Direct observation of arylnitrene formation in the photoreaction of arylazide crystals

Seven crystal structures of arylazides, 2-azidobiphenyl (2), 4-(4-azidophenyl)butanoic acid (3), 3-azidobenzoic acid (4), N-(4-azidophenyl)acetamide (5), 2,4,6-trichlorophenyl azide (6), 2,5-dibromophenyl azide (7) and 2,4,6-tribromophenyl azide (8), have been analyzed by X-rays. When the crystals were irradiated with UV light at ≃ 80 K, only 2-azidobiphenyl gradually changed its cell dimensions with the retention of the single-crystal form. The crystal structure after photo-irradiation was analyzed by X-rays under the same conditions as those before photo-irradiation. Approximately 20% of the 2-azidobiphenyl molecule was converted to the triplet 2-biphenylnitrene and dinitrogen molecules. The existence of the triplet nitrene was confirmed by ESR and IR measurements. Although the structure of dinitrogen was clearly determined, the nitrene structure was obscure because the nitrene produced was almost superimposed on the original 2-azidobiphenyl. The other six crystals were non-reactive or easily broken when they were exposed to UV light. The different reactivity between 2-azidobiphenyl and the other compounds was successfully explained by the reaction cavity of the azido group.

Computing details

Data collection: Siemens SMART for 2-before, 2-after, (3), (5), (6), (7), (8); RIGAKU R-AXIS RAPID for (4). Cell refinement: Siemens SMART for 2-before, 2-after, (3), (5), (6), (7), (8); RIGAKU R-AXIS RAPID for (4). Data reduction: Siemens SAINT & SADABS for 2-before, 2-after, (3), (5), (6), (7), (8); RIGAKU TEXSAN & ABSCOR for (4). For all structures, program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Window (Farrugia,1998). Software used to prepare material for publication: SHELXTL97 for 2-before, 2-after, (3), (5), (6), (7), (8); SHELXTL97' for (4).

2-azidobiphenyl (2-before)

Crystal data

C12H9N3	F(000) = 408
Mr = 195.22	Dx = 1.324 Mg m^−3
Monoclinic, P21/n	Melting point: not measured K
a = 5.6182 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 26.8034 (6) Å	µ = 0.08 mm^−1
c = 6.9510 (2) Å	T = 83 K
β = 110.693 (2)°	Plate, colorless
V = 979.20 (5) Å^3	0.40 × 0.30 × 0.06 mm
Z = 4

Data collection

Bruker SMART CCD area detector system diffractometer	2851 independent reflections
Radiation source: rotating anode	2498 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω scans	θmax = 30.0°, θmin = 1.5°
Absorption correction: empirical (using intensity measurements) Program SADABS was used.	h = −7→7
Tmin = 0.968, Tmax = 0.995	k = −37→37
15452 measured reflections	l = −9→9

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: difference Fourier map
wR(F^2) = 0.105	Only H-atom coordinates refined
S = 1.11	w = 1/[σ^2(Fo^2) + (0.060P)^2 + 0.1765P] where P = (Fo^2 + 2Fc^2)/3
2851 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.20 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 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 (Ų)

	x	y	z	Uiso*/Ueq
N1	−0.01736 (14)	0.08054 (3)	0.37278 (11)	0.01601 (16)
N2	0.10351 (15)	0.04458 (3)	0.33983 (12)	0.01774 (17)
N3	0.23354 (18)	0.01306 (4)	0.32928 (14)	0.0280 (2)
C1	−0.26601 (15)	0.08879 (3)	0.22189 (12)	0.01314 (17)
C2	−0.36019 (17)	0.06088 (3)	0.04041 (13)	0.01591 (17)
H2	−0.256 (3)	0.0353 (5)	0.009 (2)	0.025 (3)*
C3	−0.60738 (18)	0.06922 (3)	−0.09572 (13)	0.01726 (18)
H3	−0.673 (3)	0.0496 (5)	−0.222 (2)	0.027 (3)*
C4	−0.76077 (17)	0.10526 (3)	−0.05261 (13)	0.01707 (18)
H4	−0.930 (3)	0.1108 (5)	−0.144 (2)	0.029 (3)*
C5	−0.66326 (16)	0.13344 (3)	0.12766 (13)	0.01499 (17)
H5	−0.773 (3)	0.1602 (5)	0.157 (2)	0.023 (3)*
C6	−0.41493 (15)	0.12608 (3)	0.26737 (12)	0.01263 (16)
C7	−0.31489 (15)	0.15764 (3)	0.45579 (12)	0.01207 (16)
C8	−0.43761 (16)	0.15812 (3)	0.60016 (13)	0.01402 (17)
H8	−0.585 (3)	0.1368 (5)	0.579 (2)	0.024 (3)*
C9	−0.34892 (17)	0.18897 (3)	0.77357 (13)	0.01571 (17)
H9	−0.435 (3)	0.1882 (5)	0.875 (2)	0.023 (3)*
C10	−0.14016 (16)	0.22026 (3)	0.80274 (13)	0.01570 (17)
H10	−0.079 (3)	0.2430 (5)	0.920 (2)	0.023 (3)*
C11	−0.01779 (16)	0.22010 (3)	0.65872 (13)	0.01553 (17)
H11	0.133 (3)	0.2413 (5)	0.676 (2)	0.025 (3)*
C12	−0.10290 (16)	0.18877 (3)	0.48788 (13)	0.01417 (17)
H12	−0.012 (2)	0.1890 (5)	0.3843 (19)	0.018 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0139 (3)	0.0179 (3)	0.0145 (3)	0.0022 (3)	0.0028 (3)	−0.0026 (3)
N2	0.0179 (3)	0.0193 (4)	0.0142 (3)	0.0015 (3)	0.0034 (3)	−0.0005 (3)
N3	0.0275 (4)	0.0276 (4)	0.0244 (4)	0.0109 (3)	0.0038 (3)	−0.0034 (3)
C1	0.0132 (3)	0.0146 (4)	0.0114 (4)	−0.0003 (3)	0.0039 (3)	0.0006 (3)
C2	0.0194 (4)	0.0152 (4)	0.0129 (4)	−0.0005 (3)	0.0054 (3)	−0.0011 (3)
C3	0.0212 (4)	0.0174 (4)	0.0109 (4)	−0.0039 (3)	0.0029 (3)	−0.0007 (3)
C4	0.0160 (4)	0.0194 (4)	0.0127 (4)	−0.0019 (3)	0.0012 (3)	0.0020 (3)
C5	0.0139 (4)	0.0169 (4)	0.0133 (4)	0.0001 (3)	0.0038 (3)	0.0017 (3)
C6	0.0135 (3)	0.0139 (4)	0.0104 (3)	−0.0012 (3)	0.0041 (3)	0.0002 (3)
C7	0.0119 (3)	0.0129 (3)	0.0106 (3)	0.0012 (3)	0.0029 (3)	0.0004 (3)
C8	0.0136 (4)	0.0156 (4)	0.0128 (4)	−0.0003 (3)	0.0046 (3)	0.0007 (3)
C9	0.0168 (4)	0.0185 (4)	0.0125 (4)	0.0012 (3)	0.0059 (3)	0.0001 (3)
C10	0.0169 (4)	0.0159 (4)	0.0128 (4)	0.0010 (3)	0.0033 (3)	−0.0019 (3)
C11	0.0139 (4)	0.0150 (4)	0.0165 (4)	−0.0012 (3)	0.0039 (3)	−0.0009 (3)
C12	0.0134 (4)	0.0155 (4)	0.0141 (4)	−0.0001 (3)	0.0055 (3)	0.0002 (3)

Geometric parameters (Å, º)

N1—N2	1.2461 (11)	C5—H5	1.012 (13)
N1—C1	1.4370 (11)	C6—C7	1.4922 (11)
N1—C12	3.0916 (11)	C7—C8	1.4042 (11)
N1—N1^i	4.6436 (16)	C7—C12	1.4059 (11)
N2—N3	1.1360 (12)	C8—C9	1.4001 (12)
C1—C2	1.3997 (11)	C8—H8	0.972 (14)
C1—C6	1.4093 (11)	C9—C10	1.3972 (12)
C2—C3	1.3947 (12)	C9—H9	0.982 (14)
C2—H2	0.976 (14)	C10—C11	1.4005 (12)
C3—C4	1.3958 (13)	C10—H10	0.980 (13)
C3—H3	0.978 (14)	C11—C12	1.3938 (12)
C4—C5	1.3985 (12)	C11—H11	0.990 (14)
C4—H4	0.951 (15)	C12—H12	1.020 (12)
C5—C6	1.4039 (11)
N2—N1—C1	115.93 (7)	C5—C6—C7	120.10 (7)
N2—N1—C12	156.65 (6)	C1—C6—C7	121.98 (7)
C1—N1—C12	81.06 (5)	C8—C7—C12	118.92 (7)
N2—N1—N1^i	53.02 (5)	C8—C7—C6	120.31 (7)
C1—N1—N1^i	108.68 (5)	C12—C7—C6	120.73 (7)
C12—N1—N1^i	139.76 (3)	C9—C8—C7	120.36 (8)
N3—N2—N1	172.64 (9)	C9—C8—H8	120.2 (8)
C2—C1—C6	121.06 (7)	C7—C8—H8	119.5 (8)
C2—C1—N1	122.41 (7)	C10—C9—C8	120.30 (8)
C6—C1—N1	116.52 (7)	C10—C9—H9	120.5 (8)
C3—C2—C1	119.64 (8)	C8—C9—H9	119.2 (8)
C3—C2—H2	119.4 (8)	C9—C10—C11	119.56 (8)
C1—C2—H2	120.9 (8)	C9—C10—H10	121.4 (8)
C2—C3—C4	120.50 (8)	C11—C10—H10	119.0 (8)
C2—C3—H3	119.5 (8)	C12—C11—C10	120.24 (8)
C4—C3—H3	120.0 (8)	C12—C11—H11	118.1 (8)
C3—C4—C5	119.35 (8)	C10—C11—H11	121.7 (8)
C3—C4—H4	120.6 (9)	C11—C12—C7	120.60 (8)
C5—C4—H4	120.0 (9)	C11—C12—N1	138.41 (6)
C4—C5—C6	121.52 (8)	C7—C12—N1	66.58 (5)
C4—C5—H5	119.5 (7)	C11—C12—H12	119.4 (7)
C6—C5—H5	119.0 (7)	C7—C12—H12	120.0 (7)
C5—C6—C1	117.91 (7)	N1—C12—H12	70.2 (7)
C1—N1—N2—N3	−178 (43)	C1—C6—C7—C8	−121.25 (9)
C12—N1—N2—N3	48.4 (9)	C5—C6—C7—C12	−118.00 (9)
N1^i—N1—N2—N3	−83.4 (8)	C1—C6—C7—C12	61.23 (11)
N2—N1—C1—C2	−4.94 (12)	C12—C7—C8—C9	−0.31 (12)
C12—N1—C1—C2	158.17 (8)	C6—C7—C8—C9	−177.88 (8)
N1^i—N1—C1—C2	−62.14 (9)	C7—C8—C9—C10	1.17 (12)
N2—N1—C1—C6	173.79 (8)	C8—C9—C10—C11	−0.86 (13)
C12—N1—C1—C6	−23.10 (7)	C9—C10—C11—C12	−0.29 (13)
N1^i—N1—C1—C6	116.59 (7)	C10—C11—C12—C7	1.15 (13)
C6—C1—C2—C3	−1.48 (13)	C10—C11—C12—N1	−87.17 (11)
N1—C1—C2—C3	177.19 (8)	C8—C7—C12—C11	−0.84 (12)
C1—C2—C3—C4	0.24 (13)	C6—C7—C12—C11	176.71 (7)
C2—C3—C4—C5	0.73 (13)	C8—C7—C12—N1	132.85 (8)
C3—C4—C5—C6	−0.49 (13)	C6—C7—C12—N1	−49.60 (6)
C4—C5—C6—C1	−0.71 (12)	N2—N1—C12—C11	−65.50 (19)
C4—C5—C6—C7	178.55 (8)	C1—N1—C12—C11	155.72 (10)
C2—C1—C6—C5	1.70 (12)	N1^i—N1—C12—C11	47.30 (11)
N1—C1—C6—C5	−177.05 (7)	N2—N1—C12—C7	−175.85 (16)
C2—C1—C6—C7	−177.55 (8)	C1—N1—C12—C7	45.37 (6)
N1—C1—C6—C7	3.70 (11)	N1^i—N1—C12—C7	−63.05 (7)
C5—C6—C7—C8	59.51 (11)

Symmetry code: (i) −x, −y, −z+1.

