(3S,4S)-1-Benzyl-4-(N-octylcarbamoyl­oxy)pyrrolidin-3-yl N-octylcarbamate: a low-temperature redetermination

Cicchi, S.; Faggi, C.; Ghini, G.; Guerri, A.; Parlanti, J.

doi:10.1107/S160053680702572X

Buy article online - an online subscription or single-article purchase is required to access this article.

(3S,4S)-1-Benzyl-4-(N-octylcarbamoyloxy)pyrrolidin-3-yl N-octylcarbamate: a low-temperature redetermination

S. Cicchi, C. Faggi, G. Ghini, A. Guerri and J. Parlanti

The title compound, C₂₉H₄₉N₃O₄, is a model compound synthesized to obtain information on the intermomecular forces that drive the self-assembly of a similar compound bearing longer aliphatic chains. In the crystal, molecules are arranged in columns due to the formation of two antiparallel strong hydrogen-bonded chains by the carbamate units. The two long aliphatic chains are trans.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680702572X/bg2057sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680702572X/bg2057Isup2.hkl Contains datablock I

CCDC reference: 654865

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.003 Å
R factor = 0.039
wR factor = 0.096
Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)        100 Ang.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          4
PLAT322_ALERT_2_C Check Hybridisation of  H23A   in Main Residue .          ?
PLAT322_ALERT_2_C Check Hybridisation of  H23B   in Main Residue .          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           74.22
           From the CIF: _reflns_number_total               5438
           Count of symmetry unique reflns         3094
           Completeness (_total/calc)            175.76%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2344
           Fraction of Friedel pairs measured     0.758
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2     = .          S
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

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

Comment top

The title compound, (I), was synthesized as a model compound. Its 150 K data collection was useful to suggest a model for the formation of organogels by its homologue, (3S, 4S)-Dodecyl-carbamic acid 1-benzyl-4-dodecylcarbamoyl oxy-pyrrolidin-3-yl ester, bearing longer aliphatic chains (C12) (Cicchi et al., 2007). To develop such a model for the formation of the gel it was necessary to obtain information about the more stable conformation of the carbamate units responsable for the self assembling process that give origin to an organogel. Information derived from X-Ray crystallography had already been used to propose suitable models for gel formation (viz., Schoonbeek et al., 2000). In the presents case, while C12 did not afford suitable crystals, compound (I) crystallized from diisopropyl ether. The structure showed that the crystal is formed by long columns in which the two carbamates units of each molecule participate in the formation of two antiparallel strong H-bonded chains (Table 2). The long all-trans aliphatic chains contributes to the packing of the crystal by Van der Walls interactions. Dimensions are available in the archived CIF.

Related literature top

For related literature, see: Cicchi et al. (2007); Schoonbeek et al. (2000).

Experimental top

An anhydrous toluene solution (10 ml) of (3R,4S)-1-benzylpyrrolidine-3,4-diol (200 mg, 1.04 mmol, 1eq) and octylisocianate (321 mg, 2.1eq) were refluxed for 72 h. The crude reaction mixture was concentrated and purified by flash column chromatography (Rf = 1/2, CH2Cl2/AcOEt 1:1) to obtain 323 mg of a white solid (64% yield). The compound was crystallized from diisopropylether to obtain white crystals. M.p. 94–95°C. Crystals suitable for X-ray analysis were obtained by slow evaporation of a diluted diisopropyl ether solution.

Structure description top

For related literature, see: Cicchi et al. (2007); Schoonbeek et al. (2000).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. Molecular structure of (I). Displacement ellipsoids are drawn at the 40% probability level.
	Fig. 2. Packing view of (I) showing the connectivity of molecules via N—H···O links (dashed lines). Only nitrogen and oxygen atoms involved in intermolecular hydrogen bonding have been labelled. [Symmetry codes as in Table 2].

