(2S)-Methyl 1-[(2R)-3-(benzyl­sulfan­yl)-2-(tert-butoxy­carbonyl­amino)propano­yl]pyrrolidine-2-carboxyl­ate

In the title compound, C₂₁H₃₀N₂O₅S, all bond lengths and angles are within normal ranges. Several hydrogen bonds stabilize its mol­ecular packing. The secondary structure of the title compound is best described as a β-pleated sheet-type arrangement.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.048
• wR factor = 0.104
• Data-to-parameter ratio = 18.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12B   ..  S1      ..       2.89 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           27.48
           From the CIF: _reflns_number_total               5015
           Count of symmetry unique reflns         2670
           Completeness (_total/calc)            187.83%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2345
           Fraction of Friedel pairs measured     0.878
           Are heavy atom types Z>Si present        yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14    = .          S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   0 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: COLLECT (Nonius, 2002); cell refinement: DIRAX (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); 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.

(2S)-1-[(2R)-3-(benzylsulfanyl)-2-(tert-butoxycarbonylamino)propanoyl] tetrahydro-1H-pyrrole-2-methylcarboxylate

Crystal data

C21H30N2O5S	F(000) = 452
Mr = 422.53	Dx = 1.245 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 15659 reflections
a = 6.013 (1) Å	θ = 3.4–27.5°
b = 15.597 (3) Å	µ = 0.18 mm^−1
c = 12.347 (3) Å	T = 173 K
β = 103.34 (3)°	Block, colourless
V = 1126.7 (4) Å^3	0.40 × 0.40 × 0.06 mm
Z = 2

Data collection

Nonius KappaCCD diffractometer	5015 independent reflections
Radiation source: fine-focus sealed tube	3347 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
ω– and φ–scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.933, Tmax = 0.989	k = −20→19
15659 measured reflections	l = −16→16

