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Crystals of montanastatin anhydride, C36H60N4O12, were grown from a hexylene glycol solution. A crystallographic twofold axis runs through the centre of the molecule. The aliphatic side chains located on one side of the peptide ring form a hydrophobic region. The shape of the whole molecule is rectangular and is similar to the structure of the valinomycin analogue, viz. cyclo[-(D-Val-L-Hyv-L-Val-D-Hyv)2-].
Supporting information
CCDC reference: 193781
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.049
- wR factor = 0.111
- Data-to-parameter ratio = 19.5
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.854 0.982
Tmin' and Tmax expected: 0.970 0.982
RR' = 0.881
Please check that your absorption correction is appropriate.
STRVAL_01
From the CIF: _refine_ls_abs_structure_Flack 0.100
From the CIF: _refine_ls_abs_structure_Flack_su 0.900
Alert C Flack test results are meaningless.
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 28.60
From the CIF: _reflns_number_total 4717
Count of symmetry unique reflns 2805
Completeness (_total/calc) 168.16%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1912
Fraction of Friedel pairs measured 0.682
Are heavy atom types Z>Si present no
ALERT: MoKa measured Friedel data cannot be used to
determine absolute structure in a light-atom
study EXCEPT under VERY special conditions.
It is preferred that Friedel data is merged in such cases.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001); software used to prepare material for publication: PARST (Nardelli, 1995).
Montanastatin:
cyclo(–Val-D-Hyv-D-Val-Lac-)2,
Hyv=alpha-hydroxyisovaleric acid, Lac=lactic acid
top
Crystal data top
C36H60N4O12 | Dx = 1.241 Mg m−3 |
Mr = 740.88 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, C2221 | Cell parameters from 3994 reflections |
a = 13.488 (6) Å | θ = 2.3–28.0° |
b = 17.868 (7) Å | µ = 0.09 mm−1 |
c = 16.452 (7) Å | T = 100 K |
V = 3965 (3) Å3 | Block, colourless |
Z = 4 | 0.32 × 0.24 × 0.20 mm |
F(000) = 1600 | |
Data collection top
Bruker AXS SMART APEX CCD diffractometer | 4717 independent reflections |
Radiation source: MacScience, M18XCE rotating anode | 4545 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
Detector resolution: 8.366 pixels mm-1 | θmax = 28.6°, θmin = 1.9° |
