Packing similarities of three isosteric molecules: 4,5-dichlorophthalic anhydride, 4,5-dibromo­phthalic anhydride and 5,6-dichlorobenzfurazan 1-oxide, including three polymorphs of 5,6-dichlorobenzfurazan 1-oxide

4,5-Dichlorophthalic anhydride (CPA) lies on a twofold axis in space group C2/c; the molecules pack as stacks of two-dimensional sheets. Polymorph A of 5,6-dichloro­benzfurazan 1-oxide (CBF; systematic name 5,6-dichloro-2,1,3-benzoxadiazole 1-oxide) is isomorphous with CPA with disordered CBF molecules being pseudo-isosteric with the CPA molecule. Polymorph C of CBF has similar unit-cell dimensions but the arrangement of the molecules in the cell is different. 4,5-Dibromo­phthalic anhydride occurs in space group P1 in a structure derived from the CPA structure. The four structures all have similar two-dimensional sheets of molecules, but differ, in addition to the disorder of the CBF molecules, in the stacking of successive sheets. There are three polymorphs of 5,6-dichlorobenzfurazan 1-oxide. In all three the molecules are disordered about twofold or pseudo-twofold axes. In all three the molecules form chains involving similar Cl...O contacts along the direction of the twofold axis. In polymorphs A and C these chains form virtually identical two-dimensional sheets with inter-chain C—H...O, C—H...N and Cl...Cl contacts, but with different stacking arrangements between the sheets. In polymorph B the chains are associated in face-to-face pairs with the same face-to-face overlap as in A, at an average distance of 3.42 Å compared to an average distance of 3.38 Å in A (cf. Table 8); there are no two-dimensional sheets.

Computing details

Figures

(Alt) 5,6-dichlorobenzfurazan-1-oxide

Crystal data

C6H2Cl2N2O2	F(000) = 408
Mr = 205.00	Dx = 1.872 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.397 (2) Å	Cell parameters from 25 reflections
b = 8.871 (2) Å	θ = 11–22°
c = 7.222 (4) Å	µ = 0.84 mm^−1
β = 95.12 (3)°	T = 173 K
V = 727.3 (5) Å^3	Sword-shaped, yellow
Z = 4	0.50 × 0.28 × 0.12 mm

Data collection

CAD-4 diffractometer	1140 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
Graphite monochromator	θmax = 32°, θmin = 2.9°
ω–2θ scans	h = −16→16
Absorption correction: psi scan North, A. C. T., Phillips, D. C., and Mathews, F. S. (1968). Acta Cryst., A24, 351-359.	k = 0→13
Tmin = 0.74, Tmax = 0.90	l = −10→10
2528 measured reflections	3 standard reflections every 50 min
1267 independent reflections	intensity decay: <1%

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)] = 0.029	Idealized positions
wR(F^2) = 0.076	Calculated w = 1/[σ^2(Fo^2) + (0.029P)^2 + 0.14P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max = 0.01
1267 reflections	Δρmax = 0.47 e Å^−3
110 parameters	Δρmin = −0.35 e Å^−3
33 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.039 (3)

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 on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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)
C1	0.5438 (5)	0.2394 (5)	0.2850 (10)	0.0196 (6)	0.50
C2	0.4298 (4)	0.2469 (5)	0.1901 (10)	0.0216 (7)	0.50
C3	0.3798 (7)	0.3893 (12)	0.1527 (12)	0.0227 (9)	0.50
H3	0.3044	0.3974	0.0910	0.027*	0.50
C4	0.4430 (9)	0.5146 (12)	0.2069 (15)	0.0202 (8)	0.50
C5	0.5623 (8)	0.5003 (12)	0.2997 (14)	0.0209 (8)	0.50
C6	0.6137 (7)	0.3655 (11)	0.3403 (12)	0.0238 (10)	0.50
H6	0.6890	0.3572	0.3992	0.029*	0.50
N1	0.5718 (2)	0.0959 (2)	0.3104 (3)	0.0247 (4)	0.50
N2	0.3874 (2)	0.1079 (3)	0.1540 (4)	0.0272 (4)	0.50
O1	0.6566 (2)	0.0266 (2)	0.3865 (3)	0.0335 (4)	0.50
O2	0.47343 (13)	0.0101 (2)	0.2272 (3)	0.0299 (4)	0.50
Cl4	0.3794 (6)	0.6869 (7)	0.1563 (9)	0.0276 (5)	0.50
Cl5	0.6330 (5)	0.6699 (6)	0.3490 (9)	0.0257 (4)	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.019 (2)	0.0157 (8)	0.024 (2)	−0.0019 (9)	0.0002 (13)	−0.0023 (8)
C2	0.017 (2)	0.0234 (10)	0.024 (2)	−0.0013 (9)	−0.0006 (13)	−0.0022 (9)
C3	0.0253 (11)	0.015 (3)	0.0282 (11)	0.0038 (11)	0.0041 (9)	−0.0001 (11)
C4	0.0220 (11)	0.016 (2)	0.0229 (11)	−0.0069 (12)	0.0036 (9)	−0.0041 (11)
C5	0.0210 (13)	0.018 (2)	0.0236 (12)	−0.006 (2)	0.0023 (10)	−0.004 (2)
C6	0.0248 (13)	0.018 (3)	0.0286 (11)	0.0066 (15)	0.0032 (10)	0.0004 (13)
N1	0.0205 (9)	0.0205 (8)	0.0320 (10)	−0.0004 (8)	−0.0037 (8)	−0.0012 (7)
N2	0.0217 (10)	0.0227 (8)	0.0359 (11)	−0.0016 (8)	−0.0047 (8)	−0.0035 (7)
O1	0.0256 (7)	0.0249 (8)	0.0478 (10)	0.0049 (6)	−0.0092 (7)	0.0022 (7)
O2	0.0233 (9)	0.0194 (6)	0.0458 (11)	−0.0022 (5)	−0.0037 (8)	−0.0031 (6)
Cl4	0.0272 (11)	0.0213 (11)	0.0343 (5)	0.0031 (7)	0.0032 (6)	0.0015 (6)
Cl5	0.0249 (10)	0.0186 (10)	0.0337 (6)	−0.0029 (6)	0.0028 (6)	−0.0052 (6)

Geometric parameters (Å, º)

