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The hybrid [beta][gamma] dipeptide, methyl 2-[1-({2-[(tert-but­oxy­carbon­yl)amino]­benzamido}­meth­yl)cyclo­hex­yl]acetate (Boc-Ant-Gpn-OMe), C22H32N2O5, adopts a folded conformation stabilized by intra­molecular six- (C6) and seven-membered (C7) hydrogen-bonded rings, together with weak C-H...O and C-H...[pi] inter­actions, resulting in a ribbon-like structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229613033044/ov3042sup1.cif
Contains datablocks I, New_Global_Publ_Block

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229613033044/ov3042Isup2.hkl
Contains datablock I

CCDC reference: 895752

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Methyl 2-[1-({2-[(tert-butoxycarbonyl)amino]benzamido}methyl)cyclohexyl]acetate top
Crystal data top
C22H32N2O5F(000) = 872
Mr = 404.50Dx = 1.208 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6989 reflections
a = 9.8759 (4) Åθ = 3.7–26.0°
b = 7.8230 (3) ŵ = 0.09 mm1
c = 29.0542 (11) ÅT = 293 K
β = 97.873 (4)°Needle, color less
V = 2223.54 (15) Å30.43 × 0.13 × 0.12 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur Sapphire3
diffractometer
4359 independent reflections
Radiation source: fine-focus sealed tube3091 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
Detector resolution: 16.1049 pixels mm-1θmax = 26.0°, θmin = 3.7°
ω scanh = 1212
Absorption correction: multi-scan
(Crysalis PRO; Oxford Diffraction, 2010)
k = 99
Tmin = 0.91, Tmax = 1.00l = 3435
17649 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0475P)2 + 0.9395P]
where P = (Fo2 + 2Fc2)/3
4359 reflections(Δ/σ)max < 0.001
342 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.17 e Å3
Special details top

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
C10.1776 (4)0.9040 (4)0.21171 (11)0.1092 (12)
H1A0.24900.96920.20070.164*
H1B0.15400.95530.23950.164*
H1C0.09880.90220.18840.164*
C20.1144 (3)0.6167 (5)0.23765 (10)0.0943 (10)
H2A0.03750.61400.21350.141*
H2B0.08710.66590.26520.141*
H2C0.14700.50250.24420.141*
C30.3546 (3)0.7179 (5)0.25656 (9)0.0866 (9)
H3A0.38600.60200.26050.130*
H3B0.33560.76190.28580.130*
H3C0.42400.78640.24540.130*
C40.2267 (2)0.7232 (4)0.22199 (7)0.0612 (6)
O30.25636 (18)0.6651 (2)0.17610 (5)0.0635 (5)
