5-Chloro- and 5-bromobenzfurazan 1-oxide revisited

At room temperature the two title compounds are isomorphous. Both have a disordered structure that includes a major component, one of the title compounds, and a minor component, the 6-halo isomer, occurring at the same site in the crystal. When the chloro compound is cooled to as low as 98 K, there is no change in the structure and no significant change in the degree of disorder. When the bromo compound is cooled, it undergoes a second-order phase transition at 282 K to a second polymorph, structurally very similar, but with two molecules in the asymmetric unit. In both isomorphs and both polymorphs the molecules occur in two-dimensional layers that are essentially the same. In the low-temperature form of the bromo compound the layers have shifted relative to each other by approximately 0.7 Å in y. In the low-temperature form the disorder, which is still present after the transition, decreases as the temperature is lowered.

Computing details

For all compounds, data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1994); program(s) used to refine structure: SHELXLTL; molecular graphics: SHELXLTL; software used to prepare material for publication: SHELXLTL.

(Cl273K) 5-chlorobenzfurazan-1-oxide

Crystal data

C6H3ClN2O2	F(000) = 344
Mr = 170.55	Dx = 1.627 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.973 (2) Å	Cell parameters from 449 reflections
b = 7.0579 (15) Å	θ = 2.9–17.4°
c = 12.389 (3) Å	µ = 0.49 mm^−1
β = 92.683 (4)°	T = 273 K
V = 696.4 (3) Å^3	Prism, yellow
Z = 4	0.50 × 0.32 × 0.21 mm

Data collection

Siemens SMART area-detector diffractometer	1231 independent reflections
Radiation source: fine-focus sealed tube	620 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω scans	θmax = 25.1°, θmin = 3.0°
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995	h = −9→9
Tmin = 0.84, Tmax = 0.90	k = −8→7
3550 measured reflections	l = −14→14

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.087	H-atom parameters constrained
S = 0.88	w = 1/[σ^2(Fo^2) + (0.037P)^2] where P = (Fo^2 + 2Fc^2)/3
1231 reflections	(Δ/σ)max = 0.003
165 parameters	Δρmax = 0.13 e Å^−3
28 restraints	Δρmin = −0.10 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.8996 (5)	0.2540 (5)	0.8705 (2)	0.1009 (8)	0.779 (5)
O1	0.5425 (7)	−0.4514 (5)	1.1476 (5)	0.137 (2)	0.779 (5)
O2	0.5596 (7)	−0.1581 (9)	1.2315 (4)	0.107 (2)	0.779 (5)
N1	0.5843 (10)	−0.2830 (10)	1.1423 (5)	0.098 (2)	0.779 (5)
N2	0.6212 (6)	0.0153 (6)	1.2083 (4)	0.0950 (13)	0.779 (5)
C1	0.6610 (6)	−0.1806 (6)	1.0673 (3)	0.0717 (11)	0.779 (5)
C2	0.6791 (8)	0.0003 (6)	1.1103 (3)	0.0665 (11)	0.779 (5)
C3	0.7544 (13)	0.1427 (7)	1.0482 (4)	0.0696 (10)	0.779 (5)
H3	0.7683 (13)	0.2659 (7)	1.0737 (4)	0.083*	0.779 (5)
C4	0.805 (3)	0.0905 (10)	0.9502 (9)	0.0659 (12)	0.779 (5)
C5	0.783 (3)	−0.0944 (10)	0.9079 (8)	0.0789 (8)	0.779 (5)
H5	0.820 (3)	−0.1220 (10)	0.8396 (8)	0.095*	0.779 (5)
C6	0.7103 (9)	−0.2306 (7)	0.9648 (4)	0.0852 (11)	0.779 (5)
H6	0.6934 (9)	−0.3521 (7)	0.9372 (4)	0.102*	0.779 (5)
Cl11	0.8724 (19)	0.2889 (17)	0.9041 (11)	0.124 (4)	0.221 (5)
O11	0.569 (2)	−0.0405 (19)	1.2695 (8)	0.133 (8)	0.221 (5)
O12	0.555 (3)	−0.3286 (17)	1.1797 (10)	0.097 (8)	0.221 (5)
N11	0.598 (3)	−0.1315 (19)	1.1871 (9)	0.089 (9)	0.221 (5)
N12	0.5951 (18)	−0.3949 (14)	1.0815 (8)	0.096 (5)	0.221 (5)
C11	0.669 (4)	−0.0859 (16)	1.0940 (13)	0.0665 (11)	0.221 (5)
C12	0.665 (3)	−0.2503 (15)	1.0325 (10)	0.0717 (11)	0.221 (5)
C13	0.737 (4)	−0.2480 (19)	0.9301 (13)	0.0852 (11)	0.221 (5)
H13	0.745 (4)	−0.3572 (19)	0.8887 (13)	0.102*	0.221 (5)
C14	0.793 (9)	−0.079 (3)	0.896 (3)	0.0789 (8)	0.221 (5)
H14	0.836 (9)	−0.073 (3)	0.828 (3)	0.095*	0.221 (5)
C15	0.789 (10)	0.088 (3)	0.958 (3)	0.0659 (12)	0.221 (5)
C16	0.733 (5)	0.086 (2)	1.0588 (16)	0.0696 (10)	0.221 (5)
H16	0.737 (5)	0.193 (2)	1.1026 (16)	0.083*	0.221 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0811 (11)	0.131 (2)	0.0906 (12)	−0.0015 (11)	0.0049 (9)	0.0420 (12)
O1	0.125 (3)	0.130 (4)	0.156 (4)	−0.042 (3)	−0.005 (3)	0.035 (4)
O2	0.086 (3)	0.167 (6)	0.069 (4)	0.007 (4)	0.018 (3)	0.023 (3)
N1	0.074 (3)	0.124 (5)	0.093 (4)	−0.008 (4)	−0.016 (4)	0.029 (5)
N2	0.091 (3)	0.124 (3)	0.071 (3)	0.015 (3)	0.012 (2)	0.004 (3)
C1	0.052 (2)	0.100 (4)	0.062 (3)	−0.003 (4)	−0.003 (3)	0.008 (3)
C2	0.057 (2)	0.098 (4)	0.045 (2)	0.015 (3)	0.000 (2)	−0.001 (2)
C3	0.070 (3)	0.072 (3)	0.066 (2)	0.008 (3)	−0.002 (2)	−0.002 (2)
C4	0.049 (5)	0.088 (2)	0.060 (2)	0.0016 (14)	−0.0018 (14)	0.011 (2)
C5	0.065 (3)	0.109 (3)	0.063 (3)	0.003 (2)	0.007 (2)	−0.012 (2)
C6	0.078 (4)	0.083 (2)	0.093 (4)	−0.001 (2)	−0.006 (3)	−0.020 (2)
Cl11	0.104 (6)	0.102 (4)	0.166 (10)	−0.012 (4)	0.010 (5)	0.032 (5)
O11	0.144 (12)	0.193 (18)	0.066 (9)	0.073 (13)	0.038 (8)	−0.012 (9)
O12	0.104 (13)	0.098 (17)	0.088 (12)	0.008 (13)	0.017 (10)	0.023 (12)
N11	0.070 (13)	0.14 (3)	0.054 (12)	0.038 (15)	0.011 (9)	−0.013 (15)
N12	0.086 (9)	0.108 (13)	0.095 (10)	−0.015 (8)	0.014 (8)	0.033 (8)
C11	0.057 (2)	0.098 (4)	0.045 (2)	0.015 (3)	0.000 (2)	−0.001 (2)
C12	0.052 (2)	0.100 (4)	0.062 (3)	−0.003 (4)	−0.003 (3)	0.008 (3)
C13	0.078 (4)	0.083 (2)	0.093 (4)	−0.001 (2)	−0.006 (3)	−0.020 (2)
C14	0.065 (3)	0.109 (3)	0.063 (3)	0.003 (2)	0.007 (2)	−0.012 (2)
C15	0.049 (5)	0.088 (2)	0.060 (2)	0.0016 (14)	−0.0018 (14)	0.011 (2)
C16	0.070 (3)	0.072 (3)	0.066 (2)	0.008 (3)	−0.002 (2)	−0.002 (2)

