(1R,3R)-Methyl 6-tert-butoxy­carbonyl­amino-1,5-dioxo-2,3-di­hydro-5H-1,3-thia­zolo­[3,2-a]­pyridine-3-carboxyl­ate

The absolute configuration has been determined for the title compound, C₁₄H₁₈N₂O₆S, a fluorescent dipeptide analogue, which can act as a rigid backbone chromophore in peptides. Intermolecular N—H...O=C hydrogen bonds [H...O = 2.37 (2) Å] are observed in the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.024
• wR factor = 0.057
• Data-to-parameter ratio = 10.5

checkCIF/PLATON results

No syntax errors found



Alert level A
DIFF020_ALERT_1_A  _diffrn_standards_interval_count and
            _diffrn_standards_interval_time are missing. Number of measurements
            between standards or time (min) between standards.

Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.21 Ratio

Alert level C
PLAT432_ALERT_2_C Short Inter X...Y Contact  O1     ..  C2      ..       3.01 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           26.09
           From the CIF: _reflns_number_total               2931
           Count of symmetry unique reflns         1755
           Completeness (_total/calc)            167.01%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1176
           Fraction of Friedel pairs measured     0.670
           Are heavy atom types Z>Si present          yes

   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   1 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
   1 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

Data collection: X-AREA (Stoe & Cie, 2003); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2004); software used to prepare material for publication: WinGX(Farrugia, 1999).

Methyl (1R,3R)-6-tert-butoxycarbonylamino-1,5-dioxo-2,3-dihydro-5H-1,3- thiazolo[3,2-a]pyridine-3-carboxylate

Crystal data

C14H18N2O6S	F(000) = 360
Mr = 342.36	Dx = 1.415 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5921 reflections
a = 11.4352 (15) Å	θ = 1.7–25°
b = 6.1405 (5) Å	µ = 0.23 mm^−1
c = 11.5469 (14) Å	T = 193 K
β = 97.785 (15)°	Plate, colourless
V = 803.33 (16) Å^3	0.41 × 0.22 × 0.09 mm
Z = 2

Data collection

Stoe IPDS-2 diffractometer	Rint = 0.024
ω scans	θmax = 26.1°, θmin = 1.8°
5976 measured reflections	h = −13→14
2931 independent reflections	k = −7→7
2665 reflections with I > 2σ(I)	l = −14→13

Refinement

Refinement on F^2	All H-atom parameters refined
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0375P)^2] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.024	(Δ/σ)max < 0.001
wR(F^2) = 0.057	Δρmax = 0.18 e Å^−3
S = 0.99	Δρmin = −0.19 e Å^−3
2931 reflections	Absolute structure: Flack (1983), 1222 Friedels
280 parameters	Absolute structure parameter: 0.01 (6)
1 restraint

