C—I...N and C—I...π halogen bonding in the structures of 1-benzyl­iodo­imidazole derivatives

Halogen bonding is a well-established and intensively studied inter­molecular inter­action that has also been used in the preparation of functional materials. While polyfluoro­iodo- and polyfluoro­bromo­benzenes have been widely used as aromatic halogen-bond donors, there have been very few studies of iodo­imidazoles with regard to halogen bonding. We describe here the X-ray structures of three iodo­imidazole derivatives, namely 1-benzyl-2-iodo-1H-imidazole, C₁₀H₉IN₂, (1), 1-benzyl-4-iodo-1H-imidazole, C₁₀H₉IN₂, (2), and 1-benzyl-2-iodo-1H-benz­imidazole, C₁₄H₁₁IN₂, (3), and the halogen bonds that dominate the inter­molecular inter­actions in each of these three structures. The three-dimensional structure of (1) is dominated by a strong C—I...N halogen bond, with an N...I distance of 2.8765 (2) Å, that connects the mol­ecules into one-dimensional zigzag ribbons of mol­ecules. In contrast, the three-dimensional structures of (2) and (3) both feature C—I...π halogen-bonded dimers.

Computing details

For all structures, data collection: SMART (Bruker, 2014); cell refinement: SMART (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: X-SEED (Barbour, 2001).

1-Benzyl-2-iodo-1H-imidazole (1)

Crystal data

C10H9IN2	Dx = 1.858 Mg m^−3
Mr = 284.09	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 7864 reflections
a = 8.7561 (5) Å	θ = 2.8–27.1°
b = 9.0016 (5) Å	µ = 3.11 mm^−1
c = 12.8869 (7) Å	T = 100 K
V = 1015.73 (10) Å^3	Irregular, colourless
Z = 4	0.30 × 0.20 × 0.05 mm
F(000) = 544

Data collection

Bruker APEXII CCD diffractometer	2228 independent reflections
Radiation source: fine-focus sealed tube	2202 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Detector resolution: 8.3660 pixels mm^-1	θmax = 27.1°, θmin = 2.8°
phi and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −11→11
Tmin = 0.622, Tmax = 0.746	l = −16→16
13262 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.013	w = 1/[σ^2(Fo^2) + (0.0131P)^2 + 0.0966P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.030	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.25 e Å^−3
