N,N-Dicyclo­hexyl-3,5-dinitro­benzamide

Saeed, S.; Rashid, N.; Butcher, R.J.; Öztürk Yildirim, S.; Hussain, R.

doi:10.1107/S1600536812038500

organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o2953

https://doi.org/10.1107/S1600536812038500

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N,N-Dicyclohexyl-3,5-dinitrobenzamide

Sohail Saeed,^a ^* Naghmana Rashid,^a Ray J. Butcher,^b Sema Öztürk Yildirim ^b,^c and Rizwan Hussain ^d

^aDepartment of Chemistry, Research Complex, Allama Iqbal Open University, Islamabad 44000, Pakistan, ^bDepartment of Chemistry, Howard University, 525 College Street NW, Washington DC 20059, USA, ^cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^dNational Engineering & Scientific Commission, PO Box 2801, Islamabad, Pakistan
^*Correspondence e-mail: sohail262001@yahoo.com

(Received 4 August 2012; accepted 7 September 2012; online 19 September 2012)

In the title compound, C₁₉H₂₅N₃O₅, the benzene ring is not coplanar with the amide group [dihedral angle = 61.90 (5)°]. The cyclohexyl rings are in chair conformations. There is a strong intermolecular interaction between the C=O group of the amide group and the nitro group of an adjoining molecule, with a short O⋯N distance of 2.7862 (17) Å. In the crystal, C—H⋯O interactions occur along the [100] direction.

Related literature

For background to the biological activity of N-substituted benzamides and their use in synthesis, see: Priya et al. (2005 ). For related structures and their use in molecular recognition, see: Toda et al. (1987 ); Saeed et al. (2011 , 2012 ). For puckering parameters, see Cremer & Pople (1975 ). For a description of the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

C₁₉H₂₅N₃O₅
M_r = 375.42
Triclinic, $[P \overline 1]$
a = 6.8187 (7) Å
b = 9.7877 (12) Å
c = 14.7423 (12) Å
α = 92.512 (8)°
β = 98.898 (8)°
γ = 99.704 (9)°
V = 955.67 (17) Å³
Z = 2
Cu Kα radiation
μ = 0.79 mm⁻¹
T = 123 K
0.51 × 0.17 × 0.04 mm

Data collection

Agilent Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan [CrysAlis RED (Agilent, 2011 ), based on expressions derived from Clark & Reid (1995 )] T_min = 0.690, T_max = 0.969
6078 measured reflections
3811 independent reflections
3144 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.132
S = 1.03
3811 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O4ⁱ	0.95	2.56	3.418 (2)	151
C16—H16B⋯O3ⁱⁱ	0.99	2.58	3.468 (2)	149
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+2, -y+2, -z+1.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812038500/nk2179sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812038500/nk2179Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812038500/nk2179Isup3.cml

checkCIF report

Comment top

The structure of the title compound, (I), was been determined to explore the effect of substituents on the structure of benzanilides (Saeed et al., 2011, 2012). A compound with the same basic skeleton as the title compound has been used in host–guest chemistry to form numerous highly crystalline adducts with a variety of common organic solvents (Toda et al., 1987).

The crystal structure and atom numbering of (I) is shown in Fig. 1. The nitro groups are almost coplanar with the attached benzene ring (dihedral angles between phenyl ring and nitro groups being 1.74 (27) and 6.43 (33)°, respectively). As in the related structure reported recently (Saeed, et al., 2012), the phenyl ring is not coplanar with the amide moiety (dihedral angle between planes C5—C7—N3—O5 and the phenyl ring of 61.90 (5) °). Also analogous with this structure the phenyl ring is twisted out of this plane as indicated by the C4 C5 C7 O5 torsion angle of 112.76 (16) ° (in the previous structure containing two molecules in the symmetric unit these angles were 121.46 (33)° and -119.62 (34)°). The cyclohexyl rings are both in a chair conformation [the puckering parameters (Cremer & Pople, 1975) are Q(2) and φ(2) 0.018 (1) Å and 4.184 (1) ° in C8—C13, 0.025 (1) Å and 305.147 (1) ° in C14—C19). There is a strong intermolecular interaction between the C=O group of the amide moiety and the nitro group of an adjoining molecule (O5···N2 distance of 2.7862 (17) Å) so that these molecules form a dimeric unit. A search of the Cambridge Structural Database (Allen, 2002) for similar intermolecular interactions between carbonyl groups and nitro groups showed that such interactions are not universal. There were over 7000 hits for structures containing both these groups but only 515 contained such interactions with a mean distance of 2.963 Å) and a minimum of 2.73 Å. Thus this interaction in this compound is one of the strongest to be observed. While there are no classic hydrogen bonds found in the crystal, there are weak C—H···O intra- and intermolecular interactions.

