tert-Butyl 6-O-benzyl-2,2-di­chloro-2,5-di­deoxy-4-O-methyl-α-d-ribo-oct-3-pyran­ulosonate

Gainsford, G.J.; Tyler, P.C.

doi:10.1107/S1600536803019640

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tert-Butyl 6-O-benzyl-2,2-dichloro-2,5-dideoxy-4-O-methyl-α-D-ribo-oct-3-pyranulosonate

G. J. Gainsford and P. C. Tyler

The unit cell of the title compound (III) contains two independent molecules of C₂₀H₂₈Cl₂O₇, which differ only in the orientations of the pendant benzyl and hydroxymethyl groups. The anomeric C-OH bonds are unusually short.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803019640/fl6057sup1.cif Contains datablocks global, III
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803019640/fl6057IIIsup2.hkl Contains datablock III

CCDC reference: 225772

checkCIF report

Key indicators

Single-crystal X-ray study
T = 153 K
Mean (C-C) = 0.014 Å
R factor = 0.069
wR factor = 0.169
Data-to-parameter ratio = 7.9

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full too Low ..............      24.74 Deg.

Alert level B
PLAT213_ALERT_2_B Atom C13'    has ADP max/min Ratio .............       4.50 prolat
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.52 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.11 Ratio
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         14
PLAT415_ALERT_2_B Short Inter D-H..H-X       H3O    ..  H20'     =       1.93 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D       H7'O   ..  H7O      =       1.78 Ang.

Alert level C
REFNR01_ALERT_3_C  Ratio of reflections to parameters is < 8 for a
            non-centrosymmetric structure, where ZMAX < 18
            sine(theta)/lambda               -0.5901
            Proportion of unique data used    1.0000
            Ratio reflections to parameters   7.8628
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5880

Author Response: The actual value of theta_max of 27.0 is not significantly less than the expected value. The data/parameter ratio is close to 8.

PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6].....      24.70 Deg.
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.86
PLAT165_ALERT_3_C Nr. of Status R Flagged Non-Hydrogen Atoms .....         12
PLAT213_ALERT_2_C Atom C10'    has ADP max/min Ratio .............       3.50 prolat
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.64 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.23 Ratio
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C9'
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  O5'      =       3.01 Ang.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      36.00 A   3  
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          6
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C20 H28 Cl2 O7

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           24.70
           From the CIF: _reflns_number_total               3955
           Count of symmetry unique reflns         3946
           Completeness (_total/calc)            100.23%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         9
           Fraction of Friedel pairs measured     0.002
           Are heavy atom types Z>Si present          yes

   1 ALERT level A = In general: serious problem
   6 ALERT level B = Potentially serious problem
  13 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
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   9 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: R3M Software (Siemens, 1983); cell refinement: R3M Software; data reduction: R3M Software; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 in WinGX (Farrugia, 1997); software used to prepare material for publication: SHELXL97; PLATON (Spek, 1990).

(III) top

Crystal data top

C₂₀H₂₈Cl₂O₇	F(000) = 952
M_r = 451.34	D_x = 1.341 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 14.863 (3) Å	θ = 2.8–14.5°
b = 18.069 (4) Å	µ = 0.33 mm⁻¹
c = 8.351 (3) Å	T = 153 K
β = 94.49 (1)°	Rod, colourless
V = 2235.9 (10) Å³	0.58 × 0.08 × 0.07 mm
Z = 4

Data collection top

Siemens/Nicolet R3m 4-circle diffractometer	R_int = 0.061
Radiation source: fine-focus sealed tube	θ_max = 24.7°, θ_min = 1.8°
Graphite monochromator	h = −17→17
ω scan	k = 0→21
4099 measured reflections	l = 0→9
3955 independent reflections	3 standard reflections every 97 reflections
2500 reflections with I > 2σ(I)	intensity decay: 10%

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)] = 0.069	H-atom parameters constrained
wR(F²) = 0.169	w = 1/[σ²(F_o²) + (0.0835P)²] where P = F_o² + 2F_c²)/3
S = 0.96	(Δ/σ)_max < 0.001
3955 reflections	Δρ_max = 0.41 e Å⁻³
503 parameters	Δρ_min = −0.40 e Å⁻³
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.07 (14)

Special details top

Experimental. Crystal decay was monitored by collection of 3 standards and scaled accordingly. A standard 0.8 mm diameter collimator was used.

