H-d-Phe-d-Pro-Gly methyl ester hydro-chloride monohydrate.

The conformation of the title tripeptide methyl ester hydro-chloride monohydrate, 1-[2-(methoxycarbonylmethylaminocarbonyl)pyrrolidin-1-ylcarbonyl]-2-phenylethanaminium chloride monohydrate, C(17)H(24)N(3)O(4) (+)·Cl(-)·H(2)O, is extended, but the structure cannot be classified as any typical secondary structure. Interactions through water molecules and chloride ions were formed, in addition to peptide-peptide hydrogen bonds, stabilizing the molecular packing. In comparison with the previous β-turn structure of the Phe-d-Pro-Gly analogue [Doi, Ichimiya & Asano (2007 ▶). Acta Cryst. E63, o4691], it was suggested that the difference between the chiralities of Phe and Pro residues of the title compound is important to induce the β-turn structure.

Related literature

For related literature, see: Cremer & Pople (1975 ▶); Doi, Fujita et al. (2001 ▶); Doi, Ichimiya et al. (2007 ▶); Espinosa & Gellman (2000 ▶); Llamas-Saiz et al. (2007 ▶); Tamaki et al. (1985 ▶); Yamada et al. (2002 ▶).

Experimental

Crystal data

C17H24N3O4 +·Cl−·H2O

M = 387.86

Orthorhombic,

a = 7.3707 (5) Å

b = 9.6667 (7) Å

c = 27.099 (2) Å

V = 1930.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 90 (2) K

0.40 × 0.35 × 0.35 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.874, T max = 0.923

23047 measured reflections

4553 independent reflections

4540 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.087

S = 0.85

4553 reflections

237 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 1920 Friedel pairs

Flack parameter: 0.03 (4)

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶);; data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680800528X/pv2069sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800528X/pv2069Isup2.hkl

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

C17H24N3O4+·Cl–·H2O	F000 = 824
Mr = 387.86	Dx = 1.334 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8392 reflections
a = 7.3707 (5) Å	θ = 2.3–28.3º
b = 9.6667 (7) Å	µ = 0.23 mm−1
c = 27.099 (2) Å	T = 90 (2) K
V = 1930.8 (2) Å3	Cubic, colourless
Z = 4	0.40 × 0.35 × 0.35 mm

Bruker SMART APEX CCD area-detector diffractometer	4553 independent reflections
Radiation source: MacScience, M18XCE rotating anode	4540 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.020
Detector resolution: 8.366 pixels mm-1	θmax = 27.9º
T = 90(2) K	θmin = 2.6º
ω–scan	h = −9→9
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	k = −12→12
Tmin = 0.874, Tmax = 0.923	l = −35→35
23047 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.032	w = 1/[σ2(Fo2) + (0.0703P)2 + 0.8632P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.088	(Δ/σ)max = 0.001
S = 0.85	Δρmax = 0.46 e Å−3
4553 reflections	Δρmin = −0.21 e Å−3
237 parameters	Extinction correction: none
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1920 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.03 (4)

Geometry. Cremer & Pople Puckering Parameters [D. Cremer & J.A. Pople, J.Amer.Chem.Soc., 97, (1975), 1354–1358] ——————————————————————- Q(2) = 0.3608 (15) A ng., Phi(2) = 293.1 (2) DegThe equation of the plane is of the form: P * x + Q * y + R * z - S = 0 where P, Q, R, S are constants and x, y, z are fractional coordinates.P = 5.153 (2), Q = 1.935 (5), R = -18.602 (8), S = -9.378 (8) Atom Distance x y z X Y Z * O(18): -0.0397 (9) 0.4138 0.9441 0.7191 3.0500 9.1267 19.4869 * N(20): 0.0350 (11) 0.2674 0.8185 0.6615 1.9711 7.9123 17.9252 * C(10): 0.0337 (12) 0.4982 0.7074 0.7139 3.6722 6.8378 19.3462 * C(18): -0.0103 (12) 0.3858 0.8324 0.6981 2.8434 8.0464 18.9186 * C(20): 0.0268 (13) 0.1632 0.9399 0.6457 1.2030 9.0862 17.4973 * C(23): -0.0454 (14) 0.2080 0.6914 0.6361 1.5330 6.6837 17.2377P = 4.443 (3), Q = 0.711 (4), R = 21.531 (8), S = 15.452 (5) Atom Distance x y z X Y Z * O(24): 0.1064 (11) 0.4222 1.0289 0.6015 3.1119 9.9466 16.2998 * N(30): 0.0315 (11) 0.2213 1.1812 0.6344 1.6313 11.4182 17.1924 * C(20): -0.1560 (13) 0.1632 0.9399 0.6457 1.2030 9.0862 17.4973 * C(24): 0.0232 (13) 0.2849 1.0527 0.6252 2.1002 10.1765 16.9412 * C(30): -0.1661 (14) 0.2878 1.2994 0.6076 2.1213 12.5607 16.4662 * H(30): 0.16108 0.1378 1.1928 0.6573 1.0157 11.5304 17.8122