2-azidobiphenyl (2-after)

Crystal data

C12H9N3	F(000) = 408
Mr = 195.22	Dx = 1.302 Mg m^−3
Monoclinic, P21/n	Melting point: not measured K
a = 5.6598 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 27.1299 (5) Å	µ = 0.08 mm^−1
c = 6.9417 (2) Å	T = 83 K
β = 110.830 (2)°	Plate, pale-brown
V = 996.23 (5) Å^3	0.30 × 0.20 × 0.08 mm
Z = 4

Data collection

Bruker SMART CCD area detector system diffractometer	2890 independent reflections
Radiation source: rotating anode	2048 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
ω scans	θmax = 30.0°, θmin = 1.5°
Absorption correction: empirical (using intensity measurements) Program SADABS was used.	h = −7→7
Tmin = 0.976, Tmax = 0.994	k = −38→38
15755 measured reflections	l = −9→9

Refinement

Refinement on F^2	Primary atom site location: rigid group
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0761P)^2] where P = (Fo^2 + 2Fc^2)/3
2890 reflections	(Δ/σ)max = 0.001
242 parameters	Δρmax = 0.23 e Å^−3
158 restraints	Δρmin = −0.21 e Å^−3

Special details

Experimental. 'photo-irradiated products of dinitrogen and nitrene are observed'

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	−0.03702 (17)	0.08230 (3)	0.36606 (14)	0.0261 (4)	0.801 (5)
N2	0.08305 (19)	0.04654 (3)	0.33351 (15)	0.0287 (4)	0.801 (5)
N3	0.2124 (2)	0.01523 (4)	0.3232 (2)	0.0440 (6)	0.801 (5)
C1	−0.28567 (17)	0.09026 (3)	0.21509 (16)	0.0225 (5)	0.801 (5)
C2	−0.3811 (2)	0.06226 (4)	0.03365 (17)	0.0276 (7)	0.801 (5)
H2	−0.2779	0.0367	0.0017	0.029 (5)*	0.801 (5)
C3	−0.6282 (3)	0.07034 (6)	−0.1026 (2)	0.0294 (7)	0.801 (5)
H3	−0.6953	0.0506	−0.2296	0.041 (6)*	0.801 (5)
C4	−0.7805 (2)	0.10620 (7)	−0.0595 (3)	0.0281 (6)	0.801 (5)
H4	−0.9500	0.1115	−0.1511	0.026 (5)*	0.801 (5)
C5	−0.6819 (2)	0.13448 (5)	0.1207 (3)	0.0259 (7)	0.801 (5)
H5	−0.7907	0.1612	0.1500	0.023 (4)*	0.801 (5)
C6	−0.43347 (18)	0.12737 (4)	0.2604 (2)	0.0218 (6)	0.801 (5)
C7	−0.3324 (2)	0.15901 (5)	0.4485 (2)	0.0203 (7)	0.801 (5)
C8	−0.4528 (3)	0.15978 (7)	0.5944 (3)	0.0244 (8)	0.801 (5)
H8	−0.5989	0.1386	0.5744	0.028 (5)*	0.801 (5)
C9	−0.3630 (4)	0.19067 (8)	0.7677 (3)	0.0271 (8)	0.801 (5)
H9	−0.4467	0.1902	0.8703	0.035 (5)*	0.801 (5)
C10	−0.1554 (4)	0.22169 (8)	0.7952 (3)	0.0244 (7)	0.801 (5)
H10	−0.0942	0.2445	0.9123	0.027 (4)*	0.801 (5)
C11	−0.0353 (4)	0.22124 (6)	0.6496 (3)	0.0235 (7)	0.801 (5)
H11	0.1150	0.2422	0.6662	0.032 (5)*	0.801 (5)
C12	−0.1215 (3)	0.18985 (4)	0.4790 (3)	0.0237 (7)	0.801 (5)
H12	−0.0315	0.1898	0.3743	0.043 (6)*	0.801 (5)
N1P	−0.034 (3)	0.0857 (6)	0.341 (2)	0.112 (6)	0.199 (5)
N2P	0.313 (3)	0.0194 (9)	0.340 (3)	0.259 (16)	0.199 (5)
N3P	0.198 (5)	−0.0051 (11)	0.397 (4)	0.185 (10)	0.199 (5)
C1P	−0.282 (3)	0.0916 (7)	0.203 (2)	0.092 (6)	0.199 (5)
C2P	−0.363 (4)	0.0635 (6)	0.035 (2)	0.086 (6)	0.199 (5)
H2P	−0.2553	0.0395	0.0093	0.103*	0.199 (5)
C3P	−0.578 (5)	0.0692 (6)	−0.084 (3)	0.071 (5)	0.199 (5)
H3P	−0.6306	0.0498	−0.2060	0.086*	0.199 (5)
C4P	−0.745 (3)	0.1001 (7)	−0.059 (3)	0.062 (4)	0.199 (5)
H4P	−0.9129	0.1016	−0.1548	0.074*	0.199 (5)
C5P	−0.666 (3)	0.1301 (5)	0.112 (3)	0.055 (4)	0.199 (5)
H5P	−0.7761	0.1540	0.1351	0.067*	0.199 (5)
C6P	−0.426 (3)	0.1246 (5)	0.247 (2)	0.059 (5)	0.199 (5)
C7P	−0.345 (2)	0.1540 (5)	0.427 (2)	0.046 (4)	0.199 (5)
C8P	−0.462 (3)	0.1571 (5)	0.572 (2)	0.044 (4)	0.199 (5)
H8P	−0.6117	0.1383	0.5460	0.052*	0.199 (5)
C9P	−0.384 (2)	0.1841 (5)	0.743 (2)	0.032 (3)	0.199 (5)
H9P	−0.4744	0.1837	0.8353	0.038*	0.199 (5)
C10P	−0.175 (3)	0.2119 (6)	0.7847 (18)	0.031 (3)	0.199 (5)
H10P	−0.1154	0.2313	0.9064	0.037*	0.199 (5)
C11P	−0.050 (2)	0.2116 (5)	0.646 (2)	0.035 (3)	0.199 (5)
H11P	0.0967	0.2313	0.6703	0.042*	0.199 (5)
C12P	−0.138 (2)	0.1832 (4)	0.4789 (16)	0.040 (3)	0.199 (5)
H12P	−0.0469	0.1835	0.3875	0.048*	0.199 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0270 (9)	0.0290 (8)	0.0216 (9)	0.0000 (7)	0.0077 (7)	−0.0048 (6)
N2	0.0315 (8)	0.0312 (8)	0.0229 (7)	0.0037 (6)	0.0089 (6)	−0.0009 (5)
N3	0.0478 (12)	0.0434 (11)	0.0398 (11)	0.0105 (9)	0.0142 (8)	−0.0015 (8)
C1	0.0266 (12)	0.0231 (9)	0.0164 (10)	−0.0025 (8)	0.0060 (9)	0.0008 (6)
C2	0.0362 (13)	0.0263 (11)	0.0200 (14)	−0.0051 (10)	0.0097 (11)	−0.0027 (10)
C3	0.0365 (12)	0.0316 (14)	0.0152 (11)	−0.0084 (11)	0.0032 (8)	0.0016 (9)
C4	0.0288 (13)	0.0343 (12)	0.0168 (11)	−0.0049 (10)	0.0028 (9)	0.0032 (9)
C5	0.0236 (11)	0.0354 (17)	0.0166 (11)	−0.0045 (10)	0.0047 (9)	0.0008 (10)
C6	0.0223 (10)	0.0262 (13)	0.0165 (13)	−0.0027 (9)	0.0065 (9)	0.0002 (10)
C7	0.0223 (14)	0.0242 (12)	0.0119 (9)	−0.0006 (10)	0.0030 (8)	−0.0018 (9)
C8	0.0211 (12)	0.0359 (18)	0.0176 (13)	−0.0030 (11)	0.0085 (10)	0.0022 (11)
C9	0.0294 (16)	0.0360 (14)	0.0160 (11)	−0.0012 (11)	0.0083 (9)	−0.0041 (10)
C10	0.0248 (11)	0.0252 (14)	0.0215 (12)	−0.0012 (9)	0.0061 (9)	−0.0047 (8)
C11	0.0240 (12)	0.0245 (13)	0.0207 (10)	−0.0040 (8)	0.0066 (8)	−0.0028 (8)
C12	0.0187 (11)	0.0303 (13)	0.0223 (15)	−0.0028 (10)	0.0074 (9)	0.0007 (10)
N1P	0.095 (9)	0.209 (17)	0.043 (6)	0.019 (10)	0.039 (6)	0.014 (8)
N2P	0.33 (4)	0.28 (3)	0.19 (2)	−0.12 (3)	0.11 (2)	0.02 (2)
N3P	0.190 (19)	0.23 (2)	0.163 (19)	−0.105 (18)	0.092 (16)	−0.061 (18)
C1P	0.068 (9)	0.169 (15)	0.052 (9)	0.023 (9)	0.039 (7)	−0.004 (8)
C2P	0.091 (10)	0.120 (15)	0.055 (12)	0.046 (10)	0.037 (8)	0.016 (9)
C3P	0.115 (10)	0.066 (10)	0.039 (8)	0.017 (8)	0.035 (7)	−0.006 (6)
C4P	0.042 (6)	0.092 (10)	0.037 (7)	0.010 (7)	−0.004 (5)	0.016 (6)
C5P	0.084 (8)	0.040 (7)	0.060 (8)	0.035 (6)	0.047 (6)	0.020 (5)
C6P	0.086 (9)	0.072 (11)	0.022 (7)	−0.016 (7)	0.022 (6)	0.007 (6)
C7P	0.042 (8)	0.052 (7)	0.048 (7)	0.016 (6)	0.023 (5)	0.020 (5)
C8P	0.055 (8)	0.036 (8)	0.026 (6)	−0.001 (6)	−0.002 (5)	−0.007 (5)
C9P	0.025 (5)	0.049 (6)	0.026 (5)	0.002 (5)	0.016 (4)	0.012 (4)
C10P	0.051 (7)	0.024 (4)	0.010 (4)	−0.003 (4)	0.002 (3)	−0.009 (3)
C11P	0.023 (5)	0.025 (4)	0.058 (7)	−0.007 (3)	0.016 (4)	0.014 (3)
C12P	0.071 (9)	0.037 (5)	0.017 (6)	0.021 (5)	0.023 (6)	0.006 (4)

Geometric parameters (Å, º)