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	U_iso*/U_eq
Cl1	0.72350 (17)	0.37896 (15)	0.3228 (3)	0.0381 (7)
Cl2	0.69403 (16)	0.52727 (17)	0.2041 (3)	0.0381 (7)
Cl1'	−0.19083 (17)	0.04666 (15)	0.0953 (3)	0.0348 (6)
Cl2'	−0.16490 (16)	0.14624 (18)	−0.1662 (3)	0.0377 (7)
O1	0.6720 (4)	0.5618 (4)	0.5348 (7)	0.0293 (17)
O2	0.6409 (5)	0.4416 (4)	0.5823 (8)	0.0374 (19)
O3	0.8512 (4)	0.5671 (4)	0.4422 (8)	0.0247 (16)
H3O	0.8044	0.5900	0.4079	0.037*
O4	0.8803 (4)	0.4752 (4)	0.2692 (7)	0.0289 (16)
O5	0.8422 (4)	0.4619 (4)	0.6885 (8)	0.0306 (17)
O6	1.1177 (4)	0.4656 (4)	0.4056 (8)	0.0366 (19)
O7	0.9689 (5)	0.5358 (6)	0.0000 (9)	0.066 (3)
H7O	0.9132	0.5405	0.0084	0.100*
O1'	−0.3200 (4)	0.2253 (4)	−0.0416 (8)	0.0338 (18)
O2'	−0.3620 (4)	0.1127 (4)	0.0422 (9)	0.0407 (19)
O3'	−0.1503 (4)	0.2647 (4)	0.0906 (8)	0.0275 (16)
H3'O	−0.2031	0.2809	0.0926	0.041*
O4'	−0.0562 (4)	0.1684 (4)	0.1420 (7)	0.0226 (15)
O5'	−0.2649 (4)	0.2130 (4)	0.3092 (7)	0.0301 (16)
O6'	0.0515 (4)	0.2450 (4)	0.5135 (7)	0.0264 (16)
O7'	0.1218 (4)	0.1133 (4)	0.2546 (7)	0.0276 (16)
H7'O	0.1004	0.0839	0.1838	0.041*
C1	0.6785 (6)	0.4899 (6)	0.5158 (12)	0.029 (2)
C2	0.7372 (6)	0.4729 (6)	0.3726 (11)	0.025 (2)
C3	0.8398 (6)	0.4924 (6)	0.4121 (11)	0.025 (2)
C4	0.8837 (6)	0.4438 (6)	0.5472 (11)	0.026 (2)
H4	0.8708	0.3908	0.5203	0.031*
C5	0.9860 (6)	0.4553 (6)	0.5621 (11)	0.027 (2)
H5A	1.0141	0.4198	0.6413	0.032*
H5B	0.9999	0.5059	0.6019	0.032*
C6	1.0259 (6)	0.4442 (6)	0.4005 (12)	0.032 (3)
H6	1.0198	0.3911	0.3675	0.039*
C7	0.9748 (6)	0.4935 (6)	0.2736 (12)	0.032 (2)
H7	0.9839	0.5468	0.3026	0.038*
C8	1.0044 (7)	0.4796 (7)	0.1093 (11)	0.038 (3)
H8A	1.0711	0.4798	0.1131	0.045*
H8B	0.9827	0.4304	0.0710	0.045*
C9	0.6165 (7)	0.5953 (7)	0.6560 (12)	0.036 (3)
C10	0.6290 (9)	0.6767 (7)	0.6345 (14)	0.057 (4)
H10A	0.6068	0.6909	0.5252	0.085*
H10B	0.6932	0.6890	0.6522	0.085*
H10C	0.5951	0.7036	0.7121	0.085*
C11	0.5182 (6)	0.5728 (7)	0.6132 (12)	0.048 (3)
H11A	0.4995	0.5891	0.5037	0.072*
H11B	0.4795	0.5960	0.6887	0.072*
H11C	0.5127	0.5189	0.6199	0.072*
C12	0.6495 (7)	0.5694 (8)	0.8241 (11)	0.051 (4)
H12A	0.6400	0.5159	0.8328	0.076*
H12B	0.6158	0.5951	0.9036	0.076*
H12C	0.7140	0.5804	0.8439	0.076*
C13	0.8339 (8)	0.4024 (7)	0.7946 (13)	0.047 (3)
H13A	0.8048	0.4195	0.8893	0.070*
H13B	0.8940	0.3828	0.8281	0.070*
H13C	0.7972	0.3634	0.7406	0.070*
C14	1.1776 (6)	0.4141 (7)	0.4889 (13)	0.042 (3)
H14A	1.1547	0.3631	0.4704	0.050*
H14B	1.1802	0.4241	0.6057	0.050*
C16	1.3390 (4)	0.3759 (4)	0.5026 (8)	0.047 (3)
H16	1.3268	0.3443	0.5892	0.057*
C17	1.4249 (4)	0.3776 (4)	0.4475 (9)	0.054 (3)
H17	1.4713	0.3471	0.4964	0.065*
C18	1.4427 (3)	0.4238 (4)	0.3207 (9)	0.042 (3)
H18	1.5014	0.4249	0.2831	0.051*
C19	1.3748 (4)	0.4684 (4)	0.2492 (7)	0.043 (3)
H19	1.3870	0.5000	0.1626	0.051*
C20	1.2890 (4)	0.4668 (4)	0.3043 (8)	0.038 (3)
H20	1.2425	0.4972	0.2554	0.046*
C15	1.2711 (3)	0.4205 (4)	0.4311 (8)	0.031 (2)
