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The title compound, C24H29NO5, the benzyl ester of the Phe–Gly dipeptidomimetic containing a keto­methyl­ene motif, was synthesized from the readily available α,β-unsaturated γ-ketoester. The methyl­ene group in the benzyl part of the mol­ecule is disordered. There is an intermolecular N—H...O hydrogen bond linking the mol­ecules in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805010895/er6008sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805010895/er6008Isup2.hkl
Contains datablock I

CCDC reference: 271867

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.035
  • wR factor = 0.099
  • Data-to-parameter ratio = 10.1

checkCIF/PLATON results

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Alert level A PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.21 Ratio
Author Response: see _publ_section_exptl_refinement

Alert level B PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.99 Deg.
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT128_ALERT_4_C Non-standard setting of Space group P21/c .... P21/a PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O5 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C19 PLAT301_ALERT_3_C Main Residue Disorder ......................... 3.00 Perc. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C19 - C20 ... 1.38 Ang. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C19 - C24 ... 1.37 Ang. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 23.50 Deg. C182 -O5 -C181 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 22.90 Deg. C181 -C19 -C182 1.555 1.555 1.555 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C24 H29 N O5
1 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4-PC Software (Enraf-Nonius, 1992); cell refinement: CELDIM in CAD-4-PC Software; data reduction: XCAD (McArdle & Higgins, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: OSCAIL (Version 9; McArdle, 1993).

(I) top
Crystal data top
C24H29NO5F(000) = 880
Mr = 411.48Dx = 1.222 Mg m3
Monoclinic, P21/aMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yabCell parameters from 25 reflections
a = 9.6080 (19) Åθ = 12–20°
b = 22.856 (4) ŵ = 0.09 mm1
c = 10.2908 (17) ÅT = 298 K
β = 98.353 (16)°Block, colourless
V = 2235.9 (7) Å30.40 × 0.20 × 0.10 mm
Z = 4
Data collection top
Enraf-Nonius CAD4
diffractometer
1759 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.010
Graphite monochromatorθmax = 25.0°, θmin = 1.8°
ω–2θ scansh = 011
Absorption correction: ψ scan