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C2	0.54536 (16)	0.0180 (4)	0.66534 (15)	0.0334 (4)
C3	0.57899 (13)	0.2238 (3)	0.73791 (14)	0.0218 (3)
C5	0.72059 (12)	0.5206 (3)	0.73565 (12)	0.0195 (3)
C6	0.81578 (13)	0.6141 (3)	0.67971 (13)	0.0193 (3)
C7	0.85134 (13)	0.5186 (3)	0.58356 (12)	0.0228 (3)
C8	0.79650 (14)	0.3254 (3)	0.53662 (14)	0.0253 (4)
C9	0.70860 (13)	0.2373 (3)	0.58843 (14)	0.0214 (3)
C10	0.62514 (13)	0.1621 (3)	0.86370 (14)	0.0217 (3)
C11	0.5721 (2)	0.1220 (4)	1.05262 (18)	0.0427 (5)
C12	0.96408 (14)	0.9068 (3)	0.71948 (14)	0.0230 (3)
C13	1.09471 (14)	1.1847 (3)	0.82090 (15)	0.0277 (4)
C14	1.13636 (19)	1.2861 (4)	0.71435 (19)	0.0390 (5)
C15	1.18210 (18)	1.0189 (5)	0.8785 (2)	0.0448 (5)
C16	1.0671 (2)	1.3566 (4)	0.9073 (2)	0.0437 (5)
N4	0.67366 (10)	0.3308 (2)	0.68613 (11)	0.0197 (3)
N5	0.86011 (11)	0.8045 (2)	0.73504 (12)	0.0225 (3)
O1	0.53637 (11)	0.0833 (2)	0.43475 (11)	0.0398 (3)
O2	0.72532 (9)	0.1119 (2)	0.89708 (10)	0.0305 (3)
O3	0.53774 (10)	0.1648 (2)	0.92897 (11)	0.0331 (3)
O4	0.68227 (10)	0.6014 (2)	0.82118 (10)	0.0276 (3)
O5	1.02941 (10)	0.8490 (2)	0.65219 (12)	0.0372 (3)
O6	0.97841 (10)	1.07821 (19)	0.79174 (10)	0.0281 (3)
S1	0.62060 (3)	0.00815 (7)	0.53629 (3)	0.02583 (10)
H3	0.5108 (15)	0.324 (3)	0.7361 (14)	0.019 (4)*
H5	0.8239 (16)	0.856 (4)	0.7911 (17)	0.030 (5)*
H7	0.9129 (15)	0.585 (3)	0.5470 (15)	0.022 (4)*
H8	0.8186 (17)	0.262 (4)	0.4736 (18)	0.035 (5)*
H21	0.464 (2)	0.024 (5)	0.6328 (19)	0.049 (6)*
H22	0.5661 (19)	−0.109 (4)	0.709 (2)	0.049 (7)*
H111	0.625 (2)	0.243 (5)	1.084 (2)	0.072 (8)*
H112	0.500 (2)	0.114 (4)	1.0889 (18)	0.047 (6)*
H113	0.613 (2)	−0.022 (5)	1.064 (2)	0.055 (7)*
H141	1.079 (3)	1.384 (6)	0.674 (3)	0.080 (9)*
H142	1.203 (2)	1.385 (4)	0.739 (2)	0.049 (6)*
H143	1.157 (2)	1.174 (5)	0.667 (2)	0.065 (8)*
H151	1.154 (2)	0.949 (5)	0.945 (3)	0.072 (9)*
H152	1.195 (2)	0.904 (5)	0.825 (2)	0.060 (8)*
H153	1.256 (2)	1.096 (4)	0.909 (2)	0.053 (6)*
H161	1.035 (2)	1.290 (5)	0.977 (2)	0.064 (8)*
H162	1.003 (2)	1.462 (5)	0.865 (2)	0.080 (9)*
H163	1.137 (2)	1.435 (4)	0.938 (2)	0.060 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0373 (10)	0.0310 (10)	0.0312 (9)	−0.0131 (10)	0.0014 (7)	−0.0008 (10)
C3	0.0182 (7)	0.0204 (8)	0.0270 (9)	−0.0002 (6)	0.0034 (6)	0.0028 (7)
C5	0.0197 (6)	0.0191 (7)	0.0193 (7)	0.0005 (7)	0.0015 (5)	0.0003 (8)
C6	0.0196 (7)	0.0190 (8)	0.0186 (7)	−0.0002 (6)	−0.0004 (6)	0.0038 (6)
C7	0.0238 (7)	0.0265 (8)	0.0187 (7)	−0.0011 (8)	0.0053 (6)	0.0016 (8)
C8	0.0283 (8)	0.0285 (9)	0.0192 (8)	0.0021 (7)	0.0039 (6)	−0.0029 (8)
C9	0.0243 (8)	0.0190 (8)	0.0198 (8)	0.0033 (6)	−0.0011 (6)	−0.0008 (6)
C10	0.0232 (8)	0.0166 (8)	0.0260 (8)	−0.0017 (6)	0.0054 (6)	−0.0013 (7)
C11	0.0486 (12)	0.0523 (15)	0.0297 (10)	−0.0136 (12)	0.0141 (9)	0.0069 (10)
C12	0.0249 (8)	0.0224 (8)	0.0221 (8)	−0.0034 (6)	0.0043 (7)	−0.0021 (7)
C13	0.0247 (8)	0.0263 (9)	0.0305 (9)	−0.0070 (7)	−0.0015 (6)	−0.0029 (8)
C14	0.0362 (10)	0.0387 (12)	0.0417 (11)	−0.0130 (9)	0.0037 (9)	0.0028 (10)
C15	0.0392 (10)	0.0399 (12)	0.0509 (12)	0.0020 (11)	−0.0099 (9)	0.0047 (13)
C16	0.0444 (12)	0.0401 (12)	0.0449 (12)	−0.0107 (10)	−0.0001 (10)	−0.0170 (10)
N4	0.0195 (6)	0.0196 (7)	0.0198 (6)	−0.0007 (5)	0.0024 (5)	0.0007 (6)
N5	0.0233 (7)	0.0232 (8)	0.0224 (7)	−0.0037 (5)	0.0085 (5)	−0.0045 (6)
O1	0.0457 (7)	0.0380 (7)	0.0302 (6)	−0.0112 (6)	−0.0146 (5)	0.0006 (6)
O2	0.0244 (6)	0.0374 (7)	0.0288 (6)	0.0055 (5)	0.0010 (5)	0.0039 (6)
O3	0.0289 (6)	0.0412 (8)	0.0314 (6)	−0.0025 (6)	0.0123 (5)	0.0070 (6)
O4	0.0303 (6)	0.0271 (6)	0.0276 (6)	−0.0039 (5)	0.0115 (5)	−0.0065 (5)
O5	0.0344 (7)	0.0383 (7)	0.0434 (7)	−0.0141 (6)	0.0215 (6)	−0.0144 (6)
O6	0.0241 (6)	0.0278 (7)	0.0333 (6)	−0.0073 (5)	0.0070 (4)	−0.0097 (5)
S1	0.02896 (19)	0.01926 (18)	0.0275 (2)	0.00013 (19)	−0.00258 (14)	−0.0033 (2)

