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In the title compound, C20H22N204, the two phenyl rings form a dihedral angle of 89.2 (2)°. The crystal structure is stabilized by weak N—H...O and O—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806053955/ci2239sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806053955/ci2239Isup2.hkl
Contains datablock I

CCDC reference: 633652

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.035
  • wR factor = 0.088
  • Data-to-parameter ratio = 8.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C16 - C17 .. 7.05 su PLAT331_ALERT_2_B Small Average Phenyl C-C Dist. C13 -C18 1.36 Ang.
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C2 - C3 .. 6.06 su PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C1 -C6 1.36 Ang. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
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 26.35 From the CIF: _reflns_number_total 1978 Count of symmetry unique reflns 1986 Completeness (_total/calc) 99.60% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11 = . S
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

(DL)-2-[(DL)-2-Acetamido-3-phenylpropanamido]-3-phenylpropanoic acid top
Crystal data top
C20H22N2O4F(000) = 376
Mr = 354.40Dx = 1.292 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2129 reflections
a = 10.185 (3) Åθ = 2.7–24.4°
b = 8.633 (2) ŵ = 0.09 mm1
c = 10.427 (3) ÅT = 294 K
β = 96.364 (5)°Block, colourless
V = 911.1 (4) Å30.34 × 0.30 × 0.24 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer
1978 independent reflections
Radiation source: fine-focus sealed tube1573 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
φ and ω scansθmax = 26.4°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 1211
Tmin = 0.970, Tmax = 0.979k = 910
5164 measured reflectionsl = 1310
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0407P)2 + 0.0961P]
where P = (Fo2 + 2Fc2)/3
1978 reflections(Δ/σ)max = 0.002
237 parametersΔρmax = 0.12 e Å3
1 restraintΔρmin = 0.14 e Å3
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*/Ueq
O10.69996 (18)0.4395 (3)0.48036 (15)0.0562 (5)
O20.53139 (18)0.3649 (3)0.57981 (16)0.0559 (5)
H2A0.50570.32680.50940.084*
O30.57688 (18)0.7336 (2)0.62996 (16)0.0525 (5)
O40.4503 (2)0.9361 (2)0.98687 (16)0.0650 (6)
N10.6224 (2)0.5530 (2)0.77869 (17)0.0433 (5)
H10.61350.52330.85600.052*
N20.4033 (2)0.8729 (2)0.78138 (18)0.0448 (5)
H20.37740.90560.70480.054*
C10.9695 (3)0.2567 (4)0.6947 (3)0.0646 (9)
H1A1.01030.34290.73510.077*
C21.0398 (3)0.1607 (5)0.6216 (3)0.0769 (11)
H2B1.12760.18300.61270.092*
C30.9825 (4)0.0349 (5)0.5631 (3)0.0793 (11)
H31.03000.02850.51290.095*
C40.8559 (4)0.0017 (4)0.5779 (3)0.0800 (10)
H40.81630.08610.53910.096*
C50.7857 (3)0.0963 (4)0.6495 (3)0.0644 (8)
H50.69830.07210.65880.077*
C60.8408 (3)0.2257 (4)0.7079 (2)0.0505 (7)
C70.7611 (3)0.3296 (3)0.7824 (2)0.0530 (7)
H7A0.81430.36190.86070.064*
H7B0.68580.27270.80710.064*
