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The title compound, C22H24INO4, is a chiral reagent developed and used for the synthesis of unnatural amino acids. It forms chains in its crystal structure, via weak N—H...O=C hydrogen bonds. The bulky iodo substituent lies gauche to the two substituents on the neighbouring C atom, about a C—C single bond, rather than gauche to one and trans to the other. This does not seem to be a consequence of any significant intermolecular interactions. The absolute configuration has been confirmed by this experiment and is as expected from the synthesis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803025467/bt6377sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803025467/bt6377Isup2.hkl
Contains datablock I

CCDC reference: 227882

Key indicators

  • Single-crystal X-ray study
  • T = 160 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.026
  • wR factor = 0.051
  • Data-to-parameter ratio = 20.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - C3 = 5.40 su PLAT230_ALERT_2_C Hirshfeld Test Diff for O3 - C8 = 5.26 su PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C8 = 5.20 su
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 28.66 From the CIF: _reflns_number_total 5121 Count of symmetry unique reflns 3152 Completeness (_total/calc) 162.47% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1969 Fraction of Friedel pairs measured 0.625 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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: SMART (Bruker, 2001); cell refinement: local programs; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

tert-Butyl (2R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-iodopropionate top
Crystal data top
C22H24INO4Dx = 1.515 Mg m3
Mr = 493.32Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 9823 reflections
a = 9.2875 (7) Åθ = 2.4–28.6°
b = 12.3181 (9) ŵ = 1.51 mm1
c = 18.9028 (13) ÅT = 160 K
V = 2162.6 (3) Å3Block, colourless
Z = 40.49 × 0.16 × 0.12 mm
F(000) = 992
Data collection top
Bruker SMART 1K CCD
diffractometer
5121 independent reflections
Radiation source: sealed tube4536 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
Detector resolution: 8.192 pixels mm-1θmax = 28.7°, θmin = 2.0°
thin–slice ω scansh = 1112
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
k = 1514
Tmin = 0.667, Tmax = 0.835l = 1725
13825 measured reflections
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)] = 0.026H-atom parameters constrained
wR(F2) = 0.051 w = 1/[σ2(Fo2) + (0.0241P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max = 0.002
5121 reflectionsΔρmax = 0.53 e Å3