N1—N2	1.2502	C2P—C3P	1.21 (2)
N1—C1	1.4410	C2P—H2	0.9439
N2—N3	1.1403	C2P—H2P	0.9500
C1—C2	1.4041	C3P—C4P	1.32 (2)
C1—C6	1.4140	C3P—H3	1.1126
C2—C3	1.3994	C3P—H3P	0.9500
C2—H2	0.9808	C4P—C5P	1.375 (19)
C3—C4	1.4007	C4P—H4	1.1523
C3—H3	0.9851	C4P—H4P	0.9500
C4—C5	1.4031	C5P—C6P	1.355 (17)
C4—H4	0.9545	C5P—H5	1.1877
C5—C6	1.4089	C5P—H5P	0.9500
C5—H5	1.0175	C6P—C7P	1.416 (17)
C6—C7	1.4960	C7P—C12P	1.354 (12)
C7—C8	1.4074	C7P—C8P	1.385 (11)
C7—C12	1.4108	C8P—C9P	1.334 (12)
C8—C9	1.4047	C8P—H8	0.9286
C8—H8	0.9757	C8P—H8P	0.9500
C9—C10	1.4019	C9P—C10P	1.341 (11)
C9—H9	0.9859	C9P—H9	1.0737
C10—C11	1.4041	C9P—H9P	0.9500
C10—H10	0.9807	C10P—C11P	1.383 (10)
C11—C12	1.3984	C10P—H10	1.2197
C11—H11	0.9952	C10P—H10P	0.9500
C12—H12	1.0248	C11P—C12P	1.336 (11)
N1P—C1P	1.396 (19)	C11P—H11	1.2194
N2P—N3P	1.0977 (11)	C11P—H11P	0.9500
C1P—C6P	1.317 (19)	C12P—H12	1.1113
C1P—C2P	1.33 (2)	C12P—H12P	0.9500
N2—N1—C1	116.0	C6P—C5P—H5	117.0
N3—N2—N1	172.7	C4P—C5P—H5	125.1
C2—C1—C6	121.0	C6P—C5P—H5P	121.1
C2—C1—N1	122.4	C4P—C5P—H5P	121.1
C6—C1—N1	116.5	H5—C5P—H5P	4.1
C3—C2—C1	119.6	C1P—C6P—C5P	117.8 (13)
C2—C3—C4	120.5	C1P—C6P—C7P	123.6 (12)
C3—C4—C5	119.3	C5P—C6P—C7P	118.5 (13)
C4—C5—C6	121.5	C12P—C7P—C8P	111.4 (11)
C5—C6—C1	118.0	C12P—C7P—C6P	122.6 (9)
C5—C6—C7	120.0	C8P—C7P—C6P	126.0 (11)
C1—C6—C7	122.0	C9P—C8P—C7P	126.0 (11)
C8—C7—C12	118.9	C9P—C8P—H8	107.0
C8—C7—C6	120.3	C7P—C8P—H8	126.7
C12—C7—C6	120.8	C9P—C8P—H8P	117.0
C9—C8—C7	120.3	C7P—C8P—H8P	117.0
C10—C9—C8	120.3	H8—C8P—H8P	11.2
C9—C10—C11	119.6	C8P—C9P—C10P	119.1 (9)
C12—C11—C10	120.2	C8P—C9P—H9	135.7
C11—C12—C7	120.7	C10P—C9P—H9	105.2
C6P—C1P—C2P	122.9 (14)	C8P—C9P—H9P	120.4
C6P—C1P—N1P	118.3 (13)	C10P—C9P—H9P	120.4
C2P—C1P—N1P	118.8 (14)	H9—C9P—H9P	15.3
C3P—C2P—C1P	118.3 (14)	C9P—C10P—C11P	118.6 (9)
C3P—C2P—H2	113.9	C9P—C10P—H10	129.6
C1P—C2P—H2	127.5	C11P—C10P—H10	110.7
C3P—C2P—H2P	120.9	C9P—C10P—H10P	120.7
C1P—C2P—H2P	120.9	C11P—C10P—H10P	120.7
H2—C2P—H2P	8.6	H10—C10P—H10P	13.9
C2P—C3P—C4P	125.4 (13)	C12P—C11P—C10P	118.8 (9)
C2P—C3P—H3	133.8	C12P—C11P—H11	121.7
C4P—C3P—H3	100.7	C10P—C11P—H11	118.7
C2P—C3P—H3P	117.3	C12P—C11P—H11P	120.6
C4P—C3P—H3P	117.3	C10P—C11P—H11P	120.6
H3—C3P—H3P	17.0	H11—C11P—H11P	9.0
C3P—C4P—C5P	117.6 (14)	C11P—C12P—C7P	126.1 (9)
C3P—C4P—H4	136.2	C11P—C12P—H12	110.7
C5P—C4P—H4	106.0	C7P—C12P—H12	122.9
C3P—C4P—H4P	121.2	C11P—C12P—H12P	117.0
C5P—C4P—H4P	121.2	C7P—C12P—H12P	117.0
H4—C4P—H4P	15.5	H12—C12P—H12P	8.9
C6P—C5P—C4P	117.9 (14)
C1—N1—N2—N3	−178 (50)	C6—C7—C12—C11	176.7
N2—N1—C1—C2	−4.9	C6P—C1P—C2P—C3P	1 (3)
N2—N1—C1—C6	173.8	N1P—C1P—C2P—C3P	−179.4 (15)
C6—C1—C2—C3	−1.5	C1P—C2P—C3P—C4P	−2 (3)
N1—C1—C2—C3	177.2	C2P—C3P—C4P—C5P	3 (2)
C1—C2—C3—C4	0.2	C3P—C4P—C5P—C6P	−2.5 (17)
C2—C3—C4—C5	0.8	C2P—C1P—C6P—C5P	−1 (2)
C3—C4—C5—C6	−0.5	N1P—C1P—C6P—C5P	179.8 (13)
C4—C5—C6—C1	−0.7	C2P—C1P—C6P—C7P	178.3 (13)
C4—C5—C6—C7	178.5	N1P—C1P—C6P—C7P	−1 (2)
C2—C1—C6—C5	1.7	C4P—C5P—C6P—C1P	1.4 (17)
N1—C1—C6—C5	−177.0	C4P—C5P—C6P—C7P	−177.6 (10)
C2—C1—C6—C7	−177.5	C1P—C6P—C7P—C12P	56.3 (16)
N1—C1—C6—C7	3.7	C5P—C6P—C7P—C12P	−124.7 (11)
C5—C6—C7—C8	59.6	C1P—C6P—C7P—C8P	−123.9 (14)
C1—C6—C7—C8	−121.2	C5P—C6P—C7P—C8P	55.1 (15)
C5—C6—C7—C12	−118.1	C12P—C7P—C8P—C9P	−1.3 (14)
C1—C6—C7—C12	61.2	C6P—C7P—C8P—C9P	178.9 (10)
C12—C7—C8—C9	−0.3	C7P—C8P—C9P—C10P	1.0 (15)
C6—C7—C8—C9	−177.9	C8P—C9P—C10P—C11P	0.3 (14)
C7—C8—C9—C10	1.1	C9P—C10P—C11P—C12P	−1.1 (14)
C8—C9—C10—C11	−0.8	C10P—C11P—C12P—C7P	0.6 (16)
C9—C10—C11—C12	−0.3	C8P—C7P—C12P—C11P	0.5 (14)
C10—C11—C12—C7	1.2	C6P—C7P—C12P—C11P	−179.7 (10)
C8—C7—C12—C11	−0.9

4-(4-azidophenyl)butylic acid (3)

Crystal data

C10H11N3O2	F(000) = 432
Mr = 205.22	Dx = 1.374 Mg m^−3
Monoclinic, P21/c	Melting point: not measured K
a = 4.7195 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 16.9565 (6) Å	µ = 0.10 mm^−1
c = 12.6172 (4) Å	T = 80 K
β = 100.623 (1)°	Plate, colorless
V = 992.40 (6) Å^3	0.26 × 0.12 × 0.06 mm
Z = 4

Data collection

Bruker SMART CCD area detector system diffractometer	2888 independent reflections
Radiation source: rotating anode	2061 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.072
ω scans	θmax = 30.0°, θmin = 2.0°
Absorption correction: empirical (using intensity measurements) Program SADABS was used.	h = −6→6
Tmin = 0.975, Tmax = 0.994	k = −23→23
15707 measured reflections	l = −17→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Only H-atom coordinates refined
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0589P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max = 0.001
2888 reflections	Δρmax = 0.37 e Å^−3
181 parameters	Δρmin = −0.22 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: 0.030 (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 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 (Ų)

	x	y	z	Uiso*/Ueq
C1	−0.0708 (3)	0.69876 (7)	1.16116 (9)	0.0144 (2)
C2	−0.0219 (3)	0.75487 (7)	1.08526 (9)	0.0159 (2)
H2	−0.110 (3)	0.8079 (9)	1.0851 (11)	0.019 (4)*
C3	0.1460 (3)	0.73490 (7)	1.00918 (9)	0.0158 (2)
H3	0.185 (3)	0.7756 (9)	0.9544 (11)	0.020 (4)*
C4	0.2637 (2)	0.65928 (7)	1.00575 (9)	0.0144 (2)
C5	0.2123 (3)	0.60428 (7)	1.08298 (9)	0.0163 (2)
H5	0.293 (3)	0.5507 (9)	1.0800 (12)	0.025 (4)*
C6	0.0481 (3)	0.62339 (7)	1.16087 (9)	0.0159 (2)
H6	0.018 (3)	0.5844 (8)	1.2130 (11)	0.014 (3)*
C7	0.4303 (3)	0.63717 (8)	0.91859 (9)	0.0166 (2)
H71	0.525 (3)	0.6854 (9)	0.8942 (11)	0.022 (4)*
H72	0.586 (4)	0.6024 (9)	0.9488 (12)	0.027 (4)*
C8	0.2354 (3)	0.59933 (7)	0.82096 (9)	0.0152 (2)
H81	0.162 (3)	0.5480 (8)	0.8409 (10)	0.018 (3)*
H82	0.071 (3)	0.6334 (8)	0.7963 (11)	0.021 (4)*
C9	0.3955 (3)	0.58551 (7)	0.72782 (9)	0.0154 (2)
H91	0.560 (3)	0.5482 (9)	0.7482 (12)	0.027 (4)*
H92	0.478 (3)	0.6362 (9)	0.7067 (12)	0.025 (4)*
C10	0.2120 (2)	0.54955 (6)	0.62934 (9)	0.0136 (2)
O1	0.31719 (19)	0.56138 (5)	0.54039 (7)	0.0183 (2)
H1	0.215 (4)	0.5351 (11)	0.4831 (16)	0.051 (5)*
O2	−0.01018 (18)	0.51231 (5)	0.63166 (6)	0.0178 (2)
N1	−0.2443 (2)	0.72445 (6)	1.23666 (8)	0.0178 (2)
N2	−0.3057 (2)	0.67357 (6)	1.30042 (8)	0.0180 (2)
N3	−0.3770 (3)	0.63414 (7)	1.36330 (9)	0.0254 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0148 (5)	0.0167 (5)	0.0119 (5)	−0.0026 (4)	0.0025 (4)	−0.0030 (4)
C2	0.0188 (6)	0.0145 (5)	0.0143 (5)	−0.0014 (4)	0.0022 (4)	−0.0020 (4)
C3	0.0168 (6)	0.0188 (6)	0.0117 (5)	−0.0044 (5)	0.0021 (4)	0.0003 (4)
C4	0.0133 (5)	0.0188 (6)	0.0107 (5)	−0.0034 (4)	0.0007 (4)	−0.0021 (4)
C5	0.0178 (6)	0.0161 (6)	0.0151 (5)	0.0005 (4)	0.0034 (4)	−0.0019 (4)
C6	0.0186 (6)	0.0162 (6)	0.0129 (5)	−0.0021 (5)	0.0031 (4)	0.0005 (4)
C7	0.0150 (6)	0.0220 (6)	0.0131 (5)	−0.0026 (5)	0.0035 (4)	−0.0030 (5)
C8	0.0155 (6)	0.0182 (6)	0.0121 (5)	−0.0026 (5)	0.0033 (4)	−0.0027 (4)
C9	0.0152 (6)	0.0191 (6)	0.0122 (5)	−0.0015 (5)	0.0038 (4)	−0.0024 (4)
C10	0.0166 (6)	0.0126 (5)	0.0124 (5)	0.0031 (4)	0.0045 (4)	0.0003 (4)
O1	0.0217 (5)	0.0229 (5)	0.0116 (4)	−0.0057 (4)	0.0064 (3)	−0.0034 (3)
O2	0.0174 (4)	0.0227 (4)	0.0138 (4)	−0.0040 (3)	0.0040 (3)	−0.0021 (3)
N1	0.0236 (5)	0.0173 (5)	0.0148 (5)	0.0008 (4)	0.0093 (4)	−0.0001 (4)
N2	0.0189 (5)	0.0206 (5)	0.0154 (5)	0.0010 (4)	0.0055 (4)	−0.0044 (4)
N3	0.0321 (6)	0.0261 (6)	0.0208 (6)	−0.0004 (5)	0.0127 (5)	0.0014 (5)

Geometric parameters (Å, º)

