3,5-Dihalo-4-hydroxybenzonitriles: isostructures, polymorphs and solvates

3,5-Dichloro-4-hydroxybenzonitrile and its solvates with benzene and xylene assemble in chain-like arrangements held together by OH...NC interactions. Two polymorphs each of the corresponding dibromo and diiodo compounds form similar chains which are then bound together by X...X interactions to form approximately planar sheets. These sheets are essentially identical in all four of the bromo and iodo compounds and have approximate p2gg two-dimensional symmetry. These four compounds form an extreme example of two-dimensional isostructuality. The polymorphs differ in the stacking arrangements. One of the Br polymorphs is isostructural with one of the I polymorphs.

Computing details

For all compounds, data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures

(MCl) 3,5-dichloro-4-hydroxybenzonitrile

Crystal data

C7H3Cl2NO	Z = 4
Mr = 188.00	F(000) = 376
Triclinic, P1	Dx = 1.686 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3325 (18) Å	Cell parameters from 1913 reflections
b = 8.999 (2) Å	θ = 2.8–25.9°
c = 12.221 (3) Å	µ = 0.81 mm^−1
α = 78.65 (1)°	T = 174 K
β = 74.39 (1)°	Plate, colorless
γ = 74.23 (1)°	0.40 × 0.25 × 0.10 mm
V = 740.7 (3) Å^3

Data collection

Siemens area detector diffractometer	3362 independent reflections
Radiation source: fine-focus sealed tube	2309 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995'	h = −9→9
Tmin = 0.80, Tmax = 0.92	k = −11→11
8796 measured reflections	l = −15→15

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: inferred from neighbouring sites
wR(F^2) = 0.095	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.029P)^2 + 0.054P] where P = (Fo^2 + 2Fc^2)/3
3362 reflections	(Δ/σ)max = 0.003
199 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

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

	x	y	z	Uiso*/Ueq
Cl13	0.44792 (10)	0.47127 (7)	0.27629 (6)	0.03104 (18)
Cl15	0.04364 (11)	0.56389 (8)	0.70496 (6)	0.0365 (2)
O14	0.2177 (3)	0.38864 (19)	0.51401 (15)	0.0301 (4)
H14	0.2711	0.3403	0.4571	0.036*
N17	0.3350 (4)	1.1216 (3)	0.4097 (2)	0.0372 (6)
C17	0.3216 (4)	0.9954 (3)	0.4245 (2)	0.0287 (6)
C11	0.2982 (4)	0.8376 (3)	0.4456 (2)	0.0251 (6)
C12	0.3819 (4)	0.7403 (3)	0.3608 (2)	0.0234 (6)
H12	0.4580	0.7758	0.2892	0.028*
C13	0.3519 (4)	0.5911 (3)	0.3828 (2)	0.0219 (6)
C14	0.2479 (4)	0.5332 (3)	0.4884 (2)	0.0223 (6)
C15	0.1700 (4)	0.6329 (3)	0.5724 (2)	0.0234 (6)
C16	0.1923 (4)	0.7835 (3)	0.5512 (2)	0.0265 (6)
H16	0.1353	0.8504	0.6087	0.032*
Cl23	0.26550 (10)	1.08330 (7)	1.14836 (5)	0.02751 (17)
Cl25	0.18386 (10)	1.09927 (7)	0.72286 (5)	0.03108 (18)
O24	0.2355 (3)	1.22312 (18)	0.90769 (15)	0.0291 (4)
H24	0.2479	1.2578	0.9636	0.035*
N27	0.2523 (3)	0.4597 (3)	1.0168 (2)	0.0349 (6)
C27	0.2504 (4)	0.5887 (3)	1.0014 (2)	0.0267 (6)
C21	0.2481 (4)	0.7533 (3)	0.9794 (2)	0.0214 (5)
C22	0.2609 (3)	0.8279 (3)	1.0652 (2)	0.0228 (6)
H22	0.2730	0.7719	1.1384	0.027*
C23	0.2557 (3)	0.9854 (3)	1.0420 (2)	0.0209 (5)
C24	0.2380 (3)	1.0709 (3)	0.9358 (2)	0.0207 (5)
C25	0.2188 (3)	0.9925 (3)	0.8520 (2)	0.0215 (5)
C26	0.2255 (3)	0.8356 (3)	0.8729 (2)	0.0229 (6)
H26	0.2148	0.7836	0.8152	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl13	0.0393 (4)	0.0233 (3)	0.0302 (4)	−0.0077 (3)	−0.0021 (3)	−0.0106 (3)
Cl15	0.0483 (5)	0.0360 (4)	0.0256 (4)	−0.0190 (3)	0.0002 (3)	−0.0039 (3)
O14	0.0452 (12)	0.0186 (9)	0.0287 (10)	−0.0137 (8)	−0.0055 (9)	−0.0033 (8)
N17	0.0551 (17)	0.0206 (12)	0.0396 (15)	−0.0118 (11)	−0.0139 (13)	−0.0041 (11)
C17	0.0371 (16)	0.0232 (15)	0.0291 (15)	−0.0088 (12)	−0.0106 (12)	−0.0044 (12)
C11	0.0321 (15)	0.0183 (13)	0.0289 (15)	−0.0085 (11)	−0.0117 (12)	−0.0021 (11)
C12	0.0282 (14)	0.0195 (13)	0.0243 (14)	−0.0060 (11)	−0.0085 (11)	−0.0028 (11)
C13	0.0251 (14)	0.0172 (13)	0.0249 (14)	−0.0033 (11)	−0.0073 (11)	−0.0063 (10)
C14	0.0270 (14)	0.0158 (12)	0.0259 (14)	−0.0067 (11)	−0.0086 (11)	−0.0011 (11)
C15	0.0306 (15)	0.0210 (13)	0.0185 (13)	−0.0079 (11)	−0.0044 (11)	−0.0015 (10)
C16	0.0339 (16)	0.0211 (13)	0.0273 (14)	−0.0055 (12)	−0.0085 (12)	−0.0086 (11)
Cl23	0.0384 (4)	0.0216 (3)	0.0270 (3)	−0.0093 (3)	−0.0092 (3)	−0.0079 (3)
Cl25	0.0456 (4)	0.0270 (4)	0.0231 (3)	−0.0130 (3)	−0.0093 (3)	−0.0008 (3)
O24	0.0482 (12)	0.0173 (9)	0.0265 (10)	−0.0138 (8)	−0.0100 (9)	−0.0029 (8)
N27	0.0494 (16)	0.0202 (12)	0.0380 (14)	−0.0111 (11)	−0.0112 (12)	−0.0050 (11)
C27	0.0299 (15)	0.0233 (14)	0.0275 (15)	−0.0046 (12)	−0.0073 (12)	−0.0061 (12)
C21	0.0225 (14)	0.0128 (12)	0.0284 (14)	−0.0042 (10)	−0.0037 (11)	−0.0041 (10)
C22	0.0265 (14)	0.0194 (13)	0.0225 (13)	−0.0055 (11)	−0.0055 (11)	−0.0028 (11)
C23	0.0224 (13)	0.0186 (13)	0.0237 (13)	−0.0054 (10)	−0.0039 (11)	−0.0087 (11)
C24	0.0237 (13)	0.0143 (12)	0.0248 (14)	−0.0083 (10)	−0.0019 (11)	−0.0034 (10)
C25	0.0217 (13)	0.0222 (13)	0.0193 (13)	−0.0064 (11)	−0.0023 (11)	−0.0010 (10)
C26	0.0240 (14)	0.0224 (14)	0.0250 (14)	−0.0065 (11)	−0.0049 (11)	−0.0086 (11)

Geometric parameters (Å, º)

Cl13—C13	1.731 (2)	Cl23—C23	1.734 (2)
Cl15—C15	1.726 (3)	Cl25—C25	1.722 (2)
O14—C14	1.341 (3)	O24—C24	1.341 (3)
O14—H14	0.8400	O24—H24	0.8400
N17—C17	1.141 (3)	N27—C27	1.135 (3)
C17—C11	1.442 (3)	C27—C21	1.449 (3)
C11—C16	1.387 (4)	C21—C22	1.387 (3)
C11—C12	1.393 (3)	C21—C26	1.393 (3)
C12—C13	1.382 (3)	C22—C23	1.382 (3)
C12—H12	0.9500	C22—H22	0.9500
C13—C14	1.394 (3)	C23—C24	1.392 (3)
C14—C15	1.397 (3)	C24—C25	1.408 (3)
C15—C16	1.375 (3)	C25—C26	1.375 (3)
C16—H16	0.9500	C26—H26	0.9500
C14—O14—H14	109.5	C24—O24—H24	109.5
N17—C17—C11	178.1 (3)	N27—C27—C21	178.9 (3)
C16—C11—C12	120.4 (2)	C22—C21—C26	120.9 (2)
C16—C11—C17	119.3 (2)	C22—C21—C27	120.0 (2)
C12—C11—C17	120.2 (2)	C26—C21—C27	119.0 (2)
C13—C12—C11	118.7 (2)	C23—C22—C21	118.6 (2)
C13—C12—H12	120.7	C23—C22—H22	120.7
C11—C12—H12	120.7	C21—C22—H22	120.7
C12—C13—C14	122.1 (2)	C22—C23—C24	122.2 (2)
C12—C13—Cl13	119.14 (19)	C22—C23—Cl23	119.8 (2)
C14—C13—Cl13	118.77 (19)	C24—C23—Cl23	118.04 (18)
O14—C14—C13	124.1 (2)	O24—C24—C23	124.8 (2)
O14—C14—C15	118.3 (2)	O24—C24—C25	117.5 (2)
C13—C14—C15	117.6 (2)	C23—C24—C25	117.7 (2)
C16—C15—C14	121.3 (2)	C26—C25—C24	121.0 (2)
C16—C15—Cl15	119.87 (19)	C26—C25—Cl25	120.85 (19)
C14—C15—Cl15	118.79 (19)	C24—C25—Cl25	118.11 (18)
C15—C16—C11	119.8 (2)	C25—C26—C21	119.5 (2)
C15—C16—H16	120.1	C25—C26—H26	120.2
C11—C16—H16	120.1	C21—C26—H26	120.2