Related literature top

For background to the biological activity of N-substituted benzamides and their use in synthesis, see: Priya et al. (2005). For related structures and their use in molecular recognition, see: Toda et al. (1987); Saeed et al. (2011, 2012). For puckering parameters, see Cremer & Pople (1975). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

To a 250 ml round flask fitted with a condenser was added dicyclohexyl amine (0.01 mol), dichloromethane (15 ml) and triethylamine(0.5 ml) with magnetic stirring. 3,5-dinitrobenzoyl chloride (0.01 mol) was added gradually. The reaction mixture was stirred at room temperature for 1 h and then refluxed for 2 h. The product precipitated as a colorless powder, which was washed three times with water and dichloromethane. Recrystallization from ethyl acetate produced the crystals of the title compound.

Structure description top

For background to the biological activity of N-substituted benzamides and their use in synthesis, see: Priya et al. (2005). For related structures and their use in molecular recognition, see: Toda et al. (1987); Saeed et al. (2011, 2012). For puckering parameters, see Cremer & Pople (1975). For a description of the Cambridge Structural Database, see: Allen (2002).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound with 30% probability displacement ellipsoids. The diagram also shows the association of the molecules into dimeric units through C=O···nitro interamolecular interactions [symmetry code: (A) = 1 - x, 1 - y, 1 - z].

N,N-Dicyclohexyl-3,5-dinitrobenzamide top

Crystal data top

C₁₉H₂₅N₃O₅	Z = 2
M_r = 375.42	F(000) = 400
Triclinic, P1	D_x = 1.305 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 6.8187 (7) Å	Cell parameters from 2277 reflections
b = 9.7877 (12) Å	θ = 3.0–75.2°
c = 14.7423 (12) Å	µ = 0.79 mm⁻¹
α = 92.512 (8)°	T = 123 K
β = 98.898 (8)°	`needle-plate`, colorless
γ = 99.704 (9)°	0.51 × 0.17 × 0.04 mm
V = 955.67 (17) Å³

Data collection top

Agilent Xcalibur Ruby Gemini diffractometer	3811 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3144 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
Detector resolution: 10.5081 pixels mm^-1	θ_max = 75.4°, θ_min = 3.0°
ω scans	h = −8→7
Absorption correction: multi-scan [CrysAlis RED (Agilent, 2011), based on expressions derived from Clark & Reid (1995)]	k = −10→12
T_min = 0.690, T_max = 0.969	l = −18→15
6078 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0695P)² + 0.0476P] where P = (F_o² + 2F_c²)/3
3811 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₉H₂₅N₃O₅	γ = 99.704 (9)°
M_r = 375.42	V = 955.67 (17) Å³
Triclinic, P1	Z = 2
a = 6.8187 (7) Å	Cu Kα radiation
b = 9.7877 (12) Å	µ = 0.79 mm⁻¹
c = 14.7423 (12) Å	T = 123 K
α = 92.512 (8)°	0.51 × 0.17 × 0.04 mm
β = 98.898 (8)°

Data collection top

Agilent Xcalibur Ruby Gemini diffractometer	3811 independent reflections
Absorption correction: multi-scan [CrysAlis RED (Agilent, 2011), based on expressions derived from Clark & Reid (1995)]	3144 reflections with I > 2σ(I)
T_min = 0.690, T_max = 0.969	R_int = 0.032
6078 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.03	Δρ_max = 0.30 e Å⁻³
3811 reflections	Δρ_min = −0.23 e Å⁻³
244 parameters

Special details top

Experimental. Absorption correction: CrysAlis RED, (Agilent, 2011) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. (Clark & Reid, 1995).