(ABSCALC in OSCAIL; McArdle & Daly, 1999; North et al, 1968)
k = 027
Tmin = 0.967, Tmax = 0.992l = 1212
4262 measured reflections3 standard reflections every 120 min
3941 independent reflections intensity decay: 2%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.099 w = 1/[σ2(Fo2) + (0.0484P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.91(Δ/σ)max = 0.001
3941 reflectionsΔρmax = 0.15 e Å3
389 parametersΔρmin = 0.14 e Å3
66 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0041 (8)
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
xyzUiso*/UeqOcc. (<1)
C1811.5779 (10)0.3446 (5)0.3571 (12)0.080 (4)0.50
H18A1.58840.34610.26480.104*0.50
H18B1.51720.31190.37070.104*0.50
C1821.6109 (11)0.3631 (6)0.3325 (12)0.089 (5)0.50
H18C1.65650.38590.27130.116*0.50
H18D1.55770.33180.28460.116*0.50
O10.70516 (14)0.54106 (6)0.08083 (12)0.0509 (4)
N10.86413 (17)0.47118 (7)0.10717 (18)0.0466 (5)
O31.14442 (15)0.50649 (7)0.19428 (14)0.0596 (4)
O20.79986 (15)0.51283 (6)0.28717 (14)0.0595 (4)
O51.51713 (17)0.40063 (9)0.39874 (19)0.0963 (6)
O41.31815 (19)0.36080 (9)0.3081 (2)0.0983 (6)
H222.057 (3)0.2990 (12)0.659 (3)0.105 (10)*
H120.733 (3)0.2353 (13)0.148 (3)0.118 (11)*
H110.623 (3)0.2373 (12)0.076 (3)0.097 (10)*
H10.8611 (17)0.4734 (7)0.0249 (17)0.028 (5)*
H60.9239 (16)0.4157 (7)0.2501 (16)0.024 (4)*
H1621.345 (2)0.4881 (9)0.377 (2)0.070 (7)*
H4B0.726 (3)0.6136 (11)0.301 (3)0.091 (8)*
H2C0.540 (2)0.5330 (10)0.273 (2)0.078 (8)*
H721.049 (2)0.4062 (8)0.024 (2)0.053 (6)*
H711.094 (2)0.3660 (9)0.1499 (19)0.060 (6)*
H1521.1168 (19)0.4121 (9)0.4020 (18)0.044 (6)*
H3A0.470 (2)0.6372 (11)0.002 (2)0.081 (8)*
H1611.336 (2)0.4533 (8)0.516 (2)0.063 (6)*
H1511.111 (2)0.4769 (9)0.445 (2)0.066 (7)*
H4A0.630 (3)0.6597 (12)0.215 (2)0.082 (9)*
H130.906 (2)0.3002 (10)0.215 (2)0.070 (8)*
H90.871 (2)0.3683 (9)0.1407 (19)0.050 (6)*
H4C0.760 (3)0.6463 (12)0.171 (3)0.098 (10)*
H231.986 (3)0.4001 (12)0.632 (3)0.108 (10)*
H3B0.607 (3)0.6268 (10)0.052 (2)0.078 (9)*
H211.907 (3)0.2254 (14)0.555 (3)0.121 (11)*
H100.693 (3)0.3053 (10)0.222 (2)0.085 (8)*
H2A0.452 (3)0.5240 (11)0.131 (2)0.083 (9)*
H201.705 (3)0.2501 (11)0.428 (2)0.084 (9)*
H2B0.433 (3)0.5790 (11)0.211 (2)0.089 (9)*
H241.790 (2)0.4184 (11)0.492 (2)0.078 (8)*
H3C0.494 (3)0.5756 (13)0.065 (3)0.125 (12)*
C10.6052 (2)0.58389 (9)0.1218 (2)0.0483 (5)
C20.4974 (3)0.55232 (14)0.1892 (3)0.0657 (7)
C30.5390 (4)0.60845 (15)0.0087 (3)0.0733 (8)
C40.6830 (4)0.62989 (13)0.2078 (3)0.0730 (8)
C50.7894 (2)0.50919 (9)0.1688 (2)0.0428 (5)
C60.9665 (2)0.43367 (9)0.1832 (2)0.0422 (5)