2228 reflections	Δρmin = −0.27 e Å^−3
118 parameters	Absolute structure: Flack x determined using 913 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: −0.002 (13)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
I1	0.23697 (2)	0.28234 (2)	0.52915 (2)	0.01308 (5)
N1	0.1137 (3)	0.4336 (3)	0.72457 (18)	0.0140 (5)
C1	0.0779 (3)	0.3510 (3)	0.6399 (2)	0.0126 (6)
N2	−0.0686 (3)	0.3169 (3)	0.63687 (19)	0.0153 (5)
C2	−0.1294 (3)	0.3814 (3)	0.7256 (2)	0.0175 (6)
H1	−0.2337	0.3759	0.7456	0.021*
C3	−0.0203 (3)	0.4526 (3)	0.7792 (2)	0.0173 (6)
H9	−0.0329	0.5057	0.8423	0.021*
C4	0.2632 (4)	0.4913 (3)	0.7544 (2)	0.0163 (6)
H7	0.2484	0.5859	0.7923	0.020*
H8	0.3218	0.5138	0.6906	0.020*
C5	0.3573 (3)	0.3881 (3)	0.8214 (2)	0.0145 (6)
C6	0.3217 (3)	0.2395 (3)	0.8364 (2)	0.0165 (6)
H3	0.2345	0.1980	0.8035	0.020*
C7	0.4136 (3)	0.1504 (4)	0.8995 (2)	0.0210 (7)
H4	0.3885	0.0487	0.9094	0.025*
C8	0.5407 (3)	0.2094 (4)	0.9477 (2)	0.0215 (7)
H2	0.6027	0.1487	0.9909	0.026*
C9	0.5776 (4)	0.3587 (4)	0.9327 (2)	0.0222 (7)
H5	0.6647	0.4001	0.9658	0.027*
C10	0.4869 (3)	0.4463 (3)	0.8693 (2)	0.0177 (6)
H6	0.5134	0.5474	0.8583	0.021*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01264 (8)	0.01415 (9)	0.01244 (8)	0.00140 (7)	0.00028 (7)	−0.00020 (6)
N1	0.0139 (12)	0.0132 (12)	0.0150 (12)	0.0009 (10)	−0.0017 (10)	−0.0015 (10)
C1	0.0138 (14)	0.0102 (13)	0.0138 (14)	0.0027 (11)	−0.0002 (11)	0.0008 (11)
N2	0.0134 (11)	0.0163 (14)	0.0161 (12)	0.0017 (9)	−0.0001 (9)	0.0000 (9)
C2	0.0153 (14)	0.0183 (16)	0.0189 (15)	0.0027 (12)	0.0024 (12)	−0.0005 (12)
C3	0.0206 (16)	0.0178 (15)	0.0135 (14)	0.0043 (13)	0.0023 (13)	−0.0010 (12)
C4	0.0169 (14)	0.0147 (13)	0.0172 (12)	−0.0036 (12)	−0.0032 (15)	−0.0006 (10)
C5	0.0142 (14)	0.0182 (15)	0.0110 (14)	0.0018 (12)	0.0021 (11)	−0.0028 (11)
C6	0.0148 (13)	0.0173 (16)	0.0174 (13)	−0.0015 (11)	−0.0003 (11)	−0.0018 (12)
C7	0.0222 (16)	0.0204 (15)	0.0203 (15)	0.0022 (13)	0.0067 (13)	0.0026 (13)
C8	0.0211 (14)	0.0277 (17)	0.0156 (14)	0.0087 (15)	−0.0008 (11)	0.0024 (14)
C9	0.0171 (15)	0.0285 (18)	0.0210 (16)	0.0039 (14)	−0.0034 (12)	−0.0039 (14)
C10	0.0169 (15)	0.0168 (15)	0.0195 (15)	−0.0010 (12)	0.0007 (13)	−0.0037 (13)