C1—C6	1.3961 (17)	C7—H71	1.006 (15)
C1—C2	1.3989 (16)	C7—H72	0.965 (16)
C1—N1	1.4336 (15)	C8—C9	1.5278 (16)
C2—C3	1.3945 (16)	C8—H81	0.988 (14)
C2—H2	0.991 (15)	C8—H82	0.970 (15)
C3—C4	1.4013 (17)	C9—C10	1.5063 (16)
C3—H3	1.018 (14)	C9—H91	0.997 (16)
C4—C5	1.4020 (17)	C9—H92	1.001 (15)
C4—C7	1.5123 (16)	C10—O2	1.2289 (14)
C5—C6	1.3969 (17)	C10—O1	1.3235 (13)
C5—H5	0.989 (16)	O1—H1	0.91 (2)
C6—H6	0.962 (14)	N1—N2	1.2495 (14)
C7—C8	1.5356 (16)	N2—N3	1.1349 (15)
C6—C1—C2	120.24 (11)	C4—C7—H72	109.0 (9)
C6—C1—N1	123.98 (10)	C8—C7—H72	111.2 (9)
C2—C1—N1	115.78 (10)	H71—C7—H72	105.6 (13)
C3—C2—C1	119.51 (11)	C9—C8—C7	111.90 (10)
C3—C2—H2	120.7 (8)	C9—C8—H81	108.0 (8)
C1—C2—H2	119.8 (8)	C7—C8—H81	110.6 (8)
C2—C3—C4	121.48 (11)	C9—C8—H82	108.9 (9)
C2—C3—H3	120.0 (8)	C7—C8—H82	109.5 (8)
C4—C3—H3	118.5 (8)	H81—C8—H82	108.0 (12)
C3—C4—C5	117.83 (11)	C10—C9—C8	113.95 (10)
C3—C4—C7	120.76 (11)	C10—C9—H91	104.9 (8)
C5—C4—C7	121.37 (11)	C8—C9—H91	111.7 (9)
C6—C5—C4	121.62 (11)	C10—C9—H92	108.8 (8)
C6—C5—H5	120.6 (9)	C8—C9—H92	110.2 (9)
C4—C5—H5	117.8 (9)	H91—C9—H92	107.0 (12)
C1—C6—C5	119.31 (11)	O2—C10—O1	123.59 (10)
C1—C6—H6	121.1 (8)	O2—C10—C9	123.48 (10)
C5—C6—H6	119.6 (8)	O1—C10—C9	112.92 (10)
C4—C7—C8	111.83 (10)	C10—O1—H1	111.8 (12)
C4—C7—H71	109.9 (8)	N2—N1—C1	116.54 (10)
C8—C7—H71	109.1 (8)	N3—N2—N1	172.14 (12)
C6—C1—C2—C3	0.13 (17)	C3—C4—C7—C8	−92.48 (13)
N1—C1—C2—C3	179.66 (10)	C5—C4—C7—C8	85.01 (14)
C1—C2—C3—C4	1.04 (17)	C4—C7—C8—C9	173.54 (10)
C2—C3—C4—C5	−1.25 (17)	C7—C8—C9—C10	−179.13 (10)
C2—C3—C4—C7	176.32 (11)	C8—C9—C10—O2	−21.65 (17)
C3—C4—C5—C6	0.32 (17)	C8—C9—C10—O1	159.21 (10)
C7—C4—C5—C6	−177.24 (11)	C6—C1—N1—N2	−5.05 (17)
C2—C1—C6—C5	−1.04 (17)	C2—C1—N1—N2	175.45 (11)
N1—C1—C6—C5	179.48 (11)	C1—N1—N2—N3	177.6 (9)
C4—C5—C6—C1	0.81 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.91 (2)	1.78 (2)	2.6858 (12)	177.5 (19)

Symmetry code: (i) −x, −y+1, −z+1.

3-carboxyphenylazide (4)

Crystal data

C7H5N3O2	Z = 2
Mr = 163.14	F(000) = 168
Triclinic, P1	Dx = 1.483 Mg m^−3
a = 3.7639 (5) Å	Melting point: not measured K
b = 6.5389 (12) Å	Mo Kα radiation, λ = 0.71073 Å
c = 15.141 (3) Å	µ = 0.11 mm^−1
α = 80.829 (6)°	T = 80 K
β = 83.770 (5)°	Plate, pale-yellow
γ = 86.189 (5)°	0.40 × 0.19 × 0.04 mm
V = 365.24 (11) Å^3

Data collection

RIGAKU R-AXIS RAPID IP detector system diffractometer	1310 independent reflections
Radiation source: rotating anode	1120 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
ω scans	θmax = 25.4°, θmin = 3.6°
Absorption correction: empirical (using intensity measurements) Program ABSCOR was used.	h = −4→4
Tmin = 0.956, Tmax = 0.996	k = −7→7
2550 measured reflections	l = −18→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Only H-atom coordinates refined
wR(F^2) = 0.161	w = 1/[σ^2(Fo^2) + (0.0909P)^2 + 0.1356P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
1310 reflections	Δρmax = 0.18 e Å^−3
126 parameters	Δρmin = −0.28 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: 0.19 (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 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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.5424 (4)	0.5292 (2)	0.38650 (10)	0.0504 (5)
O2	0.3004 (5)	0.2758 (3)	0.48582 (10)	0.0578 (5)
H1	0.378 (11)	0.357 (7)	0.539 (3)	0.123 (14)*
C7	0.3922 (5)	0.3615 (3)	0.40452 (13)	0.0380 (5)
C1	0.3110 (5)	0.2511 (3)	0.33164 (13)	0.0371 (5)
C2	0.3763 (6)	0.3445 (3)	0.24312 (14)	0.0399 (5)
H2	0.465 (6)	0.476 (4)	0.2287 (16)	0.048*
C3	0.3026 (5)	0.2407 (3)	0.17498 (13)	0.0414 (5)
C4	0.1677 (6)	0.0447 (3)	0.19459 (15)	0.0436 (5)
H4	0.109 (7)	−0.032 (4)	0.1460 (17)	0.052*
C5	0.1030 (6)	−0.0464 (3)	0.28323 (15)	0.0455 (6)
H5	0.022 (7)	−0.179 (4)	0.2951 (17)	0.055*
C6	0.1735 (6)	0.0554 (3)	0.35208 (15)	0.0434 (5)
H6	0.140 (7)	−0.009 (4)	0.4125 (18)	0.052*
N1	0.3838 (6)	0.3461 (3)	0.08526 (14)	0.0606 (6)
N2	0.2887 (6)	0.2650 (3)	0.02416 (12)	0.0539 (6)
N3	0.2184 (8)	0.2092 (4)	−0.03768 (15)	0.0756 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0688 (11)	0.0435 (9)	0.0425 (9)	−0.0173 (7)	−0.0077 (7)	−0.0097 (6)
O2	0.0823 (12)	0.0556 (10)	0.0390 (9)	−0.0244 (8)	−0.0073 (8)	−0.0081 (7)
C7	0.0406 (10)	0.0398 (10)	0.0345 (10)	−0.0045 (8)	−0.0048 (8)	−0.0068 (8)
C1	0.0353 (10)	0.0396 (10)	0.0385 (11)	−0.0024 (8)	−0.0061 (8)	−0.0103 (8)
C2	0.0425 (11)	0.0386 (10)	0.0408 (11)	−0.0077 (8)	−0.0059 (8)	−0.0092 (8)
C3	0.0447 (11)	0.0457 (11)	0.0360 (11)	−0.0081 (9)	−0.0061 (8)	−0.0091 (8)
C4	0.0455 (11)	0.0442 (11)	0.0459 (12)	−0.0066 (8)	−0.0092 (8)	−0.0159 (9)
C5	0.0501 (12)	0.0355 (11)	0.0536 (13)	−0.0097 (9)	−0.0095 (9)	−0.0091 (9)
C6	0.0456 (12)	0.0391 (11)	0.0464 (12)	−0.0056 (9)	−0.0086 (9)	−0.0051 (9)
N1	0.0886 (16)	0.0577 (12)	0.0406 (10)	−0.0305 (11)	−0.0105 (9)	−0.0093 (9)
N2	0.0718 (13)	0.0533 (11)	0.0401 (10)	−0.0184 (9)	−0.0093 (9)	−0.0092 (9)
N3	0.107 (2)	0.0782 (16)	0.0495 (13)	−0.0316 (14)	−0.0183 (12)	−0.0159 (11)

Geometric parameters (Å, º)

O1—C7	1.245 (2)	C3—N1	1.433 (3)
O2—C7	1.289 (2)	C4—C5	1.381 (3)
O2—H1	1.10 (5)	C4—H4	1.00 (3)
C7—C1	1.479 (3)	C5—C6	1.380 (3)
C1—C2	1.385 (3)	C5—H5	0.92 (3)
C1—C6	1.389 (3)	C6—H6	0.94 (3)
C2—C3	1.383 (3)	N1—N2	1.232 (3)
C2—H2	0.93 (3)	N2—N3	1.120 (3)
C3—C4	1.386 (3)
C7—O2—H1	115 (2)	C4—C3—N1	123.51 (19)
O1—C7—O2	122.68 (18)	C5—C4—C3	119.46 (19)
O1—C7—C1	120.42 (17)	C5—C4—H4	118.8 (14)
O2—C7—C1	116.90 (17)	C3—C4—H4	121.8 (14)
C2—C1—C6	120.59 (19)	C6—C5—C4	120.6 (2)
C2—C1—C7	119.24 (18)	C6—C5—H5	120.8 (16)
C6—C1—C7	120.17 (18)	C4—C5—H5	118.5 (16)
C3—C2—C1	119.23 (19)	C5—C6—C1	119.4 (2)
C3—C2—H2	119.4 (15)	C5—C6—H6	120.9 (16)
C1—C2—H2	121.3 (15)	C1—C6—H6	119.6 (16)
C2—C3—C4	120.67 (19)	N2—N1—C3	116.57 (19)
C2—C3—N1	115.80 (19)	N3—N2—N1	172.3 (2)
O1—C7—C1—C2	−5.4 (3)	N1—C3—C4—C5	178.9 (2)
O2—C7—C1—C2	174.62 (18)	C3—C4—C5—C6	−0.4 (3)
O1—C7—C1—C6	174.11 (19)	C4—C5—C6—C1	−0.1 (3)
O2—C7—C1—C6	−5.9 (3)	C2—C1—C6—C5	0.2 (3)
C6—C1—C2—C3	0.1 (3)	C7—C1—C6—C5	−179.29 (18)
C7—C1—C2—C3	179.58 (17)	C2—C3—N1—N2	−173.3 (2)
C1—C2—C3—C4	−0.5 (3)	C4—C3—N1—N2	8.3 (4)
C1—C2—C3—N1	−178.88 (19)	C3—N1—N2—N3	−180 (2)
C2—C3—C4—C5	0.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1···O1^i	1.10 (5)	1.52 (5)	2.617 (2)	176 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

4-(acetylamino)phenylazide (5)

Crystal data

C8H8N4O	F(000) = 1472
Mr = 176.18	Dx = 1.338 Mg m^−3
Orthorhombic, Pbca	Melting point: not measured K
a = 7.1342 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 19.2898 (5) Å	µ = 0.10 mm^−1
c = 25.4147 (6) Å	T = 80 K
V = 3497.50 (16) Å^3	Block, pale-brown
Z = 16	0.30 × 0.30 × 0.20 mm

Data collection

Bruker SMART CCD area detector system diffractometer	5073 independent reflections
Radiation source: rotating anode	4051 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
ω scans	θmax = 30.0°, θmin = 1.6°
Absorption correction: empirical (using intensity measurements) Program SADABS was used.	h = −10→10
Tmin = 0.972, Tmax = 0.981	k = −27→27
52542 measured reflections	l = −35→35