C71.0166 (2)0.38596 (10)0.0964 (3)0.0516 (6)
C80.9040 (2)0.34231 (9)0.0461 (2)0.0473 (5)
C90.8418 (3)0.34267 (11)0.0827 (3)0.0585 (6)
C100.7380 (3)0.30259 (12)0.1292 (3)0.0710 (8)
C110.6948 (3)0.26261 (13)0.0451 (4)0.0809 (9)
C120.7550 (3)0.26139 (12)0.0829 (4)0.0822 (9)
C130.8598 (3)0.30065 (11)0.1281 (3)0.0667 (7)
C141.0931 (2)0.46717 (9)0.24977 (19)0.0428 (5)
C151.1519 (2)0.44932 (12)0.3875 (2)0.0493 (6)
C161.3109 (2)0.45203 (11)0.4194 (3)0.0546 (6)
C171.3795 (2)0.39975 (11)0.3696 (2)0.0582 (6)
C191.7203 (2)0.33790 (13)0.4415 (2)0.0636 (7)
C201.7576 (3)0.27986 (15)0.4633 (3)0.0806 (9)
C211.8819 (4)0.26540 (15)0.5432 (3)0.0884 (9)
C221.9653 (4)0.30806 (16)0.6028 (3)0.0840 (9)
C231.9293 (3)0.36500 (14)0.5851 (3)0.0711 (7)
C241.8070 (3)0.37957 (14)0.5049 (2)0.0665 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1810.056 (6)0.112 (7)0.072 (5)0.031 (6)0.009 (4)0.019 (5)
C1820.038 (4)0.136 (10)0.091 (7)0.016 (5)0.002 (4)0.030 (6)
O10.0488 (8)0.0598 (9)0.0434 (8)0.0192 (7)0.0041 (7)0.0046 (7)
N10.0463 (11)0.0585 (11)0.0348 (10)0.0127 (9)0.0053 (8)0.0000 (9)
O30.0568 (9)0.0617 (10)0.0590 (9)0.0087 (8)0.0039 (7)0.0130 (8)
O20.0664 (10)0.0713 (10)0.0398 (9)0.0204 (8)0.0047 (7)0.0004 (7)
O50.0468 (11)0.1281 (17)0.1068 (14)0.0252 (11)0.0131 (10)0.0358 (12)
O40.0694 (13)0.0965 (14)0.1239 (16)0.0118 (12)0.0030 (11)0.0348 (13)
C10.0436 (13)0.0485 (13)0.0529 (13)0.0130 (11)0.0073 (10)0.0007 (11)
C20.0483 (16)0.076 (2)0.0733 (19)0.0060 (15)0.0111 (14)0.0040 (17)
C30.074 (2)0.080 (2)0.0661 (18)0.0353 (18)0.0106 (16)0.0137 (16)
C40.080 (2)0.0518 (18)0.086 (2)0.0025 (17)0.0084 (18)0.0065 (16)
C50.0387 (11)0.0458 (12)0.0434 (13)0.0023 (10)0.0042 (10)0.0001 (11)
C60.0368 (11)0.0454 (12)0.0449 (12)0.0051 (10)0.0069 (10)0.0058 (11)
C70.0474 (14)0.0510 (14)0.0584 (14)0.0077 (12)0.0141 (12)0.0001 (12)
C80.0471 (13)0.0400 (12)0.0571 (14)0.0090 (10)0.0158 (11)0.0039 (11)
C90.0639 (16)0.0533 (15)0.0610 (17)0.0012 (13)0.0182 (14)0.0002 (13)
C100.0688 (18)0.0699 (18)0.074 (2)0.0040 (15)0.0097 (16)0.0249 (16)
C110.070 (2)0.0571 (19)0.119 (3)0.0116 (15)0.0274 (19)0.0331 (19)
C120.103 (2)0.0527 (18)0.097 (3)0.0124 (17)0.035 (2)0.0002 (17)
C130.084 (2)0.0529 (16)0.0650 (18)0.0045 (15)0.0154 (15)0.0041 (14)
C140.0413 (12)0.0449 (13)0.0441 (12)0.0079 (10)0.0122 (10)0.0030 (10)
C150.0428 (13)0.0603 (15)0.0456 (13)0.0005 (12)0.0088 (10)0.0023 (12)
C160.0477 (14)0.0659 (17)0.0480 (15)0.0054 (12)0.0002 (11)0.0032 (13)
C170.0474 (15)0.0786 (18)0.0458 (13)0.0052 (13)0.0022 (11)0.0011 (13)
C190.0481 (14)0.085 (2)0.0583 (15)0.0110 (14)0.0098 (12)0.0119 (14)