Geometric parameters (Å, º)

Cl1—C4	1.717 (2)	Cl11—C15	1.717 (3)
O1—N1	1.237 (8)	O11—N11	1.237 (8)
O2—N2	1.355 (7)	O12—N12	1.355 (7)
O2—N1	1.434 (5)	O12—N11	1.435 (5)
N1—C1	1.347 (8)	N11—C11	1.347 (8)
N2—C2	1.324 (6)	N12—C12	1.324 (6)
C1—C2	1.388 (4)	C11—C12	1.388 (5)
C1—C6	1.393 (5)	C11—C16	1.393 (5)
C2—C3	1.416 (5)	C12—C13	1.416 (5)
C3—C4	1.347 (4)	C13—C14	1.347 (5)
C4—C5	1.415 (3)	C14—C15	1.415 (4)
C5—C6	1.340 (5)	C15—C16	1.341 (5)
N2—O2—N1	109.1 (3)	N12—O12—N11	109.1 (4)
O1—N1—C1	133.2 (6)	O11—N11—C11	133.3 (6)
O1—N1—O2	120.2 (6)	O11—N11—O12	120.2 (6)
C1—N1—O2	106.6 (4)	C11—N11—O12	106.6 (4)
C2—N2—O2	105.5 (4)	C12—N12—O12	105.5 (5)
N1—C1—C2	105.7 (4)	N11—C11—C12	105.7 (4)
N1—C1—C6	130.5 (5)	N11—C11—C16	130.6 (5)
C2—C1—C6	123.7 (4)	C12—C11—C16	123.7 (4)
N2—C2—C1	113.0 (4)	N12—C12—C11	113.0 (4)
N2—C2—C3	128.1 (4)	N12—C12—C13	128.1 (4)
C1—C2—C3	118.9 (3)	C11—C12—C13	118.9 (4)
C4—C3—C2	116.6 (3)	C14—C13—C12	116.5 (4)
C3—C4—C5	123.3 (3)	C13—C14—C15	123.3 (4)
C3—C4—Cl1	119.5 (3)	C16—C15—C14	121.0 (4)
C5—C4—Cl1	117.2 (2)	C16—C15—Cl11	121.7 (8)
C6—C5—C4	121.1 (4)	C14—C15—Cl11	117.1 (3)
C5—C6—C1	116.4 (4)	C15—C16—C11	116.4 (4)

(Cl98K) 5-chlorobenzfurazan-1-oxide

Crystal data

C6H3ClN2O2	F(000) = 344
Mr = 170.55	Dx = 1.677 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.8317 (10) Å	Cell parameters from 1621 reflections
b = 7.0527 (9) Å	θ = 3.0–25.0°
c = 12.2576 (15) Å	µ = 0.51 mm^−1
β = 93.612 (2)°	T = 98 K
V = 675.70 (15) Å^3	Prism, yellow
Z = 4	0.26 × 0.24 × 0.22 mm

Data collection

Siemens SMART area-detector diffractometer	1199 independent reflections
Radiation source: fine-focus sealed tube	971 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω scans	θmax = 25.1°, θmin = 3.0°
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995	h = −9→5
Tmin = 0.87, Tmax = 0.89	k = −8→7
3517 measured reflections	l = −14→14