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)] = 0.040	Hydrogen site location: difference Fourier map
wR(F^2) = 0.112	Only H-atom coordinates refined
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0607P)^2 + 0.7499P] where P = (Fo^2 + 2Fc^2)/3
5073 reflections	(Δ/σ)max = 0.001
299 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.23 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 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 (Ų)

	x	y	z	Uiso*/Ueq
C1A	0.94890 (15)	0.52561 (6)	0.18625 (4)	0.0230 (2)
C2A	1.00458 (15)	0.58502 (6)	0.15915 (5)	0.0245 (2)
C3A	0.95718 (15)	0.59282 (5)	0.10640 (4)	0.0227 (2)
C4A	0.85429 (14)	0.54136 (5)	0.08000 (4)	0.0203 (2)
C5A	0.80172 (16)	0.48132 (6)	0.10726 (5)	0.0239 (2)
C6A	0.84906 (16)	0.47367 (6)	0.16027 (5)	0.0248 (2)
C7A	0.73984 (15)	0.51002 (5)	−0.01000 (4)	0.0208 (2)
C8A	0.70987 (18)	0.54123 (6)	−0.06388 (5)	0.0255 (2)
N1A	1.00136 (15)	0.52164 (5)	0.24082 (4)	0.0287 (2)
N2A	0.92970 (14)	0.47388 (5)	0.26683 (4)	0.0289 (2)
N3A	0.87409 (18)	0.43290 (6)	0.29494 (5)	0.0413 (3)
N4A	0.80835 (13)	0.55476 (5)	0.02668 (4)	0.02153 (19)
O1A	0.70353 (12)	0.44858 (4)	−0.00032 (3)	0.02631 (18)
H2A	1.078 (2)	0.6195 (8)	0.1772 (6)	0.032 (4)*
H3A	0.9962 (19)	0.6336 (7)	0.0866 (6)	0.029 (4)*
H4A	0.827 (2)	0.5989 (8)	0.0164 (6)	0.037 (4)*
H5A	0.732 (2)	0.4464 (8)	0.0893 (6)	0.039 (4)*
H6A	0.815 (2)	0.4316 (8)	0.1797 (6)	0.034 (4)*
H81A	0.605 (3)	0.5628 (12)	−0.0657 (9)	0.082 (7)*
H82A	0.709 (3)	0.5095 (12)	−0.0906 (9)	0.080 (7)*
H83A	0.804 (3)	0.5729 (11)	−0.0729 (8)	0.071 (6)*
C1B	0.56862 (15)	0.28498 (6)	−0.19764 (4)	0.0223 (2)
C2B	0.50284 (15)	0.34332 (6)	−0.17090 (4)	0.0238 (2)
C3B	0.53650 (15)	0.34964 (5)	−0.11711 (4)	0.0220 (2)
C4B	0.63423 (14)	0.29797 (5)	−0.08982 (4)	0.01911 (19)
C5B	0.69832 (15)	0.23947 (5)	−0.11696 (4)	0.0219 (2)
C6B	0.66486 (15)	0.23291 (6)	−0.17079 (4)	0.0231 (2)
C7B	0.67871 (15)	0.25876 (5)	0.00234 (4)	0.0212 (2)
C8B	0.70458 (17)	0.28585 (6)	0.05767 (4)	0.0250 (2)
N1B	0.52946 (15)	0.28251 (5)	−0.25294 (4)	0.0300 (2)
N2B	0.60526 (14)	0.23515 (5)	−0.27839 (4)	0.0277 (2)
N3B	0.66542 (17)	0.19492 (6)	−0.30653 (4)	0.0374 (3)
N4B	0.66721 (13)	0.30869 (5)	−0.03533 (4)	0.02118 (18)
O1B	0.66694 (13)	0.19621 (4)	−0.00778 (3)	0.0312 (2)
H2B	0.435 (2)	0.3787 (8)	−0.1901 (6)	0.035 (4)*
H3B	0.491 (2)	0.3900 (8)	−0.0984 (5)	0.030 (4)*
H4B	0.669 (2)	0.3531 (8)	−0.0254 (6)	0.033 (4)*
H5B	0.767 (2)	0.2047 (7)	−0.0991 (5)	0.029 (4)*
H6B	0.707 (2)	0.1921 (8)	−0.1901 (6)	0.033 (4)*
H81B	0.819 (3)	0.3118 (9)	0.0616 (7)	0.053 (5)*
H82B	0.608 (3)	0.3175 (10)	0.0679 (8)	0.064 (6)*
H83B	0.713 (3)	0.2486 (10)	0.0826 (8)	0.063 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0197 (5)	0.0240 (5)	0.0253 (5)	0.0011 (4)	0.0007 (4)	−0.0025 (4)
C2A	0.0213 (5)	0.0220 (5)	0.0300 (5)	−0.0026 (4)	0.0010 (4)	−0.0053 (4)
C3A	0.0216 (5)	0.0169 (5)	0.0296 (5)	−0.0025 (4)	0.0030 (4)	−0.0015 (4)
C4A	0.0177 (4)	0.0173 (4)	0.0258 (5)	0.0008 (4)	0.0010 (4)	−0.0009 (4)
C5A	0.0238 (5)	0.0182 (5)	0.0298 (5)	−0.0040 (4)	−0.0026 (4)	−0.0003 (4)
C6A	0.0247 (5)	0.0201 (5)	0.0296 (5)	−0.0028 (4)	−0.0004 (4)	0.0025 (4)
C7A	0.0187 (4)	0.0174 (4)	0.0262 (5)	0.0021 (4)	0.0029 (4)	−0.0020 (4)
C8A	0.0278 (6)	0.0226 (5)	0.0262 (5)	0.0027 (4)	0.0015 (4)	−0.0001 (4)
N1A	0.0297 (5)	0.0297 (5)	0.0266 (5)	−0.0034 (4)	−0.0012 (4)	−0.0009 (4)
N2A	0.0259 (5)	0.0312 (5)	0.0294 (5)	0.0042 (4)	−0.0035 (4)	0.0000 (4)
N3A	0.0428 (7)	0.0410 (6)	0.0401 (6)	−0.0009 (5)	−0.0050 (5)	0.0120 (5)
N4A	0.0238 (4)	0.0148 (4)	0.0260 (4)	−0.0009 (3)	−0.0004 (3)	0.0011 (3)
O1A	0.0331 (4)	0.0164 (4)	0.0294 (4)	−0.0024 (3)	0.0016 (3)	−0.0020 (3)
C1B	0.0211 (5)	0.0236 (5)	0.0223 (5)	−0.0020 (4)	−0.0015 (4)	0.0018 (4)
C2B	0.0220 (5)	0.0218 (5)	0.0276 (5)	0.0029 (4)	−0.0012 (4)	0.0045 (4)
C3B	0.0219 (5)	0.0173 (4)	0.0268 (5)	0.0018 (4)	0.0018 (4)	0.0016 (4)
C4B	0.0182 (4)	0.0167 (4)	0.0225 (5)	−0.0015 (4)	0.0013 (4)	0.0021 (4)
C5B	0.0231 (5)	0.0176 (5)	0.0249 (5)	0.0031 (4)	0.0005 (4)	0.0021 (4)
C6B	0.0242 (5)	0.0195 (5)	0.0255 (5)	0.0011 (4)	0.0015 (4)	−0.0009 (4)
C7B	0.0217 (5)	0.0178 (5)	0.0241 (5)	0.0015 (4)	0.0010 (4)	0.0026 (4)
C8B	0.0291 (6)	0.0234 (5)	0.0226 (5)	0.0042 (4)	−0.0001 (4)	0.0005 (4)
N1B	0.0340 (6)	0.0306 (5)	0.0253 (5)	0.0036 (4)	−0.0047 (4)	−0.0002 (4)
N2B	0.0284 (5)	0.0292 (5)	0.0256 (5)	−0.0052 (4)	−0.0033 (4)	0.0009 (4)
N3B	0.0426 (6)	0.0372 (6)	0.0325 (5)	−0.0045 (5)	0.0002 (5)	−0.0070 (4)
N4B	0.0267 (4)	0.0150 (4)	0.0218 (4)	0.0005 (3)	0.0006 (3)	0.0004 (3)
O1B	0.0485 (5)	0.0166 (4)	0.0286 (4)	0.0012 (3)	−0.0005 (4)	0.0027 (3)

Geometric parameters (Å, º)

C1A—C2A	1.3948 (16)	C1B—C6B	1.3950 (15)
C1A—C6A	1.3955 (15)	C1B—C2B	1.3960 (15)
C1A—N1A	1.4384 (15)	C1B—N1B	1.4338 (14)
C2A—C3A	1.3907 (16)	C2B—C3B	1.3932 (16)
C2A—H2A	0.961 (15)	C2B—H2B	0.967 (15)
C3A—C4A	1.4051 (14)	C3B—C4B	1.4003 (14)
C3A—H3A	0.975 (14)	C3B—H3B	0.969 (15)
C4A—C5A	1.4008 (14)	C4B—C5B	1.3995 (14)
C4A—N4A	1.4178 (14)	C4B—N4B	1.4197 (13)
C5A—C6A	1.3969 (16)	C5B—C6B	1.3943 (15)
C5A—H5A	0.954 (16)	C5B—H5B	0.947 (14)
C6A—H6A	0.979 (15)	C6B—H6B	0.975 (15)
C7A—O1A	1.2377 (12)	C7B—O1B	1.2366 (13)
C7A—N4A	1.3613 (14)	C7B—N4B	1.3607 (13)
C7A—C8A	1.5110 (15)	C7B—C8B	1.5115 (15)
C8A—H81A	0.86 (2)	C8B—H81B	0.960 (19)
C8A—H82A	0.92 (2)	C8B—H82B	0.95 (2)
C8A—H83A	0.93 (2)	C8B—H83B	0.96 (2)
N1A—N2A	1.2439 (14)	N1B—N2B	1.2433 (15)
N2A—N3A	1.1368 (15)	N2B—N3B	1.1391 (15)
N4A—H4A	0.900 (16)	N4B—H4B	0.892 (15)
C2A—C1A—C6A	120.10 (10)	C6B—C1B—C2B	120.52 (10)
C2A—C1A—N1A	116.48 (10)	C6B—C1B—N1B	123.47 (10)
C6A—C1A—N1A	123.41 (10)	C2B—C1B—N1B	116.01 (9)
C3A—C2A—C1A	119.72 (10)	C3B—C2B—C1B	119.36 (10)
C3A—C2A—H2A	121.2 (9)	C3B—C2B—H2B	121.2 (9)
C1A—C2A—H2A	119.1 (9)	C1B—C2B—H2B	119.4 (9)
C2A—C3A—C4A	120.73 (10)	C2B—C3B—C4B	120.64 (10)
C2A—C3A—H3A	121.1 (9)	C2B—C3B—H3B	119.7 (8)
C4A—C3A—H3A	118.2 (9)	C4B—C3B—H3B	119.7 (8)
C5A—C4A—C3A	119.19 (10)	C5B—C4B—C3B	119.50 (10)
C5A—C4A—N4A	124.16 (9)	C5B—C4B—N4B	122.96 (9)
C3A—C4A—N4A	116.64 (9)	C3B—C4B—N4B	117.52 (9)
C6A—C5A—C4A	119.98 (10)	C6B—C5B—C4B	120.06 (10)
C6A—C5A—H5A	120.9 (9)	C6B—C5B—H5B	119.6 (8)
C4A—C5A—H5A	119.1 (9)	C4B—C5B—H5B	120.3 (8)
C1A—C6A—C5A	120.26 (10)	C5B—C6B—C1B	119.92 (10)
C1A—C6A—H6A	118.8 (9)	C5B—C6B—H6B	120.9 (9)
C5A—C6A—H6A	120.9 (9)	C1B—C6B—H6B	119.1 (9)
O1A—C7A—N4A	123.10 (10)	O1B—C7B—N4B	122.70 (10)
O1A—C7A—C8A	122.15 (10)	O1B—C7B—C8B	122.64 (10)
N4A—C7A—C8A	114.76 (9)	N4B—C7B—C8B	114.66 (9)
C7A—C8A—H81A	111.5 (15)	C7B—C8B—H81B	112.3 (11)
C7A—C8A—H82A	114.0 (14)	C7B—C8B—H82B	112.7 (12)
H81A—C8A—H82A	106 (2)	H81B—C8B—H82B	104.3 (15)
C7A—C8A—H83A	112.3 (13)	C7B—C8B—H83B	111.3 (11)
H81A—C8A—H83A	107.2 (19)	H81B—C8B—H83B	105.5 (16)
H82A—C8A—H83A	105.0 (18)	H82B—C8B—H83B	110.3 (16)
N2A—N1A—C1A	116.42 (10)	N2B—N1B—C1B	116.72 (10)
N3A—N2A—N1A	172.92 (13)	N3B—N2B—N1B	172.35 (12)
C7A—N4A—C4A	128.46 (9)	C7B—N4B—C4B	126.39 (9)
C7A—N4A—H4A	117.0 (10)	C7B—N4B—H4B	118.6 (10)
C4A—N4A—H4A	114.5 (10)	C4B—N4B—H4B	114.7 (10)
C6A—C1A—C2A—C3A	1.18 (16)	C6B—C1B—C2B—C3B	0.91 (16)
N1A—C1A—C2A—C3A	−179.33 (10)	N1B—C1B—C2B—C3B	−179.60 (10)
C1A—C2A—C3A—C4A	−0.23 (16)	C1B—C2B—C3B—C4B	−0.40 (16)
C2A—C3A—C4A—C5A	−0.87 (16)	C2B—C3B—C4B—C5B	−0.07 (16)
C2A—C3A—C4A—N4A	178.37 (10)	C2B—C3B—C4B—N4B	178.53 (10)
C3A—C4A—C5A—C6A	1.03 (16)	C3B—C4B—C5B—C6B	0.03 (15)
N4A—C4A—C5A—C6A	−178.16 (10)	N4B—C4B—C5B—C6B	−178.49 (10)
C2A—C1A—C6A—C5A	−1.02 (17)	C4B—C5B—C6B—C1B	0.47 (16)
N1A—C1A—C6A—C5A	179.52 (10)	C2B—C1B—C6B—C5B	−0.95 (16)
C4A—C5A—C6A—C1A	−0.09 (17)	N1B—C1B—C6B—C5B	179.60 (10)
C2A—C1A—N1A—N2A	170.09 (10)	C6B—C1B—N1B—N2B	−8.57 (17)
C6A—C1A—N1A—N2A	−10.43 (17)	C2B—C1B—N1B—N2B	171.95 (10)
C1A—N1A—N2A—N3A	−179 (79)	C1B—N1B—N2B—N3B	−177.9 (9)
O1A—C7A—N4A—C4A	1.59 (17)	O1B—C7B—N4B—C4B	2.44 (17)
C8A—C7A—N4A—C4A	−178.79 (10)	C8B—C7B—N4B—C4B	−176.83 (10)
C5A—C4A—N4A—C7A	−13.17 (17)	C5B—C4B—N4B—C7B	−33.00 (16)
C3A—C4A—N4A—C7A	167.63 (10)	C3B—C4B—N4B—C7B	148.45 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4A—H4A···O1B^i	0.900 (16)	1.976 (16)	2.8710 (12)	172.5 (14)
N4B—H4B···O1A	0.892 (15)	1.965 (16)	2.8532 (12)	173.2 (14)

Symmetry code: (i) −x+3/2, y+1/2, z.

