Structural and luminescent properties of co-crystals of tetra­iodo­ethyl­ene with two aza­phenanthrenes

Two new co-crystals of tetra­iodo­ethyl­ene with two aza­phenanthrenes were successfully synthesized. In the crystals, C—I...π and C—I...N halogen bonds link the mol­ecules. A study of their luminescence properties indicates that co-crystals 1 and 2 exhibit distinctly different luminescence in the solid state at room temperature.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.011 Å
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.043
• wR factor = 0.078
• Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Datablock: 1


Alert level C
PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.01073 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      4.448 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          7 Report

Alert level G
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large      28.97 Why ?
PLAT431_ALERT_2_G Short Inter HL..A Contact  I1       ..N1       .       2.86 Ang.
                                                    x,1+y,z  =      1_565 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  I2       ..C9               3.43 Ang.
                                              1/2+x,1/2+y,z  =      3_555 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          9 Note
PLAT955_ALERT_1_G Reported (CIF) and Actual (FCF) Lmax Differ by .          1 Units
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: 2


Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          3 Report

Alert level G
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT431_ALERT_2_G Short Inter HL..A Contact  I1       ..N1       .       2.90 Ang.
                                                      x,y,z  =      1_555 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  I2       ..C13              3.44 Ang.
                                                 -x,1-y,1-z  =      2_566 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

For both structures, data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015). Molecular graphics: SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg, 2005) for (1); SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg, 2005), for (2). For both structures, software used to prepare material for publication: publCIF (Westrip, 2010).

Tetraiodoethylene–phenanthridine (1/2) (1)