(MCl-Bz) 3,5-dichloro-4-hydroxybenzonitrile / 1/2 benzene

Crystal data

C7H3Cl2NO·0.5(C6H6)	Z = 2
Mr = 227.06	F(000) = 230
Triclinic, P1	Dx = 1.563 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.420 (2) Å	Cell parameters from 2490 reflections
b = 8.386 (2) Å	θ = 2.6–27.5°
c = 8.808 (2) Å	µ = 0.63 mm^−1
α = 73.82 (1)°	T = 174 K
β = 66.99 (1)°	Prism, colorless
γ = 79.04 (1)°	0.50 × 0.45 × 0.40 mm
V = 482.4 (2) Å^3

Data collection

Siemans area detector diffractometer	2141 independent reflections
Radiation source: fine-focus sealed tube	2086 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995'	h = −9→9
Tmin = 0.74, Tmax = 0.78	k = −10→10
5442 measured reflections	l = −11→11

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)] = 0.025	H-atom parameters constrained
wR(F^2) = 0.075	w = 1/[σ^2(Fo^2) + (0.039P)^2 + 0.211P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.013
2141 reflections	Δρmax = 0.46 e Å^−3
148 parameters	Δρmin = −0.18 e Å^−3
0 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: 0.022 (4)

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

	x	y	z	Uiso*/Ueq
Cl3	0.77557 (5)	0.61464 (4)	0.47223 (4)	0.02601 (11)
Cl5	0.63236 (6)	−0.03101 (4)	0.67049 (5)	0.03356 (12)
O4	0.83045 (15)	0.25566 (13)	0.44919 (12)	0.0298 (2)
H4	0.8866	0.3412	0.3865	0.036*
N7	0.11355 (19)	0.41555 (16)	1.15910 (16)	0.0313 (3)
C7	0.2352 (2)	0.38929 (17)	1.03757 (17)	0.0246 (3)
C1	0.38998 (19)	0.35638 (17)	0.88546 (16)	0.0225 (3)
C2	0.49726 (19)	0.48661 (17)	0.76795 (16)	0.0228 (3)
H2	0.4692	0.5958	0.7882	0.027*
C3	0.64521 (19)	0.45385 (16)	0.62150 (16)	0.0208 (3)
C4	0.69016 (18)	0.29445 (16)	0.58880 (16)	0.0217 (3)
C5	0.57927 (19)	0.16651 (16)	0.70987 (17)	0.0224 (3)
C6	0.43020 (19)	0.19575 (17)	0.85661 (16)	0.0230 (3)
H6	0.3563	0.1079	0.9366	0.028*
C11	1.0772 (2)	0.85307 (19)	0.0809 (2)	0.0331 (3)
H11	1.1304	0.7521	0.1360	0.040*
C12	0.9788 (2)	0.9766 (2)	0.16852 (19)	0.0330 (3)
H12	0.9643	0.9607	0.2837	0.040*
C13	0.9019 (2)	1.12330 (19)	0.0873 (2)	0.0325 (3)
H13	0.8343	1.2083	0.1469	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl3	0.02473 (18)	0.02516 (18)	0.02235 (18)	−0.00724 (12)	−0.00319 (13)	−0.00083 (12)
Cl5	0.0370 (2)	0.02394 (19)	0.0332 (2)	−0.00511 (14)	−0.00152 (15)	−0.01104 (14)
O4	0.0291 (5)	0.0301 (5)	0.0217 (5)	−0.0070 (4)	0.0044 (4)	−0.0096 (4)
N7	0.0312 (6)	0.0322 (7)	0.0242 (6)	−0.0070 (5)	0.0004 (5)	−0.0094 (5)
C7	0.0252 (7)	0.0249 (7)	0.0226 (6)	−0.0055 (5)	−0.0059 (5)	−0.0056 (5)
C1	0.0197 (6)	0.0285 (7)	0.0170 (6)	−0.0029 (5)	−0.0035 (5)	−0.0058 (5)
C2	0.0214 (6)	0.0247 (6)	0.0213 (6)	−0.0022 (5)	−0.0055 (5)	−0.0067 (5)
C3	0.0197 (6)	0.0228 (6)	0.0180 (6)	−0.0051 (5)	−0.0053 (5)	−0.0015 (5)
C4	0.0185 (6)	0.0271 (7)	0.0176 (6)	−0.0020 (5)	−0.0038 (5)	−0.0062 (5)
C5	0.0228 (6)	0.0219 (6)	0.0219 (6)	−0.0020 (5)	−0.0066 (5)	−0.0059 (5)
C6	0.0217 (6)	0.0257 (6)	0.0193 (6)	−0.0051 (5)	−0.0052 (5)	−0.0028 (5)
C11	0.0328 (7)	0.0262 (7)	0.0419 (8)	−0.0060 (6)	−0.0169 (7)	−0.0031 (6)
C12	0.0324 (8)	0.0419 (9)	0.0257 (7)	−0.0133 (6)	−0.0076 (6)	−0.0068 (6)
C13	0.0267 (7)	0.0331 (8)	0.0400 (8)	−0.0043 (6)	−0.0069 (6)	−0.0181 (6)

Geometric parameters (Å, º)

Cl3—C3	1.7309 (13)	C4—C5	1.4062 (18)
Cl5—C5	1.7276 (14)	C5—C6	1.3820 (18)
O4—C4	1.3398 (15)	C6—H6	0.9500
O4—H4	0.8400	C11—C12	1.386 (2)
N7—C7	1.1442 (19)	C11—C13^i	1.388 (2)
C7—C1	1.4399 (18)	C11—H11	0.9500
C1—C6	1.3953 (19)	C12—C13	1.383 (2)
C1—C2	1.3979 (19)	C12—H12	0.9500
C2—C3	1.3858 (18)	C13—C11^i	1.388 (2)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.3967 (19)
C4—O4—H4	109.5	C6—C5—Cl5	120.03 (10)
N7—C7—C1	179.29 (15)	C4—C5—Cl5	118.23 (10)
C6—C1—C2	120.88 (12)	C5—C6—C1	118.95 (12)
C6—C1—C7	119.76 (12)	C5—C6—H6	120.5
C2—C1—C7	119.36 (12)	C1—C6—H6	120.5
C3—C2—C1	118.91 (12)	C12—C11—C13^i	120.08 (15)
C3—C2—H2	120.5	C12—C11—H11	120.0
C1—C2—H2	120.5	C13^i—C11—H11	120.0
C2—C3—C4	121.78 (12)	C11—C12—C13	119.56 (15)
C2—C3—Cl3	119.53 (10)	C11—C12—H12	120.2
C4—C3—Cl3	118.68 (10)	C13—C12—H12	120.2
O4—C4—C3	124.41 (12)	C12—C13—C11^i	120.36 (14)
O4—C4—C5	117.84 (12)	C12—C13—H13	119.8
C3—C4—C5	117.74 (11)	C11^i—C13—H13	119.8
C6—C5—C4	121.74 (12)

Symmetry code: (i) −x+2, −y+2, −z.

(MCl-Xy) 3,5-dichloro-4-hydroxybenzonitrile / 1/4 p-xylene

Crystal data

C7H3Cl2NO·0.25(C8H10)	F(000) = 434
Mr = 214.55	Dx = 1.539 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3547 reflections
a = 4.5522 (11) Å	θ = 2.7–27.2°
b = 15.067 (4) Å	µ = 0.65 mm^−1
c = 13.636 (3) Å	T = 174 K
β = 98.00 (1)°	Needle, colorless
V = 926.2 (4) Å^3	0.40 × 0.15 × 0.10 mm
Z = 4

Data collection

Siemens area detector diffractometer	1636 independent reflections
Radiation source: fine-focus sealed tube	1317 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995'	h = −5→5
Tmin = 0.88, Tmax = 0.94	k = −17→17
8934 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)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.079	w = 1/[σ^2(Fo^2) + (0.022P)^2 + 0.43P] where P = (Fo^2 + 2Fc^2)/3
S = 1.22	(Δ/σ)max = 0.023
1636 reflections	Δρmax = 0.22 e Å^−3
151 parameters	Δρmin = −0.19 e Å^−3
67 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: 0.0043 (16)