C200.080 (2)0.082 (2)0.085 (2)0.0168 (19)0.0254 (17)0.0169 (18)
C210.106 (3)0.073 (2)0.084 (2)0.022 (2)0.0057 (19)0.0135 (17)
C220.078 (2)0.103 (3)0.0664 (19)0.018 (2)0.0026 (16)0.0016 (18)
C230.0619 (17)0.085 (2)0.0664 (17)0.0035 (17)0.0103 (14)0.0022 (16)
C240.0689 (18)0.0659 (19)0.0648 (16)0.0084 (16)0.0099 (14)0.0036 (15)
Geometric parameters (Å, º) top
C181—O51.496 (10)C7—C81.507 (3)
C181—C191.519 (10)C7—H720.97 (2)
C181—H18A0.9700C7—H710.98 (2)
C181—H18B0.9700C8—C91.372 (3)
C182—O51.481 (10)C8—C131.380 (3)
C182—C191.534 (11)C9—C101.388 (3)
C182—H18C0.9700C9—H90.91 (2)
C182—H18D0.9700C10—C111.364 (4)
O1—C51.338 (2)C10—H100.99 (2)
O1—C11.475 (2)C11—C121.359 (4)
N1—C51.343 (2)C11—H110.92 (3)
N1—C61.446 (3)C12—C131.378 (4)
N1—H10.844 (17)C12—H120.94 (3)
O3—C141.208 (2)C13—H130.94 (2)
O2—C51.211 (2)C14—C151.504 (3)
O5—C171.313 (3)C15—C161.516 (3)
O4—C171.197 (3)C15—H1520.935 (19)
C1—C41.502 (3)C15—H1510.98 (2)
C1—C31.508 (3)C16—C171.491 (3)
C1—C21.511 (3)C16—H1621.01 (2)
C2—H2C1.00 (2)C16—H1610.99 (2)
C2—H2A0.95 (2)C19—C241.367 (3)
C2—H2B0.92 (3)C19—C201.384 (4)
C3—H3A0.95 (2)C20—C211.388 (4)
C3—H3B0.94 (2)C20—H200.89 (3)
C3—H3C1.01 (3)C21—C221.351 (4)
C4—H4B1.05 (3)C21—H210.95 (3)
C4—H4A0.86 (3)C22—C231.352 (4)
C4—H4C0.96 (3)C22—H221.01 (3)
C6—C141.514 (3)C23—C241.375 (3)
C6—C71.531 (3)C23—H231.05 (3)
C6—H60.945 (16)C24—H240.91 (2)
O5—C181—C19106.2 (7)C9—C8—C13117.7 (2)
O5—C181—H18A110.5C9—C8—C7121.2 (2)
C19—C181—H18A110.5C13—C8—C7121.1 (2)
O5—C181—H18B110.5C8—C9—C10121.3 (3)
C19—C181—H18B110.5C8—C9—H9120.5 (12)
H18A—C181—H18B108.7C10—C9—H9118.1 (12)
O5—C182—C19106.2 (8)C11—C10—C9119.5 (3)
O5—C182—H18C110.5C11—C10—H10121.8 (14)
C19—C182—H18C110.5C9—C10—H10118.6 (14)
O5—C182—H18D110.5C12—C11—C10120.2 (3)
C19—C182—H18D110.5C12—C11—H11120.7 (17)
H18C—C182—H18D108.7C10—C11—H11119.1 (17)
C5—O1—C1121.51 (15)C11—C12—C13120.1 (3)
C5—N1—C6119.75 (18)C11—C12—H12126.5 (18)
C5—N1—H1119.5 (12)C13—C12—H12113.4 (18)
C6—N1—H1120.0 (11)C12—C13—C8121.1 (3)
C17—O5—C182123.1 (5)C12—C13—H13122.5 (14)
C17—O5—C181110.1 (5)C8—C13—H13116.3 (14)
C182—O5—C18123.5 (9)O3—C14—C15121.60 (19)
O1—C1—C4110.1 (2)O3—C14—C6121.25 (18)
O1—C1—C3101.55 (18)C15—C14—C6117.15 (19)
C4—C1—C3111.9 (2)C14—C15—C16114.96 (19)
O1—C1—C2109.41 (19)C14—C15—H152107.6 (12)
C4—C1—C2112.3 (2)C16—C15—H152112.2 (12)
C3—C1—C2111.0 (2)C14—C15—H151105.4 (12)
C1—C2—H2C112.6 (13)C16—C15—H151108.6 (12)
C1—C2—H2A108.7 (15)H152—C15—H151107.7 (17)
H2C—C2—H2A110 (2)C17—C16—C15112.0 (2)
C1—C2—H2B109.2 (16)C17—C16—H162108.5 (12)