256 parametersΔρmin = 0.48 e Å3
0 restraintsAbsolute structure: Flack (1983), 2159 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.027 (12)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.828574 (19)0.054789 (14)0.548113 (9)0.03339 (5)
C10.6013 (3)0.02090 (19)0.55378 (14)0.0259 (5)
H1A0.55960.02410.50560.031*
H1B0.55360.07730.58290.031*
C20.5717 (3)0.09006 (18)0.58564 (13)0.0212 (5)
H20.46460.09810.58820.025*
C30.6280 (3)0.1004 (2)0.66122 (12)0.0213 (5)
O10.70426 (18)0.17296 (14)0.68158 (8)0.0273 (4)
O20.57971 (18)0.01641 (13)0.69861 (8)0.0242 (4)
C40.6154 (3)0.0011 (2)0.77501 (13)0.0245 (6)
C50.5527 (3)0.1102 (2)0.79020 (14)0.0321 (7)
H5A0.45030.11080.77770.048*
H5B0.56360.12680.84060.048*
H5C0.60370.16490.76210.048*
C60.5399 (3)0.0886 (2)0.81728 (13)0.0306 (6)
H6A0.57680.16000.80320.046*
H6B0.55810.07730.86780.046*
H6C0.43610.08530.80820.046*
C70.7776 (3)0.0003 (2)0.78534 (15)0.0315 (7)
H7A0.82200.04720.74990.047*
H7B0.80030.02670.83280.047*
H7C0.81520.07420.78000.047*
N10.6244 (2)0.17903 (15)0.54236 (11)0.0231 (4)
H10.70500.21240.55370.028*
C80.5496 (3)0.21029 (19)0.48489 (12)0.0227 (5)
O30.42824 (18)0.18198 (14)0.47025 (8)0.0284 (4)
O40.62994 (17)0.27758 (13)0.44516 (9)0.0284 (4)
C90.5719 (3)0.3031 (2)0.37576 (12)0.0226 (5)
H9A0.47960.34270.38000.027*
H9B0.55570.23600.34800.027*
C100.6849 (3)0.37328 (18)0.34118 (11)0.0209 (5)
H100.78050.33680.34620.025*
C110.6964 (2)0.48775 (18)0.37084 (12)0.0200 (5)
C120.6864 (2)0.56408 (18)0.31621 (11)0.0185 (4)
C130.6658 (3)0.50630 (18)0.24891 (11)0.0193 (5)
C140.6576 (3)0.39513 (18)0.26291 (11)0.0189 (5)
C150.7107 (2)0.52175 (19)0.44052 (13)0.0228 (6)
H150.71680.47020.47780.027*
C160.7159 (3)0.6322 (2)0.45491 (15)0.0280 (5)
H160.72470.65630.50250.034*
C170.7085 (3)0.7081 (2)0.40037 (13)0.0278 (6)
H170.71290.78340.41110.033*
C180.6946 (3)0.67478 (19)0.33056 (12)0.0239 (5)
H180.69080.72650.29330.029*
C190.6540 (2)0.5454 (2)0.18034 (11)0.0211 (5)
H190.66110.62080.17050.025*
C200.6315 (3)0.4704 (2)0.12645 (12)0.0248 (6)
H200.62400.49520.07900.030*
C210.6197 (3)0.3605 (2)0.14039 (13)0.0268 (6)
H210.60160.31130.10270.032*
C220.6342 (2)0.3212 (2)0.20891 (13)0.0239 (6)
H220.62830.24570.21850.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.02977 (8)0.03313 (9)0.03726 (9)0.00558 (8)0.00197 (8)0.00894 (8)
C10.0219 (12)0.0289 (13)0.0268 (13)0.0033 (10)0.0032 (12)0.0010 (12)
C20.0185 (12)0.0196 (12)0.0255 (13)0.0027 (10)0.0003 (10)0.0026 (10)
C30.0209 (13)0.0211 (12)0.0220 (13)0.0042 (10)0.0050 (10)0.0007 (10)
O10.0340 (11)0.0236 (9)0.0245 (9)0.0097 (8)0.0013 (7)0.0001 (7)
O20.0247 (10)0.0258 (9)0.0221 (9)0.0071 (7)0.0028 (7)0.0057 (7)