C80.7124 (2)0.4724 (3)0.7061 (2)0.0426 (6)
H80.78780.53980.69560.051*
C90.6478 (2)0.4265 (3)0.5755 (2)0.0421 (6)
C100.5532 (3)0.6716 (3)0.7296 (2)0.0421 (6)
C110.4359 (3)0.7133 (3)0.7976 (2)0.0428 (6)
H110.45630.69140.88990.051*
C120.3218 (3)0.6105 (3)0.7428 (3)0.0548 (7)
H12A0.29820.63680.65270.066*
H12B0.35070.50340.74660.066*
C130.2029 (3)0.6255 (3)0.8121 (2)0.0495 (6)
C140.0979 (3)0.7094 (4)0.7607 (3)0.0638 (8)
H140.10090.75760.68130.077*
C150.0117 (4)0.7246 (5)0.8228 (4)0.0822 (10)
H150.08250.78330.78580.099*
C160.0182 (4)0.6563 (5)0.9359 (4)0.0860 (12)
H160.09320.66790.97830.103*
C170.0846 (4)0.5694 (5)0.9896 (3)0.0820 (12)
H170.07940.52051.06840.098*
C180.1966 (3)0.5535 (4)0.9279 (3)0.0665 (8)
H180.26720.49430.96480.080*
C190.4107 (2)0.9727 (3)0.8764 (2)0.0444 (6)
C200.3687 (4)1.1323 (4)0.8419 (3)0.0671 (9)
H20A0.27931.14740.86020.101*
H20B0.37411.14910.75160.101*
H20C0.42541.20440.89140.101*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0661 (11)0.0734 (13)0.0291 (8)0.0080 (11)0.0059 (8)0.0022 (9)
O20.0598 (12)0.0696 (14)0.0380 (9)0.0108 (11)0.0048 (9)0.0142 (10)
O30.0645 (11)0.0531 (11)0.0401 (10)0.0091 (10)0.0062 (8)0.0144 (9)
O40.1090 (17)0.0522 (12)0.0307 (9)0.0077 (12)0.0063 (10)0.0095 (9)
N10.0651 (14)0.0386 (12)0.0250 (9)0.0081 (11)0.0000 (9)0.0004 (9)
N20.0688 (14)0.0386 (12)0.0256 (9)0.0055 (11)0.0014 (9)0.0016 (9)
C10.068 (2)0.062 (2)0.0609 (18)0.0066 (16)0.0032 (16)0.0105 (15)
C20.066 (2)0.093 (3)0.073 (2)0.025 (2)0.0176 (17)0.026 (2)
C30.103 (3)0.073 (3)0.062 (2)0.034 (2)0.012 (2)0.0021 (19)
C40.106 (3)0.061 (2)0.071 (2)0.020 (2)0.003 (2)0.0123 (17)
C50.0706 (19)0.056 (2)0.0651 (19)0.0101 (16)0.0012 (15)0.0040 (16)
C60.0607 (17)0.0512 (16)0.0380 (13)0.0111 (14)0.0016 (12)0.0070 (13)
C70.0704 (18)0.0495 (17)0.0381 (13)0.0108 (14)0.0019 (13)0.0042 (12)
C80.0546 (14)0.0403 (15)0.0318 (12)0.0024 (12)0.0003 (11)0.0002 (11)
C90.0513 (15)0.0405 (14)0.0338 (12)0.0029 (12)0.0017 (11)0.0012 (11)
C100.0595 (15)0.0394 (14)0.0258 (11)0.0000 (11)0.0030 (10)0.0014 (10)
C110.0643 (16)0.0355 (13)0.0278 (11)0.0029 (12)0.0009 (11)0.0014 (11)
C120.0674 (18)0.0465 (16)0.0499 (15)0.0025 (14)0.0045 (13)0.0122 (13)
C130.0651 (17)0.0380 (14)0.0445 (14)0.0079 (13)0.0017 (12)0.0062 (12)
C140.076 (2)0.0571 (19)0.0582 (17)0.0012 (17)0.0068 (16)0.0065 (16)
C150.077 (2)0.080 (2)0.089 (3)0.007 (2)0.007 (2)0.016 (2)
C160.080 (2)0.090 (3)0.092 (3)0.015 (2)0.028 (2)0.032 (3)
C170.123 (3)0.073 (2)0.0540 (18)0.039 (3)0.027 (2)0.0105 (18)
C180.091 (2)0.0542 (18)0.0532 (17)0.0117 (18)0.0034 (16)0.0015 (16)
C190.0562 (15)0.0412 (15)0.0355 (14)0.0010 (12)0.0032 (11)0.0060 (11)
C200.094 (2)0.0456 (17)0.0598 (18)0.0121 (17)0.0005 (17)0.0085 (15)
Geometric parameters (Å, º) top
O1—C91.181 (3)C7—H7B0.97
O2—C91.305 (3)C8—C91.498 (3)
O2—H2A0.82C8—H80.98
O3—C101.216 (3)C10—C111.499 (4)
O4—C191.220 (3)C11—C121.523 (4)
N1—C101.314 (3)C11—H110.98
N1—C81.432 (3)C12—C131.483 (4)
N1—H10.86C12—H12A0.97
N2—C191.308 (3)C12—H12B0.97