C1'	−0.3079 (6)	0.1574 (7)	0.0150 (11)	0.028 (2)
C2'	−0.2044 (5)	0.1392 (6)	0.0306 (10)	0.021 (2)
C3'	−0.1466 (5)	0.1924 (5)	0.1467 (11)	0.021 (2)
C4'	−0.1741 (6)	0.1854 (6)	0.3188 (10)	0.022 (2)
H4'	−0.1739	0.1320	0.3505	0.027*
C5'	−0.1091 (6)	0.2275 (6)	0.4320 (11)	0.028 (2)
H5'A	−0.1249	0.2196	0.5437	0.033*
H5'B	−0.1144	0.2810	0.4081	0.033*
C6'	−0.0112 (5)	0.2024 (6)	0.4167 (11)	0.025 (2)
H6'	−0.0048	0.1490	0.4470	0.030*
C7'	0.0085 (5)	0.2124 (5)	0.2415 (10)	0.023 (2)
H7'	0.0009	0.2658	0.2117	0.027*
C8'	0.1013 (6)	0.1874 (5)	0.2057 (11)	0.024 (2)
H8'A	0.1069	0.1916	0.0887	0.029*
H8'B	0.1464	0.2211	0.2606	0.029*
C9'	−0.4149 (6)	0.2548 (7)	−0.0747 (12)	0.039 (3)
C10'	−0.4011 (8)	0.3293 (8)	−0.1374 (18)	0.074 (5)
H10D	−0.3691	0.3596	−0.0540	0.111*
H10E	−0.4597	0.3518	−0.1696	0.111*
H10F	−0.3652	0.3262	−0.2308	0.111*
C11'	−0.4629 (7)	0.2087 (9)	−0.2004 (13)	0.070 (5)
H11D	−0.4718	0.1588	−0.1580	0.106*
H11E	−0.4270	0.2056	−0.2937	0.106*
H11F	−0.5217	0.2309	−0.2326	0.106*
C12'	−0.4612 (6)	0.2547 (7)	0.0804 (12)	0.041 (3)
H12D	−0.4686	0.2036	0.1164	0.062*
H12E	−0.5206	0.2782	0.0626	0.062*
H12F	−0.4244	0.2822	0.1627	0.062*
C13'	−0.3111 (6)	0.1921 (9)	0.4497 (12)	0.055 (4)
H13D	−0.3728	0.2116	0.4394	0.083*
H13E	−0.2786	0.2126	0.5463	0.083*
H13F	−0.3129	0.1380	0.4579	0.083*
C14'	0.0442 (7)	0.2313 (7)	0.6802 (10)	0.034 (3)
H14C	0.0388	0.1773	0.6981	0.040*
H14D	−0.0111	0.2552	0.7141	0.040*
C16'	0.1166 (4)	0.3213 (4)	0.8791 (8)	0.032 (3)
H16'	0.0607	0.3468	0.8792	0.039*
C17'	0.1904 (5)	0.3449 (3)	0.9785 (8)	0.040 (3)
H17'	0.1850	0.3865	1.0466	0.049*
C18'	0.2722 (4)	0.3075 (4)	0.9784 (8)	0.043 (3)
H18'	0.3226	0.3236	1.0464	0.052*
C19'	0.2801 (3)	0.2466 (4)	0.8789 (9)	0.054 (4)
H19'	0.3360	0.2210	0.8788	0.065*
C20'	0.2063 (4)	0.2230 (3)	0.7795 (8)	0.038 (3)
H20'	0.2117	0.1814	0.7115	0.046*
C15'	0.1245 (4)	0.2604 (4)	0.7796 (7)	0.028 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0289 (13)	0.0337 (16)	0.0507 (17)	−0.0057 (13)	−0.0020 (12)	−0.0122 (14)
Cl2	0.0348 (13)	0.0546 (19)	0.0237 (12)	0.0054 (14)	−0.0061 (10)	0.0035 (13)
Cl1'	0.0348 (14)	0.0327 (16)	0.0373 (15)	−0.0017 (12)	0.0049 (11)	−0.0069 (13)
Cl2'	0.0308 (13)	0.064 (2)	0.0194 (12)	−0.0019 (14)	0.0080 (10)	−0.0025 (13)
O1	0.035 (4)	0.031 (5)	0.022 (4)	0.009 (3)	0.006 (3)	−0.005 (3)
O2	0.043 (4)	0.041 (5)	0.029 (4)	−0.001 (4)	0.012 (3)	0.005 (4)
O3	0.020 (3)	0.028 (4)	0.026 (4)	0.009 (3)	0.001 (3)	0.001 (3)
O4	0.024 (3)	0.034 (4)	0.029 (4)	−0.006 (3)	0.005 (3)	−0.004 (3)
O5	0.023 (3)	0.036 (4)	0.033 (4)	−0.001 (3)	0.004 (3)	0.007 (4)
O6	0.023 (4)	0.043 (5)	0.045 (4)	0.004 (3)	0.005 (3)	0.015 (4)
O7	0.069 (6)	0.092 (8)	0.036 (4)	0.010 (6)	−0.008 (4)	0.016 (6)
O1'	0.022 (3)	0.046 (5)	0.033 (4)	−0.002 (3)	0.002 (3)	0.014 (4)
O2'	0.020 (4)	0.043 (5)	0.059 (5)	−0.008 (4)	0.002 (3)	−0.002 (4)
O3'	0.012 (3)	0.033 (4)	0.037 (4)	0.003 (3)	−0.001 (3)	0.005 (3)