C0'0.2987 (2)0.5042 (3)0.16961 (7)0.0532 (6)
O00.3173 (2)0.3967 (3)0.19927 (6)0.0886 (6)
N10.31740 (19)0.4883 (2)0.12451 (6)0.0490 (5)
C1B0.34934 (19)0.3398 (3)0.10155 (7)0.0427 (5)
C1A0.34359 (18)0.3439 (3)0.05266 (7)0.0408 (5)
C1'0.3091 (2)0.5046 (3)0.02582 (7)0.0431 (5)
O10.2687 (2)0.6351 (2)0.04341 (5)0.0720 (5)
C1B10.3684 (2)0.1914 (3)0.03026 (8)0.0526 (6)
C1G10.3999 (3)0.0420 (3)0.05369 (10)0.0643 (7)
C1G20.4091 (3)0.0416 (3)0.10140 (10)0.0694 (7)
C1B20.3859 (3)0.1875 (3)0.12497 (9)0.0594 (6)
N20.32261 (19)0.5012 (3)0.01931 (6)0.0517 (5)
C2G0.2893 (2)0.6410 (3)0.05152 (7)0.0463 (5)
C2B0.15325 (19)0.6177 (3)0.08359 (6)0.0395 (5)
C2A0.1385 (3)0.4326 (3)0.10203 (9)0.0537 (6)
C2'0.2571 (3)0.3647 (3)0.12313 (8)0.0572 (6)
O20.3632 (2)0.3177 (3)0.10160 (6)0.0918 (7)
C2B10.0318 (2)0.6514 (3)0.05699 (8)0.0497 (5)
C2G10.0179 (3)0.8362 (3)0.04280 (11)0.0685 (7)
C2D0.0112 (4)0.9548 (4)0.08408 (14)0.0886 (10)
C2G20.1342 (3)0.9294 (4)0.10935 (12)0.0789 (8)
C2B20.1478 (3)0.7448 (3)0.12384 (8)0.0584 (6)
O2M0.23481 (17)0.3587 (2)0.16919 (5)0.0710 (5)
C2M0.3453 (3)0.2911 (4)0.19148 (10)0.0931 (10)
H2M10.42360.36430.18510.140*
H2M20.31740.28530.22440.140*
H2M30.36830.17860.17970.140*
H1N0.299 (3)0.581 (3)0.1075 (9)0.070 (8)*
H1B10.362 (2)0.189 (3)0.0043 (9)0.070 (7)*
H1G10.413 (3)0.062 (3)0.0368 (9)0.074 (8)*
H1G20.433 (2)0.063 (3)0.1185 (9)0.075 (8)*
H1B20.388 (2)0.187 (3)0.1576 (9)0.072 (8)*
H2N0.351 (3)0.406 (4)0.0308 (10)0.086 (9)*
H2G10.284 (2)0.748 (3)0.0341 (7)0.048 (6)*
H2G20.367 (2)0.652 (3)0.0715 (7)0.052 (6)*
H2B10.045 (2)0.574 (3)0.0293 (8)0.052 (6)*
H2B20.053 (2)0.614 (3)0.0781 (8)0.063 (7)*
H2G30.062 (3)0.847 (3)0.0276 (9)0.080 (8)*
H2G40.097 (3)0.869 (3)0.0188 (9)0.071 (8)*
H2D20.075 (4)0.924 (4)0.1090 (12)0.119 (12)*
H2D10.003 (3)1.081 (5)0.0741 (11)0.113 (11)*
H2G50.126 (3)1.003 (4)0.1398 (10)0.090 (9)*
H2G60.217 (2)0.958 (3)0.0888 (8)0.054 (6)*
H2B30.227 (2)0.729 (3)0.1394 (8)0.061 (7)*
H2B40.069 (3)0.710 (3)0.1467 (9)0.069 (7)*
H2A10.122 (2)0.355 (3)0.0751 (8)0.055 (6)*
H2A20.058 (2)0.426 (3)0.1235 (8)0.062 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.156 (3)0.106 (3)0.069 (2)0.041 (2)0.028 (2)0.0169 (18)
C20.0696 (17)0.150 (3)0.0669 (19)0.0185 (19)0.0211 (14)0.0221 (19)