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.0356P)^2 + 0.2866P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
5015 reflections	Δρmax = 0.30 e Å^−3
266 parameters	Δρmin = −0.52 e Å^−3
2 restraints	Absolute structure: Flack (1983), 2345 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.06 (9)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.76660 (14)	0.44777 (5)	0.95985 (8)	0.0491 (3)
N1	0.5582 (3)	0.21194 (13)	1.05156 (17)	0.0227 (5)
C1	0.9968 (5)	0.4960 (2)	1.1687 (3)	0.0365 (7)
O1	0.2592 (3)	0.30148 (12)	1.02272 (15)	0.0302 (5)
N2	0.2990 (4)	0.36187 (15)	0.83034 (19)	0.0279 (5)
H22	0.231 (5)	0.3855 (17)	0.877 (2)	0.033*
C2	0.8819 (6)	0.5713 (2)	1.1840 (3)	0.0416 (8)
H2	0.7224	0.5758	1.1529	0.050*
O2	0.5680 (3)	0.29743 (14)	1.26406 (17)	0.0395 (5)
O3	0.2568 (3)	0.21750 (12)	1.26994 (17)	0.0370 (5)
C3	0.9970 (6)	0.6395 (2)	1.2438 (3)	0.0510 (9)
H3	0.9161	0.6905	1.2524	0.061*
O4	0.3058 (3)	0.32927 (13)	0.64953 (17)	0.0377 (5)
C4	1.2281 (6)	0.6340 (2)	1.2909 (3)	0.0526 (9)
H4	1.3057	0.6803	1.3337	0.063*
O5	0.0477 (3)	0.42489 (12)	0.69579 (14)	0.0290 (5)
C5	1.3460 (6)	0.5604 (3)	1.2753 (3)	0.0511 (9)
H5	1.5055	0.5565	1.3067	0.061*
C6	1.2318 (6)	0.4922 (2)	1.2139 (3)	0.0436 (8)
H6	1.3149	0.4425	1.2027	0.052*
C7	0.8720 (6)	0.41977 (19)	1.1067 (3)	0.0424 (8)
H7A	0.7422	0.4036	1.1394	0.051*
H7B	0.9769	0.3701	1.1135	0.051*
C8	0.7194 (5)	0.34554 (19)	0.8899 (2)	0.0335 (7)
H8A	0.7418	0.3529	0.8135	0.040*
H8B	0.8381	0.3052	0.9291	0.040*
C9	0.4833 (4)	0.30387 (17)	0.8818 (2)	0.0245 (6)
H9	0.4736	0.2526	0.8323	0.029*
C10	0.4272 (4)	0.27354 (16)	0.9920 (2)	0.0237 (6)
C11	0.7629 (5)	0.16759 (18)	1.0285 (3)	0.0329 (7)
H11B	0.9035	0.2018	1.0555	0.039*
H11A	0.7435	0.1562	0.9480	0.039*
C12	0.7700 (6)	0.08442 (18)	1.0941 (3)	0.0388 (8)
H12B	0.9286	0.0630	1.1186	0.047*
H12A	0.6751	0.0397	1.0486	0.047*
C13	0.6723 (5)	0.10915 (19)	1.1948 (3)	0.0360 (7)
H13B	0.6118	0.0582	1.2263	0.043*
H13A	0.7905	0.1367	1.2538	0.043*
C14	0.4797 (5)	0.17249 (17)	1.1457 (2)	0.0260 (6)
H14	0.3347	0.1402	1.1163	0.031*
C15	0.4423 (5)	0.23786 (18)	1.2306 (2)	0.0284 (7)
C16	0.2091 (6)	0.2707 (2)	1.3597 (3)	0.0538 (10)
H16A	0.3160	0.2560	1.4299	0.081*
H16B	0.0521	0.2605	1.3666	0.081*
H16C	0.2272	0.3313	1.3427	0.081*
C17	0.2245 (4)	0.36807 (18)	0.7190 (2)	0.0269 (6)
C18	−0.0800 (4)	0.4416 (2)	0.5798 (2)	0.0325 (7)
C19	−0.2574 (5)	0.5079 (2)	0.5985 (3)	0.0438 (8)
H19C	−0.3436	0.4843	0.6500	0.066*
H19B	−0.3625	0.5213	0.5273	0.066*
H19A	−0.1788	0.5604	0.6303	0.066*