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	0.23442 (17)	0.94242 (13)	0.55223 (8)	0.0308 (3)
O2	0.4677 (2)	0.98065 (14)	0.67312 (8)	0.0362 (3)
O3	1.03595 (18)	0.75165 (13)	0.69435 (7)	0.0325 (3)
O4	1.08761 (16)	0.63134 (13)	0.57626 (8)	0.0303 (3)
O5	0.29440 (16)	0.51429 (12)	0.34083 (7)	0.0274 (3)
N1	0.3957 (2)	0.92478 (14)	0.59620 (9)	0.0259 (3)
N2	0.98833 (19)	0.70201 (14)	0.61477 (8)	0.0252 (3)
N3	0.54384 (18)	0.61099 (13)	0.26430 (8)	0.0220 (3)
C1	0.5115 (2)	0.83290 (15)	0.55400 (10)	0.0234 (3)
C2	0.6958 (2)	0.81731 (16)	0.60284 (9)	0.0234 (3)
H2A	0.7478	0.8646	0.6615	0.028*
C3	0.7997 (2)	0.72959 (16)	0.56194 (10)	0.0226 (3)
C4	0.7312 (2)	0.66292 (16)	0.47469 (9)	0.0228 (3)
H4A	0.8090	0.6051	0.4479	0.027*
C5	0.5460 (2)	0.68296 (16)	0.42755 (9)	0.0227 (3)
C6	0.4320 (2)	0.76562 (16)	0.46813 (10)	0.0233 (3)
H6A	0.3025	0.7759	0.4377	0.028*
C7	0.4509 (2)	0.59667 (16)	0.33856 (9)	0.0222 (3)
C8	0.4805 (2)	0.50539 (16)	0.18488 (9)	0.0230 (3)
H8A	0.5724	0.5316	0.1394	0.028*
C9	0.5117 (2)	0.36144 (17)	0.21379 (10)	0.0291 (3)
H9A	0.4270	0.3328	0.2609	0.035*
H9B	0.6545	0.3654	0.2415	0.035*
C10	0.4561 (3)	0.25421 (18)	0.13107 (11)	0.0329 (4)
H10A	0.5498	0.2776	0.0868	0.040*
H10B	0.4701	0.1610	0.1519	0.040*
C11	0.2403 (3)	0.25131 (18)	0.08358 (11)	0.0338 (4)
H11A	0.2087	0.1835	0.0293	0.041*
H11B	0.1458	0.2211	0.1264	0.041*
C12	0.2126 (3)	0.39444 (18)	0.05318 (10)	0.0325 (4)
H12A	0.0709	0.3907	0.0237	0.039*
H12B	0.3004	0.4216	0.0070	0.039*
C13	0.2648 (2)	0.50401 (17)	0.13510 (10)	0.0270 (3)
H13A	0.2535	0.5969	0.1130	0.032*
H13B	0.1683	0.4825	0.1784	0.032*
C14	0.7089 (2)	0.72822 (15)	0.25786 (9)	0.0216 (3)
H14A	0.7252	0.7921	0.3144	0.026*
C15	0.6558 (2)	0.81222 (16)	0.17448 (9)	0.0236 (3)
H15A	0.6357	0.7516	0.1171	0.028*
H15B	0.5283	0.8461	0.1784	0.028*
C16	0.8253 (2)	0.93638 (17)	0.17186 (10)	0.0275 (3)
H16A	0.7932	0.9849	0.1154	0.033*
H16B	0.8334	1.0027	0.2255	0.033*
C17	1.0291 (2)	0.89085 (18)	0.17335 (11)	0.0294 (3)
H17A	1.1359	0.9739	0.1764	0.035*
H17B	1.0269	0.8340	0.1159	0.035*
C18	1.0770 (2)	0.80630 (17)	0.25612 (10)	0.0276 (3)
H18A	1.0916	0.8660	0.3136	0.033*
H18C	1.2067	0.7745	0.2542	0.033*
C19	0.9104 (2)	0.68002 (16)	0.25653 (10)	0.0251 (3)
H19C	0.9008	0.6170	0.2010	0.030*
H19A	0.9432	0.6283	0.3114	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0303 (6)	0.0312 (6)	0.0329 (6)	0.0102 (5)	0.0063 (4)	0.0034 (5)
O2	0.0422 (7)	0.0403 (7)	0.0264 (5)	0.0109 (5)	0.0059 (5)	−0.0091 (5)
O3	0.0332 (6)	0.0371 (6)	0.0230 (5)	0.0058 (5)	−0.0054 (4)	−0.0046 (5)
O4	0.0261 (5)	0.0339 (6)	0.0309 (5)	0.0080 (5)	0.0028 (4)	−0.0002 (5)
O5	0.0273 (5)	0.0304 (6)	0.0222 (5)	−0.0011 (4)	0.0046 (4)	0.0000 (4)
N1	0.0297 (6)	0.0251 (6)	0.0239 (6)	0.0046 (5)	0.0075 (5)	0.0031 (5)
N2	0.0251 (6)	0.0250 (6)	0.0236 (6)	0.0010 (5)	0.0018 (5)	0.0018 (5)
N3	0.0231 (6)	0.0238 (6)	0.0178 (5)	0.0020 (5)	0.0022 (4)	−0.0009 (4)
C1	0.0281 (7)	0.0222 (7)	0.0208 (6)	0.0032 (6)	0.0077 (5)	0.0030 (5)
C2	0.0281 (7)	0.0239 (7)	0.0171 (6)	0.0007 (5)	0.0048 (5)	0.0006 (5)
C3	0.0223 (6)	0.0241 (7)	0.0204 (6)	0.0009 (5)	0.0031 (5)	0.0031 (5)
C4	0.0248 (7)	0.0243 (7)	0.0195 (6)	0.0030 (5)	0.0065 (5)	0.0006 (5)
C5	0.0266 (7)	0.0248 (7)	0.0158 (6)	0.0009 (5)	0.0045 (5)	0.0024 (5)
C6	0.0241 (6)	0.0264 (7)	0.0192 (6)	0.0030 (5)	0.0033 (5)	0.0051 (5)
C7	0.0242 (6)	0.0230 (7)	0.0194 (6)	0.0055 (5)	0.0020 (5)	0.0017 (5)
C8	0.0272 (7)	0.0239 (7)	0.0167 (6)	0.0021 (5)	0.0035 (5)	−0.0013 (5)
C9	0.0344 (8)	0.0282 (8)	0.0234 (7)	0.0087 (6)	−0.0021 (6)	−0.0001 (6)
C10	0.0441 (9)	0.0260 (8)	0.0292 (8)	0.0103 (7)	0.0044 (7)	−0.0024 (6)
C11	0.0447 (9)	0.0268 (8)	0.0249 (7)	0.0002 (7)	−0.0009 (7)	−0.0044 (6)
C12	0.0403 (9)	0.0312 (8)	0.0213 (7)	0.0040 (7)	−0.0050 (6)	−0.0033 (6)
C13	0.0308 (7)	0.0273 (8)	0.0213 (7)	0.0073 (6)	−0.0017 (6)	−0.0021 (6)
C14	0.0242 (6)	0.0230 (7)	0.0169 (6)	0.0026 (5)	0.0032 (5)	0.0006 (5)
C15	0.0267 (7)	0.0250 (7)	0.0191 (6)	0.0053 (5)	0.0027 (5)	0.0021 (5)
C16	0.0323 (7)	0.0251 (7)	0.0245 (7)	0.0027 (6)	0.0045 (6)	0.0043 (6)
C17	0.0288 (7)	0.0309 (8)	0.0271 (7)	−0.0007 (6)	0.0065 (6)	0.0038 (6)
C18	0.0228 (7)	0.0316 (8)	0.0270 (7)	0.0023 (6)	0.0025 (5)	0.0032 (6)
C19	0.0235 (7)	0.0275 (7)	0.0244 (7)	0.0045 (6)	0.0042 (5)	0.0034 (5)

