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The title compound, C14H19NO4S, an inter­mediate for the synthesis of the penta­cyclic antitumour alkaloid camptothecin, has been crystallographically characterized. The crystal structure is stabilized by intra- and intermolecular hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805031636/hg6251sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805031636/hg6251Isup2.hkl
Contains datablock I

CCDC reference: 289765

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.048
  • wR factor = 0.088
  • Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.58 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - O1 .. 5.01 su PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - O2 .. 6.57 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C13 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
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 25.00 From the CIF: _reflns_number_total 2652 Count of symmetry unique reflns 1548 Completeness (_total/calc) 171.32% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1104 Fraction of Friedel pairs measured 0.713 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 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 top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

L-1-(p-Tolylsulfonyl)proline ethyl ester top
Crystal data top
C14H19NO4SF(000) = 632
Mr = 297.36Dx = 1.313 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 784 reflections
a = 7.4671 (17) Åθ = 3.0–25.1°
b = 11.547 (3) ŵ = 0.23 mm1
c = 17.445 (4) ÅT = 291 K
V = 1504.1 (6) Å3Plate, colorless
Z = 40.60 × 0.50 × 0.40 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2652 independent reflections
Radiation source: fine-focus sealed tube1855 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.069
φ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 86
Tmin = 0.876, Tmax = 0.915k = 1313
7523 measured reflectionsl = 2020
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.088 w = 1/[σ2(Fo2) + (0.024P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.91(Δ/σ)max < 0.001
2652 reflectionsΔρmax = 0.31 e Å3
183 parametersΔρmin = 0.15 e Å3
7 restraintsAbsolute structure: Flack (1983), 1104 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.08 (10)
Special details top

Experimental. The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses.