O4'	0.017 (3)	0.030 (4)	0.020 (3)	0.000 (3)	−0.002 (2)	−0.003 (3)
O5'	0.024 (3)	0.041 (4)	0.026 (4)	0.002 (3)	0.007 (3)	−0.003 (3)
O6'	0.019 (3)	0.036 (4)	0.024 (3)	−0.008 (3)	−0.002 (3)	0.003 (3)
O7'	0.024 (3)	0.032 (4)	0.027 (4)	0.006 (3)	0.006 (3)	−0.002 (3)
C1	0.024 (5)	0.036 (7)	0.027 (6)	0.016 (5)	0.000 (4)	0.000 (5)
C2	0.022 (5)	0.029 (6)	0.024 (5)	0.011 (4)	−0.003 (4)	−0.001 (5)
C3	0.024 (5)	0.027 (6)	0.024 (5)	0.002 (4)	0.003 (4)	−0.010 (5)
C4	0.023 (5)	0.030 (6)	0.024 (5)	0.007 (5)	0.005 (4)	0.000 (5)
C5	0.019 (5)	0.038 (6)	0.024 (5)	−0.001 (5)	0.002 (4)	0.003 (5)
C6	0.026 (5)	0.034 (7)	0.038 (6)	0.003 (5)	0.009 (4)	0.004 (5)
C7	0.026 (5)	0.033 (6)	0.037 (6)	0.007 (5)	0.009 (4)	0.003 (5)
C8	0.037 (6)	0.042 (7)	0.034 (6)	−0.002 (5)	0.008 (5)	−0.002 (6)
C9	0.035 (6)	0.053 (8)	0.021 (5)	0.004 (6)	0.009 (4)	0.001 (5)
C10	0.074 (9)	0.062 (10)	0.037 (7)	0.004 (8)	0.017 (6)	−0.018 (7)
C11	0.033 (6)	0.069 (10)	0.042 (7)	0.015 (6)	−0.003 (5)	−0.022 (6)
C12	0.042 (6)	0.090 (11)	0.020 (5)	0.018 (7)	0.003 (5)	0.006 (6)
C13	0.048 (7)	0.055 (9)	0.039 (7)	−0.010 (6)	0.016 (5)	0.015 (6)
C14	0.025 (5)	0.054 (8)	0.044 (7)	0.009 (6)	−0.007 (5)	0.016 (6)
C16	0.029 (6)	0.051 (8)	0.060 (8)	0.008 (6)	−0.006 (5)	0.020 (7)
C17	0.038 (6)	0.054 (8)	0.070 (9)	0.013 (7)	0.002 (6)	0.023 (8)
C18	0.030 (6)	0.041 (7)	0.056 (8)	0.004 (6)	0.003 (5)	−0.003 (6)
C19	0.039 (6)	0.054 (8)	0.036 (6)	0.001 (6)	0.007 (5)	0.011 (6)
C20	0.027 (5)	0.041 (7)	0.046 (7)	0.005 (5)	0.004 (5)	−0.002 (6)
C15	0.027 (5)	0.039 (7)	0.027 (5)	−0.007 (5)	−0.004 (4)	0.002 (5)
C1'	0.018 (5)	0.047 (7)	0.018 (5)	−0.004 (5)	−0.004 (4)	−0.006 (5)
C2'	0.015 (4)	0.030 (6)	0.018 (4)	0.008 (4)	−0.001 (3)	0.004 (4)
C3'	0.013 (4)	0.022 (5)	0.027 (5)	0.002 (4)	0.000 (4)	−0.010 (4)
C4'	0.023 (5)	0.027 (6)	0.017 (5)	0.001 (4)	0.002 (4)	−0.006 (4)
C5'	0.026 (5)	0.039 (7)	0.019 (5)	−0.003 (5)	0.004 (4)	−0.012 (5)
C6'	0.010 (4)	0.029 (6)	0.036 (6)	−0.005 (4)	−0.001 (4)	−0.004 (5)
C7'	0.020 (5)	0.019 (5)	0.027 (5)	−0.002 (4)	−0.001 (4)	0.004 (4)
C8'	0.015 (4)	0.028 (6)	0.030 (5)	0.004 (4)	0.001 (4)	0.003 (5)
C9'	0.024 (5)	0.067 (9)	0.024 (6)	0.015 (6)	−0.007 (4)	0.012 (6)
C10'	0.042 (7)	0.070 (10)	0.110 (12)	0.018 (7)	0.010 (7)	0.071 (10)
C11'	0.034 (6)	0.142 (15)	0.034 (7)	0.030 (9)	−0.003 (5)	0.003 (9)
C12'	0.026 (5)	0.058 (8)	0.041 (6)	0.009 (6)	0.006 (5)	−0.002 (6)
C13'	0.012 (5)	0.120 (13)	0.035 (6)	−0.014 (6)	0.010 (4)	0.010 (7)
C14'	0.037 (6)	0.045 (7)	0.020 (5)	−0.011 (5)	0.005 (4)	−0.008 (5)
C16'	0.023 (5)	0.034 (6)	0.037 (6)	0.010 (5)	−0.013 (4)	−0.001 (5)
C17'	0.061 (8)	0.025 (6)	0.033 (6)	−0.003 (6)	−0.011 (5)	−0.004 (5)
C18'	0.029 (6)	0.054 (8)	0.043 (7)	0.005 (6)	−0.015 (5)	−0.012 (6)
C19'	0.028 (6)	0.069 (10)	0.065 (8)	−0.005 (6)	0.000 (6)	−0.005 (8)
C20'	0.040 (6)	0.040 (7)	0.034 (6)	0.010 (6)	0.002 (5)	−0.009 (6)
C15'	0.034 (5)	0.020 (6)	0.026 (5)	−0.001 (5)	−0.015 (4)	0.003 (4)