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
Cl	0.11272 (5)	0.69212 (3)	0.784634 (14)	0.02274 (9)
N10	0.52851 (16)	0.72346 (11)	0.76814 (4)	0.0135 (2)
H10A	0.6034	0.7967	0.7737	0.020*
H10B	0.5802	0.6451	0.7803	0.020*
H10C	0.4203	0.7384	0.7834	0.020*
C10	0.49822 (17)	0.70736 (13)	0.71391 (4)	0.0131 (2)
H10	0.4307	0.6198	0.7070	0.016*
C11	0.68581 (19)	0.70458 (16)	0.68855 (5)	0.0175 (3)
H11A	0.7301	0.8008	0.6851	0.021*
H11B	0.7720	0.6545	0.7101	0.021*
C12	0.68628 (19)	0.63705 (14)	0.63820 (5)	0.0165 (3)
C13	0.6299 (2)	0.70899 (16)	0.59619 (5)	0.0199 (3)
H13	0.5899	0.8021	0.5990	0.024*
C14	0.6322 (2)	0.6449 (2)	0.55034 (6)	0.0310 (4)
H14	0.5924	0.6939	0.5219	0.037*
C15	0.6927 (3)	0.5092 (2)	0.54597 (7)	0.0399 (5)
H15	0.6951	0.4658	0.5145	0.048*
C16	0.7488 (3)	0.43792 (18)	0.58701 (8)	0.0391 (5)
H16	0.7901	0.3452	0.5839	0.047*
C17	0.7457 (2)	0.50079 (16)	0.63329 (7)	0.0261 (3)
H17	0.7841	0.4507	0.6616	0.031*
C18	0.38577 (18)	0.83238 (13)	0.69813 (4)	0.0132 (2)
O18	0.41380 (14)	0.94414 (10)	0.71910 (3)	0.0177 (2)
N20	0.26742 (16)	0.81851 (11)	0.66147 (4)	0.0138 (2)
C20	0.16322 (18)	0.93995 (13)	0.64568 (5)	0.0140 (3)
H20	0.0887	0.9764	0.6736	0.017*
C22	0.1285 (2)	0.74806 (14)	0.58840 (5)	0.0187 (3)
H22A	0.0379	0.6835	0.5744	0.022*
H22B	0.2248	0.7646	0.5636	0.022*
C21	0.0392 (2)	0.88425 (14)	0.60427 (5)	0.0183 (3)
H21A	−0.0852	0.8679	0.6167	0.022*
H21B	0.0335	0.9501	0.5763	0.022*
C23	0.20798 (19)	0.69142 (14)	0.63610 (5)	0.0160 (3)
H23A	0.1153	0.6413	0.6556	0.019*
H23B	0.3115	0.6289	0.6295	0.019*
C24	0.28494 (18)	1.05274 (13)	0.62516 (5)	0.0143 (2)
O24	0.42220 (15)	1.02895 (11)	0.60149 (4)	0.0226 (2)
N30	0.22132 (17)	1.18119 (12)	0.63443 (4)	0.0175 (2)
H30	0.1378	1.1928	0.6573	0.021*
C30	0.2878 (2)	1.29938 (15)	0.60763 (5)	0.0206 (3)
H30A	0.4206	1.2903	0.6031	0.025*
H30B	0.2650	1.3841	0.6272	0.025*
C31	0.1982 (2)	1.31382 (14)	0.55761 (5)	0.0183 (3)
O31	0.09911 (18)	1.22970 (12)	0.53927 (4)	0.0269 (2)
O32	0.24639 (17)	1.43362 (11)	0.53707 (4)	0.0248 (2)
C32	0.1767 (3)	1.4570 (2)	0.48750 (6)	0.0367 (4)
H32A	0.2270	1.3875	0.4650	0.055*
H32B	0.2121	1.5496	0.4763	0.055*
H32C	0.0441	1.4498	0.4878	0.055*
O1	0.81122 (14)	0.92109 (10)	0.78001 (4)	0.0195 (2)
H1	0.9029	0.8722	0.7787	0.023*
H2	0.8324	0.9851	0.7638	0.023*