Geometric parameters (Å, º)

C2—C3	1.536 (3)	C11—H111	0.99 (3)
C2—S1	1.8198 (18)	C11—H112	0.98 (2)
C2—H21	0.96 (2)	C11—H113	1.00 (3)
C2—H22	0.94 (3)	C12—O5	1.202 (2)
C3—N4	1.462 (2)	C12—O6	1.339 (2)
C3—C10	1.525 (2)	C12—N5	1.378 (2)
C3—H3	0.992 (18)	C13—O6	1.4793 (19)
C5—O4	1.2373 (18)	C13—C14	1.512 (3)
C5—N4	1.375 (2)	C13—C16	1.515 (3)
C5—C6	1.457 (2)	C13—C15	1.516 (3)
C6—C7	1.365 (2)	C14—H141	0.96 (3)
C6—N5	1.394 (2)	C14—H142	0.99 (3)
C7—C8	1.415 (3)	C14—H143	0.93 (3)
C7—H7	0.959 (18)	C15—H151	0.97 (3)
C8—C9	1.350 (2)	C15—H152	0.97 (3)
C8—H8	0.89 (2)	C15—H153	0.99 (2)
C9—N4	1.373 (2)	C16—H161	1.02 (3)
C9—S1	1.7865 (17)	C16—H162	1.05 (3)
C10—O2	1.1986 (18)	C16—H163	0.96 (3)
C10—O3	1.331 (2)	N5—H5	0.87 (2)
C11—O3	1.453 (2)	O1—S1	1.4864 (13)
C3—C2—S1	111.27 (13)	O5—C12—N5	124.90 (15)
C3—C2—H21	109.8 (16)	O6—C12—N5	108.18 (14)
S1—C2—H21	102.9 (13)	O6—C13—C14	111.67 (14)
C3—C2—H22	111.3 (14)	O6—C13—C16	101.35 (14)
S1—C2—H22	107.4 (14)	C14—C13—C16	111.44 (18)
H21—C2—H22	114 (2)	O6—C13—C15	108.79 (16)
N4—C3—C10	108.75 (12)	C14—C13—C15	111.83 (18)
N4—C3—C2	106.94 (13)	C16—C13—C15	111.28 (18)
C10—C3—C2	110.11 (14)	C13—C14—H141	112.6 (18)
N4—C3—H3	109.6 (10)	C13—C14—H142	109.4 (13)
C10—C3—H3	110.1 (10)	H141—C14—H142	102 (2)
C2—C3—H3	111.2 (10)	C13—C14—H143	107.8 (17)
O4—C5—N4	120.76 (14)	H141—C14—H143	113 (2)
O4—C5—C6	124.23 (16)	H142—C14—H143	112 (2)
N4—C5—C6	115.01 (13)	C13—C15—H151	111.7 (16)
C7—C6—N5	127.08 (15)	C13—C15—H152	111.2 (15)
C7—C6—C5	120.92 (15)	H151—C15—H152	106 (2)
N5—C6—C5	111.99 (13)	C13—C15—H153	108.5 (15)
C6—C7—C8	120.41 (15)	H151—C15—H153	107 (2)
C6—C7—H7	119.5 (11)	H152—C15—H153	112 (2)
C8—C7—H7	120.1 (11)	C13—C16—H161	112.0 (16)
C9—C8—C7	118.93 (15)	C13—C16—H162	108.8 (16)
C9—C8—H8	119.8 (13)	H161—C16—H162	108 (2)
C7—C8—H8	121.3 (13)	C13—C16—H163	110.7 (15)
C8—C9—N4	120.91 (15)	H161—C16—H163	106 (2)
C8—C9—S1	125.81 (13)	H162—C16—H163	111 (2)
N4—C9—S1	113.15 (11)	C9—N4—C5	123.76 (13)
O2—C10—O3	125.41 (15)	C9—N4—C3	117.54 (13)
O2—C10—C3	124.25 (15)	C5—N4—C3	118.68 (12)
O3—C10—C3	110.30 (13)	C12—N5—C6	126.10 (14)
O3—C11—H111	107.3 (17)	C12—N5—H5	115.8 (14)