C30.0681 (17)0.135 (3)0.0554 (16)0.0007 (17)0.0047 (13)0.0323 (17)
C40.0661 (15)0.0875 (18)0.0314 (12)0.0049 (13)0.0119 (10)0.0109 (11)
O30.0914 (12)0.0714 (11)0.0296 (8)0.0107 (9)0.0147 (8)0.0029 (7)
C0'0.0593 (13)0.0678 (15)0.0324 (12)0.0012 (12)0.0060 (10)0.0018 (11)
O00.1424 (18)0.0868 (13)0.0388 (10)0.0270 (13)0.0206 (10)0.0162 (10)
N10.0660 (12)0.0508 (11)0.0299 (9)0.0009 (9)0.0057 (8)0.0003 (8)
C1B0.0417 (11)0.0497 (12)0.0357 (11)0.0027 (9)0.0021 (8)0.0004 (9)
C1A0.0366 (10)0.0478 (12)0.0367 (11)0.0046 (9)0.0004 (8)0.0028 (9)
C1'0.0482 (11)0.0486 (12)0.0310 (11)0.0069 (10)0.0001 (8)0.0055 (9)
O10.1348 (16)0.0456 (9)0.0351 (8)0.0069 (10)0.0096 (9)0.0025 (7)
C1B10.0578 (13)0.0527 (14)0.0465 (14)0.0019 (10)0.0047 (10)0.0080 (11)
C1G10.0719 (16)0.0507 (15)0.0701 (18)0.0051 (12)0.0088 (13)0.0083 (13)
C1G20.0796 (18)0.0531 (15)0.0743 (19)0.0137 (13)0.0064 (14)0.0116 (14)
C1B20.0682 (15)0.0628 (16)0.0463 (14)0.0070 (12)0.0043 (11)0.0089 (12)
N20.0599 (11)0.0630 (13)0.0321 (10)0.0115 (10)0.0053 (8)0.0009 (9)
C2G0.0453 (11)0.0594 (14)0.0342 (11)0.0073 (10)0.0053 (9)0.0043 (10)
C2B0.0407 (10)0.0478 (11)0.0302 (10)0.0052 (9)0.0060 (8)0.0008 (8)
C2A0.0581 (14)0.0599 (15)0.0438 (13)0.0079 (11)0.0092 (11)0.0090 (11)
C2'0.0681 (15)0.0585 (14)0.0445 (13)0.0058 (12)0.0062 (11)0.0101 (11)
O20.0925 (14)0.1265 (18)0.0541 (11)0.0520 (13)0.0019 (10)0.0150 (11)
C2B10.0439 (12)0.0592 (14)0.0478 (13)0.0065 (10)0.0126 (10)0.0011 (11)
C2G10.0628 (16)0.0646 (17)0.082 (2)0.0021 (13)0.0242 (15)0.0120 (15)
C2D0.092 (2)0.0598 (19)0.114 (3)0.0145 (16)0.016 (2)0.0078 (18)
C2G20.085 (2)0.0676 (18)0.082 (2)0.0067 (16)0.0035 (17)0.0309 (16)
C2B20.0614 (15)0.0755 (17)0.0381 (13)0.0046 (13)0.0063 (12)0.0145 (11)
O2M0.0768 (11)0.0953 (13)0.0405 (9)0.0149 (10)0.0074 (8)0.0120 (9)
C2M0.104 (2)0.122 (3)0.0572 (17)0.031 (2)0.0243 (16)0.0210 (17)
Geometric parameters (Å, º) top
C1—C41.512 (4)N2—C2G1.448 (3)
C1—H1A0.9600N2—H2N0.88 (3)
C1—H1B0.9600C2G—C2B1.537 (3)
C1—H1C0.9600C2G—H2G10.98 (2)
C2—C41.506 (4)C2G—H2G21.03 (2)
C2—H2A0.9600C2B—C2B21.530 (3)
C2—H2B0.9600C2B—C2B11.536 (3)
C2—H2C0.9600C2B—C2A1.545 (3)
C3—C41.503 (3)C2A—C2'1.492 (3)
C3—H3A0.9600C2A—H2A11.02 (2)
C3—H3B0.9600C2A—H2A20.94 (2)
C3—H3C0.9600C2'—O21.202 (3)
C4—O31.475 (2)C2'—O2M1.327 (3)
