Iso­propyl 6,7-di­deoxy-1,2:3,4-di-O-iso­propyl­idene-7-{[(S)-1-phenyl­ethyl]­amino}-L-glycero-α-D-galacto-octo­pyran­uronate

The stereochemistry of the new chiral centre C7 in the title galac­tosyl α-amino­ester diastereomer product, C₂₅H₃₇NO₇, has been established as S. The pyran­ose ring has a twist-boat conformation due to the presence of the two iso­propyl­idene ketal moieties. The mol­ecule contains no intramolecular hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• Disorder in main residue
• R factor = 0.047
• wR factor = 0.125
• Data-to-parameter ratio = 11.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_301  Alert C Main Residue Disorder ........................      15.00 Perc.

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           26.96
         From the CIF: _reflns_number_total               3143
         Count of symmetry unique reflns         3145
         Completeness (_total/calc)             99.94%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          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.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

Computing details

Data collection: CAD-4 Operations Manual (Enraf-Nonius, 1977); cell refinement: CAD-4 Operations Manual; data reduction: PROCESS in MolEN (Fair, 1990); program(s) used to solve structure: SIR97 (Altomare et al., 1998); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1998); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

C25H37NO7	Dx = 1.199 Mg m^−3
Mr = 463.56	Mo Kα radiation, λ = 0.71069 Å
Orthorhombic, P212121	Cell parameters from 25 reflections
a = 9.809 (1) Å	θ = 7.5–12.0°
b = 13.978 (5) Å	µ = 0.09 mm^−1
c = 18.730 (2) Å	T = 293 K
V = 2568.1 (10) Å^3	Block, colourless
Z = 4	0.25 × 0.15 × 0.15 mm
F(000) = 1000

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 27.0°, θmin = 2.2°
Graphite monochromator	h = 0→12
ω scans	k = 0→17
3143 measured reflections	l = 0→23
3143 independent reflections	3 standard reflections every 60 min
1782 reflections with I > 2σ(I)	intensity decay: 0.6%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.125	w = 1/[σ^2(Fo^2) + (0.0537P)^2 + 0.5544P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.014
3143 reflections	Δρmax = 0.27 e Å^−3
270 parameters	Δρmin = −0.25 e Å^−3
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.009 (1)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O3	0.3963 (3)	0.56128 (17)	0.75039 (14)	0.0506 (7)