Crystal data

0.5C2I4·C13H9N	F(000) = 1648
Mr = 445.02	Dx = 2.257 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 24.2920 (18) Å	Cell parameters from 5311 reflections
b = 4.8348 (4) Å	θ = 3.1–26.3°
c = 24.8761 (16) Å	µ = 4.78 mm^−1
β = 116.272 (2)°	T = 296 K
V = 2619.8 (3) Å^3	Block, yellow
Z = 8	0.30 × 0.25 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer	1782 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.045
φ and ω scans	θmax = 26.3°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −30→29
Tmin = 0.489, Tmax = 0.745	k = −6→6
12094 measured reflections	l = −31→30
2635 independent 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)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.078	w = 1/[σ^2(Fo^2) + (0.0187P)^2 + 28.9715P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
2635 reflections	Δρmax = 1.08 e Å^−3
154 parameters	Δρmin = −0.61 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	0.70990 (2)	0.95088 (10)	0.57060 (2)	0.04011 (16)
I2	0.85225 (2)	0.96131 (11)	0.56611 (2)	0.04316 (16)
N1	0.6417 (3)	0.1927 (12)	0.6276 (2)	0.0377 (14)
C1	0.6440 (3)	0.1453 (14)	0.6836 (3)	0.0339 (16)
C2	0.6849 (3)	−0.0548 (15)	0.7193 (3)	0.0442 (18)
H2	0.708323	−0.152775	0.704671	0.053*
C3	0.6910 (4)	−0.1093 (16)	0.7755 (3)	0.053 (2)
H3	0.719345	−0.239978	0.799494	0.064*
C4	0.6547 (4)	0.0319 (17)	0.7965 (3)	0.054 (2)
H4	0.658318	−0.006933	0.834537	0.065*
C5	0.6141 (3)	0.2253 (16)	0.7623 (3)	0.0452 (19)
H5	0.590382	0.318582	0.777344	0.054*
C6	0.6070 (3)	0.2880 (14)	0.7044 (3)	0.0328 (16)
C7	0.5640 (3)	0.4901 (13)	0.6650 (3)	0.0342 (16)
C8	0.5240 (3)	0.6464 (16)	0.6801 (3)	0.0475 (19)
H8	0.524161	0.622630	0.717264	0.057*
C9	0.4853 (3)	0.8313 (17)	0.6406 (4)	0.054 (2)
H9	0.459174	0.933001	0.651309	0.065*
C10	0.4834 (3)	0.8741 (16)	0.5846 (4)	0.051 (2)
H10	0.456128	1.001451	0.558148	0.061*
C11	0.5219 (3)	0.7271 (15)	0.5691 (3)	0.0455 (19)
H11	0.521208	0.755053	0.531834	0.055*
C12	0.5627 (3)	0.5329 (14)	0.6091 (3)	0.0345 (16)
C13	0.6035 (3)	0.3779 (15)	0.5941 (3)	0.0405 (18)
H13	0.602707	0.412409	0.557015	0.049*
C14	0.7603 (3)	0.8233 (15)	0.5244 (3)	0.0411 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0411 (3)	0.0521 (3)	0.0327 (3)	0.0057 (2)	0.0213 (2)	−0.0022 (2)
I2	0.0332 (3)	0.0582 (3)	0.0364 (3)	−0.0048 (2)	0.0139 (2)	−0.0059 (2)
N1	0.034 (3)	0.046 (4)	0.037 (3)	0.000 (3)	0.019 (3)	−0.004 (3)
C1	0.034 (4)	0.036 (4)	0.033 (4)	−0.005 (3)	0.016 (3)	−0.005 (3)
C2	0.042 (4)	0.043 (4)	0.046 (4)	0.001 (4)	0.018 (4)	0.001 (4)
C3	0.060 (5)	0.049 (5)	0.041 (5)	0.000 (4)	0.013 (4)	0.011 (4)
C4	0.067 (6)	0.066 (6)	0.027 (4)	−0.015 (5)	0.019 (4)	−0.001 (4)
C5	0.048 (5)	0.053 (5)	0.041 (4)	−0.010 (4)	0.026 (4)	−0.008 (4)
C6	0.031 (4)	0.038 (4)	0.030 (4)	−0.008 (3)	0.014 (3)	−0.007 (3)
C7	0.032 (4)	0.034 (4)	0.041 (4)	−0.006 (3)	0.020 (3)	−0.008 (3)
C8	0.045 (5)	0.053 (5)	0.049 (5)	−0.002 (4)	0.026 (4)	−0.005 (4)
C9	0.031 (5)	0.051 (5)	0.081 (6)	−0.003 (4)	0.025 (4)	−0.015 (5)
C10	0.038 (5)	0.040 (5)	0.070 (6)	0.006 (4)	0.019 (4)	0.005 (4)
C11	0.042 (5)	0.049 (5)	0.039 (4)	−0.012 (4)	0.012 (4)	−0.003 (4)
C12	0.030 (4)	0.036 (4)	0.033 (4)	−0.003 (3)	0.010 (3)	−0.001 (3)
C13	0.046 (5)	0.052 (5)	0.030 (4)	−0.005 (4)	0.023 (4)	−0.002 (4)
C14	0.045 (5)	0.044 (5)	0.043 (4)	0.007 (4)	0.028 (4)	0.003 (3)

Geometric parameters (Å, º)

