Isomeric Schiff bases related by dual imino-group reversals

Two isomeric pairs of Schiff bases, N,N′-bis­(2-methoxy­benzyl­idene)-p-phenyl­enediamine, C₂₂H₂₀N₂O₂, (I), and 2,2′-dimeth­oxy-N,N-(p-phenyl­enedimethyl­ene)dianiline, C₂₂H₂₀N₂O₂, (II), and (E,E)-1,4-bis­(3-iodo­phen­yl)-2,3-diaza­buta-1,3-diene (alternative name: 3-iodo­benzaldehyde azine), C₁₄H₁₀I₂N₂, (III), and N,N′-bis­(3-iodo­phen­yl)ethylenedi­imine, C₁₄H₁₀I₂N₂ [JAYFEV; Cho, Moore & Wilson (2005). Acta Cryst. E61, o3773–o3774], differ pairwise only in the orientation of their imino linkages and in all four individual cases occupy inversion centers in the crystal, yet all four compounds are found to assume unique packing arrangements. Compounds (I) and (II) differ substantially in mol­ecular conformation, possessing angles between their ring planes of 12.10 (15) and 46.29 (9)°, respectively. Compound (III) and JAYFEV are similar to each other in conformation, with angles between their imino linkages and benzene rings of 11.57 (15) and 7.4 (3)°, respectively. The crystal structures are distinguished from each other by different packing motifs involving the functional groups. Inter­molecular contacts between meth­oxy groups define an R₂²(6) motif in (I) but a C(3) motif in (II). Inter­molecular contacts are of the I...I type in (III), but they are of the N...I type in JAYFEV.

Computing details

For all compounds, data collection: SMART (Bruker, 2001). Cell refinement: SAINT-Plus,(Bruker, 2003) for (I); SAINT-Plus (Bruker, 2003) for (II), (III). For all compounds, data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

(I) N,N'-bis(2-methoxybenzylidene)phenylene-1,4-diamine

Crystal data

C22H20N2O2	Dx = 1.310 Mg m^−3
Mr = 344.40	Melting point = 149–151 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 5.9580 (5) Å	Cell parameters from 2198 reflections
b = 12.2984 (10) Å	θ = 2.4–25.0°
c = 11.9168 (9) Å	µ = 0.09 mm^−1
β = 90.185 (1)°	T = 173 K
V = 873.19 (12) Å^3	Needle, yellow
Z = 2	0.48 × 0.20 × 0.18 mm
F(000) = 364

Data collection

Bruker PLATFORM/SMART CCD area-detector diffractometer	1543 independent reflections
Radiation source: normal-focus sealed tube	1418 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000; Blessing, 1995)	h = −7→7
Tmin = 0.957, Tmax = 0.982	k = −14→14
7597 measured reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.094	H-atom parameters constrained
S = 1.14	w = 1/[σ^2(Fo^2) + (0.0366P)^2 + 0.282P] where P = (Fo^2 + 2Fc^2)/3
1543 reflections	(Δ/σ)max < 0.001
119 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

Experimental. (Melting points were determined on a Fisher-Johns melting point apparatus and are uncorrected.)