ω scans | h = −17→17 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −15→23 |
Tmin = 0.854, Tmax = 0.982 | l = −22→22 |
13003 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.111 | w = 1/[σ2(Fo2) + (0.0472P)2 + 1.956P] where P = (Fo2 + 2Fc2)/3 |
S = 1.18 | (Δ/σ)max < 0.001 |
4717 reflections | Δρmax = 0.32 e Å−3 |
242 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Absolute structure: (Flack, 1983), 1912 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.1 (9) |
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 | x | y | z | Uiso*/Ueq | |
ON_4 | 0.75840 (10) | 0.75068 (8) | 0.64983 (7) | 0.0171 (3) | |
CA_4 | 0.71119 (15) | 0.77521 (11) | 0.72391 (11) | 0.0182 (4) | |
H1_4 | 0.7622 | 0.7910 | 0.7646 | 0.022* | |
CB_4 | 0.64520 (19) | 0.84027 (12) | 0.70235 (13) | 0.0272 (5) | |
H2_4 | 0.5964 | 0.8244 | 0.6617 | 0.041* | |
H3_4 | 0.6855 | 0.8810 | 0.6801 | 0.041* | |
H4_4 | 0.6107 | 0.8578 | 0.7512 | 0.041* | |
C_4 | 0.65235 (13) | 0.70761 (10) | 0.75589 (11) | 0.0139 (4) | |
O_4 | 0.62526 (11) | 0.65716 (8) | 0.71054 (8) | 0.0187 (3) | |
N_1 | 0.63456 (12) | 0.71050 (9) | 0.83575 (9) | 0.0145 (3) | |
H5_1 | 0.6545 | 0.7501 | 0.8630 | 0.017* | |
CA_1 | 0.58414 (13) | 0.65153 (10) | 0.87941 (10) | 0.0125 (4) | |
H6_1 | 0.5427 | 0.6227 | 0.8399 | 0.015* | |
CB_1 | 0.65766 (14) | 0.59673 (11) | 0.92044 (12) | 0.0158 (4) | |
H7_1 | 0.6186 | 0.5624 | 0.9563 | 0.019* | |
CG1_1 | 0.73278 (15) | 0.63802 (13) | 0.97357 (12) | 0.0212 (4) | |
H8_1 | 0.7744 | 0.6701 | 0.9393 | 0.032* | |
H9_1 | 0.7746 | 0.6016 | 1.0020 | 0.032* | |
H10_1 | 0.6976 | 0.6689 | 1.0134 | 0.032* | |
CG2_1 | 0.71070 (16) | 0.54893 (12) | 0.85690 (13) | 0.0228 (4) | |
H11_1 | 0.7527 | 0.5119 | 0.8843 | 0.034* | |
H12_1 | 0.7519 | 0.5811 | 0.8225 | 0.034* | |
H13_1 | 0.6615 | 0.5231 | 0.8232 | 0.034* | |
C_1 | 0.51590 (13) | 0.68775 (11) | 0.94122 (10) | 0.0127 (4) | |
O_1 | 0.51084 (11) | 0.75341 (8) | 0.95480 (8) | 0.0192 (3) | |
ON_2 | 0.46187 (9) | 0.63488 (7) | 0.97993 (7) | 0.0130 (3) | |
CA_2 | 0.40142 (13) | 0.65922 (10) | 1.04793 (10) | 0.0129 (3) | |
H14_2 | 0.4171 | 0.7130 | 1.0587 | 0.015* | |
CB_2 | 0.43088 (14) | 0.61425 (11) | 1.12323 (11) | 0.0149 (4) | |
H15_2 | 0.3845 | 0.6282 | 1.1681 | 0.018* | |
CG1_2 | 0.42158 (16) | 0.53035 (11) | 1.10937 (12) | 0.0215 (4) | |
H16_2 | 0.4730 | 0.5139 | 1.0713 | 0.032* | |