C20	0.0774 (5)	0.4798 (2)	0.5114 (3)	0.0447 (9)
H20C	0.1488	0.5320	0.5477	0.067*
H20B	−0.0119	0.4938	0.4366	0.067*
H20A	0.1963	0.4381	0.5061	0.067*
C21	−0.1964 (5)	0.3594 (2)	0.5303 (3)	0.0437 (8)
H21C	−0.0805	0.3156	0.5286	0.066*
H21B	−0.2846	0.3705	0.4543	0.066*
H21A	−0.2992	0.3392	0.5759	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0396 (5)	0.0329 (4)	0.0624 (6)	−0.0132 (4)	−0.0134 (4)	0.0157 (4)
N1	0.0175 (11)	0.0231 (12)	0.0285 (13)	0.0013 (9)	0.0073 (9)	0.0003 (10)
C1	0.0356 (17)	0.0356 (17)	0.042 (2)	0.0046 (15)	0.0163 (15)	0.0081 (15)
O1	0.0218 (10)	0.0350 (11)	0.0344 (12)	0.0088 (9)	0.0078 (9)	0.0033 (9)
N2	0.0247 (12)	0.0329 (14)	0.0244 (14)	0.0048 (11)	0.0022 (10)	0.0005 (11)
C2	0.0339 (17)	0.0395 (18)	0.052 (2)	0.0075 (15)	0.0119 (15)	0.0028 (16)
O2	0.0377 (12)	0.0410 (12)	0.0396 (13)	−0.0094 (10)	0.0087 (10)	−0.0091 (10)
O3	0.0356 (12)	0.0382 (12)	0.0433 (13)	−0.0088 (9)	0.0216 (10)	−0.0114 (10)
C3	0.062 (2)	0.0339 (19)	0.056 (2)	0.0069 (18)	0.0105 (19)	−0.0032 (17)
O4	0.0340 (12)	0.0507 (13)	0.0293 (12)	0.0107 (10)	0.0090 (10)	0.0001 (10)
C4	0.066 (3)	0.046 (2)	0.045 (2)	−0.016 (2)	0.0106 (18)	0.0012 (19)
O5	0.0242 (10)	0.0372 (12)	0.0229 (10)	0.0059 (8)	−0.0003 (8)	−0.0003 (8)
C5	0.038 (2)	0.072 (3)	0.044 (2)	−0.0032 (19)	0.0095 (16)	0.017 (2)
C6	0.0412 (19)	0.0474 (19)	0.047 (2)	0.0143 (16)	0.0210 (16)	0.0126 (17)
C7	0.050 (2)	0.0323 (17)	0.052 (2)	0.0001 (15)	0.0249 (16)	−0.0004 (16)
C8	0.0219 (14)	0.0467 (18)	0.0313 (17)	0.0000 (13)	0.0049 (12)	0.0119 (14)
C9	0.0174 (13)	0.0274 (14)	0.0263 (15)	0.0012 (11)	0.0003 (11)	0.0017 (12)
C10	0.0171 (13)	0.0225 (14)	0.0288 (16)	−0.0007 (11)	−0.0001 (11)	−0.0050 (12)
C11	0.0194 (15)	0.0358 (17)	0.0433 (18)	0.0073 (12)	0.0070 (13)	0.0034 (14)
C12	0.0344 (17)	0.0297 (17)	0.056 (2)	0.0111 (13)	0.0174 (15)	0.0064 (15)
C13	0.0318 (16)	0.0327 (17)	0.0452 (19)	0.0066 (13)	0.0124 (14)	0.0126 (14)
C14	0.0222 (14)	0.0256 (15)	0.0303 (16)	−0.0012 (11)	0.0063 (12)	0.0007 (12)
C15	0.0232 (15)	0.0295 (16)	0.0299 (17)	0.0004 (12)	0.0010 (12)	0.0053 (13)
C16	0.058 (2)	0.058 (2)	0.054 (2)	−0.0117 (19)	0.0305 (19)	−0.0258 (19)
C17	0.0184 (14)	0.0286 (15)	0.0315 (17)	−0.0039 (12)	0.0014 (12)	0.0010 (13)
C18	0.0235 (14)	0.0457 (17)	0.0247 (16)	0.0020 (14)	−0.0019 (11)	0.0004 (15)
C19	0.0312 (18)	0.058 (2)	0.0371 (19)	0.0138 (15)	−0.0023 (14)	0.0065 (16)
C20	0.0374 (18)	0.062 (2)	0.0332 (18)	−0.0001 (15)	0.0048 (14)	0.0136 (16)
C21	0.0340 (17)	0.060 (2)	0.0341 (19)	−0.0099 (16)	0.0006 (14)	−0.0115 (16)