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	0.0407 (2)	0.18569 (11)	0.15406 (11)	0.0266 (3)
C2	0.0632 (2)	0.07187 (11)	0.14866 (11)	0.0269 (3)
C3	−0.0952 (2)	0.00537 (11)	0.19891 (11)	0.0303 (3)
H3	−0.0793	−0.0714	0.1952	0.036*
C4	−0.2761 (2)	0.05025 (12)	0.25424 (12)	0.0330 (3)
H4	−0.3845	0.0041	0.2879	0.040*
C5	−0.3007 (2)	0.16227 (12)	0.26102 (12)	0.0342 (3)
H5	−0.4251	0.1929	0.2994	0.041*
C6	−0.1429 (2)	0.22868 (11)	0.21155 (11)	0.0301 (3)
H6	−0.1595	0.3053	0.2167	0.036*
C7	0.2881 (3)	−0.08005 (11)	0.09169 (13)	0.0363 (4)
H7A	0.3024	−0.1055	0.1693	0.054*
H7B	0.4276	−0.0950	0.0512	0.054*
H7C	0.1634	−0.1180	0.0549	0.054*
C8	0.2015 (2)	0.25688 (11)	0.09754 (11)	0.0289 (3)
H8	0.3150	0.2253	0.0522	0.035*
C9	0.3524 (2)	0.42638 (10)	0.05186 (10)	0.0251 (3)
C10	0.2974 (2)	0.53613 (10)	0.04102 (11)	0.0280 (3)
H10	0.1581	0.5614	0.0695	0.034*
C11	0.5591 (2)	0.39127 (10)	0.01014 (11)	0.0278 (3)
H11	0.6009	0.3170	0.0171	0.033*
N1	0.19386 (19)	0.35969 (9)	0.10739 (9)	0.0281 (3)
O1	0.24547 (17)	0.03454 (7)	0.09121 (8)	0.0355 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0287 (7)	0.0229 (7)	0.0284 (7)	−0.0026 (5)	0.0012 (6)	0.0020 (5)
C2	0.0294 (7)	0.0237 (7)	0.0277 (7)	−0.0009 (5)	0.0017 (5)	0.0003 (5)
C3	0.0350 (8)	0.0202 (7)	0.0357 (8)	−0.0038 (6)	0.0018 (6)	0.0033 (6)
C4	0.0315 (8)	0.0299 (8)	0.0375 (8)	−0.0074 (6)	0.0050 (6)	0.0060 (6)
C5	0.0304 (8)	0.0308 (8)	0.0413 (8)	0.0001 (6)	0.0088 (6)	0.0020 (6)
C6	0.0321 (8)	0.0208 (7)	0.0374 (8)	−0.0009 (5)	0.0048 (6)	0.0010 (6)
C7	0.0439 (9)	0.0215 (7)	0.0434 (8)	0.0037 (6)	0.0072 (7)	−0.0004 (6)
C8	0.0300 (8)	0.0246 (7)	0.0320 (7)	−0.0004 (5)	0.0063 (6)	−0.0002 (6)
C9	0.0277 (7)	0.0214 (7)	0.0263 (7)	−0.0022 (5)	0.0019 (5)	0.0005 (5)
C10	0.0263 (7)	0.0234 (7)	0.0344 (7)	0.0014 (5)	0.0063 (5)	−0.0006 (6)
C11	0.0304 (8)	0.0164 (6)	0.0367 (8)	0.0009 (5)	0.0036 (6)	0.0016 (5)
N1	0.0294 (6)	0.0214 (6)	0.0337 (6)	−0.0017 (5)	0.0061 (5)	0.0024 (5)
O1	0.0386 (6)	0.0207 (5)	0.0471 (6)	0.0010 (4)	0.0157 (5)	0.0002 (4)

Geometric parameters (Å, º)