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
xyzUiso*/Ueq
C10.4766 (4)0.6102 (3)0.29772 (16)0.0449 (7)
C20.4520 (4)0.5131 (3)0.34185 (18)0.0556 (9)
H20.45220.44020.31920.067*
C30.4269 (4)0.5239 (3)0.4194 (2)0.0635 (11)
H30.41160.45760.44900.076*
C40.4240 (5)0.6301 (4)0.45421 (19)0.0641 (11)
C50.4469 (5)0.7256 (3)0.4092 (2)0.0719 (11)
H50.44490.79850.43200.086*
C60.4728 (5)0.7178 (3)0.33139 (17)0.0582 (9)
H60.48740.78430.30190.070*
C70.4010 (6)0.6413 (4)0.54008 (17)0.1057 (16)
H7A0.32670.57940.55850.159*
H7B0.34560.71420.55170.159*
H7C0.51600.63730.56450.159*
C80.8309 (4)0.4890 (3)0.2233 (2)0.0629 (10)
H8A0.83250.42530.18710.075*
H8B0.77430.46320.27040.075*
C91.0178 (5)0.5330 (3)0.2385 (2)0.0746 (11)
H9A1.09540.51880.19490.090*
H9B1.06890.49640.28350.090*
C100.9911 (5)0.6622 (3)0.25129 (17)0.0717 (10)
H10A0.95210.67780.30330.086*
H10B1.10090.70470.24150.086*
C110.8473 (4)0.6946 (3)0.19404 (17)0.0516 (9)
H110.77790.76130.21200.062*
C120.9287 (5)0.7183 (3)0.11713 (18)0.0553 (9)
C131.0765 (7)0.8578 (4)0.0413 (2)0.1163 (17)
H13A1.19550.82410.04250.140*
H13B1.01390.82740.00310.140*
C141.0899 (5)0.9825 (4)0.0356 (2)0.0970 (15)
H14A1.14521.01260.08110.145*
H14B0.97231.01500.03020.145*
H14C1.16101.00260.00820.145*
N10.7360 (3)0.5908 (2)0.19090 (13)0.0522 (6)
O10.4515 (3)0.49069 (19)0.17390 (11)0.0628 (7)
O20.4681 (4)0.70389 (19)0.16354 (11)0.0652 (7)
O30.9798 (4)0.8272 (2)0.11091 (12)0.0816 (8)
O40.9485 (4)0.6479 (2)0.06845 (12)0.0881 (9)
S10.52168 (11)0.59891 (7)0.19946 (4)0.0508 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0397 (16)0.0361 (18)0.0589 (16)0.0034 (16)0.0039 (16)0.0018 (17)
C20.057 (2)0.042 (2)0.067 (2)0.0052 (18)0.0015 (19)0.0012 (17)
C30.061 (3)0.067 (3)0.062 (2)0.004 (2)0.0054 (19)0.021 (2)
C40.064 (2)0.076 (3)0.053 (2)0.010 (2)0.0014 (17)0.005 (2)
C50.086 (3)0.055 (2)0.075 (2)0.007 (2)0.001 (2)0.016 (2)
C60.069 (3)0.043 (2)0.062 (2)0.009 (2)0.004 (2)0.0013 (17)
C70.119 (4)0.133 (4)0.065 (2)0.016 (3)0.012 (3)0.002 (3)
C80.053 (2)0.055 (2)0.081 (2)0.0111 (19)0.0101 (18)0.005 (2)
C90.063 (3)0.084 (3)0.077 (2)0.004 (2)0.003 (2)0.022 (2)
C100.068 (2)0.091 (3)0.0562 (19)0.020 (2)0.008 (2)0.000 (2)
C110.055 (2)0.050 (2)0.0500 (18)0.0020 (17)0.0047 (18)0.0070 (19)
C120.065 (3)0.049 (2)0.052 (2)0.0045 (18)0.0030 (18)0.0021 (19)
C130.181 (5)0.082 (3)0.086 (3)0.037 (3)0.068 (3)0.001 (2)
C140.098 (3)0.092 (4)0.100 (3)0.004 (3)0.021 (3)0.041 (3)
N10.0524 (16)0.0387 (15)0.0654 (16)0.0018 (15)0.0042 (13)0.0080 (16)
O10.0624 (17)0.0550 (15)0.0711 (14)0.0122 (13)0.0029 (12)0.0162 (12)
O20.0739 (17)0.0593 (15)0.0624 (12)0.0148 (15)0.0080 (13)0.0179 (12)
O30.125 (2)0.0534 (16)0.0667 (14)0.0262 (18)0.0355 (16)0.0023 (12)
O40.138 (2)0.0661 (17)0.0606 (14)0.0221 (18)0.0229 (16)0.0147 (13)
S10.0502 (5)0.0482 (5)0.0540 (4)0.0004 (5)0.0043 (4)0.0002 (5)
Geometric parameters (Å, º) top
