3-Ethyl-1-[2-(1-ethyl­morpholinium-1-yl)ethyl]benzimidazolium diiodide monohydrate

The title compound, C₁₇H₂₇N₃O²⁺·2I⁻·H₂O, was synthesized from 1-(2-morpholinoethyl)benzimidazole and ethyl iodide in dimethyl­formamide. In the molecule, the benzimidazole ring is connected to the morpholine ring by an ethyl­ene group. The crystal structure is stabilized by inter- and intramolecular O—H...I, C—H...O and C—H...I interactions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.025
• wR factor = 0.056
• Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT432_ALERT_2_C Short Inter X...Y Contact  C5     ..  C5      ..       3.15 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

3-Ethyl-1-[2-(1-ethylmorpholinium-1-yl)ethyl]benzimidazolium diiodide monohydrate

Crystal data

C17H27N3O^2+·2I^−·H2O	F(000) = 1096
Mr = 561.23	Dx = 1.761 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 22695 reflections
a = 7.527 (5) Å	θ = 1.6–26.0°
b = 24.889 (5) Å	µ = 2.99 mm^−1
c = 11.757 (5) Å	T = 100 K
β = 106.007 (5)°	Prism, colorless
V = 2117.2 (17) Å^3	0.45 × 0.32 × 0.17 mm
Z = 4

Data collection

Stoe IPDS-II diffractometer	4039 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3870 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.096
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 1.6°
ω scans	h = −9→9
Absorption correction: integration STOE X-RED32 (Stoe & Cie, 2002)	k = −30→30
Tmin = 0.347, Tmax = 0.631	l = −14→14
23081 measured reflections