C1—N1	1.321 (5)	C4—Cl4	1.717 (11)
C1—C6	1.411 (8)	C5—C6	1.352 (12)
C1—C2	1.415 (5)	C5—Cl5	1.729 (10)
C2—N2	1.341 (5)	N1—O1	1.233 (3)
C2—C3	1.402 (9)	N1—O2	1.441 (3)
C3—C4	1.363 (12)	N2—O2	1.378 (3)
C4—C5	1.467 (4)
C1···C2^i	0.344 (5)	C6···C4^i	1.50 (2)
C1···C1^i	1.077 (8)	N1···N2^i	0.521 (2)
C2···C1^i	0.344 (5)	N1···O2^i	0.945 (3)
C2···C6^i	1.176 (10)	N1···C2^i	1.339 (5)
C2···C2^i	1.750 (6)	N1···N1^i	1.785 (5)
C3···C6^i	0.23 (2)	N1···C1^i	1.915 (4)
C3···C5^i	1.22 (2)	N2···N1^i	0.521 (2)
C1···N2^i	1.452 (5)	N2···O1^i	0.912 (3)
C1···C3^i	1.631 (9)	N2···C1^i	1.452 (5)
C1···N1^i	1.915 (4)	O1···N2^i	0.912 (3)
C2···N1^i	1.339 (5)	O1···O2^i	1.636 (2)
C3···C1^i	1.631 (9)	O2···O2^i	0.663 (3)
C4···C5^i	0.15 (2)	O2···N1^i	0.945 (3)
C4···C4^i	1.39 (2)	O2···O1^i	1.636 (2)
C4···C6^i	1.50 (2)	Cl4···Cl5^i	0.208 (10)
C4···Cl5^i	1.658 (14)	Cl4···C5^i	1.801 (13)
C5···C4^i	0.15 (2)	Cl5···Cl4^i	0.208 (9)
C5···C3^i	1.22 (2)	Cl5···C4^i	1.658 (14)
C5···C5^i	1.53 (2)	Cl4···Cl4^ii	3.723
C5···Cl4^i	1.801 (13)	Cl4···Cl5^iii	3.649
C6···C3^i	0.23 (2)	Cl5···Cl4^iv	3.649
C6···C2^i	1.176 (10)	Cl5···Cl5^v	3.585
C6—C1—C2	124.8 (7)	C6^i—C4—Cl5^i	118.2 (7)
C3—C2—C1	118.4 (6)	C5^i—C4—Cl4	123 (7)
C4—C3—C2	119.0 (8)	C4^i—C4—Cl4	117.1 (4)
C3—C4—C5	120.4 (11)	C6^i—C4—Cl4	124.9 (7)
C6—C5—C4	122.8 (11)	Cl5^i—C4—Cl4	6.8 (3)
C5—C6—C1	114.7 (7)	C4^i—C5—C3^i	171 (8)
N1—C1—C2	108.2 (4)	C4^i—C5—C6	174 (9)
N2—C2—C1	110.5 (4)	C3^i—C5—C6	8.2 (6)
C1—N1—O2	106.3 (3)	C4^i—C5—C4	56 (7)
C2—N2—O2	105.8 (2)	C3^i—C5—C4	131.0 (11)
N2—O2—N1	109.1 (2)	C4^i—C5—C5^i	61 (7)
O1—N1—O2	118.2 (2)	C3^i—C5—C5^i	126.0 (5)
C5—C4—Cl4	122.1 (10)	C6—C5—C5^i	117.8 (5)
C4—C5—Cl5	114.5 (10)	C4—C5—C5^i	5.0 (8)
N1—C1—C6	127.0 (6)	C4^i—C5—Cl5	59 (7)
N2—C2—C3	131.1 (5)	C3^i—C5—Cl5	114.5 (7)
C3—C4—Cl4	117.6 (7)	C5^i—C5—Cl5	119.5 (4)
C6—C5—Cl5	122.7 (7)	C4^i—C5—Cl4^i	53 (7)
O1—N1—C1	135.5 (3)	C3^i—C5—Cl4^i	120.7 (7)
C2^i—C1—C1^i	168.1 (18)	C6—C5—Cl4^i	128.9 (7)
C2^i—C1—N1	85.6 (15)	C4—C5—Cl4^i	108.3 (10)
C1^i—C1—N1	105.5 (2)	C5^i—C5—Cl4^i	113.2 (4)
C2^i—C1—C6	41.5 (13)	Cl5—C5—Cl4^i	6.3 (3)
C1^i—C1—C6	127.5 (5)	C3^i—C6—C2^i	174 (5)
C2^i—C1—C2	165.8 (18)	C3^i—C6—C5	50 (5)
C1^i—C1—C2	2.9 (4)	C2^i—C6—C5	125.8 (8)
C2^i—C1—N2^i	64.6 (14)	C3^i—C6—C1	164 (5)
C1^i—C1—N2^i	126.5 (2)	C2^i—C6—C1	11.2 (3)
N1—C1—N2^i	20.99 (12)	C3^i—C6—C4^i	50 (5)
C6—C1—N2^i	106.0 (5)	C2^i—C6—C4^i	125.6 (8)
C2—C1—N2^i	129.2 (4)	C5—C6—C4^i	0.6 (9)
C2^i—C1—C3^i	43.6 (14)	C1—C6—C4^i	114.5 (7)
C1^i—C1—C3^i	125.4 (4)	N2^i—N1—O2^i	138.2 (5)
N1—C1—C3^i	129.1 (5)	N2^i—N1—O1	41.7 (4)
C6—C1—C3^i	2.2 (8)	O2^i—N1—O1	96.5 (2)
C2—C1—C3^i	122.7 (6)	N2^i—N1—C1	93.8 (4)
N2^i—C1—C3^i	108.1 (5)	O2^i—N1—C1	128.0 (3)
C2^i—C1—N1^i	149.3 (15)	N2^i—N1—C2^i	79.0 (4)
C1^i—C1—N1^i	41.66 (15)	O2^i—N1—C2^i	142.9 (3)
N1—C1—N1^i	63.9 (2)	O1—N1—C2^i	120.6 (2)
C6—C1—N1^i	169.1 (5)	C1—N1—C2^i	14.8 (2)
C2—C1—N1^i	44.3 (2)	N2^i—N1—O2	159.9 (5)
N2^i—C1—N1^i	84.9 (2)	O2^i—N1—O2	21.74 (12)
C3^i—C1—N1^i	167.0 (5)	C2^i—N1—O2	121.1 (2)
C1^i—C2—C6^i	127.3 (16)	N2^i—N1—N1^i	168.2 (4)
C1^i—C2—N1^i	79.6 (14)	O2^i—N1—N1^i	53.6 (2)
C6^i—C2—N1^i	152.8 (6)	O1—N1—N1^i	150.05 (14)
C1^i—C2—N2	102.0 (15)	C1—N1—N1^i	74.5 (2)
C6^i—C2—N2	130.5 (6)	C2^i—N1—N1^i	89.3 (2)
N1^i—C2—N2	22.42 (12)	O2—N1—N1^i	31.86 (12)
C1^i—C2—C3	126.7 (16)	N2^i—N1—C1^i	126.5 (5)
C6^i—C2—C3	1.0 (8)	O2^i—N1—C1^i	95.3 (2)
N1^i—C2—C3	153.5 (5)	O1—N1—C1^i	168.1 (2)
C1^i—C2—C1	9.0 (14)	C1—N1—C1^i	32.8 (3)
C6^i—C2—C1	119.0 (7)	C2^i—N1—C1^i	47.6 (2)
N1^i—C2—C1	88.1 (3)	O2—N1—C1^i	73.5 (2)
C1^i—C2—C2^i	11.4 (14)	N1^i—N1—C1^i	41.66 (15)
C6^i—C2—C2^i	116.3 (5)	N1^i—N2—O1^i	116.0 (5)
N1^i—C2—C2^i	90.7 (2)	N1^i—N2—C2	78.6 (4)
N2—C2—C2^i	113.2 (2)	O1^i—N2—C2	165.4 (3)
C3—C2—C2^i	115.7 (5)	N1^i—N2—O2	27.2 (4)
C1—C2—C2^i	2.8 (3)	O1^i—N2—O2	88.7 (2)
C6^i—C3—C5^i	122 (5)	N1^i—N2—C1^i	65.2 (4)
C6^i—C3—C4	122 (5)	O1^i—N2—C1^i	178.7 (4)
C5^i—C3—C4	0.9 (9)	C2—N2—C1^i	13.4 (2)
C6^i—C3—C2	5 (4)	O2—N2—C1^i	92.5 (2)
C5^i—C3—C2	118.3 (7)	N2^i—O1—N1	22.3 (2)
C6^i—C3—C1^i	14 (5)	N2^i—O1—O2^i	57.4 (2)
C5^i—C3—C1^i	108.6 (7)	N1—O1—O2^i	35.04 (13)
C4—C3—C1^i	109.3 (7)	O2^i—O2—N1^i	126.4 (2)
C2—C3—C1^i	9.7 (3)	O2^i—O2—N2	141.01 (11)
C5^i—C4—C3	8 (7)	N1^i—O2—N2	14.6 (2)
C5^i—C4—C4^i	119 (7)	O2^i—O2—N1	31.86 (12)
C3—C4—C4^i	125.3 (5)	N1^i—O2—N1	94.5 (3)
C5^i—C4—C5	114 (8)	O2^i—O2—O1^i	174.85 (10)
C4^i—C4—C5	5.0 (8)	N1^i—O2—O1^i	48.5 (2)
C5^i—C4—C6^i	6 (8)	N2—O2—O1^i	33.87 (12)
C3—C4—C6^i	7.4 (5)	N1—O2—O1^i	143.0 (2)
C4^i—C4—C6^i	117.9 (5)	Cl5^i—Cl4—C4	70 (4)
C5—C4—C6^i	113.0 (11)	Cl5^i—Cl4—C5^i	66 (4)
C5^i—C4—Cl5^i	117 (7)	C4—Cl4—C5^i	3.9 (6)
C3—C4—Cl5^i	110.9 (7)	Cl4^i—Cl5—C4^i	103 (4)
C4^i—C4—Cl5^i	123.8 (4)	Cl4^i—Cl5—C5	107 (4)
C5—C4—Cl5^i	128.8 (10)	C4^i—Cl5—C5	4.3 (6)

Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+1/2, −y+3/2, −z; (iii) x−1/2, −y+3/2, z−1/2; (iv) x+1/2, −y+3/2, z+1/2; (v) −x+3/2, −y+3/2, −z+1.

(Art) 5,6-dichlorobenzfurazan-1-oxide

Crystal data

C6H2Cl2N2O2	F(000) = 408
Mr = 205.00	Dx = 1.816 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.554 (2) Å	Cell parameters from 24 reflections
b = 8.926 (2) Å	θ = 14–23°
c = 7.310 (6) Å	µ = 0.82 mm^−1
β = 96.10 (4)°	T = 297 K
V = 749.6 (7) Å^3	Sword-shaped, yellow
Z = 4	0.50 × 0.28 × 0.12 mm

Data collection

CAD-4 diffractometer	780 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 28°, θmin = 2.9°
ω–2θ scans	h = −15→15
Absorption correction: psi scan North, A. C. T., Phillips, D. C., and Mathews, F. S. (1968). Acta Cryst., A24, 351-359.	k = 0→11
Tmin = 0.74, Tmax = 0.90	l = −9→9
1811 measured reflections	3 standard reflections every 50 min
908 independent reflections	intensity decay: <1%

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)] = 0.035	Idealized positions
wR(F^2) = 0.085	Calculated w = 1/[σ^2(Fo^2) + (0.032P)^2 + 0.15P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = −0.02
908 reflections	Δρmax = 0.37 e Å^−3
110 parameters	Δρmin = −0.21 e Å^−3
33 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.055 (4)

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 on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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)
C1	0.5406 (9)	0.2445 (6)	0.2823 (19)	0.0389 (15)	0.50
C2	0.4286 (8)	0.2512 (7)	0.190 (2)	0.0390 (15)	0.50
C3	0.3802 (8)	0.3949 (15)	0.1544 (13)	0.0435 (13)	0.50
H3	0.3048	0.4040	0.0953	0.052*	0.50
C4	0.4448 (11)	0.5200 (15)	0.2085 (18)	0.0387 (11)	0.50
C5	0.5629 (10)	0.5011 (14)	0.3005 (17)	0.0387 (10)	0.50
C6	0.6111 (8)	0.3672 (14)	0.3405 (13)	0.0448 (13)	0.50
H6	0.6849	0.3573	0.4023	0.054*	0.50
N1	0.5697 (3)	0.1013 (4)	0.3083 (7)	0.0524 (8)	0.50
N2	0.3867 (3)	0.1148 (5)	0.1545 (7)	0.0549 (9)	0.50
O1	0.6548 (3)	0.0319 (3)	0.3815 (5)	0.0712 (9)	0.50
O2	0.4717 (2)	0.0169 (3)	0.2254 (6)	0.0625 (8)	0.50
Cl4	0.3818 (6)	0.6920 (7)	0.1609 (10)	0.0538 (7)	0.50
Cl5	0.6336 (6)	0.6686 (7)	0.3534 (10)	0.0504 (6)	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.031 (5)	0.0399 (14)	0.044 (4)	−0.0013 (13)	−0.005 (3)	−0.0023 (14)
C2	0.027 (4)	0.0428 (14)	0.045 (4)	−0.0008 (13)	−0.006 (3)	−0.002 (2)
C3	0.042 (2)	0.036 (4)	0.0517 (14)	0.007 (2)	−0.0003 (13)	−0.002 (2)
C4	0.040 (2)	0.034 (3)	0.042 (2)	−0.005 (2)	0.0033 (13)	−0.006 (2)
C5	0.037 (2)	0.035 (3)	0.043 (2)	−0.005 (2)	0.0007 (14)	−0.005 (2)
C6	0.043 (2)	0.038 (4)	0.0520 (14)	0.008 (2)	−0.0012 (13)	−0.001 (2)
N1	0.037 (2)	0.0449 (15)	0.072 (2)	−0.0025 (13)	−0.009 (2)	−0.0039 (14)
N2	0.040 (2)	0.047 (2)	0.075 (2)	−0.0023 (13)	−0.009 (2)	−0.0072 (14)
O1	0.0551 (15)	0.048 (2)	0.104 (2)	0.0106 (14)	−0.0219 (15)	0.005 (2)
O2	0.045 (2)	0.0419 (13)	0.098 (3)	−0.0051 (10)	−0.007 (2)	−0.0051 (15)
Cl4	0.0523 (15)	0.042 (2)	0.0659 (11)	0.0031 (8)	−0.0011 (9)	0.0020 (9)
Cl5	0.0487 (14)	0.037 (2)	0.0644 (11)	−0.0061 (9)	0.0003 (10)	−0.0051 (9)

Geometric parameters (Å, º)