(3S,4S)-1-Benzyl-4-(N-octylcarbamoyloxy)pyrrolidin-3-yl N-octylcarbamate top

Crystal data top

C₂₉H₄₉N₃O₄	F(000) = 552
M_r = 503.71	D_x = 1.145 Mg m⁻³
Monoclinic, P2₁	Melting point: 94 K
Hall symbol: P 2yb	Cu Kα radiation, λ = 1.54184 Å
a = 5.039 (1) Å	Cell parameters from 10467 reflections
b = 15.825 (1) Å	θ = 3.7–74.2°
c = 18.330 (1) Å	µ = 0.60 mm⁻¹
β = 90.884 (1)°	T = 150 K
V = 1461.5 (3) Å³	Prismatic, colourless
Z = 2	0.32 × 0.22 × 0.18 mm

Data collection top

Oxford Diffraction XCALIBUR PX Ultra CCD diffractometer	5438 independent reflections
Radiation source: Enhance (Cu) X-ray Source	4359 reflections with I > 2σ(I)
Oxford Diffraction Enhance ULTRA assembly monochromator	R_int = 0.053
Detector resolution: 8.1241 pixels mm^-1	θ_max = 74.2°, θ_min = 3.7°
ω scans	h = −5→6
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −19→19
T_min = 0.851, T_max = 0.898	l = −22→22
23018 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0542P)²] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
5438 reflections	Δρ_max = 0.30 e Å⁻³
327 parameters	Δρ_min = −0.22 e Å⁻³
1 restraint	Absolute structure: Flack (1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.02 (16)

Crystal data top

C₂₉H₄₉N₃O₄	V = 1461.5 (3) Å³
M_r = 503.71	Z = 2
Monoclinic, P2₁	Cu Kα radiation
a = 5.039 (1) Å	µ = 0.60 mm⁻¹
b = 15.825 (1) Å	T = 150 K
c = 18.330 (1) Å	0.32 × 0.22 × 0.18 mm
β = 90.884 (1)°

Data collection top

Oxford Diffraction XCALIBUR PX Ultra CCD diffractometer	5438 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	4359 reflections with I > 2σ(I)
T_min = 0.851, T_max = 0.898	R_int = 0.053
23018 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.096	Δρ_max = 0.30 e Å⁻³
S = 1.08	Δρ_min = −0.22 e Å⁻³
5438 reflections	Absolute structure: Flack (1983), with how many Friedel pairs?
327 parameters	Absolute structure parameter: −0.02 (16)
1 restraint