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) = 0.103	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.062P)^2 + 0.113P] where P = (Fo^2 + 2Fc^2)/3
1199 reflections	(Δ/σ)max = 0.013
165 parameters	Δρmax = 0.26 e Å^−3
28 restraints	Δρmin = −0.20 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.8966 (5)	0.2572 (4)	0.8685 (3)	0.0562 (7)	0.789 (4)
O1	0.5451 (3)	−0.4599 (4)	1.1480 (3)	0.0736 (9)	0.789 (4)
O2	0.5587 (3)	−0.1674 (4)	1.2318 (2)	0.0527 (7)	0.789 (4)
N1	0.5888 (5)	−0.2928 (5)	1.1415 (3)	0.0472 (9)	0.789 (4)
N2	0.6163 (3)	0.0127 (4)	1.2088 (2)	0.0474 (7)	0.789 (4)
C1	0.6627 (4)	−0.1862 (4)	1.0668 (2)	0.0363 (7)	0.789 (4)
C2	0.6776 (4)	−0.0023 (4)	1.1104 (2)	0.0351 (7)	0.789 (4)
C3	0.7511 (6)	0.1441 (4)	1.0484 (3)	0.0366 (7)	0.789 (4)
H3	0.7601 (6)	0.2686 (4)	1.0732 (3)	0.044*	0.789 (4)
C4	0.8068 (9)	0.0897 (5)	0.9510 (4)	0.0343 (10)	0.789 (4)
C5	0.7893 (16)	−0.0966 (6)	0.9064 (4)	0.0414 (9)	0.789 (4)
H5	0.8273 (16)	−0.1222 (6)	0.8375 (4)	0.050*	0.789 (4)
C6	0.7177 (5)	−0.2358 (4)	0.9637 (3)	0.0462 (8)	0.789 (4)
H6	0.7055 (5)	−0.3583 (4)	0.9363 (3)	0.055*	0.789 (4)
Cl11	0.8808 (18)	0.2834 (12)	0.8960 (9)	0.058 (3)	0.211 (4)
O11	0.5628 (11)	−0.0397 (11)	1.2681 (5)	0.063 (3)	0.211 (4)
O12	0.5499 (16)	−0.3268 (9)	1.1782 (6)	0.055 (4)	0.211 (4)
N11	0.5946 (11)	−0.1277 (10)	1.1849 (5)	0.046 (3)	0.211 (4)
N12	0.5984 (10)	−0.4001 (8)	1.0803 (5)	0.044 (2)	0.211 (4)
C11	0.6680 (18)	−0.0863 (8)	1.0918 (6)	0.0351 (7)	0.211 (4)
C12	0.6681 (16)	−0.2544 (8)	1.0304 (6)	0.0363 (7)	0.211 (4)
C13	0.734 (2)	−0.2532 (12)	0.9248 (8)	0.0462 (8)	0.211 (4)
H13	0.740 (2)	−0.3622 (12)	0.8824 (8)	0.055*	0.211 (4)
C14	0.789 (6)	−0.083 (2)	0.8904 (18)	0.0414 (9)	0.211 (4)
H14	0.835 (6)	−0.077 (2)	0.8224 (18)	0.050*	0.211 (4)
C15	0.780 (4)	0.0897 (16)	0.9508 (13)	0.0343 (10)	0.211 (4)
C16	0.732 (3)	0.0868 (11)	1.0546 (9)	0.0366 (7)	0.211 (4)
H16	0.741 (3)	0.1936 (11)	1.0992 (9)	0.044*	0.211 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0384 (6)	0.0792 (13)	0.0506 (11)	−0.0013 (8)	−0.0012 (7)	0.0284 (9)
O1	0.058 (2)	0.064 (2)	0.097 (2)	−0.0210 (14)	−0.0043 (14)	0.024 (2)
O2	0.0394 (13)	0.078 (2)	0.042 (2)	0.0052 (13)	0.0072 (11)	0.0177 (14)
N1	0.033 (2)	0.055 (2)	0.053 (2)	−0.0026 (13)	−0.004 (2)	0.008 (2)
N2	0.0436 (14)	0.063 (2)	0.0364 (15)	0.0123 (13)	0.0074 (11)	0.0022 (13)
C1	0.0252 (11)	0.047 (2)	0.036 (2)	0.001 (2)	−0.0007 (13)	0.0049 (13)
C2	0.0258 (11)	0.054 (2)	0.0249 (12)	0.0099 (15)	0.0002 (10)	0.0005 (12)
C3	0.034 (2)	0.039 (2)	0.0362 (12)	0.007 (2)	−0.0026 (9)	−0.0034 (13)
C4	0.017 (3)	0.0535 (13)	0.0318 (10)	0.0040 (10)	−0.0030 (10)	0.0060 (8)
C5	0.0312 (10)	0.062 (2)	0.030 (2)	0.0059 (14)	−0.002 (2)	−0.0073 (14)
C6	0.039 (2)	0.0482 (15)	0.051 (3)	−0.0010 (12)	−0.007 (2)	−0.0142 (13)
Cl11	0.052 (4)	0.042 (2)	0.076 (7)	−0.014 (2)	−0.016 (4)	0.017 (3)
O11	0.077 (6)	0.070 (7)	0.044 (5)	0.038 (5)	0.028 (5)	0.012 (5)
O12	0.042 (7)	0.072 (9)	0.052 (7)	0.010 (6)	0.011 (4)	0.029 (6)
N11	0.033 (5)	0.075 (9)	0.032 (6)	0.027 (6)	0.008 (4)	0.023 (6)
N12	0.035 (5)	0.043 (5)	0.053 (6)	−0.009 (4)	−0.001 (4)	0.006 (5)
C11	0.0258 (11)	0.054 (2)	0.0249 (12)	0.0099 (15)	0.0002 (10)	0.0005 (12)
C12	0.0252 (11)	0.047 (2)	0.036 (2)	0.001 (2)	−0.0007 (13)	0.0049 (13)
C13	0.039 (2)	0.0482 (15)	0.051 (3)	−0.0010 (12)	−0.007 (2)	−0.0142 (13)
C14	0.0312 (10)	0.062 (2)	0.030 (2)	0.0059 (14)	−0.002 (2)	−0.0073 (14)
C15	0.017 (3)	0.0535 (13)	0.0318 (10)	0.0040 (10)	−0.0030 (10)	0.0060 (8)
C16	0.034 (2)	0.039 (2)	0.0362 (12)	0.007 (2)	−0.0026 (9)	−0.0034 (13)

Geometric parameters (Å, º)