O3—C0'1.348 (3)C2B1—C2G11.514 (3)
C0'—O01.200 (3)C2B1—H2B11.00 (2)
C0'—N11.354 (3)C2B1—H2B21.01 (2)
N1—C1B1.397 (3)C2G1—C2D1.511 (4)
N1—H1N0.88 (3)C2G1—H2G30.96 (3)
C1B—C1B21.395 (3)C2G1—H2G41.01 (3)
C1B—C1A1.414 (3)C2D—C2G21.516 (4)
C1A—C1B11.397 (3)C2D—H2D21.07 (4)
C1A—C1'1.494 (3)C2D—H2D11.03 (4)
C1'—O11.233 (2)C2G2—C2B21.515 (4)
C1'—N21.336 (3)C2G2—H2G51.05 (3)
C1B1—C1G11.366 (3)C2G2—H2G60.97 (2)
C1B1—H1B11.00 (2)C2B2—H2B30.97 (2)
C1G1—C1G21.377 (4)C2B2—H2B40.99 (3)
C1G1—H1G10.97 (3)O2M—C2M1.443 (3)
C1G2—C1B21.366 (4)C2M—H2M10.9600
C1G2—H1G20.97 (3)C2M—H2M20.9600
C1B2—H1B20.94 (3)C2M—H2M30.9600
C4—C1—H1A109.5C2B—C2G—H2G1108.3 (12)
C4—C1—H1B109.5N2—C2G—H2G2107.9 (12)
H1A—C1—H1B109.5C2B—C2G—H2G2109.1 (12)
C4—C1—H1C109.5H2G1—C2G—H2G2108.1 (16)
H1A—C1—H1C109.5C2B2—C2B—C2G108.82 (17)
H1B—C1—H1C109.5C2B2—C2B—C2B1108.94 (18)
C4—C2—H2A109.5C2G—C2B—C2B1110.65 (17)
C4—C2—H2B109.5C2B2—C2B—C2A110.64 (18)
H2A—C2—H2B109.5C2G—C2B—C2A110.77 (18)
C4—C2—H2C109.5C2B1—C2B—C2A107.00 (17)
H2A—C2—H2C109.5C2'—C2A—C2B115.71 (19)
H2B—C2—H2C109.5C2'—C2A—H2A1108.8 (12)
C4—C3—H3A109.5C2B—C2A—H2A1107.8 (12)
C4—C3—H3B109.5C2'—C2A—H2A2110.4 (14)
H3A—C3—H3B109.5C2B—C2A—H2A2108.1 (14)
C4—C3—H3C109.5H2A1—C2A—H2A2105.5 (18)
H3A—C3—H3C109.5O2—C2'—O2M121.8 (2)
H3B—C3—H3C109.5O2—C2'—C2A124.9 (2)
O3—C4—C3110.03 (19)O2M—C2'—C2A113.3 (2)
O3—C4—C2110.4 (2)C2G1—C2B1—C2B114.01 (19)
C3—C4—C2111.7 (2)C2G1—C2B1—H2B1111.3 (12)
O3—C4—C1101.97 (19)C2B—C2B1—H2B1105.9 (12)
C3—C4—C1112.0 (3)C2G1—C2B1—H2B2109.9 (13)
C2—C4—C1110.3 (3)C2B—C2B1—H2B2106.5 (13)
C0'—O3—C4121.20 (17)H2B1—C2B1—H2B2108.9 (17)
O0—C0'—O125.0 (2)C2D—C2G1—C2B1111.5 (3)
O0—C0'—N1127.1 (2)C2D—C2G1—H2G3111.3 (16)
O3—C0'—N1107.92 (19)C2B1—C2G1—H2G3108.8 (16)
C0'—N1—C1B127.5 (2)C2D—C2G1—H2G4109.8 (14)
C0'—N1—H1N114.9 (16)C2B1—C2G1—H2G4109.8 (14)
C1B—N1—H1N117.3 (16)H2G3—C2G1—H2G4106 (2)
C1B2—C1B—N1122.54 (19)C2G1—C2D—C2G2110.7 (3)
C1B2—C1B—C1A118.8 (2)C2G1—C2D—H2D2110.1 (18)
N1—C1B—C1A118.70 (18)C2G2—C2D—H2D2105.2 (18)
C1B1—C1A—C1B117.59 (19)C2G1—C2D—H2D1111.0 (18)
C1B1—C1A—C1'121.17 (18)C2G2—C2D—H2D1111.1 (18)
C1B—C1A—C1'121.23 (18)H2D2—C2D—H2D1109 (3)
O1—C1'—N2120.3 (2)C2B2—C2G2—C2D111.5 (2)
O1—C1'—C1A122.97 (18)C2B2—C2G2—H2G5106.7 (15)
N2—C1'—C1A116.72 (18)C2D—C2G2—H2G5111.2 (15)
C1G1—C1B1—C1A122.7 (2)C2B2—C2G2—H2G6106.9 (13)
