0359 (16)	0.0269 (14)	−0.0035 (13)	0.0009 (11)	0.0040 (13)
C22	0.0359 (17)	0.054 (2)	0.0422 (19)	0.0114 (16)	0.0030 (14)	0.0095 (16)
C23	0.0260 (14)	0.0335 (17)	0.0374 (16)	−0.0005 (12)	0.0064 (12)	0.0051 (13)
C24	0.0326 (16)	0.0390 (17)	0.0385 (17)	−0.0052 (13)	0.0093 (13)	−0.0031 (14)
C25	0.0305 (15)	0.0373 (17)	0.0298 (15)	−0.0070 (12)	−0.0001 (11)	0.0036 (12)

Geometric parameters (Å, º) top

O1—C10	1.373 (3)	C7—C8	1.390 (4)
O1—C11	1.428 (4)	C7—C13	1.406 (4)
O2—C11	1.422 (4)	C8—H8	0.9300
O2—C12	1.377 (4)	C8—C9	1.397 (4)
O3—C21	1.377 (3)	C9—H9	0.9300
O3—C22	1.427 (4)	C9—C10	1.369 (4)
O4—C22	1.429 (4)	C10—C12	1.382 (5)
O4—C23	1.374 (4)	C11—H11A	0.9700
N1—C0AA	1.447 (4)	C11—H11B	0.9700
N1—C2	1.456 (4)	C12—C13	1.367 (4)
N1—C5	1.462 (4)	C13—H13	0.9300
N2—C3	1.458 (4)	C14—H14A	0.9700
N2—C4	1.457 (3)	C14—H14B	0.9700
N2—C6	1.460 (4)	C14—C15	1.513 (4)
N3—C0AA	1.449 (4)	C15—H15A	0.9700
N3—C14	1.460 (4)	C15—H15B	0.9700
N3—C17	1.459 (4)	C16—H16A	0.9700
N4—C15	1.455 (4)	C16—H16B	0.9700
N4—C16	1.464 (4)	C16—C17	1.505 (4)
N4—C18	1.462 (4)	C17—H17A	0.9700
C0AA—H0AA	0.93 (3)	C17—H17B	0.9700
C0AA—H0AB	0.99 (4)	C18—H18A	0.9700
C2—H2A	0.9700	C18—H18B	0.9700
C2—H2B	0.9700	C18—C19	1.508 (4)
C2—C3	1.512 (4)	C19—C20	1.409 (4)
C3—H3A	0.9700	C19—C25	1.390 (4)
C3—H3B	0.9700	C20—H20	0.9300
C4—H4A	0.9700	C20—C21	1.367 (5)
C4—H4B	0.9700	C21—C23	1.382 (4)
C4—C5	1.515 (4)	C22—H22A	0.9700
C5—H5A	0.9700	C22—H22B	0.9700
C5—H5B	0.9700	C23—C24	1.366 (5)
C6—H6A	0.9700	C24—H24	0.9300
C6—H6B	0.9700	C24—C25	1.396 (5)
C6—C7	1.512 (4)	C25—H25	0.9300