2,4,6-trichlorophenylazide (6)

Crystal data

C6H2Cl3N3	F(000) = 220
Mr = 222.46	Dx = 1.829 Mg m^−3
Monoclinic, P21	Melting point: not measured K
a = 3.7715 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.1451 (2) Å	µ = 1.07 mm^−1
c = 8.3333 (2) Å	T = 80 K
β = 102.138 (1)°	Block, colorless
V = 403.90 (2) Å^3	0.40 × 0.15 × 0.10 mm
Z = 2

Data collection

Bruker SMART CCD area detector system diffractometer	2367 independent reflections
Radiation source: rotating anode	2291 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω scans	θmax = 30.0°, θmin = 2.5°
Absorption correction: empirical (using intensity measurements) Program SADABS was used.	h = −5→5
Tmin = 0.674, Tmax = 0.900	k = −18→18
6446 measured reflections	l = −11→11

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.023	Only H-atom coordinates refined
wR(F^2) = 0.055	w = 1/[σ^2(Fo^2) + (0.0309P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
2367 reflections	Δρmax = 0.34 e Å^−3
117 parameters	Δρmin = −0.47 e Å^−3
1 restraint	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (5)

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 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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.8620 (4)	0.76728 (11)	0.62615 (18)	0.0162 (3)
N2	0.9989 (4)	0.74718 (11)	0.77298 (18)	0.0136 (3)
N3	1.1239 (4)	0.74425 (12)	0.90882 (18)	0.0198 (3)
C1	0.7759 (4)	0.68641 (13)	0.51035 (19)	0.0110 (3)
C2	0.6440 (4)	0.58996 (12)	0.54075 (19)	0.0114 (3)
C3	0.5389 (4)	0.51821 (12)	0.41608 (19)	0.0114 (3)
C4	0.5643 (4)	0.54463 (12)	0.25743 (19)	0.0117 (3)
C5	0.6971 (4)	0.63907 (13)	0.22139 (19)	0.0116 (3)
C6	0.8006 (4)	0.70887 (12)	0.34782 (19)	0.0112 (3)
H3	0.441 (6)	0.452 (2)	0.446 (3)	0.026 (6)*
H5	0.721 (7)	0.654 (2)	0.111 (3)	0.038 (7)*
Cl1	0.58806 (10)	0.55740 (3)	0.73641 (4)	0.01324 (8)
Cl2	0.41579 (10)	0.45879 (3)	0.09786 (5)	0.01564 (8)
Cl3	0.95928 (10)	0.82686 (3)	0.30258 (5)	0.01413 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0260 (7)	0.0104 (6)	0.0108 (6)	0.0004 (5)	0.0007 (5)	0.0000 (5)
N2	0.0157 (6)	0.0109 (6)	0.0142 (6)	0.0010 (5)	0.0031 (5)	−0.0003 (5)
N3	0.0254 (7)	0.0160 (7)	0.0155 (7)	0.0010 (6)	−0.0012 (6)	−0.0021 (5)
C1	0.0130 (6)	0.0101 (6)	0.0095 (7)	0.0019 (5)	0.0013 (5)	0.0001 (5)
C2	0.0128 (6)	0.0122 (7)	0.0091 (6)	0.0015 (5)	0.0025 (5)	0.0015 (5)
C3	0.0115 (6)	0.0106 (7)	0.0117 (7)	0.0000 (5)	0.0018 (5)	0.0011 (5)
C4	0.0110 (6)	0.0127 (7)	0.0106 (6)	0.0007 (5)	0.0004 (5)	−0.0015 (5)
C5	0.0114 (6)	0.0123 (7)	0.0107 (7)	0.0014 (5)	0.0016 (5)	0.0025 (5)
C6	0.0110 (6)	0.0106 (7)	0.0122 (7)	0.0013 (5)	0.0029 (5)	0.0032 (5)
Cl1	0.01737 (17)	0.01327 (17)	0.00977 (16)	−0.00081 (13)	0.00446 (12)	0.00107 (14)
Cl2	0.01976 (18)	0.01512 (17)	0.01151 (16)	−0.00403 (14)	0.00210 (13)	−0.00262 (13)
Cl3	0.01747 (17)	0.00998 (16)	0.01485 (17)	−0.00117 (14)	0.00319 (13)	0.00268 (13)

Geometric parameters (Å, º)

N1—N2	1.252 (2)	C3—C4	1.390 (2)
N1—C1	1.427 (2)	C3—H3	1.00 (3)
N2—N3	1.132 (2)	C4—C5	1.395 (2)
C1—C2	1.404 (2)	C4—Cl2	1.7441 (16)
C1—C6	1.408 (2)	C5—C6	1.390 (2)
C2—C3	1.397 (2)	C5—H5	0.97 (3)
C2—Cl1	1.7409 (16)	C6—Cl3	1.7323 (16)
N2—N1—C1	119.49 (14)	C2—C3—H3	117.9 (14)
N3—N2—N1	169.76 (17)	C3—C4—C5	121.81 (15)
C2—C1—C6	117.41 (14)	C3—C4—Cl2	119.23 (12)
C2—C1—N1	126.13 (15)	C5—C4—Cl2	118.94 (12)
C6—C1—N1	116.28 (15)	C6—C5—C4	118.73 (14)
C3—C2—C1	122.08 (14)	C6—C5—H5	121.5 (18)
C3—C2—Cl1	117.33 (12)	C4—C5—H5	119.8 (18)
C1—C2—Cl1	120.54 (12)	C5—C6—C1	121.73 (15)
C4—C3—C2	118.24 (14)	C5—C6—Cl3	118.74 (12)
C4—C3—H3	123.9 (14)	C1—C6—Cl3	119.52 (12)
C1—N1—N2—N3	178.0 (9)	C2—C3—C4—Cl2	−177.12 (11)
N2—N1—C1—C2	36.1 (2)	C3—C4—C5—C6	−1.1 (2)
N2—N1—C1—C6	−149.00 (15)	Cl2—C4—C5—C6	177.28 (11)
C6—C1—C2—C3	−0.2 (2)	C4—C5—C6—C1	0.3 (2)
N1—C1—C2—C3	174.63 (15)	C4—C5—C6—Cl3	−179.06 (12)
C6—C1—C2—Cl1	−177.55 (11)	C2—C1—C6—C5	0.4 (2)
N1—C1—C2—Cl1	−2.7 (2)	N1—C1—C6—C5	−174.98 (14)
C1—C2—C3—C4	−0.6 (2)	C2—C1—C6—Cl3	179.68 (11)
Cl1—C2—C3—C4	176.84 (12)	N1—C1—C6—Cl3	4.33 (19)
C2—C3—C4—C5	1.2 (2)

2,5-dibromophenyl azide (7)

Crystal data

C6H3Br2N3	F(000) = 2080
Mr = 276.93	Dx = 2.274 Mg m^−3
Monoclinic, P21/c	Melting point: not measured K
a = 15.4939 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 29.0284 (2) Å	µ = 9.96 mm^−1
c = 7.3042 (1) Å	T = 80 K
β = 100.0241 (3)°	Block, colorless
V = 3235.01 (5) Å^3	0.30 × 0.30 × 0.20 mm
Z = 16

Data collection

Bruker SMART CCD area detector system diffractometer	9434 independent reflections
Radiation source: fine-focus sealed tube	7032 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.069
ω scans	θmax = 30.0°, θmin = 1.3°
Absorption correction: empirical (using intensity measurements) Program SADABS was used.	h = −21→21
Tmin = 0.154, Tmax = 0.241	k = −40→40
51587 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)] = 0.041	Hydrogen site location: difference Fourier map
wR(F^2) = 0.084	Only H-atom coordinates refined
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0372P)^2 + 2.7336P] where P = (Fo^2 + 2Fc^2)/3
9434 reflections	(Δ/σ)max = 0.002
433 parameters	Δρmax = 0.81 e Å^−3
0 restraints	Δρmin = −0.90 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 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 (Ų)