Geometric parameters (Å, º)

I1—C1	2.088 (3)	C5—C6	1.387 (4)
N1—C1	1.357 (4)	C5—C10	1.394 (4)
N1—C3	1.379 (3)	C6—C7	1.397 (4)
N1—C4	1.461 (4)	C6—H3	0.9500
C1—N2	1.319 (3)	C7—C8	1.381 (4)
N2—C2	1.389 (4)	C7—H4	0.9500
C2—C3	1.341 (4)	C8—C9	1.395 (5)
C2—H1	0.9500	C8—H2	0.9500
C3—H9	0.9500	C9—C10	1.386 (4)
C4—C5	1.512 (4)	C9—H5	0.9500
C4—H7	0.9900	C10—H6	0.9500
C4—H8	0.9900
C1—N1—C3	106.4 (2)	C6—C5—C10	118.9 (3)
C1—N1—C4	127.8 (2)	C6—C5—C4	123.4 (3)
C3—N1—C4	125.8 (2)	C10—C5—C4	117.7 (3)
N2—C1—N1	112.1 (2)	C5—C6—C7	120.4 (3)
N2—C1—I1	124.0 (2)	C5—C6—H3	119.8
N1—C1—I1	123.9 (2)	C7—C6—H3	119.8
C1—N2—C2	104.5 (2)	C8—C7—C6	120.3 (3)
C3—C2—N2	110.5 (3)	C8—C7—H4	119.8
C3—C2—H1	124.7	C6—C7—H4	119.8
N2—C2—H1	124.7	C7—C8—C9	119.7 (3)
C2—C3—N1	106.5 (3)	C7—C8—H2	120.2
C2—C3—H9	126.8	C9—C8—H2	120.2
N1—C3—H9	126.8	C10—C9—C8	119.8 (3)
N1—C4—C5	114.8 (2)	C10—C9—H5	120.1
N1—C4—H7	108.6	C8—C9—H5	120.1
C5—C4—H7	108.6	C9—C10—C5	120.9 (3)
N1—C4—H8	108.6	C9—C10—H6	119.5
C5—C4—H8	108.6	C5—C10—H6	119.5
H7—C4—H8	107.5
C3—N1—C1—N2	0.2 (3)	C3—N1—C4—C5	90.2 (3)
C4—N1—C1—N2	179.7 (2)	N1—C4—C5—C6	13.0 (4)
C3—N1—C1—I1	−178.7 (2)	N1—C4—C5—C10	−167.7 (2)
C4—N1—C1—I1	0.9 (4)	C10—C5—C6—C7	0.8 (4)
N1—C1—N2—C2	−0.3 (3)	C4—C5—C6—C7	−179.9 (3)
I1—C1—N2—C2	178.5 (2)	C5—C6—C7—C8	0.0 (4)
C1—N2—C2—C3	0.3 (3)	C6—C7—C8—C9	−0.3 (4)
N2—C2—C3—N1	−0.2 (3)	C7—C8—C9—C10	−0.2 (4)
C1—N1—C3—C2	0.1 (3)	C8—C9—C10—C5	1.1 (4)
C4—N1—C3—C2	−179.5 (3)	C6—C5—C10—C9	−1.4 (4)
C1—N1—C4—C5	−89.3 (3)	C4—C5—C10—C9	179.3 (3)

