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The title compound, C18H31Cl3N2O5, an enanti­opure dipeptide trichloro­ethyl ester, is one of two starting fragments in the synthesis of cyclo­sporin O analogs. In the crystal structure, mol­ecules are linked by N—H...O=C hydrogen bonds, forming a β-spiral assembly along the c axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806017685/ob2017sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806017685/ob2017Isup2.hkl
Contains datablock I

CCDC reference: 611216

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.035
  • wR factor = 0.087
  • Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 5.81 Ratio
Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 36 Perc. PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.47 Ratio PLAT230_ALERT_2_B Hirshfeld Test Diff for C11 - C14 .. 9.00 su PLAT360_ALERT_2_B Short C(sp3)-C(sp3) Bond C33 - C35 ... 1.31 Ang.
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for O102 - C15 .. 6.40 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C24 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C42 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT390_ALERT_3_C Deviating Methyl C35 X-C-H Bond Angle ...... 102.00 Deg. PLAT431_ALERT_2_C Short Inter HL..A Contact CL402 .. O301 .. 3.16 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
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 68.21 From the CIF: _reflns_number_total 4352 Count of symmetry unique reflns 2225 Completeness (_total/calc) 195.60% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2127 Fraction of Friedel pairs measured 0.956 Are heavy atom types Z>Si present yes
1 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 8 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 8 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2003); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku, 2003); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP (Johnson, 1965); software used to prepare material for publication: CrystalStructure.

tert-Butoxycarbonyl-L-Leucyll-L-Valine Trichloroethyl Ester (Boc-L-Leu-L-Val-OTce) top
Crystal data top
C18H31Cl3N2O5Dx = 1.292 Mg m3
Mr = 461.81Melting point = 377–379 K
Hexagonal, P65Cu Kα radiation, λ = 1.54187 Å
Hall symbol: P 65Cell parameters from 30511 reflections
a = 12.245 (5) Åθ = 4.2–62.2°
c = 27.416 (13) ŵ = 3.75 mm1
V = 3560 (3) Å3T = 173 K
Z = 6Needle, colorless
F(000) = 1464.000.20 × 0.01 × 0.01 mm
? # Insert any comments here.
Data collection top
Rigaku RAXIS-RAPID
diffractometer
Rint = 0.068
Detector resolution: 10.00 pixels mm-1θmax = 68.2°
ω scansh = 1414
32841 measured reflectionsk = 1414
4352 independent reflectionsl = 3232
1558 reflections with F2 > 2σ(F2)
Refinement top
Refinement on F2 w = 4Fo2/[0.0002Fo2 + 0.2σ(Fo2) + 0.1]
R[F2 > 2σ(F2)] = 0.035(Δ/σ)max < 0.001
wR(F2) = 0.087Δρmax = 1.17 e Å3
S = 0.97Δρmin = 0.93 e Å3
4352 reflectionsAbsolute structure: Flack (1983), 2123 Friedel pairs
285 parametersAbsolute structure parameter: 0.015 (15)
All H-atom parameters refined
Special details top

Experimental. ? #Insert any special details here.