H2C—C2—H2B107 (2)C15—C16—H162108.8 (13)
H2A—C2—H2B110 (2)C17—C16—H161108.3 (12)
C1—C3—H3A111.4 (14)C15—C16—H161107.9 (12)
C1—C3—H3B110.9 (15)H162—C16—H161111.4 (18)
H3A—C3—H3B107 (2)O4—C17—O5122.3 (2)
C1—C3—H3C109.1 (17)O4—C17—C16124.7 (2)
H3A—C3—H3C110 (2)O5—C17—C16113.0 (2)
H3B—C3—H3C109 (2)C24—C19—C20117.8 (3)
C1—C4—H4B112.5 (14)C24—C19—C181129.7 (5)
C1—C4—H4A110.7 (17)C20—C19—C181112.3 (5)
H4B—C4—H4A111 (2)C24—C19—C182113.2 (6)
C1—C4—H4C113.1 (17)C20—C19—C182127.7 (6)
H4B—C4—H4C106 (2)C181—C19—C18222.9 (9)
H4A—C4—H4C103 (2)C19—C20—C21120.3 (3)
O2—C5—O1126.65 (18)C19—C20—H20123.2 (17)
O2—C5—N1123.17 (19)C21—C20—H20116.5 (17)
O1—C5—N1110.19 (18)C22—C21—C20120.0 (3)
N1—C6—C14112.55 (16)C22—C21—H21121 (2)
N1—C6—C7110.67 (18)C20—C21—H21119 (2)
C14—C6—C7108.91 (16)C21—C22—C23120.7 (3)
N1—C6—H6108.6 (9)C21—C22—H22121.7 (16)
C14—C6—H6107.2 (9)C23—C22—H22117.6 (16)
C7—C6—H6108.8 (9)C22—C23—C24119.6 (3)
C8—C7—C6113.67 (17)C22—C23—H23124.8 (15)
C8—C7—H72110.2 (12)C24—C23—H23115.6 (15)
C6—C7—H72106.0 (12)C19—C24—C23121.7 (3)
C8—C7—H71109.8 (12)C19—C24—H24121.7 (16)
C6—C7—H71106.5 (12)C23—C24—H24116.4 (16)
H72—C7—H71110.6 (17)
C19—C182—O5—C17135.1 (5)N1—C6—C14—C15139.93 (19)
C19—C182—O5—C18173.3 (19)C7—C6—C14—C1597.0 (2)
C19—C181—O5—C17156.6 (6)O3—C14—C15—C1637.0 (3)
C19—C181—O5—C18275.3 (19)C6—C14—C15—C16143.0 (2)
C5—O1—C1—C460.2 (3)C14—C15—C16—C1780.4 (3)
C5—O1—C1—C3179.0 (2)C182—O5—C17—O415.9 (7)
C5—O1—C1—C263.7 (2)C181—O5—C17—O46.0 (6)
C1—O1—C5—O23.8 (3)C182—O5—C17—C16163.3 (6)
C1—O1—C5—N1176.37 (16)C181—O5—C17—C16174.7 (6)
C6—N1—C5—O22.3 (3)C15—C16—C17—O42.2 (3)
C6—N1—C5—O1177.61 (17)C15—C16—C17—O5178.6 (2)
C5—N1—C6—C1469.5 (2)O5—C181—C19—C2423.8 (11)
C5—N1—C6—C7168.39 (18)O5—C181—C19—C20150.2 (6)
N1—C6—C7—C867.1 (3)O5—C181—C19—C18273 (2)
C14—C6—C7—C8168.64 (19)O5—C182—C19—C2465.6 (8)
C6—C7—C8—C9106.5 (2)O5—C182—C19—C20128.3 (6)
C6—C7—C8—C1373.5 (3)O5—C182—C19—C18175.1 (18)
C13—C8—C9—C100.0 (3)C24—C19—C20—C212.4 (4)
C7—C8—C9—C10179.9 (2)C181—C19—C20—C21177.2 (6)
C8—C9—C10—C111.2 (4)C182—C19—C20—C21163.1 (6)
C9—C10—C11—C121.2 (4)C19—C20—C21—C221.7 (4)
C10—C11—C12—C130.1 (4)C20—C21—C22—C230.2 (5)
C11—C12—C13—C81.1 (4)C21—C22—C23—C240.5 (4)
C9—C8—C13—C121.1 (3)C20—C19—C24—C231.7 (4)
C7—C8—C13—C12178.8 (2)C181—C19—C24—C23175.5 (6)
N1—C6—C14—O340.1 (3)C182—C19—C24—C23165.8 (5)
C7—C6—C14—O383.0 (2)C22—C23—C24—C190.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.84 (2)2.295 (17)3.133 (1)172 (2)
Symmetry code: (i) x+2, y+1, z.
 

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