1-Benzyl-4-iodo-1H-benzimidazole (2)

Crystal data

C10H9IN2	F(000) = 544
Mr = 284.09	Dx = 1.878 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.4574 (5) Å	Cell parameters from 7481 reflections
b = 6.1526 (3) Å	θ = 2.5–27.1°
c = 19.4261 (10) Å	µ = 3.14 mm^−1
β = 96.362 (1)°	T = 100 K
V = 1004.61 (9) Å^3	Cut irregular cube, colourless
Z = 4	0.22 × 0.22 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer	2207 independent reflections
Radiation source: fine-focus sealed tube	2114 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 8.3660 pixels mm^-1	θmax = 27.1°, θmin = 2.1°
phi and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −7→7
Tmin = 0.594, Tmax = 0.746	l = −24→24
12374 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.016	H-atom parameters constrained
wR(F^2) = 0.037	w = 1/[σ^2(Fo^2) + (0.0133P)^2 + 0.8316P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max = 0.002
2207 reflections	Δρmax = 0.73 e Å^−3
118 parameters	Δρmin = −0.52 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
I1	0.78435 (2)	0.28882 (2)	0.99037 (2)	0.02415 (5)
N1	0.62017 (18)	0.7607 (3)	0.84311 (8)	0.0184 (3)
C1	0.6885 (2)	0.6133 (3)	0.80429 (9)	0.0193 (4)
H1	0.6911	0.6269	0.7557	0.023*
N2	0.75130 (18)	0.4480 (3)	0.84125 (8)	0.0202 (3)
C2	0.7195 (2)	0.4950 (3)	0.90773 (9)	0.0176 (4)
C3	0.6390 (2)	0.6861 (3)	0.91019 (9)	0.0202 (4)
H3	0.6035	0.7533	0.9497	0.024*
C4	0.5408 (2)	0.9614 (3)	0.81736 (10)	0.0234 (4)
H4A	0.5420	0.9692	0.7665	0.028*
H4B	0.6011	1.0876	0.8381	0.028*
C5	0.3709 (2)	0.9758 (3)	0.83403 (9)	0.0180 (4)
C6	0.2651 (2)	0.8056 (3)	0.81699 (10)	0.0212 (4)
H6	0.3005	0.6781	0.7958	0.025*
C7	0.1081 (2)	0.8218 (3)	0.83096 (10)	0.0256 (4)
H7	0.0365	0.7048	0.8197	0.031*
C8	0.0554 (2)	1.0088 (4)	0.86130 (10)	0.0265 (4)
H8	−0.0523	1.0201	0.8705	0.032*
C9	0.1594 (3)	1.1779 (3)	0.87815 (11)	0.0277 (4)
H9	0.1231	1.3058	0.8988	0.033*
C10	0.3176 (2)	1.1619 (3)	0.86495 (10)	0.0240 (4)
H10	0.3891	1.2783	0.8771	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.02821 (8)	0.02566 (8)	0.01895 (7)	0.00504 (5)	0.00421 (5)	0.00451 (5)
N1	0.0185 (8)	0.0183 (8)	0.0193 (8)	0.0004 (6)	0.0055 (6)	0.0031 (6)
C1	0.0177 (9)	0.0255 (10)	0.0152 (8)	0.0006 (7)	0.0038 (7)	−0.0016 (7)
N2	0.0198 (8)	0.0235 (8)	0.0177 (7)	0.0025 (6)	0.0045 (6)	−0.0027 (6)
C2	0.0171 (8)	0.0191 (9)	0.0167 (8)	0.0005 (7)	0.0027 (7)	0.0004 (7)
C3	0.0248 (10)	0.0203 (10)	0.0167 (9)	0.0003 (7)	0.0075 (7)	0.0000 (7)
C4	0.0248 (10)	0.0186 (9)	0.0281 (10)	0.0021 (8)	0.0089 (8)	0.0080 (8)
C5	0.0211 (9)	0.0178 (9)	0.0151 (8)	0.0028 (7)	0.0022 (7)	0.0043 (7)
C6	0.0259 (10)	0.0184 (9)	0.0190 (9)	0.0042 (7)	0.0009 (7)	−0.0028 (7)
C7	0.0212 (10)	0.0305 (12)	0.0236 (10)	−0.0015 (8)	−0.0045 (8)	−0.0048 (8)
C8	0.0195 (9)	0.0380 (12)	0.0216 (9)	0.0078 (8)	0.0004 (7)	−0.0019 (8)
C9	0.0314 (11)	0.0263 (11)	0.0257 (10)	0.0106 (9)	0.0050 (8)	−0.0037 (8)
C10	0.0279 (10)	0.0185 (10)	0.0254 (10)	0.0007 (8)	0.0015 (8)	−0.0010 (8)