H17_2 | 0.3561 | 0.5191 | 1.0867 | 0.032* | |
H18_2 | 0.4296 | 0.5040 | 1.1612 | 0.032* | |
CG2_2 | 0.53535 (15) | 0.63533 (14) | 1.14983 (12) | 0.0258 (5) | |
H19_2 | 0.5371 | 0.6885 | 1.1645 | 0.039* | |
H20_2 | 0.5818 | 0.6261 | 1.1051 | 0.039* | |
H21_2 | 0.5544 | 0.6050 | 1.1970 | 0.039* | |
C_2 | 0.29184 (13) | 0.65372 (10) | 1.02782 (11) | 0.0131 (3) | |
O_2 | 0.23148 (10) | 0.66612 (8) | 1.08159 (8) | 0.0179 (3) | |
N_3 | 0.26771 (11) | 0.63797 (9) | 0.95056 (9) | 0.0150 (3) | |
H22_3 | 0.3130 | 0.6197 | 0.9176 | 0.018* | |
CA_3 | 0.16727 (13) | 0.65071 (11) | 0.92056 (11) | 0.0159 (4) | |
H23_3 | 0.1337 | 0.6850 | 0.9599 | 0.019* | |
CB_3 | 0.10523 (15) | 0.57892 (12) | 0.91610 (13) | 0.0224 (4) | |
H24_3 | 0.1112 | 0.5540 | 0.9703 | 0.027* | |
CG1_3 | 0.14135 (18) | 0.52245 (14) | 0.85321 (15) | 0.0321 (5) | |
H25_3 | 0.2139 | 0.5203 | 0.8543 | 0.048* | |
H26_3 | 0.1191 | 0.5378 | 0.7990 | 0.048* | |
H27_3 | 0.1142 | 0.4729 | 0.8659 | 0.048* | |
CG2_3 | −0.00444 (18) | 0.59678 (15) | 0.90426 (16) | 0.0347 (5) | |
H28_3 | −0.0432 | 0.5505 | 0.9078 | 0.052* | |
H29_3 | −0.0143 | 0.6197 | 0.8507 | 0.052* | |
H30_3 | −0.0263 | 0.6316 | 0.9466 | 0.052* | |
C_3 | 0.82219 (14) | 0.69313 (11) | 0.65939 (12) | 0.0172 (4) | |
O_3 | 0.86226 (11) | 0.67840 (9) | 0.72215 (8) | 0.0251 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
ON_4 | 0.0204 (7) | 0.0194 (7) | 0.0114 (6) | −0.0043 (6) | 0.0024 (5) | 0.0013 (6) |
CA_4 | 0.0237 (10) | 0.0203 (9) | 0.0107 (8) | −0.0074 (8) | 0.0026 (7) | −0.0019 (7) |
CB_4 | 0.0399 (13) | 0.0184 (10) | 0.0232 (11) | −0.0028 (9) | 0.0080 (9) | 0.0007 (8) |
C_4 | 0.0111 (8) | 0.0175 (9) | 0.0130 (8) | −0.0014 (7) | −0.0001 (7) | −0.0003 (7) |
O_4 | 0.0223 (7) | 0.0211 (7) | 0.0126 (6) | −0.0090 (6) | 0.0014 (5) | −0.0021 (5) |
N_1 | 0.0175 (7) | 0.0149 (8) | 0.0112 (7) | −0.0053 (6) | 0.0018 (6) | −0.0019 (6) |
CA_1 | 0.0128 (8) | 0.0148 (9) | 0.0098 (8) | −0.0043 (7) | −0.0004 (6) | −0.0003 (7) |
CB_1 | 0.0146 (9) | 0.0163 (9) | 0.0165 (9) | 0.0008 (7) | 0.0014 (7) | 0.0023 (7) |
CG1_1 | 0.0178 (9) | 0.0288 (11) | 0.0170 (9) | 0.0007 (8) | −0.0022 (7) | 0.0013 (8) |
CG2_1 | 0.0227 (10) | 0.0224 (11) | 0.0233 (10) | 0.0051 (8) | 0.0042 (8) | −0.0016 (8) |
C_1 | 0.0122 (9) | 0.0177 (9) | 0.0081 (7) | −0.0026 (7) | −0.0034 (6) | 0.0025 (7) |