Cl1—C4	1.733 (3)	Cl11—C15	1.733 (3)
O1—N1	1.232 (4)	O11—N11	1.232 (4)
O2—N2	1.383 (4)	O12—N12	1.382 (4)
O2—N1	1.448 (4)	O12—N11	1.448 (4)
N1—C1	1.343 (5)	N11—C11	1.343 (5)
N2—C2	1.330 (4)	N12—C12	1.330 (4)
C1—C2	1.404 (4)	C11—C12	1.404 (4)
C1—C6	1.406 (4)	C11—C16	1.406 (5)
C2—C3	1.425 (4)	C12—C13	1.425 (4)
C3—C4	1.352 (4)	C13—C14	1.352 (4)
C4—C5	1.427 (3)	C14—C15	1.427 (4)
C5—C6	1.349 (4)	C15—C16	1.351 (5)
N2—O2—N1	109.5 (2)	N12—O12—N11	109.5 (2)
O1—N1—C1	135.5 (4)	O11—N11—C11	135.6 (4)
O1—N1—O2	118.4 (3)	O11—N11—O12	118.4 (4)
C1—N1—O2	106.1 (2)	C11—N11—O12	106.1 (3)
C2—N2—O2	104.7 (3)	C12—N12—O12	104.7 (3)
N1—C1—C2	106.7 (3)	N11—C11—C12	106.7 (3)
N1—C1—C6	130.1 (3)	N11—C11—C16	130.1 (3)
C2—C1—C6	123.3 (3)	C12—C11—C16	123.2 (3)
N2—C2—C1	113.1 (3)	N12—C12—C11	113.1 (3)
N2—C2—C3	127.3 (3)	N12—C12—C13	127.2 (3)
C1—C2—C3	119.6 (2)	C11—C12—C13	119.6 (3)
C4—C3—C2	115.4 (2)	C14—C13—C12	115.4 (3)
C3—C4—C5	124.9 (3)	C13—C14—C15	124.8 (4)
C3—C4—Cl1	119.2 (2)	C16—C15—C14	120.0 (4)
C5—C4—Cl1	115.9 (2)	C16—C15—Cl11	122.5 (7)
C6—C5—C4	120.2 (3)	C14—C15—Cl11	115.7 (3)
C5—C6—C1	116.6 (3)	C15—C16—C11	116.4 (3)

(Br299K) 5-bromobenzfurazan-1-oxide (high temperature polymorph)

Crystal data

C6H3BrN2O2	F(000) = 416
Mr = 215.01	Dx = 1.957 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.954 (4) Å	Cell parameters from 1671 reflections
b = 7.297 (3) Å	θ = 2.8–21.7°
c = 12.574 (6) Å	µ = 5.58 mm^−1
β = 90.124 (8)°	T = 299 K
V = 729.9 (6) Å^3	Prism, yellow
Z = 4	0.35 × 0.20 × 0.10 mm

Data collection

Siemens SMART area-detector diffractometer	1650 independent reflections
Radiation source: fine-focus sealed tube	896 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995	h = −10→10
Tmin = 0.30, Tmax = 0.57	k = −9→9
5494 measured reflections	l = −16→16

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)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.139	w = 1/[σ^2(Fo^2) + (0.084P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.95	(Δ/σ)max = 0.001
1650 reflections	Δρmax = 0.57 e Å^−3
135 parameters	Δρmin = −0.54 e Å^−3
36 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0127 (25)