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
04	1.2136 (4)	0.84495 (12)	0.74697 (13)	0.0351 (5)
H4	1.2799	0.8003	0.7797	0.042*
C4	0.9847 (5)	0.82074 (17)	0.67956 (18)	0.0249 (6)
Cl3	1.04842 (16)	0.65090 (4)	0.74032 (5)	0.0376 (2)
C3	0.8767 (5)	0.73432 (17)	0.66611 (18)	0.0245 (6)
C2	0.6421 (6)	0.71394 (17)	0.59419 (18)	0.0276 (6)
H2	0.5706	0.6548	0.5865	0.033*
C1	0.5117 (5)	0.78098 (17)	0.53313 (18)	0.0257 (6)
N7	0.0819 (5)	0.74320 (16)	0.39527 (18)	0.0423 (6)
C6	0.6128 (6)	0.86740 (17)	0.54498 (19)	0.0277 (6)
H6	0.5228	0.9131	0.5031	0.033*
Cl5	0.96867 (17)	0.99512 (5)	0.63438 (6)	0.0432 (3)
C5	0.8453 (6)	0.88677 (17)	0.61796 (18)	0.0260 (6)
C7	0.2710 (6)	0.76007 (18)	0.4564 (2)	0.0307 (7)
C11	0.176 (3)	0.508 (2)	0.4806 (19)	0.0328 (17)	0.25
C12	0.357 (3)	0.528 (2)	0.4094 (19)	0.0324 (16)	0.25
H12A	0.2690	0.5491	0.3462	0.039*	0.25
C13	0.663 (3)	0.520 (2)	0.4292 (19)	0.0325 (17)	0.25
H13A	0.7814	0.5346	0.3794	0.039*	0.25
C14	0.800 (3)	0.490 (2)	0.5209 (19)	0.0328 (17)	0.25
C15	0.619 (3)	0.469 (2)	0.5921 (19)	0.0324 (16)	0.25
H15A	0.7072	0.4477	0.6551	0.039*	0.25
C16	0.313 (3)	0.478 (2)	0.5724 (19)	0.0325 (17)	0.25
H16A	0.1950	0.4634	0.6224	0.039*	0.25
C17	−0.156 (4)	0.517 (3)	0.460 (6)	0.046 (3)	0.25
H17A	−0.2069	0.5760	0.4338	0.069*	0.25
H17B	−0.2404	0.5077	0.5215	0.069*	0.25
H17C	−0.2354	0.4719	0.4112	0.069*	0.25
C18	1.132 (4)	0.480 (3)	0.543 (6)	0.046 (3)	0.25
H18A	1.2013	0.5051	0.6081	0.069*	0.25
H18B	1.2237	0.5126	0.4923	0.069*	0.25
H18C	1.1858	0.4175	0.5412	0.069*	0.25

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
04	0.0359 (11)	0.0308 (11)	0.0326 (11)	0.0019 (9)	−0.0170 (9)	−0.0008 (9)
C4	0.0239 (15)	0.0279 (15)	0.0213 (14)	0.0023 (11)	−0.0028 (12)	−0.0033 (11)
Cl3	0.0454 (5)	0.0297 (4)	0.0346 (4)	0.0070 (3)	−0.0050 (3)	0.0058 (3)
C3	0.0244 (15)	0.0267 (15)	0.0220 (14)	0.0050 (12)	0.0017 (12)	0.0025 (11)
C2	0.0278 (15)	0.0260 (15)	0.0288 (15)	−0.0025 (12)	0.0035 (12)	−0.0067 (12)
C1	0.0204 (14)	0.0328 (16)	0.0229 (14)	−0.0006 (12)	−0.0011 (11)	−0.0039 (12)
N7	0.0375 (15)	0.0475 (16)	0.0375 (14)	−0.0058 (12)	−0.0097 (13)	−0.0027 (12)
C6	0.0263 (15)	0.0290 (15)	0.0263 (15)	0.0038 (12)	−0.0016 (12)	0.0031 (12)
Cl5	0.0510 (5)	0.0253 (4)	0.0469 (5)	−0.0051 (4)	−0.0162 (4)	−0.0002 (3)
C5	0.0271 (15)	0.0244 (14)	0.0251 (15)	−0.0012 (11)	−0.0010 (12)	−0.0012 (11)
C7	0.0302 (17)	0.0318 (16)	0.0290 (15)	−0.0010 (13)	0.0003 (14)	−0.0007 (13)
C11	0.038 (4)	0.021 (3)	0.041 (4)	0.001 (3)	0.009 (3)	−0.003 (3)
C12	0.043 (4)	0.027 (3)	0.027 (3)	−0.001 (3)	0.005 (3)	0.001 (2)
C13	0.048 (5)	0.022 (3)	0.031 (4)	−0.003 (4)	0.017 (3)	−0.003 (3)
C14	0.038 (4)	0.021 (3)	0.041 (4)	0.001 (3)	0.009 (3)	−0.003 (3)
C15	0.043 (4)	0.027 (3)	0.027 (3)	−0.001 (3)	0.005 (3)	0.001 (2)
C16	0.048 (5)	0.022 (3)	0.031 (4)	−0.003 (4)	0.017 (3)	−0.003 (3)
C17	0.043 (5)	0.044 (5)	0.051 (5)	0.001 (5)	0.006 (6)	−0.007 (5)
C18	0.043 (5)	0.044 (5)	0.051 (5)	0.001 (5)	0.006 (6)	−0.007 (5)

Geometric parameters (Å, º)

04—C4	1.341 (3)	C11—C17	1.5032 (11)
04—H4	0.8400	C12—C13	1.3899 (10)
C4—C3	1.395 (4)	C12—H12A	0.9500
C4—C5	1.396 (3)	C13—C14	1.3930 (10)
Cl3—C3	1.730 (2)	C13—H13A	0.9500
C3—C2	1.380 (3)	C14—C15	1.3929 (10)
C2—C1	1.388 (3)	C14—C18	1.5032 (12)
C2—H2	0.9500	C15—C16	1.3899 (10)
C1—C6	1.383 (4)	C15—H15A	0.9500
C1—C7	1.441 (4)	C16—H16A	0.9500
N7—C7	1.140 (3)	C17—H17A	0.9800
C6—C5	1.379 (3)	C17—H17B	0.9800
C6—H6	0.9500	C17—H17C	0.9800
Cl5—C5	1.731 (3)	C18—H18A	0.9800
C11—C12	1.3929 (10)	C18—H18B	0.9800
C11—C16	1.3930 (10)	C18—H18C	0.9800
C4—04—H4	109.5	N7—C7—C1	179.5 (3)
04—C4—C3	124.8 (2)	C12—C11—C16	117.77 (13)
04—C4—C5	117.6 (2)	C12—C11—C17	122 (4)
C3—C4—C5	117.6 (2)	C16—C11—C17	121 (4)
C2—C3—C4	121.6 (2)	C13—C12—C11	121.12 (13)
C2—C3—Cl3	119.7 (2)	C13—C12—H12A	119.4
C4—C3—Cl3	118.61 (19)	C11—C12—H12A	119.4
C3—C2—C1	119.2 (2)	C12—C13—C14	121.10 (13)
C3—C2—H2	120.4	C12—C13—H13A	119.4
C1—C2—H2	120.4	C14—C13—H13A	119.4
C6—C1—C2	120.5 (2)	C15—C14—C13	117.77 (13)
C6—C1—C7	119.9 (2)	C15—C14—C18	121 (4)
C2—C1—C7	119.7 (2)	C13—C14—C18	121 (4)
C5—C6—C1	119.5 (2)	C16—C15—C14	121.12 (13)
C5—C6—H6	120.2	C16—C15—H15A	119.4
C1—C6—H6	120.2	C14—C15—H15A	119.4
C6—C5—C4	121.5 (2)	C15—C16—C11	121.10 (13)
C6—C5—Cl5	119.7 (2)	C15—C16—H16A	119.5
C4—C5—Cl5	118.82 (19)	C11—C16—H16A	119.5

(MBr-A) 3,5-dibromo-4-hydroxybenzonitrile - polymorph A

Crystal data

C7H3Br2NO	Z = 4
Mr = 276.92	F(000) = 520
Triclinic, P1	Dx = 2.348 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.244 (2) Å	Cell parameters from 2861 reflections
b = 9.120 (2) Å	θ = 2.4–27.5°
c = 11.687 (3) Å	µ = 10.28 mm^−1
α = 95.60 (1)°	T = 174 K
β = 108.55 (1)°	Prism, colorless
γ = 106.13 (1)°	0.20 × 0.15 × 0.15 mm
V = 783.4 (3) Å^3

Data collection

Siemens area detector diffractometer	3568 independent reflections
Radiation source: fine-focus sealed tube	3107 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995'	h = −10→10
Tmin = 0.174, Tmax = 0.214	k = −11→11
9376 measured reflections	l = −15→15

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.079	w = 1/[σ^2(Fo^2) + (0.028P)^2 + 2.2P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.006
3568 reflections	Δρmax = 0.65 e Å^−3
200 parameters	Δρmin = −0.61 e Å^−3
0 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: 0.0029 (3)