Geometric parameters (Å, º)

I1—C2	2.0717 (18)	C5—C10	1.391 (3)
N1—C1	1.349 (2)	C5—C6	1.393 (3)
N1—C3	1.374 (2)	C6—C7	1.388 (3)
N1—C4	1.467 (2)	C6—H6	0.9500
C1—N2	1.322 (2)	C7—C8	1.388 (3)
C1—H1	0.9500	C7—H7	0.9500
N2—C2	1.379 (2)	C8—C9	1.378 (3)
C2—C3	1.362 (3)	C8—H8	0.9500
C3—H3	0.9500	C9—C10	1.394 (3)
C4—C5	1.510 (3)	C9—H9	0.9500
C4—H4A	0.9900	C10—H10	0.9500
C4—H4B	0.9900
C1—N1—C3	107.09 (15)	C10—C5—C6	119.40 (17)
C1—N1—C4	125.67 (16)	C10—C5—C4	120.18 (18)
C3—N1—C4	127.24 (16)	C6—C5—C4	120.39 (17)
N2—C1—N1	112.62 (16)	C7—C6—C5	120.18 (18)
N2—C1—H1	123.7	C7—C6—H6	119.9
N1—C1—H1	123.7	C5—C6—H6	119.9
C1—N2—C2	103.82 (15)	C8—C7—C6	120.08 (19)
C3—C2—N2	111.35 (16)	C8—C7—H7	120.0
C3—C2—I1	126.28 (13)	C6—C7—H7	120.0
N2—C2—I1	122.34 (13)	C9—C8—C7	120.02 (19)
C2—C3—N1	105.11 (16)	C9—C8—H8	120.0
C2—C3—H3	127.4	C7—C8—H8	120.0
N1—C3—H3	127.4	C8—C9—C10	120.24 (19)
N1—C4—C5	112.76 (15)	C8—C9—H9	119.9
N1—C4—H4A	109.0	C10—C9—H9	119.9
C5—C4—H4A	109.0	C5—C10—C9	120.08 (19)
N1—C4—H4B	109.0	C5—C10—H10	120.0
C5—C4—H4B	109.0	C9—C10—H10	120.0
H4A—C4—H4B	107.8
C3—N1—C1—N2	−0.3 (2)	N1—C4—C5—C10	129.69 (19)
C4—N1—C1—N2	179.94 (17)	N1—C4—C5—C6	−52.0 (2)
N1—C1—N2—C2	0.3 (2)	C10—C5—C6—C7	−0.2 (3)
C1—N2—C2—C3	−0.1 (2)	C4—C5—C6—C7	−178.49 (18)
C1—N2—C2—I1	178.38 (13)	C5—C6—C7—C8	0.7 (3)
N2—C2—C3—N1	0.0 (2)	C6—C7—C8—C9	−0.6 (3)
I1—C2—C3—N1	−178.47 (13)	C7—C8—C9—C10	−0.1 (3)
C1—N1—C3—C2	0.2 (2)	C6—C5—C10—C9	−0.5 (3)
C4—N1—C3—C2	179.96 (17)	C4—C5—C10—C9	177.82 (18)
C1—N1—C4—C5	123.20 (19)	C8—C9—C10—C5	0.7 (3)
C3—N1—C4—C5	−56.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···N2^i	0.99	2.55	3.488 (3)	158
C4—H4B···N2^i	0.99	2.55	3.488 (3)	158
C4—H4B···N2^i	0.99	2.55	3.488 (3)	158
C4—H4B···N2^i	0.99	2.55	3.488 (3)	158