C10—O1—C11	105.5 (3)	O1—C11—H11B	109.9
C12—O2—C11	105.8 (3)	O2—C11—O1	108.8 (2)
C21—O3—C22	105.4 (3)	O2—C11—H11A	109.9
C23—O4—C22	105.2 (2)	O2—C11—H11B	109.9
C0AA—N1—C2	111.8 (2)	H11A—C11—H11B	108.3
C0AA—N1—C5	111.4 (3)	O2—C12—C10	109.7 (3)
C2—N1—C5	109.8 (2)	C13—C12—O2	128.0 (3)
C3—N2—C6	111.1 (2)	C13—C12—C10	122.4 (3)
C4—N2—C3	108.9 (2)	C7—C13—H13	121.2
C4—N2—C6	111.9 (2)	C12—C13—C7	117.5 (3)
C0AA—N3—C14	110.1 (2)	C12—C13—H13	121.2
C0AA—N3—C17	111.3 (3)	N3—C14—H14A	109.5
C14—N3—C17	109.4 (2)	N3—C14—H14B	109.5
C15—N4—C16	108.3 (2)	N3—C14—C15	110.6 (3)
C15—N4—C18	112.3 (3)	H14A—C14—H14B	108.1
C16—N4—C18	110.7 (2)	C15—C14—H14A	109.5
N1—C0AA—N3	111.8 (3)	C15—C14—H14B	109.5
N1—C0AA—H0AA	106 (2)	N4—C15—C14	110.5 (3)
N1—C0AA—H0AB	110 (2)	N4—C15—H15A	109.5
N3—C0AA—H0AA	113 (2)	N4—C15—H15B	109.5
N3—C0AA—H0AB	109 (2)	C14—C15—H15A	109.5
H0AA—C0AA—H0AB	106 (3)	C14—C15—H15B	109.5
N1—C2—H2A	109.7	H15A—C15—H15B	108.1
N1—C2—H2B	109.7	N4—C16—H16A	109.6
N1—C2—C3	110.0 (3)	N4—C16—H16B	109.6
H2A—C2—H2B	108.2	N4—C16—C17	110.5 (2)
C3—C2—H2A	109.7	H16A—C16—H16B	108.1
C3—C2—H2B	109.7	C17—C16—H16A	109.6
N2—C3—C2	110.4 (3)	C17—C16—H16B	109.6
N2—C3—H3A	109.6	N3—C17—C16	110.7 (2)
N2—C3—H3B	109.6	N3—C17—H17A	109.5
C2—C3—H3A	109.6	N3—C17—H17B	109.5
C2—C3—H3B	109.6	C16—C17—H17A	109.5
H3A—C3—H3B	108.1	C16—C17—H17B	109.5
N2—C4—H4A	109.6	H17A—C17—H17B	108.1
N2—C4—H4B	109.6	N4—C18—H18A	109.2
N2—C4—C5	110.3 (2)	N4—C18—H18B	109.2
H4A—C4—H4B	108.1	N4—C18—C19	112.2 (2)
C5—C4—H4A	109.6	H18A—C18—H18B	107.9
C5—C4—H4B	109.6	C19—C18—H18A	109.2
N1—C5—C4	110.1 (3)	C19—C18—H18B	109.2
N1—C5—H5A	109.6	C20—C19—C18	119.6 (3)
N1—C5—H5B	109.6	C25—C19—C18	120.7 (3)
C4—C5—H5A	109.6	C25—C19—C20	119.6 (3)
C4—C5—H5B	109.6	C19—C20—H20	121.5
H5A—C5—H5B	108.2	C21—C20—C19	117.1 (3)
N2—C6—H6A	109.1	C21—C20—H20	121.5
N2—C6—H6B	109.1	O3—C21—C23	109.5 (3)
N2—C6—C7	112.4 (2)	C20—C21—O3	127.9 (3)
H6A—C6—H6B	107.9	C20—C21—C23	122.6 (3)
C7—C6—H6A	109.1	O3—C22—O4	108.4 (3)
C7—C6—H6B	109.1	O3—C22—H22A	110.0
C8—C7—C6	120.7 (3)	O3—C22—H22B	110.0
C8—C7—C13	119.4 (3)	O4—C22—H22A	110.0
C13—C7—C6	119.9 (3)	O4—C22—H22B	110.0
C7—C8—H8	118.7	H22A—C22—H22B	108.4
C7—C8—C9	122.5 (3)	O4—C23—C21	110.2 (3)
C9—C8—H8	118.7	C24—C23—O4	128.2 (3)
C8—C9—H9	121.7	C24—C23—C21	121.6 (3)
C10—C9—C8	116.6 (3)	C23—C24—H24	121.6
C10—C9—H9	121.7	C23—C24—C25	116.7 (3)
O1—C10—C12	110.2 (3)	C25—C24—H24	121.6
C9—C10—O1	128.2 (3)	C19—C25—C24	122.4 (3)
C9—C10—C12	121.6 (3)	C19—C25—H25	118.8
O1—C11—H11A	109.9	C24—C25—H25	118.8