Geometric parameters (Å, º) top

O1—N1	1.2300 (18)	C10—H10A	0.9900
O2—N1	1.2284 (18)	C10—H10B	0.9900
O3—N2	1.2235 (17)	C11—C12	1.522 (2)
O4—N2	1.2253 (18)	C11—H11A	0.9900
O5—C7	1.2299 (19)	C11—H11B	0.9900
N1—C1	1.470 (2)	C12—C13	1.536 (2)
N2—C3	1.4696 (19)	C12—H12A	0.9900
N3—C7	1.3486 (19)	C12—H12B	0.9900
N3—C14	1.4831 (18)	C13—H13A	0.9900
N3—C8	1.4874 (17)	C13—H13B	0.9900
C1—C2	1.384 (2)	C14—C19	1.528 (2)
C1—C6	1.387 (2)	C14—C15	1.5392 (19)
C2—C3	1.376 (2)	C14—H14A	1.0000
C2—H2A	0.9500	C15—C16	1.536 (2)
C3—C4	1.391 (2)	C15—H15A	0.9900
C4—C5	1.393 (2)	C15—H15B	0.9900
C4—H4A	0.9500	C16—C17	1.526 (2)
C5—C6	1.389 (2)	C16—H16A	0.9900
C5—C7	1.5199 (19)	C16—H16B	0.9900
C6—H6A	0.9500	C17—C18	1.529 (2)
C8—C9	1.529 (2)	C17—H17A	0.9900
C8—C13	1.536 (2)	C17—H17B	0.9900
C8—H8A	1.0000	C18—C19	1.532 (2)
C9—C10	1.531 (2)	C18—H18A	0.9900
C9—H9A	0.9900	C18—H18C	0.9900
C9—H9B	0.9900	C19—H19C	0.9900
C10—C11	1.523 (2)	C19—H19A	0.9900