O2	0.2081 (3)	0.7045 (2)	0.62422 (14)	0.0545 (8)
O1	0.3994 (3)	0.7844 (2)	0.59216 (14)	0.0593 (8)
O5	0.4877 (2)	0.75561 (17)	0.70501 (13)	0.0436 (7)
O4	0.3501 (3)	0.66468 (18)	0.84102 (14)	0.0538 (8)
O6	0.4704 (3)	1.00844 (19)	0.93660 (14)	0.0556 (8)
O7	0.4347 (3)	0.85621 (19)	0.96623 (14)	0.0575 (8)
N1	0.2996 (3)	0.9873 (2)	0.81541 (15)	0.0407 (8)
H1A	0.3730	1.0232	0.8022	0.049*
C1	0.4422 (4)	0.7134 (3)	0.64094 (19)	0.0440 (9)
H1	0.5170	0.6767	0.6197	0.053*
C2	0.3190 (4)	0.6488 (3)	0.6495 (2)	0.0422 (9)
H2	0.3295	0.5910	0.6203	0.051*
C3	0.2897 (4)	0.6222 (3)	0.7260 (2)	0.0422 (9)
H3	0.2018	0.5892	0.7293	0.051*
C4	0.2939 (4)	0.7061 (2)	0.77812 (19)	0.0410 (9)
H4	0.2009	0.7281	0.7878	0.049*
C5	0.3796 (3)	0.7900 (2)	0.75029 (19)	0.0366 (8)
H5	0.3208	0.8327	0.7224	0.044*
C6	0.4485 (4)	0.8475 (3)	0.80820 (19)	0.0383 (9)
H6A	0.5131	0.8911	0.7863	0.046*
H6B	0.4995	0.8043	0.8387	0.046*
C7	0.3495 (4)	0.9049 (2)	0.85413 (19)	0.0357 (9)
H7	0.2718	0.8639	0.8661	0.043*
C8	0.4237 (4)	0.9319 (3)	0.9238 (2)	0.0376 (9)
C9	0.5229 (5)	0.8628 (3)	1.0287 (2)	0.0567 (12)
H9	0.5839	0.9179	1.0237	0.068*
C10	0.6047 (5)	0.7726 (4)	1.0303 (3)	0.0841 (16)
H10A	0.6586	0.7681	0.9876	0.101*
H10B	0.5445	0.7186	1.0331	0.101*
H10C	0.6637	0.7731	1.0712	0.101*
C11	0.4348 (6)	0.8756 (4)	1.0933 (2)	0.0915 (18)
H11A	0.3858	0.9348	1.0896	0.110*
H11B	0.4909	0.8767	1.1353	0.110*
H11C	0.3713	0.8235	1.0965	0.110*
C12	0.2631 (5)	0.7642 (3)	0.5694 (2)	0.0607 (12)
C13	0.1834 (6)	0.8552 (4)	0.5671 (3)	0.0960 (18)
H13A	0.2190	0.8958	0.5302	0.115*
H13B	0.1905	0.8872	0.6123	0.115*
H13C	0.0894	0.8411	0.5573	0.115*
C14	0.2652 (6)	0.7127 (4)	0.4982 (2)	0.0863 (18)
H14A	0.3023	0.7542	0.4624	0.104*
H14B	0.1739	0.6949	0.4853	0.104*
H14C	0.3205	0.6562	0.5020	0.104*
C15	0.4041 (5)	0.5718 (3)	0.8259 (2)	0.0541 (11)
C16	0.5500 (5)	0.5676 (4)	0.8482 (3)	0.0891 (18)
H16A	0.5862	0.5053	0.8378	0.107*
H16B	0.5566	0.5797	0.8985	0.107*
H16C	0.6010	0.6151	0.8226	0.107*
C17	0.3160 (7)	0.4977 (3)	0.8622 (3)	0.0886 (18)
H17A	0.3518	0.4351	0.8527	0.106*
H17B	0.2246	0.5020	0.8442	0.106*
H17C	0.3157	0.5090	0.9127	0.106*
C18	0.1842 (4)	1.0374 (3)	0.8483 (2)	0.0466 (10)
H18	0.2082	1.0513	0.8991	0.056*
C19	0.1654 (5)	1.1331 (3)	0.8106 (3)	0.0654 (13)
H19A	0.2486	1.1688	0.8117	0.079*
H19B	0.0936	1.1682	0.8321	0.079*
H19C	0.1424	1.1200	0.7609	0.079*
C20A	0.0615 (5)	0.9842 (4)	0.8559 (3)	0.039 (2)*	0.547 (10)