C1—C2	1.397 (6)	N1—O1	1.235 (5)
C2—C3	1.412 (10)	N1—O2	1.439 (4)
C3—C4	1.378 (14)	N2—O2	1.374 (4)
C4—C5	1.465 (5)	C4—Cl4	1.719 (14)
C1—C6	1.404 (10)	C5—C6	1.337 (13)
C1—N1	1.330 (8)	C5—Cl5	1.728 (13)
C2—N2	1.326 (8)
C1···C2^i	0.396 (14)	C6···C3^i	0.27 (2)
C1···C1^i	1.01 (2)	C6···C2^i	1.145 (12)
C1···N2^i	1.475 (9)	C6···C4^i	1.53 (2)
C1···C3^i	1.662 (11)	N1···N2^i	0.559 (4)
C1···N1^i	1.875 (8)	N1···O2^i	0.912 (4)
C2···C1^i	0.396 (14)	N1···C2^i	1.338 (7)
C2···C6^i	1.145 (12)	N1···N1^i	1.740 (8)
C2···N1^i	1.338 (7)	N1···C1^i	1.875 (8)
C2···C2^i	1.786 (14)	N2···N1^i	0.559 (4)
C3···C6^i	0.27 (2)	N2···O1^i	0.905 (5)
C3···C5^i	1.18 (2)	N2···C1^i	1.475 (10)
C3···C1^i	1.662 (11)	O1···N2^i	0.905 (5)
C4···C5^i	0.20 (2)	O1···O2^i	1.588 (4)
C4···C4^i	1.35 (2)	O2···O2^i	0.712 (5)
C4···C6^i	1.53 (2)	O2···N1^i	0.912 (4)
C4···Cl5^i	1.64 (2)	O2···O1^i	1.588 (4)
C5···C4^i	0.20 (2)	Cl4···Cl5^i	0.287 (8)
C5···C3^i	1.18 (2)	Cl4···C5^i	1.83 (2)
C5···C5^i	1.56 (2)	Cl5···Cl4^i	0.287 (8)
C5···Cl4^i	1.83 (2)	Cl5···C4^i	1.64 (2)
N1—C1—C2	108.5 (5)	C6^i—C4—Cl5^i	116.5 (8)
N1—C1—C6	125.3 (9)	C5^i—C4—Cl4	122 (8)
C2—C1—C6	126.2 (9)	C4^i—C4—Cl4	116.7 (4)
N2—C2—C1	110.8 (5)	C6^i—C4—Cl4	126.0 (8)
N2—C2—C3	132.1 (8)	Cl5^i—C4—Cl4	9.4 (3)
C1—C2—C3	117.1 (8)	C4^i—C5—C3^i	172 (8)
C4—C3—C2	119.5 (10)	C4^i—C5—C6	173 (8)
C3—C4—C5	119.2 (15)	C3^i—C5—C6	9.9 (7)
C3—C4—Cl4	117.4 (9)	C4^i—C5—C4	52 (7)
C5—C4—Cl4	123.4 (11)	C3^i—C5—C4	133.2 (16)
C6—C5—C4	123.3 (14)	C4^i—C5—C5^i	59 (8)
C6—C5—Cl5	123.2 (8)	C3^i—C5—C5^i	126.6 (7)
C4—C5—Cl5	113.4 (12)	C6—C5—C5^i	116.7 (6)
C5—C6—C1	114.6 (10)	C4—C5—C5^i	6.7 (10)
O1—N1—C1	136.1 (5)	C4^i—C5—Cl5	62 (8)
O1—N1—O2	118.3 (3)	C3^i—C5—Cl5	113.3 (9)
C1—N1—O2	105.6 (4)	C5^i—C5—Cl5	120.1 (4)
C2—N2—O2	106.3 (4)	C4^i—C5—Cl4^i	53 (8)
N2—O2—N1	108.9 (3)	C3^i—C5—Cl4^i	122.0 (9)
C2^i—C1—C1^i	171 (3)	C6—C5—Cl4^i	131.8 (9)
C2^i—C1—N1	82.7 (19)	C4—C5—Cl4^i	104.8 (11)
C1^i—C1—N1	106.0 (4)	C5^i—C5—Cl4^i	111.4 (4)
C2^i—C1—C2	169 (2)	Cl5—C5—Cl4^i	8.6 (3)
C1^i—C1—C2	2.7 (8)	C3^i—C6—C2^i	177 (5)
C2^i—C1—C6	42.6 (16)	C3^i—C6—C5	49 (5)
C1^i—C1—C6	128.7 (6)	C2^i—C6—C5	128.1 (11)
C2^i—C1—N2^i	60.5 (18)	C3^i—C6—C1	164 (6)
C1^i—C1—N2^i	128.2 (3)	C2^i—C6—C1	13.5 (7)
N1—C1—N2^i	22.2 (2)	C3^i—C6—C4^i	50 (5)
C2—C1—N2^i	130.7 (5)	C2^i—C6—C4^i	127.5 (10)
C6—C1—N2^i	103.0 (8)	C5—C6—C4^i	0.9 (11)
C2^i—C1—C3^i	45.3 (15)	C1—C6—C4^i	114.0 (9)
C1^i—C1—C3^i	126.1 (6)	N2^i—N1—O2^i	136.7 (9)
N1—C1—C3^i	127.9 (8)	N2^i—N1—O1	42.5 (7)
C2—C1—C3^i	123.7 (9)	O2^i—N1—O1	94.2 (4)
C6—C1—C3^i	2.6 (10)	N2^i—N1—C1	93.6 (9)
N2^i—C1—C3^i	105.6 (7)	O2^i—N1—C1	129.7 (5)
C2^i—C1—N1^i	146 (2)	N2^i—N1—C2^i	76.6 (7)
C1^i—C1—N1^i	43.0 (3)	O2^i—N1—C2^i	146.7 (5)
N1—C1—N1^i	63.1 (3)	O1—N1—C2^i	119.1 (5)
C2—C1—N1^i	45.4 (3)	C1—N1—C2^i	17.0 (6)
C6—C1—N1^i	171.7 (8)	N2^i—N1—O2	160.8 (9)
N2^i—C1—N1^i	85.3 (3)	O2^i—N1—O2	24.1 (2)
C3^i—C1—N1^i	169.1 (7)	C2^i—N1—O2	122.6 (5)
C1^i—C2—C6^i	124 (2)	N2^i—N1—N1^i	167.6 (7)
C1^i—C2—N2	104.5 (17)	O2^i—N1—N1^i	55.7 (3)
C6^i—C2—N2	131.6 (8)	O1—N1—N1^i	149.9 (2)
C1^i—C2—N1^i	80.3 (16)	C1—N1—N1^i	74.0 (4)
C6^i—C2—N1^i	155.8 (9)	C2^i—N1—N1^i	91.0 (3)
N2—C2—N1^i	24.2 (2)	O2—N1—N1^i	31.6 (2)
C1^i—C2—C1	7 (2)	N2^i—N1—C1^i	124.6 (8)
C6^i—C2—C1	117.6 (10)	O2^i—N1—C1^i	98.7 (4)
N1^i—C2—C1	86.5 (5)	O1—N1—C1^i	167.1 (4)
C1^i—C2—C3	123 (2)	C1—N1—C1^i	31.0 (6)
C6^i—C2—C3	0.6 (10)	C2^i—N1—C1^i	48.0 (3)
N1^i—C2—C3	156.3 (8)	O2—N1—C1^i	74.6 (4)
C1^i—C2—C2^i	9.0 (18)	N1^i—N1—C1^i	43.0 (3)
C6^i—C2—C2^i	115.2 (7)	N1^i—N2—O1^i	112.8 (9)
N2—C2—C2^i	113.2 (3)	N1^i—N2—C2	79.2 (7)
N1^i—C2—C2^i	89.0 (3)	O1^i—N2—C2	168.0 (5)
C1—C2—C2^i	2.5 (5)	N1^i—N2—O2	27.1 (6)
C3—C2—C2^i	114.7 (6)	O1^i—N2—O2	85.7 (4)
C6^i—C3—C5^i	121 (5)	N1^i—N2—C1^i	64.1 (8)
C6^i—C3—C4	122 (5)	O1^i—N2—C1^i	176.9 (5)
C5^i—C3—C4	1.1 (12)	C2—N2—C1^i	15.0 (4)
C6^i—C3—C2	3 (4)	O2—N2—C1^i	91.2 (4)
C5^i—C3—C2	118.7 (9)	N2^i—O1—N1	24.7 (3)
C6^i—C3—C1^i	14 (5)	N2^i—O1—O2^i	59.6 (3)
C5^i—C3—C1^i	107.3 (9)	N1—O1—O2^i	35.0 (2)
C4—C3—C1^i	108.0 (9)	O2^i—O2—N1^i	124.3 (3)
C2—C3—C1^i	11.5 (6)	O2^i—O2—N2	140.5 (2)
C5^i—C4—C4^i	121 (8)	N1^i—O2—N2	16.2 (3)
C5^i—C4—C3	7 (7)	O2^i—O2—N1	31.6 (2)
C4^i—C4—C3	125.8 (7)	N1^i—O2—N1	92.7 (4)
C5^i—C4—C5	115 (8)	O2^i—O2—O1^i	175.1 (2)
C4^i—C4—C5	6.7 (10)	N1^i—O2—O1^i	50.9 (3)
C5^i—C4—C6^i	6 (7)	N2—O2—O1^i	34.7 (2)
C4^i—C4—C6^i	117.3 (6)	N1—O2—O1^i	143.6 (3)
C3—C4—C6^i	8.5 (6)	Cl5^i—Cl4—C4	70 (3)
C5—C4—C6^i	110.7 (14)	Cl5^i—Cl4—C5^i	65 (3)
C5^i—C4—Cl5^i	112 (8)	C4—Cl4—C5^i	5.3 (6)
C4^i—C4—Cl5^i	126.1 (4)	Cl4^i—Cl5—C4^i	101 (3)
C3—C4—Cl5^i	108.0 (8)	Cl4^i—Cl5—C5	107 (3)
C5—C4—Cl5^i	132.8 (12)	C4^i—Cl5—C5	6.1 (7)

Symmetry code: (i) −x+1, y, −z+1/2.

(Blt) 5,6-dichlorobenzfurazan-1-oxide

Crystal data

C6H2Cl2N2O2	F(000) = 408
Mr = 205.00	Dx = 1.840 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3250 reflections
a = 7.0679 (6) Å	θ = 2–25°
b = 11.7502 (9) Å	µ = 0.83 mm^−1
c = 9.0114 (7) Å	T = 173 K
β = 98.563 (1)°	Prism, yellow
V = 740.05 (10) Å^3	0.5 × 0.35 × 0.3 mm
Z = 4

Data collection

SMART diffractometer	1305 independent reflections
Radiation source: fine-focus sealed tube	1145 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
ω scans	θmax = 25.0°, θmin = 2.9°
Absorption correction: SADABS (sheldrick,1996) ?	h = −8→8
Tmin = 0.63, Tmax = 0.81	k = −11→13
3699 measured reflections	l = −10→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	Idealized positions
S = 1.04	Calculated w = 1/[σ^2(Fo^2) + (0.065P)^2 + 0.91P] where P = (Fo^2 + 2Fc^2)/3
1305 reflections	(Δ/σ)max = 0.03
218 parameters	Δρmax = 0.47 e Å^−3
113 restraints	Δρmin = −0.50 e Å^−3

