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Colorless crystals of the title compound, C16H17NO2, have been obtained by the reaction of benzoyl chloride and (S)-2-amino-3-phenyl­propan-1-ol. The crystal packing is stabilized by O—H...O and N—H...O inter­molecular hydrogen-bonding inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680503477X/rz6129sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680503477X/rz6129Isup2.hkl
Contains datablock I

CCDC reference: 289879

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.034
  • wR factor = 0.089
  • Data-to-parameter ratio = 7.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.48 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C5 -C10 1.37 Ang. PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C11 -C16 1.37 Ang.
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 25.00 From the CIF: _reflns_number_total 1286 Count of symmetry unique reflns 1293 Completeness (_total/calc) 99.46% 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
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and ViewerPro (Accelrys, 2001); software used to prepare material for publication: SHELXL97.

(S)—N-(1-Benzyl-2-hydroxyethyl)benzamide top
Crystal data top
C16H17NO2F(000) = 272
Mr = 255.31Dx = 1.297 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: p 2ybCell parameters from 2983 reflections
a = 8.082 (3) Åθ = 2.6–28.1°
b = 5.0983 (16) ŵ = 0.09 mm1
c = 16.034 (5) ÅT = 273 K
β = 98.424 (5)°Irregular fragment, colorless
V = 653.5 (4) Å30.20 × 0.15 × 0.10 mm
Z = 2
Data collection top
Bruker APEX area-detector
diffractometer
1286 independent reflections
Radiation source: fine-focus sealed tube1243 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
φ and ω scansθmax = 25.0°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 99
Tmin = 0.983, Tmax = 0.992k = 66
4641 measured reflectionsl = 1918
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089All H-atom parameters refined
S = 1.07 w = 1/[σ2(Fo2) + (0.0534P)2 + 0.0567P]
where P = (Fo2 + 2Fc2)/3
1286 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 0.15 e Å3
1 restraintΔρmin = 0.15 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
N10.3162 (2)0.8638 (3)0.25623 (10)0.0363 (4)
H1D0.32100.71430.23190.044*
O10.5104 (2)0.7209 (3)0.47135 (9)0.0582 (5)
H1C0.50540.87120.48900.087*
C90.2092 (3)1.0082 (6)0.23908 (16)0.0609 (7)
H9A0.27080.97410.18650.073*
C80.2560 (3)1.2081 (6)0.28713 (17)0.0606 (7)
H8A0.34811.31160.26730.073*
C140.2384 (3)0.9824 (5)0.05569 (14)0.0524 (6)
H14A0.22450.96470.11400.063*
C70.1668 (3)1.2544 (6)0.36432 (17)0.0597 (7)
H7A0.19881.38850.39790.072*
C60.0312 (3)1.1051 (6)0.39251 (15)0.0532 (6)
H6A0.02891.13940.44540.064*
C50.0197 (3)0.9046 (5)0.34492 (13)0.0446 (5)
C150.3353 (3)0.8076 (5)0.00601 (14)0.0503 (6)
H15A0.38860.67260.03070.060*
C130.1624 (3)1.1815 (5)0.02042 (14)0.0520 (6)
H13A0.09611.30000.05450.062*
C10.1734 (3)0.7515 (5)0.37435 (13)0.0468 (6)
H1A0.15860.57370.35300.056*
H1B0.18920.74280.43540.056*
C100.0732 (3)0.8585 (6)0.26740 (14)0.0533 (6)
H10A0.04270.72310.23390.064*
C160.3545 (3)0.8295 (5)0.07955 (13)0.0418 (5)
H16A0.41860.70750.11320.050*
C110.2787 (2)1.0333 (4)0.11608 (12)0.0340 (4)
C120.1829 (3)1.2084 (5)0.06504 (13)0.0435 (5)
H12A0.13141.34680.08900.052*
C30.4843 (3)0.7233 (5)0.38291 (13)0.0441 (5)
H3A0.47720.54400.36250.053*
H3B0.57980.80500.36310.053*
O20.2971 (2)1.2973 (3)0.23677 (9)0.0501 (5)
C20.3283 (3)0.8676 (4)0.34635 (11)0.0382 (5)
H2A0.33861.05030.36540.046*
C40.2982 (2)1.0764 (4)0.20817 (12)0.0343 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0562 (10)0.0215 (8)0.0307 (8)0.0010 (8)0.0050 (7)0.0013 (7)
