4-[4-(Diethyl­amino)­phen­yl]-N-methyl-3-nitro-4H-chromen-2-amine

Muthukumaran, J.; Parthiban, A.; Manivel, P.; Rao, H.S.P.; Krishna, R.

doi:10.1107/S1600536811017338

4-[4-(Diethylamino)phenyl]-N-methyl-3-nitro-4H-chromen-2-amine

J. Muthukumaran, A. Parthiban, P. Manivel, H. S. P. Rao and R. Krishna

In the title compound, C₂₀H₂₃N₃O₃, the dihydropyran ring adopts half-chair conformation. The chromene system makes a dihedral angle of 87.35 (5)° with the adjacent benzene ring. An intramolecular N-H

O hydrogen bond generates an S(6) motif, which stabilizes the molecular conformation. In the crystal, weak intermolecular C-H

O hydrogen bonds contribute to the stabilization of the packing.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811017338/sj5141sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536811017338/sj5141Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536811017338/sj5141Isup3.cml Supplementary material

CCDC reference: 828582

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.056
wR factor = 0.162
Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.45 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H    Uiso(max)/Uiso(min) ..       4.23 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C18
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          4

Alert level G
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained Atom Sites ....          3
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT793_ALERT_4_G The Model has Chirality at C7      (Verify) ....          S
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          62 Perc.

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

4H-chromenes and their derivatives possess various biological and pharmacological properties such as anti-viral, anti-fungal, anti-inflammatory, antidiabetic, cardionthonic, anti-anaphylactic and anti-cancer activity (Cai, 2008; Cai, 2007; Cai et al., 2006; Gabor,1988; Brooks,1998; Valenti et al., 1993; Hyana & Saimoto, 1987; Tang et al., 2007). 4-aryl-4H-chromenes are a new series of apoptosis inducers, which exhibit potent anticancer activity (Afantitis et al., 2006). Considering the importance of 4-aryl-4H-chromene derivatives, a single-crystal X-ray diffraction study on the title compound was carried out and analyzed.

Some 4H-chromene derivatives are already reported in the literature (Muthukumaran et al., 2011; Gayathri et al., 2006; Bhaskaran et al., 2006). The molecular structure of the title compound is shown in Fig. 1. From the puckering analysis (Cremer & Pople, 1975), the fused dihydropyran ring (O1/C1/C6/C7/C8/C9) of 4H-chromene system is very similar to half chair (H form) conformation with puckering parameters of Q = 0.253 (2) Å, θ = 103.2 (5) ° and Φ = 7.0 (5) °. In the title compound, the 4H-chromene system makes a dihedral angle of 87.35 (5)° with the adjacent phenyl ring. The intramolecular N1—H1···O2 interaction generates a graph-set motif S (6) (Bernstein et al., 1995) (Fig. 2) with a D···A bond distance of 2.596 (2) Å. The crystal packing (Fig. 3) is stabilized by weak intermolecular C—H···O interactions.

Related literature top

For the biological importance of 4H-chromene derivatives, see: Cai (2007, 2008); Cai et al. (2006); Gabor (1988); Brooks (1998); Valenti et al. (1993); Hyana & Saimoto (1987); Afantitis et al. (2006); Tang et al. (2007). For the structures of 4H-chromene derivatives, see: Muthukumaran et al. (2011); Gayathri et al. (2006); Bhaskaran et al. (2006). For ring puckering analysis, see: Cremer & Pople (1975) and for hydrogen-bond motifs, see: Bernstein et al. (1995)