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 on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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)
C1	0.1896 (3)	0.4137 (4)	−0.2518 (6)	0.0242 (12)	0.622 (4)
C2	0.0951 (3)	0.3091 (3)	−0.2555 (6)	0.0250 (11)	0.622 (4)
C3	0.0561 (5)	0.2584 (5)	−0.1212 (7)	0.0273 (10)	0.622 (4)
H3	−0.0080	0.1873	−0.1213	0.033*	0.62
C4	0.1142 (6)	0.3157 (6)	0.0075 (7)	0.0242 (8)	0.622 (4)
C5	0.2121 (6)	0.4240 (6)	0.0108 (7)	0.0211 (8)	0.622 (4)
C6	0.2510 (5)	0.4745 (5)	−0.1173 (7)	0.0243 (10)	0.622 (4)
H6	0.3150	0.5456	−0.1165	0.029*	0.62
N1	0.2067 (4)	0.4407 (4)	−0.3937 (6)	0.0343 (11)	0.622 (4)
N2	0.0517 (4)	0.2686 (4)	−0.3948 (6)	0.0363 (11)	0.622 (4)
O1	0.2753 (4)	0.5204 (3)	−0.4562 (4)	0.0460 (10)	0.622 (4)
O2	0.1195 (3)	0.3488 (3)	−0.4852 (4)	0.0401 (10)	0.622 (4)
Cl4	0.0718 (7)	0.2592 (5)	0.1750 (5)	0.0368 (7)	0.622 (4)
Cl5	0.2816 (7)	0.4910 (5)	0.1826 (4)	0.0241 (5)	0.622 (4)
C21	0.1242 (4)	0.3440 (5)	−0.2617 (7)	0.0247 (13)	0.378 (4)
C22	0.2116 (4)	0.4509 (4)	−0.2462 (7)	0.0237 (14)	0.378 (4)
C23	0.2549 (7)	0.5019 (6)	−0.1032 (9)	0.0233 (12)	0.378 (4)
H23	0.3144	0.5744	−0.0904	0.028*	0.38
C24	0.2079 (9)	0.4425 (8)	0.0144 (8)	0.0206 (9)	0.378 (4)
C25	0.1173 (9)	0.3319 (8)	−0.0021 (8)	0.0240 (9)	0.378 (4)
C26	0.0744 (7)	0.2812 (6)	−0.1388 (8)	0.0274 (12)	0.378 (4)
H26	0.0150	0.2086	−0.1511	0.033*	0.38
N21	0.1008 (5)	0.3173 (4)	−0.4078 (6)	0.0338 (14)	0.378 (4)
N22	0.2445 (6)	0.4931 (4)	−0.3775 (7)	0.0340 (14)	0.378 (4)
O21	0.0338 (6)	0.2363 (4)	−0.4847 (5)	0.0381 (15)	0.378 (4)
O22	0.1769 (5)	0.4117 (4)	−0.4822 (5)	0.036 (2)	0.378 (4)
Cl24	0.2563 (12)	0.4991 (10)	0.1915 (7)	0.039 (2)	0.378 (4)
Cl25	0.0625 (13)	0.2623 (9)	0.1566 (6)	0.0410 (14)	0.378 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.026 (2)	0.021 (4)	0.026 (2)	0.004 (2)	0.0047 (13)	0.000 (2)
C2	0.023 (2)	0.022 (3)	0.029 (2)	0.002 (2)	0.0009 (14)	−0.004 (2)
C3	0.025 (2)	0.017 (2)	0.038 (2)	−0.0017 (15)	−0.0023 (14)	0.001 (2)
C4	0.0236 (13)	0.019 (2)	0.029 (2)	0.0025 (12)	0.0003 (11)	0.0056 (13)
C5	0.0213 (13)	0.015 (2)	0.0262 (14)	0.0065 (12)	0.0021 (11)	−0.0033 (13)
C6	0.0264 (14)	0.010 (3)	0.038 (2)	0.0042 (14)	0.0080 (13)	−0.001 (2)
N1	0.033 (2)	0.039 (3)	0.030 (2)	−0.003 (2)	0.002 (2)	−0.002 (3)
N2	0.030 (2)	0.046 (3)	0.033 (2)	−0.001 (2)	0.000 (2)	−0.008 (3)
O1	0.060 (2)	0.049 (2)	0.032 (2)	−0.013 (2)	0.016 (2)	0.009 (2)
O2	0.039 (2)	0.052 (3)	0.028 (2)	−0.007 (2)	0.003 (2)	−0.010 (2)
Cl4	0.0363 (13)	0.0388 (12)	0.0335 (10)	−0.0063 (10)	−0.0012 (9)	0.0149 (9)
Cl5	0.0185 (9)	0.0266 (10)	0.0271 (8)	0.0043 (7)	0.0034 (6)	−0.0104 (6)
C21	0.023 (2)	0.022 (3)	0.028 (2)	0.002 (2)	0.001 (2)	−0.003 (2)
C22	0.026 (2)	0.019 (4)	0.026 (2)	0.004 (2)	0.0050 (15)	0.001 (2)
C23	0.026 (2)	0.008 (3)	0.037 (2)	0.006 (2)	0.0087 (14)	−0.002 (2)
C24	0.0207 (14)	0.014 (2)	0.0262 (15)	0.0070 (13)	0.0024 (12)	−0.0034 (14)
C25	0.0237 (14)	0.019 (2)	0.028 (2)	0.0033 (14)	0.0003 (13)	0.0059 (15)
C26	0.025 (2)	0.016 (3)	0.038 (2)	−0.002 (2)	−0.002 (2)	0.001 (2)
N21	0.024 (3)	0.044 (4)	0.031 (2)	−0.002 (2)	0.000 (2)	−0.006 (3)
N22	0.033 (2)	0.039 (4)	0.030 (2)	−0.003 (2)	0.004 (2)	−0.002 (4)
O21	0.048 (3)	0.035 (3)	0.031 (3)	−0.009 (2)	0.004 (3)	−0.012 (2)
O22	0.029 (3)	0.054 (4)	0.025 (3)	−0.011 (3)	0.000 (2)	0.000 (3)
Cl24	0.033 (3)	0.043 (2)	0.041 (2)	0.006 (2)	0.0042 (15)	−0.0134 (14)
Cl25	0.037 (2)	0.045 (2)	0.039 (2)	−0.006 (2)	−0.002 (2)	0.019 (2)

Geometric parameters (Å, º)

C1—C2	1.397 (5)	C21—N21	1.340 (7)
C2—C3	1.413 (7)	C21—C22	1.397 (5)
C3—C4	1.351 (8)	C21—C26	1.418 (7)
C4—C5	1.447 (4)	C22—N22	1.335 (7)
C5—C6	1.361 (8)	C22—C23	1.413 (7)
C1—C6	1.418 (7)	C23—C24	1.351 (8)
C1—N1	1.340 (7)	C24—C25	1.447 (4)
C2—N2	1.335 (7)	C24—Cl24	1.716 (7)
N1—O1	1.230 (5)	C25—C26	1.361 (8)
N1—O2	1.440 (5)	C25—Cl25	1.740 (6)
N2—O2	1.377 (5)	N21—O21	1.230 (5)
C4—Cl4	1.716 (7)	N21—O22	1.440 (5)
C5—Cl5	1.740 (6)	N22—O22	1.377 (5)
C2—C1—C6	123.2 (6)	N21—C21—C22	107.2 (5)
C1—C2—C3	120.3 (6)	N21—C21—C26	129.6 (5)
C4—C3—C2	116.9 (5)	C22—C21—C26	123.2 (6)
C3—C4—C5	122.7 (7)	N22—C22—C21	112.2 (6)
C6—C5—C4	121.4 (6)	N22—C22—C23	127.5 (4)
C5—C6—C1	115.5 (5)	C21—C22—C23	120.3 (6)
N1—C1—C2	107.2 (5)	C24—C23—C22	116.9 (5)
N2—C2—C1	112.2 (6)	C23—C24—C25	122.7 (7)
C1—N1—O2	106.1 (4)	C23—C24—Cl24	119.5 (5)
C2—N2—O2	105.1 (4)	C25—C24—Cl24	117.9 (6)
N2—O2—N1	109.3 (3)	C26—C25—C24	121.4 (7)
O1—N1—O2	118.2 (4)	C26—C25—Cl25	119.4 (5)
C5—C4—Cl4	117.9 (6)	C24—C25—Cl25	119.1 (6)
C4—C5—Cl5	119.1 (6)	C25—C26—C21	115.5 (5)
N1—C1—C6	129.6 (5)	O21—N21—C21	135.7 (5)
N2—C2—C3	127.5 (4)	O21—N21—O22	118.2 (4)
C3—C4—Cl4	119.5 (5)	C21—N21—O22	106.1 (4)
C6—C5—Cl5	119.4 (5)	C22—N22—O22	105.1 (4)
O1—N1—C1	135.7 (5)	N22—O22—N21	109.4 (3)

(Brt) 5,6-dichlorobenzfurazan-1.oxide

Crystal data

C6H2Cl2N2O2	F(000) = 408
Mr = 205.00	Dx = 1.788 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2148 reflections
a = 7.1739 (2) Å	θ = 2–25°
b = 11.8351 (2) Å	µ = 0.80 mm^−1
c = 9.0639 (1) Å	T = 297 K
β = 98.350 (1)°	Prism, yellow
V = 761.40 (3) Å^3	0.50 × 0.35 × 0.30 mm
Z = 4

Data collection

SMART diffractometer	1330 independent reflections
Radiation source: fine-focus sealed tube	1158 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
ω scans	θmax = 25°, θmin = 2.9°
Absorption correction: SADABS (sheldrick,1996) ?	h = −8→8
Tmin = 0.47, Tmax = 0.82	k = −13→14
3751 measured reflections	l = −9→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	Idealized positions
S = 1.73	Calculated w = 1/[σ^2(Fo^2) + (0.045P)^2 + 0.027P] where P = (Fo^2 + 2Fc^2)/3
1330 reflections	(Δ/σ)max = 0.04
218 parameters	Δρmax = 0.37 e Å^−3
113 restraints	Δρmin = −0.31 e Å^−3