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

	x	y	z	Uiso*/Ueq
C11	0.3313 (5)	0.5626 (5)	0.7730 (4)	0.0191 (8)
C12	0.2655 (6)	0.6579 (5)	0.6969 (4)	0.0203 (8)
H12	0.2423	0.7459	0.7300	0.024*
Br13	0.15142 (6)	0.75285 (5)	0.46807 (4)	0.02491 (12)
C13	0.2350 (6)	0.6227 (5)	0.5733 (4)	0.0214 (8)
C14	0.2638 (6)	0.4918 (5)	0.5218 (4)	0.0202 (8)
O14	0.2313 (4)	0.4505 (4)	0.4000 (3)	0.0280 (7)
H14	0.1922	0.5149	0.3626	0.034*
Br15	0.36496 (6)	0.21886 (5)	0.53131 (4)	0.02649 (13)
C15	0.3292 (5)	0.3990 (4)	0.5995 (4)	0.0184 (8)
C16	0.3655 (5)	0.4331 (5)	0.7244 (4)	0.0196 (8)
H16	0.4130	0.3697	0.7766	0.023*
N17	0.4017 (5)	0.6404 (4)	1.0065 (3)	0.0275 (8)
C17	0.3704 (6)	0.6033 (5)	0.9032 (4)	0.0219 (9)
C21	0.1629 (5)	0.2828 (5)	0.0757 (4)	0.0191 (8)
C22	0.2438 (5)	0.2029 (5)	0.1612 (4)	0.0194 (8)
H22	0.2725	0.2367	0.2469	0.023*
Br23	0.38345 (6)	−0.03975 (5)	0.23138 (4)	0.02698 (13)
C23	0.2809 (5)	0.0742 (5)	0.1186 (4)	0.0201 (8)
O24	0.2752 (4)	−0.1024 (3)	−0.0518 (3)	0.0265 (7)
H24	0.3238	−0.1414	0.0066	0.040*
C24	0.2412 (6)	0.0233 (4)	−0.0067 (4)	0.0205 (8)
Br25	0.10256 (6)	0.03445 (5)	−0.25968 (4)	0.02639 (13)
C25	0.1602 (5)	0.1054 (4)	−0.0892 (3)	0.0175 (8)
C26	0.1214 (5)	0.2337 (5)	−0.0497 (4)	0.0192 (8)
H26	0.0669	0.2884	−0.1074	0.023*
C27	0.1232 (6)	0.4164 (5)	0.1214 (4)	0.0242 (9)
N27	0.0903 (6)	0.5194 (5)	0.1612 (3)	0.0331 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.0168 (19)	0.0197 (19)	0.0177 (18)	0.0034 (16)	0.0049 (15)	0.0023 (15)
C12	0.022 (2)	0.0173 (19)	0.023 (2)	0.0074 (16)	0.0083 (17)	0.0039 (15)
Br13	0.0301 (3)	0.0252 (2)	0.0237 (2)	0.01436 (19)	0.00877 (18)	0.01145 (16)
C13	0.024 (2)	0.0183 (19)	0.022 (2)	0.0083 (17)	0.0070 (17)	0.0075 (16)
C14	0.022 (2)	0.021 (2)	0.0169 (18)	0.0061 (17)	0.0068 (16)	0.0027 (15)
O14	0.043 (2)	0.0292 (16)	0.0175 (14)	0.0196 (15)	0.0109 (14)	0.0078 (12)
Br15	0.0380 (3)	0.0234 (2)	0.0232 (2)	0.01689 (19)	0.01198 (19)	0.00432 (16)
C15	0.019 (2)	0.0151 (18)	0.0216 (19)	0.0064 (16)	0.0076 (16)	0.0011 (15)
C16	0.018 (2)	0.0182 (19)	0.0213 (19)	0.0055 (16)	0.0055 (16)	0.0049 (15)
N17	0.039 (2)	0.0266 (19)	0.0198 (18)	0.0158 (17)	0.0096 (16)	0.0042 (15)
C17	0.022 (2)	0.0162 (19)	0.026 (2)	0.0086 (16)	0.0058 (17)	0.0036 (16)
C21	0.017 (2)	0.0172 (19)	0.023 (2)	0.0051 (16)	0.0086 (16)	0.0043 (16)
C22	0.018 (2)	0.0182 (19)	0.0197 (19)	0.0036 (16)	0.0065 (16)	0.0036 (15)
Br23	0.0349 (3)	0.0253 (2)	0.0239 (2)	0.01680 (19)	0.00730 (18)	0.01010 (17)
C23	0.018 (2)	0.0189 (19)	0.024 (2)	0.0062 (16)	0.0074 (16)	0.0092 (16)
O24	0.0357 (18)	0.0250 (15)	0.0245 (15)	0.0199 (14)	0.0098 (14)	0.0056 (12)
C24	0.021 (2)	0.0153 (18)	0.025 (2)	0.0055 (16)	0.0098 (17)	0.0032 (16)
Br25	0.0372 (3)	0.0276 (2)	0.0184 (2)	0.0156 (2)	0.01084 (18)	0.00519 (16)
C25	0.017 (2)	0.0186 (19)	0.0158 (18)	0.0034 (16)	0.0066 (15)	0.0036 (15)
C26	0.0155 (19)	0.0209 (19)	0.0222 (19)	0.0071 (16)	0.0068 (16)	0.0055 (16)
C27	0.031 (2)	0.026 (2)	0.0169 (19)	0.0116 (19)	0.0071 (17)	0.0086 (16)
N27	0.052 (3)	0.033 (2)	0.0218 (18)	0.028 (2)	0.0115 (18)	0.0052 (16)

Geometric parameters (Å, º)

C11—C12	1.396 (5)	C21—C26	1.391 (5)
C11—C16	1.397 (5)	C21—C22	1.401 (5)
C11—C17	1.438 (6)	C21—C27	1.443 (5)
C12—C13	1.373 (6)	C22—C23	1.379 (6)
C12—H12	0.9500	C22—H22	0.9500
Br13—C13	1.896 (4)	Br23—C23	1.892 (4)
C13—C14	1.398 (5)	C23—C24	1.395 (6)
C14—O14	1.356 (5)	O24—C24	1.351 (5)
C14—C15	1.386 (5)	O24—H24	0.8400
O14—H14	0.8400	C24—C25	1.395 (5)
Br15—C15	1.893 (4)	Br25—C25	1.894 (4)
C15—C16	1.378 (5)	C25—C26	1.372 (5)
C16—H16	0.9500	C26—H26	0.9500
N17—C17	1.145 (5)	C27—N27	1.144 (5)
C12—C11—C16	120.6 (4)	C26—C21—C22	120.7 (4)
C12—C11—C17	118.9 (4)	C26—C21—C27	121.2 (4)
C16—C11—C17	120.4 (4)	C22—C21—C27	118.1 (4)
C13—C12—C11	119.0 (4)	C23—C22—C21	118.7 (4)
C13—C12—H12	120.5	C23—C22—H22	120.6
C11—C12—H12	120.5	C21—C22—H22	120.6
C12—C13—C14	121.6 (4)	C22—C23—C24	121.6 (4)
C12—C13—Br13	120.1 (3)	C22—C23—Br23	119.7 (3)
C14—C13—Br13	118.4 (3)	C24—C23—Br23	118.7 (3)
O14—C14—C15	118.2 (3)	C24—O24—H24	109.5
O14—C14—C13	123.6 (4)	O24—C24—C23	123.2 (4)
C15—C14—C13	118.3 (4)	O24—C24—C25	118.6 (3)
C14—O14—H14	109.5	C23—C24—C25	118.1 (3)
C16—C15—C14	121.7 (3)	C26—C25—C24	121.7 (4)
C16—C15—Br15	119.3 (3)	C26—C25—Br25	120.1 (3)
C14—C15—Br15	119.0 (3)	C24—C25—Br25	118.2 (3)
C15—C16—C11	118.9 (4)	C25—C26—C21	119.2 (4)
C15—C16—H16	120.6	C25—C26—H26	120.4
C11—C16—H16	120.6	C21—C26—H26	120.4
N17—C17—C11	177.8 (4)	N27—C27—C21	177.3 (5)

(MBr-B) 3,5-dibromo-4-hydroxybenzonitrile

Crystal data

C7H3Br2NO	Z = 4
Mr = 276.92	F(000) = 520
Triclinic, P1	Dx = 2.344 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 3.9684 (10) Å	Cell parameters from 2619 reflections
b = 12.669 (3) Å	θ = 2.8–27.2°
c = 16.047 (4) Å	µ = 10.26 mm^−1
α = 79.68 (1)°	T = 174 K
β = 83.71 (1)°	Plate, colorless
γ = 83.06 (1)°	0.40 × 0.20 × 0.08 mm
V = 784.7 (3) Å^3

Data collection

Siemens area detector diffractometer	3510 independent reflections
Radiation source: fine-focus sealed tube	2975 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
ω scans	θmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995'	h = −5→5
Tmin = 0.105, Tmax = 0.440	k = −16→16
8883 measured reflections	l = −20→20

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.066P)^2 + 0.42P] where P = (Fo^2 + 2Fc^2)/3
3510 reflections	(Δ/σ)max = 0.002
200 parameters	Δρmax = 1.74 e Å^−3
0 restraints	Δρmin = −1.61 e Å^−3