Geometric parameters (Å, º) top

Cl1—C2	1.756 (11)	C13—H13C	0.9800
Cl2—C2	1.792 (9)	C14—C15	1.510 (11)
Cl1'—C2'	1.764 (10)	C14—H14A	0.9900
Cl2'—C2'	1.793 (8)	C14—H14B	0.9900
O1—C1	1.313 (12)	C16—C17	1.3900
O1—C9	1.485 (11)	C16—C15	1.3900
O2—C1	1.197 (12)	C16—H16	0.9500
O3—C3	1.382 (11)	C17—C18	1.3900
O3—H3O	0.8400	C17—H17	0.9500
O4—C3	1.411 (11)	C18—C19	1.3900
O4—C7	1.441 (11)	C18—H18	0.9500
O5—C13	1.405 (12)	C19—C20	1.3900
O5—C4	1.412 (11)	C19—H19	0.9500
O6—C6	1.415 (11)	C20—C15	1.3900
O6—C14	1.430 (12)	C20—H20	0.9500
O7—C8	1.437 (13)	C1'—C2'	1.569 (12)
O7—H7O	0.8400	C2'—C3'	1.572 (12)
O1'—C1'	1.322 (13)	C3'—C4'	1.530 (12)
O1'—C9'	1.514 (11)	C4'—C5'	1.504 (12)
O2'—C1'	1.175 (12)	C4'—H4'	1.0000
O3'—C3'	1.387 (11)	C5'—C6'	1.539 (12)
O3'—H3'O	0.8400	C5'—H5'A	0.9900
O4'—C3'	1.416 (10)	C5'—H5'B	0.9900
O4'—C7'	1.458 (10)	C6'—C7'	1.525 (12)
O5'—C4'	1.436 (10)	C6'—H6'	1.0000
O5'—C13'	1.455 (11)	C7'—C8'	1.504 (12)
O6'—C6'	1.414 (10)	C7'—H7'	1.0000
O6'—C14'	1.427 (10)	C8'—H8'A	0.9900
O7'—C8'	1.426 (11)	C8'—H8'B	0.9900
O7'—H7'O	0.8400	C9'—C10'	1.464 (16)
C1—C2	1.565 (13)	C9'—C11'	1.479 (17)
C2—C3	1.575 (12)	C9'—C12'	1.514 (13)
C3—C4	1.533 (13)	C10'—H10D	0.9800
C4—C5	1.529 (12)	C10'—H10E	0.9800
C4—H4	1.0000	C10'—H10F	0.9800
C5—C6	1.530 (12)	C11'—H11D	0.9800
C5—H5A	0.9900	C11'—H11E	0.9800
C5—H5B	0.9900	C11'—H11F	0.9800
C6—C7	1.539 (14)	C12'—H12D	0.9800
C6—H6	1.0000	C12'—H12E	0.9800
C7—C8	1.494 (13)	C12'—H12F	0.9800
C7—H7	1.0000	C13'—H13D	0.9800
C8—H8A	0.9900	C13'—H13E	0.9800
C8—H8B	0.9900	C13'—H13F	0.9800
C9—C10	1.495 (17)	C14'—C15'	1.496 (10)
C9—C12	1.524 (14)	C14'—H14C	0.9900
C9—C11	1.531 (14)	C14'—H14D	0.9900
C10—H10A	0.9800	C16'—C17'	1.3900
C10—H10B	0.9800	C16'—C15'	1.3900
C10—H10C	0.9800	C16'—H16'	0.9500
C11—H11A	0.9800	C17'—C18'	1.3900
C11—H11B	0.9800	C17'—H17'	0.9500
C11—H11C	0.9800	C18'—C19'	1.3900
C12—H12A	0.9800	C18'—H18'	0.9500
C12—H12B	0.9800	C19'—C20'	1.3900
C12—H12C	0.9800	C19'—H19'	0.9500
C13—H13A	0.9800	C20'—C15'	1.3900
C13—H13B	0.9800	C20'—H20'	0.9500

