(1R,2S,5R)-2-Isoprop­yl-5-methyl­cyclo­hex­yl 3,5-bis-O-(4-chloro­benzo­yl)-2-de­oxy-α-D-erythro-ribofuran­oside

The mol­ecule of the title compound, C₂₉H₃₄Cl₂O₆, possesses normal geometric parameters. The absolute configuration was determined from both the synthetic precursor and anomalous scattering effects. Non-classical C—H...O hydrogen bonds link the mol­ecules in the crystal structure into infinite chains along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.037
• wR factor = 0.072
• Data-to-parameter ratio = 18.7

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.824     0.926
            Tmin' and Tmax expected:      0.919     0.926
            RR' =      0.897
            Please check that your absorption correction is appropriate.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.89
PLAT143_ALERT_4_C su on c - Axis Small or Missing (x 100000) .....         30 Ang.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C6     -   C7      ..       6.10 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C13    -   C14     ..       6.78 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C14    -   C19     ..       5.29 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C26    -   C28     ..       5.02 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17

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           27.48
           From the CIF: _reflns_number_total               6328
           Count of symmetry unique reflns         3796
           Completeness (_total/calc)            166.70%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2532
           Fraction of Friedel pairs measured     0.667
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  10 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
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl 3,5-O-bis(4-chlorobenzoyl)-2-deoxy-α-D-erythro-ribofuranoside

Crystal data

C29H34Cl2O6	F(000) = 1160
Mr = 549.46	Dx = 1.263 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5980 reflections
a = 6.5720 (9) Å	θ = 1.3–27.5°
b = 14.3913 (2) Å	µ = 0.26 mm^−1
c = 30.5468 (3) Å	T = 295 K
V = 2889.1 (4) Å^3	Prism, colorless
Z = 4	0.31 × 0.30 × 0.29 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	4079 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.024
ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −8→8
Tmin = 0.824, Tmax = 0.926	k = −18→18
23110 measured reflections	l = −39→39
6328 independent reflections

Refinement

Refinement on F^2	w = 1/[σ^2(Fo^2) + (0.0264P)^2] where P = (Fo^2 + 2Fc^2)/3
Least-squares matrix: full	(Δ/σ)max = 0.001
R[F^2 > 2σ(F^2)] = 0.037	Δρmax = 0.17 e Å^−3
wR(F^2) = 0.073	Δρmin = −0.19 e Å^−3
S = 0.99	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
6328 reflections	Extinction coefficient: 0.0097 (5)
338 parameters	Absolute structure: Flack (1983), 2535 Friedel pairs?
0 restraints	Absolute structure parameter: −0.04 (6)
H-atom parameters constrained

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.1753 (3)	0.56106 (12)	0.46510 (5)	0.0579 (4)
H1	0.1811	0.6105	0.4871	0.07*
C2	0.3457 (3)	0.49313 (11)	0.47250 (5)	0.0575 (4)
H2A	0.376	0.4867	0.5034	0.069*
H2B	0.468	0.512	0.4571	0.069*
C3	0.2606 (2)	0.40375 (12)	0.45382 (5)	0.0527 (4)
H3	0.3116	0.3495	0.4698	0.063*
C4	0.0310 (2)	0.41415 (12)	0.45913 (6)	0.0573 (4)
H4	−0.0349	0.4004	0.4311	0.069*
C5	−0.0638 (3)	0.35485 (15)	0.49409 (6)	0.0746 (6)
H5A	−0.2058	0.3714	0.4978	0.089*
H5B	−0.0564	0.2898	0.4859	0.089*
C6	−0.0589 (3)	0.36057 (12)	0.57168 (7)	0.0654 (5)
C7	0.0681 (3)	0.37772 (12)	0.61133 (6)	0.0639 (5)
C8	0.2715 (3)	0.39963 (16)	0.60904 (7)	0.0839 (6)
H8	0.3341	0.4055	0.5819	0.101*
C9	0.3833 (4)	0.41294 (18)	0.64684 (8)	0.0939 (7)
H9	0.5205	0.4282	0.6451	0.113*
C10	0.2916 (4)	0.40355 (17)	0.68663 (8)	0.0913 (7)
C11	0.0898 (4)	0.38282 (18)	0.68969 (7)	0.0921 (7)
H11	0.0277	0.3777	0.717	0.111*
C12	−0.0217 (3)	0.36948 (16)	0.65190 (7)	0.0827 (6)
H12	−0.1592	0.3547	0.6538	0.099*
C13	0.4885 (3)	0.36665 (11)	0.39689 (6)	0.0579 (5)
C14	0.5284 (3)	0.36920 (12)	0.34892 (6)	0.0572 (4)
C15	0.7234 (3)	0.34995 (14)	0.33466 (7)	0.0752 (6)
H15	0.8241	0.3343	0.3547	0.09*
C16	0.7686 (3)	0.35393 (16)	0.29054 (8)	0.0850 (6)
H16	0.8999	0.3415	0.2809	0.102*
C17	0.6197 (4)	0.37621 (15)	0.26117 (7)	0.0761 (6)
C18	0.4254 (3)	0.39418 (16)	0.27452 (6)	0.0806 (6)
H18	0.3248	0.4078	0.2541	0.097*
C19	0.3794 (3)	0.39188 (14)	0.31887 (6)	0.0715 (5)
H19	0.2483	0.4056	0.3283	0.086*
C20	0.0351 (3)	0.66185 (11)	0.41031 (6)	0.0529 (4)
H20	−0.0539	0.6724	0.4356	0.063*
C21	0.1271 (3)	0.75465 (11)	0.39644 (5)	0.0495 (4)
H21	0.2198	0.7416	0.3721	0.059*
C22	−0.0425 (3)	0.81686 (12)	0.37830 (6)	0.0628 (5)
H22A	−0.1347	0.833	0.4019	0.075*
H22B	0.0171	0.874	0.3674	0.075*
C23	−0.1627 (3)	0.77073 (13)	0.34169 (6)	0.0693 (5)
H23A	−0.2698	0.8123	0.3321	0.083*
H23B	−0.0732	0.7594	0.317	0.083*
C24	−0.2560 (3)	0.67954 (13)	0.35650 (7)	0.0700 (5)
H24	−0.3496	0.693	0.3807	0.084*
C25	−0.0890 (3)	0.61674 (12)	0.37397 (6)	0.0664 (5)
H25A	0.0013	0.6	0.3501	0.08*
H25B	−0.1498	0.56	0.385	0.08*
C26	0.2548 (3)	0.80072 (12)	0.43255 (5)	0.0558 (4)
H26	0.3542	0.7544	0.4424	0.067*
C27	0.1330 (3)	0.82984 (15)	0.47265 (6)	0.0827 (6)
H27A	0.2237	0.8539	0.4945	0.124*
H27B	0.0618	0.777	0.4842	0.124*
H27C	0.0368	0.877	0.4645	0.124*
C28	0.3752 (3)	0.88350 (14)	0.41538 (6)	0.0792 (6)
H28A	0.4549	0.8646	0.3906	0.119*
H28B	0.4637	0.9062	0.438	0.119*
H28C	0.283	0.9319	0.4068	0.119*
C29	−0.3780 (4)	0.63339 (17)	0.31998 (8)	0.1016 (8)
H29A	−0.4744	0.677	0.3083	0.152*
H29B	−0.4491	0.5805	0.3315	0.152*
H29C	−0.2874	0.6137	0.2972	0.152*
O1	−0.00496 (18)	0.50987 (8)	0.47007 (4)	0.0654 (3)
O2	0.04625 (18)	0.37014 (9)	0.53462 (4)	0.0707 (4)
O3	−0.2353 (2)	0.33923 (11)	0.57270 (5)	0.0883 (4)
O4	0.30128 (17)	0.39593 (8)	0.40745 (3)	0.0561 (3)
O5	0.61196 (19)	0.34109 (9)	0.42349 (4)	0.0729 (4)
O6	0.19538 (17)	0.59943 (7)	0.42308 (4)	0.0570 (3)
Cl1	0.43514 (13)	0.41471 (7)	0.73426 (2)	0.1418 (3)
Cl2	0.67794 (11)	0.38280 (6)	0.205753 (19)	0.1119 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0746 (11)	0.0548 (9)	0.0444 (10)	0.0031 (9)	−0.0020 (10)	0.0014 (8)
C2	0.0704 (11)	0.0529 (9)	0.0493 (10)	0.0002 (9)	−0.0145 (9)	0.0029 (8)
C3	0.0640 (11)	0.0514 (9)	0.0426 (10)	0.0029 (8)	−0.0099 (8)	0.0048 (8)
C4	0.0606 (10)	0.0626 (11)	0.0488 (10)	−0.0046 (9)	−0.0033 (9)	0.0059 (9)
C5	0.0820 (13)	0.0776 (13)	0.0642 (13)	−0.0164 (11)	−0.0093 (12)	0.0168 (10)
C6	0.0682 (12)	0.0586 (11)	0.0694 (14)	0.0055 (10)	0.0080 (12)	0.0139 (10)
C7	0.0734 (13)	0.0587 (10)	0.0595 (12)	0.0115 (9)	0.0012 (11)	0.0124 (9)
C8	0.0751 (14)	0.1046 (16)	0.0721 (15)	0.0030 (13)	0.0054 (12)	0.0223 (13)
C9	0.0813 (14)	0.121 (2)	0.0797 (16)	−0.0015 (15)	−0.0107 (14)	0.0195 (15)
C10	0.1006 (18)	0.0990 (17)	0.0744 (16)	0.0175 (16)	−0.0149 (14)	0.0044 (14)
C11	0.1066 (19)	0.1137 (19)	0.0561 (14)	0.0251 (16)	0.0096 (14)	0.0021 (13)
C12	0.0753 (13)	0.1008 (16)	0.0719 (15)	0.0190 (13)	0.0122 (13)	0.0086 (13)
C13	0.0564 (11)	0.0514 (9)	0.0658 (13)	−0.0030 (9)	−0.0094 (10)	−0.0072 (9)
C14	0.0592 (10)	0.0556 (10)	0.0569 (12)	−0.0024 (9)	−0.0045 (9)	−0.0084 (8)
C15	0.0630 (12)	0.0880 (14)	0.0746 (15)	0.0012 (11)	−0.0045 (11)	−0.0125 (11)
C16	0.0761 (14)	0.1022 (17)	0.0766 (15)	−0.0030 (13)	0.0129 (13)	−0.0208 (13)
C17	0.0847 (14)	0.0861 (15)	0.0576 (13)	−0.0127 (12)	0.0066 (12)	−0.0193 (11)
C18	0.0778 (14)	0.1079 (17)	0.0560 (13)	−0.0047 (14)	−0.0081 (11)	−0.0069 (12)
C19	0.0689 (12)	0.0859 (14)	0.0598 (13)	0.0042 (11)	−0.0005 (11)	−0.0071 (11)
C20	0.0607 (10)	0.0476 (9)	0.0502 (10)	0.0063 (8)	0.0082 (9)	0.0033 (7)
C21	0.0565 (10)	0.0497 (9)	0.0423 (9)	0.0056 (8)	0.0072 (8)	0.0028 (8)
C22	0.0699 (12)	0.0549 (10)	0.0634 (12)	0.0033 (9)	−0.0044 (10)	0.0068 (9)
C23	0.0674 (12)	0.0724 (12)	0.0681 (13)	0.0063 (10)	−0.0106 (11)	0.0089 (10)
C24	0.0680 (12)	0.0697 (12)	0.0724 (13)	−0.0015 (10)	−0.0060 (10)	−0.0028 (10)
C25	0.0753 (12)	0.0548 (10)	0.0691 (12)	−0.0028 (10)	−0.0056 (11)	−0.0004 (9)
C26	0.0639 (10)	0.0540 (9)	0.0497 (10)	0.0035 (8)	0.0003 (9)	0.0013 (8)
C27	0.1000 (15)	0.0828 (14)	0.0654 (13)	−0.0044 (13)	0.0112 (13)	−0.0210 (11)
C28	0.0793 (13)	0.0792 (14)	0.0791 (14)	−0.0175 (11)	−0.0083 (12)	0.0023 (11)
C29	0.1004 (18)	0.0996 (17)	0.1047 (18)	−0.0100 (14)	−0.0364 (15)	−0.0143 (14)
O1	0.0667 (8)	0.0652 (8)	0.0644 (8)	0.0087 (6)	0.0137 (7)	0.0133 (6)
O2	0.0664 (7)	0.0891 (9)	0.0567 (8)	−0.0099 (7)	−0.0015 (7)	0.0241 (7)
O3	0.0689 (9)	0.1180 (12)	0.0781 (10)	−0.0094 (8)	0.0129 (8)	0.0010 (9)
O4	0.0614 (7)	0.0587 (7)	0.0482 (7)	0.0050 (6)	−0.0062 (6)	−0.0005 (5)
O5	0.0610 (7)	0.0890 (9)	0.0687 (9)	0.0099 (7)	−0.0146 (7)	0.0002 (7)
O6	0.0677 (7)	0.0528 (6)	0.0506 (7)	0.0107 (6)	0.0064 (6)	0.0093 (6)
Cl1	0.1529 (7)	0.1846 (8)	0.0879 (5)	0.0140 (6)	−0.0408 (5)	−0.0086 (5)
Cl2	0.1235 (5)	0.1477 (6)	0.0646 (3)	−0.0173 (5)	0.0188 (4)	−0.0228 (4)

Geometric parameters (Å, º)

C1—O1	1.403 (2)	C16—C17	1.366 (3)
C1—O6	1.4036 (18)	C16—H16	0.93
C1—C2	1.504 (2)	C17—C18	1.365 (3)
C1—H1	0.98	C17—Cl2	1.738 (2)
C2—C3	1.514 (2)	C18—C19	1.388 (3)
C2—H2A	0.97	C18—H18	0.93
C2—H2B	0.97	C19—H19	0.93
C3—O4	1.4460 (18)	C20—O6	1.4381 (19)
C3—C4	1.526 (2)	C20—C25	1.523 (2)
C3—H3	0.98	C20—C21	1.526 (2)
C4—O1	1.437 (2)	C20—H20	0.98
C4—C5	1.502 (2)	C21—C22	1.533 (2)
C4—H4	0.98	C21—C26	1.536 (2)
C5—O2	1.451 (2)	C21—H21	0.98
C5—H5A	0.97	C22—C23	1.522 (2)
C5—H5B	0.97	C22—H22A	0.97
C6—O3	1.200 (2)	C22—H22B	0.97
C6—O2	1.333 (2)	C23—C24	1.518 (3)
C6—C7	1.491 (3)	C23—H23A	0.97
C7—C8	1.375 (3)	C23—H23B	0.97
C7—C12	1.378 (3)	C24—C25	1.519 (2)
C8—C9	1.382 (3)	C24—C29	1.526 (3)
C8—H8	0.93	C24—H24	0.98
C9—C10	1.363 (3)	C25—H25A	0.97
C9—H9	0.93	C25—H25B	0.97
C10—C11	1.363 (3)	C26—C27	1.522 (2)
C10—Cl1	1.741 (2)	C26—C28	1.523 (2)
C11—C12	1.381 (3)	C26—H26	0.98
C11—H11	0.93	C27—H27A	0.96
C12—H12	0.93	C27—H27B	0.96
C13—O5	1.2058 (19)	C27—H27C	0.96
C13—O4	1.3401 (19)	C28—H28A	0.96
C13—C14	1.489 (2)	C28—H28B	0.96
C14—C19	1.381 (2)	C28—H28C	0.96
C14—C15	1.382 (3)	C29—H29A	0.96
C15—C16	1.381 (3)	C29—H29B	0.96
C15—H15	0.93	C29—H29C	0.96
O1—C1—O6	112.63 (14)	C19—C18—H18	120.3
O1—C1—C2	105.72 (13)	C14—C19—C18	119.99 (19)
O6—C1—C2	108.86 (14)	C14—C19—H19	120
O1—C1—H1	109.8	C18—C19—H19	120
O6—C1—H1	109.8	O6—C20—C25	108.88 (13)
C2—C1—H1	109.8	O6—C20—C21	109.38 (13)
C1—C2—C3	102.77 (13)	C25—C20—C21	112.51 (14)
C1—C2—H2A	111.2	O6—C20—H20	108.7
C3—C2—H2A	111.2	C25—C20—H20	108.7
C1—C2—H2B	111.2	C21—C20—H20	108.7
C3—C2—H2B	111.2	C20—C21—C22	108.86 (14)
H2A—C2—H2B	109.1	C20—C21—C26	113.25 (13)
O4—C3—C2	111.54 (13)	C22—C21—C26	113.86 (13)
O4—C3—C4	107.13 (13)	C20—C21—H21	106.8
C2—C3—C4	103.99 (14)	C22—C21—H21	106.8
O4—C3—H3	111.3	C26—C21—H21	106.8
C2—C3—H3	111.3	C23—C22—C21	112.85 (14)
C4—C3—H3	111.3	C23—C22—H22A	109
O1—C4—C5	108.12 (15)	C21—C22—H22A	109
O1—C4—C3	106.35 (13)	C23—C22—H22B	109
C5—C4—C3	115.47 (15)	C21—C22—H22B	109
O1—C4—H4	108.9	H22A—C22—H22B	107.8
C5—C4—H4	108.9	C24—C23—C22	111.59 (15)
C3—C4—H4	108.9	C24—C23—H23A	109.3
O2—C5—C4	108.28 (15)	C22—C23—H23A	109.3
O2—C5—H5A	110	C24—C23—H23B	109.3
C4—C5—H5A	110	C22—C23—H23B	109.3
O2—C5—H5B	110	H23A—C23—H23B	108
C4—C5—H5B	110	C23—C24—C25	109.10 (16)
H5A—C5—H5B	108.4	C23—C24—C29	111.77 (17)
O3—C6—O2	123.3 (2)	C25—C24—C29	112.18 (17)
O3—C6—C7	124.2 (2)	C23—C24—H24	107.9
O2—C6—C7	112.48 (17)	C25—C24—H24	107.9
C8—C7—C12	118.8 (2)	C29—C24—H24	107.9
C8—C7—C6	122.73 (19)	C24—C25—C20	112.92 (15)
C12—C7—C6	118.45 (19)	C24—C25—H25A	109
C7—C8—C9	120.4 (2)	C20—C25—H25A	109
C7—C8—H8	119.8	C24—C25—H25B	109
C9—C8—H8	119.8	C20—C25—H25B	109
C10—C9—C8	119.7 (2)	H25A—C25—H25B	107.8
C10—C9—H9	120.1	C27—C26—C28	109.56 (16)
C8—C9—H9	120.1	C27—C26—C21	114.16 (15)
C11—C10—C9	120.9 (2)	C28—C26—C21	111.97 (14)
C11—C10—Cl1	119.4 (2)	C27—C26—H26	106.9
C9—C10—Cl1	119.7 (2)	C28—C26—H26	106.9
C10—C11—C12	119.3 (2)	C21—C26—H26	106.9
C10—C11—H11	120.3	C26—C27—H27A	109.5
C12—C11—H11	120.3	C26—C27—H27B	109.5
C7—C12—C11	120.9 (2)	H27A—C27—H27B	109.5
C7—C12—H12	119.6	C26—C27—H27C	109.5
C11—C12—H12	119.6	H27A—C27—H27C	109.5
O5—C13—O4	123.47 (17)	H27B—C27—H27C	109.5
O5—C13—C14	123.54 (17)	C26—C28—H28A	109.5
O4—C13—C14	112.99 (15)	C26—C28—H28B	109.5
C19—C14—C15	119.69 (18)	H28A—C28—H28B	109.5
C19—C14—C13	122.36 (17)	C26—C28—H28C	109.5
C15—C14—C13	117.94 (17)	H28A—C28—H28C	109.5
C16—C15—C14	119.9 (2)	H28B—C28—H28C	109.5
C16—C15—H15	120	C24—C29—H29A	109.5
C14—C15—H15	120	C24—C29—H29B	109.5
C17—C16—C15	119.8 (2)	H29A—C29—H29B	109.5
C17—C16—H16	120.1	C24—C29—H29C	109.5
C15—C16—H16	120.1	H29A—C29—H29C	109.5
C18—C17—C16	121.22 (19)	H29B—C29—H29C	109.5
C18—C17—Cl2	119.10 (18)	C1—O1—C4	109.84 (12)
C16—C17—Cl2	119.68 (17)	C6—O2—C5	116.77 (15)
C17—C18—C19	119.4 (2)	C13—O4—C3	115.46 (13)
C17—C18—H18	120.3	C1—O6—C20	115.15 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O5^i	0.98	2.48	3.142 (2)	124
C5—H5A···O5^i	0.97	2.60	3.038 (2)	107

Symmetry code: (i) x−1, y, z.