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1	0.40169 (14)	0.76941 (15)	0.36946 (15)	0.0922 (4)	0.857 (5)
O1	0.0493 (7)	0.0340 (9)	0.6392 (5)	0.142 (2)	0.857 (5)
O2	0.0594 (6)	0.3111 (9)	0.7296 (4)	0.118 (2)	0.857 (5)
N1	0.0892 (7)	0.1957 (9)	0.6366 (5)	0.097 (2)	0.857 (5)
N2	0.1144 (7)	0.4856 (8)	0.7113 (4)	0.099 (2)	0.857 (5)
C1	0.1594 (7)	0.3087 (8)	0.5650 (5)	0.074 (2)	0.857 (5)
C2	0.1737 (7)	0.4806 (8)	0.6115 (4)	0.0729 (15)	0.857 (5)
C3	0.2474 (9)	0.6255 (9)	0.5540 (5)	0.0750 (14)	0.857 (5)
H3	0.2578 (9)	0.7425 (9)	0.5826 (5)	0.090*	0.857 (5)
C4	0.3018 (5)	0.5856 (7)	0.4553 (4)	0.0653 (14)	0.857 (5)
C5	0.2819 (13)	0.4104 (7)	0.4094 (5)	0.0758 (14)	0.857 (5)
H5	0.3180 (13)	0.3929 (7)	0.3398 (5)	0.091*	0.857 (5)
C6	0.2146 (10)	0.2703 (8)	0.4599 (6)	0.087 (2)	0.857 (5)
H6	0.2041 (10)	0.1550 (8)	0.4291 (6)	0.104*	0.857 (5)
Br11	0.3747 (9)	0.7910 (10)	0.4095 (7)	0.0922 (4)	0.143 (5)
O11	0.078 (4)	0.440 (4)	0.7741 (14)	0.118 (2)	0.143 (5)
O12	0.063 (5)	0.164 (3)	0.6823 (17)	0.142 (2)	0.143 (5)
N11	0.105 (5)	0.358 (3)	0.6911 (15)	0.099 (2)	0.143 (5)
N12	0.097 (4)	0.101 (2)	0.5824 (17)	0.097 (2)	0.143 (5)
C11	0.168 (3)	0.402 (2)	0.5953 (13)	0.0729 (15)	0.143 (5)
C12	0.168 (4)	0.2448 (18)	0.5332 (15)	0.074 (2)	0.143 (5)
C13	0.229 (6)	0.252 (2)	0.4282 (18)	0.087 (2)	0.143 (5)
H13	0.234 (6)	0.148 (2)	0.3855 (18)	0.104*	0.143 (5)
C14	0.280 (7)	0.418 (3)	0.393 (2)	0.0758 (14)	0.143 (5)
H14	0.332 (7)	0.426 (3)	0.327 (2)	0.091*	0.143 (5)
C15	0.257 (4)	0.579 (2)	0.4538 (16)	0.0653 (14)	0.143 (5)
C16	0.216 (6)	0.577 (2)	0.5554 (19)	0.0750 (14)	0.143 (5)
H16	0.219 (6)	0.681 (2)	0.5976 (19)	0.090*	0.143 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0815 (5)	0.1139 (6)	0.0813 (8)	0.0031 (3)	0.0003 (5)	0.0274 (5)
O1	0.122 (4)	0.135 (5)	0.170 (6)	−0.037 (4)	−0.008 (3)	0.039 (4)
O2	0.088 (3)	0.185 (6)	0.083 (4)	0.002 (4)	0.007 (3)	0.040 (4)
N1	0.076 (3)	0.108 (4)	0.107 (5)	0.000 (3)	−0.009 (3)	0.021 (3)
N2	0.094 (3)	0.132 (5)	0.071 (3)	0.020 (3)	0.014 (2)	0.010 (3)
C1	0.053 (2)	0.095 (4)	0.073 (4)	0.000 (3)	−0.002 (2)	0.011 (3)
C2	0.059 (2)	0.103 (5)	0.056 (3)	0.021 (3)	0.001 (2)	0.003 (3)
C3	0.070 (4)	0.086 (4)	0.069 (3)	0.012 (3)	−0.010 (2)	−0.013 (3)
C4	0.039 (3)	0.099 (3)	0.058 (2)	0.008 (2)	−0.003 (2)	0.001 (2)
C5	0.065 (2)	0.106 (4)	0.057 (3)	0.012 (2)	0.005 (3)	−0.012 (3)
C6	0.082 (3)	0.088 (3)	0.090 (5)	0.000 (3)	−0.003 (3)	−0.019 (3)
Br11	0.0815 (5)	0.1139 (6)	0.0813 (8)	0.0031 (3)	0.0003 (5)	0.0274 (5)
O11	0.088 (3)	0.185 (6)	0.083 (4)	0.002 (4)	0.007 (3)	0.040 (4)
O12	0.122 (4)	0.135 (5)	0.170 (6)	−0.037 (4)	−0.008 (3)	0.039 (4)
N11	0.094 (3)	0.132 (5)	0.071 (3)	0.020 (3)	0.014 (2)	0.010 (3)
N12	0.076 (3)	0.108 (4)	0.107 (5)	0.000 (3)	−0.009 (3)	0.021 (3)
C11	0.059 (2)	0.103 (5)	0.056 (3)	0.021 (3)	0.001 (2)	0.003 (3)
C12	0.053 (2)	0.095 (4)	0.073 (4)	0.000 (3)	−0.002 (2)	0.011 (3)
C13	0.082 (3)	0.088 (3)	0.090 (5)	0.000 (3)	−0.003 (3)	−0.019 (3)
C14	0.065 (2)	0.106 (4)	0.057 (3)	0.012 (2)	0.005 (3)	−0.012 (3)
C15	0.039 (3)	0.099 (3)	0.058 (2)	0.008 (2)	−0.003 (2)	0.001 (2)
C16	0.070 (4)	0.086 (4)	0.069 (3)	0.012 (3)	−0.010 (2)	−0.013 (3)

Geometric parameters (Å, º)

Br1—C4	1.897 (5)	Br11—C15	1.896 (5)
O1—N1	1.222 (8)	O11—N11	1.222 (8)
O2—N2	1.366 (7)	O12—N12	1.366 (7)
O2—N1	1.461 (8)	O12—N11	1.461 (8)
N1—C1	1.343 (9)	N11—C11	1.343 (9)
N2—C2	1.342 (7)	N12—C12	1.342 (7)
C1—C2	1.388 (8)	C11—C12	1.388 (8)
C1—C6	1.422 (9)	C11—C16	1.423 (9)
C2—C3	1.410 (8)	C12—C13	1.410 (8)
C3—C4	1.347 (7)	C13—C14	1.349 (7)
C4—C5	1.412 (6)	C14—C15	1.413 (6)
C5—C6	1.317 (8)	C15—C16	1.319 (8)
N2—O2—N1	110.5 (4)	N12—O12—N11	110.5 (4)
O1—N1—C1	136.0 (7)	O11—N11—C11	135.9 (7)
O1—N1—O2	119.5 (6)	O11—N11—O12	119.6 (6)
C1—N1—O2	104.5 (6)	C11—N11—O12	104.5 (6)
C2—N2—O2	104.2 (5)	C12—N12—O12	104.1 (5)
N1—C1—C2	107.8 (6)	N11—C11—C12	107.8 (6)
N1—C1—C6	129.2 (6)	N11—C11—C16	129.1 (6)
C2—C1—C6	123.0 (6)	C12—C11—C16	122.9 (6)
N2—C2—C1	112.9 (5)	N12—C12—C11	112.9 (6)
N2—C2—C3	127.4 (5)	N12—C12—C13	127.3 (6)
C1—C2—C3	119.7 (5)	C11—C12—C13	119.7 (5)
C4—C3—C2	116.5 (5)	C14—C13—C12	116.3 (5)
C3—C4—C5	122.5 (5)	C13—C14—C15	122.1 (5)
C3—C4—Br1	120.5 (4)	C16—C15—C14	123.1 (6)
C5—C4—Br1	117.0 (3)	C16—C15—Br11	114.5 (11)
C6—C5—C4	123.4 (5)	C14—C15—Br11	117.2 (4)
C5—C6—C1	115.0 (5)	C15—C16—C11	114.7 (5)

(Br173K) 5-bromobenzfurazan-1-oxide (low temperature polymorph)

Crystal data

C6H3BrN2O2	F(000) = 832
Mr = 215.01	Dx = 2.021 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.5294 (3) Å	Cell parameters from 4919 reflections
b = 7.4121 (2) Å	θ = 3.1–31.9°
c = 14.5587 (3) Å	µ = 5.76 mm^−1
β = 115.676 (1)°	T = 173 K
V = 1413.06 (6) Å^3	Prism, yellow
Z = 8	0.45 × 0.31 × 0.18 mm

