(4R)-4-Hydr­oxy-1-[(2S)-2-hydroxy­dodec­yl]-l-proline monohydrate

Peifer, C.; Werz, O.; Poeckel, D.; Schollmeyer, D.; Laufer, S.

doi:10.1107/S1600536806042930

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(4R)-4-Hydroxy-1-[(2S)-2-hydroxydodecyl]-L-proline monohydrate

C. Peifer, O. Werz, D. Poeckel, D. Schollmeyer and S. Laufer

The title compound, C₁₇H₃₃NO₄·H₂O, was found to be the S diastereoisomer with respect to the asymmetric C atom at the OH group on the chain. The X-ray structure was determined as part of a study of the molecular geometry and stereochemistry of L-proline derivatives for pre-coating thin-layer chromatography plates intended for enantiomeric separation.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806042930/bt2198sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806042930/bt2198Isup2.hkl Contains datablock I

CCDC reference: 627339

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R factor = 0.047
wR factor = 0.144
Data-to-parameter ratio = 10.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.67 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.58 Ratio

Alert level C
PLAT057_ALERT_3_C Correction for Absorption Required   RT(exp) ...       1.11
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT751_ALERT_4_C Bond    Calc     0.89000, Rep     0.89(3) ......  Senseless su
              N1   -H1      1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      107.00, Rep    106.7(4) ......  Senseless su
              C10  -N1   -H1      1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      103.00, Rep    103.2(3) ......  Senseless su
              C5   -N1   -H1      1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      112.00, Rep    112.2(4) ......  Senseless su
              C2   -N1   -H1      1.555   1.555   1.555
PLAT755_ALERT_4_C D-H     Calc     0.89000, Rep     0.89(3) ......  Senseless su
              N1   -H1      1.555   1.555
PLAT756_ALERT_4_C H...A   Calc     2.06000, Rep     2.06(3) ......  Senseless su
              H1   -O6      1.555   1.655
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              H2 O

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           70.07
           From the CIF: _reflns_number_total               2261
           Count of symmetry unique reflns         2264
           Completeness (_total/calc)             99.87%
           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 C2     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4     = .          R
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
   9 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   8 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2005); software used to prepare material for publication: SHELXL97.

(I) top

Crystal data top

C₁₇H₃₃NO₄·H₂O	D_x = 1.115 Mg m⁻³
M_r = 333.46	Melting point: 168 K
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 5.4341 (2) Å	θ = 35–43°
b = 7.8324 (2) Å	µ = 0.65 mm⁻¹
c = 46.6831 (10) Å	T = 298 K
V = 1986.93 (10) Å³	Plate, colourless
Z = 4	0.60 × 0.30 × 0.20 mm
F(000) = 736

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.020
Radiation source: rotating anode	θ_max = 70.1°, θ_min = 1.9°
Graphite monochromator	h = −6→6
ω/2θ scans	k = −9→9
4012 measured reflections	l = −56→56
2261 independent reflections	3 standard reflections every 60 min
1932 reflections with I > 2σ(I)	intensity decay: 5%

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.047	w = 1/[σ²(F_o²) + (0.0762P)² + 0.303P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.144	(Δ/σ)_max = 0.001
S = 1.08	Δρ_max = 0.33 e Å⁻³
2261 reflections	Δρ_min = −0.26 e Å⁻³
211 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0038 (5)
Primary atom site location: structure-invariant direct methods	Absolute structure: The absolute configuration was assigned to agree with that of (2S,4R)-4-hydroxyproline. The Flack parameter was calculated according to Flack (Flack, 1983).
Secondary atom site location: difference Fourier map