O2—N1—O1	123.96 (14)	C12—C11—H11B	109.5
O2—N1—C1	117.72 (13)	C10—C11—H11B	109.5
O1—N1—C1	118.31 (13)	H11A—C11—H11B	108.1
O3—N2—O4	124.38 (13)	C11—C12—C13	111.33 (13)
O3—N2—C3	117.65 (13)	C11—C12—H12A	109.4
O4—N2—C3	117.97 (12)	C13—C12—H12A	109.4
C7—N3—C14	122.84 (12)	C11—C12—H12B	109.4
C7—N3—C8	119.34 (12)	C13—C12—H12B	109.4
C14—N3—C8	117.82 (11)	H12A—C12—H12B	108.0
C2—C1—C6	123.08 (15)	C8—C13—C12	110.00 (13)
C2—C1—N1	117.81 (13)	C8—C13—H13A	109.7
C6—C1—N1	119.12 (14)	C12—C13—H13A	109.7
C3—C2—C1	116.45 (13)	C8—C13—H13B	109.7
C3—C2—H2A	121.8	C12—C13—H13B	109.7
C1—C2—H2A	121.8	H13A—C13—H13B	108.2
C2—C3—C4	123.15 (14)	N3—C14—C19	112.10 (12)
C2—C3—N2	117.98 (13)	N3—C14—C15	111.61 (11)
C4—C3—N2	118.84 (14)	C19—C14—C15	111.05 (12)
C3—C4—C5	118.39 (14)	N3—C14—H14A	107.3
C3—C4—H4A	120.8	C19—C14—H14A	107.3
C5—C4—H4A	120.8	C15—C14—H14A	107.3
C6—C5—C4	120.26 (13)	C16—C15—C14	110.47 (12)
C6—C5—C7	118.74 (13)	C16—C15—H15A	109.6
C4—C5—C7	120.25 (14)	C14—C15—H15A	109.6
C1—C6—C5	118.57 (14)	C16—C15—H15B	109.6
C1—C6—H6A	120.7	C14—C15—H15B	109.6
C5—C6—H6A	120.7	H15A—C15—H15B	108.1
O5—C7—N3	124.41 (13)	C17—C16—C15	111.74 (13)
O5—C7—C5	116.40 (12)	C17—C16—H16A	109.3
N3—C7—C5	119.15 (12)	C15—C16—H16A	109.3
N3—C8—C9	110.96 (11)	C17—C16—H16B	109.3
N3—C8—C13	113.26 (12)	C15—C16—H16B	109.3
C9—C8—C13	111.99 (13)	H16A—C16—H16B	107.9
N3—C8—H8A	106.7	C16—C17—C18	110.80 (13)
C9—C8—H8A	106.7	C16—C17—H17A	109.5
C13—C8—H8A	106.7	C18—C17—H17A	109.5
C8—C9—C10	110.91 (12)	C16—C17—H17B	109.5
C8—C9—H9A	109.5	C18—C17—H17B	109.5
C10—C9—H9A	109.5	H17A—C17—H17B	108.1
C8—C9—H9B	109.5	C17—C18—C19	111.27 (12)
C10—C9—H9B	109.5	C17—C18—H18A	109.4
H9A—C9—H9B	108.0	C19—C18—H18A	109.4
C11—C10—C9	110.78 (14)	C17—C18—H18C	109.4
C11—C10—H10A	109.5	C19—C18—H18C	109.4
C9—C10—H10A	109.5	H18A—C18—H18C	108.0
C11—C10—H10B	109.5	C14—C19—C18	109.64 (13)
C9—C10—H10B	109.5	C14—C19—H19C	109.7
H10A—C10—H10B	108.1	C18—C19—H19C	109.7
C12—C11—C10	110.67 (14)	C14—C19—H19A	109.7
C12—C11—H11A	109.5	C18—C19—H19A	109.7
C10—C11—H11A	109.5	H19C—C19—H19A	108.2