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl4010.60861 (13)0.20699 (12)0.86581 (6)0.0852 (5)
Cl4020.83672 (13)0.44215 (12)0.85070 (5)0.0745 (4)
Cl4030.81787 (13)0.28960 (12)0.93194 (6)0.0891 (5)
O1011.1143 (2)1.2369 (2)0.87504 (9)0.0424 (8)
O1021.0485 (2)1.1818 (2)0.95364 (10)0.0553 (9)
O2010.8629 (2)0.8101 (2)0.88992 (9)0.0453 (9)
O3010.6407 (2)0.5842 (2)0.95051 (12)0.0569 (10)
O4010.7734 (2)0.5107 (2)0.94583 (11)0.0587 (10)
N2010.9319 (2)1.0687 (2)0.88961 (11)0.0360 (9)
N3010.8433 (3)0.8209 (3)0.97106 (11)0.0365 (10)
C111.2240 (4)1.3582 (4)0.88841 (17)0.0483 (14)
C121.1798 (4)1.4409 (4)0.9101 (2)0.0814 (19)
C131.2840 (4)1.4074 (4)0.83940 (18)0.0781 (18)
C141.3115 (4)1.3405 (4)0.92183 (17)0.0790 (19)
C151.0329 (3)1.1647 (3)0.91022 (16)0.0378 (13)
C210.8321 (3)0.9759 (3)0.91912 (12)0.0369 (12)
C220.8470 (3)0.8621 (3)0.92579 (14)0.0333 (12)
C230.7060 (3)0.9347 (3)0.89579 (13)0.0412 (13)
C240.5939 (4)0.8571 (4)0.92894 (17)0.0529 (14)
C250.5827 (4)0.9388 (4)0.96814 (16)0.0679 (18)
C260.4744 (4)0.7954 (5)0.8980 (2)0.111 (2)
C310.8525 (4)0.7096 (4)0.97878 (16)0.0475 (15)
C320.7423 (5)0.5990 (4)0.95651 (16)0.0470 (15)
C330.8691 (6)0.6886 (5)1.0327 (2)0.103 (2)
C340.9849 (5)0.7957 (5)1.0538 (2)0.112 (2)
C350.7698 (7)0.6264 (7)1.0607 (2)0.193 (3)
C410.6773 (4)0.3997 (4)0.92419 (18)0.0642 (18)
C420.7343 (4)0.3390 (4)0.89523 (18)0.0587 (16)
H1211.24891.51770.91910.090*
H1221.13271.45420.88610.090*
H1231.12991.40290.93800.090*
H1311.30511.35160.82480.079*
H1321.22731.41610.81900.079*
H1331.35641.48560.84350.079*
H1411.27311.30910.95250.083*
H1421.33211.28420.90730.083*
H1431.38451.41800.92650.082*
H2010.92621.06140.85500.038*
H2110.83491.01030.95040.041*
H2310.70331.00630.88610.047*
H2320.69870.88670.86780.047*
H2410.60380.79430.94410.060*
H2510.65540.97520.98750.082*
H2520.57281.00180.95320.082*
H2530.51320.88940.98820.082*
H2610.46410.85790.88270.118*
H2620.48130.74490.87370.118*
H2630.40500.74630.91820.118*
H3010.83570.86400.99820.041*
H3110.92220.72090.96060.057*
H3310.89160.62661.03060.099*
H3411.00250.77571.08510.128*
H3421.05390.81981.03290.128*
H3430.96830.86171.05670.127*
H3510.74220.68431.06420.170*
H3520.70650.55301.04620.170*
H3530.78940.60771.09200.170*
H4110.62760.34460.94920.077*
H4120.62740.41810.90360.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl4010.1034 (11)0.0575 (8)0.0906 (10)0.0371 (8)0.0058 (9)0.0151 (7)
Cl4020.0947 (10)0.0741 (9)0.0612 (7)0.0470 (8)0.0238 (7)0.0145 (7)
Cl4030.1223 (13)0.0673 (9)0.0902 (10)0.0568 (9)0.0098 (9)0.0100 (8)
O1010.0398 (17)0.0307 (17)0.0330 (15)0.0003 (14)0.0011 (14)0.0010 (13)
O1020.056 (2)0.052 (2)0.0266 (17)0.0036 (17)0.0074 (14)0.0023 (16)
O2010.068 (2)0.0373 (17)0.0338 (15)0.0282 (16)0.0124 (15)0.0013 (14)