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
N1	0.4101 (3)	0.30272 (10)	0.04853 (9)	0.0330 (3)
N2	0.9553 (3)	0.00132 (10)	0.10478 (8)	0.0337 (4)
HN2	1.1142	0.0216	0.0960	0.040*
N3	0.4456 (3)	0.20838 (11)	−0.21319 (7)	0.0314 (3)
HN3	0.2770	0.2064	−0.2015	0.038*
O1	0.8120 (2)	0.11802 (8)	0.05040 (7)	0.0319 (3)
O2	0.5140 (2)	0.02369 (9)	0.09573 (8)	0.0401 (3)
O3	0.5166 (2)	0.21265 (9)	−0.09450 (6)	0.0341 (3)
O4	0.8671 (2)	0.22108 (10)	−0.17371 (7)	0.0367 (3)
C1	0.6848 (3)	0.22989 (12)	−0.03276 (9)	0.0291 (4)
H1	0.8768	0.2221	−0.0440	0.035*
C2	0.5931 (3)	0.17090 (12)	0.02901 (9)	0.0296 (4)
H2	0.4416	0.1352	0.0113	0.035*
C3	0.4998 (4)	0.22994 (13)	0.08996 (10)	0.0362 (4)
H3A	0.3533	0.2044	0.1178	0.043*
H3B	0.6472	0.2448	0.1239	0.043*
C4	0.6266 (3)	0.31805 (12)	−0.00332 (9)	0.0320 (4)
H4B	0.7846	0.3423	0.0218	0.038*
H4A	0.5687	0.3567	−0.0430	0.038*
C5	0.3196 (4)	0.37631 (14)	0.09092 (11)	0.0389 (4)
H5A	0.1821	0.3571	0.1252	0.047*
H5B	0.2348	0.4171	0.0569	0.047*
C6	0.5319 (4)	0.42160 (13)	0.13372 (11)	0.0374 (4)
C7	0.6694 (4)	0.48838 (14)	0.10240 (12)	0.0436 (5)
H7	0.6238	0.5058	0.0542	0.052*
C8	0.8694 (5)	0.52962 (15)	0.13954 (14)	0.0521 (6)
H8	0.9604	0.5754	0.1176	0.063*
C9	0.9355 (4)	0.50376 (17)	0.20860 (14)	0.0537 (6)
H9	1.0751	0.5314	0.2346	0.064*
C10	0.8012 (4)	0.43777 (18)	0.24092 (13)	0.0544 (6)
H10	0.8495	0.4203	0.2889	0.065*
C11	0.5966 (4)	0.39690 (15)	0.20387 (11)	0.0464 (5)
H11	0.5021	0.3524	0.2266	0.056*
C12	0.7430 (3)	0.04508 (12)	0.08529 (9)	0.0290 (4)
C13	0.9289 (4)	−0.08052 (13)	0.14085 (10)	0.0349 (4)
H13A	1.0839	−0.1159	0.1285	0.042*
H13B	0.7683	−0.1091	0.1212	0.042*
C14	0.9094 (4)	−0.07582 (13)	0.22323 (11)	0.0362 (4)
H14A	0.7787	−0.0318	0.2360	0.043*
H14B	0.8428	−0.1305	0.2417	0.043*
C15	1.1704 (4)	−0.05602 (14)	0.26068 (10)	0.0371 (4)
H15A	1.2328	0.0002	0.2446	0.045*
H15B	1.3043	−0.0984	0.2462	0.045*
C16	1.1456 (4)	−0.05638 (15)	0.34315 (11)	0.0406 (5)
H16A	1.0220	−0.0109	0.3574	0.049*
H16B	1.0672	−0.1109	0.3583	0.049*
C17	1.4051 (4)	−0.04410 (16)	0.38341 (11)	0.0424 (5)
H17A	1.4807	0.0113	0.3697	0.051*