C1—C21.372 (4)C9—H9A0.9700
C1—C61.375 (4)C9—H9B0.9700
C1—S11.752 (3)C10—C111.514 (4)
C2—C31.372 (4)C10—H10A0.9700
C2—H20.9300C10—H10B0.9700
C3—C41.368 (5)C11—N11.459 (4)
C3—H30.9300C11—C121.498 (4)
C4—C51.365 (4)C11—H110.9800
C4—C71.513 (4)C12—O41.185 (3)
C5—C61.374 (4)C12—O31.318 (4)
C5—H50.9300C13—C141.446 (4)
C6—H60.9300C13—O31.456 (4)
C7—H7A0.9600C13—H13A0.9700
C7—H7B0.9600C13—H13B0.9700
C7—H7C0.9600C14—H14A0.9600
C8—N11.485 (4)C14—H14B0.9600
C8—C91.509 (5)C14—H14C0.9600
C8—H8A0.9700N1—S11.610 (2)
C8—H8B0.9700O1—S11.426 (2)
C9—C101.522 (4)O2—S11.422 (2)
C2—C1—C6119.7 (3)C11—C10—H10A111.0
C2—C1—S1121.0 (2)C9—C10—H10A111.0
C6—C1—S1119.3 (2)C11—C10—H10B111.0
C3—C2—C1119.9 (3)C9—C10—H10B111.0
C3—C2—H2120.1H10A—C10—H10B109.0
C1—C2—H2120.1N1—C11—C12110.3 (3)
C4—C3—C2121.4 (3)N1—C11—C10103.1 (3)
C4—C3—H3119.3C12—C11—C10110.4 (3)
C2—C3—H3119.3N1—C11—H11110.9
C5—C4—C3117.9 (3)C12—C11—H11110.9
C5—C4—C7121.0 (4)C10—C11—H11110.9
C3—C4—C7121.1 (4)O4—C12—O3124.0 (3)
C4—C5—C6122.2 (3)O4—C12—C11124.6 (3)
C4—C5—H5118.9O3—C12—C11111.4 (3)
C6—C5—H5118.9C14—C13—O3109.5 (3)
C5—C6—C1119.0 (3)C14—C13—H13A109.8
C5—C6—H6120.5O3—C13—H13A109.8
C1—C6—H6120.5C14—C13—H13B109.8
C4—C7—H7A109.5O3—C13—H13B109.8
C4—C7—H7B109.5H13A—C13—H13B108.2
H7A—C7—H7B109.5C13—C14—H14A109.5
C4—C7—H7C109.5C13—C14—H14B109.5
H7A—C7—H7C109.5H14A—C14—H14B109.5
H7B—C7—H7C109.5C13—C14—H14C109.5
N1—C8—C9103.9 (3)H14A—C14—H14C109.5
N1—C8—H8A111.0H14B—C14—H14C109.5
C9—C8—H8A111.0C11—N1—C8111.4 (2)
N1—C8—H8B111.0C11—N1—S1121.0 (2)
C9—C8—H8B111.0C8—N1—S1119.0 (2)
H8A—C8—H8B109.0C12—O3—C13116.4 (3)
C8—C9—C10103.6 (3)O2—S1—O1120.37 (13)
C8—C9—H9A111.0O2—S1—N1106.77 (15)
C10—C9—H9A111.0O1—S1—N1106.57 (14)
C8—C9—H9B111.0O2—S1—C1108.30 (14)
C10—C9—H9B111.0O1—S1—C1107.48 (14)
H9A—C9—H9B109.0N1—S1—C1106.61 (12)
C11—C10—C9103.7 (3)
C6—C1—C2—C31.2 (5)C12—C11—N1—S1111.7 (3)
S1—C1—C2—C3176.3 (2)C10—C11—N1—S1130.5 (2)
C1—C2—C3—C40.7 (5)C9—C8—N1—C116.5 (3)
C2—C3—C4—C50.0 (6)C9—C8—N1—S1154.6 (2)
C2—C3—C4—C7178.5 (3)O4—C12—O3—C134.1 (6)
C3—C4—C5—C60.2 (6)C11—C12—O3—C13174.3 (3)
C7—C4—C5—C6178.3 (4)C14—C13—O3—C12168.1 (4)
C4—C5—C6—C10.3 (6)C11—N1—S1—O235.1 (3)
C2—C1—C6—C51.0 (5)C8—N1—S1—O2179.9 (2)
S1—C1—C6—C5176.5 (3)C11—N1—S1—O1164.9 (2)
N1—C8—C9—C1027.1 (3)C8—N1—S1—O150.1 (3)
C8—C9—C10—C1137.9 (3)C11—N1—S1—C180.5 (2)
C9—C10—C11—N133.4 (3)C8—N1—S1—C164.5 (3)
C9—C10—C11—C1284.4 (4)C2—C1—S1—O2156.1 (3)
N1—C11—C12—O422.0 (5)C6—C1—S1—O226.4 (3)
C10—C11—C12—O491.3 (4)C2—C1—S1—O124.6 (3)
N1—C11—C12—O3159.6 (3)C6—C1—S1—O1157.9 (3)
C10—C11—C12—O387.1 (4)C2—C1—S1—N189.4 (3)
C12—C11—N1—C8100.9 (3)C6—C1—S1—N188.2 (3)
C10—C11—N1—C816.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O20.932.592.933 (4)102
C11—H11···O20.982.552.883 (4)100
C6—H6···O1i0.932.463.202 (4)137
Symmetry code: (i) x+1, y+1/2, z+1/2.
 

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