	x	y	z	Uiso*/Ueq
Br1A	0.29641 (3)	0.320347 (14)	0.87002 (6)	0.02316 (10)
Br2A	0.67010 (3)	0.209555 (16)	0.98827 (7)	0.02888 (11)
C1A	0.4046 (2)	0.24001 (13)	0.9005 (6)	0.0151 (8)
C2A	0.4041 (2)	0.28807 (14)	0.9058 (5)	0.0151 (8)
C3A	0.4816 (3)	0.31238 (14)	0.9380 (6)	0.0200 (8)
H3A	0.479 (3)	0.3460 (17)	0.943 (6)	0.024*
C4A	0.5617 (3)	0.28963 (15)	0.9622 (6)	0.0219 (9)
H4A	0.609 (3)	0.3074 (17)	0.975 (6)	0.026*
C5A	0.5614 (3)	0.24200 (14)	0.9537 (6)	0.0184 (8)
C6A	0.4848 (3)	0.21660 (14)	0.9237 (6)	0.0184 (8)
H6A	0.485 (3)	0.1805 (16)	0.914 (6)	0.022*
N1A	0.3221 (2)	0.21699 (12)	0.8695 (5)	0.0218 (8)
N2A	0.3252 (2)	0.17388 (12)	0.8777 (5)	0.0202 (7)
N3A	0.3189 (2)	0.13534 (13)	0.8825 (6)	0.0263 (8)
Br1B	0.21892 (2)	0.558654 (13)	0.33432 (5)	0.01536 (8)
Br2B	−0.16129 (2)	0.453715 (13)	0.18730 (5)	0.01511 (8)
C1B	0.1025 (2)	0.48298 (13)	0.3568 (5)	0.0131 (7)
C2B	0.1092 (2)	0.52837 (13)	0.2937 (5)	0.0135 (7)
C3B	0.0359 (3)	0.55106 (14)	0.2016 (6)	0.0154 (8)
H3B	0.040 (3)	0.5814 (16)	0.148 (6)	0.019*
C4B	−0.0454 (2)	0.52928 (14)	0.1703 (5)	0.0142 (7)
H4B	−0.092 (3)	0.5457 (15)	0.102 (6)	0.017*
C5B	−0.0513 (2)	0.48427 (13)	0.2311 (5)	0.0124 (7)
C6B	0.0213 (2)	0.46086 (13)	0.3244 (5)	0.0133 (7)
H6B	0.015 (3)	0.4302 (15)	0.375 (6)	0.016*
N1B	0.1801 (2)	0.46128 (12)	0.4530 (5)	0.0190 (7)
N2B	0.1677 (2)	0.42465 (12)	0.5333 (5)	0.0177 (7)
N3B	0.1655 (2)	0.39114 (13)	0.6131 (5)	0.0251 (8)
Br1C	0.37666 (2)	0.590747 (13)	0.83763 (5)	0.01591 (8)
Br2C	0.56153 (2)	0.398850 (13)	0.63414 (5)	0.01585 (8)
C1C	0.5223 (2)	0.53248 (13)	0.8059 (5)	0.0125 (7)
C2C	0.4316 (2)	0.53583 (13)	0.7762 (5)	0.0120 (7)
C3C	0.3791 (3)	0.49888 (14)	0.7033 (6)	0.0155 (8)
H3C	0.323 (3)	0.5010 (16)	0.677 (6)	0.019*
C4C	0.4168 (3)	0.45779 (14)	0.6600 (6)	0.0160 (8)
H4C	0.382 (3)	0.4333 (16)	0.620 (6)	0.019*
C5C	0.5082 (2)	0.45467 (13)	0.6934 (5)	0.0124 (7)
C6C	0.5612 (3)	0.49106 (13)	0.7635 (6)	0.0150 (8)
H6C	0.621 (3)	0.4886 (15)	0.777 (6)	0.018*
N1C	0.5718 (2)	0.57147 (11)	0.8789 (5)	0.0174 (7)
N2C	0.6531 (2)	0.56510 (11)	0.9216 (5)	0.0191 (7)
N3C	0.7271 (2)	0.56423 (13)	0.9663 (6)	0.0273 (9)
Br1D	0.11330 (3)	0.141674 (15)	0.60453 (6)	0.02303 (10)
Br2D	−0.09646 (3)	0.338465 (15)	0.49927 (7)	0.02962 (11)
N1D	−0.0826 (2)	0.15563 (12)	0.5063 (5)	0.0216 (8)
N2D	−0.1640 (2)	0.15751 (12)	0.4864 (6)	0.0244 (8)
N3D	−0.2381 (2)	0.15403 (14)	0.4666 (7)	0.0341 (10)
C1D	−0.0388 (2)	0.19885 (13)	0.5292 (5)	0.0149 (8)
C2D	0.0524 (3)	0.19860 (13)	0.5760 (5)	0.0154 (8)
C3D	0.0993 (3)	0.23945 (15)	0.6007 (6)	0.0214 (9)
H3D	0.160 (3)	0.2397 (16)	0.634 (7)	0.026*
C4D	0.0561 (3)	0.28127 (15)	0.5796 (6)	0.0213 (9)
H4D	0.084 (3)	0.3111 (17)	0.597 (6)	0.026*
C5D	−0.0346 (3)	0.28157 (13)	0.5306 (6)	0.0186 (8)
C6D	−0.0832 (3)	0.24094 (14)	0.5047 (6)	0.0188 (8)
H6D	−0.147 (3)	0.2394 (16)	0.470 (6)	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1A	0.01672 (19)	0.01535 (19)	0.0358 (2)	0.00395 (15)	−0.00003 (17)	−0.00204 (17)
Br2A	0.01339 (19)	0.0202 (2)	0.0522 (3)	0.00161 (16)	0.00315 (19)	0.0014 (2)
C1A	0.0114 (17)	0.0141 (18)	0.019 (2)	−0.0019 (14)	0.0003 (15)	0.0014 (15)
C2A	0.0129 (18)	0.0179 (19)	0.0137 (18)	−0.0001 (15)	−0.0002 (14)	−0.0005 (15)
C3A	0.021 (2)	0.0110 (19)	0.028 (2)	−0.0015 (15)	0.0047 (17)	−0.0018 (16)
C4A	0.015 (2)	0.018 (2)	0.032 (3)	−0.0043 (16)	0.0029 (17)	−0.0007 (18)
C5A	0.0141 (18)	0.017 (2)	0.025 (2)	0.0019 (15)	0.0037 (16)	−0.0006 (16)
C6A	0.0173 (19)	0.015 (2)	0.021 (2)	0.0020 (15)	−0.0019 (16)	0.0013 (16)
N1A	0.0139 (16)	0.0133 (17)	0.036 (2)	−0.0011 (13)	−0.0020 (15)	0.0000 (15)
N2A	0.0104 (15)	0.0196 (18)	0.0280 (19)	−0.0017 (13)	−0.0041 (14)	0.0000 (15)
N3A	0.0157 (17)	0.0170 (19)	0.043 (2)	−0.0033 (14)	−0.0032 (16)	−0.0002 (16)
Br1B	0.00938 (17)	0.01596 (18)	0.02005 (19)	−0.00290 (14)	0.00066 (14)	0.00016 (15)
Br2B	0.00863 (16)	0.01665 (19)	0.01966 (19)	−0.00212 (13)	0.00135 (14)	−0.00139 (15)
C1B	0.0104 (17)	0.0143 (18)	0.0143 (18)	0.0025 (14)	0.0011 (14)	−0.0012 (14)
C2B	0.0112 (17)	0.0171 (19)	0.0132 (18)	−0.0041 (14)	0.0052 (14)	−0.0048 (14)
C3B	0.0131 (18)	0.0138 (19)	0.020 (2)	0.0002 (14)	0.0038 (15)	−0.0008 (15)
C4B	0.0094 (17)	0.0173 (19)	0.0148 (19)	0.0022 (14)	−0.0007 (14)	0.0006 (15)
C5B	0.0096 (16)	0.0141 (18)	0.0136 (18)	−0.0013 (13)	0.0028 (14)	−0.0050 (14)
C6B	0.0123 (17)	0.0127 (18)	0.0144 (18)	0.0016 (14)	0.0012 (14)	0.0020 (14)
N1B	0.0103 (15)	0.0152 (17)	0.0302 (19)	0.0012 (12)	−0.0002 (14)	0.0032 (14)
N2B	0.0118 (15)	0.0171 (17)	0.0229 (18)	0.0040 (13)	−0.0006 (13)	−0.0024 (14)
N3B	0.0176 (18)	0.0202 (19)	0.035 (2)	0.0035 (15)	−0.0026 (15)	0.0092 (16)
Br1C	0.01096 (17)	0.01458 (18)	0.0215 (2)	0.00222 (14)	0.00097 (14)	−0.00298 (15)
Br2C	0.01551 (18)	0.01109 (17)	0.02103 (19)	0.00027 (13)	0.00341 (15)	−0.00129 (14)
C1C	0.0098 (17)	0.0103 (17)	0.0172 (19)	−0.0024 (13)	0.0017 (14)	0.0000 (14)
C2C	0.0144 (17)	0.0102 (17)	0.0117 (17)	0.0004 (13)	0.0027 (14)	−0.0012 (14)
C3C	0.0112 (18)	0.0162 (19)	0.019 (2)	0.0009 (14)	0.0020 (15)	−0.0013 (15)
C4C	0.0171 (19)	0.0129 (18)	0.0174 (19)	−0.0038 (15)	0.0013 (15)	−0.0022 (15)
C5C	0.0129 (17)	0.0113 (17)	0.0141 (18)	0.0008 (14)	0.0051 (14)	−0.0001 (14)
C6C	0.0091 (17)	0.0127 (18)	0.022 (2)	0.0030 (14)	−0.0002 (14)	0.0043 (15)
N1C	0.0088 (15)	0.0135 (16)	0.0288 (19)	−0.0004 (12)	0.0007 (13)	−0.0018 (14)
N2C	0.0143 (16)	0.0101 (16)	0.031 (2)	−0.0010 (12)	0.0000 (14)	0.0005 (14)
N3C	0.0130 (17)	0.0170 (18)	0.049 (3)	−0.0030 (14)	−0.0024 (16)	−0.0016 (17)
Br1D	0.01428 (19)	0.0170 (2)	0.0368 (3)	−0.00063 (15)	0.00157 (17)	0.00305 (17)
Br2D	0.0339 (3)	0.0137 (2)	0.0404 (3)	0.00174 (18)	0.0041 (2)	−0.00144 (18)
N1D	0.0088 (15)	0.0163 (17)	0.039 (2)	−0.0008 (13)	0.0021 (15)	−0.0020 (15)
N2D	0.0210 (19)	0.0138 (17)	0.039 (2)	−0.0007 (14)	0.0067 (16)	−0.0054 (16)
N3D	0.0153 (19)	0.021 (2)	0.066 (3)	−0.0006 (15)	0.0062 (19)	−0.003 (2)
C1D	0.0139 (18)	0.0115 (18)	0.019 (2)	−0.0030 (14)	0.0013 (15)	−0.0011 (15)
C2D	0.0196 (19)	0.0139 (19)	0.0130 (18)	−0.0009 (15)	0.0039 (15)	−0.0003 (14)
C3D	0.017 (2)	0.020 (2)	0.026 (2)	−0.0055 (16)	0.0008 (17)	0.0017 (17)
C4D	0.026 (2)	0.015 (2)	0.022 (2)	−0.0077 (17)	0.0025 (17)	−0.0022 (16)
C5D	0.025 (2)	0.0105 (18)	0.021 (2)	−0.0004 (15)	0.0054 (17)	0.0002 (15)
C6D	0.018 (2)	0.018 (2)	0.020 (2)	−0.0009 (16)	0.0028 (16)	−0.0035 (16)

Geometric parameters (Å, º)

