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The title compound, C
18H
23NO
6, is a 4-hydroxyproline derivative of the type found in many compounds with biological activity. The crystal structure involves an intermolecular O—H
O hydrogen bond, linking molecules into a chain along a screw axis.
Supporting information
CCDC reference: 269398
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.042
- wR factor = 0.139
- Data-to-parameter ratio = 7.8
checkCIF/PLATON results
No syntax errors found
Datablock: I
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.92
| Author Response: Related to the diffraction spectrum limit (small crystal)
|
PLAT035_ALERT_1_A No _chemical_absolute_configuration info given . ?
| Author Response: given in the molecule name
|
Alert level B
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C35
Alert level C
REFLT03_ALERT_1_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 26.58
From the CIF: _diffrn_reflns_theta_full 26.58
From the CIF: _reflns_number_total 2006
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 2175
Completeness (_total/calc) 92.23%
STRVA01_ALERT_4_C Flack parameter is too small
From the CIF: _refine_ls_abs_structure_Flack -0.600
From the CIF: _refine_ls_abs_structure_Flack_su 1.300
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.92
PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 1.30
PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... -0.60
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.81
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.86 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.66 Ratio
Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
From the CIF: _diffrn_reflns_theta_max 26.58
From the CIF: _reflns_number_total 2006
From the CIF: _diffrn_reflns_limit_ max hkl 12. 12. 22.
From the CIF: _diffrn_reflns_limit_ min hkl -12. -12. 0.
TEST1: Expected hkl limits for theta max
Calculated maximum hkl 12. 12. 24.
Calculated minimum hkl -12. -12. -24.
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 26.58
From the CIF: _reflns_number_total 2006
Count of symmetry unique reflns 2175
Completeness (_total/calc) 92.23%
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
2 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
11 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 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
4 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: PLATON (Spek, 2003).
Phenylacyl (2
S,4S)-1-
tert-butoxycarbonyl-4-hydroxyprolinate
top
Crystal data top
C18H23NO6 | Dx = 1.282 Mg m−3 |
Mr = 349.37 | Melting point: 431 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.653 (2) Å | Cell parameters from 7664 reflections |
b = 9.780 (2) Å | θ = 3.8–26.6° |
c = 19.179 (4) Å | µ = 0.10 mm−1 |
V = 1810.6 (6) Å3 | T = 293 K |
Z = 4 | Cube, colourless |
F(000) = 744 | 0.3 × 0.3 × 0.3 mm |
Data collection top