Experimental top

To a vigorously stirred solution of N-methyl-N-[3-nitro-4-(methylsulfanyl)-4H-2-chromenyl]amine (0.5 g, 2 mmol) in ethanol (15 ml), N, N-diethylaminobenzene (0.33 g, 2.2 mmol) was added and the resulting solution was refluxed for 12 h by which time the reaction was complete (TLC; hexane: EtOAc, 6:4). The reaction mixture was cooled to room temperature and kept aside for 3 h. The solid, which separated was filtered to obtain 0.59 g of N2-methyl-4-[4-(diethylamino)phenyl]-3-nitro-4H-2-chromenamine in 92% yield as colorless solid; mp 201 °C. R_f 0.4 (hexane: EtOAc, 6:4). A sample suitable for single crystal X-ray analysis was obtained by recrystallization from a mixture of dichloromethane and hexane (3:1).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. : The molecular structure of (I), showing displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. : A view of intramolecular motif S (6) formed by N—H···O interaction in Compound (I). The motif forming atoms are shown in ball and stick model and the Hydrogen bond are shown in blue dashed lines.
	Fig. 3. : The crystal packing of (I) showing intermolecular interactions as dashed lines.

4-[4-(Diethylamino)phenyl]-N-methyl-3-nitro-4H-chromen-2-amine top

Crystal data top

C₂₀H₂₃N₃O₃	Z = 2
M_r = 353.41	F(000) = 376
Triclinic, P1	D_x = 1.272 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9199 (11) Å	Cell parameters from 8151 reflections
b = 10.4333 (12) Å	θ = 2.7–29.3°
c = 11.6697 (8) Å	µ = 0.09 mm⁻¹
α = 65.100 (9)°	T = 293 K
β = 82.388 (8)°	Block, yellow
γ = 69.513 (11)°	0.45 × 0.35 × 0.35 mm
V = 922.63 (19) Å³

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	3242 independent reflections
Radiation source: fine-focus sealed tube	2625 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 15.9821 pixels mm^-1	θ_max = 25.0°, θ_min = 2.7°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −12→12
T_min = 0.923, T_max = 1.000	l = −13→13
17119 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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.162	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0737P)² + 0.5254P] where P = (F_o² + 2F_c²)/3
3242 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.52 e Å⁻³
3 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₂₀H₂₃N₃O₃	γ = 69.513 (11)°
M_r = 353.41	V = 922.63 (19) Å³
Triclinic, P1	Z = 2
a = 8.9199 (11) Å	Mo Kα radiation
b = 10.4333 (12) Å	µ = 0.09 mm⁻¹
c = 11.6697 (8) Å	T = 293 K
α = 65.100 (9)°	0.45 × 0.35 × 0.35 mm
β = 82.388 (8)°

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	3242 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	2625 reflections with I > 2σ(I)
T_min = 0.923, T_max = 1.000	R_int = 0.036
17119 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	3 restraints
wR(F²) = 0.162	H-atom parameters constrained
S = 1.05	Δρ_max = 0.52 e Å⁻³
3242 reflections	Δρ_min = −0.44 e Å⁻³
226 parameters