C1—C6	1.3964 (19)	C7—O1	1.4320 (16)
C1—C2	1.4077 (19)	C7—H7A	0.98
C1—C8	1.4640 (18)	C7—H7B	0.98
C2—O1	1.3650 (16)	C7—H7C	0.98
C2—C3	1.3865 (19)	C8—N1	1.2707 (18)
C3—C4	1.380 (2)	C8—H8	0.95
C3—H3	0.95	C9—C10	1.3949 (19)
C4—C5	1.388 (2)	C9—C11	1.3977 (18)
C4—H4	0.95	C9—N1	1.4167 (17)
C5—C6	1.3790 (19)	C10—C11^i	1.3798 (18)
C5—H5	0.95	C10—H10	0.95
C6—H6	0.95	C11—H11	0.95
C6—C1—C2	118.29 (12)	O1—C7—H7B	110
C6—C1—C8	120.95 (12)	H7A—C7—H7B	110
C2—C1—C8	120.72 (12)	O1—C7—H7C	110
O1—C2—C3	124.20 (12)	H7A—C7—H7C	110
O1—C2—C1	115.70 (11)	H7B—C7—H7C	110
C3—C2—C1	120.10 (12)	N1—C8—C1	121.93 (12)
C4—C3—C2	120.27 (13)	N1—C8—H8	119
C4—C3—H3	120	C1—C8—H8	119
C2—C3—H3	120	C10—C9—C11	118.24 (12)
C3—C4—C5	120.50 (13)	C10—C9—N1	116.52 (11)
C3—C4—H4	120	C11—C9—N1	125.23 (12)
C5—C4—H4	120	C11^i—C10—C9	121.41 (12)
C6—C5—C4	119.39 (13)	C11^i—C10—H10	119
C6—C5—H5	120	C9—C10—H10	119
C4—C5—H5	120	C10^i—C11—C9	120.35 (12)
C5—C6—C1	121.44 (13)	C10^i—C11—H11	120
C5—C6—H6	119	C9—C11—H11	120
C1—C6—H6	119	C8—N1—C9	120.58 (11)
O1—C7—H7A	110	C2—O1—C7	118.05 (11)
C6—C1—C2—O1	179.86 (12)	C6—C1—C8—N1	7.0 (2)
C8—C1—C2—O1	1.90 (19)	C2—C1—C8—N1	−175.14 (13)
C6—C1—C2—C3	0.5 (2)	C11—C9—C10—C11^i	0.5 (2)
C8—C1—C2—C3	−177.49 (12)	N1—C9—C10—C11^i	179.05 (12)
O1—C2—C3—C4	−179.20 (12)	C10—C9—C11—C10^i	−0.5 (2)
C1—C2—C3—C4	0.1 (2)	N1—C9—C11—C10^i	−178.91 (12)
C2—C3—C4—C5	−0.5 (2)	C1—C8—N1—C9	179.82 (11)
C3—C4—C5—C6	0.2 (2)	C10—C9—N1—C8	162.75 (13)
C4—C5—C6—C1	0.4 (2)	C11—C9—N1—C8	−18.8 (2)
C2—C1—C6—C5	−0.7 (2)	C3—C2—O1—C7	−6.2 (2)
C8—C1—C6—C5	177.21 (13)	C1—C2—O1—C7	174.42 (12)

Symmetry code: (i) −x+1, −y+1, −z.

(II) 2,2'-dimethoxy-(p-phenylenedimethylene)dianiline

Crystal data

C22H20N2O2	Dx = 1.277 Mg m^−3
Mr = 344.40	Melting point = 178–180 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.1825 (4) Å	Cell parameters from 4025 reflections
b = 7.2077 (4) Å	θ = 2.4–25.0°
c = 17.3048 (10) Å	µ = 0.08 mm^−1
β = 91.068 (1)°	T = 173 K
V = 895.70 (9) Å^3	Prism, yellow
Z = 2	0.52 × 0.25 × 0.20 mm
F(000) = 364