H17B	1.5311	−0.0885	0.3681	0.051*
C18	1.3776 (4)	−0.04762 (15)	0.46605 (11)	0.0434 (5)
H18A	1.2542	−0.0026	0.4815	0.052*
H18B	1.2991	−0.1026	0.4797	0.052*
C19	1.6352 (4)	−0.03697 (18)	0.50561 (11)	0.0516 (6)
H19A	1.7121	0.0184	0.4925	0.062*
H19B	1.7593	−0.0814	0.4894	0.062*
C20	1.6105 (6)	−0.0417 (2)	0.58814 (12)	0.0639 (7)
H20A	1.5390	−0.0970	0.6017	0.077*
H20B	1.4909	0.0029	0.6048	0.077*
H20C	1.7859	−0.0341	0.6111	0.077*
C21	0.6301 (3)	0.21444 (12)	−0.16218 (9)	0.0273 (4)
C22	0.5237 (3)	0.20502 (15)	−0.28971 (9)	0.0374 (4)
H22B	0.6365	0.1547	−0.2976	0.045*
H22A	0.6292	0.2559	−0.3015	0.045*
C23	0.2871 (3)	0.20081 (14)	−0.33888 (9)	0.0344 (4)
H23A	0.1093	0.1962	−0.3229	0.041*
H23B	0.1878	0.1486	−0.3287	0.041*
C24	0.3689 (4)	0.20496 (14)	−0.41899 (9)	0.0373 (4)
H24A	0.4649	0.2586	−0.4272	0.045*
H24B	0.4933	0.1580	−0.4288	0.045*
C25	0.1414 (4)	0.19961 (14)	−0.47192 (9)	0.0385 (5)
H25A	0.0182	0.2472	−0.4632	0.046*
H25B	0.0434	0.1463	−0.4637	0.046*
C26	0.2326 (4)	0.20255 (15)	−0.55127 (10)	0.0404 (5)
H26B	0.3258	0.2567	−0.5595	0.049*
H26A	0.3615	0.1563	−0.5591	0.049*
C27	0.0124 (4)	0.19438 (15)	−0.60607 (10)	0.0424 (5)
H27A	−0.1113	0.2424	−0.6003	0.051*
H27B	−0.0872	0.1418	−0.5963	0.051*
C28	0.1096 (4)	0.19258 (17)	−0.68477 (11)	0.0487 (6)
H28A	0.1948	0.2473	−0.6960	0.058*
H28B	0.2457	0.1479	−0.6893	0.058*
C29	−0.1075 (5)	0.17669 (19)	−0.73927 (12)	0.0578 (6)
H29C	−0.2419	0.2212	−0.7356	0.069*
H29B	−0.1890	0.1217	−0.7296	0.069*
H29A	−0.0342	0.1768	−0.7885	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0300 (8)	0.0340 (9)	0.0349 (8)	0.0031 (6)	−0.0037 (6)	−0.0025 (7)
N2	0.0230 (7)	0.0401 (9)	0.0379 (8)	−0.0018 (6)	−0.0030 (6)	0.0054 (7)
N3	0.0233 (7)	0.0444 (9)	0.0263 (7)	−0.0013 (7)	−0.0036 (5)	−0.0014 (7)
O1	0.0224 (5)	0.0334 (7)	0.0397 (7)	−0.0003 (5)	−0.0040 (5)	0.0058 (6)
O2	0.0221 (6)	0.0453 (8)	0.0528 (8)	−0.0030 (5)	−0.0049 (6)	0.0140 (7)
O3	0.0249 (6)	0.0529 (8)	0.0242 (6)	−0.0067 (6)	−0.0049 (5)	−0.0028 (6)
O4	0.0250 (6)	0.0522 (8)	0.0329 (6)	0.0017 (6)	−0.0039 (5)	−0.0010 (6)
C1	0.0228 (8)	0.0371 (10)	0.0271 (8)	−0.0016 (7)	−0.0091 (7)	0.0000 (7)