O3010.039 (2)0.0407 (19)0.081 (2)0.0129 (17)0.0064 (18)0.0004 (16)
O4010.062 (2)0.050 (2)0.066 (2)0.0284 (19)0.0020 (17)0.0130 (17)
N2010.043 (2)0.0240 (18)0.0272 (18)0.0060 (17)0.0028 (17)0.0016 (15)
N3010.048 (2)0.035 (2)0.0215 (17)0.0165 (18)0.0056 (16)0.0021 (16)
C110.036 (2)0.035 (2)0.053 (3)0.003 (2)0.003 (2)0.002 (2)
C120.063 (3)0.031 (2)0.130 (5)0.009 (2)0.007 (3)0.019 (3)
C130.063 (3)0.060 (3)0.074 (3)0.003 (3)0.006 (3)0.005 (2)
C140.050 (3)0.069 (3)0.087 (4)0.007 (2)0.001 (3)0.003 (3)
C150.037 (2)0.029 (2)0.042 (2)0.012 (2)0.000 (2)0.007 (2)
C210.043 (2)0.033 (2)0.027 (2)0.013 (2)0.008 (2)0.0028 (19)
C220.034 (2)0.026 (2)0.033 (2)0.010 (2)0.011 (2)0.001 (2)
C230.041 (2)0.033 (2)0.043 (2)0.013 (2)0.006 (2)0.001 (2)
C240.045 (2)0.037 (2)0.068 (3)0.015 (2)0.013 (2)0.008 (2)
C250.066 (3)0.071 (3)0.067 (3)0.034 (3)0.022 (2)0.004 (3)
C260.044 (3)0.129 (5)0.121 (5)0.014 (3)0.009 (3)0.008 (4)
C310.047 (3)0.045 (3)0.050 (3)0.023 (2)0.007 (2)0.013 (2)
C320.050 (3)0.042 (3)0.044 (2)0.019 (2)0.012 (2)0.011 (2)
C330.109 (5)0.057 (4)0.080 (4)0.004 (3)0.034 (4)0.027 (3)
C340.129 (5)0.063 (3)0.127 (5)0.035 (4)0.067 (4)0.006 (3)
C350.200 (8)0.170 (8)0.054 (4)0.024 (6)0.010 (5)0.019 (5)
C410.076 (3)0.048 (3)0.068 (3)0.030 (3)0.009 (3)0.014 (2)
C420.076 (3)0.047 (3)0.050 (2)0.029 (2)0.010 (2)0.006 (2)
Geometric parameters (Å, º) top
Cl401—C421.773 (4)C12—H1210.932
Cl402—C421.753 (4)C12—H1220.940
Cl403—C421.744 (6)C12—H1230.944
O101—C111.466 (4)C13—H1310.934
O101—C151.351 (4)C13—H1320.938
O102—C151.207 (5)C13—H1330.931
O201—C221.239 (5)C14—H1410.947
O301—C321.175 (7)C14—H1420.934
O401—C321.346 (8)C14—H1430.931
O401—C411.409 (4)C21—H2110.947
N201—C151.332 (4)C23—H2310.932
N201—C211.432 (4)C23—H2320.944
N301—C221.332 (5)C24—H2410.934
N301—C311.439 (7)C25—H2510.937
C11—C121.489 (8)C25—H2520.934
C11—C131.505 (6)C25—H2530.937
C11—C141.506 (7)C26—H2610.934
C21—C221.505 (7)C26—H2620.941
C21—C231.506 (5)C26—H2630.937
C23—C241.519 (5)C31—H3110.936
C24—C251.520 (7)C33—H3310.930
C24—C261.525 (6)C34—H3410.948
C31—C321.483 (5)C34—H3420.938
C31—C331.531 (7)C34—H3430.930
C33—C341.485 (7)C35—H3510.931
C33—C351.312 (9)C35—H3520.934
C41—C421.480 (8)C35—H3530.947
N201—H2010.951C41—H4110.941
N301—H3010.943C41—H4120.937
C11—O101—C15119.1 (3)H132—C13—H133109.5
C32—O401—C41115.6 (4)C11—C14—H141110.7
C15—N201—C21120.5 (3)C11—C14—H142108.7
C22—N301—C31119.5 (3)C11—C14—H143109.1
O101—C11—C12109.2 (3)H141—C14—H142110.0
O101—C11—C13101.5 (3)H141—C14—H143108.8
O101—C11—C14111.3 (3)H142—C14—H143109.5
C12—C11—C13110.7 (4)N201—C21—H211109.3
C12—C11—C14112.5 (4)C22—C21—H211107.9
C13—C11—C14111.1 (4)C23—C21—H211109.7
O101—C15—O102126.1 (3)C21—C23—H231108.5
O101—C15—N201109.3 (3)C21—C23—H232108.4