O2—N1—C1—C2	−1.2 (2)	C6—C5—C7—N3	124.80 (15)
O1—N1—C1—C2	177.97 (13)	C4—C5—C7—N3	−65.11 (19)
O2—N1—C1—C6	178.46 (14)	C7—N3—C8—C9	−60.72 (17)
O1—N1—C1—C6	−2.4 (2)	C14—N3—C8—C9	119.11 (14)
C6—C1—C2—C3	−0.3 (2)	C7—N3—C8—C13	66.24 (17)
N1—C1—C2—C3	179.38 (12)	C14—N3—C8—C13	−113.94 (14)
C1—C2—C3—C4	2.5 (2)	N3—C8—C9—C10	−177.25 (12)
C1—C2—C3—N2	−175.35 (13)	C13—C8—C9—C10	55.10 (17)
O3—N2—C3—C2	4.5 (2)	C8—C9—C10—C11	−56.00 (18)
O4—N2—C3—C2	−175.30 (13)	C9—C10—C11—C12	57.49 (18)
O3—N2—C3—C4	−173.47 (13)	C10—C11—C12—C13	−57.87 (19)
O4—N2—C3—C4	6.7 (2)	N3—C8—C13—C12	178.94 (12)
C2—C3—C4—C5	−1.8 (2)	C9—C8—C13—C12	−54.65 (17)
N2—C3—C4—C5	176.03 (13)	C11—C12—C13—C8	55.91 (18)
C3—C4—C5—C6	−1.2 (2)	C7—N3—C14—C19	113.34 (15)
C3—C4—C5—C7	−171.14 (13)	C8—N3—C14—C19	−66.48 (16)
C2—C1—C6—C5	−2.6 (2)	C7—N3—C14—C15	−121.37 (14)
N1—C1—C6—C5	177.76 (13)	C8—N3—C14—C15	58.81 (16)
C4—C5—C6—C1	3.3 (2)	N3—C14—C15—C16	177.61 (12)
C7—C5—C6—C1	173.39 (13)	C19—C14—C15—C16	−56.51 (16)
C14—N3—C7—O5	168.10 (14)	C14—C15—C16—C17	54.76 (16)
C8—N3—C7—O5	−12.1 (2)	C15—C16—C17—C18	−54.88 (17)
C14—N3—C7—C5	−14.2 (2)	C16—C17—C18—C19	56.63 (18)
C8—N3—C7—C5	165.61 (13)	N3—C14—C19—C18	−176.37 (11)
C6—C5—C7—O5	−57.32 (19)	C15—C14—C19—C18	58.03 (15)
C4—C5—C7—O5	112.77 (16)	C17—C18—C19—C14	−58.10 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O5	0.99	2.46	3.050 (2)	118
C13—H13B···O5	0.99	2.40	3.0043 (18)	119
C4—H4A···O4ⁱ	0.95	2.56	3.418 (2)	151
C16—H16B···O3ⁱⁱ	0.99	2.58	3.468 (2)	149

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+2, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₅N₃O₅
M_r	375.42
Crystal system, space group	Triclinic, P1
Temperature (K)	123
a, b, c (Å)	6.8187 (7), 9.7877 (12), 14.7423 (12)
α, β, γ (°)	92.512 (8), 98.898 (8), 99.704 (9)
V (Å³)	955.67 (17)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.79
Crystal size (mm)	0.51 × 0.17 × 0.04

Data collection
Diffractometer	Agilent Xcalibur Ruby Gemini
Absorption correction	Multi-scan [CrysAlis RED (Agilent, 2011), based on expressions derived from Clark & Reid (1995)]
T_min, T_max	0.690, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	6078, 3811, 3144
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.132, 1.03
No. of reflections	3811
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.23

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O4ⁱ	0.95	2.56	3.418 (2)	150.8
C16—H16B···O3ⁱⁱ	0.99	2.58	3.468 (2)	148.8

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+2, −y+2, −z+1.

Acknowledgements

RJB acknowledges the NSF MRI program (grant No. CHE– 0619278) for funds to purchase an X-ray diffractometer.

References

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