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

	x	y	z	Uiso*/Ueq
C11	−0.0095 (12)	0.9176 (4)	0.3529 (3)	0.0227 (10)
C12	−0.0705 (12)	0.9253 (4)	0.2676 (3)	0.0232 (10)
H12	−0.1906	0.9882	0.2386	0.028*
Br13	−0.04126 (13)	0.84563 (5)	0.11182 (3)	0.02951 (17)
C13	0.0476 (12)	0.8394 (4)	0.2264 (3)	0.0229 (10)
O14	0.3444 (9)	0.6603 (3)	0.2300 (2)	0.0320 (9)
H14	0.2966	0.6726	0.1792	0.048*
C14	0.2266 (11)	0.7469 (4)	0.2676 (3)	0.0228 (10)
Br15	0.51745 (13)	0.61547 (4)	0.41019 (3)	0.02696 (17)
C15	0.2814 (12)	0.7423 (4)	0.3526 (3)	0.0240 (11)
C16	0.1678 (12)	0.8260 (4)	0.3959 (3)	0.0220 (10)
H16	0.2092	0.8214	0.4537	0.026*
N17	−0.2474 (12)	1.0800 (4)	0.4266 (3)	0.0336 (11)
C17	−0.1384 (12)	1.0078 (4)	0.3959 (3)	0.0254 (11)
C21	0.8384 (11)	0.4237 (4)	0.1469 (3)	0.0208 (10)
C22	0.8960 (12)	0.4265 (4)	0.2305 (3)	0.0227 (10)
H22	0.8098	0.4868	0.2571	0.027*
Br23	1.17513 (13)	0.33922 (4)	0.38743 (3)	0.02710 (17)
C23	1.0847 (12)	0.3378 (4)	0.2736 (3)	0.0217 (10)
O24	1.4033 (9)	0.1624 (3)	0.2758 (2)	0.0287 (8)
H24	1.4262	0.1708	0.3255	0.034*
C24	1.2159 (11)	0.2491 (4)	0.2365 (3)	0.0209 (10)
Br25	1.33538 (13)	0.13119 (4)	0.09937 (3)	0.02804 (17)
C25	1.1513 (11)	0.2491 (4)	0.1521 (3)	0.0207 (10)
C26	0.9636 (11)	0.3361 (4)	0.1071 (3)	0.0210 (10)
H26	0.9212	0.3358	0.0500	0.025*
N27	0.5009 (11)	0.5912 (4)	0.0657 (3)	0.0327 (11)
C27	0.6505 (12)	0.5170 (4)	0.1000 (3)	0.0243 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.027 (2)	0.022 (3)	0.020 (2)	−0.001 (2)	−0.0030 (18)	−0.0080 (19)
C12	0.026 (2)	0.024 (3)	0.020 (2)	0.000 (2)	−0.0070 (18)	−0.0025 (19)
Br13	0.0399 (3)	0.0331 (3)	0.0167 (3)	0.0045 (2)	−0.0087 (2)	−0.0093 (2)
C13	0.029 (2)	0.023 (3)	0.019 (2)	−0.004 (2)	−0.0043 (18)	−0.0070 (19)
O14	0.047 (2)	0.027 (2)	0.0227 (19)	0.0064 (17)	−0.0078 (16)	−0.0115 (16)
C14	0.028 (3)	0.020 (3)	0.022 (3)	0.000 (2)	−0.0007 (19)	−0.010 (2)
Br15	0.0355 (3)	0.0207 (3)	0.0235 (3)	0.0042 (2)	−0.0071 (2)	−0.0029 (2)
C15	0.025 (2)	0.024 (3)	0.022 (2)	−0.004 (2)	−0.0064 (18)	0.002 (2)
C16	0.029 (2)	0.022 (3)	0.017 (2)	−0.002 (2)	−0.0032 (18)	−0.0076 (19)
N17	0.049 (3)	0.027 (3)	0.026 (2)	0.009 (2)	−0.013 (2)	−0.009 (2)
C17	0.034 (3)	0.022 (3)	0.022 (3)	0.003 (2)	−0.012 (2)	−0.006 (2)
C21	0.021 (2)	0.021 (3)	0.021 (2)	−0.0004 (19)	−0.0036 (17)	−0.0052 (19)
C22	0.028 (2)	0.021 (3)	0.020 (2)	0.000 (2)	−0.0002 (18)	−0.0093 (19)
Br23	0.0360 (3)	0.0303 (3)	0.0166 (3)	−0.0001 (2)	−0.00651 (19)	−0.0078 (2)
C23	0.024 (2)	0.029 (3)	0.013 (2)	−0.007 (2)	−0.0007 (17)	−0.0036 (19)
O24	0.039 (2)	0.026 (2)	0.0206 (18)	0.0079 (16)	−0.0116 (15)	−0.0072 (15)
C24	0.022 (2)	0.022 (3)	0.020 (2)	−0.0031 (19)	−0.0022 (17)	−0.0031 (19)
Br25	0.0358 (3)	0.0261 (3)	0.0231 (3)	0.0066 (2)	−0.0054 (2)	−0.0114 (2)
C25	0.025 (2)	0.024 (3)	0.015 (2)	−0.003 (2)	−0.0007 (17)	−0.0075 (19)
C26	0.022 (2)	0.028 (3)	0.013 (2)	−0.001 (2)	−0.0043 (17)	−0.0043 (19)
N27	0.042 (3)	0.031 (3)	0.024 (2)	0.006 (2)	−0.0052 (19)	−0.008 (2)
C27	0.033 (3)	0.025 (3)	0.015 (2)	0.000 (2)	−0.003 (2)	−0.004 (2)

Geometric parameters (Å, º)

C11—C16	1.394 (7)	C21—C22	1.394 (7)
C11—C12	1.401 (7)	C21—C26	1.392 (7)
C11—C17	1.452 (7)	C21—C27	1.453 (6)
C12—C13	1.381 (7)	C22—C23	1.391 (7)
C12—H12	0.9500	C22—H22	0.9500
Br13—C13	1.895 (5)	Br23—C23	1.903 (5)
C13—C14	1.392 (7)	C23—C24	1.385 (7)
O14—C14	1.355 (6)	O24—C24	1.347 (5)
O14—H14	0.8400	O24—H24	0.8400
C14—C15	1.395 (7)	C24—C25	1.406 (6)
Br15—C15	1.899 (5)	Br25—C25	1.880 (5)
C15—C16	1.375 (7)	C25—C26	1.387 (6)
C16—H16	0.9500	C26—H26	0.9500
N17—C17	1.133 (7)	N27—C27	1.136 (6)
C16—C11—C12	121.3 (5)	C22—C21—C26	121.9 (4)
C16—C11—C17	120.5 (4)	C22—C21—C27	118.2 (5)
C12—C11—C17	118.2 (4)	C26—C21—C27	119.9 (4)
C13—C12—C11	118.6 (5)	C23—C22—C21	117.4 (5)
C13—C12—H12	120.7	C23—C22—H22	121.3
C11—C12—H12	120.7	C21—C22—H22	121.3
C12—C13—C14	121.4 (5)	C24—C23—C22	122.6 (4)
C12—C13—Br13	119.6 (4)	C24—C23—Br23	118.5 (4)
C14—C13—Br13	118.9 (4)	C22—C23—Br23	118.8 (4)
C14—O14—H14	109.5	C24—O24—H24	109.5
O14—C14—C13	123.5 (4)	O24—C24—C23	124.4 (4)
O14—C14—C15	118.3 (4)	O24—C24—C25	117.4 (4)
C13—C14—C15	118.2 (5)	C23—C24—C25	118.2 (4)
C16—C15—C14	122.2 (5)	C26—C25—C24	120.7 (4)
C16—C15—Br15	119.2 (4)	C26—C25—Br25	120.2 (4)
C14—C15—Br15	118.6 (4)	C24—C25—Br25	119.1 (4)
C15—C16—C11	118.3 (4)	C25—C26—C21	119.1 (4)
C15—C16—H16	120.9	C25—C26—H26	120.5
C11—C16—H16	120.9	C21—C26—H26	120.5
N17—C17—C11	176.9 (5)	N27—C27—C21	177.8 (5)

(MI-A) 3,5-diiodo-4-hydroxybenzonitrile / polymorph A

Crystal data

C7H3I2NO	Z = 4
Mr = 370.90	F(000) = 664
Triclinic, P1	Dx = 2.846 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.648 (2) Å	Cell parameters from 2025 reflections
b = 9.393 (2) Å	θ = 2.6–27.5°
c = 12.120 (2) Å	µ = 7.21 mm^−1
α = 97.32 (1)°	T = 174 K
β = 109.86 (1)°	Prism, colorless
γ = 105.59 (1)°	0.30 × 0.25 × 0.20 mm
V = 865.5 (3) Å^3

Data collection

Siemens area detector diffractometer	3930 independent reflections
Radiation source: fine-focus sealed tube	3102 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
ω scans	θmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995'	h = −11→11
Tmin = 0.121, Tmax = 0.237	k = −12→12
10284 measured reflections	l = −15→15