O10.0961 (12)0.0390 (10)0.0345 (8)0.0057 (9)0.0075 (8)0.0028 (7)
C90.0608 (15)0.072 (2)0.0481 (13)0.0070 (14)0.0010 (11)0.0024 (13)
C80.0548 (13)0.0602 (17)0.0672 (16)0.0048 (13)0.0103 (12)0.0115 (14)
C140.0710 (15)0.0544 (15)0.0304 (10)0.0076 (13)0.0026 (10)0.0003 (11)
C70.0625 (14)0.0534 (17)0.0656 (15)0.0073 (13)0.0176 (12)0.0046 (13)
C60.0609 (13)0.0553 (16)0.0437 (12)0.0008 (13)0.0081 (10)0.0041 (12)
C50.0564 (12)0.0412 (13)0.0385 (10)0.0024 (11)0.0142 (9)0.0022 (10)
C150.0671 (14)0.0434 (13)0.0420 (11)0.0028 (12)0.0129 (10)0.0052 (11)
C130.0642 (14)0.0452 (13)0.0423 (12)0.0021 (12)0.0067 (10)0.0077 (11)
C10.0650 (14)0.0404 (13)0.0364 (11)0.0018 (11)0.0120 (10)0.0053 (9)
C100.0642 (14)0.0517 (15)0.0451 (13)0.0036 (13)0.0114 (10)0.0060 (12)
C160.0509 (11)0.0368 (12)0.0368 (10)0.0030 (10)0.0039 (8)0.0012 (9)
C110.0400 (10)0.0270 (11)0.0343 (10)0.0050 (8)0.0033 (8)0.0014 (8)
C120.0527 (12)0.0344 (12)0.0418 (11)0.0037 (10)0.0008 (9)0.0013 (10)
C30.0627 (12)0.0345 (13)0.0335 (10)0.0016 (11)0.0022 (9)0.0019 (9)
O20.0859 (12)0.0248 (8)0.0381 (8)0.0006 (8)0.0036 (7)0.0006 (7)
C20.0583 (12)0.0257 (10)0.0304 (9)0.0012 (10)0.0055 (8)0.0014 (9)
C40.0404 (10)0.0246 (10)0.0368 (10)0.0005 (8)0.0015 (8)0.0004 (9)
Geometric parameters (Å, º) top
N1—C41.325 (3)C15—C161.362 (3)
N1—C21.434 (2)C15—H15A0.9300
N1—H1D0.8600C13—C121.363 (3)
O1—C31.403 (2)C13—H13A0.9300
O1—H1C0.8200C1—C21.511 (3)
C9—C101.361 (4)C1—H1A0.9700
C9—C81.364 (4)C1—H1B0.9700
C9—H9A0.9300C10—H10A0.9300
C8—C71.358 (4)C16—C111.380 (3)
C8—H8A0.9300C16—H16A0.9300
C14—C131.352 (4)C11—C121.371 (3)
C14—C151.364 (4)C11—C41.478 (3)
C14—H14A0.9300C12—H12A0.9300
C7—C61.356 (4)C3—C21.502 (3)
C7—H7A0.9300C3—H3A0.9700
C6—C51.374 (4)C3—H3B0.9700
C6—H6A0.9300O2—C41.217 (3)
C5—C101.375 (3)C2—H2A0.9800
C5—C11.484 (3)
C4—N1—C2124.10 (17)C5—C1—H1B109.0
C4—N1—H1D118.0C2—C1—H1B109.0
C2—N1—H1D118.0H1A—C1—H1B107.8
C3—O1—H1C109.5C9—C10—C5120.9 (3)
C10—C9—C8120.5 (2)C9—C10—H10A119.6
C10—C9—H9A119.7C5—C10—H10A119.6
C8—C9—H9A119.7C15—C16—C11119.8 (2)
C7—C8—C9119.4 (3)C15—C16—H16A120.1
C7—C8—H8A120.3C11—C16—H16A120.1
C9—C8—H8A120.3C12—C11—C16118.95 (19)
C13—C14—C15120.2 (2)C12—C11—C4117.89 (19)
C13—C14—H14A119.9C16—C11—C4123.15 (18)
C15—C14—H14A119.9C13—C12—C11120.6 (2)
C6—C7—C8120.1 (3)C13—C12—H12A119.7
C6—C7—H7A120.0C11—C12—H12A119.7
C8—C7—H7A120.0O1—C3—C2113.08 (18)
C7—C6—C5121.7 (2)O1—C3—H3A109.0
C7—C6—H6A119.2C2—C3—H3A109.0
C5—C6—H6A119.2O1—C3—H3B109.0
C6—C5—C10117.4 (2)C2—C3—H3B109.0
C6—C5—C1121.3 (2)H3A—C3—H3B107.8
C10—C5—C1121.2 (2)N1—C2—C3108.42 (16)
C16—C15—C14120.3 (2)N1—C2—C1110.92 (16)
C16—C15—H15A119.8C3—C2—C1112.14 (18)
C14—C15—H15A119.8N1—C2—H2A108.4
C14—C13—C12120.0 (2)C3—C2—H2A108.4
C14—C13—H13A120.0C1—C2—H2A108.4
C12—C13—H13A120.0O2—C4—N1122.96 (18)
C5—C1—C2113.00 (18)O2—C4—C11120.55 (18)
C5—C1—H1A109.0N1—C4—C11116.49 (17)
C2—C1—H1A109.0
C10—C9—C8—C70.9 (4)C14—C13—C12—C110.8 (3)
C9—C8—C7—C60.9 (4)C16—C11—C12—C130.2 (3)
C8—C7—C6—C50.2 (4)C4—C11—C12—C13179.0 (2)
C7—C6—C5—C100.6 (4)C4—N1—C2—C3126.2 (2)
C7—C6—C5—C1176.7 (2)C4—N1—C2—C1110.2 (2)
C13—C14—C15—C161.0 (4)O1—C3—C2—N1178.52 (18)
C15—C14—C13—C120.2 (4)O1—C3—C2—C158.7 (2)
C6—C5—C1—C289.9 (3)C5—C1—C2—N163.5 (2)
C10—C5—C1—C287.3 (3)C5—C1—C2—C3175.08 (18)
C8—C9—C10—C50.1 (4)C2—N1—C4—O23.1 (3)
C6—C5—C10—C90.6 (4)C2—N1—C4—C11176.76 (16)
C1—C5—C10—C9176.7 (2)C12—C11—C4—O231.3 (3)
C14—C15—C16—C111.5 (4)C16—C11—C4—O2147.4 (2)
C15—C16—C11—C120.9 (3)C12—C11—C4—N1148.6 (2)
C15—C16—C11—C4177.8 (2)C16—C11—C4—N132.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1C···O1i0.821.902.7231 (13)179
N1—H1D···O2ii0.862.142.907 (3)149
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x, y1, z.
 

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