C1G1—C1B1—H1B1117.5 (14)C2D—C2G2—H2G6109.7 (13)
C1A—C1B1—H1B1119.8 (14)H2G5—C2G2—H2G6111 (2)
C1B1—C1G1—C1G2118.9 (2)C2G2—C2B2—C2B113.7 (2)
C1B1—C1G1—H1G1120.2 (15)C2G2—C2B2—H2B3111.1 (14)
C1G2—C1G1—H1G1120.9 (15)C2B—C2B2—H2B3109.2 (14)
C1B2—C1G2—C1G1120.7 (2)C2G2—C2B2—H2B4111.1 (14)
C1B2—C1G2—H1G2119.6 (15)C2B—C2B2—H2B4105.9 (14)
C1G1—C1G2—H1G2119.7 (15)H2B3—C2B2—H2B4105 (2)
C1G2—C1B2—C1B121.3 (2)C2'—O2M—C2M115.7 (2)
C1G2—C1B2—H1B2121.1 (15)O2M—C2M—H2M1109.5
C1B—C1B2—H1B2117.4 (15)O2M—C2M—H2M2109.5
C1'—N2—C2G125.1 (2)H2M1—C2M—H2M2109.5
C1'—N2—H2N118.1 (19)O2M—C2M—H2M3109.5
C2G—N2—H2N116.7 (19)H2M1—C2M—H2M3109.5
N2—C2G—C2B113.88 (17)H2M2—C2M—H2M3109.5
N2—C2G—H2G1109.5 (12)
C3—C4—O3—C0'63.5 (3)O1—C1'—N2—C2G1.9 (3)
C2—C4—O3—C0'60.2 (3)C1A—C1'—N2—C2G177.41 (18)
C1—C4—O3—C0'177.4 (2)C1'—N2—C2G—C2B103.0 (2)
C4—O3—C0'—O00.8 (4)N2—C2G—C2B—C2B2164.82 (19)
C4—O3—C0'—N1179.91 (18)N2—C2G—C2B—C2B175.5 (2)
O0—C0'—N1—C1B6.7 (4)N2—C2G—C2B—C2A43.0 (2)
O3—C0'—N1—C1B173.98 (19)C2B2—C2B—C2A—C2'70.0 (3)
C0'—N1—C1B—C1B29.4 (3)C2G—C2B—C2A—C2'50.8 (3)
C0'—N1—C1B—C1A170.2 (2)C2B1—C2B—C2A—C2'171.4 (2)
C1B2—C1B—C1A—C1B13.2 (3)C2B—C2A—C2'—O276.2 (3)
N1—C1B—C1A—C1B1176.43 (18)C2B—C2A—C2'—O2M104.4 (2)
C1B2—C1B—C1A—C1'178.19 (19)C2B2—C2B—C2B1—C2G151.4 (3)
N1—C1B—C1A—C1'2.2 (3)C2G—C2B—C2B1—C2G168.2 (3)
C1B1—C1A—C1'—O1169.9 (2)C2A—C2B—C2B1—C2G1171.0 (2)
C1B—C1A—C1'—O18.7 (3)C2B—C2B1—C2G1—C2D54.7 (3)
C1B1—C1A—C1'—N29.4 (3)C2B1—C2G1—C2D—C2G255.4 (4)
C1B—C1A—C1'—N2172.02 (18)C2G1—C2D—C2G2—C2B255.7 (4)
C1B—C1A—C1B1—C1G11.2 (3)C2D—C2G2—C2B2—C2B55.3 (3)
C1'—C1A—C1B1—C1G1179.9 (2)C2G—C2B—C2B2—C2G269.2 (3)
C1A—C1B1—C1G1—C1G20.7 (4)C2B1—C2B—C2B2—C2G251.5 (3)
C1B1—C1G1—C1G2—C1B20.6 (4)C2A—C2B—C2B2—C2G2168.9 (2)
C1G1—C1G2—C1B2—C1B1.4 (4)O2—C2'—O2M—C2M0.5 (4)
N1—C1B—C1B2—C1G2176.3 (2)C2A—C2'—O2M—C2M178.9 (2)
C1A—C1B—C1B2—C1G23.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.88 (2)1.89 (3)2.606 (2)137 (2)
N2—H2N···O20.88 (3)2.19 (3)2.863 (3)133 (3)
C1B2—H1B2···O00.95 (3)2.21 (2)2.864 (3)125.6 (18)
C2G—H2G1···O10.98 (2)2.44 (2)2.794 (2)100.5 (15)
C2—H2C···O00.962.412.972 (4)117
C3—H3A···O00.962.423.009 (4)119
C2M—H2M2···O0i0.962.633.474 (3)146
Symmetry code: (i) x, y+1/2, z1/2.
 

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