Symmetry code: (i) x, y+1, z.

1-Benzyl-2-iodo-1H-benzimidazole (3)

Crystal data

C14H11IN2	Z = 2
Mr = 334.15	F(000) = 324
Triclinic, P1	Dx = 1.796 Mg m^−3
a = 6.4606 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.2346 (10) Å	Cell parameters from 6682 reflections
c = 12.3451 (14) Å	θ = 2.6–27.3°
α = 108.064 (1)°	µ = 2.57 mm^−1
β = 94.174 (2)°	T = 100 K
γ = 95.366 (2)°	Cut irregular cube, colourless
V = 618.05 (13) Å^3	0.20 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer	2777 independent reflections
Radiation source: fine-focus sealed tube	2725 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
Detector resolution: 8.3660 pixels mm^-1	θmax = 27.3°, θmin = 1.8°
phi and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −10→10
Tmin = 0.588, Tmax = 0.746	l = −15→15
8079 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.015	H-atom parameters constrained
wR(F^2) = 0.039	w = 1/[σ^2(Fo^2) + (0.0194P)^2 + 0.3329P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
2777 reflections	Δρmax = 0.74 e Å^−3
154 parameters	Δρmin = −0.35 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
I1	0.36505 (2)	0.21176 (2)	−0.00445 (2)	0.01647 (5)
N1	0.6779 (2)	0.27787 (17)	0.20512 (12)	0.0120 (3)
C1	0.4707 (3)	0.2345 (2)	0.16333 (14)	0.0128 (3)
N2	0.3471 (2)	0.20232 (18)	0.23569 (12)	0.0150 (3)
C2	0.4817 (3)	0.2263 (2)	0.33480 (14)	0.0139 (3)
C3	0.4394 (3)	0.2054 (2)	0.43956 (15)	0.0182 (3)
H3	0.3012	0.1724	0.4531	0.022*
C4	0.6071 (3)	0.2349 (2)	0.52297 (15)	0.0194 (4)
H4	0.5828	0.2201	0.5945	0.023*
C5	0.8118 (3)	0.2859 (2)	0.50456 (15)	0.0175 (3)
H5	0.9221	0.3057	0.5641	0.021*
C6	0.8566 (3)	0.3081 (2)	0.40127 (15)	0.0151 (3)
H6	0.9943	0.3438	0.3885	0.018*
C7	0.6875 (3)	0.2749 (2)	0.31748 (14)	0.0122 (3)
C8	0.8525 (3)	0.3389 (2)	0.15353 (14)	0.0132 (3)
H8B	0.8223	0.2938	0.0691	0.016*
H8A	0.9799	0.2929	0.1749	0.016*
C9	0.8940 (3)	0.5343 (2)	0.19092 (13)	0.0117 (3)
C10	1.0811 (3)	0.6095 (2)	0.16685 (15)	0.0158 (3)
H10	1.1789	0.5383	0.1290	0.019*
C11	1.1250 (3)	0.7877 (2)	0.19790 (15)	0.0177 (3)
H11	1.2523	0.8376	0.1811	0.021*
C12	0.9832 (3)	0.8928 (2)	0.25341 (15)	0.0160 (3)
H12	1.0129	1.0144	0.2742	0.019*
C13	0.7972 (3)	0.8192 (2)	0.27853 (14)	0.0150 (3)
H13	0.7006	0.8907	0.3173	0.018*
C14	0.7526 (3)	0.6401 (2)	0.24673 (14)	0.0136 (3)
H14	0.6250	0.5904	0.2633	0.016*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01853 (7)	0.01995 (7)	0.01172 (6)	0.00853 (4)	0.00073 (4)	0.00460 (4)
N1	0.0124 (6)	0.0118 (6)	0.0118 (6)	0.0009 (5)	0.0018 (5)	0.0038 (5)
C1	0.0145 (8)	0.0118 (7)	0.0120 (7)	0.0031 (6)	0.0003 (6)	0.0036 (6)
N2	0.0129 (7)	0.0168 (7)	0.0161 (7)	0.0012 (5)	0.0005 (5)	0.0069 (6)
C2	0.0138 (8)	0.0130 (7)	0.0157 (8)	0.0018 (6)	0.0016 (6)	0.0058 (6)
C3	0.0155 (8)	0.0236 (9)	0.0182 (8)	0.0018 (7)	0.0050 (7)	0.0099 (7)
C4	0.0229 (9)	0.0238 (9)	0.0144 (8)	0.0035 (7)	0.0036 (7)	0.0098 (7)
C5	0.0193 (9)	0.0179 (8)	0.0144 (8)	0.0025 (7)	−0.0026 (7)	0.0048 (6)
C6	0.0133 (8)	0.0136 (7)	0.0170 (8)	0.0005 (6)	0.0001 (6)	0.0038 (6)
C7	0.0158 (8)	0.0099 (7)	0.0113 (7)	0.0021 (6)	0.0025 (6)	0.0035 (6)
C8	0.0121 (7)	0.0135 (7)	0.0148 (8)	0.0016 (6)	0.0046 (6)	0.0049 (6)
C9	0.0130 (7)	0.0128 (7)	0.0102 (7)	0.0022 (6)	0.0003 (6)	0.0051 (6)
C10	0.0142 (8)	0.0165 (8)	0.0174 (8)	0.0040 (6)	0.0051 (6)	0.0049 (6)
C11	0.0155 (8)	0.0190 (8)	0.0194 (8)	−0.0008 (6)	0.0040 (7)	0.0078 (7)
C12	0.0199 (8)	0.0129 (7)	0.0151 (8)	0.0010 (6)	0.0011 (6)	0.0048 (6)
C13	0.0161 (8)	0.0142 (8)	0.0150 (8)	0.0045 (6)	0.0028 (6)	0.0043 (6)
C14	0.0122 (7)	0.0159 (8)	0.0141 (8)	0.0021 (6)	0.0029 (6)	0.0063 (6)

Geometric parameters (Å, º)