C21A	−0.0217 (6)	0.9906 (4)	0.9158 (3)	0.060 (2)*	0.547 (10)
H21A	0.0049	1.0279	0.9545	0.072*	0.547 (10)
C22A	−0.1446 (5)	0.9412 (5)	0.9179 (3)	0.075 (3)*	0.547 (10)
H22A	−0.2003	0.9455	0.9580	0.090*	0.547 (10)
C23A	−0.1844 (5)	0.8855 (4)	0.8601 (4)	0.057 (3)*	0.547 (10)
H23A	−0.2667	0.8525	0.8615	0.068*	0.547 (10)
C24A	−0.1013 (6)	0.8791 (4)	0.8002 (3)	0.076 (3)*	0.547 (10)
H24A	−0.1279	0.8418	0.7615	0.091*	0.547 (10)
C25A	0.0217 (5)	0.9285 (4)	0.7981 (3)	0.051 (2)*	0.547 (10)
H25A	0.0774	0.9242	0.7580	0.061*	0.547 (10)
C20B	0.0560 (7)	0.9738 (5)	0.8325 (4)	0.043 (3)*	0.453 (10)
C21B	−0.0427 (8)	0.9658 (6)	0.8855 (4)	0.075 (4)*	0.453 (10)
H21B	−0.0311	0.9972	0.9288	0.090*	0.453 (10)
C22B	−0.1586 (7)	0.9109 (7)	0.8736 (5)	0.101 (5)*	0.453 (10)
H22B	−0.2246	0.9056	0.9090	0.122*	0.453 (10)
C23B	−0.1759 (6)	0.8639 (6)	0.8088 (5)	0.077 (4)*	0.453 (10)
H23B	−0.2535	0.8272	0.8009	0.092*	0.453 (10)
C24B	−0.0772 (7)	0.8719 (5)	0.7559 (4)	0.079 (4)*	0.453 (10)
H24B	−0.0888	0.8405	0.7125	0.095*	0.453 (10)
C25B	0.0387 (7)	0.9269 (6)	0.7677 (4)	0.061 (3)*	0.453 (10)
H25B	0.1047	0.9322	0.7323	0.074*	0.453 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0707 (18)	0.0391 (14)	0.0421 (14)	0.0119 (15)	0.0010 (15)	−0.0011 (13)
O2	0.0522 (17)	0.0550 (17)	0.0564 (17)	0.0035 (16)	−0.0109 (15)	0.0020 (15)
O1	0.076 (2)	0.0549 (17)	0.0474 (16)	−0.0045 (17)	−0.0040 (16)	0.0128 (15)
O5	0.0397 (14)	0.0481 (15)	0.0430 (14)	0.0020 (13)	0.0047 (12)	−0.0072 (13)
O4	0.082 (2)	0.0391 (15)	0.0406 (15)	0.0064 (16)	0.0037 (16)	0.0004 (13)
O6	0.080 (2)	0.0411 (16)	0.0459 (16)	−0.0110 (16)	−0.0114 (16)	0.0032 (14)
O7	0.077 (2)	0.0450 (16)	0.0502 (16)	−0.0168 (17)	−0.0223 (16)	0.0165 (14)
N1	0.0435 (18)	0.0403 (17)	0.0384 (16)	0.0087 (16)	−0.0028 (16)	−0.0018 (15)
C1	0.051 (2)	0.043 (2)	0.038 (2)	0.006 (2)	0.0035 (19)	−0.006 (2)
C2	0.044 (2)	0.038 (2)	0.045 (2)	−0.001 (2)	−0.004 (2)	−0.0060 (19)
C3	0.042 (2)	0.033 (2)	0.051 (2)	−0.0023 (18)	0.002 (2)	−0.0036 (18)
C4	0.043 (2)	0.0348 (19)	0.045 (2)	0.0041 (19)	0.0023 (19)	−0.0044 (18)
C5	0.0356 (19)	0.0309 (18)	0.043 (2)	0.0039 (17)	−0.0001 (18)	0.0013 (19)
C6	0.0357 (19)	0.0336 (19)	0.046 (2)	0.0027 (18)	0.0005 (18)	−0.0027 (18)
C7	0.036 (2)	0.0304 (18)	0.041 (2)	−0.0030 (17)	−0.0011 (18)	0.0013 (17)
C8	0.038 (2)	0.033 (2)	0.042 (2)	−0.0007 (19)	0.0025 (18)	0.0057 (19)
C9	0.069 (3)	0.055 (3)	0.046 (2)	−0.006 (3)	−0.021 (2)	0.008 (2)