Special details top

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
O1	0.42869 (17)	0.68371 (16)	0.57975 (15)	0.0483 (4)
N1	0.3634 (2)	0.9167 (2)	0.43607 (18)	0.0466 (5)
H1	0.3882	0.9910	0.3790	0.056*
N2	0.6967 (2)	0.8783 (2)	0.38082 (17)	0.0474 (5)
C8	0.6437 (2)	0.7689 (2)	0.47334 (19)	0.0395 (5)
C7	0.7689 (2)	0.6305 (2)	0.55805 (19)	0.0391 (5)
H7	0.8571	0.6001	0.5053	0.047*
O3	0.84395 (19)	0.8532 (2)	0.36670 (17)	0.0620 (5)
C9	0.4810 (2)	0.7932 (2)	0.4932 (2)	0.0397 (5)
O2	0.5993 (2)	1.00198 (19)	0.31188 (17)	0.0658 (5)
C6	0.6982 (2)	0.5058 (2)	0.6218 (2)	0.0399 (5)
C10	0.8361 (2)	0.6586 (2)	0.65559 (19)	0.0385 (5)
C15	0.9923 (2)	0.6551 (2)	0.6541 (2)	0.0425 (5)
H15	1.0599	0.6340	0.5919	0.051*
C1	0.5350 (3)	0.5370 (2)	0.6324 (2)	0.0424 (5)
C13	0.9558 (3)	0.7122 (3)	0.8384 (2)	0.0491 (6)
C5	0.7938 (3)	0.3569 (3)	0.6773 (2)	0.0484 (6)
H5	0.9044	0.3321	0.6705	0.058*
C11	0.7400 (3)	0.6897 (3)	0.7504 (2)	0.0482 (5)
H11	0.6339	0.6932	0.7536	0.058*
C14	1.0514 (3)	0.6821 (3)	0.7422 (2)	0.0478 (5)
H14	1.1570	0.6802	0.7373	0.057*
C12	0.7968 (3)	0.7153 (3)	0.8397 (2)	0.0544 (6)
H12	0.7288	0.7351	0.9022	0.065*
C20	0.1945 (3)	0.9377 (3)	0.4617 (3)	0.0563 (6)
H20A	0.1681	0.8589	0.4560	0.084*
H20B	0.1316	1.0323	0.4009	0.084*
H20C	0.1724	0.9357	0.5451	0.084*
N3	1.0125 (3)	0.7401 (3)	0.9267 (2)	0.0778 (5)
C2	0.4655 (3)	0.4275 (3)	0.6966 (2)	0.0527 (6)
H2	0.3548	0.4520	0.7021	0.063*
C3	0.5633 (3)	0.2813 (3)	0.7523 (3)	0.0602 (7)
H3	0.5187	0.2061	0.7971	0.072*
C4	0.7278 (3)	0.2458 (3)	0.7418 (2)	0.0584 (6)
H4	0.7935	0.1467	0.7784	0.070*
C18	1.1609 (4)	0.7810 (4)	0.9042 (3)	0.0778 (5)
H18A	1.1720	0.8322	0.8140	0.093*
H18B	1.1496	0.8506	0.9421	0.093*
C16	0.9352 (4)	0.7188 (4)	1.0492 (3)	0.0778 (5)
H16A	0.8790	0.6478	1.0685	0.093*
H16B	1.0165	0.6772	1.1144	0.093*
C17	0.8226 (6)	0.8584 (5)	1.0503 (5)	0.1329 (17)
H17A	0.8774	0.9296	1.0298	0.199*
H17B	0.7774	0.8405	1.1327	0.199*
H17C	0.7387	0.8971	0.9890	0.199*
C19	1.3069 (5)	0.6543 (5)	0.9545 (4)	0.1141 (14)
H19A	1.2959	0.6005	1.0433	0.171*
H19B	1.3960	0.6901	0.9411	0.171*
H19C	1.3248	0.5891	0.9120	0.171*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0341 (8)	0.0406 (8)	0.0607 (10)	−0.0087 (6)	0.0025 (7)	−0.0150 (7)
N1	0.0364 (9)	0.0393 (10)	0.0554 (11)	−0.0078 (8)	−0.0005 (8)	−0.0145 (9)
N2	0.0400 (10)	0.0525 (11)	0.0445 (11)	−0.0133 (9)	0.0030 (8)	−0.0168 (9)
C8	0.0367 (11)	0.0437 (11)	0.0381 (11)	−0.0115 (9)	0.0013 (9)	−0.0179 (9)
C7	0.0316 (10)	0.0437 (11)	0.0406 (11)	−0.0070 (8)	0.0014 (8)	−0.0202 (9)
O3	0.0406 (9)	0.0702 (11)	0.0623 (11)	−0.0191 (8)	0.0105 (8)	−0.0170 (9)
C9	0.0386 (11)	0.0401 (11)	0.0411 (11)	−0.0103 (9)	−0.0002 (9)	−0.0187 (9)
O2	0.0520 (10)	0.0530 (10)	0.0628 (11)	−0.0111 (8)	−0.0009 (8)	−0.0005 (9)
C6	0.0407 (11)	0.0436 (12)	0.0386 (11)	−0.0100 (9)	−0.0032 (9)	−0.0214 (9)
C10	0.0361 (10)	0.0386 (11)	0.0383 (11)	−0.0094 (8)	−0.0008 (8)	−0.0150 (9)
C15	0.0344 (11)	0.0470 (12)	0.0442 (12)	−0.0094 (9)	0.0013 (9)	−0.0199 (10)
C1	0.0418 (11)	0.0393 (11)	0.0451 (12)	−0.0090 (9)	−0.0023 (9)	−0.0186 (10)
C13	0.0539 (13)	0.0516 (13)	0.0449 (13)	−0.0201 (11)	−0.0051 (10)	−0.0184 (11)
C5	0.0455 (12)	0.0486 (13)	0.0494 (13)	−0.0057 (10)	−0.0061 (10)	−0.0241 (11)
C11	0.0381 (11)	0.0626 (14)	0.0517 (13)	−0.0198 (10)	0.0060 (10)	−0.0292 (11)
C14	0.0371 (11)	0.0543 (13)	0.0515 (13)	−0.0157 (10)	−0.0025 (10)	−0.0192 (11)
C12	0.0543 (14)	0.0726 (16)	0.0496 (14)	−0.0261 (12)	0.0123 (11)	−0.0359 (13)
C20	0.0363 (12)	0.0499 (13)	0.0732 (17)	−0.0054 (10)	0.0002 (11)	−0.0229 (12)
N3	0.0905 (12)	0.1014 (13)	0.0670 (10)	−0.0482 (10)	−0.0023 (9)	−0.0428 (10)
C2	0.0494 (13)	0.0516 (14)	0.0595 (15)	−0.0204 (11)	0.0012 (11)	−0.0216 (12)
C3	0.0729 (17)	0.0459 (14)	0.0617 (16)	−0.0251 (12)	−0.0033 (13)	−0.0158 (12)
C4	0.0681 (17)	0.0405 (13)	0.0597 (15)	−0.0073 (11)	−0.0104 (12)	−0.0191 (11)
C18	0.0905 (12)	0.1014 (13)	0.0670 (10)	−0.0482 (10)	−0.0023 (9)	−0.0428 (10)
C16	0.0905 (12)	0.1014 (13)	0.0670 (10)	−0.0482 (10)	−0.0023 (9)	−0.0428 (10)
C17	0.172 (5)	0.129 (4)	0.145 (4)	−0.071 (3)	0.028 (3)	−0.088 (3)
C19	0.094 (3)	0.151 (4)	0.098 (3)	−0.039 (3)	−0.022 (2)	−0.044 (3)