I1—C1	2.0787 (16)	C6—H6	0.9500
N1—C1	1.372 (2)	C8—C9	1.522 (2)
N1—C7	1.392 (2)	C8—H8B	0.9900
N1—C8	1.459 (2)	C8—H8A	0.9900
C1—N2	1.310 (2)	C9—C14	1.392 (2)
N2—C2	1.398 (2)	C9—C10	1.399 (2)
C2—C3	1.399 (2)	C10—C11	1.392 (2)
C2—C7	1.403 (2)	C10—H10	0.9500
C3—C4	1.388 (3)	C11—C12	1.389 (2)
C3—H3	0.9500	C11—H11	0.9500
C4—C5	1.406 (3)	C12—C13	1.394 (2)
C4—H4	0.9500	C12—H12	0.9500
C5—C6	1.390 (2)	C13—C14	1.399 (2)
C5—H5	0.9500	C13—H13	0.9500
C6—C7	1.393 (2)	C14—H14	0.9500
C1—N1—C7	105.30 (13)	N1—C8—C9	112.67 (13)
C1—N1—C8	129.42 (14)	N1—C8—H8B	109.1
C7—N1—C8	124.77 (14)	C9—C8—H8B	109.1
N2—C1—N1	114.90 (14)	N1—C8—H8A	109.1
N2—C1—I1	122.95 (12)	C9—C8—H8A	109.1
N1—C1—I1	122.10 (12)	H8B—C8—H8A	107.8
C1—N2—C2	103.99 (14)	C14—C9—C10	119.12 (15)
N2—C2—C3	130.02 (16)	C14—C9—C8	122.54 (14)
N2—C2—C7	110.06 (14)	C10—C9—C8	118.33 (14)
C3—C2—C7	119.90 (16)	C11—C10—C9	120.50 (16)
C4—C3—C2	117.39 (16)	C11—C10—H10	119.8
C4—C3—H3	121.3	C9—C10—H10	119.8
C2—C3—H3	121.3	C12—C11—C10	120.19 (16)
C3—C4—C5	121.86 (16)	C12—C11—H11	119.9
C3—C4—H4	119.1	C10—C11—H11	119.9
C5—C4—H4	119.1	C11—C12—C13	119.71 (15)
C6—C5—C4	121.53 (16)	C11—C12—H12	120.1
C6—C5—H5	119.2	C13—C12—H12	120.1
C4—C5—H5	119.2	C12—C13—C14	120.09 (16)
C5—C6—C7	116.04 (16)	C12—C13—H13	120.0
C5—C6—H6	122.0	C14—C13—H13	120.0
C7—C6—H6	122.0	C9—C14—C13	120.39 (15)
N1—C7—C6	131.00 (15)	C9—C14—H14	119.8
N1—C7—C2	105.74 (14)	C13—C14—H14	119.8
C6—C7—C2	123.26 (15)
C7—N1—C1—N2	−0.68 (19)	C5—C6—C7—C2	1.7 (2)
C8—N1—C1—N2	−172.65 (15)	N2—C2—C7—N1	−0.90 (18)
C7—N1—C1—I1	−178.20 (11)	C3—C2—C7—N1	177.77 (15)
C8—N1—C1—I1	9.8 (2)	N2—C2—C7—C6	179.92 (15)
N1—C1—N2—C2	0.12 (19)	C3—C2—C7—C6	−1.4 (3)
I1—C1—N2—C2	177.62 (11)	C1—N1—C8—C9	93.38 (19)
C1—N2—C2—C3	−178.00 (18)	C7—N1—C8—C9	−77.17 (19)
C1—N2—C2—C7	0.49 (18)	N1—C8—C9—C14	−13.4 (2)
N2—C2—C3—C4	178.48 (17)	N1—C8—C9—C10	167.25 (14)
C7—C2—C3—C4	0.1 (3)	C14—C9—C10—C11	−0.2 (2)
C2—C3—C4—C5	0.8 (3)	C8—C9—C10—C11	179.10 (15)
C3—C4—C5—C6	−0.5 (3)	C9—C10—C11—C12	0.1 (3)
C4—C5—C6—C7	−0.7 (3)	C10—C11—C12—C13	0.4 (3)
C1—N1—C7—C6	−179.98 (17)	C11—C12—C13—C14	−0.8 (3)
C8—N1—C7—C6	−7.5 (3)	C10—C9—C14—C13	−0.1 (2)
C1—N1—C7—C2	0.92 (17)	C8—C9—C14—C13	−179.45 (15)
C8—N1—C7—C2	173.37 (14)	C12—C13—C14—C9	0.6 (3)
C5—C6—C7—N1	−177.29 (16)