C10	0.087 (4)	0.093 (4)	0.072 (3)	0.024 (3)	−0.018 (3)	0.005 (3)
C11	0.124 (5)	0.091 (4)	0.060 (3)	0.015 (4)	−0.006 (3)	−0.003 (3)
C12	0.079 (3)	0.054 (3)	0.049 (3)	0.008 (3)	−0.011 (2)	0.002 (2)
C13	0.120 (5)	0.080 (4)	0.087 (4)	0.033 (4)	−0.022 (4)	0.011 (3)
C14	0.115 (5)	0.096 (4)	0.048 (2)	0.001 (4)	−0.012 (3)	−0.004 (3)
C15	0.074 (3)	0.046 (2)	0.042 (2)	0.015 (2)	0.007 (2)	0.002 (2)
C16	0.088 (4)	0.121 (5)	0.058 (3)	0.037 (4)	−0.018 (3)	−0.014 (3)
C17	0.143 (5)	0.051 (3)	0.071 (3)	0.000 (4)	0.032 (4)	0.012 (3)
C18	0.047 (2)	0.045 (2)	0.048 (2)	0.008 (2)	0.001 (2)	0.002 (2)
C19	0.062 (3)	0.047 (3)	0.088 (3)	0.009 (2)	−0.013 (3)	0.004 (3)

Geometric parameters (Å, º)

O3—C3	1.423 (4)	C9—C10	1.496 (6)
O3—C15	1.423 (5)	C9—C11	1.498 (6)
O2—C2	1.419 (4)	C12—C13	1.495 (6)
O2—C12	1.428 (5)	C12—C14	1.515 (6)
O1—C1	1.412 (5)	C15—C16	1.492 (7)
O1—C12	1.431 (5)	C15—C17	1.510 (6)
O5—C1	1.410 (4)	C18—C20A	1.422 (5)
O5—C5	1.440 (4)	C18—C19	1.525 (5)
O4—C4	1.424 (4)	C18—C20B	1.568 (7)
O4—C15	1.431 (5)	C20A—C21A	1.390
O6—C8	1.189 (4)	C20A—C25A	1.390
O7—C8	1.328 (4)	C21A—C22A	1.390
O7—C9	1.458 (4)	C22A—C23A	1.390
N1—C7	1.446 (4)	C23A—C24A	1.390
N1—C18	1.466 (5)	C24A—C25A	1.390
C1—C2	1.518 (5)	C20B—C21B	1.390
C2—C3	1.507 (5)	C20B—C25B	1.390
C3—C4	1.528 (5)	C21B—C22B	1.390
C4—C5	1.534 (5)	C22B—C23B	1.390
C5—C6	1.509 (5)	C23B—C24B	1.390
C6—C7	1.526 (5)	C24B—C25B	1.390
C7—C8	1.540 (5)
C3—O3—C15	107.3 (3)	O2—C12—C13	108.7 (4)
C2—O2—C12	105.7 (3)	O1—C12—C13	109.2 (4)
C1—O1—C12	109.4 (3)	O2—C12—C14	111.1 (4)
C1—O5—C5	114.1 (3)	O1—C12—C14	110.1 (4)
C4—O4—C15	110.4 (3)	C13—C12—C14	112.7 (4)
C8—O7—C9	118.6 (3)	O3—C15—O4	105.7 (3)
C7—N1—C18	115.5 (3)	O3—C15—C16	109.0 (4)
O5—C1—O1	110.5 (3)	O4—C15—C16	109.5 (4)
O5—C1—C2	114.3 (3)	O3—C15—C17	110.2 (4)
O1—C1—C2	104.5 (3)	O4—C15—C17	108.7 (3)
O2—C2—C3	107.9 (3)	C16—C15—C17	113.3 (4)
O2—C2—C1	104.3 (3)	C20A—C18—N1	116.5 (4)
C3—C2—C1	113.5 (3)	C20A—C18—C19	113.8 (4)
O3—C3—C2	108.2 (3)	N1—C18—C19	108.5 (3)
O3—C3—C4	103.5 (3)	C20A—C18—C20B	17.0 (3)
C2—C3—C4	114.4 (3)	N1—C18—C20B	105.6 (4)
O4—C4—C3	103.1 (3)	C19—C18—C20B	108.2 (4)
O4—C4—C5	112.3 (3)	C21A—C20A—C25A	120.0
C3—C4—C5	112.6 (3)	C21A—C20A—C18	123.0 (4)
O5—C5—C6	105.8 (3)	C25A—C20A—C18	116.9 (4)
O5—C5—C4	110.3 (3)	C20A—C21A—C22A	120.0
C6—C5—C4	114.1 (3)	C23A—C22A—C21A	120.0
C5—C6—C7	113.6 (3)	C22A—C23A—C24A	120.0
N1—C7—C6	110.6 (3)	C23A—C24A—C25A	120.0