Geometric parameters (Å, º)

S1—C8	1.804 (3)	C8—H8A	0.9900
S1—C7	1.830 (3)	C8—H8B	0.9900
N1—C10	1.348 (3)	C9—C10	1.550 (4)
N1—C14	1.485 (3)	C9—H9	1.0000
N1—C11	1.495 (3)	C11—C12	1.524 (4)
C1—C6	1.396 (4)	C11—H11B	0.9900
C1—C2	1.398 (4)	C11—H11A	0.9900
C1—C7	1.515 (4)	C12—C13	1.542 (4)
O1—C10	1.237 (3)	C12—H12B	0.9900
N2—C17	1.347 (3)	C12—H12A	0.9900
N2—C9	1.458 (3)	C13—C14	1.537 (4)
N2—H22	0.860 (17)	C13—H13B	0.9900
C2—C3	1.386 (5)	C13—H13A	0.9900
C2—H2	0.9500	C14—C15	1.516 (4)
O2—C15	1.209 (3)	C14—H14	1.0000
O3—C15	1.353 (3)	C16—H16A	0.9800
O3—C16	1.465 (4)	C16—H16B	0.9800
C3—C4	1.380 (5)	C16—H16C	0.9800
C3—H3	0.9500	C18—C21	1.520 (4)
O4—C17	1.239 (3)	C18—C20	1.526 (4)
C4—C5	1.386 (5)	C18—C19	1.541 (4)
C4—H4	0.9500	C19—H19C	0.9800
O5—C17	1.363 (3)	C19—H19B	0.9800
O5—C18	1.484 (3)	C19—H19A	0.9800
C5—C6	1.392 (5)	C20—H20C	0.9800
C5—H5	0.9500	C20—H20B	0.9800
C6—H6	0.9500	C20—H20A	0.9800
C7—H7A	0.9900	C21—H21C	0.9800
C7—H7B	0.9900	C21—H21B	0.9800
C8—C9	1.544 (4)	C21—H21A	0.9800
C8—S1—C7	104.10 (13)	C11—C12—C13	104.3 (2)
C10—N1—C14	118.1 (2)	C11—C12—H12B	110.9
C10—N1—C11	129.0 (2)	C13—C12—H12B	110.9
C14—N1—C11	112.4 (2)	C11—C12—H12A	110.9
C6—C1—C2	117.9 (3)	C13—C12—H12A	110.9
C6—C1—C7	120.5 (3)	H12B—C12—H12A	108.9
C2—C1—C7	121.7 (3)	C14—C13—C12	103.6 (2)
C17—N2—C9	122.0 (2)	C14—C13—H13B	111.0
C17—N2—H22	124 (2)	C12—C13—H13B	111.0
C9—N2—H22	113.9 (19)	C14—C13—H13A	111.0
C3—C2—C1	121.1 (3)	C12—C13—H13A	111.0
C3—C2—H2	119.5	H13B—C13—H13A	109.0
C1—C2—H2	119.5	N1—C14—C15	112.8 (2)
C15—O3—C16	117.4 (2)	N1—C14—C13	103.2 (2)
C4—C3—C2	120.5 (3)	C15—C14—C13	112.2 (2)
C4—C3—H3	119.8	N1—C14—H14	109.5
C2—C3—H3	119.8	C15—C14—H14	109.5
C3—C4—C5	119.4 (3)	C13—C14—H14	109.5
C3—C4—H4	120.3	O2—C15—O3	124.0 (3)
C5—C4—H4	120.3	O2—C15—C14	124.9 (3)
C17—O5—C18	121.5 (2)	O3—C15—C14	110.9 (2)
C4—C5—C6	120.3 (3)	O3—C16—H16A	109.5
C4—C5—H5	119.8	O3—C16—H16B	109.5
C6—C5—H5	119.8	H16A—C16—H16B	109.5
C5—C6—C1	120.8 (3)	O3—C16—H16C	109.5
C5—C6—H6	119.6	H16A—C16—H16C	109.5
C1—C6—H6	119.6	H16B—C16—H16C	109.5
C1—C7—S1	109.3 (2)	O4—C17—N2	125.5 (2)
C1—C7—H7A	109.8	O4—C17—O5	125.8 (2)
S1—C7—H7A	109.8	N2—C17—O5	108.7 (2)
C1—C7—H7B	109.8	O5—C18—C21	109.1 (2)
S1—C7—H7B	109.8	O5—C18—C20	110.7 (2)
H7A—C7—H7B	108.3	C21—C18—C20	113.2 (3)