O1—C10—C12—O2	−0.7 (4)	C9—C10—C12—C13	−0.8 (5)
O1—C10—C12—C13	179.1 (3)	C10—O1—C11—O2	0.5 (3)
O2—C12—C13—C7	179.6 (3)	C10—C12—C13—C7	−0.1 (4)
O3—C21—C23—O4	1.5 (4)	C11—O1—C10—C9	179.9 (3)
O3—C21—C23—C24	−177.3 (3)	C11—O1—C10—C12	0.1 (3)
O4—C23—C24—C25	179.0 (3)	C11—O2—C12—C10	1.0 (4)
N1—C2—C3—N2	59.5 (4)	C11—O2—C12—C13	−178.8 (3)
N2—C4—C5—N1	−59.0 (3)	C12—O2—C11—O1	−0.9 (4)
N2—C6—C7—C8	−42.1 (4)	C13—C7—C8—C9	0.1 (4)
N2—C6—C7—C13	140.0 (3)	C14—N3—C0AA—N1	−173.1 (3)
N3—C14—C15—N4	59.2 (3)	C14—N3—C17—C16	57.2 (3)
N4—C16—C17—N3	−59.4 (3)	C15—N4—C16—C17	59.5 (3)
N4—C18—C19—C20	−58.0 (4)	C15—N4—C18—C19	−58.6 (3)
N4—C18—C19—C25	118.7 (3)	C16—N4—C15—C14	−59.4 (3)
C0AA—N1—C2—C3	177.7 (3)	C16—N4—C18—C19	−179.8 (3)
C0AA—N1—C5—C4	−177.6 (3)	C17—N3—C0AA—N1	65.3 (3)
C0AA—N3—C14—C15	−179.6 (3)	C17—N3—C14—C15	−56.9 (3)
C0AA—N3—C17—C16	179.1 (2)	C18—N4—C15—C14	178.0 (2)
C2—N1—C0AA—N3	−164.6 (3)	C18—N4—C16—C17	−176.9 (2)
C2—N1—C5—C4	58.0 (3)	C18—C19—C20—C21	175.4 (3)
C3—N2—C4—C5	59.2 (3)	C18—C19—C25—C24	−175.0 (3)
C3—N2—C6—C7	−69.1 (3)	C19—C20—C21—O3	179.3 (3)
C4—N2—C3—C2	−59.5 (3)	C19—C20—C21—C23	−0.8 (5)
C4—N2—C6—C7	169.0 (3)	C20—C19—C25—C24	1.7 (5)
C5—N1—C0AA—N3	72.2 (3)	C20—C21—C23—O4	−178.4 (3)
C5—N1—C2—C3	−58.2 (4)	C20—C21—C23—C24	2.9 (5)
C6—N2—C3—C2	176.9 (2)	C21—O3—C22—O4	11.6 (4)
C6—N2—C4—C5	−177.7 (3)	C21—C23—C24—C25	−2.5 (5)
C6—C7—C8—C9	−177.8 (3)	C22—O3—C21—C20	171.8 (3)
C6—C7—C13—C12	178.3 (3)	C22—O3—C21—C23	−8.1 (3)
C7—C8—C9—C10	−0.9 (4)	C22—O4—C23—C21	5.7 (4)
C8—C7—C13—C12	0.4 (4)	C22—O4—C23—C24	−175.6 (3)
C8—C9—C10—O1	−178.6 (3)	C23—O4—C22—O3	−10.7 (4)
C8—C9—C10—C12	1.2 (4)	C23—C24—C25—C19	0.2 (5)
C9—C10—C12—O2	179.4 (3)	C25—C19—C20—C21	−1.4 (4)

Experimental details

Crystal data
Chemical formula	C₂₅H₃₂N₄O₄
M_r	452.55
Crystal system, space group	Orthorhombic, Pn2₁a
Temperature (K)	173
a, b, c (Å)	38.8025 (10), 9.7675 (2), 6.09571 (13)
V (Å³)	2310.29 (10)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.72
Crystal size (mm)	0.38 × 0.21 × 0.11

Data collection
Diffractometer	Agilent Xcalibur (Eos, Gemini) diffractometer
Absorption correction	Multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)
T_min, T_max	0.836, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	13559, 4199, 3869
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.108, 1.02
No. of reflections	4199
No. of parameters	307
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.17
Absolute structure	Flack parameter determined using 1513 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004)
Absolute structure parameter	−0.03 (15)

Computer programs: CrysAlis PRO (Agilent, 2012), CrysAlis RED (Agilent, 2012), SUPERFLIP (Palatinus & Chapuis, 2007), SHELXL2012 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Acknowledgements

CNK thanks the University of Mysore for research facilities and is also grateful to the Principal, Maharani's Science College for Women in Mysore, for giving permission to do research. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

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