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 on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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)
C1	0.1864 (3)	0.4117 (3)	−0.2501 (6)	0.0389 (12)	0.610 (3)
C2	0.0931 (3)	0.3082 (3)	−0.2526 (6)	0.0400 (11)	0.610 (3)
C3	0.0541 (5)	0.2603 (5)	−0.1160 (7)	0.0430 (11)	0.610 (3)
H3	−0.0078	0.1914	−0.1142	0.052*	0.61
C4	0.1102 (6)	0.3185 (6)	0.0102 (7)	0.0397 (8)	0.610 (3)
C5	0.2069 (6)	0.4259 (6)	0.0090 (7)	0.0384 (8)	0.610 (3)
C6	0.2460 (5)	0.4737 (5)	−0.1197 (7)	0.0417 (11)	0.610 (3)
H6	0.3079	0.5426	−0.1211	0.050*	0.61
N1	0.2059 (4)	0.4381 (4)	−0.3912 (5)	0.0571 (10)	0.610 (3)
N2	0.0528 (4)	0.2678 (3)	−0.3902 (5)	0.0610 (11)	0.610 (3)
O1	0.2750 (4)	0.5169 (3)	−0.4533 (4)	0.0796 (12)	0.610 (3)
O2	0.1206 (3)	0.3461 (3)	−0.4803 (3)	0.0685 (11)	0.610 (3)
Cl4	0.0686 (7)	0.2665 (5)	0.1790 (5)	0.0581 (7)	0.610 (3)
Cl5	0.2762 (7)	0.4966 (5)	0.1768 (5)	0.0509 (8)	0.610 (3)
C21	0.1316 (4)	0.3435 (4)	−0.2578 (7)	0.038 (2)	0.390 (3)
C22	0.2172 (4)	0.4494 (4)	−0.2417 (6)	0.0372 (15)	0.390 (3)
C23	0.2616 (6)	0.4972 (6)	−0.0964 (8)	0.0395 (14)	0.390 (3)
H23	0.3188	0.5677	−0.0822	0.047*	0.39
C24	0.2177 (8)	0.4366 (7)	0.0193 (8)	0.0376 (11)	0.390 (3)
C25	0.1288 (9)	0.3267 (8)	−0.0012 (7)	0.0405 (11)	0.390 (3)
C26	0.0847 (7)	0.2789 (6)	−0.1385 (7)	0.043 (2)	0.390 (3)
H26	0.0276	0.2084	−0.1523	0.052*	0.39
N21	0.1049 (5)	0.3177 (4)	−0.4037 (6)	0.0584 (14)	0.390 (3)
N22	0.2458 (5)	0.4920 (4)	−0.3721 (7)	0.0578 (13)	0.390 (3)
O21	0.0374 (6)	0.2376 (4)	−0.4799 (5)	0.0669 (15)	0.390 (3)
O22	0.1778 (5)	0.4126 (3)	−0.4763 (4)	0.064 (2)	0.390 (3)
Cl24	0.2668 (11)	0.4880 (8)	0.1976 (6)	0.0522 (13)	0.390 (3)
Cl25	0.0758 (12)	0.2526 (8)	0.1539 (6)	0.0643 (15)	0.390 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.035 (2)	0.039 (3)	0.043 (2)	−0.005 (2)	0.0068 (14)	−0.002 (2)
C2	0.031 (2)	0.042 (3)	0.046 (2)	−0.004 (2)	0.0028 (15)	−0.009 (2)
C3	0.039 (2)	0.037 (2)	0.052 (2)	−0.006 (2)	0.006 (2)	0.000 (2)
C4	0.0336 (15)	0.041 (2)	0.0443 (15)	0.0015 (13)	0.0053 (12)	0.0045 (13)
C5	0.0324 (14)	0.041 (2)	0.0413 (15)	0.0035 (13)	0.0024 (12)	−0.0050 (13)
C6	0.043 (2)	0.034 (2)	0.048 (2)	−0.0015 (14)	0.0060 (15)	−0.004 (2)
N1	0.057 (2)	0.071 (3)	0.042 (2)	−0.006 (2)	0.001 (2)	−0.004 (3)
N2	0.054 (2)	0.076 (3)	0.050 (2)	−0.003 (2)	0.001 (2)	−0.017 (3)
O1	0.107 (3)	0.084 (2)	0.052 (2)	−0.023 (2)	0.025 (2)	0.011 (2)
O2	0.072 (2)	0.091 (3)	0.043 (2)	−0.007 (2)	0.008 (2)	−0.017 (2)
Cl4	0.0621 (10)	0.0630 (14)	0.0488 (11)	−0.0081 (8)	0.0064 (8)	0.0113 (11)
Cl5	0.0479 (10)	0.060 (2)	0.0450 (11)	−0.0032 (8)	0.0059 (8)	−0.0155 (12)
C21	0.028 (2)	0.043 (4)	0.043 (2)	−0.008 (2)	0.005 (2)	−0.005 (2)
C22	0.036 (2)	0.032 (4)	0.044 (2)	−0.006 (2)	0.007 (2)	0.001 (2)
C23	0.043 (2)	0.030 (3)	0.046 (3)	0.004 (2)	0.008 (2)	−0.007 (2)
C24	0.032 (2)	0.037 (2)	0.043 (2)	0.003 (2)	0.003 (2)	−0.005 (2)
C25	0.035 (2)	0.042 (2)	0.044 (2)	0.002 (2)	0.005 (2)	0.007 (2)
C26	0.039 (2)	0.037 (3)	0.054 (3)	−0.008 (2)	0.007 (2)	0.001 (2)
N21	0.048 (3)	0.076 (4)	0.050 (2)	−0.004 (2)	0.001 (2)	−0.014 (3)
N22	0.058 (3)	0.071 (3)	0.044 (2)	−0.005 (2)	0.003 (2)	−0.002 (3)
O21	0.075 (3)	0.069 (3)	0.055 (3)	−0.010 (2)	0.003 (2)	−0.017 (2)
O22	0.058 (3)	0.089 (5)	0.043 (3)	−0.014 (3)	0.000 (2)	0.004 (3)
Cl24	0.060 (2)	0.0510 (15)	0.045 (2)	0.0031 (14)	0.0038 (13)	−0.0039 (13)
Cl25	0.074 (2)	0.065 (2)	0.055 (2)	−0.0114 (15)	0.0108 (15)	0.016 (2)

Geometric parameters (Å, º)

C1—N1	1.343 (7)	C21—N21	1.343 (7)
C1—C2	1.395 (5)	C21—C22	1.395 (5)
C1—C6	1.404 (7)	C21—C26	1.404 (7)
C2—N2	1.328 (7)	C22—N22	1.328 (7)
C2—C3	1.426 (7)	C22—C23	1.426 (7)
C3—C4	1.345 (8)	C23—C24	1.346 (8)
C4—C5	1.449 (4)	C24—C25	1.449 (4)
C4—Cl4	1.715 (6)	C24—Cl24	1.715 (6)
C5—C6	1.362 (8)	C25—C26	1.362 (8)
C5—Cl5	1.744 (6)	C25—Cl25	1.744 (6)
N1—O1	1.231 (5)	N21—O21	1.231 (5)
N1—O2	1.438 (4)	N21—O22	1.438 (5)
N2—O2	1.371 (5)	N22—O22	1.371 (5)
N1—C1—C2	107.7 (5)	N21—C21—C22	107.8 (5)
N1—C1—C6	128.3 (4)	N21—C21—C26	128.2 (4)
C2—C1—C6	124.0 (6)	C22—C21—C26	124.0 (6)
N2—C2—C1	111.7 (5)	N22—C22—C21	111.7 (5)
N2—C2—C3	129.0 (4)	N22—C22—C23	129.0 (4)
C1—C2—C3	119.3 (5)	C21—C22—C23	119.3 (5)
C4—C3—C2	117.6 (5)	C24—C23—C22	117.5 (5)
C3—C4—C5	121.8 (7)	C23—C24—C25	121.8 (7)
C3—C4—Cl4	120.4 (5)	C23—C24—Cl24	120.4 (5)
C5—C4—Cl4	117.8 (6)	C25—C24—Cl24	117.8 (6)
C6—C5—C4	121.9 (6)	C26—C25—C24	121.9 (7)
C6—C5—Cl5	118.6 (5)	C26—C25—Cl25	118.6 (5)
C4—C5—Cl5	119.4 (6)	C24—C25—Cl25	119.4 (6)
C5—C6—C1	115.4 (5)	C25—C26—C21	115.4 (5)
O1—N1—C1	135.7 (4)	O21—N21—C21	135.7 (5)
O1—N1—O2	118.9 (3)	O21—N21—O22	118.9 (3)
C1—N1—O2	105.3 (4)	C21—N21—O22	105.3 (4)
C2—N2—O2	105.6 (4)	C22—N22—O22	105.6 (4)
N2—O2—N1	109.6 (3)	N22—O22—N21	109.7 (3)

(Clt) 5,6-dichlorobenzfurazan-1-oxide

Crystal data

C6H2Cl2N2O2	F(000) = 408
Mr = 205.00	Dx = 1.807 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.2233 (1) Å	Cell parameters from 1656 reflections
b = 9.0549 (3) Å	θ = 2–25°
c = 11.5700 (4) Å	µ = 0.81 mm^−1
β = 95.315 (2)°	T = 173 K
V = 753.50 (4) Å^3	Thick plate, yellow
Z = 4	0.50 × 0.45 × 0.20 mm

Data collection

SMART diffractometer	659 independent reflections
Radiation source: fine-focus sealed tube	594 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ω scans	θmax = 25.1°, θmin = 3.5°
Absorption correction: SADABS (sheldrick,1996) ?	h = −8→8
Tmin = 0.67, Tmax = 0.85	k = −10→7
3292 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.073	Idealized positions
S = 1.12	Calculated w = 1/[σ^2(Fo^2) + (0.043P)^2 + 0.199P] where P = (Fo^2 + 2Fc^2)/3
659 reflections	(Δ/σ)max = 0.02
109 parameters	Δρmax = 0.18 e Å^−3
33 restraints	Δρmin = −0.21 e Å^−3

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 on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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)
C1	0.5311 (13)	0.2759 (6)	0.7869 (9)	0.028 (2)	0.50
C2	0.4322 (14)	0.2843 (7)	0.6770 (7)	0.028 (2)	0.50
C3	0.3963 (12)	0.4281 (16)	0.6298 (10)	0.0322 (14)	0.50
H3	0.3333	0.4364	0.5550	0.039*	0.50
C4	0.4539 (16)	0.5510 (18)	0.6922 (9)	0.0286 (15)	0.50
C5	0.5525 (16)	0.5284 (18)	0.8080 (9)	0.0296 (15)	0.50
C6	0.5955 (12)	0.3957 (15)	0.8566 (10)	0.0328 (14)	0.50
H6	0.6608	0.3872	0.9280	0.039*	0.50
N1	0.5552 (5)	0.1343 (5)	0.8159 (3)	0.0384 (8)	0.50
N2	0.3926 (5)	0.1483 (5)	0.6335 (4)	0.0410 (8)	0.50
O1	0.6282 (4)	0.0635 (4)	0.8995 (3)	0.0513 (7)	0.50
O2	0.4665 (4)	0.0517 (3)	0.7181 (2)	0.0431 (7)	0.50
Cl4	0.4124 (10)	0.7204 (9)	0.6282 (6)	0.0368 (7)	0.50
Cl5	0.6101 (10)	0.6932 (9)	0.8783 (6)	0.0372 (7)	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.027 (4)	0.036 (2)	0.019 (6)	−0.0027 (13)	−0.003 (4)	−0.0005 (13)
C2	0.026 (4)	0.039 (2)	0.018 (6)	−0.0009 (15)	−0.003 (3)	−0.0028 (14)
C3	0.0348 (15)	0.032 (5)	0.030 (2)	0.000 (2)	0.0054 (15)	0.004 (2)
C4	0.0293 (14)	0.031 (4)	0.0259 (13)	−0.004 (2)	0.0046 (12)	−0.008 (3)
C5	0.0307 (14)	0.032 (4)	0.0262 (13)	−0.004 (2)	0.0033 (12)	−0.007 (3)
C6	0.0344 (14)	0.036 (5)	0.029 (2)	0.000 (2)	0.0044 (14)	0.005 (2)
N1	0.037 (2)	0.048 (2)	0.030 (3)	−0.0035 (15)	−0.002 (2)	0.0005 (14)
N2	0.039 (2)	0.050 (2)	0.032 (3)	−0.0034 (14)	−0.003 (2)	−0.0006 (14)
O1	0.062 (2)	0.044 (2)	0.045 (2)	0.0018 (13)	−0.0112 (13)	0.0134 (13)
O2	0.046 (2)	0.0428 (15)	0.039 (2)	−0.0037 (13)	−0.0018 (13)	−0.0043 (12)
Cl4	0.0433 (14)	0.035 (2)	0.0311 (8)	0.0018 (9)	−0.0018 (8)	0.0026 (9)
Cl5	0.043 (2)	0.038 (2)	0.0303 (9)	−0.0053 (10)	0.0011 (9)	−0.0036 (10)

Geometric parameters (Å, º)