Data collection

Siemens SMART area-detector diffractometer	5442 independent reflections
Radiation source: fine-focus sealed tube	3583 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
ω scans	θmax = 33.5°, θmin = 1.6°
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995	h = −22→22
Tmin = 0.13, Tmax = 0.35	k = −10→11
25565 measured reflections	l = −22→18

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)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.075	w = 1/[σ^2(Fo^2) + (0.039P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.95	(Δ/σ)max = 0.004
5442 reflections	Δρmax = 0.61 e Å^−3
268 parameters	Δρmin = −0.77 e Å^−3
72 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0076 (4)

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1	−0.01860 (2)	−0.33333 (3)	0.111500 (14)	0.03614 (8)	0.9895 (6)
O11	0.28454 (11)	0.4120 (2)	0.14070 (12)	0.0545 (4)	0.9895 (6)
O12	0.33169 (10)	0.1432 (2)	0.09518 (11)	0.0424 (3)	0.9895 (6)
N11	0.26550 (12)	0.2506 (2)	0.12524 (12)	0.0362 (4)	0.9895 (6)
N12	0.29807 (11)	−0.0330 (2)	0.08084 (12)	0.0400 (4)	0.9895 (6)
C11	0.19595 (13)	0.1369 (2)	0.12850 (12)	0.0293 (4)	0.9895 (6)
C12	0.21732 (12)	−0.0349 (2)	0.10076 (12)	0.0285 (4)	0.9895 (6)
C13	0.15341 (12)	−0.1854 (2)	0.09652 (12)	0.0294 (4)	0.9895 (6)
H13	0.16580 (12)	−0.3034 (2)	0.07894 (12)	0.035*	0.9895 (6)
C14	0.07482 (11)	−0.1486 (2)	0.11906 (12)	0.0266 (3)	0.9895 (6)
C15	0.05452 (12)	0.0265 (2)	0.14852 (13)	0.0330 (4)	0.9895 (6)
H15	−0.00164 (12)	0.0418 (2)	0.16480 (13)	0.040*	0.9895 (6)
C16	0.11402 (14)	0.1700 (3)	0.15345 (14)	0.0358 (4)	0.9895 (6)
H16	0.10127 (14)	0.2864 (3)	0.17265 (14)	0.043*	0.9895 (6)
Br2	0.49006 (2)	0.73033 (4)	0.117926 (15)	0.03875 (9)	0.9730 (9)
O21	0.78841 (11)	−0.0300 (2)	0.16645 (11)	0.0550 (4)	0.9730 (9)
O22	0.84166 (9)	0.2333 (2)	0.12216 (10)	0.0406 (3)	0.9730 (9)
N21	0.77141 (12)	0.1329 (2)	0.14878 (12)	0.0359 (4)	0.9730 (9)
N22	0.80935 (11)	0.4104 (2)	0.10262 (12)	0.0369 (4)	0.9730 (9)
C21	0.70073 (12)	0.2493 (2)	0.14604 (13)	0.0275 (4)	0.9730 (9)
C22	0.72559 (11)	0.4177 (2)	0.11757 (12)	0.0262 (4)	0.9730 (9)
C23	0.66221 (12)	0.5714 (2)	0.10828 (12)	0.0284 (4)	0.9730 (9)
H23	0.67618 (12)	0.6869 (2)	0.08902 (12)	0.034*	0.9730 (9)
C24	0.58125 (11)	0.5409 (2)	0.12877 (12)	0.0272 (3)	0.9730 (9)
C25	0.55714 (12)	0.3678 (3)	0.15766 (13)	0.0327 (4)	0.9730 (9)
H25	0.49862 (12)	0.3560 (3)	0.17046 (13)	0.039*	0.9730 (9)
C26	0.61564 (14)	0.2231 (3)	0.16683 (14)	0.0342 (4)	0.9730 (9)
H26	0.60051 (14)	0.1087 (3)	0.18634 (14)	0.041*	0.9730 (9)
Br3	0.0264 (5)	−0.365 (2)	0.1212 (11)	0.03614 (8)	0.0105 (6)
O31	0.3536 (4)	0.004 (3)	0.0513 (6)	0.0424 (3)	0.0105 (6)
O32	0.2969 (4)	0.277 (2)	0.0811 (6)	0.0545 (4)	0.0105 (6)
N31	0.2907 (3)	0.081 (2)	0.0725 (4)	0.0400 (4)	0.0105 (6)
N32	0.2206 (5)	0.339 (2)	0.1051 (7)	0.0362 (4)	0.0105 (6)
C31	0.2122 (3)	0.033 (2)	0.0914 (4)	0.0285 (4)	0.0105 (6)
C32	0.1708 (4)	0.1928 (19)	0.1111 (5)	0.0293 (4)	0.0105 (6)
C33	0.0844 (6)	0.183 (2)	0.1341 (7)	0.0358 (4)	0.0105 (6)
H33	0.0544 (6)	0.287 (2)	0.1477 (7)	0.043*	0.0105 (6)
C34	0.0485 (5)	0.016 (2)	0.1351 (7)	0.0330 (4)	0.0105 (6)
H34	−0.0086 (5)	0.004 (2)	0.1501 (7)	0.040*	0.0105 (6)
C35	0.0913 (5)	−0.146 (2)	0.1150 (7)	0.0266 (3)	0.0105 (6)
C36	0.1727 (4)	−0.1396 (19)	0.0931 (6)	0.0294 (4)	0.0105 (6)
H36	0.2016 (4)	−0.2455 (19)	0.0797 (6)	0.035*	0.0105 (6)
Br4	0.5256 (6)	0.7669 (12)	0.1125 (6)	0.03875 (9)	0.0270 (9)
O41	0.8678 (5)	0.3398 (18)	0.1068 (8)	0.0406 (3)	0.0270 (9)
O42	0.8043 (5)	0.0869 (13)	0.1496 (6)	0.0550 (4)	0.0270 (9)
N41	0.7995 (4)	0.2773 (14)	0.1265 (5)	0.0369 (4)	0.0270 (9)
N42	0.7225 (7)	0.0415 (11)	0.1695 (7)	0.0359 (4)	0.0270 (9)
C41	0.7170 (4)	0.3409 (11)	0.1328 (4)	0.0262 (4)	0.0270 (9)