C2	0.0224 (8)	0.0348 (10)	0.0314 (9)	0.0015 (7)	−0.0049 (7)	0.0015 (8)
C3	0.0375 (9)	0.0385 (11)	0.0327 (10)	0.0018 (8)	0.0034 (8)	0.0024 (8)
C4	0.0305 (9)	0.0338 (10)	0.0315 (9)	−0.0003 (8)	−0.0060 (7)	0.0017 (8)
C5	0.0296 (9)	0.0422 (12)	0.0448 (11)	0.0062 (8)	−0.0025 (8)	−0.0038 (9)
C6	0.0345 (9)	0.0366 (11)	0.0409 (10)	0.0077 (8)	−0.0015 (8)	−0.0086 (9)
C7	0.0474 (11)	0.0338 (11)	0.0495 (12)	0.0070 (9)	−0.0061 (9)	−0.0049 (9)
C8	0.0486 (12)	0.0356 (12)	0.0721 (16)	−0.0019 (9)	−0.0035 (11)	−0.0132 (11)
C9	0.0410 (11)	0.0564 (15)	0.0635 (15)	0.0015 (11)	−0.0079 (11)	−0.0294 (12)
C10	0.0497 (13)	0.0732 (18)	0.0401 (11)	0.0109 (12)	−0.0083 (10)	−0.0189 (11)
C11	0.0457 (12)	0.0535 (14)	0.0399 (11)	0.0030 (10)	0.0022 (9)	−0.0080 (10)
C12	0.0237 (8)	0.0333 (10)	0.0299 (9)	0.0004 (7)	−0.0056 (7)	0.0018 (7)
C13	0.0299 (9)	0.0346 (10)	0.0400 (10)	0.0011 (8)	−0.0060 (8)	0.0054 (8)
C14	0.0286 (8)	0.0389 (11)	0.0411 (10)	−0.0012 (8)	−0.0028 (8)	0.0036 (9)
C15	0.0306 (9)	0.0458 (12)	0.0348 (10)	−0.0003 (8)	−0.0034 (7)	0.0006 (9)
C16	0.0385 (10)	0.0458 (12)	0.0374 (10)	0.0000 (9)	−0.0021 (8)	0.0009 (9)
C17	0.0372 (10)	0.0530 (13)	0.0369 (11)	−0.0007 (9)	−0.0035 (8)	0.0009 (9)
C18	0.0455 (11)	0.0514 (13)	0.0334 (10)	−0.0029 (9)	−0.0008 (9)	0.0004 (9)
C19	0.0458 (12)	0.0713 (17)	0.0375 (12)	−0.0054 (11)	−0.0052 (9)	−0.0016 (11)
C20	0.0699 (16)	0.083 (2)	0.0387 (13)	−0.0004 (14)	−0.0107 (11)	−0.0018 (12)
C21	0.0247 (8)	0.0272 (9)	0.0300 (8)	−0.0003 (7)	−0.0039 (6)	0.0002 (8)
C22	0.0298 (8)	0.0549 (13)	0.0275 (8)	0.0007 (9)	−0.0021 (7)	−0.0023 (9)
C23	0.0286 (8)	0.0460 (12)	0.0286 (8)	−0.0033 (8)	−0.0036 (7)	−0.0016 (8)
C24	0.0317 (9)	0.0488 (13)	0.0314 (9)	−0.0035 (9)	−0.0043 (7)	0.0000 (9)
C25	0.0348 (9)	0.0504 (13)	0.0301 (9)	−0.0016 (9)	−0.0061 (7)	−0.0036 (9)
C26	0.0381 (9)	0.0513 (13)	0.0318 (9)	−0.0038 (9)	−0.0049 (7)	0.0006 (9)
C27	0.0399 (10)	0.0546 (14)	0.0326 (9)	−0.0008 (9)	−0.0065 (8)	0.0007 (9)
C28	0.0488 (12)	0.0638 (16)	0.0334 (10)	−0.0009 (10)	−0.0079 (9)	0.0017 (10)
C29	0.0607 (14)	0.0780 (17)	0.0344 (11)	0.0084 (13)	−0.0121 (10)	0.0003 (11)