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.099	H-atom parameters constrained
S = 1.14	w = 1/[σ^2(Fo^2) + (0.031P)^2 + 5.03P] where P = (Fo^2 + 2Fc^2)/3
3930 reflections	(Δ/σ)max = 0.001
334 parameters	Δρmax = 1.08 e Å^−3
220 restraints	Δρmin = −1.24 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C11	0.3419 (5)	0.5807 (7)	0.7810 (6)	0.0190 (16)	0.9568 (18)
C12	0.2741 (4)	0.6649 (7)	0.7047 (6)	0.0198 (17)	0.9568 (18)
H12	0.2521	0.7513	0.7374	0.024*	0.9568 (18)
I13	0.13338 (8)	0.75915 (8)	0.46927 (6)	0.02092 (18)	0.9568 (18)
C13	0.2370 (8)	0.6287 (8)	0.5834 (7)	0.0159 (15)	0.9568 (18)
O14	0.2305 (7)	0.4560 (6)	0.4128 (5)	0.0261 (14)	0.9568 (18)
H14	0.1858	0.5141	0.3760	0.031*	0.9568 (18)
C14	0.2692 (9)	0.5027 (8)	0.5347 (7)	0.0176 (16)	0.9568 (18)
I15	0.38083 (8)	0.22502 (7)	0.53200 (6)	0.02361 (18)	0.9568 (18)
C15	0.3394 (9)	0.4168 (8)	0.6092 (7)	0.0177 (16)	0.9568 (18)
C16	0.3783 (9)	0.4552 (8)	0.7340 (7)	0.0205 (17)	0.9568 (18)
H16	0.4282	0.3971	0.7854	0.025*	0.9568 (18)
N17	0.4085 (10)	0.6505 (9)	1.0075 (7)	0.030 (2)	0.9568 (18)
C17	0.3802 (9)	0.6188 (9)	0.9083 (8)	0.0235 (18)	0.9568 (18)
C21	0.1590 (9)	0.2865 (8)	0.0842 (7)	0.0183 (16)	0.9568 (18)
C22	0.2294 (9)	0.2059 (8)	0.1664 (7)	0.0196 (17)	0.9568 (18)
H22	0.2508	0.2366	0.2495	0.024*	0.9568 (18)
I23	0.37373 (8)	−0.04516 (8)	0.24151 (6)	0.0246 (2)	0.9568 (18)
C23	0.2675 (9)	0.0802 (8)	0.1243 (7)	0.0182 (16)	0.9568 (18)
O24	0.2713 (7)	−0.0887 (6)	−0.0453 (5)	0.0290 (14)	0.9568 (18)
H24	0.3140	−0.1288	0.0105	0.035*	0.9568 (18)
C24	0.2351 (9)	0.0348 (8)	0.0013 (7)	0.0185 (16)	0.9568 (18)
I25	0.11671 (9)	0.04370 (8)	−0.26068 (5)	0.02799 (19)	0.9568 (18)
C25	0.1650 (9)	0.1154 (8)	−0.0784 (6)	0.0169 (15)	0.9568 (18)
C26	0.1262 (9)	0.2417 (9)	−0.0361 (7)	0.0225 (18)	0.9568 (18)
H26	0.0770	0.2966	−0.0909	0.027*	0.9568 (18)
N27	0.0879 (11)	0.5155 (9)	0.1669 (8)	0.040 (3)	0.9568 (18)
C27	0.1213 (10)	0.4167 (10)	0.1291 (8)	0.030 (2)	0.9568 (18)
C11A	0.342 (2)	0.882 (3)	1.0711 (18)	0.019*	0.0207 (10)
C12A	0.274 (2)	0.969 (2)	0.997 (2)	0.019*	0.0207 (10)
H12A	0.2537	1.0549	1.0318	0.023*	0.0207 (10)
I13A	0.1340 (19)	1.070 (2)	0.765 (3)	0.021*	0.0207 (10)
C13A	0.2356 (18)	0.935 (2)	0.876 (2)	0.017*	0.0207 (10)
O14A	0.2300 (19)	0.769 (2)	0.7022 (17)	0.026*	0.0207 (10)
H14A	0.1855	0.8278	0.6669	0.031*	0.0207 (10)
C14A	0.2655 (18)	0.810 (2)	0.8240 (18)	0.017*	0.0207 (10)
I15A	0.3762 (17)	0.532 (2)	0.815 (2)	0.024*	0.0207 (10)
C15A	0.3336 (19)	0.721 (2)	0.8959 (18)	0.018*	0.0207 (10)
C16A	0.373 (2)	0.755 (3)	1.0209 (18)	0.020*	0.0207 (10)
H16A	0.4198	0.6940	1.0702	0.024*	0.0207 (10)
N17A	0.411 (3)	0.951 (6)	1.298 (2)	0.031*	0.0207 (10)
C17A	0.383 (2)	0.918 (3)	1.1988 (19)	0.022*	0.0207 (10)
C21A	0.1703 (19)	0.578 (2)	0.381 (2)	0.020*	0.0207 (10)
C22A	0.239 (2)	0.499 (3)	0.464 (2)	0.020*	0.0207 (10)
H22A	0.2615	0.5320	0.5474	0.024*	0.0207 (10)
I23A	0.3789 (19)	0.247 (3)	0.543 (2)	0.025*	0.0207 (10)
C23A	0.2749 (19)	0.371 (3)	0.4240 (19)	0.018*	0.0207 (10)
O24A	0.2750 (19)	0.196 (2)	0.256 (2)	0.029*	0.0207 (10)
H24A	0.3174	0.1573	0.3127	0.035*	0.0207 (10)
C24A	0.2420 (18)	0.323 (2)	0.3012 (19)	0.019*	0.0207 (10)
I25A	0.1245 (19)	0.326 (3)	0.0381 (18)	0.028*	0.0207 (10)
C25A	0.1738 (18)	0.402 (2)	0.2201 (19)	0.017*	0.0207 (10)
C26A	0.1380 (19)	0.531 (2)	0.261 (2)	0.023*	0.0207 (10)
H26A	0.0912	0.5864	0.2052	0.028*	0.0207 (10)
N27A	0.109 (3)	0.813 (3)	0.465 (5)	0.040*	0.0207 (10)
C27A	0.134 (2)	0.711 (3)	0.424 (3)	0.029*	0.0207 (10)
C11B	0.333 (2)	0.322 (4)	0.511 (2)	0.019*	0.0225 (12)
C12B	0.265 (2)	0.404 (3)	0.433 (2)	0.019*	0.0225 (12)
H12B	0.2427	0.4910	0.4647	0.023*	0.0225 (12)
I13B	0.1246 (19)	0.493 (3)	0.196 (3)	0.021*	0.0225 (12)
C13B	0.229 (2)	0.366 (3)	0.312 (2)	0.017*	0.0225 (12)
O14B	0.228 (2)	0.192 (3)	0.145 (2)	0.026*	0.0225 (12)
H14B	0.1834	0.2497	0.1066	0.031*	0.0225 (12)
C14B	0.261 (2)	0.239 (3)	0.266 (2)	0.017*	0.0225 (12)
I15B	0.376 (2)	−0.037 (3)	0.268 (4)	0.024*	0.0225 (12)
C15B	0.330 (2)	0.153 (3)	0.342 (3)	0.018*	0.0225 (12)
C16B	0.367 (2)	0.194 (3)	0.466 (3)	0.020*	0.0225 (12)
H16B	0.4135	0.1351	0.5182	0.024*	0.0225 (12)
N17B	0.398 (3)	0.400 (7)	0.737 (2)	0.031*	0.0225 (12)
C17B	0.371 (2)	0.362 (4)	0.639 (2)	0.022*	0.0225 (12)
C21B	0.164 (2)	0.016 (3)	−0.173 (4)	0.020*	0.0225 (12)
C22B	0.233 (2)	−0.066 (3)	−0.092 (3)	0.020*	0.0225 (12)
H22B	0.2567	−0.0354	−0.0088	0.024*	0.0225 (12)
I23B	0.369 (2)	−0.323 (3)	−0.020 (3)	0.025*	0.0225 (12)
C23B	0.267 (2)	−0.194 (3)	−0.136 (3)	0.018*	0.0225 (12)
O24B	0.264 (2)	−0.365 (3)	−0.307 (3)	0.029*	0.0225 (12)
H24B	0.3068	−0.4055	−0.2518	0.035*	0.0225 (12)
C24B	0.233 (2)	−0.239 (3)	−0.259 (3)	0.019*	0.0225 (12)
I25B	0.116 (3)	−0.227 (5)	−0.520 (3)	0.028*	0.0225 (12)
C25B	0.165 (2)	−0.157 (4)	−0.338 (3)	0.017*	0.0225 (12)
C26B	0.131 (2)	−0.028 (4)	−0.294 (4)	0.023*	0.0225 (12)
H26B	0.0838	0.0287	−0.3479	0.028*	0.0225 (12)
N27B	0.106 (3)	0.249 (3)	−0.084 (6)	0.040*	0.0225 (12)
C27B	0.130 (3)	0.147 (3)	−0.127 (5)	0.029*	0.0225 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.018 (4)	0.025 (4)	0.019 (4)	0.011 (4)	0.009 (3)	0.009 (3)
C12	0.022 (4)	0.008 (4)	0.022 (4)	0.000 (3)	0.005 (3)	−0.004 (3)
I13	0.0259 (3)	0.0207 (3)	0.0210 (3)	0.0133 (3)	0.0092 (2)	0.0094 (2)
C13	0.020 (4)	0.016 (4)	0.019 (4)	0.011 (3)	0.010 (3)	0.011 (3)
O14	0.046 (4)	0.026 (3)	0.016 (3)	0.024 (3)	0.013 (3)	0.010 (2)
C14	0.020 (4)	0.021 (4)	0.014 (3)	0.006 (3)	0.008 (3)	0.008 (3)
I15	0.0331 (3)	0.0213 (3)	0.0221 (3)	0.0168 (3)	0.0113 (2)	0.0062 (2)
C15	0.021 (4)	0.015 (4)	0.022 (4)	0.008 (3)	0.012 (3)	0.008 (3)
C16	0.016 (4)	0.014 (4)	0.028 (4)	0.006 (3)	0.003 (3)	0.006 (3)
N17	0.047 (5)	0.032 (5)	0.018 (4)	0.024 (4)	0.013 (4)	0.005 (3)
C17	0.025 (4)	0.017 (4)	0.031 (5)	0.013 (4)	0.007 (4)	0.010 (4)
C21	0.024 (4)	0.013 (4)	0.015 (4)	0.007 (3)	0.005 (3)	−0.001 (3)
C22	0.019 (4)	0.021 (4)	0.022 (4)	0.009 (4)	0.010 (3)	0.007 (3)
I23	0.0337 (3)	0.0256 (3)	0.0193 (4)	0.0179 (3)	0.0084 (3)	0.0094 (3)
C23	0.022 (4)	0.019 (4)	0.019 (4)	0.011 (4)	0.010 (3)	0.006 (3)
O24	0.047 (4)	0.031 (3)	0.023 (3)	0.032 (3)	0.015 (3)	0.010 (3)
C24	0.017 (4)	0.017 (4)	0.023 (4)	0.008 (3)	0.007 (3)	0.011 (3)
I25	0.0399 (4)	0.0342 (4)	0.0184 (3)	0.0229 (3)	0.0124 (3)	0.0095 (3)
C25	0.014 (4)	0.015 (4)	0.016 (4)	0.000 (3)	0.002 (3)	0.004 (3)
C26	0.021 (4)	0.026 (4)	0.024 (4)	0.011 (4)	0.006 (3)	0.016 (4)
N27	0.073 (7)	0.041 (5)	0.021 (5)	0.042 (5)	0.017 (4)	0.014 (4)
C27	0.039 (5)	0.040 (5)	0.021 (4)	0.022 (5)	0.011 (4)	0.021 (4)