Data collection

Bruker PLATFORM/SMART CCD area-detector diffractometer	1583 independent reflections
Radiation source: normal-focus sealed tube	1392 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000; Blessing, 1995)	h = −8→8
Tmin = 0.954, Tmax = 0.981	k = −8→8
8550 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.090	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0455P)^2 + 0.2159P] where P = (Fo^2 + 2Fc^2)/3
1583 reflections	(Δ/σ)max = 0.001
119 parameters	Δρmax = 0.13 e Å^−3
0 restraints	Δρmin = −0.17 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
C1	0.12635 (16)	0.52075 (16)	0.87726 (6)	0.0263 (3)
C2	0.17536 (16)	0.64991 (16)	0.82007 (7)	0.0286 (3)
C3	0.04336 (19)	0.77468 (18)	0.79202 (7)	0.0366 (3)
H3	0.0763	0.8630	0.7539	0.044*
C4	−0.13689 (19)	0.7705 (2)	0.81967 (8)	0.0417 (4)
H4	−0.2260	0.8575	0.8008	0.050*
C5	−0.18797 (18)	0.6419 (2)	0.87412 (7)	0.0385 (3)
H5	−0.3123	0.6379	0.8918	0.046*
C6	−0.05573 (17)	0.51806 (17)	0.90287 (7)	0.0318 (3)
H6	−0.0905	0.4299	0.9408	0.038*
C7	0.3998 (2)	0.7514 (2)	0.73027 (10)	0.0564 (4)
H7A	0.3145	0.7241	0.6869	0.085*
H7B	0.5279	0.7250	0.7151	0.085*
H7C	0.3890	0.8826	0.7444	0.085*
C8	0.23490 (16)	0.23783 (16)	0.92365 (6)	0.0274 (3)
H8	0.1176	0.1875	0.9085	0.033*
C9	0.37217 (16)	0.11740 (16)	0.96261 (6)	0.0264 (3)
C10	0.32917 (17)	−0.06887 (17)	0.97522 (7)	0.0299 (3)
H10	0.2119	−0.1162	0.9583	0.036*
C11	0.54470 (16)	0.18510 (16)	0.98797 (7)	0.0301 (3)
H11	0.5756	0.3117	0.9799	0.036*
N1	0.26845 (13)	0.40749 (14)	0.90959 (5)	0.0277 (3)
O1	0.35341 (11)	0.63883 (12)	0.79483 (5)	0.0352 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0310 (6)	0.0248 (6)	0.0230 (6)	0.0031 (5)	−0.0050 (4)	−0.0035 (4)
C2	0.0329 (6)	0.0249 (6)	0.0277 (6)	0.0004 (5)	−0.0045 (5)	−0.0022 (5)
C3	0.0455 (8)	0.0302 (7)	0.0340 (7)	0.0048 (6)	−0.0082 (6)	0.0040 (5)
C4	0.0441 (8)	0.0407 (8)	0.0398 (7)	0.0165 (6)	−0.0099 (6)	−0.0006 (6)
C5	0.0334 (7)	0.0489 (8)	0.0330 (7)	0.0113 (6)	−0.0019 (5)	−0.0070 (6)
C6	0.0355 (7)	0.0351 (7)	0.0249 (6)	0.0033 (5)	−0.0009 (5)	−0.0030 (5)
C7	0.0457 (8)	0.0646 (10)	0.0589 (10)	−0.0077 (8)	0.0041 (7)	0.0309 (8)
C8	0.0283 (6)	0.0287 (6)	0.0252 (6)	0.0005 (5)	−0.0009 (4)	−0.0002 (5)
C9	0.0307 (6)	0.0257 (6)	0.0230 (6)	0.0027 (5)	0.0016 (5)	0.0004 (4)
C10	0.0295 (6)	0.0279 (6)	0.0321 (6)	−0.0013 (5)	−0.0027 (5)	−0.0009 (5)
C11	0.0331 (6)	0.0227 (6)	0.0346 (7)	−0.0004 (5)	0.0007 (5)	0.0029 (5)
N1	0.0301 (5)	0.0272 (5)	0.0257 (5)	0.0030 (4)	−0.0014 (4)	0.0022 (4)
O1	0.0326 (5)	0.0358 (5)	0.0371 (5)	−0.0010 (4)	−0.0001 (4)	0.0107 (4)

Geometric parameters (Å, º)