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
N1	0.6421 (4)	0.5115 (2)	0.55883 (4)	0.0403 (5)
H1	0.804 (6)	0.5001 (5)	0.55666 (9)	0.048*
C2	0.5070 (5)	0.3437 (3)	0.55505 (5)	0.0401 (5)
H2	0.3847	0.3324	0.5704	0.048*
C3	0.3730 (6)	0.3618 (3)	0.52651 (5)	0.0477 (6)
H3A	0.4734	0.3197	0.5109	0.057*
H3B	0.2184	0.3000	0.5267	0.057*
C4	0.3297 (5)	0.5520 (3)	0.52372 (5)	0.0446 (6)
H4	0.2956	0.5845	0.5038	0.054*
C5	0.5697 (5)	0.6237 (4)	0.53386 (5)	0.0438 (6)
H5A	0.5506	0.7414	0.5399	0.053*
H5B	0.6925	0.6187	0.5188	0.053*
O6	0.1326 (3)	0.5973 (2)	0.54213 (4)	0.0525 (5)
H6	0.1850	0.6558	0.5553	0.079*
C7	0.6852 (6)	0.1941 (3)	0.55687 (6)	0.0532 (7)
O8	0.9028 (4)	0.2254 (3)	0.56361 (5)	0.0686 (6)
O9	0.6015 (5)	0.0513 (3)	0.55108 (6)	0.0824 (7)
C10	0.6022 (6)	0.5947 (3)	0.58741 (5)	0.0531 (7)
H10A	0.4272	0.6112	0.5904	0.064*
H10B	0.6799	0.7062	0.5874	0.064*
C11	0.7061 (6)	0.4894 (5)	0.61192 (5)	0.0600 (8)
H11	0.6254	0.3775	0.6122	0.072*
O12	0.9636 (4)	0.4660 (4)	0.60850 (4)	0.0785 (8)
H12	0.9905	0.4170	0.5933	0.118*
C13	0.6558 (8)	0.5799 (5)	0.64005 (6)	0.0793 (10)
H13A	0.7284	0.6930	0.6393	0.095*
H13B	0.4794	0.5939	0.6422	0.095*
C14	0.7552 (9)	0.4871 (6)	0.66606 (6)	0.0905 (13)
H14A	0.6966	0.3701	0.6658	0.109*
H14B	0.9334	0.4843	0.6650	0.109*
C15	0.6790 (11)	0.5701 (6)	0.69396 (6)	0.1051 (15)
H15A	0.7275	0.6893	0.6935	0.126*
H15B	0.5010	0.5663	0.6954	0.126*
C16	0.7871 (11)	0.4889 (7)	0.72040 (7)	0.1086 (17)
H16A	0.7451	0.3685	0.7204	0.130*
H16B	0.9649	0.4976	0.7194	0.130*
C17	0.7014 (11)	0.5669 (7)	0.74809 (7)	0.1133 (18)
H17A	0.7379	0.6881	0.7477	0.136*
H17B	0.5241	0.5546	0.7493	0.136*
C18	0.8144 (12)	0.4912 (8)	0.77455 (7)	0.1179 (19)
H18A	0.9911	0.5076	0.7737	0.141*
H18B	0.7836	0.3692	0.7745	0.141*
C19	0.7207 (12)	0.5650 (7)	0.80236 (7)	0.1158 (18)
H19A	0.7517	0.6869	0.8024	0.139*
H19B	0.5439	0.5487	0.8032	0.139*
C20	0.8319 (13)	0.4901 (7)	0.82863 (7)	0.1171 (18)
H20A	1.0079	0.5107	0.8282	0.141*
H20B	0.8070	0.3675	0.8282	0.141*
C21	0.7313 (15)	0.5583 (8)	0.85651 (8)	0.138 (2)
H21A	0.7613	0.6803	0.8572	0.166*
H21B	0.5545	0.5415	0.8566	0.166*
C22	0.8332 (15)	0.4816 (8)	0.88237 (9)	0.147 (3)
H22A	0.8101	0.3601	0.8817	0.220*
H22B	0.7507	0.5273	0.8989	0.220*
H22C	1.0057	0.5068	0.8835	0.220*
O1W	1.1412 (5)	−0.0650 (3)	0.53874 (5)	0.0731 (7)
H1W	1.2607	−0.0356	0.5483	0.110*
H2W	1.0145	−0.0397	0.5473	0.110*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0336 (10)	0.0423 (10)	0.0449 (10)	−0.0002 (9)	0.0020 (8)	0.0010 (8)
C2	0.0354 (12)	0.0365 (11)	0.0485 (12)	0.0007 (10)	0.0065 (10)	0.0009 (10)
C3	0.0489 (15)	0.0431 (13)	0.0511 (12)	0.0026 (14)	0.0011 (12)	−0.0058 (11)
C4	0.0382 (13)	0.0489 (13)	0.0467 (11)	−0.0004 (12)	−0.0001 (11)	0.0051 (11)
C5	0.0346 (12)	0.0459 (13)	0.0510 (12)	0.0005 (11)	0.0018 (10)	0.0086 (11)
O6	0.0314 (9)	0.0513 (10)	0.0749 (11)	0.0004 (9)	0.0053 (9)	0.0002 (9)
C7	0.0559 (18)	0.0415 (14)	0.0623 (15)	0.0135 (13)	0.0106 (14)	0.0062 (12)
O8	0.0461 (12)	0.0633 (13)	0.0964 (15)	0.0136 (11)	0.0048 (11)	0.0137 (11)
O9	0.0791 (17)	0.0417 (11)	0.1264 (19)	0.0128 (13)	−0.0026 (16)	−0.0085 (12)
C10	0.0576 (16)	0.0532 (15)	0.0487 (12)	−0.0008 (15)	0.0003 (12)	−0.0086 (11)
C11	0.0602 (18)	0.074 (2)	0.0456 (13)	−0.0006 (17)	−0.0012 (12)	−0.0018 (14)
O12	0.0579 (13)	0.121 (2)	0.0566 (11)	0.0044 (16)	−0.0083 (10)	0.0017 (13)
C13	0.097 (3)	0.092 (2)	0.0482 (14)	−0.002 (3)	−0.0022 (17)	−0.0072 (15)
C14	0.113 (3)	0.111 (3)	0.0471 (14)	0.001 (3)	−0.0047 (18)	−0.0040 (17)
C15	0.139 (4)	0.126 (4)	0.0501 (16)	0.004 (4)	0.000 (2)	−0.006 (2)
C16	0.141 (4)	0.133 (4)	0.0513 (17)	0.007 (4)	−0.003 (2)	−0.006 (2)
C17	0.153 (5)	0.134 (4)	0.0522 (17)	0.004 (4)	0.002 (2)	−0.002 (2)
C18	0.157 (5)	0.145 (4)	0.0520 (17)	0.009 (5)	0.000 (3)	−0.006 (2)
C19	0.156 (5)	0.134 (4)	0.0567 (18)	−0.005 (4)	0.006 (3)	−0.006 (2)
C20	0.163 (5)	0.130 (4)	0.0576 (18)	−0.007 (5)	−0.001 (3)	−0.006 (2)
C21	0.205 (7)	0.146 (5)	0.064 (2)	0.002 (6)	0.004 (3)	−0.010 (3)
C22	0.216 (7)	0.152 (5)	0.074 (2)	−0.015 (6)	−0.008 (4)	−0.012 (3)
O1W	0.0744 (16)	0.0564 (12)	0.0884 (14)	0.0167 (14)	−0.0013 (13)	−0.0140 (11)