C42	0.6713 (5)	0.1943 (11)	0.1592 (6)	0.0275 (4)	0.0270 (9)
C43	0.5797 (6)	0.2222 (13)	0.1716 (8)	0.0342 (4)	0.0270 (9)
H43	0.5466 (6)	0.1270 (13)	0.1893 (8)	0.041*	0.0270 (9)
C44	0.5435 (6)	0.3930 (13)	0.1564 (7)	0.0327 (4)	0.0270 (9)
H44	0.4829 (6)	0.4169 (13)	0.1639 (7)	0.039*	0.0270 (9)
C45	0.5913 (5)	0.5409 (11)	0.1295 (5)	0.0272 (3)	0.0270 (9)
C46	0.6768 (5)	0.5171 (11)	0.1177 (5)	0.0284 (4)	0.0270 (9)
H46	0.7088 (5)	0.6140 (11)	0.0999 (5)	0.034*	0.0270 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.03380 (12)	0.03986 (13)	0.03513 (11)	−0.00543 (8)	0.01527 (8)	0.00330 (7)
O11	0.0587 (9)	0.0337 (9)	0.0654 (10)	−0.0133 (7)	0.0214 (8)	−0.0035 (7)
O12	0.0353 (6)	0.0443 (9)	0.0501 (8)	−0.0076 (6)	0.0209 (6)	−0.0003 (6)
N11	0.0364 (8)	0.0324 (9)	0.0361 (8)	−0.0020 (7)	0.0122 (7)	0.0007 (7)
N12	0.0350 (8)	0.0405 (10)	0.0496 (9)	−0.0007 (7)	0.0231 (7)	−0.0014 (8)
C11	0.0289 (8)	0.0293 (10)	0.0256 (8)	0.0007 (7)	0.0079 (6)	0.0018 (7)
C12	0.0258 (7)	0.0320 (9)	0.0268 (8)	0.0060 (7)	0.0107 (6)	0.0022 (7)
C13	0.0313 (8)	0.0277 (9)	0.0307 (8)	0.0031 (7)	0.0148 (7)	−0.0016 (7)
C14	0.0255 (7)	0.0301 (9)	0.0230 (7)	0.0006 (6)	0.0094 (6)	0.0024 (6)
C15	0.0304 (8)	0.0384 (10)	0.0314 (9)	0.0096 (7)	0.0145 (7)	0.0007 (7)
C16	0.0367 (9)	0.0315 (10)	0.0361 (10)	0.0092 (8)	0.0129 (8)	−0.0035 (8)
Br2	0.03698 (14)	0.04170 (14)	0.03580 (11)	0.01015 (9)	0.01410 (9)	−0.00859 (8)
O21	0.0613 (9)	0.0345 (9)	0.0605 (10)	0.0177 (7)	0.0181 (8)	0.0074 (7)
O22	0.0297 (6)	0.0465 (9)	0.0459 (8)	0.0062 (6)	0.0167 (6)	−0.0054 (6)
N21	0.0350 (8)	0.0345 (9)	0.0336 (8)	0.0068 (7)	0.0106 (7)	0.0004 (7)
N22	0.0296 (7)	0.0395 (10)	0.0445 (9)	−0.0027 (7)	0.0188 (7)	−0.0058 (7)
C21	0.0273 (8)	0.0271 (9)	0.0257 (8)	0.0004 (7)	0.0091 (6)	0.0011 (7)
C22	0.0227 (7)	0.0307 (10)	0.0248 (8)	−0.0047 (7)	0.0101 (6)	−0.0049 (7)
C23	0.0323 (8)	0.0247 (9)	0.0290 (8)	−0.0043 (7)	0.0140 (7)	−0.0024 (7)
C24	0.0257 (7)	0.0316 (9)	0.0233 (8)	0.0022 (6)	0.0096 (6)	−0.0037 (6)
C25	0.0271 (8)	0.0441 (11)	0.0294 (8)	−0.0049 (7)	0.0146 (7)	0.0011 (7)
C26	0.0350 (9)	0.0340 (10)	0.0357 (9)	−0.0064 (8)	0.0174 (8)	0.0052 (8)
Br3	0.03380 (12)	0.03986 (13)	0.03513 (11)	−0.00543 (8)	0.01527 (8)	0.00330 (7)
O31	0.0353 (6)	0.0443 (9)	0.0501 (8)	−0.0076 (6)	0.0209 (6)	−0.0003 (6)
O32	0.0587 (9)	0.0337 (9)	0.0654 (10)	−0.0133 (7)	0.0214 (8)	−0.0035 (7)
N31	0.0350 (8)	0.0405 (10)	0.0496 (9)	−0.0007 (7)	0.0231 (7)	−0.0014 (8)
N32	0.0364 (8)	0.0324 (9)	0.0361 (8)	−0.0020 (7)	0.0122 (7)	0.0007 (7)
C31	0.0258 (7)	0.0320 (9)	0.0268 (8)	0.0060 (7)	0.0107 (6)	0.0022 (7)
C32	0.0289 (8)	0.0293 (10)	0.0256 (8)	0.0007 (7)	0.0079 (6)	0.0018 (7)
C33	0.0367 (9)	0.0315 (10)	0.0361 (10)	0.0092 (8)	0.0129 (8)	−0.0035 (8)
C34	0.0304 (8)	0.0384 (10)	0.0314 (9)	0.0096 (7)	0.0145 (7)	0.0007 (7)
C35	0.0255 (7)	0.0301 (9)	0.0230 (7)	0.0006 (6)	0.0094 (6)	0.0024 (6)
C36	0.0313 (8)	0.0277 (9)	0.0307 (8)	0.0031 (7)	0.0148 (7)	−0.0016 (7)
Br4	0.03698 (14)	0.04170 (14)	0.03580 (11)	0.01015 (9)	0.01410 (9)	−0.00859 (8)
O41	0.0297 (6)	0.0465 (9)	0.0459 (8)	0.0062 (6)	0.0167 (6)	−0.0054 (6)
O42	0.0613 (9)	0.0345 (9)	0.0605 (10)	0.0177 (7)	0.0181 (8)	0.0074 (7)
N41	0.0296 (7)	0.0395 (10)	0.0445 (9)	−0.0027 (7)	0.0188 (7)	−0.0058 (7)
N42	0.0350 (8)	0.0345 (9)	0.0336 (8)	0.0068 (7)	0.0106 (7)	0.0004 (7)
C41	0.0227 (7)	0.0307 (10)	0.0248 (8)	−0.0047 (7)	0.0101 (6)	−0.0049 (7)
C42	0.0273 (8)	0.0271 (9)	0.0257 (8)	0.0004 (7)	0.0091 (6)	0.0011 (7)
C43	0.0350 (9)	0.0340 (10)	0.0357 (9)	−0.0064 (8)	0.0174 (8)	0.0052 (8)
C44	0.0271 (8)	0.0441 (11)	0.0294 (8)	−0.0049 (7)	0.0146 (7)	0.0011 (7)
C45	0.0257 (7)	0.0316 (9)	0.0233 (8)	0.0022 (6)	0.0096 (6)	−0.0037 (6)
C46	0.0323 (8)	0.0247 (9)	0.0290 (8)	−0.0043 (7)	0.0140 (7)	−0.0024 (7)