Geometric parameters (Å, º) top

N1—C3	1.448 (3)	C14—H14B	0.9900
N1—C5	1.476 (3)	C15—C16	1.519 (3)
N1—C4	1.478 (2)	C15—H15A	0.9900
N2—C12	1.319 (2)	C15—H15B	0.9900
N2—C13	1.461 (2)	C16—C17	1.504 (3)
N2—HN2	0.8800	C16—H16A	0.9900
N3—C21	1.312 (2)	C16—H16B	0.9900
N3—C22	1.463 (2)	C17—C18	1.524 (3)
N3—HN3	0.8800	C17—H17A	0.9900
O1—C12	1.367 (2)	C17—H17B	0.9900
O1—C2	1.434 (2)	C18—C19	1.486 (3)
O2—C12	1.220 (2)	C18—H18A	0.9900
O3—C21	1.374 (2)	C18—H18B	0.9900
O3—C1	1.4295 (19)	C19—C20	1.522 (3)
O4—C21	1.2206 (19)	C19—H19A	0.9900
C1—C4	1.526 (3)	C19—H19B	0.9900
C1—C2	1.544 (3)	C20—H20A	0.9800
C1—H1	1.0000	C20—H20B	0.9800
C2—C3	1.536 (3)	C20—H20C	0.9800
C2—H2	1.0000	C22—C23	1.485 (2)
C3—H3A	0.9900	C22—H22B	0.9900
C3—H3B	0.9900	C22—H22A	0.9900
C4—H4B	0.9900	C23—C24	1.533 (2)
C4—H4A	0.9900	C23—H23A	0.9500
C5—C6	1.499 (3)	C23—H23B	0.9858
C5—H5A	0.9900	C24—C25	1.493 (2)
C5—H5B	0.9900	C24—H24A	0.9900
C6—C11	1.378 (3)	C24—H24B	0.9900
C6—C7	1.392 (3)	C25—C26	1.533 (3)
C7—C8	1.372 (3)	C25—H25A	0.9900
C7—H7	0.9500	C25—H25B	0.9900
C8—C9	1.367 (4)	C26—C27	1.491 (3)
C8—H8	0.9500	C26—H26B	0.9900
C9—C10	1.383 (4)	C26—H26A	0.9900
C9—H9	0.9500	C27—C28	1.531 (3)
C10—C11	1.386 (3)	C27—H27A	0.9900
C10—H10	0.9500	C27—H27B	0.9900
C11—H11	0.9500	C28—C29	1.491 (3)
C13—C14	1.517 (3)	C28—H28A	0.9900
C13—H13A	0.9900	C28—H28B	0.9900
C13—H13B	0.9900	C29—H29C	0.9800
C14—C15	1.507 (3)	C29—H29B	0.9800
C14—H14A	0.9900	C29—H29A	0.9800