N2—C111.423 (3)C13—C141.352 (4)
N2—H20.86C13—C181.366 (4)
C1—C61.360 (4)C14—C151.357 (5)
C1—C21.379 (5)C14—H140.93
C1—H1A0.93C15—C161.327 (6)
C2—C31.346 (6)C15—H150.93
C2—H2B0.93C16—C171.357 (5)
C3—C41.346 (5)C16—H160.93
C3—H30.93C17—C181.377 (5)
C4—C51.362 (5)C17—H170.93
C4—H40.93C18—H180.93
C5—C61.363 (4)C19—C201.475 (4)
C5—H50.93C20—H20A0.96
C6—C71.485 (4)C20—H20B0.96
C7—C81.520 (4)C20—H20C0.96
C7—H7A0.97
C9—O2—H2A109.5O3—C10—C11122.8 (2)
C10—N1—C8121.3 (2)N1—C10—C11115.1 (2)
C10—N1—H1119.3N2—C11—C10111.3 (2)
C8—N1—H1119.3N2—C11—C12111.2 (2)
C19—N2—C11123.7 (2)C10—C11—C12107.3 (2)
C19—N2—H2118.2N2—C11—H11109.0
C11—N2—H2118.2C10—C11—H11109.0
C6—C1—C2120.2 (3)C12—C11—H11109.0
C6—C1—H1A119.9C13—C12—C11113.4 (2)
C2—C1—H1A119.9C13—C12—H12A108.9
C3—C2—C1120.7 (3)C11—C12—H12A108.9
C3—C2—H2B119.7C13—C12—H12B108.9
C1—C2—H2B119.7C11—C12—H12B108.9
C2—C3—C4119.5 (3)H12A—C12—H12B107.7
C2—C3—H3120.3C14—C13—C18118.8 (3)
C4—C3—H3120.3C14—C13—C12120.4 (3)
C3—C4—C5120.2 (4)C18—C13—C12120.8 (3)
C3—C4—H4119.9C13—C14—C15121.3 (3)
C5—C4—H4119.9C13—C14—H14119.4
C4—C5—C6121.4 (3)C15—C14—H14119.4
C4—C5—H5119.3C16—C15—C14120.4 (4)
C6—C5—H5119.3C16—C15—H15119.8
C1—C6—C5118.0 (3)C14—C15—H15119.8
C1—C6—C7121.5 (3)C15—C16—C17120.0 (4)
C5—C6—C7120.5 (3)C15—C16—H16120.0
C6—C7—C8112.5 (2)C17—C16—H16120.0
C6—C7—H7A109.1C16—C17—C18120.2 (4)
C8—C7—H7A109.1C16—C17—H17119.9
C6—C7—H7B109.1C18—C17—H17119.9
C8—C7—H7B109.1C13—C18—C17119.4 (3)
H7A—C7—H7B107.8C13—C18—H18120.3
N1—C8—C9111.5 (2)C17—C18—H18120.3
N1—C8—C7108.02 (19)O4—C19—N2122.0 (2)
C9—C8—C7110.2 (2)O4—C19—C20121.9 (2)
N1—C8—H8109.0N2—C19—C20116.1 (2)
C9—C8—H8109.0C19—C20—H20A109.5
C7—C8—H8109.0C19—C20—H20B109.5
O1—C9—O2124.2 (2)H20A—C20—H20B109.5
O1—C9—C8123.1 (2)C19—C20—H20C109.5
O2—C9—C8112.7 (2)H20A—C20—H20C109.5
O3—C10—N1121.8 (2)H20B—C20—H20C109.5
C6—C1—C2—C30.4 (5)C19—N2—C11—C10115.5 (3)
C1—C2—C3—C41.0 (5)C19—N2—C11—C12125.0 (3)
C2—C3—C4—C51.2 (5)O3—C10—C11—N232.5 (3)
C3—C4—C5—C60.1 (5)N1—C10—C11—N2153.4 (2)
C2—C1—C6—C51.4 (4)O3—C10—C11—C1289.3 (3)
C2—C1—C6—C7177.9 (3)N1—C10—C11—C1284.8 (3)
C4—C5—C6—C11.2 (4)N2—C11—C12—C1365.0 (3)
C4—C5—C6—C7178.2 (3)C10—C11—C12—C13173.1 (2)
C1—C6—C7—C879.0 (3)C11—C12—C13—C14102.6 (3)
C5—C6—C7—C8100.3 (3)C11—C12—C13—C1878.2 (3)
C10—N1—C8—C950.9 (3)C18—C13—C14—C150.9 (5)
C10—N1—C8—C7172.1 (2)C12—C13—C14—C15179.9 (3)
C6—C7—C8—N1172.1 (2)C13—C14—C15—C160.3 (6)
C6—C7—C8—C950.0 (3)C14—C15—C16—C170.6 (6)
N1—C8—C9—O1137.0 (3)C15—C16—C17—C180.8 (6)
C7—C8—C9—O1103.0 (3)C14—C13—C18—C170.6 (5)
N1—C8—C9—O245.8 (3)C12—C13—C18—C17179.8 (3)
C7—C8—C9—O274.2 (3)C16—C17—C18—C130.2 (5)
C8—N1—C10—O312.0 (4)C11—N2—C19—O42.2 (4)
C8—N1—C10—C11162.2 (2)C11—N2—C19—C20178.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O3i0.821.792.598 (2)169
N1—H1···O4ii0.861.982.819 (3)166
N2—H2···O1iii0.862.022.872 (3)168
Symmetry codes: (i) x+1, y1/2, z+1; (ii) x+1, y1/2, z+2; (iii) x+1, y+1/2, z+1.
 

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