C1—C2	1.403 (7)	C2—N2	1.350 (9)
C2—C3	1.427 (10)	N1—O1	1.237 (5)
C3—C4	1.370 (15)	N1—O2	1.454 (5)
C4—C5	1.472 (6)	N2—O2	1.383 (5)
C5—C6	1.350 (15)	C4—Cl4	1.717 (14)
C1—C6	1.405 (9)	C5—Cl5	1.732 (14)
C1—N1	1.332 (8)
C1···C2^i	0.479 (14)	C6···C3^i	0.34 (2)
C1···C1^i	0.93 (2)	C6···C2^i	1.093 (12)
C1···N2^i	1.546 (10)	C6···C4^i	1.54 (3)
C1···C3^i	1.735 (10)	N1···N2^i	0.678 (4)
C1···N1^i	1.819 (7)	N1···O2^i	0.853 (4)
C2···C1^i	0.479 (14)	N1···C2^i	1.363 (7)
C2···C6^i	1.093 (12)	N1···N1^i	1.654 (8)
C2···N1^i	1.363 (7)	N1···C1^i	1.819 (7)
C2···C2^i	1.873 (14)	N2···N1^i	0.678 (4)
C3···C6^i	0.34 (2)	N2···O1^i	0.865 (4)
C3···C5^i	1.20 (3)	N2···C1^i	1.546 (10)
C3···C1^i	1.735 (10)	O1···N2^i	0.865 (4)
C4···C5^i	0.21 (3)	O1···O2^i	1.470 (4)
C4···C4^i	1.44 (2)	O2···O2^i	0.844 (5)
C4···C6^i	1.54 (3)	O2···N1^i	0.853 (4)
C4···Cl5^i	1.57 (2)	O2···O1^i	1.470 (4)
C5···C4^i	0.21 (3)	Cl4···Cl5^i	0.300 (9)
C5···C3^i	1.20 (3)	Cl4···C5^i	1.90 (2)
C5···C5^i	1.48 (2)	Cl5···Cl4^i	0.300 (9)
C5···Cl4^i	1.90 (2)	Cl5···C4^i	1.57 (2)
C2—C1—C6	126.3 (9)	C6^i—C4—Cl5^i	120.6 (8)
C1—C2—C3	117.1 (9)	C5^i—C4—Cl4	147 (6)
C4—C3—C2	120.3 (11)	C4^i—C4—Cl4	116.6 (4)
C3—C4—C5	117.6 (17)	C6^i—C4—Cl4	129.1 (7)
C6—C5—C4	125.2 (17)	Cl5^i—C4—Cl4	9.2 (3)
C5—C6—C1	113.4 (11)	C4^i—C5—C3^i	143 (6)
N1—C1—C2	108.9 (5)	C4^i—C5—C6	156 (6)
N2—C2—C1	111.2 (5)	C3^i—C5—C6	13.5 (5)
C1—N1—O2	105.2 (4)	C4^i—C5—C4	77 (5)
C2—N2—O2	105.0 (4)	C3^i—C5—C4	138.6 (19)
N2—O2—N1	109.8 (3)	C4^i—C5—C5^i	84 (6)
O1—N1—O2	117.8 (3)	C3^i—C5—C5^i	130.6 (7)
C5—C4—Cl4	124.5 (16)	C6—C5—C5^i	117.2 (6)
C4—C5—Cl5	112.5 (16)	C4—C5—C5^i	8.2 (12)
N1—C1—C6	124.8 (10)	C4^i—C5—Cl5	37 (5)
N2—C2—C3	131.7 (9)	C3^i—C5—Cl5	108.9 (7)
C3—C4—Cl4	117.8 (7)	C5^i—C5—Cl5	120.5 (4)
C6—C5—Cl5	122.3 (7)	C4^i—C5—Cl4^i	30 (5)
O1—N1—C1	137.0 (5)	C3^i—C5—Cl4^i	116.0 (8)
C2^i—C1—C1^i	170 (2)	C6—C5—Cl4^i	129.5 (7)
C2^i—C1—N1	83.4 (16)	C4—C5—Cl4^i	105.2 (15)
C1^i—C1—N1	105.8 (4)	C5^i—C5—Cl4^i	113.1 (4)
C2^i—C1—C2	167.3 (19)	Cl5—C5—Cl4^i	8.0 (3)
C1^i—C1—C2	3.5 (7)	C3^i—C6—C2^i	173 (6)
C2^i—C1—C6	41.5 (14)	C3^i—C6—C5	56 (5)
C1^i—C1—C6	129.4 (8)	C2^i—C6—C5	130.2 (13)
C2^i—C1—N2^i	57.5 (15)	C3^i—C6—C1	168 (5)
C1^i—C1—N2^i	131.6 (3)	C2^i—C6—C1	16.9 (7)
N1—C1—N2^i	25.9 (2)	C3^i—C6—C4^i	53 (5)
C2—C1—N2^i	134.8 (5)	C2^i—C6—C4^i	133.0 (11)
C6—C1—N2^i	98.9 (9)	C5—C6—C4^i	3.2 (9)
C2^i—C1—C3^i	43.6 (12)	C1—C6—C4^i	116.1 (10)
C1^i—C1—C3^i	127.4 (6)	N2^i—N1—O2^i	128.7 (8)
N1—C1—C3^i	126.8 (8)	N2^i—N1—O1	42.2 (5)
C2—C1—C3^i	124.3 (9)	O2^i—N1—O1	87.3 (4)
C6—C1—C3^i	2.3 (11)	N2^i—N1—C1	95.0 (8)
N2^i—C1—C3^i	101.0 (7)	O2^i—N1—C1	135.5 (6)
C2^i—C1—N1^i	144.1 (16)	N2^i—N1—C2^i	74.5 (7)
C1^i—C1—N1^i	44.8 (3)	O2^i—N1—C2^i	155.5 (6)
N1—C1—N1^i	61.0 (4)	O1—N1—C2^i	116.6 (5)
C2—C1—N1^i	47.9 (3)	C1—N1—C2^i	20.5 (6)
C6—C1—N1^i	174.0 (10)	N2^i—N1—O2	159.5 (7)
N2^i—C1—N1^i	86.8 (3)	O2^i—N1—O2	30.8 (3)
C3^i—C1—N1^i	172.1 (8)	C2^i—N1—O2	125.6 (4)
C1^i—C2—C6^i	122 (2)	N2^i—N1—N1^i	167.9 (7)
C1^i—C2—N2	105.1 (14)	O2^i—N1—N1^i	61.5 (3)
C6^i—C2—N2	133.1 (10)	O1—N1—N1^i	148.8 (3)
C1^i—C2—N1^i	76.1 (12)	C1—N1—N1^i	74.2 (4)
C6^i—C2—N1^i	161.8 (11)	C2^i—N1—N1^i	94.6 (3)
N2—C2—N1^i	29.0 (2)	O2—N1—N1^i	31.0 (2)
C1^i—C2—C1	6.9 (15)	N2^i—N1—C1^i	124.2 (8)
C6^i—C2—C1	115.7 (11)	O2^i—N1—C1^i	106.2 (5)
N1^i—C2—C1	82.3 (4)	O1—N1—C1^i	166.4 (5)
C1^i—C2—C3	123.0 (17)	C1—N1—C1^i	29.4 (6)
C6^i—C2—C3	1.6 (13)	C2^i—N1—C1^i	49.8 (3)
N1^i—C2—C3	160.3 (9)	O2—N1—C1^i	75.8 (4)
C1^i—C2—C2^i	9.5 (15)	N1^i—N1—C1^i	44.8 (3)
C6^i—C2—C2^i	112.6 (9)	N1^i—N2—O1^i	106.0 (8)
N2—C2—C2^i	114.3 (3)	N1^i—N2—C2	76.5 (7)
N1^i—C2—C2^i	85.3 (3)	O1^i—N2—C2	175.1 (7)
C1—C2—C2^i	3.2 (4)	N1^i—N2—O2	28.8 (5)
C3—C2—C2^i	114.0 (7)	O1^i—N2—O2	77.9 (4)
C6^i—C3—C5^i	111 (5)	N1^i—N2—C1^i	59.1 (6)
C6^i—C3—C4	116 (6)	O1^i—N2—C1^i	164.6 (5)
C5^i—C3—C4	5.3 (11)	C2—N2—C1^i	17.4 (4)
C6^i—C3—C2	5 (5)	O2—N2—C1^i	87.6 (4)
C5^i—C3—C2	115.3 (8)	N2^i—O1—N1	31.8 (3)
C6^i—C3—C1^i	10 (4)	N2^i—O1—O2^i	67.0 (4)
C5^i—C3—C1^i	102.0 (8)	N1—O1—O2^i	35.5 (2)
C4—C3—C1^i	107.0 (10)	O2^i—O2—N1^i	118.0 (3)
C2—C3—C1^i	13.4 (6)	O2^i—O2—N2	140.5 (2)
C5^i—C4—C3	32 (5)	N1^i—O2—N2	22.5 (3)
C5^i—C4—C4^i	95 (5)	O2^i—O2—N1	31.2 (2)
C3—C4—C4^i	125.6 (6)	N1^i—O2—N1	87.5 (4)
C5^i—C4—C5	88 (6)	O2^i—O2—O1^i	171.7 (5)
C4^i—C4—C5	8.2 (12)	N1^i—O2—O1^i	57.2 (3)
C5^i—C4—C6^i	21 (5)	N2—O2—O1^i	35.1 (2)
C3—C4—C6^i	11.3 (5)	N1—O2—O1^i	144.7 (3)
C4^i—C4—C6^i	114.3 (5)	Cl5^i—Cl4—C4	56 (3)
C5—C4—C6^i	106.4 (15)	Cl5^i—Cl4—C5^i	53 (3)
C5^i—C4—Cl5^i	138 (6)	C4—Cl4—C5^i	3.5 (7)
C3—C4—Cl5^i	109.4 (7)	Cl4^i—Cl5—C4^i	114 (4)
C4^i—C4—Cl5^i	124.9 (5)	Cl4^i—Cl5—C5	119 (4)
C5—C4—Cl5^i	132.9 (17)	C4^i—Cl5—C5	4.7 (8)

Symmetry code: (i) −x+1, y, −z+3/2.

(Crt) 5,6-dichlorobenzfurazan-1-oxide'

Crystal data

C6H2Cl2N2O2	F(000) = 408
Mr = 205.00	Dx = 1.784 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.293 (5) Å	Cell parameters from 25 reflections
b = 9.061 (6) Å	θ = 14–22°
c = 11.618 (2) Å	µ = 0.80 mm^−1
β = 96.12 (3)°	T = 297 K
V = 763.4 (12) Å^3	Thin plate, colorless
Z = 4	0.45 × 0.25 × 0.01 mm

Data collection

CAD-4 diffractometer	472 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.079
Graphite monochromator	θmax = 26°, θmin = 3.5°
ω–2θ scans	h = −8→8
Absorption correction: psi scan North, A. C. T., Phillips, D. C., and Mathews, F. S. (1968). Acta Cryst., A24, 351-359.	k = 0→11
Tmin = 0.82, Tmax = 0.99	l = −14→14
1588 measured reflections	3 standard reflections every 60 min
747 independent reflections	intensity decay: <1

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.136	Idealized positions
S = 0.83	Calculated w = 1/[σ^2(Fo^2) + (0.055P)^2 + 1.03P] where P = (Fo^2 + 2Fc^2)/3
747 reflections	(Δ/σ)max = 0.01
109 parameters	Δρmax = 0.18 e Å^−3
33 restraints	Δρmin = −0.15 e Å^−3