O_1 | 0.0235 (7) | 0.0143 (7) | 0.0199 (6) | −0.0041 (6) | 0.0056 (6) | −0.0005 (6) |
ON_2 | 0.0138 (6) | 0.0136 (6) | 0.0117 (6) | −0.0019 (5) | 0.0035 (5) | −0.0006 (5) |
CA_2 | 0.0156 (8) | 0.0139 (9) | 0.0092 (8) | −0.0003 (7) | 0.0033 (7) | −0.0016 (7) |
CB_2 | 0.0142 (9) | 0.0210 (10) | 0.0096 (8) | 0.0014 (7) | 0.0018 (7) | 0.0008 (7) |
CG1_2 | 0.0262 (11) | 0.0191 (10) | 0.0193 (10) | 0.0031 (8) | 0.0023 (8) | 0.0059 (8) |
CG2_2 | 0.0176 (9) | 0.0455 (14) | 0.0143 (9) | −0.0052 (9) | −0.0019 (8) | 0.0001 (9) |
C_2 | 0.0160 (8) | 0.0098 (8) | 0.0136 (8) | 0.0033 (7) | 0.0016 (7) | 0.0002 (7) |
O_2 | 0.0184 (7) | 0.0235 (7) | 0.0117 (6) | 0.0075 (6) | 0.0023 (5) | −0.0009 (5) |
N_3 | 0.0129 (7) | 0.0201 (8) | 0.0121 (7) | 0.0052 (6) | 0.0012 (6) | −0.0012 (6) |
CA_3 | 0.0130 (8) | 0.0221 (10) | 0.0126 (8) | 0.0037 (7) | 0.0010 (7) | −0.0030 (7) |
CB_3 | 0.0204 (10) | 0.0254 (11) | 0.0213 (10) | −0.0008 (8) | −0.0016 (8) | 0.0016 (8) |
CG1_3 | 0.0309 (12) | 0.0277 (12) | 0.0376 (13) | 0.0014 (10) | −0.0079 (10) | −0.0066 (10) |
CG2_3 | 0.0213 (11) | 0.0444 (14) | 0.0384 (13) | −0.0061 (11) | 0.0048 (10) | −0.0116 (11) |
C_3 | 0.0149 (9) | 0.0204 (10) | 0.0163 (9) | −0.0089 (7) | 0.0027 (7) | 0.0022 (8) |
O_3 | 0.0254 (8) | 0.0344 (9) | 0.0154 (7) | −0.0020 (7) | −0.0063 (6) | −0.0009 (6) |
Geometric parameters (Å, º) top
ON_4—C_3 | 1.350 (3) | CA_2—C_2 | 1.518 (3) |
ON_4—CA_4 | 1.443 (2) | CA_2—CB_2 | 1.529 (3) |
CA_4—CB_4 | 1.506 (3) | CB_2—CG1_2 | 1.521 (3) |
CA_4—C_4 | 1.538 (3) | CB_2—CG2_2 | 1.523 (3) |
C_4—O_4 | 1.226 (2) | C_2—O_2 | 1.222 (2) |
C_4—N_1 | 1.336 (2) | C_2—N_3 | 1.342 (2) |
N_1—CA_1 | 1.445 (2) | N_3—CA_3 | 1.460 (2) |
CA_1—C_1 | 1.517 (2) | CA_3—C_3i | 1.525 (3) |
CA_1—CB_1 | 1.548 (3) | CA_3—CB_3 | 1.533 (3) |
CB_1—CG2_1 | 1.528 (3) | CB_3—CG1_3 | 1.525 (3) |
CB_1—CG1_1 | 1.528 (3) | CB_3—CG2_3 | 1.526 (3) |
C_1—O_1 | 1.196 (2) | C_3—O_3 | 1.195 (2) |
C_1—ON_2 | 1.353 (2) | C_3—CA_3i | 1.525 (3) |
ON_2—CA_2 | 1.451 (2) | | |
| | | |
C_3—ON_4—CA_4 | 114.46 (15) | ON_2—CA_2—CB_2 | 108.72 (15) |
ON_4—CA_4—CB_4 | 107.23 (16) | C_2—CA_2—CB_2 | 113.31 (15) |
ON_4—CA_4—C_4 | 106.14 (15) | CG1_2—CB_2—CG2_2 | 111.29 (17) |
CB_4—CA_4—C_4 | 112.43 (17) | CG1_2—CB_2—CA_2 | 112.03 (16) |
O_4—C_4—N_1 | 124.97 (17) | CG2_2—CB_2—CA_2 | 110.08 (16) |
O_4—C_4—CA_4 | 121.54 (17) | O_2—C_2—N_3 | 124.19 (17) |