C40.0247 (13)0.0295 (14)0.0192 (13)0.0022 (11)0.0014 (11)0.0054 (11)
C50.0296 (16)0.0340 (15)0.0326 (16)0.0048 (12)0.0021 (12)0.0138 (12)
C60.0270 (14)0.0374 (16)0.0274 (14)0.0013 (12)0.0010 (11)0.0010 (11)
C70.0219 (15)0.0317 (14)0.0409 (17)0.0005 (12)0.0028 (12)0.0078 (13)
N10.0240 (10)0.0251 (10)0.0202 (10)0.0049 (8)0.0033 (9)0.0074 (9)
C80.0274 (15)0.0183 (12)0.0225 (13)0.0006 (11)0.0035 (10)0.0018 (10)
O30.0233 (9)0.0325 (10)0.0296 (11)0.0076 (8)0.0053 (7)0.0060 (7)
O40.0301 (10)0.0321 (9)0.0232 (9)0.0096 (7)0.0064 (8)0.0107 (8)
C90.0242 (13)0.0213 (13)0.0222 (13)0.0032 (10)0.0047 (10)0.0050 (10)
C100.0212 (13)0.0203 (12)0.0211 (12)0.0005 (11)0.0011 (11)0.0011 (9)
C110.0145 (13)0.0201 (11)0.0253 (13)0.0018 (9)0.0022 (10)0.0015 (9)
C120.0120 (10)0.0220 (11)0.0215 (11)0.0007 (11)0.0008 (9)0.0009 (10)
C130.0125 (11)0.0227 (11)0.0226 (12)0.0007 (11)0.0019 (11)0.0002 (9)
C140.0145 (12)0.0231 (11)0.0192 (12)0.0006 (10)0.0015 (10)0.0001 (9)
C150.0220 (13)0.0264 (12)0.0198 (13)0.0020 (9)0.0043 (9)0.0021 (9)
C160.0258 (13)0.0338 (14)0.0244 (13)0.0008 (10)0.0041 (12)0.0032 (13)
C170.0323 (16)0.0202 (13)0.0308 (14)0.0022 (11)0.0011 (11)0.0053 (11)
C180.0246 (15)0.0205 (12)0.0265 (13)0.0010 (11)0.0015 (10)0.0044 (10)
C190.0159 (11)0.0241 (12)0.0235 (11)0.0006 (11)0.0009 (9)0.0024 (10)
C200.0219 (13)0.0381 (16)0.0143 (11)0.0006 (10)0.0005 (9)0.0029 (10)
C210.0269 (14)0.0322 (15)0.0212 (13)0.0018 (11)0.0012 (10)0.0068 (11)
C220.0242 (15)0.0208 (13)0.0267 (13)0.0018 (10)0.0010 (10)0.0009 (10)
Geometric parameters (Å, º) top
I1—C12.155 (2)C9—H9A0.990
C1—H1A0.990C9—H9B0.990
C1—H1B0.990C9—C101.509 (3)
C1—C21.519 (3)C10—H101.000
C2—H21.000C10—C111.521 (3)
C2—C31.527 (3)C10—C141.525 (3)
C2—N11.453 (3)C11—C121.400 (3)
C3—O11.203 (3)C11—C151.388 (3)
C3—O21.331 (3)C12—C131.470 (3)
O2—C41.494 (3)C12—C181.392 (3)
C4—C51.517 (3)C13—C141.397 (3)
C4—C61.514 (4)C13—C191.387 (3)
C4—C71.520 (4)C14—C221.385 (3)
C5—H5A0.980C15—H150.950
C5—H5B0.980C15—C161.388 (4)
C5—H5C0.980C16—H160.950
C6—H6A0.980C16—C171.394 (4)
C6—H6B0.980C17—H170.950
C6—H6C0.980C17—C181.388 (3)
C7—H7A0.980C18—H180.950
C7—H7B0.980C19—H190.950
C7—H7C0.980C19—C201.391 (3)
N1—H10.880C20—H200.950
N1—C81.346 (3)C20—C211.384 (4)
C8—O31.212 (3)C21—H210.950
C8—O41.345 (3)C21—C221.389 (3)
O4—C91.452 (3)C22—H220.950
I1—C1—H1A109.3O4—C9—H9B110.8
I1—C1—H1B109.3O4—C9—C10104.91 (19)
I1—C1—C2111.81 (16)H9A—C9—H9B108.8
H1A—C1—H1B107.9H9A—C9—C10110.8
H1A—C1—C2109.3H9B—C9—C10110.8
H1B—C1—C2109.3C9—C10—H10108.6
C1—C2—H2106.7C9—C10—C11114.9 (2)
C1—C2—C3112.58 (19)C9—C10—C14114.0 (2)
C1—C2—N1113.24 (19)H10—C10—C11108.6
H2—C2—C3106.7H10—C10—C14108.6
H2—C2—N1106.7C11—C10—C14101.87 (18)
