Phenacyl (2S,4S)-1-tert-butoxy­carbonyl-4-hydroxy­prolinate

Chabaud, P.; Worf, M.; Courcambeck, J.; Camplo, M.; Pèpe, G.

doi:10.1107/S1600536805005404

Phenacyl (2S,4S)-1-tert-butoxycarbonyl-4-hydroxyprolinate

P. Chabaud, M. Worf, J. Courcambeck, M. Camplo and G. Pèpe

The title compound, C₁₈H₂₃NO₆, 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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805005404/cf6401sup1.cif Contains datablocks 4, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805005404/cf64014sup2.hkl Contains datablock 4

CCDC reference: 269398

checkCIF report

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

Computing details top

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 (2S,4S)-1-tert-butoxycarbonyl-4-hydroxyprolinate top

Crystal data top

C₁₈H₂₃NO₆	D_x = 1.282 Mg m⁻³
M_r = 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	R_int = 0.038
Graphite monochromator	θ_max = 26.6°, θ_min = 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(F_o²) + (0.1P)² + 0.053P] where P = (F_o² + 2F_c²)/3
S = 0.90	(Δ/σ)_max < 0.001
2006 reflections	Δρ_max = 0.13 e Å⁻³
257 parameters	Δρ_min = −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	U_iso*/U_eq
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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Phenacyl (2S,4S)-1-tert-butoxy­carbonyl-4-hydroxy­prolinate

Supporting information

Key indicators

checkCIF/PLATON results

Phenacyl (2S,4S)-1-tert-butoxycarbonyl-4-hydroxyprolinate