Geometric parameters (Å, º) top

N1—C10	1.501 (3)	C14—H14A	0.9700
N1—C5	1.512 (3)	C14—H14B	0.9700
N1—C2	1.516 (3)	C15—C16	1.508 (6)
N1—H1	0.89 (3)	C15—H15A	0.9700
C2—C7	1.522 (4)	C15—H15B	0.9700
C2—C3	1.525 (4)	C16—C17	1.504 (5)
C2—H2	0.9800	C16—H16A	0.9700
C3—C4	1.514 (4)	C16—H16B	0.9700
C3—H3A	0.9700	C17—C18	1.501 (6)
C3—H3B	0.9700	C17—H17A	0.9700
C4—O6	1.418 (3)	C17—H17B	0.9700
C4—C5	1.497 (4)	C18—C19	1.510 (6)
C4—H4	0.9800	C18—H18A	0.9700
C5—H5A	0.9700	C18—H18B	0.9700
C5—H5B	0.9700	C19—C20	1.487 (6)
O6—H6	0.8200	C19—H19A	0.9700
C7—O9	1.237 (4)	C19—H19B	0.9700
C7—O8	1.248 (4)	C20—C21	1.509 (6)
C10—C11	1.519 (4)	C20—H20A	0.9700
C10—H10A	0.9700	C20—H20B	0.9700
C10—H10B	0.9700	C21—C22	1.458 (7)
C11—O12	1.420 (4)	C21—H21A	0.9700
C11—C13	1.517 (4)	C21—H21B	0.9700
C11—H11	0.9800	C22—H22A	0.9600
O12—H12	0.8200	C22—H22B	0.9600
C13—C14	1.515 (5)	C22—H22C	0.9600
C13—H13A	0.9700	O1W—H1W	0.8200
C13—H13B	0.9700	O1W—H2W	0.8200
C14—C15	1.513 (5)