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.057	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0084P)^2 + 1.9938P] where P = (Fo^2 + 2Fc^2)/3
4039 reflections	(Δ/σ)max = 0.001
225 parameters	Δρmax = 0.47 e Å^−3
0 restraints	Δρmin = −0.82 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F^{2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F}2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of F}2 > σ(F^{2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F}2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O1	0.1811 (3)	0.23516 (7)	−0.35297 (19)	0.0242 (6)
N1	0.4164 (3)	0.41372 (7)	0.1550 (2)	0.0156 (6)
N2	0.1894 (3)	0.39741 (8)	−0.0024 (2)	0.0158 (6)
N3	−0.0272 (3)	0.32464 (8)	−0.2926 (2)	0.0159 (6)
C1	0.3618 (3)	0.46299 (9)	0.0991 (2)	0.0157 (7)
C2	0.4291 (4)	0.51467 (9)	0.1320 (3)	0.0176 (7)
C3	0.3465 (4)	0.55517 (9)	0.0553 (3)	0.0195 (7)
C4	0.2039 (4)	0.54525 (9)	−0.0481 (2)	0.0182 (7)
C5	0.1364 (4)	0.49350 (9)	−0.0795 (2)	0.0171 (7)
C6	0.2198 (3)	0.45306 (9)	−0.0012 (2)	0.0153 (7)
C7	0.3093 (3)	0.37603 (9)	0.0919 (2)	0.0160 (7)
C8	0.5647 (4)	0.40734 (9)	0.2648 (3)	0.0188 (7)
C9	0.5949 (4)	0.34927 (10)	0.3022 (3)	0.0294 (9)
C10	0.0457 (4)	0.36712 (9)	−0.0880 (2)	0.0175 (7)
C11	0.1078 (3)	0.35798 (9)	−0.1994 (2)	0.0157 (7)
C12	−0.0420 (4)	0.26669 (9)	−0.2536 (2)	0.0185 (7)
C13	0.1336 (4)	0.23501 (9)	−0.2433 (3)	0.0211 (7)
C14	0.2142 (4)	0.28894 (9)	−0.3849 (3)	0.0211 (8)
C15	0.0397 (4)	0.32216 (10)	−0.4031 (2)	0.0194 (7)
C16	−0.2235 (3)	0.34734 (10)	−0.3248 (3)	0.0207 (8)
C17	−0.2392 (4)	0.40547 (10)	−0.3656 (3)	0.0261 (8)
O2	0.1875 (3)	0.46689 (8)	0.6522 (2)	0.0285 (6)
I1	0.60840 (2)	0.21087 (1)	0.46018 (2)	0.0185 (1)
I2	0.12463 (2)	0.42060 (1)	0.36116 (2)	0.0221 (1)
H2	0.52290	0.52130	0.20080	0.0210*
H3	0.38690	0.59030	0.07280	0.0230*
H4	0.15300	0.57390	−0.09700	0.0220*
H5	0.04220	0.48660	−0.14790	0.0210*
H7	0.31670	0.33970	0.11070	0.0190*
H8A	0.53420	0.42770	0.32720	0.0230*
H8B	0.67830	0.42190	0.25380	0.0230*
H9A	0.69280	0.34690	0.37440	0.0440*
H9B	0.62780	0.32910	0.24150	0.0440*
H9C	0.48340	0.33490	0.31460	0.0440*
H10A	−0.06950	0.38710	−0.10730	0.0210*
H10B	0.02540	0.33290	−0.05420	0.0210*
H11A	0.12410	0.39260	−0.23330	0.0190*
H11B	0.22680	0.34000	−0.17780	0.0190*
H12A	−0.06920	0.26670	−0.17760	0.0220*
H12B	−0.14380	0.24920	−0.31040	0.0220*