C9—C8—S1	116.4 (2)	O5—C18—C19	101.2 (2)
C9—C8—H8A	108.2	C21—C18—C19	110.8 (2)
S1—C8—H8A	108.2	C20—C18—C19	111.1 (3)
C9—C8—H8B	108.2	C18—C19—H19C	109.5
S1—C8—H8B	108.2	C18—C19—H19B	109.5
H8A—C8—H8B	107.4	H19C—C19—H19B	109.5
N2—C9—C8	111.2 (2)	C18—C19—H19A	109.5
N2—C9—C10	105.9 (2)	H19C—C19—H19A	109.5
C8—C9—C10	117.0 (2)	H19B—C19—H19A	109.5
N2—C9—H9	107.4	C18—C20—H20C	109.5
C8—C9—H9	107.4	C18—C20—H20B	109.5
C10—C9—H9	107.4	H20C—C20—H20B	109.5
O1—C10—N1	120.0 (2)	C18—C20—H20A	109.5
O1—C10—C9	121.3 (2)	H20C—C20—H20A	109.5
N1—C10—C9	118.6 (2)	H20B—C20—H20A	109.5
N1—C11—C12	102.5 (2)	C18—C21—H21C	109.5
N1—C11—H11B	111.3	C18—C21—H21B	109.5
C12—C11—H11B	111.3	H21C—C21—H21B	109.5
N1—C11—H11A	111.3	C18—C21—H21A	109.5
C12—C11—H11A	111.3	H21C—C21—H21A	109.5
H11B—C11—H11A	109.2	H21B—C21—H21A	109.5
C6—C1—C2—C3	−1.1 (5)	C10—N1—C11—C12	−157.6 (3)
C7—C1—C2—C3	178.0 (3)	C14—N1—C11—C12	14.0 (3)
C1—C2—C3—C4	−0.8 (5)	N1—C11—C12—C13	−31.6 (3)
C2—C3—C4—C5	1.8 (5)	C11—C12—C13—C14	38.2 (3)
C3—C4—C5—C6	−0.8 (5)	C10—N1—C14—C15	−56.8 (3)
C4—C5—C6—C1	−1.1 (5)	C11—N1—C14—C15	130.6 (2)
C2—C1—C6—C5	2.0 (5)	C10—N1—C14—C13	−178.1 (2)
C7—C1—C6—C5	−177.0 (3)	C11—N1—C14—C13	9.3 (3)
C6—C1—C7—S1	−113.6 (3)	C12—C13—C14—N1	−28.7 (3)
C2—C1—C7—S1	67.3 (4)	C12—C13—C14—C15	−150.3 (2)
C8—S1—C7—C1	159.8 (2)	C16—O3—C15—O2	−0.9 (4)
C7—S1—C8—C9	87.3 (2)	C16—O3—C15—C14	175.0 (3)
C17—N2—C9—C8	84.8 (3)	N1—C14—C15—O2	−42.3 (4)
C17—N2—C9—C10	−147.0 (2)	C13—C14—C15—O2	73.8 (4)
S1—C8—C9—N2	54.8 (3)	N1—C14—C15—O3	141.9 (2)
S1—C8—C9—C10	−67.1 (3)	C13—C14—C15—O3	−102.1 (3)
C14—N1—C10—O1	6.9 (3)	C9—N2—C17—O4	−2.8 (4)
C11—N1—C10—O1	178.1 (3)	C9—N2—C17—O5	178.1 (2)
C14—N1—C10—C9	−169.4 (2)	C18—O5—C17—O4	4.5 (4)
C11—N1—C10—C9	1.8 (4)	C18—O5—C17—N2	−176.3 (2)
N2—C9—C10—O1	−3.0 (3)	C17—O5—C18—C21	62.6 (3)
C8—C9—C10—O1	121.7 (3)	C17—O5—C18—C20	−62.5 (3)
N2—C9—C10—N1	173.2 (2)	C17—O5—C18—C19	179.6 (2)
C8—C9—C10—N1	−62.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H22···O1	0.86 (2)	2.20 (3)	2.617 (3)	109 (2)
C12—H12B···S1^i	0.99	2.89	3.689 (3)	138
C7—H7B···O1^ii	0.99	2.48	3.319 (4)	142
C8—H8B···O1^ii	0.99	2.53	3.353 (4)	140
C21—H21B···O2^iii	0.98	2.58	3.405 (4)	142

Symmetry codes: (i) −x+2, y−1/2, −z+2; (ii) x+1, y, z; (iii) x−1, y, z−1.