O3—C11—H112	107.3 (12)	C6—N5—H5	117.6 (14)
H111—C11—H112	113 (2)	C10—O3—C11	115.48 (14)
O3—C11—H113	110.1 (14)	C12—O6—C13	121.30 (13)
H111—C11—H113	112 (2)	O1—S1—C9	107.25 (8)
H112—C11—H113	108 (2)	O1—S1—C2	107.93 (9)
O5—C12—O6	126.91 (15)	C9—S1—C2	90.29 (8)
S1—C2—C3—N4	−7.34 (17)	C6—C5—N4—C3	179.01 (12)
S1—C2—C3—C10	−125.34 (13)	C10—C3—N4—C9	120.70 (15)
O4—C5—C6—C7	−178.26 (15)	C2—C3—N4—C9	1.82 (18)
N4—C5—C6—C7	1.5 (2)	C10—C3—N4—C5	−60.81 (17)
O4—C5—C6—N5	0.9 (2)	C2—C3—N4—C5	−179.69 (14)
N4—C5—C6—N5	−179.31 (12)	O5—C12—N5—C6	2.7 (3)
N5—C6—C7—C8	−179.33 (15)	O6—C12—N5—C6	−177.16 (14)
C5—C6—C7—C8	−0.3 (2)	C7—C6—N5—C12	−15.0 (3)
C6—C7—C8—C9	0.0 (2)	C5—C6—N5—C12	165.92 (15)
C7—C8—C9—N4	−1.0 (2)	O2—C10—O3—C11	6.0 (3)
C7—C8—C9—S1	174.65 (12)	C3—C10—O3—C11	−176.24 (17)
N4—C3—C10—O2	−32.2 (2)	O5—C12—O6—C13	−17.2 (2)
C2—C3—C10—O2	84.67 (19)	N5—C12—O6—C13	162.63 (14)
N4—C3—C10—O3	150.01 (14)	C14—C13—O6—C12	63.9 (2)
C2—C3—C10—O3	−93.12 (16)	C16—C13—O6—C12	−177.38 (15)
C8—C9—N4—C5	2.4 (2)	C15—C13—O6—C12	−60.0 (2)
S1—C9—N4—C5	−173.72 (11)	C8—C9—S1—O1	−74.60 (16)
C8—C9—N4—C3	−179.17 (14)	N4—C9—S1—O1	101.31 (12)
S1—C9—N4—C3	4.69 (16)	C8—C9—S1—C2	176.50 (16)
O4—C5—N4—C9	177.21 (14)	N4—C9—S1—C2	−7.59 (13)
C6—C5—N4—C9	−2.6 (2)	C3—C2—S1—O1	−99.79 (14)
O4—C5—N4—C3	−1.2 (2)	C3—C2—S1—C9	8.47 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O2^i	0.87 (2)	2.37 (2)	3.1970 (19)	158.4 (18)
N5—H5···O4	0.87 (2)	2.31 (2)	2.6885 (17)	106.2 (17)
C2—H22···O4^ii	0.94 (3)	2.48 (3)	3.387 (3)	162.3 (19)
C3—H3···O1^iii	0.992 (18)	2.535 (17)	3.142 (2)	119.3 (12)
C7—H7···O5	0.959 (18)	2.332 (18)	2.907 (2)	117.9 (13)
C8—H8···O5^iv	0.89 (2)	2.47 (2)	3.148 (2)	133.2 (17)
C11—H112···O4^v	0.98 (2)	2.45 (2)	3.428 (2)	179 (2)
C11—H113···O3^v	1.00 (3)	2.59 (3)	3.095 (3)	111.1 (16)
C14—H143···O5	0.93 (3)	2.47 (3)	2.996 (3)	116.3 (18)
C15—H152···O5	0.97 (3)	2.58 (2)	3.119 (3)	115.5 (18)
C16—H163···O2^vi	0.96 (3)	2.54 (3)	3.427 (2)	153 (2)

Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z; (iii) −x+1, y+1/2, −z+1; (iv) −x+2, y−1/2, −z+1; (v) −x+1, y−1/2, −z+2; (vi) −x+2, y+3/2, −z+2.