C3—C2—N1110.4 (2)C10—C11—C12110.24 (19)
C2—C3—O1124.3 (2)C10—C11—C15129.5 (2)
C2—C3—O2108.4 (2)C12—C11—C15120.2 (2)
O1—C3—O2127.3 (2)C11—C12—C13108.8 (2)
C3—O2—C4122.46 (19)C11—C12—C18120.7 (2)
O2—C4—C5102.2 (2)C13—C12—C18130.5 (2)
O2—C4—C6108.5 (2)C12—C13—C14108.52 (19)
O2—C4—C7110.2 (2)C12—C13—C19130.6 (2)
C5—C4—C6111.5 (2)C14—C13—C19120.9 (2)
C5—C4—C7110.5 (2)C10—C14—C13110.35 (19)
C6—C4—C7113.3 (2)C10—C14—C22128.7 (2)
C4—C5—H5A109.5C13—C14—C22120.9 (2)
C4—C5—H5B109.5C11—C15—H15120.5
C4—C5—H5C109.5C11—C15—C16119.0 (2)
H5A—C5—H5B109.5H15—C15—C16120.5
H5A—C5—H5C109.5C15—C16—H16119.6
H5B—C5—H5C109.5C15—C16—C17120.7 (3)
C4—C6—H6A109.5H16—C16—C17119.6
C4—C6—H6B109.5C16—C17—H17119.7
C4—C6—H6C109.5C16—C17—C18120.6 (2)
H6A—C6—H6B109.5H17—C17—C18119.7
H6A—C6—H6C109.5C12—C18—C17118.7 (2)
H6B—C6—H6C109.5C12—C18—H18120.7
C4—C7—H7A109.5C17—C18—H18120.7
C4—C7—H7B109.5C13—C19—H19121.1
C4—C7—H7C109.5C13—C19—C20117.8 (2)
H7A—C7—H7B109.5H19—C19—C20121.1
H7A—C7—H7C109.5C19—C20—H20119.3
H7B—C7—H7C109.5C19—C20—C21121.5 (2)
C2—N1—H1120.1H20—C20—C21119.3
C2—N1—C8119.8 (2)C20—C21—H21119.7
H1—N1—C8120.1C20—C21—C22120.7 (2)
N1—C8—O3125.6 (2)H21—C21—C22119.7
N1—C8—O4109.9 (2)C14—C22—C21118.3 (2)
O3—C8—O4124.5 (2)C14—C22—H22120.9
C8—O4—C9115.59 (19)C21—C22—H22120.9
O4—C9—H9A110.8
I1—C1—C2—C361.0 (2)C15—C11—C12—C181.9 (3)
I1—C1—C2—N165.1 (2)C11—C12—C13—C142.3 (3)
C1—C2—C3—O1128.3 (2)C11—C12—C13—C19178.0 (3)
C1—C2—C3—O251.1 (2)C18—C12—C13—C14176.9 (3)
N1—C2—C3—O10.6 (3)C18—C12—C13—C192.7 (5)
N1—C2—C3—O2178.76 (18)C12—C13—C14—C104.6 (3)
C2—C3—O2—C4179.77 (19)C12—C13—C14—C22178.2 (2)
O1—C3—O2—C40.4 (4)C19—C13—C14—C10175.7 (2)
C3—O2—C4—C5173.2 (2)C19—C13—C14—C221.5 (4)
C3—O2—C4—C668.9 (3)C9—C10—C14—C13129.2 (2)
C3—O2—C4—C755.7 (3)C9—C10—C14—C2253.9 (3)
C1—C2—N1—C878.1 (3)C11—C10—C14—C134.8 (3)
C3—C2—N1—C8154.7 (2)C11—C10—C14—C22178.3 (2)
C2—N1—C8—O311.7 (4)C10—C11—C15—C16178.5 (2)
C2—N1—C8—O4167.77 (19)C12—C11—C15—C160.5 (3)
N1—C8—O4—C9170.05 (19)C11—C15—C16—C170.6 (4)
O3—C8—O4—C99.4 (3)C15—C16—C17—C180.5 (4)
C8—O4—C9—C10176.84 (19)C16—C17—C18—C120.9 (4)
O4—C9—C10—C1172.3 (2)C11—C12—C18—C172.0 (4)
O4—C9—C10—C14170.72 (18)C13—C12—C18—C17177.2 (2)
C9—C10—C11—C12127.1 (2)C12—C13—C19—C20178.6 (2)
C9—C10—C11—C1551.1 (4)C14—C13—C19—C201.0 (4)
C14—C10—C11—C123.4 (3)C13—C19—C20—C210.6 (4)
C14—C10—C11—C15174.8 (2)C19—C20—C21—C221.8 (4)
C10—C11—C12—C130.9 (3)C10—C14—C22—C21176.4 (2)
C10—C11—C12—C18179.8 (2)C13—C14—C22—C210.2 (4)
C15—C11—C12—C13177.5 (2)C20—C21—C22—C141.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.882.493.309 (3)155
Symmetry code: (i) x+1/2, y+1/2, z+1.
 

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