(S)-(Z)-Methyl 2-[2,3-bis-(benzyl-oxy-carbon-yl)guanidino]-4-methyl-penta-no-ate.

The title mol-ecule, C(24)H(29)N(3)O(6), has a nearly planar ten-atom C(3)N(3)O(4) core, on account of both N-H groups forming six-membered-ring intra-molecular hydrogen bonds to carbamate carbonyl O atoms. The absolute configuration was determined from resonant scattering of light atoms in Mo Kα radiation, agreeing with the configuration of starting materials.

Related literature

For related structures, see: Travlos & White (1994 ▶); Feichtinger et al. (1998 ▶); Marsh (2002 ▶). For graph sets, see: Etter (1990 ▶). For absolute configuration based on resonant scattering from light atoms, see: Hooft et al. (2008 ▶); Fronczek (2010 ▶); Lutz & van Krieken (2010 ▶); Thompson et al. (2008 ▶).

Experimental

Crystal data

C24H29N3O6

M = 455.50

Orthorhombic,

a = 7.7203 (5) Å

b = 14.2043 (10) Å

c = 21.280 (2) Å

V = 2333.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 90 K

0.30 × 0.28 × 0.15 mm

Data collection

Nonius KappaCCD diffractometer with an Oxford Cryosystems Cryostream cooler

43001 measured reflections

10411 independent reflections

9219 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.101

S = 1.02

10411 reflections

307 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.28 e Å−3

Absolute structure: Flack (1983 ▶), 4545 Friedel pairs

Flack parameter: 0.2 (5)

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810050130/om2385sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050130/om2385Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C24H29N3O6	F(000) = 968
Mr = 455.50	Dx = 1.297 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5760 reflections
a = 7.7203 (5) Å	θ = 2.5–36.1°
b = 14.2043 (10) Å	µ = 0.09 mm−1
c = 21.280 (2) Å	T = 90 K
V = 2333.6 (3) Å3	Fragment, colourless
Z = 4	0.30 × 0.28 × 0.15 mm

Nonius KappaCCD (with an Oxford Cryosystems Cryostream cooler) diffractometer	9219 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.056
graphite	θmax = 36.1°, θmin = 2.8°
ω and φ scans	h = −12→12
43001 measured reflections	k = −22→22
10411 independent reflections	l = −34→34

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.101	w = 1/[σ2(Fo2) + (0.0473P)2 + 0.6349P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
10411 reflections	Δρmax = 0.33 e Å−3
307 parameters	Δρmin = −0.28 e Å−3
0 restraints	Absolute structure: Flack (1983), 4545 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.2 (5)

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.