H13A	0.23390	0.25060	−0.18190	0.0250*
H13B	0.11650	0.19830	−0.22080	0.0250*
H14A	0.25250	0.28860	−0.45720	0.0250*
H14B	0.31290	0.30480	−0.32290	0.0250*
H15A	−0.05680	0.30680	−0.46720	0.0230*
H15B	0.06330	0.35840	−0.42590	0.0230*
H16A	−0.30120	0.32540	−0.38710	0.0250*
H16B	−0.27100	0.34440	−0.25620	0.0250*
H17A	−0.36600	0.41660	−0.38410	0.0390*
H17B	−0.19580	0.40870	−0.43480	0.0390*
H17C	−0.16570	0.42780	−0.30370	0.0390*
H2A	0.173 (6)	0.4568 (15)	0.573 (4)	0.042 (11)*
H2B	0.108 (8)	0.491 (2)	0.632 (6)	0.087 (19)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0326 (11)	0.0129 (8)	0.0285 (12)	0.0035 (7)	0.0110 (9)	−0.0032 (8)
N1	0.0189 (10)	0.0116 (8)	0.0164 (12)	−0.0003 (7)	0.0049 (9)	0.0002 (8)
N2	0.0189 (10)	0.0113 (9)	0.0174 (11)	−0.0026 (8)	0.0056 (9)	−0.0029 (8)
N3	0.0188 (10)	0.0126 (9)	0.0159 (11)	−0.0014 (7)	0.0041 (9)	−0.0003 (8)
C1	0.0175 (12)	0.0136 (10)	0.0184 (13)	0.0002 (9)	0.0088 (10)	0.0008 (9)
C2	0.0186 (12)	0.0150 (10)	0.0208 (14)	−0.0012 (9)	0.0081 (11)	−0.0019 (10)
C3	0.0246 (13)	0.0129 (10)	0.0253 (15)	−0.0003 (9)	0.0139 (12)	−0.0010 (10)
C4	0.0215 (12)	0.0156 (11)	0.0209 (14)	0.0043 (9)	0.0117 (11)	0.0014 (10)
C5	0.0168 (11)	0.0191 (11)	0.0172 (13)	0.0010 (9)	0.0078 (10)	0.0000 (10)
C6	0.0173 (11)	0.0131 (10)	0.0181 (13)	−0.0013 (9)	0.0095 (10)	−0.0011 (9)
C7	0.0183 (12)	0.0120 (10)	0.0200 (14)	−0.0007 (9)	0.0090 (10)	−0.0004 (9)
C8	0.0192 (12)	0.0178 (11)	0.0180 (14)	−0.0015 (9)	0.0026 (11)	0.0004 (10)
C9	0.0364 (16)	0.0202 (12)	0.0241 (16)	0.0029 (11)	−0.0042 (13)	0.0042 (11)
C10	0.0172 (12)	0.0174 (10)	0.0185 (14)	−0.0040 (9)	0.0060 (10)	−0.0044 (10)
C11	0.0176 (12)	0.0125 (10)	0.0178 (13)	0.0006 (8)	0.0062 (10)	0.0003 (9)
C12	0.0243 (13)	0.0115 (10)	0.0188 (14)	−0.0040 (9)	0.0047 (11)	0.0001 (9)
C13	0.0235 (13)	0.0124 (10)	0.0257 (15)	0.0011 (9)	0.0041 (11)	0.0010 (10)
C14	0.0233 (13)	0.0167 (11)	0.0250 (15)	−0.0012 (9)	0.0097 (12)	−0.0023 (10)
C15	0.0267 (13)	0.0177 (11)	0.0143 (13)	0.0006 (10)	0.0065 (11)	0.0007 (10)
C16	0.0153 (12)	0.0209 (12)	0.0241 (15)	0.0017 (9)	0.0022 (10)	−0.0028 (11)
C17	0.0246 (14)	0.0222 (12)	0.0286 (17)	0.0048 (10)	0.0023 (12)	−0.0018 (11)
O2	0.0370 (12)	0.0245 (9)	0.0221 (12)	0.0004 (9)	0.0052 (10)	−0.0004 (8)
I1	0.0195 (1)	0.0135 (1)	0.0219 (1)	−0.0004 (1)	0.0046 (1)	−0.0012 (1)
I2	0.0263 (1)	0.0202 (1)	0.0217 (1)	0.0017 (1)	0.0099 (1)	0.0008 (1)