Br1A—C2A	1.891 (4)	Br1C—C2C	1.897 (4)
Br2A—C5A	1.907 (4)	Br2C—C5C	1.903 (4)
C1A—C2A	1.396 (5)	C1C—C2C	1.387 (5)
C1A—C6A	1.400 (5)	C1C—C6C	1.403 (5)
C1A—N1A	1.425 (5)	C1C—N1C	1.418 (5)
C2A—C3A	1.378 (6)	C2C—C3C	1.395 (5)
C3A—C4A	1.389 (6)	C3C—C4C	1.389 (5)
C3A—H3A	0.98 (5)	C3C—H3C	0.86 (5)
C4A—C5A	1.384 (6)	C4C—C5C	1.397 (5)
C4A—H4A	0.89 (5)	C4C—H4C	0.91 (5)
C5A—C6A	1.383 (6)	C5C—C6C	1.381 (5)
C6A—H6A	1.05 (5)	C6C—H6C	0.92 (5)
N1A—N2A	1.253 (5)	N1C—N2C	1.258 (5)
N2A—N3A	1.124 (5)	N2C—N3C	1.137 (5)
Br1B—C2B	1.891 (4)	Br1D—C2D	1.896 (4)
Br2B—C5B	1.898 (4)	Br2D—C5D	1.903 (4)
C1B—C6B	1.395 (5)	N1D—N2D	1.245 (5)
C1B—C2B	1.406 (5)	N1D—C1D	1.422 (5)
C1B—N1B	1.430 (5)	N2D—N3D	1.137 (5)
C2B—C3B	1.382 (5)	C1D—C2D	1.395 (5)
C3B—C4B	1.393 (5)	C1D—C6D	1.398 (6)
C3B—H3B	0.97 (5)	C2D—C3D	1.386 (6)
C4B—C5B	1.388 (5)	C3D—C4D	1.382 (6)
C4B—H4B	0.93 (5)	C3D—H3D	0.93 (5)
C5B—C6B	1.388 (5)	C4D—C5D	1.388 (6)
C6B—H6B	0.97 (4)	C4D—H4D	0.97 (5)
N1B—N2B	1.246 (5)	C5D—C6D	1.395 (6)
N2B—N3B	1.138 (5)	C6D—H6D	0.98 (5)
C2A—C1A—C6A	119.4 (4)	C2C—C1C—C6C	119.2 (3)
C2A—C1A—N1A	117.6 (3)	C2C—C1C—N1C	118.0 (3)
C6A—C1A—N1A	123.0 (4)	C6C—C1C—N1C	122.8 (3)
C3A—C2A—C1A	120.5 (4)	C1C—C2C—C3C	120.9 (3)
C3A—C2A—Br1A	119.5 (3)	C1C—C2C—Br1C	120.4 (3)
C1A—C2A—Br1A	120.0 (3)	C3C—C2C—Br1C	118.7 (3)
C2A—C3A—C4A	120.7 (4)	C4C—C3C—C2C	120.5 (4)
C2A—C3A—H3A	119 (3)	C4C—C3C—H3C	117 (3)
C4A—C3A—H3A	120 (3)	C2C—C3C—H3C	122 (3)
C5A—C4A—C3A	118.3 (4)	C3C—C4C—C5C	118.0 (4)
C5A—C4A—H4A	126 (3)	C3C—C4C—H4C	120 (3)
C3A—C4A—H4A	116 (3)	C5C—C4C—H4C	122 (3)
C6A—C5A—C4A	122.4 (4)	C6C—C5C—C4C	122.3 (3)
C6A—C5A—Br2A	118.2 (3)	C6C—C5C—Br2C	118.8 (3)
C4A—C5A—Br2A	119.5 (3)	C4C—C5C—Br2C	118.9 (3)
C5A—C6A—C1A	118.7 (4)	C5C—C6C—C1C	119.1 (3)
C5A—C6A—H6A	122 (3)	C5C—C6C—H6C	120 (3)
C1A—C6A—H6A	119 (3)	C1C—C6C—H6C	121 (3)
N2A—N1A—C1A	115.7 (3)	N2C—N1C—C1C	115.4 (3)
N3A—N2A—N1A	172.8 (4)	N3C—N2C—N1C	172.5 (4)
C6B—C1B—C2B	119.5 (3)	N2D—N1D—C1D	115.3 (3)
C6B—C1B—N1B	122.5 (3)	N3D—N2D—N1D	172.4 (4)
C2B—C1B—N1B	118.0 (3)	C2D—C1D—C6D	119.4 (4)
C3B—C2B—C1B	120.3 (3)	C2D—C1D—N1D	117.8 (3)
C3B—C2B—Br1B	119.7 (3)	C6D—C1D—N1D	122.8 (4)
C1B—C2B—Br1B	120.0 (3)	C3D—C2D—C1D	120.9 (4)
C2B—C3B—C4B	120.5 (4)	C3D—C2D—Br1D	119.5 (3)
C2B—C3B—H3B	122 (3)	C1D—C2D—Br1D	119.7 (3)
C4B—C3B—H3B	117 (3)	C4D—C3D—C2D	120.3 (4)
C5B—C4B—C3B	118.9 (4)	C4D—C3D—H3D	118 (3)
C5B—C4B—H4B	124 (3)	C2D—C3D—H3D	122 (3)
C3B—C4B—H4B	117 (3)	C3D—C4D—C5D	118.9 (4)
C6B—C5B—C4B	121.7 (3)	C3D—C4D—H4D	125 (3)
C6B—C5B—Br2B	118.8 (3)	C5D—C4D—H4D	116 (3)
C4B—C5B—Br2B	119.5 (3)	C4D—C5D—C6D	121.9 (4)
C5B—C6B—C1B	119.2 (4)	C4D—C5D—Br2D	120.1 (3)
C5B—C6B—H6B	121 (3)	C6D—C5D—Br2D	117.9 (3)
C1B—C6B—H6B	120 (3)	C5D—C6D—C1D	118.6 (4)
N2B—N1B—C1B	115.0 (3)	C5D—C6D—H6D	125 (3)
N3B—N2B—N1B	172.9 (4)	C1D—C6D—H6D	117 (3)
C6A—C1A—C2A—C3A	−1.6 (6)	C6C—C1C—C2C—C3C	−0.7 (6)
N1A—C1A—C2A—C3A	179.1 (4)	N1C—C1C—C2C—C3C	179.5 (4)
C6A—C1A—C2A—Br1A	178.8 (3)	C6C—C1C—C2C—Br1C	178.4 (3)
N1A—C1A—C2A—Br1A	−0.6 (5)	N1C—C1C—C2C—Br1C	−1.4 (5)
C1A—C2A—C3A—C4A	1.2 (6)	C1C—C2C—C3C—C4C	0.4 (6)
Br1A—C2A—C3A—C4A	−179.1 (3)	Br1C—C2C—C3C—C4C	−178.7 (3)
C2A—C3A—C4A—C5A	−0.1 (7)	C2C—C3C—C4C—C5C	0.6 (6)
C3A—C4A—C5A—C6A	−0.6 (7)	C3C—C4C—C5C—C6C	−1.4 (6)
C3A—C4A—C5A—Br2A	−179.5 (3)	C3C—C4C—C5C—Br2C	−179.7 (3)
C4A—C5A—C6A—C1A	0.2 (7)	C4C—C5C—C6C—C1C	1.1 (6)
Br2A—C5A—C6A—C1A	179.2 (3)	Br2C—C5C—C6C—C1C	179.4 (3)
C2A—C1A—C6A—C5A	0.8 (6)	C2C—C1C—C6C—C5C	0.0 (6)
N1A—C1A—C6A—C5A	−179.8 (4)	N1C—C1C—C6C—C5C	179.8 (4)
C2A—C1A—N1A—N2A	−175.5 (4)	C2C—C1C—N1C—N2C	172.7 (4)
C6A—C1A—N1A—N2A	5.1 (6)	C6C—C1C—N1C—N2C	−7.1 (6)
C1A—N1A—N2A—N3A	176 (4)	C1C—N1C—N2C—N3C	−179 (100)
C6B—C1B—C2B—C3B	0.5 (6)	C1D—N1D—N2D—N3D	180 (100)
N1B—C1B—C2B—C3B	−179.3 (4)	N2D—N1D—C1D—C2D	171.9 (4)
C6B—C1B—C2B—Br1B	−179.4 (3)	N2D—N1D—C1D—C6D	−8.9 (6)
N1B—C1B—C2B—Br1B	0.7 (5)	C6D—C1D—C2D—C3D	0.8 (6)
C1B—C2B—C3B—C4B	0.0 (6)	N1D—C1D—C2D—C3D	−179.9 (4)
Br1B—C2B—C3B—C4B	180.0 (3)	C6D—C1D—C2D—Br1D	−178.7 (3)
C2B—C3B—C4B—C5B	−0.8 (6)	N1D—C1D—C2D—Br1D	0.5 (5)
C3B—C4B—C5B—C6B	1.1 (6)	C1D—C2D—C3D—C4D	0.1 (6)
C3B—C4B—C5B—Br2B	−179.3 (3)	Br1D—C2D—C3D—C4D	179.7 (3)
C4B—C5B—C6B—C1B	−0.5 (6)	C2D—C3D—C4D—C5D	−1.0 (6)
Br2B—C5B—C6B—C1B	179.8 (3)	C3D—C4D—C5D—C6D	0.9 (7)
C2B—C1B—C6B—C5B	−0.3 (5)	C3D—C4D—C5D—Br2D	−179.8 (3)
N1B—C1B—C6B—C5B	179.6 (4)	C4D—C5D—C6D—C1D	0.0 (6)
C6B—C1B—N1B—N2B	−11.9 (6)	Br2D—C5D—C6D—C1D	−179.3 (3)
C2B—C1B—N1B—N2B	168.0 (3)	C2D—C1D—C6D—C5D	−0.9 (6)
C1B—N1B—N2B—N3B	−177 (100)	N1D—C1D—C6D—C5D	179.9 (4)

2,4,6-tribromophenyl azide (8)

Crystal data

C6H2Br3N3	F(000) = 656
Mr = 355.84	Dx = 2.647 Mg m^−3
Monoclinic, P21/n	Melting point: not measured K
a = 3.8918 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.6900 (3) Å	µ = 13.50 mm^−1
c = 15.6965 (4) Å	T = 80 K
β = 95.665 (1)°	Block, colorless
V = 892.99 (4) Å^3	0.30 × 0.15 × 0.15 mm
Z = 4

Data collection

Bruker SMART CCD area detector system diffractometer	2611 independent reflections
Radiation source: rotating anode	2312 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
ω scans	θmax = 30.0°, θmin = 1.9°
Absorption correction: empirical (using intensity measurements) Program SADABS was used.	h = −5→5
Tmin = 0.107, Tmax = 0.237	k = −20→20
14037 measured reflections	l = −21→21

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)] = 0.022	Hydrogen site location: difference Fourier map
wR(F^2) = 0.054	Only H-atom coordinates refined
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0319P)^2] where P = (Fo^2 + 2Fc^2)/3
2611 reflections	(Δ/σ)max = 0.002
115 parameters	Δρmax = 0.79 e Å^−3
0 restraints	Δρmin = −1.35 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 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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.03359 (6)	0.956250 (15)	0.616004 (14)	0.01120 (6)
Br2	0.69874 (6)	0.848289 (15)	0.937789 (15)	0.01232 (6)
Br3	0.68958 (6)	1.220660 (15)	0.845804 (15)	0.01360 (6)
N1	0.2794 (6)	1.15350 (13)	0.68202 (14)	0.0148 (4)
N2	0.3569 (6)	1.14630 (13)	0.60688 (14)	0.0134 (4)
N3	0.4109 (6)	1.15073 (14)	0.53728 (14)	0.0186 (4)
C1	0.3788 (6)	1.07921 (15)	0.73877 (14)	0.0103 (4)
C2	0.2857 (6)	0.98809 (16)	0.72162 (14)	0.0102 (4)
C3	0.3772 (6)	0.91843 (16)	0.78010 (15)	0.0105 (4)
H3	0.303 (8)	0.858 (2)	0.765 (2)	0.013*
C4	0.5603 (6)	0.94159 (15)	0.85789 (14)	0.0100 (4)
C5	0.6508 (6)	1.03113 (16)	0.87822 (15)	0.0108 (4)
H5	0.790 (8)	1.044 (2)	0.9342 (19)	0.013*
C6	0.5596 (6)	1.09905 (15)	0.81822 (15)	0.0104 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.01419 (11)	0.01097 (11)	0.00801 (11)	−0.00163 (8)	−0.00116 (8)	−0.00080 (7)
Br2	0.01533 (11)	0.01002 (11)	0.01106 (11)	0.00169 (8)	−0.00145 (8)	0.00221 (8)
Br3	0.01858 (12)	0.00777 (11)	0.01415 (12)	−0.00196 (8)	0.00005 (8)	−0.00199 (8)
N1	0.0241 (10)	0.0106 (9)	0.0096 (9)	0.0035 (8)	0.0010 (8)	0.0014 (7)
N2	0.0188 (10)	0.0078 (9)	0.0130 (10)	−0.0019 (7)	−0.0006 (8)	0.0000 (7)
N3	0.0309 (12)	0.0127 (10)	0.0120 (10)	−0.0032 (8)	0.0010 (9)	0.0008 (8)
C1	0.0122 (10)	0.0095 (10)	0.0092 (10)	0.0021 (8)	0.0002 (8)	−0.0006 (8)
C2	0.0118 (9)	0.0110 (10)	0.0076 (10)	0.0003 (8)	0.0001 (8)	−0.0013 (8)
C3	0.0112 (10)	0.0106 (10)	0.0100 (10)	−0.0003 (8)	0.0015 (8)	−0.0015 (8)
C4	0.0104 (9)	0.0097 (10)	0.0100 (10)	0.0021 (8)	0.0014 (8)	0.0020 (8)
C5	0.0117 (9)	0.0130 (10)	0.0075 (10)	0.0014 (8)	0.0001 (8)	−0.0017 (8)
C6	0.0116 (9)	0.0082 (10)	0.0112 (10)	−0.0004 (7)	0.0007 (8)	−0.0025 (8)

Geometric parameters (Å, º)

Br1—C2	1.900 (2)	C1—C2	1.406 (3)
Br2—C4	1.900 (2)	C2—C3	1.397 (3)
Br3—C6	1.895 (2)	C3—C4	1.394 (3)
N1—N2	1.250 (3)	C3—H3	0.96 (3)
N1—C1	1.437 (3)	C4—C5	1.391 (3)
N2—N3	1.135 (3)	C5—C6	1.394 (3)
C1—C6	1.401 (3)	C5—H5	1.01 (3)
N2—N1—C1	116.43 (19)	C2—C3—H3	117.8 (19)
N3—N2—N1	171.2 (2)	C5—C4—C3	121.9 (2)
C6—C1—C2	117.8 (2)	C5—C4—Br2	118.82 (17)
C6—C1—N1	118.3 (2)	C3—C4—Br2	119.30 (17)
C2—C1—N1	123.8 (2)	C4—C5—C6	118.7 (2)
C3—C2—C1	121.8 (2)	C4—C5—H5	118.9 (17)
C3—C2—Br1	117.98 (17)	C6—C5—H5	122.3 (17)
C1—C2—Br1	120.18 (17)	C5—C6—C1	121.6 (2)
C4—C3—C2	118.1 (2)	C5—C6—Br3	118.43 (17)
C4—C3—H3	124.0 (19)	C1—C6—Br3	119.93 (17)
C1—N1—N2—N3	−175.5 (17)	C2—C3—C4—Br2	−178.48 (17)
N2—N1—C1—C6	129.3 (2)	C3—C4—C5—C6	−1.0 (3)
N2—N1—C1—C2	−55.0 (3)	Br2—C4—C5—C6	177.73 (17)
C6—C1—C2—C3	−1.9 (3)	C4—C5—C6—C1	0.3 (3)
N1—C1—C2—C3	−177.6 (2)	C4—C5—C6—Br3	−179.14 (17)
C6—C1—C2—Br1	178.98 (17)	C2—C1—C6—C5	1.1 (3)
N1—C1—C2—Br1	3.3 (3)	N1—C1—C6—C5	177.0 (2)
C1—C2—C3—C4	1.2 (3)	C2—C1—C6—Br3	−179.47 (17)
Br1—C2—C3—C4	−179.60 (17)	N1—C1—C6—Br3	−3.5 (3)
C2—C3—C4—C5	0.3 (3)