	x	y	z	Uiso*/Ueq
O1	0.58734 (12)	0.48105 (6)	0.79229 (4)	0.01853 (16)
O2	0.69349 (11)	0.37173 (6)	0.72588 (4)	0.01797 (15)
O3	0.66892 (11)	0.75163 (5)	0.55412 (3)	0.01520 (14)
O4	0.70303 (12)	0.64048 (5)	0.47943 (4)	0.01833 (15)
O5	0.57441 (13)	0.31412 (5)	0.54332 (4)	0.02052 (17)
O6	0.65667 (11)	0.35908 (5)	0.44569 (3)	0.01435 (13)
N1	0.55713 (12)	0.46022 (6)	0.62459 (4)	0.01239 (14)
H1N	0.555 (2)	0.4008 (11)	0.6200 (7)	0.015*
N2	0.62092 (12)	0.60509 (5)	0.58336 (4)	0.01166 (14)
N3	0.63981 (13)	0.46856 (6)	0.51925 (4)	0.01316 (15)
H3N	0.665 (2)	0.5094 (11)	0.4900 (7)	0.016*
C1	0.66331 (18)	0.43149 (9)	0.84503 (5)	0.0225 (2)
H1A	0.6032	0.3714	0.8511	0.034*
H1B	0.6519	0.4699	0.8831	0.034*
H1C	0.7862	0.4197	0.8366	0.034*
C2	0.61124 (13)	0.44220 (7)	0.73573 (4)	0.01164 (15)
C3	0.51657 (13)	0.49959 (7)	0.68598 (4)	0.01065 (15)
H3	0.5592	0.5660	0.6876	0.013*
C4	0.32033 (13)	0.49892 (7)	0.69888 (4)	0.01355 (16)
H4A	0.2779	0.4334	0.6954	0.016*
H4B	0.3005	0.5198	0.7427	0.016*
C5	0.21252 (14)	0.56144 (7)	0.65481 (5)	0.01525 (17)
H5	0.2404	0.5437	0.6105	0.018*
C6	0.01921 (16)	0.54251 (9)	0.66614 (7)	0.0256 (2)
H6A	−0.0103	0.5586	0.7096	0.038*
H6B	−0.0055	0.4758	0.6587	0.038*
H6C	−0.0499	0.5811	0.6374	0.038*
C7	0.25316 (14)	0.66599 (7)	0.66332 (5)	0.01623 (18)
H7A	0.1775	0.7033	0.6360	0.024*
H7B	0.3744	0.6778	0.6522	0.024*
H7C	0.2336	0.6839	0.7072	0.024*
C8	0.60582 (13)	0.51301 (6)	0.57593 (4)	0.01072 (15)
C9	0.66760 (13)	0.66107 (7)	0.53418 (4)	0.01203 (15)
C10	0.70649 (16)	0.82125 (7)	0.50644 (5)	0.01594 (18)
H10A	0.6129	0.8227	0.4747	0.019*
H10B	0.8168	0.8061	0.4850	0.019*
C11	0.71972 (14)	0.91503 (7)	0.53912 (5)	0.01436 (17)
C12	0.83270 (16)	0.92721 (8)	0.58972 (5)	0.01901 (19)
H12	0.9022	0.8761	0.6036	0.023*
C13	0.84373 (17)	1.01415 (9)	0.61988 (6)	0.0235 (2)
H13	0.9205	1.0221	0.6544	0.028*
C14	0.74245 (17)	1.08929 (8)	0.59950 (6)	0.0243 (2)
H14	0.7502	1.1485	0.6201	0.029*
C15	0.63033 (17)	1.07768 (7)	0.54924 (6)	0.0220 (2)
H15	0.5616	1.1290	0.5353	0.026*
C16	0.61826 (16)	0.99065 (7)	0.51914 (5)	0.01785 (18)
H16	0.5406	0.9828	0.4849	0.021*
C17	0.61893 (14)	0.37440 (7)	0.50618 (5)	0.01343 (16)
C18	0.63343 (15)	0.26163 (7)	0.42515 (5)	0.01528 (18)
H18A	0.5126	0.2412	0.4326	0.018*
H18B	0.7119	0.2194	0.4489	0.018*
C19	0.67470 (14)	0.25779 (6)	0.35627 (4)	0.01216 (15)
C20	0.55057 (14)	0.22770 (7)	0.31311 (5)	0.01544 (17)
H20	0.4373	0.2120	0.3270	0.019*
C21	0.59258 (16)	0.22057 (8)	0.24956 (5)	0.0188 (2)
H21	0.5084	0.1988	0.2204	0.023*
C22	0.75696 (16)	0.24510 (8)	0.22862 (5)	0.0190 (2)
H22	0.7849	0.2410	0.1852	0.023*
C23	0.88041 (15)	0.27570 (7)	0.27170 (5)	0.01767 (18)
H23	0.9928	0.2928	0.2576	0.021*
C24	0.84025 (14)	0.28140 (7)	0.33530 (5)	0.01503 (17)
H24	0.9257	0.3014	0.3645	0.018*