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 on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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)
C1	0.535 (3)	0.2740 (11)	0.7874 (15)	0.054 (4)	0.50
C2	0.437 (3)	0.2859 (12)	0.6764 (13)	0.054 (3)	0.50
C3	0.395 (2)	0.4255 (16)	0.6285 (13)	0.0573 (15)	0.50
H3	0.3439	0.4346	0.5538	0.069*	0.50
C4	0.457 (3)	0.5450 (15)	0.6886 (17)	0.054 (2)	0.50
C5	0.556 (3)	0.5292 (17)	0.8047 (18)	0.054 (2)	0.50
C6	0.592 (2)	0.3975 (15)	0.8548 (14)	0.0574 (15)	0.50
H6	0.6804	0.3901	0.9234	0.069*	0.50
N1	0.5541 (13)	0.1340 (9)	0.8151 (7)	0.066 (2)	0.50
N2	0.3910 (12)	0.1506 (10)	0.6337 (7)	0.067 (2)	0.50
O1	0.6284 (10)	0.0649 (8)	0.8975 (6)	0.090 (2)	0.50
O2	0.4666 (11)	0.0539 (7)	0.7170 (5)	0.077 (2)	0.50
Cl4	0.4143 (12)	0.7193 (10)	0.6324 (7)	0.0662 (10)	0.50
Cl5	0.6147 (12)	0.6891 (10)	0.8805 (6)	0.0642 (9)	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.059 (6)	0.062 (3)	0.043 (11)	−0.015 (4)	0.009 (6)	0.000 (3)
C2	0.059 (6)	0.062 (3)	0.043 (10)	−0.014 (4)	0.008 (6)	0.000 (3)
C3	0.057 (3)	0.065 (5)	0.050 (4)	0.003 (4)	0.005 (3)	0.000 (4)
C4	0.049 (3)	0.065 (3)	0.049 (3)	−0.011 (5)	0.009 (2)	−0.014 (5)
C5	0.049 (3)	0.065 (3)	0.049 (3)	−0.011 (5)	0.008 (2)	−0.015 (5)
C6	0.057 (3)	0.065 (5)	0.050 (4)	0.002 (4)	0.005 (3)	−0.001 (4)
N1	0.060 (5)	0.077 (3)	0.058 (5)	−0.005 (3)	−0.006 (3)	−0.002 (3)
N2	0.061 (5)	0.078 (3)	0.060 (5)	−0.004 (3)	−0.005 (3)	−0.003 (3)
O1	0.106 (5)	0.072 (4)	0.087 (4)	0.004 (4)	−0.012 (4)	0.024 (3)
O2	0.084 (6)	0.072 (3)	0.074 (6)	−0.009 (4)	−0.001 (4)	−0.002 (3)
Cl4	0.075 (2)	0.062 (3)	0.059 (2)	−0.0016 (13)	−0.004 (2)	0.0006 (12)
Cl5	0.073 (2)	0.061 (3)	0.057 (2)	−0.0059 (14)	−0.003 (2)	−0.0042 (13)

Geometric parameters (Å, º)

C1—N1	1.31 (2)	C4—Cl4	1.725 (4)
C1—C6	1.403 (7)	C5—C6	1.341 (6)
C1—C2	1.412 (11)	C5—Cl5	1.725 (4)
C2—N2	1.35 (2)	N1—O1	1.221 (9)
C2—C3	1.403 (7)	N1—O2	1.441 (8)
C3—C4	1.341 (6)	N2—O2	1.376 (9)
C4—C5	1.467 (8)
C1···C2^i	0.46 (3)	C6···C3^i	0.328 (12)
C1···C1^i	0.96 (4)	C6···C2^i	1.09 (2)
C1···N2^i	1.51 (2)	C6···C4^i	1.46 (3)
C1···C3^i	1.73 (2)	N1···N2^i	0.697 (8)
C1···N1^i	1.813 (12)	N1···O2^i	0.823 (7)
C2···C1^i	0.46 (3)	N1···C2^i	1.381 (13)
C2···C6^i	1.09 (2)	N1···N1^i	1.63 (2)
C2···N1^i	1.381 (13)	N1···C1^i	1.813 (12)
C2···C2^i	1.85 (3)	N2···N1^i	0.697 (8)
C3···C6^i	0.328 (12)	N2···O1^i	0.863 (8)
C3···C5^i	1.25 (4)	N2···C1^i	1.51 (2)
C3···C1^i	1.73 (2)	O1···N2^i	0.863 (8)
C4···C5^i	0.19 (3)	O1···O2^i	1.436 (9)
C4···C6^i	1.46 (3)	O2···N1^i	0.823 (7)
C4···C4^i	1.49 (3)	O2···O2^i	0.863 (10)
C4···Cl5^i	1.59 (2)	O2···O1^i	1.436 (9)
C5···C4^i	0.19 (3)	Cl4···Cl5^i	0.368 (8)
C5···C3^i	1.25 (4)	Cl4···C5^i	1.87 (2)
C5···C5^i	1.44 (4)	Cl5···Cl4^i	0.368 (8)
C5···Cl4^i	1.87 (2)	Cl5···C4^i	1.59 (2)
N1—C1—C6	128.1 (17)	C4^i—C4—Cl5^i	124.3 (8)
N1—C1—C2	109.1 (8)	C5^i—C4—Cl4	138 (10)
C6—C1—C2	122.7 (16)	C6^i—C4—Cl4	132.7 (14)
N2—C2—C3	129.7 (14)	C4^i—C4—Cl4	113.7 (6)
N2—C2—C1	110.3 (8)	Cl5^i—C4—Cl4	11.9 (3)
C3—C2—C1	120.0 (15)	C4^i—C5—C3^i	116 (10)
C4—C3—C2	118.3 (12)	C4^i—C5—C6	125 (10)
C3—C4—C5	120.4 (14)	C3^i—C5—C6	13.9 (6)
C3—C4—Cl4	120.2 (10)	C4^i—C5—C5^i	95 (10)
C5—C4—Cl4	119.3 (16)	C3^i—C5—C5^i	130.5 (8)
C6—C5—C4	122.7 (14)	C6—C5—C5^i	116.8 (7)
C6—C5—Cl5	120.0 (10)	C4^i—C5—C4	94 (10)
C5—C6—C1	115.7 (13)	C3^i—C5—C4	136.6 (14)
C4—C5—Cl5	117.2 (17)	C5^i—C5—C4	7.6 (13)
O1—N1—C1	135.6 (11)	C4^i—C5—Cl5	44 (10)
O1—N1—O2	118.9 (6)	C3^i—C5—Cl5	106.0 (11)
C1—N1—O2	105.5 (9)	C5^i—C5—Cl5	122.6 (7)
C2—N2—O2	104.8 (8)	C4^i—C5—Cl4^i	38 (10)
N2—O2—N1	110.2 (6)	C3^i—C5—Cl4^i	115.9 (12)
C2^i—C1—C1^i	166 (4)	C6—C5—Cl4^i	129.8 (11)
C2^i—C1—N1	89 (4)	C5^i—C5—Cl4^i	112.1 (7)
C1^i—C1—N1	104.7 (8)	C4—C5—Cl4^i	107.1 (15)
C2^i—C1—C6	39 (3)	Cl5—C5—Cl4^i	10.7 (4)
C1^i—C1—C6	127.1 (12)	C3^i—C6—C2^i	162 (7)
C2^i—C1—C2	162 (4)	C3^i—C6—C5	66 (7)
C1^i—C1—C2	4.7 (10)	C2^i—C6—C5	131.3 (14)
C2^i—C1—N2^i	62 (3)	C3^i—C6—C1	178 (7)
C1^i—C1—N2^i	132.1 (5)	C2^i—C6—C1	15.6 (15)
N1—C1—N2^i	27.5 (5)	C3^i—C6—C4^i	63 (6)
C6—C1—N2^i	100.8 (15)	C2^i—C6—C4^i	134.7 (19)
C2—C1—N2^i	136.5 (8)	C5—C6—C4^i	6.3 (18)
C2^i—C1—C3^i	39 (3)	C1—C6—C4^i	119.3 (18)
C1^i—C1—C3^i	127.4 (8)	N2^i—N1—O2^i	129.7 (15)
N1—C1—C3^i	127.7 (14)	N2^i—N1—O1	43.6 (9)
C6—C1—C3^i	0.4 (13)	O2^i—N1—O1	87.0 (8)
C2—C1—C3^i	123.1 (15)	N2^i—N1—C1	92.0 (14)
N2^i—C1—C3^i	100.4 (11)	O2^i—N1—C1	137.1 (12)
C2^i—C1—N1^i	149 (4)	N2^i—N1—C2^i	72.8 (13)
C1^i—C1—N1^i	44.5 (6)	O2^i—N1—C2^i	156.5 (12)
N1—C1—N1^i	60.4 (7)	O1—N1—C2^i	116.2 (10)
C6—C1—N1^i	171.5 (16)	C1—N1—C2^i	19.5 (12)
C2—C1—N1^i	48.8 (5)	N2^i—N1—O2	161.6 (13)
N2^i—C1—N1^i	87.7 (6)	O2^i—N1—O2	32.1 (6)
C3^i—C1—N1^i	171.9 (13)	C2^i—N1—O2	124.9 (8)
C1^i—C2—C6^i	125 (4)	N2^i—N1—N1^i	165.7 (14)
C1^i—C2—N2	101 (3)	O2^i—N1—N1^i	62.1 (7)
C6^i—C2—N2	133.6 (15)	O1—N1—N1^i	149.1 (6)
C1^i—C2—N1^i	72 (3)	C1—N1—N1^i	75.2 (8)
C6^i—C2—N1^i	163.1 (17)	C2^i—N1—N1^i	94.7 (7)
N2—C2—N1^i	29.5 (5)	O2—N1—N1^i	30.3 (3)
C1^i—C2—C3	129 (4)	N2^i—N1—C1^i	122.9 (14)
C6^i—C2—C3	4.0 (17)	O2^i—N1—C1^i	106.5 (10)
N1^i—C2—C3	159.1 (15)	O1—N1—C1^i	166.4 (10)
C1^i—C2—C1	10 (3)	C1—N1—C1^i	30.9 (12)
C6^i—C2—C1	116.0 (18)	C2^i—N1—C1^i	50.3 (4)
N1^i—C2—C1	80.9 (7)	O2—N1—C1^i	74.7 (7)
C1^i—C2—C2^i	14 (3)	N1^i—N1—C1^i	44.4 (6)
C6^i—C2—C2^i	111.6 (12)	N1^i—N2—O1^i	102.6 (14)
N2—C2—C2^i	114.7 (6)	N1^i—N2—C2	77.7 (12)
N1^i—C2—C2^i	85.3 (7)	O1^i—N2—C2	174.1 (14)
C3—C2—C2^i	115.6 (10)	N1^i—N2—O2	27.4 (9)
C1—C2—C2^i	4.5 (8)	O1^i—N2—O2	75.9 (8)
C6^i—C3—C5^i	100 (7)	N1^i—N2—C1^i	60.4 (11)
C6^i—C3—C4	105 (6)	O1^i—N2—C1^i	162.8 (11)
C5^i—C3—C4	7.5 (17)	C2—N2—C1^i	17.4 (8)
C6^i—C3—C2	14 (6)	O2—N2—C1^i	87.4 (7)
C5^i—C3—C2	113.4 (13)	N2^i—O1—N1	33.8 (6)
C6^i—C3—C1^i	2 (6)	N2^i—O1—O2^i	68.4 (7)
C5^i—C3—C1^i	101.5 (12)	N1—O1—O2^i	34.9 (4)
C4—C3—C1^i	106.4 (11)	N1^i—O2—O2^i	117.5 (8)
C2—C3—C1^i	11.9 (12)	N1^i—O2—N2	22.9 (7)
C5^i—C4—C3	57 (10)	O2^i—O2—N2	140.3 (5)
C5^i—C4—C6^i	49 (10)	N1^i—O2—O1^i	58.1 (7)
C3—C4—C6^i	12.5 (8)	O2^i—O2—O1^i	173.3 (12)
C5^i—C4—C5	77 (10)	N2—O2—O1^i	35.6 (4)
C6^i—C4—C5	107.9 (10)	N1^i—O2—N1	87.6 (10)
C5^i—C4—C4^i	78 (10)	O2^i—O2—N1	30.4 (3)
C3—C4—C4^i	125.5 (7)	O1^i—O2—N1	145.7 (6)
C6^i—C4—C4^i	113.1 (9)	Cl5^i—Cl4—C4	63 (4)
C5—C4—C4^i	7.5 (12)	Cl5^i—Cl4—C5^i	61 (3)
C5^i—C4—Cl5^i	131 (10)	C4—Cl4—C5^i	3.9 (15)
C3—C4—Cl5^i	108.9 (11)	Cl4^i—Cl5—C4^i	105 (4)
C6^i—C4—Cl5^i	121.3 (14)	Cl4^i—Cl5—C5	109 (4)
C5—C4—Cl5^i	130.3 (16)	C4^i—Cl5—C5	4.9 (15)

Symmetry code: (i) −x+1, y, −z+3/2.