C10—N1—C5	113.3 (2)	C15—C14—H14A	109.1
C10—N1—C2	114.24 (19)	C13—C14—H14A	109.1
C5—N1—C2	106.76 (19)	C15—C14—H14B	109.1
C10—N1—H1	106.7 (4)	C13—C14—H14B	109.1
C5—N1—H1	103.2 (3)	H14A—C14—H14B	107.8
C2—N1—H1	112.2 (4)	C16—C15—C14	114.6 (4)
N1—C2—C7	110.7 (2)	C16—C15—H15A	108.6
N1—C2—C3	104.60 (19)	C14—C15—H15A	108.6
C7—C2—C3	115.1 (2)	C16—C15—H15B	108.6
N1—C2—H2	108.8	C14—C15—H15B	108.6
C7—C2—H2	108.8	H15A—C15—H15B	107.6
C3—C2—H2	108.8	C17—C16—C15	114.3 (5)
C4—C3—C2	104.0 (2)	C17—C16—H16A	108.7
C4—C3—H3A	111.0	C15—C16—H16A	108.7
C2—C3—H3A	111.0	C17—C16—H16B	108.7
C4—C3—H3B	111.0	C15—C16—H16B	108.7
C2—C3—H3B	111.0	H16A—C16—H16B	107.6
H3A—C3—H3B	109.0	C18—C17—C16	114.8 (5)
O6—C4—C5	111.9 (2)	C18—C17—H17A	108.6
O6—C4—C3	108.1 (2)	C16—C17—H17A	108.6
C5—C4—C3	101.9 (2)	C18—C17—H17B	108.6
O6—C4—H4	111.5	C16—C17—H17B	108.6
C5—C4—H4	111.5	H17A—C17—H17B	107.5
C3—C4—H4	111.5	C17—C18—C19	114.7 (5)
C4—C5—N1	104.6 (2)	C17—C18—H18A	108.6
C4—C5—H5A	110.8	C19—C18—H18A	108.6
N1—C5—H5A	110.8	C17—C18—H18B	108.6
C4—C5—H5B	110.8	C19—C18—H18B	108.6
N1—C5—H5B	110.8	H18A—C18—H18B	107.6
H5A—C5—H5B	108.9	C20—C19—C18	114.9 (5)
C4—O6—H6	109.5	C20—C19—H19A	108.5
O9—C7—O8	125.5 (3)	C18—C19—H19A	108.5
O9—C7—C2	116.7 (3)	C20—C19—H19B	108.5
O8—C7—C2	117.7 (3)	C18—C19—H19B	108.5
N1—C10—C11	112.3 (2)	H19A—C19—H19B	107.5
N1—C10—H10A	109.1	C19—C20—C21	115.1 (5)
C11—C10—H10A	109.1	C19—C20—H20A	108.5
N1—C10—H10B	109.1	C21—C20—H20A	108.5
C11—C10—H10B	109.1	C19—C20—H20B	108.5
H10A—C10—H10B	107.9	C21—C20—H20B	108.5
O12—C11—C13	109.6 (3)	H20A—C20—H20B	107.5
O12—C11—C10	110.6 (3)	C22—C21—C20	115.5 (6)
C13—C11—C10	109.3 (3)	C22—C21—H21A	108.4
O12—C11—H11	109.1	C20—C21—H21A	108.4
C13—C11—H11	109.1	C22—C21—H21B	108.4
C10—C11—H11	109.1	C20—C21—H21B	108.4
C11—O12—H12	109.5	H21A—C21—H21B	107.5
C14—C13—C11	113.9 (3)	C21—C22—H22A	109.5
C14—C13—H13A	108.8	C21—C22—H22B	109.5
C11—C13—H13A	108.8	H22A—C22—H22B	109.5
C14—C13—H13B	108.8	C21—C22—H22C	109.5
C11—C13—H13B	108.8	H22A—C22—H22C	109.5
H13A—C13—H13B	107.7	H22B—C22—H22C	109.5
C15—C14—C13	112.7 (4)	H1W—O1W—H2W	109.5

C10—N1—C2—C7	−105.7 (2)	C3—C2—C7—O8	124.8 (3)
C5—N1—C2—C7	128.2 (2)	C5—N1—C10—C11	−172.7 (2)
C10—N1—C2—C3	129.7 (2)	C2—N1—C10—C11	64.8 (3)
C5—N1—C2—C3	3.7 (2)	N1—C10—C11—O12	60.1 (4)
N1—C2—C3—C4	−28.0 (3)	N1—C10—C11—C13	−179.2 (3)
C7—C2—C3—C4	−149.7 (2)	O12—C11—C13—C14	−57.8 (5)
C2—C3—C4—O6	−76.2 (3)	C10—C11—C13—C14	−179.2 (3)
C2—C3—C4—C5	41.9 (3)	C11—C13—C14—C15	−173.8 (4)
O6—C4—C5—N1	75.9 (2)	C13—C14—C15—C16	−176.2 (4)
C3—C4—C5—N1	−39.5 (2)	C14—C15—C16—C17	−177.3 (5)
C10—N1—C5—C4	−104.2 (2)	C15—C16—C17—C18	−178.0 (5)
C2—N1—C5—C4	22.4 (2)	C16—C17—C18—C19	−177.7 (5)
N1—C2—C7—O9	−172.5 (3)	C17—C18—C19—C20	179.9 (5)
C3—C2—C7—O9	−54.2 (4)	C18—C19—C20—C21	−177.6 (5)
N1—C2—C7—O8	6.4 (3)	C19—C20—C21—C22	178.0 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6ⁱ	0.89 (3)	2.06 (3)	2.857 (3)	149 (1)
O6—H6···O1Wⁱⁱ	0.82	2.33	2.650 (3)	104
O12—H12···O8	0.82	2.10	2.838 (4)	150
O1W—H2W···O8	0.82	2.29	2.863 (3)	127
O1W—H2W···O9	0.82	2.36	3.124 (4)	155
O1W—H1W···O9ⁱ	0.82	1.98	2.724 (4)	151

Symmetry codes: (i) x+1, y, z; (ii) x−1, y+1, z.

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