O102—C15—N201124.6 (3)C24—C23—H231108.2
N201—C21—C22110.6 (3)C24—C23—H232108.9
N201—C21—C23110.6 (3)H231—C23—H232108.5
C22—C21—C23108.7 (3)C23—C24—H241109.4
O201—C22—N301122.0 (4)C25—C24—H241108.6
O201—C22—C21120.2 (3)C26—C24—H241109.1
N301—C22—C21117.8 (3)C24—C25—H251109.7
C21—C23—C24114.2 (3)C24—C25—H252109.0
C23—C24—C25111.2 (3)C24—C25—H253110.0
C23—C24—C26108.7 (3)H251—C25—H252109.9
C25—C24—C26109.8 (5)H251—C25—H253108.3
N301—C31—C32109.7 (4)H252—C25—H253109.9
N301—C31—C33112.3 (4)C24—C26—H261109.4
C32—C31—C33112.4 (3)C24—C26—H262109.9
O301—C32—O401123.2 (3)C24—C26—H263109.1
O301—C32—C31127.5 (5)H261—C26—H262108.3
O401—C32—C31109.2 (5)H261—C26—H263109.9
C31—C33—C34112.1 (4)H262—C26—H263110.2
C31—C33—C35)120.1 (6)N301—C31—H311106.2
C34—C33—C35)118.9 (5)C32—C31—H311105.2
O401—C41—C42109.5 (4)C33—C31—H311110.6
Cl401—C42—Cl402108.8 (2)C31—C33—H331101.1
Cl401—C42—Cl403109.8 (2)C34—C33—H331101.7
Cl401—C42—C41106.8 (3)C35—C33—H33197.4
Cl402—C42—Cl403108.6 (2)C33—C34—H341111.4
Cl402—C42—C41111.0 (3)C33—C34—H342110.7
Cl403—C42—C41111.7 (3)C33—C34—H343105.9
C15—N201—H201119.8H341—C34—H342110.4
C21—N201—H201119.7H341—C34—H343108.9
C22—N301—H301121.2H342—C34—H343109.5
C31—N301—H301119.4C33—C35—H351101.6
C11—C12—H121109.7C33—C35—H352113.0
C11—C12—H122107.6C33—C35—H353113.4
C11—C12—H123110.7H351—C35—H352109.5
H121—C12—H122109.7H351—C35—H353108.9
H121—C12—H123108.6H352—C35—H353110.0
H122—C12—H123110.5O401—C41—H411108.3
C11—C13—H131110.4O401—C41—H412110.6
C11—C13—H132109.7C42—C41—H411109.2
C11—C13—H133109.1C42—C41—H412109.0
H131—C13—H132108.6H411—C41—H412110.2
H131—C13—H133109.5
C11—O101—C15—O1029.9 (8)N201—C21—C23—C24168.2 (4)
C11—O101—C15—N201171.1 (4)C22—C21—C23—C2470.2 (4)
C15—O101—C11—C1261.0 (5)C23—C21—C22—O20170.5 (4)
C15—O101—C11—C13177.9 (4)C23—C21—C22—N301109.8 (3)
C15—O101—C11—C1463.7 (5)C21—C23—C24—C2572.6 (5)
C32—O401—C41—C42154.9 (4)C21—C23—C24—C26166.4 (4)
C41—O401—C32—O3013.3 (6)N301—C31—C32—O30128.3 (6)
C41—O401—C32—C31179.8 (3)N301—C31—C32—O401155.1 (3)
C15—N201—C21—C2296.9 (4)N301—C31—C33—C3459.9 (7)
C15—N201—C21—C23142.6 (4)N301—C31—C33—C3587.0 (7)
C21—N201—C15—O101178.5 (4)C32—C31—C33—C34175.8 (6)
C21—N201—C15—O1020.4 (7)C32—C31—C33—C3537.3 (10)
C22—N301—C31—C3263.9 (4)C33—C31—C32—O30197.5 (6)
C22—N301—C31—C33170.3 (3)C33—C31—C32—O40179.2 (5)
C31—N301—C22—O2012.6 (5)O401—C41—C42—Cl401175.9 (3)
C31—N301—C22—C21177.7 (3)O401—C41—C42—Cl40257.5 (4)
N201—C21—C22—O20151.1 (4)O401—C41—C42—Cl40364.0 (4)
N201—C21—C22—N301128.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N201—H201···O102i0.951.982.902 (4)162
N301—H301···O201ii0.942.012.947 (4)177
Symmetry codes: (i) xy+1, x, z1/6; (ii) y, x+y+1, z+1/6.
 

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