Geometric parameters (Å, º)

Br1—C14	1.897 (2)	Br3—C35	1.897 (3)
O11—N11	1.226 (2)	O31—N31	1.226 (2)
O12—N12	1.378 (2)	O32—N32	1.378 (2)
O12—N11	1.454 (2)	O32—N31	1.454 (2)
N11—C11	1.332 (2)	N31—C31	1.332 (2)
N12—C12	1.325 (2)	N32—C32	1.325 (2)
C11—C16	1.408 (3)	C31—C36	1.408 (3)
C11—C12	1.411 (3)	C31—C32	1.411 (3)
C12—C13	1.435 (2)	C32—C33	1.435 (3)
C13—C14	1.346 (2)	C33—C34	1.346 (2)
C14—C15	1.437 (2)	C34—C35	1.437 (3)
C15—C16	1.352 (3)	C35—C36	1.352 (3)
Br2—C24	1.889 (2)	Br4—C45	1.890 (2)
O21—N21	1.236 (2)	O41—N41	1.236 (2)
O22—N22	1.381 (2)	O42—N42	1.381 (2)
O22—N21	1.446 (2)	O42—N41	1.446 (2)
N21—C21	1.329 (2)	N41—C41	1.329 (2)
N22—C22	1.327 (2)	N42—C42	1.327 (2)
C21—C26	1.408 (2)	C41—C46	1.408 (3)
C21—C22	1.410 (3)	C41—C42	1.410 (3)
C22—C23	1.434 (2)	C42—C43	1.434 (3)
C23—C24	1.352 (2)	C43—C44	1.352 (2)
C24—C25	1.440 (2)	C44—C45	1.440 (3)
C25—C26	1.339 (3)	C45—C46	1.339 (3)
N12—O12—N11	109.10 (12)	N32—O32—N31	109.10 (13)
O11—N11—C11	136.4 (2)	O31—N31—C31	136.4 (2)
O11—N11—O12	117.6 (2)	O31—N31—O32	117.6 (2)
C11—N11—O12	105.95 (14)	C31—N31—O32	105.95 (15)
C12—N12—O12	105.45 (15)	C32—N32—O32	105.4 (2)
N11—C11—C16	129.6 (2)	N31—C31—C36	129.6 (2)
N11—C11—C12	107.2 (2)	N31—C31—C32	107.3 (2)
C16—C11—C12	123.1 (2)	C36—C31—C32	123.1 (2)
N12—C12—C11	112.2 (2)	N32—C32—C31	112.2 (2)
N12—C12—C13	128.1 (2)	N32—C32—C33	128.1 (2)
C11—C12—C13	119.69 (15)	C31—C32—C33	119.7 (2)
C14—C13—C12	115.7 (2)	C34—C33—C32	115.7 (2)
C13—C14—C15	124.1 (2)	C33—C34—C35	124.2 (2)
C13—C14—Br1	120.06 (13)	C36—C35—C34	121.1 (2)
C15—C14—Br1	115.79 (12)	C36—C35—Br3	123.1 (3)
C16—C15—C14	121.1 (2)	C34—C35—Br3	115.8 (2)
C15—C16—C11	116.2 (2)	C35—C36—C31	116.2 (2)
N22—O22—N21	109.16 (12)	N42—O42—N41	109.16 (13)
O21—N21—C21	136.3 (2)	O41—N41—C41	136.3 (2)
O21—N21—O22	117.3 (2)	O41—N41—O42	117.3 (2)
C21—N21—O22	106.48 (14)	C41—N41—O42	106.48 (15)
C22—N22—O22	105.0 (2)	C42—N42—O42	105.0 (2)
N21—C21—C26	130.0 (2)	N41—C41—C46	130.0 (2)
N21—C21—C22	106.9 (2)	N41—C41—C42	106.9 (2)
C26—C21—C22	123.1 (2)	C46—C41—C42	123.1 (2)
N22—C22—C21	112.5 (2)	N42—C42—C41	112.5 (2)
N22—C22—C23	127.9 (2)	N42—C42—C43	127.9 (2)
C21—C22—C23	119.65 (15)	C41—C42—C43	119.7 (2)
C24—C23—C22	115.6 (2)	C44—C43—C42	115.6 (2)
C23—C24—C25	123.9 (2)	C43—C44—C45	123.9 (2)
C23—C24—Br2	120.22 (14)	C46—C45—C44	121.2 (2)
C25—C24—Br2	115.85 (11)	C46—C45—Br4	123.0 (3)
C26—C25—C24	121.3 (2)	C44—C45—Br4	115.8 (2)
C25—C26—C21	116.5 (2)	C45—C46—C41	116.5 (2)