	U11	U22	U33	U12	U13	U23
Cl	0.01806 (16)	0.01737 (15)	0.03278 (18)	−0.00004 (13)	0.00761 (14)	−0.00212 (13)
N10	0.0160 (5)	0.0120 (5)	0.0123 (5)	0.0004 (4)	−0.0018 (4)	0.0010 (4)
C10	0.0151 (5)	0.0122 (5)	0.0119 (5)	0.0002 (5)	−0.0010 (5)	0.0010 (5)
C11	0.0148 (6)	0.0220 (7)	0.0157 (6)	−0.0005 (5)	0.0005 (5)	−0.0006 (5)
C12	0.0135 (5)	0.0168 (6)	0.0191 (6)	−0.0028 (5)	0.0032 (5)	−0.0043 (5)
C13	0.0174 (6)	0.0246 (7)	0.0178 (6)	−0.0043 (6)	0.0012 (5)	−0.0029 (5)
C14	0.0218 (7)	0.0511 (10)	0.0202 (7)	−0.0096 (8)	0.0021 (6)	−0.0081 (7)
C15	0.0281 (8)	0.0539 (12)	0.0375 (9)	−0.0133 (9)	0.0105 (7)	−0.0320 (9)
C16	0.0241 (8)	0.0245 (8)	0.0686 (13)	−0.0067 (7)	0.0142 (9)	−0.0251 (9)
C17	0.0175 (6)	0.0179 (7)	0.0429 (9)	−0.0013 (6)	0.0049 (7)	−0.0024 (6)
C18	0.0145 (5)	0.0123 (5)	0.0127 (5)	−0.0018 (5)	0.0024 (5)	0.0026 (4)
O18	0.0226 (5)	0.0122 (4)	0.0182 (4)	−0.0010 (4)	−0.0045 (4)	0.0000 (4)
N20	0.0166 (5)	0.0092 (5)	0.0157 (5)	−0.0006 (4)	−0.0014 (4)	0.0010 (4)
C20	0.0162 (6)	0.0119 (6)	0.0140 (5)	0.0011 (5)	0.0000 (5)	0.0023 (4)
C22	0.0217 (7)	0.0187 (6)	0.0157 (6)	−0.0025 (5)	−0.0052 (5)	−0.0013 (5)
C21	0.0182 (6)	0.0174 (6)	0.0194 (6)	−0.0035 (5)	−0.0053 (5)	0.0025 (5)
C23	0.0174 (6)	0.0124 (6)	0.0183 (6)	−0.0031 (5)	−0.0027 (5)	−0.0003 (5)
C24	0.0170 (6)	0.0130 (6)	0.0130 (5)	−0.0010 (5)	−0.0026 (5)	0.0017 (5)
O24	0.0220 (5)	0.0192 (5)	0.0266 (5)	−0.0012 (4)	0.0077 (4)	0.0041 (4)
N30	0.0227 (6)	0.0128 (5)	0.0169 (5)	−0.0005 (5)	0.0011 (4)	0.0021 (4)
C30	0.0268 (7)	0.0137 (6)	0.0214 (6)	−0.0047 (6)	−0.0040 (5)	0.0038 (5)
C31	0.0215 (6)	0.0153 (6)	0.0181 (6)	0.0031 (6)	0.0039 (5)	0.0006 (5)
O31	0.0353 (6)	0.0221 (5)	0.0233 (5)	−0.0015 (5)	−0.0060 (5)	−0.0025 (4)
O32	0.0299 (6)	0.0211 (5)	0.0233 (5)	0.0000 (5)	−0.0007 (5)	0.0089 (4)
C32	0.0483 (11)	0.0399 (9)	0.0218 (7)	0.0074 (9)	0.0005 (7)	0.0101 (7)
O1	0.0186 (5)	0.0172 (4)	0.0227 (5)	0.0001 (4)	0.0005 (4)	0.0003 (4)