C3—N1—C5	116.61 (15)	C17—C16—H16A	108.8
C3—N1—C4	103.91 (14)	C15—C16—H16A	108.8
C5—N1—C4	116.49 (15)	C17—C16—H16B	108.8
C12—N2—C13	120.59 (14)	C15—C16—H16B	108.8
C12—N2—HN2	119.7	H16A—C16—H16B	107.7
C13—N2—HN2	119.7	C16—C17—C18	113.03 (17)
C21—N3—C22	119.20 (14)	C16—C17—H17A	109.0
C21—N3—HN3	120.4	C18—C17—H17A	109.0
C22—N3—HN3	120.4	C16—C17—H17B	109.0
C12—O1—C2	114.85 (13)	C18—C17—H17B	109.0
C21—O3—C1	117.45 (12)	H17A—C17—H17B	107.8
O3—C1—C4	109.87 (14)	C19—C18—C17	112.86 (18)
O3—C1—C2	106.55 (14)	C19—C18—H18A	109.0
C4—C1—C2	103.44 (15)	C17—C18—H18A	109.0
O3—C1—H1	112.2	C19—C18—H18B	109.0
C4—C1—H1	112.2	C17—C18—H18B	109.0
C2—C1—H1	112.2	H18A—C18—H18B	107.8
O1—C2—C3	113.52 (14)	C18—C19—C20	113.3 (2)
O1—C2—C1	108.41 (14)	C18—C19—H19A	108.9
C3—C2—C1	105.31 (15)	C20—C19—H19A	108.9
O1—C2—H2	109.8	C18—C19—H19B	108.9
C3—C2—H2	109.8	C20—C19—H19B	108.9
C1—C2—H2	109.8	H19A—C19—H19B	107.7
N1—C3—C2	101.48 (14)	C19—C20—H20A	109.5
N1—C3—H3A	111.5	C19—C20—H20B	109.5
C2—C3—H3A	111.5	H20A—C20—H20B	109.5
N1—C3—H3B	111.5	C19—C20—H20C	109.5
C2—C3—H3B	111.5	H20A—C20—H20C	109.5
H3A—C3—H3B	109.3	H20B—C20—H20C	109.5
N1—C4—C1	103.00 (14)	O4—C21—N3	124.57 (16)
N1—C4—H4B	111.2	O4—C21—O3	125.44 (14)
C1—C4—H4B	111.2	N3—C21—O3	109.99 (14)
N1—C4—H4A	111.2	N3—C22—C23	111.00 (14)
C1—C4—H4A	111.2	N3—C22—H22B	109.4
H4B—C4—H4A	109.1	C23—C22—H22B	109.4
N1—C5—C6	115.41 (15)	N3—C22—H22A	109.4
N1—C5—H5A	108.4	C23—C22—H22A	109.4
C6—C5—H5A	108.4	H22B—C22—H22A	108.0
N1—C5—H5B	108.4	C22—C23—C24	110.76 (15)
C6—C5—H5B	108.4	C22—C23—H23A	124.6
H5A—C5—H5B	107.5	C24—C23—H23A	124.6
C11—C6—C7	119.19 (19)	C22—C23—H23B	109.2
C11—C6—C5	120.62 (19)	C24—C23—H23B	111.2
C7—C6—C5	120.18 (18)	H23A—C23—H23B	52.6
C8—C7—C6	121.5 (2)	C25—C24—C23	113.90 (15)
C8—C7—H7	119.2	C25—C24—H24A	108.8
C6—C7—H7	119.2	C23—C24—H24A	108.8
C7—C8—C9	118.9 (2)	C25—C24—H24B	108.8
C7—C8—H8	120.5	C23—C24—H24B	108.8
C9—C8—H8	120.5	H24A—C24—H24B	107.7
C8—C9—C10	120.6 (2)	C24—C25—C26	112.11 (15)
C8—C9—H9	119.7	C24—C25—H25A	109.2
C10—C9—H9	119.7	C26—C25—H25A	109.2
C11—C10—C9	120.5 (2)	C24—C25—H25B	109.2
C11—C10—H10	119.7	C26—C25—H25B	109.2
C9—C10—H10	119.7	H25A—C25—H25B	107.9
C6—C11—C10	119.2 (2)	C27—C26—C25	113.93 (16)
C6—C11—H11	120.4	C27—C26—H26B	108.8
C10—C11—H11	120.4	C25—C26—H26B	108.8
O2—C12—N2	125.23 (17)	C27—C26—H26A	108.8
O2—C12—O1	123.74 (15)	C25—C26—H26A	108.8
N2—C12—O1	111.02 (14)	H26B—C26—H26A	107.7
N2—C13—C14	114.50 (16)	C26—C27—C28	113.02 (17)
N2—C13—H13A	108.6	C26—C27—H27A	109.0
C14—C13—H13A	108.6	C28—C27—H27A	109.0
N2—C13—H13B	108.6	C26—C27—H27B	109.0
C14—C13—H13B	108.6	C28—C27—H27B	109.0
H13A—C13—H13B	107.6	H27A—C27—H27B	107.8
C15—C14—C13	113.22 (15)	C29—C28—C27	113.10 (19)
C15—C14—H14A	108.9	C29—C28—H28A	109.0
C13—C14—H14A	108.9	C27—C28—H28A	109.0
C15—C14—H14B	108.9	C29—C28—H28B	109.0
C13—C14—H14B	108.9	C27—C28—H28B	109.0
H14A—C14—H14B	107.7	H28A—C28—H28B	107.8
C14—C15—C16	111.59 (16)	C28—C29—H29C	109.5
C14—C15—H15A	109.3	C28—C29—H29B	109.5
C16—C15—H15A	109.3	H29C—C29—H29B	109.5
C14—C15—H15B	109.3	C28—C29—H29A	109.5
C16—C15—H15B	109.3	H29C—C29—H29A	109.5
H15A—C15—H15B	108.0	H29B—C29—H29A	109.5
C17—C16—C15	113.81 (16)