C1—O1—C9	122.4 (8)	C15—C20—C19	120.0
C3—O3—H3O	109.5	C15—C20—H20	120.0
C3—O4—C7	114.0 (7)	C19—C20—H20	120.0
C13—O5—C4	114.6 (8)	C20—C15—C16	120.0
C6—O6—C14	113.6 (8)	C20—C15—C14	121.7 (6)
C8—O7—H7O	109.5	C16—C15—C14	118.3 (6)
C1'—O1'—C9'	119.4 (8)	O2'—C1'—O1'	129.2 (9)
C3'—O3'—H3'O	109.5	O2'—C1'—C2'	121.4 (10)
C3'—O4'—C7'	113.7 (6)	O1'—C1'—C2'	109.2 (8)
C4'—O5'—C13'	111.4 (7)	C1'—C2'—C3'	114.0 (7)
C6'—O6'—C14'	111.4 (7)	C1'—C2'—Cl1'	108.2 (7)
C8'—O7'—H7'O	109.5	C3'—C2'—Cl1'	110.3 (6)
O2—C1—O1	128.7 (10)	C1'—C2'—Cl2'	107.3 (6)
O2—C1—C2	121.3 (10)	C3'—C2'—Cl2'	108.7 (6)
O1—C1—C2	109.7 (9)	Cl1'—C2'—Cl2'	108.1 (5)
C1—C2—C3	112.6 (7)	O3'—C3'—O4'	106.9 (7)
C1—C2—Cl1	108.0 (7)	O3'—C3'—C4'	112.9 (7)
C3—C2—Cl1	110.9 (6)	O4'—C3'—C4'	108.9 (7)
C1—C2—Cl2	107.8 (6)	O3'—C3'—C2'	111.3 (7)
C3—C2—Cl2	108.9 (7)	O4'—C3'—C2'	105.6 (7)
Cl1—C2—Cl2	108.4 (5)	C4'—C3'—C2'	110.8 (7)
O3—C3—O4	108.3 (8)	O5'—C4'—C5'	114.4 (8)
O3—C3—C4	112.7 (8)	O5'—C4'—C3'	103.7 (7)
O4—C3—C4	108.2 (8)	C5'—C4'—C3'	110.0 (7)
O3—C3—C2	111.0 (8)	O5'—C4'—H4'	109.5
O4—C3—C2	104.1 (7)	C5'—C4'—H4'	109.5
C4—C3—C2	112.1 (8)	C3'—C4'—H4'	109.5
O5—C4—C5	113.4 (7)	C4'—C5'—C6'	111.3 (8)
O5—C4—C3	107.1 (7)	C4'—C5'—H5'A	109.4
C5—C4—C3	110.2 (8)	C6'—C5'—H5'A	109.4
O5—C4—H4	108.7	C4'—C5'—H5'B	109.4
C5—C4—H4	108.7	C6'—C5'—H5'B	109.4
C3—C4—H4	108.7	H5'A—C5'—H5'B	108.0
C4—C5—C6	111.2 (7)	O6'—C6'—C7'	108.4 (7)
C4—C5—H5A	109.4	O6'—C6'—C5'	112.2 (8)
C6—C5—H5A	109.4	C7'—C6'—C5'	107.4 (7)
C4—C5—H5B	109.4	O6'—C6'—H6'	109.6
C6—C5—H5B	109.4	C7'—C6'—H6'	109.6
H5A—C5—H5B	108.0	C5'—C6'—H6'	109.6
O6—C6—C5	112.2 (8)	O4'—C7'—C8'	107.3 (7)
O6—C6—C7	106.6 (8)	O4'—C7'—C6'	108.3 (7)
C5—C6—C7	109.1 (8)	C8'—C7'—C6'	113.8 (7)
O6—C6—H6	109.6	O4'—C7'—H7'	109.1
C5—C6—H6	109.6	C8'—C7'—H7'	109.1
C7—C6—H6	109.6	C6'—C7'—H7'	109.1
O4—C7—C8	107.1 (8)	O7'—C8'—C7'	113.8 (8)
O4—C7—C6	108.2 (8)	O7'—C8'—H8'A	108.8
C8—C7—C6	111.7 (9)	C7'—C8'—H8'A	108.8
O4—C7—H7	109.9	O7'—C8'—H8'B	108.8
C8—C7—H7	109.9	C7'—C8'—H8'B	108.8
C6—C7—H7	109.9	H8'A—C8'—H8'B	107.7
O7—C8—C7	110.2 (9)	C10'—C9'—C11'	109.8 (11)
O7—C8—H8A	109.6	C10'—C9'—C12'	113.2 (11)