Geometric parameters (Å, º)

C11—C12	1.375 (10)	C21A—C26A	1.372 (11)
C11—C16	1.401 (10)	C21A—C22A	1.401 (11)
C11—C17	1.437 (11)	C21A—C27A	1.437 (12)
C12—C13	1.369 (10)	C22A—C23A	1.390 (10)
C12—H12	0.9500	C22A—H22A	0.9500
I13—C13	2.097 (7)	I23A—C23A	2.090 (7)
C13—C14	1.392 (10)	C23A—C24A	1.404 (10)
O14—C14	1.380 (8)	O24A—C24A	1.383 (9)
O14—H14	0.8400	O24A—H24A	0.8400
C14—C15	1.383 (10)	C24A—C25A	1.382 (10)
I15—C15	2.096 (7)	I25A—C25A	2.087 (7)
C15—C16	1.408 (11)	C25A—C26A	1.399 (11)
C16—H16	0.9500	C26A—H26A	0.9500
N17—C17	1.125 (11)	N27A—C27A	1.131 (12)
C21—C26	1.372 (11)	C11B—C12B	1.375 (10)
C21—C22	1.401 (11)	C11B—C16B	1.401 (10)
C21—C27	1.437 (12)	C11B—C17B	1.438 (11)
C22—C23	1.390 (10)	C12B—C13B	1.369 (10)
C22—H22	0.9500	C12B—H12B	0.9500
I23—C23	2.090 (7)	I13B—C13B	2.097 (7)
C23—C24	1.404 (10)	C13B—C14B	1.392 (10)
O24—C24	1.383 (9)	O14B—C14B	1.380 (9)
O24—H24	0.8400	O14B—H14B	0.8400
C24—C25	1.382 (10)	C14B—C15B	1.383 (10)
I25—C25	2.087 (7)	I15B—C15B	2.096 (7)
C25—C26	1.399 (11)	C15B—C16B	1.408 (11)
C26—H26	0.9500	C16B—H16B	0.9500
N27—C27	1.131 (12)	N17B—C17B	1.125 (11)
C11A—C12A	1.375 (10)	C21B—C26B	1.372 (11)
C11A—C16A	1.401 (10)	C21B—C22B	1.401 (11)
C11A—C17A	1.438 (11)	C21B—C27B	1.437 (12)
C12A—C13A	1.369 (10)	C22B—C23B	1.390 (10)
C12A—H12A	0.9500	C22B—H22B	0.9500
I13A—C13A	2.097 (7)	I23B—C23B	2.090 (7)
C13A—C14A	1.392 (10)	C23B—C24B	1.404 (10)
O14A—C14A	1.380 (9)	O24B—C24B	1.383 (9)
O14A—H14A	0.8400	O24B—H24B	0.8400
C14A—C15A	1.383 (10)	C24B—C25B	1.382 (10)
I15A—C15A	2.096 (7)	I25B—C25B	2.086 (7)
C15A—C16A	1.408 (11)	C25B—C26B	1.399 (11)
C16A—H16A	0.9500	C26B—H26B	0.9500
N17A—C17A	1.125 (11)	N27B—C27B	1.131 (12)
C12—C11—C16	119.2 (7)	C26A—C21A—C22A	120.8 (7)
C12—C11—C17	122.2 (6)	C26A—C21A—C27A	120.9 (8)
C16—C11—C17	118.6 (7)	C22A—C21A—C27A	118.3 (7)
C13—C12—C11	122.3 (6)	C23A—C22A—C21A	118.9 (7)
C13—C12—H12	118.8	C23A—C22A—H22A	120.5
C11—C12—H12	118.8	C21A—C22A—H22A	120.5
C12—C13—C14	119.3 (6)	C22A—C23A—C24A	120.3 (7)
C12—C13—I13	121.5 (5)	C22A—C23A—I23A	121.1 (5)
C14—C13—I13	119.2 (5)	C24A—C23A—I23A	118.6 (5)
C14—O14—H14	109.5	C24A—O24A—H24A	109.5
O14—C14—C15	117.4 (6)	C25A—C24A—O24A	117.3 (7)
O14—C14—C13	122.8 (6)	C25A—C24A—C23A	119.9 (7)
C15—C14—C13	119.8 (7)	O24A—C24A—C23A	122.8 (6)
C14—C15—C16	120.7 (7)	C24A—C25A—C26A	119.8 (7)
C14—C15—I15	118.7 (5)	C24A—C25A—I25A	118.8 (5)
C16—C15—I15	120.6 (5)	C26A—C25A—I25A	121.4 (5)
C11—C16—C15	118.7 (7)	C21A—C26A—C25A	120.3 (7)
C11—C16—H16	120.6	C21A—C26A—H26A	119.9
C15—C16—H16	120.6	C25A—C26A—H26A	119.9
N17—C17—C11	178.7 (8)	N27A—C27A—C21A	176 (2)
C26—C21—C22	120.8 (7)	C12B—C11B—C16B	119.2 (7)
C26—C21—C27	120.9 (7)	C12B—C11B—C17B	122.2 (7)
C22—C21—C27	118.3 (7)	C16B—C11B—C17B	118.6 (7)
C23—C22—C21	118.9 (7)	C13B—C12B—C11B	122.3 (6)
C23—C22—H22	120.5	C13B—C12B—H12B	118.8
C21—C22—H22	120.5	C11B—C12B—H12B	118.8
C22—C23—C24	120.3 (7)	C12B—C13B—C14B	119.3 (6)
C22—C23—I23	121.1 (5)	C12B—C13B—I13B	121.5 (5)
C24—C23—I23	118.6 (5)	C14B—C13B—I13B	119.2 (5)
C24—O24—H24	109.5	C14B—O14B—H14B	109.5
C25—C24—O24	117.3 (7)	O14B—C14B—C15B	117.4 (6)
C25—C24—C23	119.9 (7)	O14B—C14B—C13B	122.8 (6)
O24—C24—C23	122.8 (6)	C15B—C14B—C13B	119.8 (7)
C24—C25—C26	119.8 (7)	C14B—C15B—C16B	120.7 (7)
C24—C25—I25	118.8 (5)	C14B—C15B—I15B	118.7 (5)
C26—C25—I25	121.4 (5)	C16B—C15B—I15B	120.7 (5)
C21—C26—C25	120.3 (7)	C11B—C16B—C15B	118.7 (7)
C21—C26—H26	119.9	C11B—C16B—H16B	120.6
C25—C26—H26	119.9	C15B—C16B—H16B	120.6
N27—C27—C21	177.1 (9)	N17B—C17B—C11B	177 (3)
C12A—C11A—C16A	119.2 (7)	C26B—C21B—C22B	120.8 (7)
C12A—C11A—C17A	122.2 (7)	C26B—C21B—C27B	120.9 (8)
C16A—C11A—C17A	118.6 (7)	C22B—C21B—C27B	118.3 (7)
C13A—C12A—C11A	122.3 (6)	C23B—C22B—C21B	118.9 (7)
C13A—C12A—H12A	118.8	C23B—C22B—H22B	120.5
C11A—C12A—H12A	118.8	C21B—C22B—H22B	120.5
C12A—C13A—C14A	119.3 (6)	C22B—C23B—C24B	120.3 (7)
C12A—C13A—I13A	121.5 (5)	C22B—C23B—I23B	121.1 (5)
C14A—C13A—I13A	119.2 (5)	C24B—C23B—I23B	118.6 (5)
C14A—O14A—H14A	109.5	C24B—O24B—H24B	109.5
O14A—C14A—C15A	117.4 (6)	C25B—C24B—O24B	117.3 (7)
O14A—C14A—C13A	122.8 (6)	C25B—C24B—C23B	119.9 (7)
C15A—C14A—C13A	119.8 (7)	O24B—C24B—C23B	122.8 (6)
C14A—C15A—C16A	120.7 (7)	C24B—C25B—C26B	119.8 (7)
C14A—C15A—I15A	118.7 (5)	C24B—C25B—I25B	118.8 (5)
C16A—C15A—I15A	120.7 (5)	C26B—C25B—I25B	121.4 (5)
C11A—C16A—C15A	118.7 (7)	C21B—C26B—C25B	120.3 (7)
C11A—C16A—H16A	120.6	C21B—C26B—H26B	119.9
C15A—C16A—H16A	120.6	C25B—C26B—H26B	119.9
N17A—C17A—C11A	177 (2)	N27B—C27B—C21B	176 (2)