(CPA)

Crystal data

C8H2Cl2O3	F(000) = 432
Mr = 217.00	Dx = 1.803 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.987 (4) Å	Cell parameters from 49 reflections
b = 8.994 (3) Å	θ = 11–29°
c = 7.423 (4) Å	µ = 0.77 mm^−1
β = 92.91 (4)°	T = 297 K
V = 799.2 (6) Å^3	Thick needle, colorless
Z = 4	0.45 × 0.25 × 0.15 mm

Data collection

CAD-4 diffractometer	1041 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.015
Graphite monochromator	θmax = 30°, θmin = 2.8°
ω scans	h = −16→16
Absorption correction: ψ scan North, A. C. T., Phillips, D. C., and Mathews, F. S. (1968). Acta Cryst., A24, 351-359.	k = 0→12
Tmin = 0.76, Tmax = 0.89	l = −10→10
2336 measured reflections	3 standard reflections every 50 min
1171 independent reflections	intensity decay: <1%

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)] = 0.029	Not refined, put in idealized positions
wR(F^2) = 0.085	Calculated w = 1/[σ^2(Fo^2) + (0.036P)^2 + 0.23P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.01
1171 reflections	Δρmax = 0.43 e Å^−3
61 parameters	Δρmin = −0.18 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.146 (7)

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 on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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
C1	0.55276 (9)	0.24651 (14)	0.2933 (2)	0.0378 (3)
C5	0.55436 (10)	0.50873 (14)	0.2914 (2)	0.0384 (3)
C6	0.60860 (9)	0.3765 (2)	0.3361 (2)	0.0403 (3)
H6	0.67966 (9)	0.3757 (2)	0.3926 (2)	0.048*
C7	0.58546 (11)	0.0907 (2)	0.3254 (2)	0.0461 (3)
O1	0.66550 (9)	0.03635 (13)	0.4008 (2)	0.0646 (4)
O2	0.5000	0.0016 (2)	0.2500	0.0565 (4)
Cl5	0.62077 (3)	0.67439 (4)	0.33897 (5)	0.0508 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0330 (5)	0.0360 (6)	0.0438 (6)	0.0011 (4)	−0.0044 (4)	0.0015 (4)
C5	0.0386 (6)	0.0363 (6)	0.0399 (6)	−0.0035 (4)	−0.0005 (4)	−0.0013 (4)
C6	0.0335 (5)	0.0410 (7)	0.0455 (6)	−0.0022 (4)	−0.0063 (4)	−0.0001 (5)
C7	0.0357 (6)	0.0384 (6)	0.0632 (8)	−0.0001 (5)	−0.0082 (5)	0.0031 (5)
O1	0.0467 (6)	0.0461 (6)	0.0983 (9)	0.0035 (5)	−0.0240 (6)	0.0096 (6)
O2	0.0408 (7)	0.0348 (6)	0.0920 (11)	0.000	−0.0150 (7)	0.000
Cl5	0.0513 (2)	0.0386 (2)	0.0622 (3)	−0.00844 (12)	−0.00183 (15)	−0.00561 (13)

Geometric parameters (Å, º)

C1—C6	1.376 (2)	C5—Cl5	1.7176 (13)
C1—C1^i	1.389 (2)	C7—O1	1.191 (2)
C1—C7	1.471 (2)	C7—O2	1.395 (2)
C5—C6	1.388 (2)	O2—C7^i	1.395 (2)
C5—C5^i	1.412 (3)
C6—C1—C1^i	121.83 (7)	C1—C6—C5	117.15 (10)
C6—C1—C7	130.49 (11)	O1—C7—O2	120.69 (14)
C1^i—C1—C7	107.68 (7)	O1—C7—C1	131.96 (13)
C6—C5—C5^i	120.99 (7)	O2—C7—C1	107.34 (11)
C6—C5—Cl5	119.19 (10)	C7^i—O2—C7	109.9 (2)
C5^i—C5—Cl5	119.82 (5)

Symmetry code: (i) −x+1, y, −z+1/2.

(BPA)

Crystal data

C8H2Br2O3	Z = 4
Mr = 305.92	F(000) = 576
Triclinic, C1	Dx = 2.364 Mg m^−3
a = 12.923 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.209 (2) Å	Cell parameters from 25 reflections
c = 7.6280 (15) Å	θ = 13–22°
α = 105.08 (3)°	µ = 9.40 mm^−1
β = 99.20 (3)°	T = 297 K
γ = 81.29 (3)°	Plate, colorless
V = 859.5 (3) Å^3	0.35 × 0.20 × 0.07 mm

Data collection

CAD-4 diffractometer	1284 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.050
Graphite monochromator	θmax = 28°, θmin = 2.7°
ω–2θ scans	h = −16→16
Absorption correction: ψ scan North, A. C. T., Phillips, D. C., and Mathews, F. S. (1968). Acta Cryst., A24, 351-359.	k = −12→12
Tmin = 0.23, Tmax = 0.52	l = −10→10
4009 measured reflections	3 standard reflections every 60 min
2058 independent reflections	intensity decay: <1%

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)] = 0.050	Idealized positions
wR(F^2) = 0.139	Calculated w = 1/[σ^2(Fo^2) + (0.064P)^2 + 0.18P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.01
2057 reflections	Δρmax = 0.80 e Å^−3
119 parameters	Δρmin = −0.74 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0047 (9)

Special details

Experimental. The space group is C-1 for reasons explained in the text. When checkcif reads the file it changes the C-1 to P-1, which is incorrect.

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 on F² for ALL reflections except for 1 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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
C1	0.5553 (5)	0.2655 (8)	0.2842 (9)	0.0378 (14)
C2	0.4529 (5)	0.2683 (8)	0.1995 (10)	0.0399 (15)
C3	0.3955 (5)	0.3988 (8)	0.1619 (9)	0.0368 (14)
H3	0.3259 (5)	0.4010 (8)	0.1070 (9)	0.044*
C4	0.4498 (5)	0.5276 (7)	0.2125 (9)	0.0377 (14)
C5	0.5523 (5)	0.5250 (7)	0.2963 (10)	0.0382 (14)
C6	0.6090 (5)	0.3925 (7)	0.3352 (9)	0.0356 (13)
H6	0.6783 (5)	0.3898 (7)	0.3918 (9)	0.043*
C7	0.5912 (6)	0.1096 (8)	0.3068 (11)	0.044 (2)
C8	0.4208 (6)	0.1150 (8)	0.1613 (11)	0.044 (2)
O1	0.6722 (5)	0.0542 (6)	0.3695 (9)	0.063 (2)
O2	0.5069 (4)	0.0238 (5)	0.2304 (8)	0.0509 (13)
O3	0.3416 (5)	0.0645 (6)	0.0907 (9)	0.061 (2)
Br4	0.37379 (6)	0.70771 (8)	0.16374 (12)	0.0508 (3)
Br5	0.62425 (6)	0.69818 (9)	0.35590 (12)	0.0518 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.031 (3)	0.043 (3)	0.038 (4)	−0.004 (3)	−0.005 (3)	0.013 (3)
C2	0.036 (4)	0.044 (3)	0.039 (4)	−0.002 (3)	0.005 (3)	0.011 (3)
C3	0.027 (3)	0.045 (3)	0.036 (3)	−0.005 (2)	−0.004 (3)	0.009 (3)
C4	0.038 (4)	0.035 (3)	0.040 (4)	0.002 (3)	0.004 (3)	0.013 (3)
C5	0.039 (4)	0.038 (3)	0.036 (4)	−0.008 (3)	−0.001 (3)	0.008 (3)
C6	0.027 (3)	0.038 (3)	0.039 (4)	−0.004 (2)	−0.002 (3)	0.007 (3)
C7	0.045 (4)	0.038 (3)	0.047 (4)	−0.006 (3)	0.000 (3)	0.010 (3)
C8	0.035 (4)	0.042 (3)	0.052 (5)	−0.004 (3)	0.002 (3)	0.011 (3)
O1	0.050 (3)	0.050 (3)	0.081 (4)	0.001 (2)	−0.020 (3)	0.024 (3)
O2	0.040 (3)	0.037 (2)	0.068 (4)	−0.006 (2)	−0.013 (3)	0.012 (2)
O3	0.045 (3)	0.052 (3)	0.082 (4)	−0.018 (2)	−0.017 (3)	0.019 (3)
Br4	0.0495 (5)	0.0434 (4)	0.0597 (6)	0.0052 (3)	0.0031 (4)	0.0211 (4)
Br5	0.0517 (5)	0.0473 (4)	0.0586 (5)	−0.0184 (3)	0.0002 (4)	0.0137 (3)

Geometric parameters (Å, º)

C1—C2	1.376 (9)	C4—Br4	1.888 (6)
C1—C6	1.386 (9)	C5—C6	1.401 (9)
C1—C7	1.486 (9)	C5—Br5	1.885 (7)
C2—C3	1.385 (9)	C7—O1	1.179 (9)
C2—C8	1.476 (10)	C7—O2	1.403 (9)
C3—C4	1.405 (9)	C8—O3	1.179 (9)
C4—C5	1.376 (9)	C8—O2	1.408 (8)
C2—C1—C6	122.4 (6)	C4—C5—Br5	121.3 (5)
C2—C1—C7	108.0 (6)	C6—C5—Br5	117.1 (5)
C6—C1—C7	129.6 (6)	C1—C6—C5	115.9 (6)
C1—C2—C3	122.4 (7)	O1—C7—O2	121.2 (6)
C1—C2—C8	108.5 (6)	O1—C7—C1	132.1 (7)
C3—C2—C8	129.1 (7)	O2—C7—C1	106.8 (6)
C2—C3—C4	115.4 (6)	O3—C8—O2	120.9 (7)
C5—C4—C3	122.3 (6)	O3—C8—C2	132.3 (7)
C5—C4—Br4	121.1 (5)	O2—C8—C2	106.8 (6)
C3—C4—Br4	116.6 (5)	C7—O2—C8	110.0 (5)
C4—C5—C6	121.6 (6)