	U11	U22	U33	U12	U13	U23
O1	0.0276 (4)	0.0184 (3)	0.0095 (3)	0.0087 (3)	−0.0024 (3)	−0.0005 (3)
O2	0.0190 (4)	0.0179 (3)	0.0170 (3)	0.0076 (3)	0.0007 (3)	0.0004 (3)
O3	0.0251 (4)	0.0083 (3)	0.0122 (3)	−0.0017 (3)	0.0044 (3)	0.0002 (2)
O4	0.0303 (4)	0.0128 (3)	0.0120 (3)	−0.0029 (3)	0.0067 (3)	−0.0006 (2)
O5	0.0370 (5)	0.0108 (3)	0.0137 (3)	−0.0018 (3)	0.0072 (3)	−0.0001 (3)
O6	0.0222 (4)	0.0101 (3)	0.0107 (3)	−0.0015 (3)	0.0039 (3)	−0.0022 (2)
N1	0.0194 (4)	0.0083 (3)	0.0095 (3)	−0.0002 (3)	0.0026 (3)	−0.0005 (2)
N2	0.0163 (4)	0.0084 (3)	0.0103 (3)	−0.0011 (3)	0.0016 (3)	0.0001 (2)
N3	0.0209 (4)	0.0087 (3)	0.0099 (3)	−0.0009 (3)	0.0035 (3)	−0.0003 (2)
C1	0.0282 (6)	0.0277 (5)	0.0115 (4)	0.0081 (5)	−0.0040 (4)	0.0028 (4)
C2	0.0121 (4)	0.0126 (4)	0.0103 (3)	−0.0008 (3)	0.0002 (3)	0.0011 (3)
C3	0.0141 (4)	0.0096 (3)	0.0083 (3)	0.0009 (3)	0.0012 (3)	0.0000 (3)
C4	0.0127 (4)	0.0144 (4)	0.0136 (4)	0.0011 (3)	0.0005 (3)	0.0016 (3)
C5	0.0156 (4)	0.0147 (4)	0.0154 (4)	0.0030 (3)	−0.0035 (3)	−0.0015 (3)
C6	0.0152 (5)	0.0239 (5)	0.0377 (7)	0.0013 (4)	−0.0054 (5)	−0.0014 (5)
C7	0.0177 (5)	0.0139 (4)	0.0171 (4)	0.0043 (3)	−0.0029 (3)	−0.0012 (3)
C8	0.0124 (4)	0.0105 (3)	0.0092 (3)	0.0006 (3)	0.0005 (3)	−0.0004 (3)
C9	0.0128 (4)	0.0100 (3)	0.0132 (4)	−0.0004 (3)	0.0006 (3)	0.0002 (3)
C10	0.0252 (5)	0.0099 (4)	0.0127 (4)	−0.0022 (3)	0.0047 (4)	0.0019 (3)
C11	0.0193 (4)	0.0094 (3)	0.0144 (4)	−0.0018 (3)	0.0053 (3)	0.0004 (3)
C12	0.0218 (5)	0.0158 (4)	0.0195 (4)	−0.0004 (4)	0.0029 (4)	−0.0013 (4)
C13	0.0238 (5)	0.0228 (5)	0.0239 (5)	−0.0051 (4)	0.0040 (4)	−0.0084 (4)
C14	0.0280 (6)	0.0147 (4)	0.0302 (6)	−0.0059 (4)	0.0126 (5)	−0.0070 (4)
C15	0.0289 (6)	0.0111 (4)	0.0259 (5)	0.0028 (4)	0.0118 (4)	0.0016 (4)
C16	0.0223 (5)	0.0137 (4)	0.0175 (4)	0.0019 (4)	0.0059 (4)	0.0024 (3)
C17	0.0180 (4)	0.0108 (4)	0.0115 (4)	0.0009 (3)	0.0024 (3)	−0.0022 (3)
C18	0.0231 (5)	0.0096 (4)	0.0132 (4)	−0.0026 (3)	0.0042 (3)	−0.0027 (3)
C19	0.0155 (4)	0.0097 (3)	0.0113 (3)	0.0005 (3)	0.0013 (3)	−0.0017 (3)
C20	0.0140 (4)	0.0146 (4)	0.0178 (4)	0.0018 (3)	−0.0006 (3)	−0.0039 (3)
C21	0.0219 (5)	0.0186 (4)	0.0158 (4)	0.0056 (4)	−0.0070 (4)	−0.0041 (4)
C22	0.0287 (6)	0.0165 (4)	0.0118 (4)	0.0045 (4)	0.0010 (4)	0.0008 (3)
C23	0.0199 (5)	0.0169 (4)	0.0163 (4)	−0.0009 (4)	0.0045 (4)	0.0015 (3)
C24	0.0163 (4)	0.0150 (4)	0.0138 (4)	−0.0025 (3)	0.0005 (3)	−0.0005 (3)