N10—C10	1.4947 (16)	C20—C21	1.5441 (18)
N10—H10A	0.9100	C20—H20	1.0000
N10—H10B	0.9100	C22—C23	1.5209 (18)
N10—H10C	0.9100	C22—C21	1.533 (2)
C10—C18	1.5265 (17)	C22—H22A	0.9900
C10—C11	1.5442 (18)	C22—H22B	0.9900
C10—H10	1.0000	C21—H21A	0.9900
C11—C12	1.5125 (18)	C21—H21B	0.9900
C11—H11A	0.9900	C23—H23A	0.9900
C11—H11B	0.9900	C23—H23B	0.9900
C12—C17	1.394 (2)	C24—O24	1.2197 (17)
C12—C13	1.397 (2)	C24—N30	1.3509 (17)
C13—C14	1.388 (2)	N30—C30	1.4397 (17)
C13—H13	0.9500	N30—H30	0.8800
C14—C15	1.391 (3)	C30—C31	1.5144 (19)
C14—H14	0.9500	C30—H30A	0.9900
C15—C16	1.372 (3)	C30—H30B	0.9900
C15—H15	0.9500	C31—O31	1.2006 (19)
C16—C17	1.394 (3)	C31—O32	1.3329 (17)
C16—H16	0.9500	O32—C32	1.456 (2)
C17—H17	0.9500	C32—H32A	0.9800
C18—O18	1.2381 (16)	C32—H32B	0.9800
C18—N20	1.3289 (17)	C32—H32C	0.9800
N20—C20	1.4666 (16)	O1—H1	0.825
N20—C23	1.4745 (17)	O1—H2	0.775
C20—C24	1.5176 (18)
C10—N10—H10A	109.5	N20—C20—H20	110.4
C10—N10—H10B	109.5	C24—C20—H20	110.4
H10A—N10—H10B	109.5	C21—C20—H20	110.4
C10—N10—H10C	109.5	C23—C22—C21	103.65 (11)
H10A—N10—H10C	109.5	C23—C22—H22A	111.0
H10B—N10—H10C	109.5	C21—C22—H22A	111.0
N10—C10—C18	105.90 (10)	C23—C22—H22B	111.0
N10—C10—C11	107.80 (10)	C21—C22—H22B	111.0
C18—C10—C11	112.04 (10)	H22A—C22—H22B	109.0
N10—C10—H10	110.3	C22—C21—C20	104.43 (11)
C18—C10—H10	110.3	C22—C21—H21A	110.9
C11—C10—H10	110.3	C20—C21—H21A	110.9
C12—C11—C10	114.26 (11)	C22—C21—H21B	110.9
C12—C11—H11A	108.7	C20—C21—H21B	110.9
C10—C11—H11A	108.7	H21A—C21—H21B	108.9
C12—C11—H11B	108.7	N20—C23—C22	102.16 (10)
C10—C11—H11B	108.7	N20—C23—H23A	111.3
H11A—C11—H11B	107.6	C22—C23—H23A	111.3
C17—C12—C13	119.06 (14)	N20—C23—H23B	111.3
C17—C12—C11	119.64 (14)	C22—C23—H23B	111.3
C13—C12—C11	121.30 (13)	H23A—C23—H23B	109.2
C14—C13—C12	120.25 (15)	O24—C24—N30	123.99 (13)
C14—C13—H13	119.9	O24—C24—C20	123.20 (12)
C12—C13—H13	119.9	N30—C24—C20	112.77 (12)
C13—C14—C15	120.05 (18)	C24—N30—C30	121.16 (12)
C13—C14—H14	120.0	C24—N30—H30	119.4
C15—C14—H14	120.0	C30—N30—H30	119.4
C16—C15—C14	120.10 (16)	N30—C30—C31	112.10 (12)
C16—C15—H15	120.0	N30—C30—H30A	109.2
C14—C15—H15	120.0	C31—C30—H30A	109.2
C15—C16—C17	120.34 (17)	N30—C30—H30B	109.2
C15—C16—H16	119.8	C31—C30—H30B	109.2
C17—C16—H16	119.8	H30A—C30—H30B	107.9