(MI-C) 3,5-diiodo-4-hydroxybenzonitrile / polymorph C

Crystal data

C7H3I2NO	F(000) = 1328
Mr = 370.90	Dx = 2.841 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3574 reflections
a = 15.657 (4) Å	θ = 2.6–27.5°
b = 14.320 (4) Å	µ = 7.21 mm^−1
c = 7.724 (2) Å	T = 173 K
β = 91.90 (1)°	Needle, colorless
V = 1730.8 (8) Å^3	0.50 × 0.10 × 0.07 mm
Z = 8

Data collection

Siemens area detector diffractometer	3931 independent reflections
Radiation source: fine-focus sealed tube	3587 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
ω scans	θmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan SADABS; Sheldrick, 1996; Blessing, 1995'	h = −20→20
Tmin = 0.47, Tmax = 0.60	k = −17→18
16090 measured reflections	l = −10→10

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)] = 0.020	H-atom parameters constrained
wR(F^2) = 0.046	w = 1/[σ^2(Fo^2) + (0.014P)^2 + 1.59P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.006
3936 reflections	Δρmax = 0.60 e Å^−3
200 parameters	Δρmin = −0.54 e Å^−3
0 restraints	Extinction correction: SHELXTL
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00378 (9)

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

	x	y	z	Uiso*/Ueq
I13	0.646356 (10)	0.465381 (13)	0.63572 (2)	0.02125 (6)
I15	0.349835 (11)	0.687241 (12)	0.88878 (2)	0.02308 (6)
O14	0.52408 (12)	0.63736 (13)	0.7359 (2)	0.0248 (4)
H14	0.5761	0.6281	0.7184	0.030*
N17	0.32264 (16)	0.23472 (18)	0.9129 (4)	0.0354 (6)
C11	0.39844 (16)	0.38959 (18)	0.8398 (3)	0.0189 (5)
C12	0.47917 (15)	0.38600 (19)	0.7684 (3)	0.0189 (5)
H12	0.5043	0.3274	0.7429	0.023*
C13	0.52267 (15)	0.46812 (18)	0.7347 (3)	0.0174 (5)
C14	0.48550 (16)	0.55495 (18)	0.7689 (3)	0.0179 (5)
C15	0.40463 (15)	0.55699 (17)	0.8405 (3)	0.0167 (5)
C16	0.36027 (15)	0.47558 (19)	0.8771 (3)	0.0181 (5)
H16	0.3055	0.4781	0.9261	0.022*
C17	0.35481 (17)	0.3039 (2)	0.8807 (4)	0.0246 (6)
I23	1.138156 (11)	0.827849 (13)	0.60680 (2)	0.02323 (6)
I25	0.847294 (11)	1.048985 (13)	0.89008 (2)	0.02429 (6)
O24	1.01711 (12)	1.00074 (13)	0.7181 (3)	0.0262 (4)
H24	1.0643	0.9914	0.6725	0.039*
N27	0.82339 (16)	0.59508 (18)	0.9021 (3)	0.0319 (6)
C21	0.89493 (16)	0.75212 (18)	0.8299 (3)	0.0192 (5)
C22	0.97489 (16)	0.74859 (18)	0.7543 (3)	0.0199 (5)
H22	1.0002	0.6901	0.7285	0.024*
C23	1.01709 (16)	0.83144 (19)	0.7173 (3)	0.0189 (5)
C24	0.98030 (16)	0.91772 (18)	0.7545 (3)	0.0188 (5)
C25	0.90055 (16)	0.91920 (18)	0.8323 (3)	0.0186 (5)
C26	0.85755 (15)	0.83761 (19)	0.8708 (3)	0.0195 (5)
H26	0.8037	0.8397	0.9239	0.023*
C27	0.85282 (16)	0.6653 (2)	0.8709 (3)	0.0241 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I13	0.01725 (9)	0.02018 (10)	0.02665 (10)	0.00015 (6)	0.00579 (6)	0.00036 (7)
I15	0.02349 (10)	0.01406 (10)	0.03225 (11)	0.00244 (6)	0.00940 (7)	0.00079 (7)
O14	0.0221 (10)	0.0151 (10)	0.0380 (11)	−0.0018 (8)	0.0113 (8)	0.0012 (8)
N17	0.0341 (14)	0.0178 (13)	0.0556 (17)	−0.0033 (11)	0.0185 (12)	−0.0002 (12)
C11	0.0194 (12)	0.0147 (13)	0.0227 (12)	−0.0007 (10)	0.0012 (10)	−0.0006 (10)
C12	0.0190 (12)	0.0153 (13)	0.0226 (12)	0.0015 (10)	0.0017 (10)	−0.0005 (10)
C13	0.0132 (11)	0.0177 (13)	0.0214 (12)	0.0010 (10)	0.0034 (9)	0.0005 (10)
C14	0.0185 (12)	0.0162 (13)	0.0190 (12)	−0.0020 (10)	0.0008 (9)	0.0017 (10)
C15	0.0176 (12)	0.0130 (12)	0.0196 (12)	0.0035 (9)	0.0013 (9)	−0.0011 (10)
C16	0.0184 (12)	0.0169 (14)	0.0192 (12)	−0.0018 (10)	0.0042 (10)	0.0008 (10)
C17	0.0229 (14)	0.0179 (15)	0.0336 (16)	0.0017 (11)	0.0094 (12)	−0.0009 (11)
I23	0.01934 (10)	0.01976 (11)	0.03114 (11)	−0.00083 (7)	0.00923 (7)	−0.00137 (7)
I25	0.02248 (10)	0.01767 (11)	0.03318 (11)	0.00277 (7)	0.00763 (7)	0.00025 (7)
O24	0.0228 (10)	0.0170 (10)	0.0394 (11)	−0.0003 (8)	0.0110 (8)	0.0032 (8)
N27	0.0282 (13)	0.0182 (13)	0.0496 (15)	−0.0018 (10)	0.0029 (11)	−0.0017 (11)
C21	0.0188 (12)	0.0163 (13)	0.0226 (13)	−0.0023 (10)	0.0012 (9)	0.0031 (10)
C22	0.0212 (13)	0.0144 (13)	0.0241 (13)	−0.0017 (10)	0.0008 (10)	−0.0011 (10)
C23	0.0144 (12)	0.0211 (14)	0.0214 (12)	0.0005 (10)	0.0047 (9)	−0.0008 (10)
C24	0.0197 (12)	0.0155 (14)	0.0214 (12)	−0.0017 (10)	0.0021 (10)	0.0013 (10)
C25	0.0191 (12)	0.0168 (13)	0.0201 (12)	0.0030 (10)	0.0018 (9)	−0.0004 (10)
C26	0.0162 (12)	0.0183 (14)	0.0242 (13)	−0.0015 (10)	0.0033 (10)	0.0015 (10)
C27	0.0196 (14)	0.0246 (16)	0.0286 (15)	0.0021 (11)	0.0066 (11)	−0.0012 (11)

Geometric parameters (Å, º)

I13—C13	2.106 (2)	I23—C23	2.105 (2)
I15—C15	2.092 (2)	I25—C25	2.091 (3)
O14—C14	1.354 (3)	O24—C24	1.355 (3)
O14—H14	0.8400	O24—H24	0.8400
N17—C17	1.143 (4)	N27—C27	1.135 (4)
C11—C12	1.397 (3)	C21—C22	1.400 (3)
C11—C16	1.403 (4)	C21—C26	1.398 (4)
C11—C17	1.444 (4)	C21—C27	1.447 (4)
C12—C13	1.388 (4)	C22—C23	1.392 (4)
C12—H12	0.9500	C22—H22	0.9500
C13—C14	1.402 (4)	C23—C24	1.397 (4)
C14—C15	1.399 (3)	C24—C25	1.404 (3)
C15—C16	1.391 (3)	C25—C26	1.386 (4)
C16—H16	0.9500	C26—H26	0.9500
C14—O14—H14	109.5	C24—O24—H24	109.5
C12—C11—C16	120.7 (2)	C22—C21—C26	120.8 (2)
C12—C11—C17	119.7 (2)	C22—C21—C27	118.7 (2)
C16—C11—C17	119.5 (2)	C26—C21—C27	120.4 (2)
C13—C12—C11	119.9 (2)	C23—C22—C21	119.5 (2)
C13—C12—H12	120.0	C23—C22—H22	120.3
C11—C12—H12	120.0	C21—C22—H22	120.3
C12—C13—C14	120.5 (2)	C22—C23—C24	120.6 (2)
C12—C13—I13	121.01 (19)	C22—C23—I23	120.15 (19)
C14—C13—I13	118.53 (18)	C24—C23—I23	119.21 (19)
O14—C14—C15	118.1 (2)	O24—C24—C23	123.5 (2)
O14—C14—C13	123.2 (2)	O24—C24—C25	117.8 (2)
C15—C14—C13	118.7 (2)	C23—C24—C25	118.7 (2)
C16—C15—C14	121.8 (2)	C26—C25—C24	121.6 (2)
C16—C15—I15	120.04 (18)	C26—C25—I25	120.25 (18)
C14—C15—I15	118.11 (18)	C24—C25—I25	118.12 (19)
C15—C16—C11	118.4 (2)	C25—C26—C21	118.7 (2)
C15—C16—H16	120.8	C25—C26—H26	120.6
C11—C16—H16	120.8	C21—C26—H26	120.6
N17—C17—C11	177.9 (3)	N27—C27—C21	176.7 (3)