I1—C14	2.108 (6)	C6—C7	1.449 (9)
I2—C14	2.111 (7)	C7—C12	1.394 (9)
N1—C13	1.293 (8)	C7—C8	1.406 (9)
N1—C1	1.390 (8)	C8—C9	1.353 (10)
C1—C2	1.389 (9)	C8—H8	0.9300
C1—C6	1.400 (9)	C9—C10	1.387 (11)
C2—C3	1.364 (10)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.360 (10)
C3—C4	1.389 (11)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.408 (9)
C4—C5	1.352 (10)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.416 (9)
C5—C6	1.406 (9)	C13—H13	0.9300
C5—H5	0.9300	C14—C14^i	1.301 (13)
C13—N1—C1	117.3 (6)	C9—C8—C7	120.1 (7)
N1—C1—C2	117.1 (6)	C9—C8—H8	120.0
N1—C1—C6	122.8 (6)	C7—C8—H8	120.0
C2—C1—C6	120.1 (6)	C8—C9—C10	122.1 (7)
C3—C2—C1	120.8 (7)	C8—C9—H9	119.0
C3—C2—H2	119.6	C10—C9—H9	119.0
C1—C2—H2	119.6	C11—C10—C9	119.0 (7)
C2—C3—C4	119.4 (7)	C11—C10—H10	120.5
C2—C3—H3	120.3	C9—C10—H10	120.5
C4—C3—H3	120.3	C10—C11—C12	120.4 (7)
C5—C4—C3	120.8 (7)	C10—C11—H11	119.8
C5—C4—H4	119.6	C12—C11—H11	119.8
C3—C4—H4	119.6	C7—C12—C11	120.1 (6)
C4—C5—C6	121.2 (7)	C7—C12—C13	118.4 (6)
C4—C5—H5	119.4	C11—C12—C13	121.6 (6)
C6—C5—H5	119.4	N1—C13—C12	125.7 (6)
C1—C6—C5	117.7 (6)	N1—C13—H13	117.1
C1—C6—C7	118.1 (6)	C12—C13—H13	117.1
C5—C6—C7	124.2 (6)	C14^i—C14—I2	121.2 (7)
C12—C7—C8	118.3 (7)	C14^i—C14—I1	126.2 (7)
C12—C7—C6	117.7 (6)	I2—C14—I1	112.5 (3)
C8—C7—C6	124.0 (6)
C13—N1—C1—C2	179.7 (6)	C5—C6—C7—C8	−0.3 (11)
C13—N1—C1—C6	0.2 (10)	C12—C7—C8—C9	0.5 (11)
N1—C1—C2—C3	178.4 (7)	C6—C7—C8—C9	179.9 (7)
C6—C1—C2—C3	−2.1 (11)	C7—C8—C9—C10	0.0 (12)
C1—C2—C3—C4	1.8 (12)	C8—C9—C10—C11	−0.5 (12)
C2—C3—C4—C5	−1.0 (12)	C9—C10—C11—C12	0.5 (11)
C3—C4—C5—C6	0.5 (12)	C8—C7—C12—C11	−0.5 (10)
N1—C1—C6—C5	−179.0 (6)	C6—C7—C12—C11	−179.9 (6)
C2—C1—C6—C5	1.5 (10)	C8—C7—C12—C13	179.3 (6)
N1—C1—C6—C7	1.0 (10)	C6—C7—C12—C13	−0.2 (10)
C2—C1—C6—C7	−178.5 (6)	C10—C11—C12—C7	0.0 (10)
C4—C5—C6—C1	−0.7 (10)	C10—C11—C12—C13	−179.7 (7)
C4—C5—C6—C7	179.3 (7)	C1—N1—C13—C12	−1.4 (10)
C1—C6—C7—C12	−0.9 (9)	C7—C12—C13—N1	1.5 (11)
C5—C6—C7—C12	179.1 (7)	C11—C12—C13—N1	−178.8 (7)
C1—C6—C7—C8	179.7 (6)

Symmetry code: (i) −x+3/2, −y+3/2, −z+1.

Tetraiodoethylene–benzo[f]quinoline (1/2) (2)

Crystal data

0.5C2I4·C13H9N	Z = 2
Mr = 445.02	F(000) = 412
Triclinic, P1	Dx = 2.229 Mg m^−3
a = 7.3179 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.1089 (5) Å	Cell parameters from 4699 reflections
c = 11.3252 (7) Å	θ = 2.8–26.4°
α = 97.050 (2)°	µ = 4.72 mm^−1
β = 92.059 (2)°	T = 296 K
γ = 95.579 (2)°	Block, yellow
V = 663.02 (7) Å^3	0.35 × 0.32 × 0.30 mm