N_1—C_4—CA_4 | 113.49 (15) | O_2—C_2—CA_2 | 118.62 (16) |
C_4—N_1—CA_1 | 123.02 (15) | N_3—C_2—CA_2 | 117.14 (15) |
N_1—CA_1—C_1 | 107.92 (15) | C_2—N_3—CA_3 | 120.84 (16) |
N_1—CA_1—CB_1 | 112.11 (15) | N_3—CA_3—C_3i | 106.43 (15) |
C_1—CA_1—CB_1 | 111.49 (14) | N_3—CA_3—CB_3 | 113.09 (16) |
CG2_1—CB_1—CG1_1 | 110.54 (17) | C_3i—CA_3—CB_3 | 115.18 (16) |
CG2_1—CB_1—CA_1 | 110.80 (16) | CG1_3—CB_3—CG2_3 | 111.19 (19) |
CG1_1—CB_1—CA_1 | 111.63 (16) | CG1_3—CB_3—CA_3 | 114.31 (18) |
O_1—C_1—ON_2 | 124.50 (17) | CG2_3—CB_3—CA_3 | 111.11 (18) |
O_1—C_1—CA_1 | 125.34 (16) | O_3—C_3—ON_4 | 123.83 (19) |
ON_2—C_1—CA_1 | 110.16 (15) | O_3—C_3—CA_3i | 126.43 (19) |
C_1—ON_2—CA_2 | 117.15 (14) | ON_4—C_3—CA_3i | 109.73 (15) |
ON_2—CA_2—C_2 | 111.08 (14) | | |
| | | |
C_3—On_4—Ca_4—Cb_4 | 178.6 (2) | O_1—C_1—On_2—Ca_2 | −6.5 (3) |
C_3—On_4—Ca_4—C_4 | −61.0 (2) | C_1—On_2—Ca_2—Cb_2 | −123.2 (2) |
Ca_4—On_4—C_3—O_3 | −23.4 (3) | C_1—ON_2—Ca_2—C_2 | 111.4 (2) |
On_4—Ca_4—C_4—O_4 | −23.4 (2) | On_2—Ca_2—Cb_2—Cg1_2 | −56.5 (2) |
ON_4—Ca_4—C_4—N_1 | 156.9 (2) | On_2—Ca_2—Cb_2—Cg2_2 | 67.9 (2) |
Cb_4—Ca_4—C_4—O_4 | 93.5 (2) | C_2—Ca_2—Cb_2—Cg1_2 | 67.6 (2) |
Cb_4—Ca_4—C_4—N_1 | −86.2 (2) | C_2—Ca_2—Cb_2—Cg2_2 | −168.1 (2) |
Ca_4—C_4—N_1—Ca_1 | −177.4 (2) | On_2—Ca_2—C_2—O_2 | 173.7 (2) |
O_4—C_4—N_1—Ca_1 | 3.0 (3) | ON_2—Ca_2—C_2—N_3 | −8.6 (2) |
C_4—N_1—Ca_1—Cb_1 | 96.2 (2) | Cb_2—Ca_2—C_2—O_2 | 51.0 (2) |
C_4—N_1—Ca_1—C_1 | −140.6 (2) | Cb_2—Ca_2—C_2—N_3 | −131.3 (2) |
N_1—Ca_1—Cb_1—Cg1_1 | 53.0 (2) | Ca_2—C_2—N_3—Ca_3 | −163.8 (2) |
N_1—Ca_1—Cb_1—Cg2_1 | −70.7 (2) | O_2—C_2—N_3—Ca_3 | 13.8 (3) |
C_1—Ca_1—Cb_1—Cg1_1 | −68.1 (2) | C_2—N_3—Ca_3—Cb_3 | −101.1 (2) |
C_1—Ca_1—Cb_1—Cg2_1 | 168.2 (2) | N_3—Ca_3—Cb_3—Cg1_3 | −66.7 (2) |
N_1—Ca_1—C_1—O_1 | −4.9 (3) | N_3—Ca_3—Cb_3—Cg2_3 | 166.5 (2) |
N_1—Ca_1—C_1—ON_2 | 175.8 (1) | C_2—N_3—Ca_3—C_3i | 131.6 (2) |
Cb_1—Ca_1—C_1—O_1 | 118.6 (2) | N_3—Ca_3—C_3i—ON_4i | −47.7 (2) |
Cb_1—Ca_1—C_1—On_2 | −60.7 (2) | Ca_3—C_3i—ON_4i—Ca_4i | 155.7 (1) |
Ca_1—C_1—ON_2—Ca_2 | 172.8 (1) | | |
Symmetry code: (i) −x+1, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N_1—H5_1···O_2ii | 0.88 | 2.04 | 2.901 (2) | 167 |
N_3—H22_3···O_4i | 0.88 | 2.36 | 3.037 (2) | 134 |
Symmetry codes: (i) −x+1, y, −z+3/2; (ii) x+1/2, −y+3/2, −z+2. |
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