N1—C7—C8	113.0 (3)	C24A—C25A—C20A	120.0
C6—C7—C8	107.8 (3)	C21B—C20B—C25B	120.0
O6—C8—O7	124.4 (3)	C21B—C20B—C18	118.0 (5)
O6—C8—C7	125.0 (3)	C25B—C20B—C18	122.0 (5)
O7—C8—C7	110.6 (3)	C20B—C21B—C22B	120.0
O7—C9—C10	106.3 (4)	C21B—C22B—C23B	120.0
O7—C9—C11	108.3 (4)	C24B—C23B—C22B	120.0
C10—C9—C11	113.2 (4)	C25B—C24B—C23B	120.0
O2—C12—O1	104.7 (3)	C24B—C25B—C20B	120.0
C5—O5—C1—O1	75.4 (4)	C2—O2—C12—C13	−150.3 (4)
C5—O5—C1—C2	−42.1 (4)	C2—O2—C12—C14	85.2 (4)
C12—O1—C1—O5	−125.7 (3)	C1—O1—C12—O2	21.9 (4)
C12—O1—C1—C2	−2.3 (4)	C1—O1—C12—C13	138.1 (4)
C12—O2—C2—C3	152.9 (3)	C1—O1—C12—C14	−97.6 (4)
C12—O2—C2—C1	31.9 (4)	C3—O3—C15—O4	−25.3 (4)
O5—C1—C2—O2	102.7 (4)	C3—O3—C15—C16	−143.0 (4)
O1—C1—C2—O2	−18.2 (4)	C3—O3—C15—C17	92.0 (4)
O5—C1—C2—C3	−14.4 (5)	C4—O4—C15—O3	7.3 (5)
O1—C1—C2—C3	−135.4 (3)	C4—O4—C15—C16	124.7 (4)
C15—O3—C3—C2	154.0 (3)	C4—O4—C15—C17	−111.0 (4)
C15—O3—C3—C4	32.2 (4)	C7—N1—C18—C20A	−62.6 (5)
O2—C2—C3—O3	176.5 (3)	C7—N1—C18—C19	167.5 (3)
C1—C2—C3—O3	−68.4 (4)	C7—N1—C18—C20B	−76.6 (4)
O2—C2—C3—C4	−68.7 (4)	N1—C18—C20A—C21A	140.6 (4)
C1—C2—C3—C4	46.4 (5)	C19—C18—C20A—C21A	−92.0 (5)
C15—O4—C4—C3	11.9 (4)	C20B—C18—C20A—C21A	−166.4 (18)
C15—O4—C4—C5	−109.6 (3)	N1—C18—C20A—C25A	−43.4 (5)
O3—C3—C4—O4	−26.6 (4)	C19—C18—C20A—C25A	84.0 (4)
C2—C3—C4—O4	−144.2 (3)	C20B—C18—C20A—C25A	9.7 (14)
O3—C3—C4—C5	94.7 (3)	C25A—C20A—C21A—C22A	0.0
C2—C3—C4—C5	−22.8 (5)	C18—C20A—C21A—C22A	175.9 (5)
C1—O5—C5—C6	−170.0 (3)	C20A—C21A—C22A—C23A	0.0
C1—O5—C5—C4	66.1 (4)	C21A—C22A—C23A—C24A	0.0
O4—C4—C5—O5	85.7 (3)	C22A—C23A—C24A—C25A	0.0
C3—C4—C5—O5	−30.3 (4)	C23A—C24A—C25A—C20A	0.0
O4—C4—C5—C6	−33.2 (4)	C21A—C20A—C25A—C24A	0.0
C3—C4—C5—C6	−149.2 (3)	C18—C20A—C25A—C24A	−176.2 (5)
O5—C5—C6—C7	169.6 (3)	C20A—C18—C20B—C21B	10.2 (14)
C4—C5—C6—C7	−68.9 (4)	N1—C18—C20B—C21B	142.2 (4)
C18—N1—C7—C6	168.5 (3)	C19—C18—C20B—C21B	−101.7 (5)
C18—N1—C7—C8	−70.6 (4)	C20A—C18—C20B—C25B	−170.3 (19)
C5—C6—C7—N1	−74.5 (4)	N1—C18—C20B—C25B	−38.3 (6)
C5—C6—C7—C8	161.6 (3)	C19—C18—C20B—C25B	77.8 (5)
C9—O7—C8—O6	−7.7 (6)	C25B—C20B—C21B—C22B	0.0
C9—O7—C8—C7	169.1 (3)	C18—C20B—C21B—C22B	179.5 (6)
N1—C7—C8—O6	−20.1 (5)	C20B—C21B—C22B—C23B	0.0
C6—C7—C8—O6	102.4 (4)	C21B—C22B—C23B—C24B	0.0
N1—C7—C8—O7	163.1 (3)	C22B—C23B—C24B—C25B	0.0
C6—C7—C8—O7	−74.4 (4)	C23B—C24B—C25B—C20B	0.0
C8—O7—C9—C10	−134.7 (4)	C21B—C20B—C25B—C24B	0.0
C8—O7—C9—C11	103.3 (4)	C18—C20B—C25B—C24B	−179.4 (6)
C2—O2—C12—O1	−33.6 (4)