Data collection

Bruker APEXII CCD diffractometer	2099 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.026
φ and ω scans	θmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −9→9
Tmin = 0.638, Tmax = 0.745	k = −10→10
8567 measured reflections	l = −14→14
2701 independent 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)] = 0.028	H-atom parameters constrained
wR(F^2) = 0.058	w = 1/[σ^2(Fo^2) + (0.0189P)^2 + 0.7413P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
2701 reflections	Δρmax = 0.80 e Å^−3
154 parameters	Δρmin = −0.74 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	0.20988 (4)	0.45307 (3)	0.82595 (2)	0.04767 (10)
I2	−0.08934 (4)	0.75374 (3)	0.91391 (3)	0.05167 (11)
N1	0.4565 (5)	0.3596 (5)	0.6400 (3)	0.0518 (9)
C1	0.6267 (7)	0.4270 (6)	0.6615 (4)	0.0597 (13)
H1	0.655445	0.495377	0.733212	0.072*
C2	0.7655 (7)	0.4022 (6)	0.5841 (5)	0.0613 (13)
H2	0.883874	0.453358	0.603495	0.074*
C3	0.7274 (6)	0.3026 (6)	0.4794 (5)	0.0541 (12)
H3	0.819507	0.286190	0.425958	0.065*
C4	0.5492 (5)	0.2240 (5)	0.4514 (4)	0.0399 (10)
C5	0.4171 (5)	0.2587 (5)	0.5350 (4)	0.0389 (9)
C6	0.2327 (6)	0.1869 (5)	0.5119 (4)	0.0470 (11)
H6	0.144788	0.211154	0.566982	0.056*
C7	0.1844 (6)	0.0845 (5)	0.4114 (4)	0.0471 (11)
H7	0.062732	0.038787	0.398340	0.057*
C8	0.3128 (6)	0.0431 (5)	0.3238 (4)	0.0424 (10)
C9	0.4960 (6)	0.1144 (5)	0.3424 (4)	0.0418 (10)
C10	0.6199 (7)	0.0731 (6)	0.2544 (4)	0.0561 (12)
H10	0.741510	0.119847	0.264207	0.067*
C11	0.5643 (9)	−0.0348 (7)	0.1546 (5)	0.0730 (16)
H11	0.648615	−0.060734	0.097457	0.088*
C12	0.3842 (9)	−0.1063 (7)	0.1373 (4)	0.0716 (16)
H12	0.347907	−0.180218	0.069304	0.086*
C13	0.2612 (7)	−0.0676 (6)	0.2203 (4)	0.0555 (12)
H13	0.140145	−0.115380	0.208420	0.067*
C14	0.0238 (6)	0.5360 (5)	0.9536 (4)	0.0449 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0579 (2)	0.04585 (18)	0.04064 (16)	0.01385 (14)	0.01030 (14)	0.00193 (12)
I2	0.0700 (2)	0.04158 (18)	0.04756 (18)	0.02041 (15)	0.00980 (15)	0.00849 (13)
N1	0.058 (3)	0.051 (2)	0.049 (2)	0.0117 (19)	0.003 (2)	0.0083 (18)
C1	0.068 (3)	0.052 (3)	0.058 (3)	0.007 (3)	−0.016 (3)	0.006 (2)
C2	0.042 (3)	0.067 (3)	0.076 (4)	−0.002 (2)	−0.010 (3)	0.024 (3)
C3	0.039 (3)	0.055 (3)	0.073 (3)	0.006 (2)	0.013 (2)	0.026 (3)
C4	0.036 (2)	0.041 (2)	0.049 (2)	0.0109 (18)	0.008 (2)	0.0221 (19)
C5	0.041 (2)	0.036 (2)	0.043 (2)	0.0108 (18)	0.0065 (19)	0.0135 (18)
C6	0.042 (2)	0.054 (3)	0.048 (3)	0.008 (2)	0.015 (2)	0.009 (2)
C7	0.036 (2)	0.051 (3)	0.056 (3)	0.003 (2)	0.006 (2)	0.016 (2)
C8	0.051 (3)	0.036 (2)	0.044 (2)	0.0087 (19)	0.006 (2)	0.0144 (18)
C9	0.046 (2)	0.042 (2)	0.044 (2)	0.0161 (19)	0.014 (2)	0.0199 (19)
C10	0.059 (3)	0.066 (3)	0.052 (3)	0.023 (2)	0.021 (2)	0.022 (2)
C11	0.099 (5)	0.080 (4)	0.051 (3)	0.043 (4)	0.031 (3)	0.018 (3)
C12	0.115 (5)	0.059 (3)	0.044 (3)	0.025 (3)	0.007 (3)	0.004 (2)
C13	0.072 (3)	0.047 (3)	0.049 (3)	0.009 (2)	−0.003 (3)	0.010 (2)
C14	0.054 (3)	0.039 (2)	0.041 (2)	0.011 (2)	0.002 (2)	−0.0017 (18)

Geometric parameters (Å, º)