Geometric parameters (Å, º) top

O1—C9	1.349 (3)	C11—C12	1.373 (3)
O1—C1	1.402 (2)	C11—H11	0.9300
N1—C9	1.312 (3)	C14—H14	0.9300
N1—C20	1.453 (3)	C12—H12	0.9300
N1—H1	0.8600	C20—H20A	0.9600
N2—O3	1.249 (2)	C20—H20B	0.9600
N2—O2	1.262 (2)	C20—H20C	0.9600
N2—C8	1.377 (3)	N3—C16	1.465 (4)
C8—C9	1.388 (3)	N3—C18	1.487 (4)
C8—C7	1.507 (3)	C2—C3	1.376 (3)
C7—C6	1.510 (3)	C2—H2	0.9300
C7—C10	1.525 (3)	C3—C4	1.384 (4)
C7—H7	0.9800	C3—H3	0.9300
O3—N2	1.249 (2)	C4—H4	0.9300
O2—N2	1.262 (2)	C18—C19	1.460 (5)
C6—C1	1.377 (3)	C18—H18A	0.9700
C6—C5	1.390 (3)	C18—H18B	0.9700
C10—C15	1.380 (3)	C16—C17	1.455 (5)
C10—C11	1.385 (3)	C16—H16A	0.9700
C15—C14	1.380 (3)	C16—H16B	0.9700
C15—H15	0.9300	C17—H17A	0.9600
C1—C2	1.380 (3)	C17—H17B	0.9600
C13—N3	1.378 (3)	C17—H17C	0.9600
C13—C14	1.393 (3)	C19—H19A	0.9600
C13—C12	1.406 (3)	C19—H19B	0.9600
C5—C4	1.372 (4)	C19—H19C	0.9600
C5—H5	0.9300