Nonius KappaCDD area-detector diffractometer | 1811 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.038 |
Graphite monochromator | θmax = 26.6°, θmin = 3.8° |
φ scans | h = −12→12 |
13679 measured reflections | k = −12→12 |
2006 independent reflections | l = −22→22 |
Refinement top
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)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.139 | w = 1/[σ2(Fo2) + (0.1P)2 + 0.053P] where P = (Fo2 + 2Fc2)/3 |
S = 0.90 | (Δ/σ)max < 0.001 |
2006 reflections | Δρmax = 0.13 e Å−3 |
257 parameters | Δρmin = −0.13 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.22 (6) |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.4868 (3) | 0.0482 (2) | −0.01239 (13) | 0.0546 (6) | |
H2 | 0.5728 | 0.0333 | 0.0081 | 0.063 (8)* | |
C3 | 0.4597 (3) | −0.0043 (3) | −0.07765 (15) | 0.0646 (7) | |
H4 | 0.5273 | −0.0536 | −0.1014 | 0.086 (11)* | |
C5 | 0.3305 (3) | 0.0171 (3) | −0.10766 (15) | 0.0672 (7) | |
H6 | 0.3106 | −0.0200 | −0.1512 | 0.065 (8)* | |
C7 | 0.2328 (3) | 0.0924 (3) | −0.07337 (15) | 0.0614 (6) | |
H8 | 0.1472 | 0.1080 | −0.0942 | 0.079 (10)* | |
C9 | 0.2599 (2) | 0.1458 (2) | −0.00783 (13) | 0.0532 (5) | |
H1 | 0.1926 | 0.1968 | 0.0152 | 0.060 (7)* | |
C11 | 0.3870 (2) | 0.1230 (2) | 0.02320 (11) | 0.0458 (5) | |
C12 | 0.4236 (2) | 0.1763 (2) | 0.09350 (11) | 0.0476 (5) | |
O13 | 0.5248 (2) | 0.1379 (2) | 0.12459 (10) | 0.0720 (6) | |
C14 | 0.3296 (3) | 0.2843 (3) | 0.12552 (12) | 0.0548 (6) | |
H15 | 0.3182 | 0.3595 | 0.0930 | 0.078 (10)* | |
H16 | 0.2390 | 0.2452 | 0.1345 | 0.061 (8)* | |
O17 | 0.3872 (2) | 0.33398 (17) | 0.18896 (8) | 0.0566 (5) | |
C18 | 0.3718 (2) | 0.2516 (2) | 0.24463 (10) | 0.0467 (5) | |
O19 | 0.3072 (2) | 0.1478 (2) | 0.24393 (9) | 0.0680 (6) | |
C20 | 0.4544 (2) | 0.3088 (2) | 0.30516 (10) | 0.0472 (5) | |
H21 | 0.4719 | 0.4066 | 0.2982 | 0.046 (6)* | |
C22 | 0.5910 (3) | 0.2319 (3) | 0.31411 (12) | 0.0603 (6) | |
H23 | 0.5824 | 0.1380 | 0.2985 | 0.081 (10)* | |
H24 | 0.6648 | 0.2759 | 0.2882 | 0.097 (12)* | |
C25 | 0.6184 (2) | 0.2384 (3) | 0.39200 (12) | 0.0525 (6) | |
H26 | 0.6554 | 0.3286 | 0.4042 | 0.041 (6)* | |
O27 | 0.7136 (2) | 0.1362 (2) | 0.41147 (11) | 0.0756 (7) | |
H27 | 0.724 (5) | 0.139 (5) | 0.459 (3) | 0.112 (14)* | |
C28 | 0.4754 (2) | 0.2214 (2) | 0.42329 (11) | 0.0512 (5) | |
H29 | 0.4524 | 0.1256 | 0.4292 | 0.070 (8)* | |
H30 | 0.4688 | 0.2671 | 0.4681 | 0.067 (8)* | |
N31 | 0.38526 (19) | 0.2859 (2) | 0.37192 (9) | 0.0491 (5) | |
C32 | 0.2633 (2) | 0.3437 (2) | 0.38851 (10) | 0.0496 (5) | |
O33 | 0.21212 (19) | 0.3396 (2) | 0.44657 (9) | 0.0679 (6) | |
O34 | 0.20672 (17) | 0.4024 (2) | 0.33270 (9) | 0.0619 (5) | |
C35 | 0.0774 (2) | 0.4815 (3) | 0.33630 (14) | 0.0567 (6) | |
C36 | −0.0411 (3) | 0.3930 (4) | 0.3582 (2) | 0.0909 (11) | |
H37 | −0.1265 | 0.4414 | 0.3513 | 0.150* | |
H38 | −0.0314 | 0.3698 | 0.4066 | 0.150* | |