C7—C8—H8A	109.6	C11'—C9'—C12'	112.3 (10)
O7—C8—H8B	109.6	C10'—C9'—O1'	103.5 (9)
C7—C8—H8B	109.6	C11'—C9'—O1'	108.8 (9)
H8A—C8—H8B	108.1	C12'—C9'—O1'	108.8 (7)
O1—C9—C10	103.8 (8)	C9'—C10'—H10D	109.5
O1—C9—C12	110.3 (8)	C9'—C10'—H10E	109.5
C10—C9—C12	112.3 (10)	H10D—C10'—H10E	109.5
O1—C9—C11	107.7 (8)	C9'—C10'—H10F	109.5
C10—C9—C11	111.0 (10)	H10D—C10'—H10F	109.5
C12—C9—C11	111.5 (9)	H10E—C10'—H10F	109.5
C9—C10—H10A	109.5	C9'—C11'—H11D	109.5
C9—C10—H10B	109.5	C9'—C11'—H11E	109.5
H10A—C10—H10B	109.5	H11D—C11'—H11E	109.5
C9—C10—H10C	109.5	C9'—C11'—H11F	109.5
H10A—C10—H10C	109.5	H11D—C11'—H11F	109.5
H10B—C10—H10C	109.5	H11E—C11'—H11F	109.5
C9—C11—H11A	109.5	C9'—C12'—H12D	109.5
C9—C11—H11B	109.5	C9'—C12'—H12E	109.5
H11A—C11—H11B	109.5	H12D—C12'—H12E	109.5
C9—C11—H11C	109.5	C9'—C12'—H12F	109.5
H11A—C11—H11C	109.5	H12D—C12'—H12F	109.5
H11B—C11—H11C	109.5	H12E—C12'—H12F	109.5
C9—C12—H12A	109.5	O5'—C13'—H13D	109.5
C9—C12—H12B	109.5	O5'—C13'—H13E	109.5
H12A—C12—H12B	109.5	H13D—C13'—H13E	109.5
C9—C12—H12C	109.5	O5'—C13'—H13F	109.5
H12A—C12—H12C	109.5	H13D—C13'—H13F	109.5
H12B—C12—H12C	109.5	H13E—C13'—H13F	109.5
O5—C13—H13A	109.5	O6'—C14'—C15'	111.2 (7)
O5—C13—H13B	109.5	O6'—C14'—H14C	109.4
H13A—C13—H13B	109.5	C15'—C14'—H14C	109.4
O5—C13—H13C	109.5	O6'—C14'—H14D	109.4
H13A—C13—H13C	109.5	C15'—C14'—H14D	109.4
H13B—C13—H13C	109.5	H14C—C14'—H14D	108.0
O6—C14—C15	110.4 (8)	C17'—C16'—C15'	120.0
O6—C14—H14A	109.6	C17'—C16'—H16'	120.0
C15—C14—H14A	109.6	C15'—C16'—H16'	120.0
O6—C14—H14B	109.6	C18'—C17'—C16'	120.0
C15—C14—H14B	109.6	C18'—C17'—H17'	120.0
H14A—C14—H14B	108.1	C16'—C17'—H17'	120.0
C17—C16—C15	120.0	C17'—C18'—C19'	120.0
C17—C16—H16	120.0	C17'—C18'—H18'	120.0
C15—C16—H16	120.0	C19'—C18'—H18'	120.0
C18—C17—C16	120.0	C18'—C19'—C20'	120.0
C18—C17—H17	120.0	C18'—C19'—H19'	120.0
C16—C17—H17	120.0	C20'—C19'—H19'	120.0
C17—C18—C19	120.0	C15'—C20'—C19'	120.0
C17—C18—H18	120.0	C15'—C20'—H20'	120.0
C19—C18—H18	120.0	C19'—C20'—H20'	120.0
C20—C19—C18	120.0	C20'—C15'—C16'	120.0
C20—C19—H19	120.0	C20'—C15'—C14'	119.3 (6)
C18—C19—H19	120.0	C16'—C15'—C14'	120.6 (6)