C1—C6	1.3888 (17)	C7—O1	1.4253 (16)
C1—C2	1.4082 (17)	C7—H7A	0.98
C1—N1	1.4141 (15)	C7—H7B	0.98
C2—O1	1.3614 (15)	C7—H7C	0.98
C2—C3	1.3878 (17)	C8—N1	1.2708 (15)
C3—C4	1.389 (2)	C8—C9	1.4680 (16)
C3—H3	0.95	C8—H8	0.95
C4—C5	1.376 (2)	C9—C11	1.3950 (17)
C4—H4	0.95	C9—C10	1.3957 (17)
C5—C6	1.3889 (18)	C10—C11^i	1.3809 (17)
C5—H5	0.95	C10—H10	0.95
C6—H6	0.95	C11—H11	0.95
C6—C1—C2	118.86 (11)	O1—C7—H7B	110
C6—C1—N1	122.87 (11)	H7A—C7—H7B	110
C2—C1—N1	118.14 (10)	O1—C7—H7C	110
O1—C2—C3	124.44 (11)	H7A—C7—H7C	110
O1—C2—C1	115.81 (10)	H7B—C7—H7C	110
C3—C2—C1	119.74 (12)	N1—C8—C9	121.93 (11)
C2—C3—C4	120.05 (12)	N1—C8—H8	119
C2—C3—H3	120	C9—C8—H8	119
C4—C3—H3	120	C11—C9—C10	119.02 (11)
C5—C4—C3	120.82 (12)	C11—C9—C8	121.51 (11)
C5—C4—H4	120	C10—C9—C8	119.47 (11)
C3—C4—H4	120	C11^i—C10—C9	120.70 (11)
C4—C5—C6	119.27 (12)	C11^i—C10—H10	120
C4—C5—H5	120	C9—C10—H10	120
C6—C5—H5	120	C10^i—C11—C9	120.28 (11)
C1—C6—C5	121.23 (12)	C10^i—C11—H11	120
C1—C6—H6	119	C9—C11—H11	120
C5—C6—H6	119	C8—N1—C1	119.56 (10)
O1—C7—H7A	110	C2—O1—C7	116.93 (10)
C6—C1—C2—O1	−176.81 (10)	N1—C8—C9—C11	1.75 (17)
N1—C1—C2—O1	7.20 (15)	N1—C8—C9—C10	−178.74 (11)
C6—C1—C2—C3	1.74 (17)	C11—C9—C10—C11^i	−0.18 (19)
N1—C1—C2—C3	−174.24 (11)	C8—C9—C10—C11^i	−179.70 (11)
O1—C2—C3—C4	177.67 (12)	C10—C9—C11—C10^i	0.18 (19)
C1—C2—C3—C4	−0.75 (18)	C8—C9—C11—C10^i	179.69 (11)
C2—C3—C4—C5	−0.9 (2)	C9—C8—N1—C1	−175.21 (10)
C3—C4—C5—C6	1.5 (2)	C6—C1—N1—C8	44.03 (16)
C2—C1—C6—C5	−1.12 (17)	C2—C1—N1—C8	−140.16 (11)
N1—C1—C6—C5	174.66 (11)	C3—C2—O1—C7	−6.27 (18)
C4—C5—C6—C1	−0.51 (19)	C1—C2—O1—C7	172.21 (12)

Symmetry code: (i) −x+1, −y, −z+2.

(III) (E,E)-1,4-bis(3-iodophenyl)-2,3-diazabuta-1,3-diene

Crystal data

C14H10I2N2	Dx = 2.195 Mg m^−3
Mr = 460.04	Melting point = 148–150 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 4.1216 (4) Å	Cell parameters from 3299 reflections
b = 15.2474 (16) Å	θ = 2.3–27.5°
c = 11.0751 (12) Å	µ = 4.50 mm^−1
β = 90.707 (2)°	T = 173 K
V = 695.95 (12) Å^3	Needle, yellow
Z = 2	0.50 × 0.15 × 0.15 mm
F(000) = 428

Data collection

Siemens PLATFORM/SMART CCD area-detector diffractometer	1615 independent reflections
Radiation source: normal-focus sealed tube	1542 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 27.6°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000; Blessing, 1995)	h = −5→5
Tmin = 0.293, Tmax = 0.509	k = −19→19
8140 measured reflections	l = −14→14

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)] = 0.015	H-atom parameters constrained
wR(F^2) = 0.035	w = 1/[σ^2(Fo^2) + (0.0109P)^2 + 0.3499P] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max = 0.004
1615 reflections	Δρmax = 0.40 e Å^−3
83 parameters	Δρmin = −0.45 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0213 (6)