C21—O3—C1—C4	105.90 (18)	C7—C6—C11—C10	−1.5 (3)
C21—O3—C1—C2	−142.69 (16)	C5—C6—C11—C10	177.36 (19)
C12—O1—C2—C3	84.66 (19)	C9—C10—C11—C6	1.3 (3)
C12—O1—C2—C1	−158.70 (14)	C13—N2—C12—O2	1.1 (3)
O3—C1—C2—O1	120.31 (15)	C13—N2—C12—O1	−177.95 (15)
C4—C1—C2—O1	−123.87 (14)	C2—O1—C12—O2	2.6 (2)
O3—C1—C2—C3	−117.88 (15)	C2—O1—C12—N2	−178.32 (15)
C4—C1—C2—C3	−2.06 (17)	C12—N2—C13—C14	−87.7 (2)
C5—N1—C3—C2	−176.27 (15)	N2—C13—C14—C15	−74.3 (2)
C4—N1—C3—C2	−46.63 (17)	C13—C14—C15—C16	−177.03 (17)
O1—C2—C3—N1	147.80 (14)	C14—C15—C16—C17	175.20 (18)
C1—C2—C3—N1	29.35 (17)	C15—C16—C17—C18	−178.06 (19)
C3—N1—C4—C1	46.10 (16)	C16—C17—C18—C19	179.0 (2)
C5—N1—C4—C1	175.81 (14)	C17—C18—C19—C20	−179.1 (2)
O3—C1—C4—N1	87.93 (16)	C22—N3—C21—O4	3.2 (3)
C2—C1—C4—N1	−25.51 (15)	C22—N3—C21—O3	−177.17 (16)
C3—N1—C5—C6	68.1 (2)	C1—O3—C21—O4	7.8 (3)
C4—N1—C5—C6	−55.2 (2)	C1—O3—C21—N3	−171.84 (16)
N1—C5—C6—C11	−88.4 (2)	C21—N3—C22—C23	−178.32 (17)
N1—C5—C6—C7	90.5 (2)	N3—C22—C23—C24	175.15 (16)
C11—C6—C7—C8	0.6 (3)	C22—C23—C24—C25	179.04 (18)
C5—C6—C7—C8	−178.28 (19)	C23—C24—C25—C26	−179.07 (17)
C6—C7—C8—C9	0.5 (3)	C24—C25—C26—C27	177.99 (19)
C7—C8—C9—C10	−0.7 (3)	C25—C26—C27—C28	−176.83 (19)
C8—C9—C10—C11	−0.2 (3)	C26—C27—C28—C29	174.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—HN2···O2ⁱ	0.88	2.01	2.8449 (19)	157
N3—HN3···O4ⁱⁱ	0.88	2.15	3.0211 (19)	172

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

Experimental details

Crystal data
Chemical formula	C₂₉H₄₉N₃O₄
M_r	503.71
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	150
a, b, c (Å)	5.039 (1), 15.825 (1), 18.330 (1)
β (°)	90.884 (1)
V (Å³)	1461.5 (3)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.60
Crystal size (mm)	0.32 × 0.22 × 0.18

Data collection
Diffractometer	Oxford Diffraction XCALIBUR PX Ultra CCD
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2006)
T_min, T_max	0.851, 0.898
No. of measured, independent and observed [I > 2σ(I)] reflections	23018, 5438, 4359
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.096, 1.08
No. of reflections	5438
No. of parameters	327
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.22
Absolute structure	Flack (1983), with how many Friedel pairs?
Absolute structure parameter	−0.02 (16)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis CCD, CrysAlis RED (Oxford Diffraction, 2006), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.

Selected geometric parameters (Å, º) top

N2—C12	1.319 (2)	N3—C22	1.463 (2)
N2—C13	1.461 (2)	N3—HN3	0.8800
N2—HN2	0.8800	O2—C12	1.220 (2)
N3—C21	1.312 (2)	O4—C21	1.2206 (19)

N2—C12—O1	111.02 (14)	O4—C21—N3	124.57 (16)

C13—N2—C12—O2	1.1 (3)	C1—O3—C21—O4	7.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—HN2···O2ⁱ	0.88	2.01	2.8449 (19)	156.8
N3—HN3···O4ⁱⁱ	0.88	2.15	3.0211 (19)	171.7

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

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page