I1—C14	2.116 (4)	C6—H6	0.9300
I2—C14	2.111 (4)	C7—C8	1.423 (6)
N1—C1	1.313 (6)	C7—H7	0.9300
N1—C5	1.363 (5)	C8—C13	1.402 (6)
C1—C2	1.379 (7)	C8—C9	1.405 (6)
C1—H1	0.9300	C9—C10	1.403 (6)
C2—C3	1.354 (7)	C10—C11	1.365 (7)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.402 (6)	C11—C12	1.384 (8)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.401 (5)	C12—C13	1.355 (7)
C4—C9	1.448 (6)	C12—H12	0.9300
C5—C6	1.418 (6)	C13—H13	0.9300
C6—C7	1.339 (6)	C14—C14^i	1.305 (8)
C1—N1—C5	117.4 (4)	C13—C8—C9	119.4 (4)
N1—C1—C2	123.8 (5)	C13—C8—C7	121.7 (4)
N1—C1—H1	118.1	C9—C8—C7	118.9 (4)
C2—C1—H1	118.1	C10—C9—C8	118.0 (4)
C3—C2—C1	119.2 (4)	C10—C9—C4	123.0 (4)
C3—C2—H2	120.4	C8—C9—C4	119.0 (4)
C1—C2—H2	120.4	C11—C10—C9	120.9 (5)
C2—C3—C4	120.1 (4)	C11—C10—H10	119.6
C2—C3—H3	120.0	C9—C10—H10	119.6
C4—C3—H3	120.0	C10—C11—C12	121.0 (5)
C3—C4—C5	116.5 (4)	C10—C11—H11	119.5
C3—C4—C9	124.0 (4)	C12—C11—H11	119.5
C5—C4—C9	119.5 (4)	C13—C12—C11	119.5 (5)
N1—C5—C4	123.0 (4)	C13—C12—H12	120.3
N1—C5—C6	117.1 (4)	C11—C12—H12	120.3
C4—C5—C6	119.9 (4)	C12—C13—C8	121.3 (5)
C7—C6—C5	120.4 (4)	C12—C13—H13	119.4
C7—C6—H6	119.8	C8—C13—H13	119.4
C5—C6—H6	119.8	C14^i—C14—I2	121.4 (4)
C6—C7—C8	122.3 (4)	C14^i—C14—I1	126.2 (4)
C6—C7—H7	118.9	I2—C14—I1	112.33 (18)
C8—C7—H7	118.9
C5—N1—C1—C2	0.5 (7)	C13—C8—C9—C10	1.1 (6)
N1—C1—C2—C3	−0.3 (8)	C7—C8—C9—C10	−179.4 (4)
C1—C2—C3—C4	−0.9 (7)	C13—C8—C9—C4	−177.9 (4)
C2—C3—C4—C5	1.7 (6)	C7—C8—C9—C4	1.6 (6)
C2—C3—C4—C9	−179.4 (4)	C3—C4—C9—C10	1.3 (6)
C1—N1—C5—C4	0.5 (6)	C5—C4—C9—C10	−179.8 (4)
C1—N1—C5—C6	−179.7 (4)	C3—C4—C9—C8	−179.7 (4)
C3—C4—C5—N1	−1.6 (6)	C5—C4—C9—C8	−0.9 (6)
C9—C4—C5—N1	179.5 (4)	C8—C9—C10—C11	−0.9 (6)
C3—C4—C5—C6	178.6 (4)	C4—C9—C10—C11	178.1 (4)
C9—C4—C5—C6	−0.3 (6)	C9—C10—C11—C12	0.1 (8)
N1—C5—C6—C7	−179.0 (4)	C10—C11—C12—C13	0.4 (8)
C4—C5—C6—C7	0.8 (6)	C11—C12—C13—C8	−0.2 (7)
C5—C6—C7—C8	−0.1 (7)	C9—C8—C13—C12	−0.5 (6)
C6—C7—C8—C13	178.4 (4)	C7—C8—C13—C12	180.0 (4)
C6—C7—C8—C9	−1.1 (6)

Symmetry code: (i) −x, −y+1, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···I2^ii	0.93	3.16	4.019 (5)	155
C6—H6···I1	0.93	3.31	3.945 (4)	127

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