C9—O1—C1—O2	3.3 (16)	C9'—O1'—C1'—O2'	2.1 (15)
C9—O1—C1—C2	176.7 (7)	C9'—O1'—C1'—C2'	177.3 (7)
O2—C1—C2—C3	−116.0 (11)	O2'—C1'—C2'—C3'	−124.2 (10)
O1—C1—C2—C3	70.0 (10)	O1'—C1'—C2'—C3'	60.2 (10)
O2—C1—C2—Cl1	6.9 (11)	O2'—C1'—C2'—Cl1'	−1.1 (11)
O1—C1—C2—Cl1	−167.1 (7)	O1'—C1'—C2'—Cl1'	−176.7 (6)
O2—C1—C2—Cl2	123.9 (9)	O2'—C1'—C2'—Cl2'	115.3 (9)
O1—C1—C2—Cl2	−50.1 (9)	O1'—C1'—C2'—Cl2'	−60.3 (9)
C7—O4—C3—O3	57.8 (10)	C7'—O4'—C3'—O3'	60.5 (9)
C7—O4—C3—C4	−64.6 (10)	C7'—O4'—C3'—C4'	−61.9 (9)
C7—O4—C3—C2	176.0 (8)	C7'—O4'—C3'—C2'	179.0 (7)
C1—C2—C3—O3	−62.2 (11)	C1'—C2'—C3'—O3'	−63.1 (10)
Cl1—C2—C3—O3	176.5 (6)	Cl1'—C2'—C3'—O3'	174.9 (6)
Cl2—C2—C3—O3	57.3 (9)	Cl2'—C2'—C3'—O3'	56.6 (8)
C1—C2—C3—O4	−178.6 (8)	C1'—C2'—C3'—O4'	−178.7 (7)
Cl1—C2—C3—O4	60.2 (8)	Cl1'—C2'—C3'—O4'	59.3 (8)
Cl2—C2—C3—O4	−59.1 (8)	Cl2'—C2'—C3'—O4'	−59.1 (8)
C1—C2—C3—C4	64.8 (10)	C1'—C2'—C3'—C4'	63.5 (10)
Cl1—C2—C3—C4	−56.4 (9)	Cl1'—C2'—C3'—C4'	−58.5 (8)
Cl2—C2—C3—C4	−175.7 (7)	Cl2'—C2'—C3'—C4'	−176.8 (6)
C13—O5—C4—C5	−91.5 (10)	C13'—O5'—C4'—C5'	−75.9 (11)
C13—O5—C4—C3	146.7 (8)	C13'—O5'—C4'—C3'	164.2 (8)
O3—C3—C4—O5	60.3 (10)	O3'—C3'—C4'—O5'	59.8 (9)
O4—C3—C4—O5	−179.9 (7)	O4'—C3'—C4'—O5'	178.4 (7)
C2—C3—C4—O5	−65.8 (10)	C2'—C3'—C4'—O5'	−65.8 (9)
O3—C3—C4—C5	−63.5 (10)	O3'—C3'—C4'—C5'	−63.1 (10)
O4—C3—C4—C5	56.3 (10)	O4'—C3'—C4'—C5'	55.6 (10)
C2—C3—C4—C5	170.4 (8)	C2'—C3'—C4'—C5'	171.3 (8)
O5—C4—C5—C6	−173.0 (9)	O5'—C4'—C5'—C6'	−171.3 (8)
C3—C4—C5—C6	−52.9 (11)	C3'—C4'—C5'—C6'	−55.0 (11)
C14—O6—C6—C5	74.6 (11)	C14'—O6'—C6'—C7'	−172.9 (8)
C14—O6—C6—C7	−166.0 (9)	C14'—O6'—C6'—C5'	68.7 (10)
C4—C5—C6—O6	170.8 (8)	C4'—C5'—C6'—O6'	175.7 (8)
C4—C5—C6—C7	53.0 (12)	C4'—C5'—C6'—C7'	56.6 (11)
C3—O4—C7—C8	−174.1 (9)	C3'—O4'—C7'—C8'	−172.0 (7)
C3—O4—C7—C6	65.3 (10)	C3'—O4'—C7'—C6'	64.7 (9)
O6—C6—C7—O4	−177.9 (8)	O6'—C6'—C7'—O4'	180.0 (7)
C5—C6—C7—O4	−56.6 (11)	C5'—C6'—C7'—O4'	−58.6 (10)
O6—C6—C7—C8	64.4 (11)	O6'—C6'—C7'—C8'	60.7 (11)
C5—C6—C7—C8	−174.2 (9)	C5'—C6'—C7'—C8'	−177.9 (8)
O4—C7—C8—O7	72.9 (11)	O4'—C7'—C8'—O7'	−66.2 (9)
C6—C7—C8—O7	−168.8 (8)	C6'—C7'—C8'—O7'	53.7 (11)
C1—O1—C9—C10	−179.9 (9)	C1'—O1'—C9'—C10'	−179.0 (10)
C1—O1—C9—C12	59.7 (12)	C1'—O1'—C9'—C11'	−62.3 (11)
C1—O1—C9—C11	−62.1 (12)	C1'—O1'—C9'—C12'	60.3 (12)
C6—O6—C14—C15	155.3 (8)	C6'—O6'—C14'—C15'	165.3 (8)
C15—C16—C17—C18	0.0	C15'—C16'—C17'—C18'	0.0
C16—C17—C18—C19	0.0	C16'—C17'—C18'—C19'	0.0
C17—C18—C19—C20	0.0	C17'—C18'—C19'—C20'	0.0
C18—C19—C20—C15	0.0	C18'—C19'—C20'—C15'	0.0
C19—C20—C15—C16	0.0	C19'—C20'—C15'—C16'	0.0
C19—C20—C15—C14	−176.7 (8)	C19'—C20'—C15'—C14'	−176.0 (7)
C17—C16—C15—C20	0.0	C17'—C16'—C15'—C20'	0.0
C17—C16—C15—C14	176.9 (8)	C17'—C16'—C15'—C14'	175.9 (7)
O6—C14—C15—C20	−5.0 (12)	O6'—C14'—C15'—C20'	−73.8 (10)
O6—C14—C15—C16	178.2 (7)	O6'—C14'—C15'—C16'	110.3 (8)

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