O1—C2	1.3369 (12)	C7—H7A	0.9800
O1—C1	1.4488 (13)	C7—H7B	0.9800
O2—C2	1.2037 (12)	C7—H7C	0.9800
O3—C9	1.3546 (12)	C10—C11	1.5061 (14)
O3—C10	1.4462 (12)	C10—H10A	0.9900
O4—C9	1.2321 (12)	C10—H10B	0.9900
O5—C17	1.2147 (12)	C11—C16	1.3958 (15)
O6—C17	1.3377 (12)	C11—C12	1.3966 (16)
O6—C18	1.4626 (12)	C12—C13	1.3943 (16)
N1—C8	1.3326 (12)	C12—H12	0.9500
N1—C3	1.4550 (12)	C13—C14	1.3923 (19)
N1—H1N	0.849 (16)	C13—H13	0.9500
N2—C8	1.3225 (12)	C14—C15	1.386 (2)
N2—C9	1.3628 (12)	C14—H14	0.9500
N3—C17	1.3756 (12)	C15—C16	1.3954 (15)
N3—C8	1.3864 (12)	C15—H15	0.9500
N3—H3N	0.873 (16)	C16—H16	0.9500
C1—H1A	0.9800	C18—C19	1.5011 (14)
C1—H1B	0.9800	C18—H18A	0.9900
C1—H1C	0.9800	C18—H18B	0.9900
C2—C3	1.5230 (13)	C19—C20	1.3944 (14)
C3—C4	1.5397 (14)	C19—C24	1.3947 (15)
C3—H3	1.0000	C20—C21	1.3944 (16)
C4—C5	1.5366 (14)	C20—H20	0.9500
C4—H4A	0.9900	C21—C22	1.3895 (18)
C4—H4B	0.9900	C21—H21	0.9500
C5—C7	1.5286 (15)	C22—C23	1.3920 (17)
C5—C6	1.5355 (17)	C22—H22	0.9500
C5—H5	1.0000	C23—C24	1.3910 (15)
C6—H6A	0.9800	C23—H23	0.9500
C6—H6B	0.9800	C24—H24	0.9500
C6—H6C	0.9800
C2—O1—C1	116.17 (8)	O4—C9—N2	130.27 (9)
C9—O3—C10	115.54 (8)	O3—C9—N2	108.40 (8)
C17—O6—C18	114.50 (8)	O3—C10—C11	107.12 (8)
C8—N1—C3	122.83 (8)	O3—C10—H10A	110.3
C8—N1—H1N	118.5 (11)	C11—C10—H10A	110.3
C3—N1—H1N	118.6 (11)	O3—C10—H10B	110.3
C8—N2—C9	120.56 (8)	C11—C10—H10B	110.3
C17—N3—C8	126.62 (8)	H10A—C10—H10B	108.5
C17—N3—H3N	121.8 (10)	C16—C11—C12	119.34 (10)
C8—N3—H3N	111.1 (10)	C16—C11—C10	120.13 (10)
O1—C1—H1A	109.5	C12—C11—C10	120.53 (10)
O1—C1—H1B	109.5	C13—C12—C11	120.18 (11)
H1A—C1—H1B	109.5	C13—C12—H12	119.9
O1—C1—H1C	109.5	C11—C12—H12	119.9
H1A—C1—H1C	109.5	C14—C13—C12	120.09 (12)
H1B—C1—H1C	109.5	C14—C13—H13	120.0
O2—C2—O1	124.94 (9)	C12—C13—H13	120.0
O2—C2—C3	125.25 (9)	C15—C14—C13	119.99 (11)
O1—C2—C3	109.80 (8)	C15—C14—H14	120.0
N1—C3—C2	108.37 (8)	C13—C14—H14	120.0
N1—C3—C4	111.68 (8)	C14—C15—C16	120.10 (11)
C2—C3—C4	110.18 (8)	C14—C15—H15	120.0
N1—C3—H3	108.9	C16—C15—H15	120.0
C2—C3—H3	108.9	C15—C16—C11	120.30 (11)
C4—C3—H3	108.9	C15—C16—H16	119.9
C5—C4—C3	114.87 (8)	C11—C16—H16	119.9
C5—C4—H4A	108.5	O5—C17—O6	124.96 (9)
C3—C4—H4A	108.5	O5—C17—N3	125.94 (9)
C5—C4—H4B	108.5	O6—C17—N3	109.10 (8)
C3—C4—H4B	108.5	O6—C18—C19	107.47 (8)
H4A—C4—H4B	107.5	O6—C18—H18A	110.2
C7—C5—C6	110.55 (9)	C19—C18—H18A	110.2