C9—O1—C1	119.79 (16)	C11—C12—H12	119.4
C9—N1—C20	125.1 (2)	C13—C12—H12	119.4
C9—N1—H1	117.5	N1—C20—H20A	109.5
C20—N1—H1	117.5	N1—C20—H20B	109.5
O3—N2—O2	120.32 (18)	H20A—C20—H20B	109.5
O3—N2—O2	120.32 (18)	N1—C20—H20C	109.5
O3—N2—C8	118.58 (18)	H20A—C20—H20C	109.5
O2—N2—C8	121.10 (18)	H20B—C20—H20C	109.5
N2—C8—C9	120.35 (19)	C13—N3—C16	120.7 (2)
N2—C8—C7	117.15 (17)	C13—N3—C18	120.8 (2)
C9—C8—C7	122.25 (19)	C16—N3—C18	118.3 (2)
C6—C7—C8	109.37 (17)	C3—C2—C1	118.6 (2)
C6—C7—C10	110.83 (17)	C3—C2—H2	120.7
C8—C7—C10	111.95 (17)	C1—C2—H2	120.7
C6—C7—H7	108.2	C2—C3—C4	120.2 (2)
C10—C7—H7	108.2	C2—C3—H3	119.9
N1—C9—O1	112.50 (18)	C4—C3—H3	119.9
N1—C9—C8	127.1 (2)	C5—C4—C3	119.9 (2)
O1—C9—C8	120.41 (18)	C5—C4—H4	120.0
C1—C6—C5	117.4 (2)	C3—C4—H4	120.0
C1—C6—C7	120.57 (18)	C19—C18—N3	114.4 (3)
C5—C6—C7	121.92 (19)	C19—C18—H18A	108.7
C15—C10—C11	117.06 (19)	N3—C18—H18A	108.7
C15—C10—C7	122.49 (18)	C19—C18—H18B	108.7
C11—C10—C7	120.45 (18)	N3—C18—H18B	108.7
C14—C15—C10	122.0 (2)	H18A—C18—H18B	107.6
C14—C15—H15	119.0	C17—C16—N3	112.0 (3)
C10—C15—H15	119.0	C17—C16—H16A	109.2
C6—C1—C2	122.6 (2)	N3—C16—H16A	109.2
C6—C1—O1	121.69 (19)	C17—C16—H16B	109.2
C2—C1—O1	115.70 (19)	N3—C16—H16B	109.2
N3—C13—C14	122.1 (2)	H16A—C16—H16B	107.9
N3—C13—C12	121.4 (2)	C16—C17—H17A	109.5
C14—C13—C12	116.5 (2)	C16—C17—H17B	109.5
C4—C5—C6	121.2 (2)	H17A—C17—H17B	109.5
C4—C5—H5	119.4	C16—C17—H17C	109.5
C6—C5—H5	119.4	H17A—C17—H17C	109.5
C12—C11—C10	121.9 (2)	H17B—C17—H17C	109.5
C12—C11—H11	119.0	C18—C19—H19A	109.5
C10—C11—H11	119.0	C18—C19—H19B	109.5
C15—C14—C13	121.3 (2)	H19A—C19—H19B	109.5
C15—C14—H14	119.3	C18—C19—H19C	109.5
C13—C14—H14	119.3	H19A—C19—H19C	109.5
C11—C12—C13	121.2 (2)	H19B—C19—H19C	109.5