H39 | −0.0415 | 0.3109 | 0.3307 | 0.150* | |
C40 | 0.0970 (5) | 0.5977 (4) | 0.3858 (3) | 0.132 (2) | |
H41 | 0.0087 | 0.6374 | 0.3966 | 0.150* | |
H42 | 0.1555 | 0.6655 | 0.3647 | 0.150* | |
H43 | 0.1395 | 0.5648 | 0.4278 | 0.150* | |
C44 | 0.0606 (5) | 0.5244 (6) | 0.2609 (3) | 0.1201 (18) | |
H45 | −0.0200 | 0.5813 | 0.2565 | 0.150* | |
H46 | 0.0501 | 0.4447 | 0.2322 | 0.150* | |
H47 | 0.1410 | 0.5746 | 0.2464 | 0.150* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0557 (12) | 0.0550 (11) | 0.0531 (12) | 0.0078 (10) | −0.0005 (10) | 0.0024 (9) |
C3 | 0.0763 (16) | 0.0583 (13) | 0.0592 (15) | 0.0082 (12) | 0.0055 (12) | −0.0110 (10) |
C5 | 0.0861 (19) | 0.0591 (13) | 0.0563 (14) | −0.0056 (13) | −0.0123 (12) | −0.0130 (11) |
C7 | 0.0610 (13) | 0.0612 (12) | 0.0620 (14) | −0.0038 (11) | −0.0147 (11) | −0.0021 (11) |
C9 | 0.0491 (10) | 0.0559 (11) | 0.0546 (12) | −0.0004 (9) | −0.0047 (9) | 0.0002 (9) |
C11 | 0.0511 (10) | 0.0423 (9) | 0.0440 (10) | −0.0037 (8) | 0.0004 (8) | 0.0033 (7) |
C12 | 0.0462 (10) | 0.0527 (11) | 0.0439 (10) | −0.0016 (9) | −0.0023 (8) | 0.0086 (8) |
O13 | 0.0608 (10) | 0.0991 (14) | 0.0560 (10) | 0.0187 (10) | −0.0154 (8) | −0.0042 (10) |
C14 | 0.0641 (14) | 0.0610 (12) | 0.0392 (10) | 0.0083 (11) | −0.0107 (9) | −0.0002 (9) |
O17 | 0.0713 (10) | 0.0587 (9) | 0.0398 (8) | −0.0011 (8) | −0.0072 (7) | 0.0012 (6) |
C18 | 0.0435 (10) | 0.0589 (11) | 0.0379 (10) | 0.0000 (9) | 0.0036 (8) | −0.0002 (8) |
O19 | 0.0703 (11) | 0.0841 (12) | 0.0495 (9) | −0.0277 (11) | −0.0014 (8) | 0.0032 (8) |
C20 | 0.0453 (10) | 0.0582 (11) | 0.0379 (10) | 0.0003 (9) | 0.0025 (8) | −0.0027 (8) |
C22 | 0.0454 (11) | 0.0868 (17) | 0.0486 (13) | 0.0108 (11) | −0.0005 (9) | −0.0080 (11) |
C25 | 0.0439 (10) | 0.0649 (12) | 0.0487 (12) | 0.0051 (10) | −0.0087 (8) | −0.0098 (9) |
O27 | 0.0672 (11) | 0.1005 (15) | 0.0591 (11) | 0.0347 (12) | −0.0172 (9) | −0.0169 (10) |
C28 | 0.0529 (11) | 0.0594 (11) | 0.0414 (11) | 0.0026 (10) | −0.0050 (9) | 0.0009 (9) |
N31 | 0.0450 (9) | 0.0646 (10) | 0.0376 (9) | 0.0061 (8) | 0.0006 (7) | −0.0005 (7) |
C32 | 0.0462 (10) | 0.0645 (12) | 0.0381 (11) | 0.0009 (10) | 0.0014 (8) | −0.0053 (8) |
O33 | 0.0542 (9) | 0.1065 (14) | 0.0429 (9) | 0.0074 (10) | 0.0096 (7) | −0.0018 (9) |
O34 | 0.0480 (8) | 0.0910 (13) | 0.0467 (9) | 0.0198 (9) | 0.0030 (7) | 0.0023 (8) |
C35 | 0.0384 (10) | 0.0593 (12) | 0.0723 (15) | 0.0027 (10) | −0.0013 (10) | −0.0030 (11) |
C36 | 0.0527 (14) | 0.092 (2) | 0.128 (3) | −0.0134 (15) | −0.0049 (17) | 0.006 (2) |
C40 | 0.090 (2) | 0.078 (2) | 0.226 (6) | 0.018 (2) | −0.040 (3) | −0.066 (3) |
C44 | 0.072 (2) | 0.174 (4) | 0.114 (3) | 0.043 (3) | 0.002 (2) | 0.061 (3) |
Geometric parameters (Å, º) top
C1—C3 | 1.378 (4) | C22—H24 | 0.970 |
C1—C11 | 1.389 (3) | C25—O27 | 1.408 (3) |
C1—H2 | 0.930 | C25—C28 | 1.514 (3) |
C3—C5 | 1.389 (4) | C25—H26 | 0.980 |
C3—H4 | 0.930 | O27—H27 | 0.92 (5) |