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	0.7633 (4)	0.86481 (11)	0.67086 (16)	0.0217 (3)
C2	0.6408 (4)	0.78630 (11)	0.62329 (16)	0.0214 (3)
H2	0.5236	0.7862	0.5489	0.026*
C3	0.6919 (4)	0.70900 (11)	0.68555 (16)	0.0209 (3)
C4	0.8590 (5)	0.70748 (12)	0.79623 (17)	0.0256 (4)
H4	0.8888	0.6541	0.8391	0.031*
C5	0.9799 (5)	0.78548 (13)	0.84180 (17)	0.0276 (4)
H5	1.0943	0.7855	0.9168	0.033*
C6	0.9367 (5)	0.86358 (12)	0.77989 (17)	0.0262 (4)
H6	1.0253	0.9164	0.8117	0.031*
C7	0.7082 (5)	0.94892 (12)	0.60949 (17)	0.0250 (4)
H7	0.8244	0.9993	0.6363	0.030*
I1	0.51243 (3)	0.591153 (7)	0.613685 (11)	0.02654 (7)
N1	0.5084 (4)	0.95618 (10)	0.52113 (15)	0.0276 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0248 (8)	0.0186 (8)	0.0218 (8)	0.0004 (7)	0.0028 (7)	0.0001 (7)
C2	0.0239 (8)	0.0191 (8)	0.0212 (8)	0.0020 (7)	−0.0007 (6)	−0.0005 (6)
C3	0.0215 (8)	0.0165 (8)	0.0247 (9)	0.0001 (6)	0.0020 (7)	−0.0011 (6)
C4	0.0304 (9)	0.0226 (9)	0.0237 (9)	0.0050 (7)	−0.0005 (7)	0.0037 (7)
C5	0.0321 (10)	0.0291 (10)	0.0216 (8)	0.0038 (8)	−0.0053 (7)	−0.0021 (7)
C6	0.0283 (9)	0.0225 (9)	0.0277 (9)	−0.0007 (7)	−0.0001 (7)	−0.0049 (7)
C7	0.0319 (9)	0.0162 (8)	0.0271 (9)	−0.0015 (7)	0.0045 (7)	−0.0012 (7)
I1	0.02734 (9)	0.01759 (8)	0.03468 (10)	−0.00227 (4)	−0.00077 (5)	−0.00046 (4)
N1	0.0364 (9)	0.0165 (7)	0.0298 (8)	−0.0002 (7)	0.0003 (7)	0.0026 (6)

Geometric parameters (Å, º)

C1—C6	1.396 (3)	C4—H4	0.95
C1—C2	1.400 (2)	C5—C6	1.384 (3)
C1—C7	1.468 (2)	C5—H5	0.95
C2—C3	1.380 (2)	C6—H6	0.95
C2—H2	0.95	C7—N1	1.276 (3)
C3—C4	1.399 (3)	C7—H7	0.95
C3—I1	2.0964 (17)	N1—N1^i	1.417 (3)
C4—C5	1.382 (3)
C6—C1—C2	119.52 (16)	C3—C4—H4	121
C6—C1—C7	119.14 (16)	C4—C5—C6	121.05 (17)
C2—C1—C7	121.33 (16)	C4—C5—H5	120
C3—C2—C1	119.35 (16)	C6—C5—H5	120
C3—C2—H2	120	C5—C6—C1	120.08 (17)
C1—C2—H2	120	C5—C6—H6	120
C2—C3—C4	121.49 (16)	C1—C6—H6	120
C2—C3—I1	119.42 (13)	N1—C7—C1	121.71 (17)
C4—C3—I1	119.09 (13)	N1—C7—H7	119
C5—C4—C3	118.49 (17)	C1—C7—H7	119
C5—C4—H4	121	C7—N1—N1^i	111.33 (19)
C6—C1—C2—C3	0.4 (3)	C4—C5—C6—C1	1.3 (3)
C7—C1—C2—C3	−178.47 (16)	C2—C1—C6—C5	−1.6 (3)
C1—C2—C3—C4	1.1 (3)	C7—C1—C6—C5	177.32 (17)
C1—C2—C3—I1	−179.43 (13)	C6—C1—C7—N1	−168.26 (18)
C2—C3—C4—C5	−1.3 (3)	C2—C1—C7—N1	10.6 (3)
I1—C3—C4—C5	179.15 (14)	C1—C7—N1—N1^i	178.61 (18)
C3—C4—C5—C6	0.1 (3)

Symmetry code: (i) −x+1, −y+2, −z+1.