O3—N2—C8—N2	0 (17)	C8—C7—C6—C5	162.23 (19)
O2—N2—C8—N2	0 (100)	C10—C7—C6—C5	−73.9 (2)
O2—N2—C8—N2	0 (100)	C6—C7—C10—C15	124.8 (2)
N2—N2—C8—C9	0.00 (11)	C8—C7—C10—C15	−112.8 (2)
O3—N2—C8—C9	179.15 (19)	C6—C7—C10—C11	−55.4 (3)
O2—N2—C8—C9	−0.4 (3)	C8—C7—C10—C11	67.0 (3)
O2—N2—C8—C9	−0.4 (3)	C11—C10—C15—C14	−0.4 (3)
N2—N2—C8—C7	0.00 (19)	C7—C10—C15—C14	179.4 (2)
O3—N2—C8—C7	4.7 (3)	C5—C6—C1—C2	1.0 (3)
O2—N2—C8—C7	−174.88 (19)	C7—C6—C1—C2	−175.9 (2)
O2—N2—C8—C7	−174.88 (19)	C5—C6—C1—O1	179.92 (18)
N2—C8—C7—C6	−161.30 (17)	C7—C6—C1—O1	3.0 (3)
N2—C8—C7—C6	−161.30 (17)	C9—O1—C1—C6	15.4 (3)
C9—C8—C7—C6	24.4 (3)	C9—O1—C1—C2	−165.57 (19)
N2—C8—C7—C10	75.5 (2)	C1—C6—C5—C4	−1.0 (3)
N2—C8—C7—C10	75.5 (2)	C7—C6—C5—C4	175.8 (2)
C9—C8—C7—C10	−98.9 (2)	C15—C10—C11—C12	−0.3 (3)
O2—N2—O3—N2	0 (39)	C7—C10—C11—C12	179.9 (2)
O2—N2—O3—N2	0 (39)	C10—C15—C14—C13	1.0 (3)
C8—N2—O3—N2	0 (100)	N3—C13—C14—C15	−179.6 (2)
C20—N1—C9—O1	0.6 (3)	C12—C13—C14—C15	−0.8 (3)
C20—N1—C9—C8	−178.9 (2)	C10—C11—C12—C13	0.4 (4)
C1—O1—C9—N1	168.16 (18)	N3—C13—C12—C11	179.0 (2)
C1—O1—C9—C8	−12.3 (3)	C14—C13—C12—C11	0.1 (4)
N2—C8—C9—N1	−3.7 (3)	C14—C13—N3—C16	−158.1 (3)
N2—C8—C9—N1	−3.7 (3)	C12—C13—N3—C16	23.1 (4)
C7—C8—C9—N1	170.5 (2)	C14—C13—N3—C18	17.1 (4)
N2—C8—C9—O1	176.92 (18)	C12—C13—N3—C18	−161.7 (3)
N2—C8—C9—O1	176.92 (18)	C6—C1—C2—C3	0.0 (4)
C7—C8—C9—O1	−8.9 (3)	O1—C1—C2—C3	−179.0 (2)
N2—N2—O2—O2	0.0	C1—C2—C3—C4	−1.0 (4)
O3—N2—O2—O2	0.0 (2)	C6—C5—C4—C3	0.1 (4)
C8—N2—O2—O2	0.00 (11)	C2—C3—C4—C5	1.0 (4)
O3—N2—O2—N2	0 (10)	C13—N3—C18—C19	−92.4 (4)
O2—N2—O2—N2	0 (100)	C16—N3—C18—C19	82.9 (4)
C8—N2—O2—N2	0 (100)	C13—N3—C16—C17	−97.1 (4)
C8—C7—C6—C1	−21.0 (3)	C18—N3—C16—C17	87.6 (4)
C10—C7—C6—C1	102.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	1.96	2.596 (2)	129
C5—H5···O3ⁱ	0.93	2.52	3.325 (3)	144

Symmetry code: (i) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₃N₃O₃
M_r	353.41
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.9199 (11), 10.4333 (12), 11.6697 (8)
α, β, γ (°)	65.100 (9), 82.388 (8), 69.513 (11)
V (Å³)	922.63 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.45 × 0.35 × 0.35

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.923, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	17119, 3242, 2625
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.162, 1.05
No. of reflections	3242
No. of parameters	226
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.44

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), PLATON (Spek, 2009).