C16—C17—C12	120.20 (17)	O31—C31—O32	125.29 (13)
C16—C17—H17	119.9	O31—C31—C30	124.98 (13)
C12—C17—H17	119.9	O32—C31—C30	109.73 (12)
O18—C18—N20	122.73 (12)	C31—O32—C32	115.22 (13)
O18—C18—C10	118.15 (11)	O32—C32—H32A	109.5
N20—C18—C10	119.07 (11)	O32—C32—H32B	109.5
C18—N20—C20	118.75 (11)	H32A—C32—H32B	109.5
C18—N20—C23	128.88 (11)	O32—C32—H32C	109.5
C20—N20—C23	112.05 (10)	H32A—C32—H32C	109.5
N20—C20—C24	111.86 (11)	H32B—C32—H32C	109.5
N20—C20—C21	104.05 (10)	H1—O1—H2	105.56
C24—C20—C21	109.51 (11)
N10—C10—C11—C12	158.2 (1)	C23—N20—C20—C24	−122.61 (12)
C18—C10—C11—C12	−85.66 (14)	C18—N20—C20—C21	−178.58 (11)
C10—C11—C12—C17	−99.94 (15)	C23—N20—C20—C21	−4.49 (14)
C10—C11—C12—C13	80.71 (17)	C23—C22—C21—C20	34.16 (14)
C17—C12—C13—C14	0.4 (2)	N20—C20—C21—C22	−18.6 (1)
C11—C12—C13—C14	179.76 (13)	C24—C20—C21—C22	101.18 (12)
C12—C13—C14—C15	−0.8 (2)	C18—N20—C23—C22	−160.99 (13)
C13—C14—C15—C16	0.5 (3)	C20—N20—C23—C22	25.66 (14)
C14—C15—C16—C17	0.0 (3)	C21—C22—C23—N20	−36.02 (13)
C15—C16—C17—C12	−0.4 (3)	N20—C20—C24—O24	35.04 (17)
C13—C12—C17—C16	0.1 (2)	C21—C20—C24—O24	−79.78 (16)
C11—C12—C17—C16	−179.22 (14)	N20—C20—C24—N30	−147.2 (1)
N10—C10—C18—O18	34.80 (15)	C21—C20—C24—N30	98.00 (13)
C11—C10—C18—O18	−82.47 (14)	O24—C24—N30—C30	14.4 (2)
N10—C10—C18—N20	−147.7 (1)	C20—C24—N30—C30	−163.4 (1)
C11—C10—C18—N20	95.02 (14)	C24—N30—C30—C31	80.9 (2)
O18—C18—N20—C20	−1.09 (19)	N30—C30—C31—O31	−8.2 (2)
C10—C18—N20—C20	−178.5 (1)	N30—C30—C31—O32	172.0 (1)
O18—C18—N20—C23	−174.05 (12)	O31—C31—O32—C32	−3.0 (2)
C10—C18—N20—C23	8.58 (19)	C30—C31—O32—C32	176.89 (14)
C18—N20—C20—C24	63.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10A···O1	0.91	1.96	2.845 (2)	166
N10—H10C···Cl	0.91	2.31	3.112 (1)	147
N10—H10B···O18i	0.91	1.94	2.755 (1)	148
O1—H2···Clii	0.77	2.43	3.201 (1)	177
N30—H30···Cliii	0.88	2.43	3.299 (1)	171
O1—H1···Cliv	0.82	2.33	3.139 (1)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N10—H10A⋯O1	0.91	1.96	2.845 (2)	166
N10—H10C⋯Cl	0.91	2.31	3.112 (1)	147
N10—H10B⋯O18i	0.91	1.94	2.755 (1)	148
O1—H2⋯Clii	0.77	2.43	3.201 (1)	177
N30—H30⋯Cliii	0.88	2.43	3.299 (1)	171
O1—H1⋯Cliv	0.82	2.33	3.139 (1)	165

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .