(R)-3,4,5-Tride-oxy-5,6-didehydro-1,2-O-(2,2,2-trichloro-ethyl-idene)-α-d-gluco-furan-ose-6,3-carbolactone: a new derivative of α-chloralose.

THE TITLE COMPOUND [SYSTEMATIC NAME: (R)-2-trichloro-methyl-3a,3b,7a,8a-tetra-hydro-5H-pyrano[2',3':4,5]furano[2,3-d][1,3]dioxol-5-one], C(9)H(7)Cl(3)O(5), a triyclic system that contains a central α-d-furan-ose ring cis-fused with a dioxolane ring as well as a δ-lactone ring, exhibits a twisted conformation. The CCl(3) group has an axial orientation. The furan-ose ring approximates an envelope conformation due to the α,β-unsaturated lactone functionality. The asymmetric unit contains two independent mol-ecules with almost identical geometries.

Related literature

For background regarding α-chloralose and δ-lactones, see: Collins et al. (1983 ▶); Zosimo-Landolfo & Tronchet (1999 ▶); Wu et al. (1992 ▶).

Experimental

Crystal data

C9H7Cl3O5

M = 301.50

Orthorhombic,

a = 9.129 (4) Å

b = 11.264 (4) Å

c = 23.156 (7) Å

V = 2381.1 (15) Å3

Z = 8

Mo Kα radiation

μ = 0.77 mm−1

T = 298 (1) K

0.60 × 0.40 × 0.10 mm

Data collection

Siemens P4 diffractometer

Absorption correction: ψ scan (XSCANS; Siemens, 1996 ▶) T min = 0.803, T max = 0.926

6901 measured reflections

4735 independent reflections

3838 reflections with I > 2σ(I)

R int = 0.044

3 standard reflections every 97 reflections intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.111

S = 1.06

4735 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.35 e Å−3

Absolute structure: Flack (1983 ▶), 2010 Friedel pairs

Flack parameter: 0.04 (8)

Data collection: XSCANS (Siemens, 1996 ▶); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808026196/pv2095sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026196/pv2095Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C9H7Cl3O5	Dx = 1.682 Mg m−3
Mr = 301.50	Melting point = 416–418 K
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 78 reflections
a = 9.129 (4) Å	θ = 4.6–12.4º
b = 11.264 (4) Å	µ = 0.77 mm−1
c = 23.156 (7) Å	T = 298 (1) K
V = 2381.1 (15) Å3	Cell measurement pressure: 101(2) kPa
Z = 8	Prism, colourless
F000 = 1216	0.60 × 0.40 × 0.10 mm

Siemens P4 diffractometer	Rint = 0.044
Radiation source: fine-focus sealed tube	θmax = 26.2º
Monochromator: graphite	θmin = 1.8º
T = 298(1) K	h = −11→11
ω scans	k = −14→14
Absorption correction: ψ scan(XSCANS; Siemens, 1996)	l = −28→28
Tmin = 0.803, Tmax = 0.926	3 standard reflections
6901 measured reflections	every 97 reflections
4735 independent reflections	intensity decay: 2%
3838 reflections with I > 2σ(I)

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.044	w = 1/[σ2(Fo2) + (0.0319P)2 + 1.7306P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.111	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.34 e Å−3
4735 reflections	Δρmin = −0.35 e Å−3
307 parameters	Extinction correction: none
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2010 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.04 (8)

	x	y	z	Uiso*/Ueq
Cl1	1.0538 (2)	0.40323 (18)	0.81819 (5)	0.1242 (7)
Cl2	0.80275 (18)	0.39332 (15)	0.74470 (6)	0.1046 (5)
Cl3	0.87777 (16)	0.60974 (15)	0.80223 (5)	0.0921 (4)
O1	1.0741 (4)	0.3469 (3)	0.60422 (14)	0.0810 (10)
C2	1.1264 (5)	0.4432 (4)	0.63415 (15)	0.0612 (10)
H2A	1.2277	0.4611	0.6232	0.073*
O2	1.1138 (3)	0.4251 (3)	0.69476 (11)	0.0730 (9)
C3	1.0260 (4)	0.5478 (3)	0.62175 (13)	0.0510 (8)
H3A	1.0796	0.6165	0.6067	0.061*
O3	0.9574 (3)	0.5723 (2)	0.67532 (9)	0.0533 (6)
C3A	0.9171 (4)	0.5005 (3)	0.57924 (14)	0.0486 (8)
H3AA	0.8186	0.5317	0.5865	0.058*
O4	0.9700 (3)	0.5335 (2)	0.52305 (9)	0.0540 (6)
C5	0.9475 (5)	0.4644 (4)	0.47699 (16)	0.0626 (11)
O5	0.9798 (5)	0.5044 (3)	0.43064 (11)	0.0863 (11)
C6	0.8919 (7)	0.3451 (4)	0.4862 (2)	0.0852 (16)
H6A	0.8621	0.3004	0.4546	0.102*
C7	0.8828 (7)	0.2992 (4)	0.5377 (2)	0.0914 (18)
H7A	0.8493	0.2218	0.5421	0.110*
C7A	0.9250 (6)	0.3685 (4)	0.58927 (18)	0.0684 (12)
H7AA	0.8616	0.3469	0.6218	0.082*
C8	1.0435 (5)	0.5219 (4)	0.71861 (14)	0.0561 (10)
H8A	1.1158	0.5798	0.7323	0.067*
C9	0.9472 (5)	0.4813 (4)	0.76875 (16)	0.0675 (12)
Cl11	0.48873 (14)	0.45925 (9)	0.55424 (4)	0.0678 (3)
Cl12	0.32408 (13)	0.58949 (15)	0.47031 (5)	0.0852 (4)
Cl13	0.63514 (12)	0.59974 (13)	0.46866 (4)	0.0733 (3)
O11	0.3340 (3)	0.6649 (2)	0.68090 (10)	0.0568 (7)
C12	0.3800 (5)	0.7463 (3)	0.63918 (14)	0.0527 (9)
H12A	0.3338	0.8239	0.6452	0.063*
O12	0.3488 (3)	0.7016 (3)	0.58318 (10)	0.0583 (7)
C13	0.5434 (5)	0.7557 (3)	0.64229 (13)	0.0503 (9)
H13A	0.5779	0.8380	0.6443	0.060*
O13	0.5930 (3)	0.6951 (2)	0.59195 (10)	0.0506 (6)
C13A	0.5833 (4)	0.6837 (3)	0.69550 (14)	0.0476 (8)
H13B	0.6778	0.6433	0.6912	0.057*
O14	0.5842 (3)	0.7680 (2)	0.74220 (10)	0.0552 (7)
C15	0.5407 (5)	0.7344 (3)	0.79577 (14)	0.0547 (9)
O15	0.5549 (4)	0.8058 (3)	0.83396 (11)	0.0814 (10)
C16	0.4746 (5)	0.6189 (3)	0.80334 (14)	0.0598 (10)
H16A	0.4626	0.5891	0.8405	0.072*
C17	0.4312 (5)	0.5554 (3)	0.75938 (15)	0.0542 (9)
H17A	0.3833	0.4836	0.7655	0.065*
C17A	0.4586 (4)	0.5981 (3)	0.69935 (13)	0.0460 (8)
H17B	0.4750	0.5307	0.6734	0.055*
C18	0.4790 (4)	0.7002 (3)	0.55198 (14)	0.0498 (8)
H18A	0.4872	0.7724	0.5286	0.060*
C19	0.4815 (4)	0.5908 (3)	0.51320 (13)	0.0500 (8)

	U11	U22	U33	U12	U13	U23
Cl1	0.1478 (14)	0.1669 (16)	0.0579 (6)	0.0583 (13)	0.0186 (8)	0.0493 (9)
Cl2	0.1170 (11)	0.1059 (11)	0.0909 (9)	−0.0468 (9)	0.0423 (8)	−0.0014 (8)
Cl3	0.0981 (9)	0.1150 (11)	0.0632 (6)	0.0175 (8)	0.0090 (6)	−0.0219 (7)
O1	0.119 (3)	0.0595 (19)	0.0646 (18)	0.0256 (19)	0.0019 (19)	0.0040 (15)
C2	0.068 (2)	0.074 (3)	0.0413 (18)	0.009 (2)	0.0125 (18)	0.0106 (19)
O2	0.082 (2)	0.094 (2)	0.0429 (13)	0.0327 (18)	0.0134 (13)	0.0182 (15)
C3	0.059 (2)	0.0539 (19)	0.0401 (16)	−0.0027 (19)	0.0064 (16)	0.0059 (15)
O3	0.0669 (16)	0.0559 (14)	0.0371 (11)	0.0089 (13)	0.0027 (11)	0.0023 (10)
C3A	0.060 (2)	0.0480 (19)	0.0382 (16)	−0.0023 (17)	0.0064 (16)	0.0007 (15)
O4	0.0784 (17)	0.0454 (13)	0.0380 (11)	−0.0015 (13)	0.0041 (13)	0.0050 (10)
C5	0.089 (3)	0.055 (2)	0.0439 (19)	0.008 (2)	0.010 (2)	−0.0023 (17)
O5	0.141 (3)	0.0767 (19)	0.0410 (13)	0.003 (2)	0.0180 (18)	0.0018 (13)
C6	0.137 (5)	0.059 (3)	0.060 (3)	−0.015 (3)	0.002 (3)	−0.015 (2)
C7	0.153 (5)	0.054 (3)	0.067 (3)	−0.021 (3)	0.008 (3)	−0.004 (2)
C7A	0.106 (4)	0.051 (2)	0.048 (2)	−0.016 (2)	0.009 (2)	0.0023 (18)
C8	0.056 (2)	0.071 (3)	0.0408 (17)	0.005 (2)	0.0053 (17)	0.0085 (17)
C9	0.075 (3)	0.082 (3)	0.0449 (19)	0.009 (2)	0.0119 (19)	0.0139 (19)
Cl11	0.0934 (8)	0.0501 (5)	0.0599 (5)	−0.0081 (5)	0.0111 (6)	−0.0027 (4)
Cl12	0.0661 (6)	0.1375 (12)	0.0518 (5)	0.0059 (7)	−0.0119 (5)	−0.0211 (7)
Cl13	0.0659 (6)	0.1098 (9)	0.0443 (5)	−0.0028 (6)	0.0161 (4)	0.0017 (6)
O11	0.0608 (16)	0.0652 (17)	0.0443 (13)	0.0013 (13)	−0.0010 (12)	0.0127 (12)
C12	0.077 (3)	0.047 (2)	0.0342 (16)	0.0121 (19)	−0.0010 (17)	−0.0003 (15)
O12	0.0589 (16)	0.080 (2)	0.0364 (12)	0.0177 (14)	−0.0038 (11)	−0.0060 (12)
C13	0.075 (3)	0.0403 (17)	0.0355 (15)	−0.0042 (18)	0.0029 (16)	0.0013 (14)
O13	0.0557 (14)	0.0606 (16)	0.0356 (11)	−0.0098 (12)	0.0012 (10)	−0.0033 (11)
C13A	0.063 (2)	0.0419 (18)	0.0377 (16)	0.0000 (16)	−0.0030 (15)	−0.0069 (15)
O14	0.0838 (18)	0.0433 (13)	0.0386 (11)	−0.0123 (13)	−0.0030 (12)	−0.0040 (10)
C15	0.080 (3)	0.0457 (18)	0.0378 (16)	−0.0019 (19)	−0.0027 (18)	−0.0038 (15)
O15	0.137 (3)	0.0614 (17)	0.0461 (14)	−0.0131 (19)	−0.0012 (17)	−0.0150 (14)
C16	0.093 (3)	0.050 (2)	0.0359 (16)	0.001 (2)	−0.0011 (19)	0.0065 (15)
C17	0.080 (3)	0.0399 (18)	0.0430 (17)	−0.0034 (18)	−0.0025 (18)	0.0076 (15)
C17A	0.065 (2)	0.0376 (16)	0.0356 (14)	0.0000 (17)	−0.0054 (15)	−0.0001 (13)
C18	0.062 (2)	0.0500 (19)	0.0376 (15)	0.0018 (17)	0.0035 (17)	0.0075 (15)
C19	0.053 (2)	0.064 (2)	0.0326 (14)	−0.0013 (19)	0.0015 (14)	−0.0001 (15)

Cl1—C9	1.741 (4)	Cl11—C19	1.761 (4)
Cl2—C9	1.741 (5)	Cl12—C19	1.747 (4)
Cl3—C9	1.760 (5)	Cl13—C19	1.744 (4)
O1—C2	1.373 (6)	O11—C12	1.397 (4)
O1—C7A	1.426 (6)	O11—C17A	1.429 (4)
C2—O2	1.423 (4)	C12—O12	1.420 (4)
C2—C3	1.520 (6)	C12—C13	1.497 (6)
C2—H2A	0.9800	C12—H12A	0.9800
O2—C8	1.381 (5)	O12—C18	1.390 (4)
C3—O3	1.417 (4)	C13—O13	1.424 (4)
C3—C3A	1.497 (5)	C13—C13A	1.520 (5)
C3—H3A	0.9800	C13—H13A	0.9800
O3—C8	1.395 (4)	O13—C18	1.394 (4)
C3A—O4	1.436 (4)	C13A—O14	1.439 (4)
C3A—C7A	1.507 (6)	C13A—C17A	1.495 (5)
C3A—H3AA	0.9800	C13A—H13B	0.9800
O4—C5	1.337 (5)	O14—C15	1.356 (4)
C5—O5	1.201 (5)	C15—O15	1.202 (4)
C5—C6	1.452 (7)	C15—C16	1.445 (5)
C6—C7	1.302 (6)	C16—C17	1.306 (5)
C6—H6A	0.9300	C16—H16A	0.9300
C7—C7A	1.478 (6)	C17—C17A	1.492 (5)
C7—H7A	0.9300	C17—H17A	0.9300
C7A—H7AA	0.9800	C17A—H17B	0.9800
C8—C9	1.527 (5)	C18—C19	1.526 (5)
C8—H8A	0.9800	C18—H18A	0.9800
C2—O1—C7A	108.6 (4)	C12—O11—C17A	108.3 (3)
O1—C2—O2	110.9 (4)	O11—C12—O12	109.8 (3)
O1—C2—C3	107.9 (3)	O11—C12—C13	108.2 (3)
O2—C2—C3	104.4 (3)	O12—C12—C13	105.6 (3)
O1—C2—H2A	111.1	O11—C12—H12A	111.0
O2—C2—H2A	111.1	O12—C12—H12A	111.0
C3—C2—H2A	111.1	C13—C12—H12A	111.0
C8—O2—C2	108.6 (3)	C18—O12—C12	107.9 (3)
O3—C3—C3A	110.6 (3)	O13—C13—C12	104.1 (3)
O3—C3—C2	104.6 (3)	O13—C13—C13A	109.4 (3)
C3A—C3—C2	104.4 (3)	C12—C13—C13A	103.9 (3)
O3—C3—H3A	112.3	O13—C13—H13A	112.9
C3A—C3—H3A	112.3	C12—C13—H13A	112.9
C2—C3—H3A	112.3	C13A—C13—H13A	112.9
C8—O3—C3	107.5 (3)	C18—O13—C13	106.6 (3)
O4—C3A—C3	106.3 (3)	O14—C13A—C17A	112.7 (3)
O4—C3A—C7A	112.3 (3)	O14—C13A—C13	105.0 (3)
C3—C3A—C7A	102.6 (3)	C17A—C13A—C13	102.1 (3)
O4—C3A—H3AA	111.7	O14—C13A—H13B	112.1
C3—C3A—H3AA	111.7	C17A—C13A—H13B	112.1
C7A—C3A—H3AA	111.7	C13—C13A—H13B	112.1
C5—O4—C3A	121.4 (3)	C15—O14—C13A	120.1 (3)
O5—C5—O4	117.2 (4)	O15—C15—O14	117.0 (3)
O5—C5—C6	124.4 (4)	O15—C15—C16	123.9 (3)
O4—C5—C6	118.4 (3)	O14—C15—C16	119.0 (3)
C7—C6—C5	121.6 (4)	C17—C16—C15	121.7 (3)
C7—C6—H6A	119.2	C17—C16—H16A	119.1
C5—C6—H6A	119.2	C15—C16—H16A	119.1
C6—C7—C7A	120.9 (4)	C16—C17—C17A	119.9 (3)
C6—C7—H7A	119.5	C16—C17—H17A	120.0
C7A—C7—H7A	119.5	C17A—C17—H17A	120.0
O1—C7A—C7	110.8 (5)	O11—C17A—C17	108.4 (3)
O1—C7A—C3A	104.6 (4)	O11—C17A—C13A	104.4 (3)
C7—C7A—C3A	112.6 (4)	C17—C17A—C13A	113.0 (3)
O1—C7A—H7AA	109.6	O11—C17A—H17B	110.3
C7—C7A—H7AA	109.6	C17—C17A—H17B	110.3
C3A—C7A—H7AA	109.6	C13A—C17A—H17B	110.3
O2—C8—O3	107.2 (3)	O12—C18—O13	107.1 (2)
O2—C8—C9	109.6 (3)	O12—C18—C19	109.1 (3)
O3—C8—C9	110.1 (3)	O13—C18—C19	110.3 (3)
O2—C8—H8A	110.0	O12—C18—H18A	110.1
O3—C8—H8A	110.0	O13—C18—H18A	110.1
C9—C8—H8A	110.0	C19—C18—H18A	110.1
C8—C9—Cl1	109.3 (3)	C18—C19—Cl13	108.3 (3)
C8—C9—Cl2	111.3 (3)	C18—C19—Cl12	109.2 (3)
Cl1—C9—Cl2	110.3 (3)	Cl13—C19—Cl12	109.01 (16)
C8—C9—Cl3	107.2 (3)	C18—C19—Cl11	111.3 (2)
Cl1—C9—Cl3	109.1 (2)	Cl13—C19—Cl11	109.7 (2)
Cl2—C9—Cl3	109.6 (3)	Cl12—C19—Cl11	109.3 (2)
C7A—O1—C2—O2	94.8 (4)	C17A—O11—C12—O12	99.0 (3)
C7A—O1—C2—C3	−19.0 (4)	C17A—O11—C12—C13	−15.8 (4)
O1—C2—O2—C8	−128.5 (4)	O11—C12—O12—C18	−124.3 (3)
C3—C2—O2—C8	−12.5 (5)	C13—C12—O12—C18	−7.8 (4)
O1—C2—C3—O3	113.3 (3)	O11—C12—C13—O13	107.1 (3)
O2—C2—C3—O3	−4.7 (4)	O12—C12—C13—O13	−10.4 (4)
O1—C2—C3—C3A	−2.9 (4)	O11—C12—C13—C13A	−7.4 (4)
O2—C2—C3—C3A	−120.9 (3)	O12—C12—C13—C13A	−124.9 (3)
C3A—C3—O3—C8	132.0 (3)	C12—C13—O13—C18	25.0 (4)
C2—C3—O3—C8	20.1 (4)	C13A—C13—O13—C18	135.5 (3)
O3—C3—C3A—O4	151.9 (3)	O13—C13—C13A—O14	157.7 (3)
C2—C3—C3A—O4	−96.1 (3)	C12—C13—C13A—O14	−91.6 (3)
O3—C3—C3A—C7A	−90.1 (4)	O13—C13—C13A—C17A	−84.5 (3)
C2—C3—C3A—C7A	21.9 (4)	C12—C13—C13A—C17A	26.1 (3)
C3—C3A—O4—C5	147.0 (4)	C17A—C13A—O14—C15	35.4 (5)
C7A—C3A—O4—C5	35.6 (5)	C13—C13A—O14—C15	145.7 (3)
C3A—O4—C5—O5	171.5 (4)	C13A—O14—C15—O15	174.2 (4)
C3A—O4—C5—C6	−10.9 (6)	C13A—O14—C15—C16	−8.6 (6)
O5—C5—C6—C7	167.8 (6)	O15—C15—C16—C17	164.2 (5)
O4—C5—C6—C7	−9.5 (8)	O14—C15—C16—C17	−12.7 (7)
C5—C6—C7—C7A	1.8 (10)	C15—C16—C17—C17A	4.1 (7)
C2—O1—C7A—C7	154.9 (4)	C12—O11—C17A—C17	153.7 (3)
C2—O1—C7A—C3A	33.4 (4)	C12—O11—C17A—C13A	33.0 (3)
C6—C7—C7A—O1	−93.4 (7)	C16—C17—C17A—O11	−92.0 (5)
C6—C7—C7A—C3A	23.4 (8)	C16—C17—C17A—C13A	23.2 (5)
O4—C3A—C7A—O1	80.2 (4)	O14—C13A—C17A—O11	76.1 (3)
C3—C3A—C7A—O1	−33.5 (4)	C13—C13A—C17A—O11	−35.9 (3)
O4—C3A—C7A—C7	−40.1 (6)	O14—C13A—C17A—C17	−41.4 (4)
C3—C3A—C7A—C7	−153.8 (4)	C13—C13A—C17A—C17	−153.5 (3)
C2—O2—C8—O3	25.7 (4)	C12—O12—C18—O13	23.9 (4)
C2—O2—C8—C9	145.1 (4)	C12—O12—C18—C19	143.2 (3)
C3—O3—C8—O2	−28.8 (4)	C13—O13—C18—O12	−30.9 (3)
C3—O3—C8—C9	−147.9 (3)	C13—O13—C18—C19	−149.5 (3)
O2—C8—C9—Cl1	55.3 (4)	O12—C18—C19—Cl13	173.3 (2)
O3—C8—C9—Cl1	173.0 (3)	O13—C18—C19—Cl13	−69.4 (3)
O2—C8—C9—Cl2	−66.7 (4)	O12—C18—C19—Cl12	54.7 (3)
O3—C8—C9—Cl2	51.0 (4)	O13—C18—C19—Cl12	172.1 (2)
O2—C8—C9—Cl3	173.4 (3)	O12—C18—C19—Cl11	−66.0 (3)
O3—C8—C9—Cl3	−68.9 (4)	O13—C18—C19—Cl11	51.3 (4)