C7—C5—C4	112.21 (8)	O6—C18—H18B	110.2
C6—C5—C4	109.24 (9)	C19—C18—H18B	110.2
C7—C5—H5	108.2	H18A—C18—H18B	108.5
C6—C5—H5	108.2	C20—C19—C24	119.53 (9)
C4—C5—H5	108.2	C20—C19—C18	120.56 (9)
C5—C6—H6A	109.5	C24—C19—C18	119.88 (9)
C5—C6—H6B	109.5	C19—C20—C21	120.08 (10)
H6A—C6—H6B	109.5	C19—C20—H20	120.0
C5—C6—H6C	109.5	C21—C20—H20	120.0
H6A—C6—H6C	109.5	C22—C21—C20	120.35 (10)
H6B—C6—H6C	109.5	C22—C21—H21	119.8
C5—C7—H7A	109.5	C20—C21—H21	119.8
C5—C7—H7B	109.5	C21—C22—C23	119.50 (10)
H7A—C7—H7B	109.5	C21—C22—H22	120.2
C5—C7—H7C	109.5	C23—C22—H22	120.2
H7A—C7—H7C	109.5	C24—C23—C22	120.42 (11)
H7B—C7—H7C	109.5	C24—C23—H23	119.8
N2—C8—N1	119.24 (8)	C22—C23—H23	119.8
N2—C8—N3	122.53 (8)	C23—C24—C19	120.10 (10)
N1—C8—N3	118.24 (8)	C23—C24—H24	119.9
O4—C9—O3	121.32 (9)	C19—C24—H24	119.9
C1—O1—C2—O2	−1.94 (16)	O3—C10—C11—C12	54.29 (13)
C1—O1—C2—C3	177.18 (9)	C16—C11—C12—C13	0.00 (16)
C8—N1—C3—C2	−132.15 (10)	C10—C11—C12—C13	−179.77 (10)
C8—N1—C3—C4	106.31 (11)	C11—C12—C13—C14	−0.20 (18)
O2—C2—C3—N1	−5.64 (14)	C12—C13—C14—C15	0.08 (18)
O1—C2—C3—N1	175.24 (8)	C13—C14—C15—C16	0.24 (18)
O2—C2—C3—C4	116.82 (11)	C14—C15—C16—C11	−0.45 (17)
O1—C2—C3—C4	−62.30 (11)	C12—C11—C16—C15	0.33 (16)
N1—C3—C4—C5	−64.38 (11)	C10—C11—C16—C15	−179.91 (10)
C2—C3—C4—C5	175.13 (8)	C18—O6—C17—O5	2.47 (16)
C3—C4—C5—C7	−65.68 (11)	C18—O6—C17—N3	−177.91 (9)
C3—C4—C5—C6	171.35 (9)	C8—N3—C17—O5	−3.52 (19)
C9—N2—C8—N1	−178.87 (9)	C8—N3—C17—O6	176.87 (10)
C9—N2—C8—N3	1.53 (15)	C17—O6—C18—C19	177.95 (9)
C3—N1—C8—N2	1.03 (15)	O6—C18—C19—C20	−120.63 (10)
C3—N1—C8—N3	−179.35 (9)	O6—C18—C19—C24	61.55 (12)
C17—N3—C8—N2	−176.29 (10)	C24—C19—C20—C21	0.56 (15)
C17—N3—C8—N1	4.11 (16)	C18—C19—C20—C21	−177.26 (9)
C10—O3—C9—O4	2.71 (15)	C19—C20—C21—C22	−1.28 (16)
C10—O3—C9—N2	−176.60 (9)	C20—C21—C22—C23	0.85 (16)
C8—N2—C9—O4	−0.78 (18)	C21—C22—C23—C24	0.28 (16)
C8—N2—C9—O3	178.44 (9)	C22—C23—C24—C19	−0.99 (16)
C9—O3—C10—C11	−174.34 (9)	C20—C19—C24—C23	0.56 (15)
O3—C10—C11—C16	−125.47 (10)	C18—C19—C24—C23	178.40 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O5	0.849 (16)	2.051 (16)	2.7047 (11)	133.3 (14)
N3—H3N···O4	0.873 (16)	1.898 (16)	2.6306 (11)	140.4 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O5	0.849 (16)	2.051 (16)	2.7047 (11)	133.3 (14)
N3—H3N⋯O4	0.873 (16)	1.898 (16)	2.6306 (11)	140.4 (14)