C5—C7 | 1.366 (4) | C28—N31 | 1.458 (3) |
C5—H6 | 0.930 | C28—H29 | 0.970 |
C7—C9 | 1.386 (4) | C28—H30 | 0.970 |
C7—H8 | 0.930 | N31—C32 | 1.344 (3) |
C9—C11 | 1.383 (3) | C32—O33 | 1.219 (3) |
C9—H1 | 0.930 | C32—O34 | 1.332 (3) |
C11—C12 | 1.488 (3) | O34—C35 | 1.470 (3) |
C12—O13 | 1.204 (3) | C35—C40 | 1.492 (5) |
C12—C14 | 1.522 (3) | C35—C36 | 1.495 (4) |
C14—O17 | 1.423 (3) | C35—C44 | 1.514 (5) |
C14—H15 | 0.970 | C36—H37 | 0.960 |
C14—H16 | 0.970 | C36—H38 | 0.960 |
O17—C18 | 1.346 (3) | C36—H39 | 0.960 |
C18—O19 | 1.191 (3) | C40—H41 | 0.960 |
C18—C20 | 1.516 (3) | C40—H42 | 0.960 |
C20—N31 | 1.461 (3) | C40—H43 | 0.960 |
C20—C22 | 1.527 (3) | C44—H45 | 0.960 |
C20—H21 | 0.980 | C44—H46 | 0.960 |
C22—C25 | 1.518 (3) | C44—H47 | 0.960 |
C22—H23 | 0.970 | | |
| | | |
C3—C1—C11 | 120.8 (2) | O27—C25—C22 | 110.2 (2) |
C3—C1—H2 | 119.6 | C28—C25—C22 | 103.10 (17) |
C11—C1—H2 | 119.6 | O27—C25—H26 | 109.7 |
C1—C3—C5 | 119.3 (2) | C28—C25—H26 | 109.7 |
C1—C3—H4 | 120.3 | C22—C25—H26 | 109.7 |
C5—C3—H4 | 120.3 | C25—O27—H27 | 108 (3) |
C7—C5—C3 | 120.1 (2) | N31—C28—C25 | 103.22 (17) |
C7—C5—H6 | 119.9 | N31—C28—H29 | 111.1 |
C3—C5—H6 | 119.9 | C25—C28—H29 | 111.1 |
C5—C7—C9 | 120.6 (2) | N31—C28—H30 | 111.1 |
C5—C7—H8 | 119.7 | C25—C28—H30 | 111.1 |
C9—C7—H8 | 119.7 | H29—C28—H30 | 109.1 |
C11—C9—C7 | 119.8 (2) | C32—N31—C28 | 123.00 (18) |
C11—C9—H1 | 120.1 | C32—N31—C20 | 122.89 (18) |
C7—C9—H1 | 120.1 | C28—N31—C20 | 112.69 (17) |
C9—C11—C1 | 119.3 (2) | O33—C32—O34 | 125.6 (2) |
C9—C11—C12 | 123.0 (2) | O33—C32—N31 | 123.9 (2) |
C1—C11—C12 | 117.7 (2) | O34—C32—N31 | 110.52 (18) |
O13—C12—C11 | 122.1 (2) | C32—O34—C35 | 122.51 (18) |
O13—C12—C14 | 120.0 (2) | O34—C35—C40 | 108.8 (2) |
C11—C12—C14 | 117.84 (18) | O34—C35—C36 | 111.0 (2) |
O17—C14—C12 | 110.41 (19) | C40—C35—C36 | 111.1 (4) |
O17—C14—H15 | 109.6 | O34—C35—C44 | 101.1 (2) |
C12—C14—H15 | 109.6 | C40—C35—C44 | 114.2 (4) |
O17—C14—H16 | 109.6 | C36—C35—C44 | 110.3 (3) |
C12—C14—H16 | 109.6 | C35—C36—H37 | 109.5 |
H15—C14—H16 | 108.1 | C35—C36—H38 | 109.5 |
C18—O17—C14 | 115.52 (18) | H37—C36—H38 | 109.5 |
O19—C18—O17 | 123.97 (19) | C35—C36—H39 | 109.5 |
O19—C18—C20 | 126.78 (19) | H37—C36—H39 | 109.5 |
O17—C18—C20 | 109.18 (18) | H38—C36—H39 | 109.5 |
N31—C20—C18 | 111.97 (18) | C35—C40—H41 | 109.5 |
N31—C20—C22 | 102.73 (17) | C35—C40—H42 | 109.5 |
C18—C20—C22 | 110.99 (17) | H41—C40—H42 | 109.5 |
N31—C20—H21 | 110.3 | C35—C40—H43 | 109.5 |
C18—C20—H21 | 110.3 | H41—C40—H43 | 109.5 |
C22—C20—H21 | 110.3 | H42—C40—H43 | 109.5 |
C25—C22—C20 | 103.90 (18) | C35—C44—H45 | 109.5 |
C25—C22—H23 | 111.0 | C35—C44—H46 | 109.5 |
C20—C22—H23 | 111.0 | H45—C44—H46 | 109.5 |
C25—C22—H24 | 111.0 | C35—C44—H47 | 109.5 |
C20—C22—H24 | 111.0 | H45—C44—H47 | 109.5 |
H23—C22—H24 | 109.0 | H46—C44—H47 | 109.5 |
O27—C25—C28 | 114.3 (2) | | |
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