Geometric parameters (Å, º)

O1—C13	1.430 (4)	C3—H3	0.9300
O1—C14	1.431 (3)	C4—H4	0.9300
O2—H2B	0.83 (6)	C5—H5	0.9300
O2—H2A	0.94 (4)	C7—H7	0.9300
N1—C7	1.323 (3)	C8—H8B	0.9700
N1—C1	1.398 (3)	C8—H8A	0.9700
N1—C8	1.464 (4)	C9—H9B	0.9600
N2—C10	1.467 (4)	C9—H9A	0.9600
N2—C7	1.332 (3)	C9—H9C	0.9600
N2—C6	1.403 (3)	C10—H10B	0.9700
N3—C11	1.519 (3)	C10—H10A	0.9700
N3—C16	1.529 (4)	C11—H11B	0.9700
N3—C12	1.527 (3)	C11—H11A	0.9700
N3—C15	1.519 (4)	C12—H12B	0.9700
C1—C6	1.378 (3)	C12—H12A	0.9700
C1—C2	1.397 (3)	C13—H13A	0.9700
C2—C3	1.381 (4)	C13—H13B	0.9700
C3—C4	1.404 (4)	C14—H14B	0.9700
C4—C5	1.396 (3)	C14—H14A	0.9700
C5—C6	1.391 (3)	C15—H15B	0.9700
C8—C9	1.510 (4)	C15—H15A	0.9700
C10—C11	1.524 (4)	C16—H16B	0.9700
C12—C13	1.515 (4)	C16—H16A	0.9700
C14—C15	1.516 (4)	C17—H17C	0.9600
C16—C17	1.519 (4)	C17—H17A	0.9600
C2—H2	0.9300	C17—H17B	0.9600
I1···C7^i	3.751 (3)	C17···H10A	2.9900
I2···C8	3.799 (4)	C17···H11A	2.7700
I2···O2	3.517 (3)	C17···H15B	2.8200
I2···N1	3.696 (3)	H2···C8	2.9300
I2···O2^ii	3.631 (3)	H2···O2^x	2.4000
I1···H11B^i	3.1500	H2A···I2	2.58 (4)
I1···H12A^iii	3.3200	H2A···H15B^vii	2.5900
I1···H16B^iii	3.2300	H2B···I2^ii	2.83 (6)
I1···H12B^iv	2.9800	H3···I1^xiii	3.0300
I1···H13A^i	3.0100	H3···H10A^viii	2.5900
I1···H3^v	3.0300	H4···I2^viii	3.2300
I1···H10B^iii	3.3700	H4···H8B^xi	2.5100
I1···H16A^iv	3.3400	H5···O2^xii	2.8900
I2···H8A	3.2200	H5···C10	3.0500
I2···H8B^vi	3.2500	H5···H17C	2.5200
I2···H13B^i	3.1100	H7···C9	2.6300
I2···H15B^vii	3.0800	H7···H9B	2.4400
I2···H2A	2.58 (4)	H7···H9C	2.3800
I2···H2B^ii	2.83 (6)	H7···H10B	2.5000
I2···H4^viii	3.2300	H7···O1^i	2.2200
O1···N3	2.922 (4)	H7···C13^i	3.1000
O1···C7^ix	3.059 (4)	H8A···I2	3.2200
O2···C5^vii	3.348 (4)	H8A···C2	3.0900
O2···C11^vii	3.366 (4)	H8B···I2^xiv	3.2500
O2···I2	3.517 (3)	H8B···C2	3.0700
O2···C2^x	3.307 (5)	H8B···C4^xi	2.9100
O2···I2^ii	3.631 (3)	H8B···H4^xi	2.5100
O1···H7^ix	2.2200	H9A···H15A^iv	2.4700
O1···H10B^ix	2.8800	H9B···C7	2.8100
O2···H2^x	2.4000	H9B···H7	2.4400
O2···H11A^vii	2.4100	H9C···C7	2.7800
O2···H5^vii	2.8900	H9C···H7	2.3800
N1···I2	3.696 (3)	H9C···C13^i	3.0700
N1···N2	2.183 (4)	H10A···H17C	2.4400
N2···N1	2.183 (4)	H10A···C5	3.0400
N3···O1	2.922 (4)	H10A···C16	2.6900
C1···C4^xi	3.488 (4)	H10A···C17	2.9900
C1···C3^xi	3.243 (5)	H10A···H16B	2.2400
C1···C2^xi	3.539 (5)	H10A···H3^viii	2.5900
C2···C3^xi	3.574 (5)	H10A···C3^viii	2.7400
C2···C4^xi	3.512 (5)	H10A···C4^viii	2.8700
C2···C5^xi	3.497 (5)	H10B···O1^i	2.8800
C2···C6^xi	3.498 (5)	H10B···C12	2.8000
C2···O2^x	3.307 (5)	H10B···H7	2.5000
C2···C1^xi	3.539 (5)	H10B···H12A	2.1800
C3···C1^xi	3.243 (5)	H10B···I1^xv	3.3700
C3···C6^xi	3.500 (5)	H11A···C6	3.0200
C3···C2^xi	3.574 (5)	H11A···O2^xii	2.4100
C4···C2^xi	3.512 (5)	H11A···C5	3.0800
C4···C1^xi	3.488 (4)	H11A···H17C	2.2800
C4···C10^viii	3.536 (4)	H11A···C17	2.7700
C4···C5^viii	3.444 (5)	H11A···H15B	2.3400
C4···C6^viii	3.395 (4)	H11B···C13	2.7600
C5···C5^viii	3.152 (5)	H11B···H14B	2.1700
C5···C6^viii	3.356 (4)	H11B···C14	2.7200
C5···O2^xii	3.348 (4)	H11B···H13A	2.2300
C5···C2^xi	3.497 (5)	H11B···I1^ix	3.1500
C5···C4^viii	3.444 (5)	H12A···I1^xv	3.3200
C6···C4^viii	3.395 (4)	H12A···C10	2.7600
C6···C5^viii	3.356 (4)	H12A···H10B	2.1800
C6···C2^xi	3.498 (5)	H12A···H16B	2.4800
C6···C3^xi	3.500 (5)	H12B···H15A	2.5600
C7···O1^i	3.059 (4)	H12B···I1^xvi	2.9800
C7···I1^ix	3.751 (3)	H12B···H16A	2.2900
C8···I2	3.799 (4)	H13A···C11	2.8200
C10···C17	3.507 (5)	H13A···H11B	2.2300
C10···C4^viii	3.536 (4)	H13A···H14B	2.3400
C11···O2^xii	3.366 (4)	H13A···I1^ix	3.0100
C17···C10	3.507 (5)	H13B···I2^ix	3.1100
C2···H8B	3.0700	H14B···C11	2.7300
C2···H8A	3.0900	H14B···H11B	2.1700
C3···H10A^viii	2.7400	H14B···H13A	2.3400
C4···H10A^viii	2.8700	H15A···H9A^xvi	2.4700
C4···H8B^xi	2.9100	H15A···H12B	2.5600
C5···H11A	3.0800	H15A···H16A	2.3300
C5···H10A	3.0400	H15B···I2^xii	3.0800
C6···H11A	3.0200	H15B···C17	2.8200
C7···H9C	2.7800	H15B···H2A^xii	2.5900
C7···H9B	2.8100	H15B···H11A	2.3400
C8···H2	2.9300	H15B···H17B	2.3000
C9···H7	2.6300	H16A···I1^xvi	3.3400
C10···H16B	2.7000	H16A···H12B	2.2900
C10···H5	3.0500	H16A···H15A	2.3300
C10···H12A	2.7600	H16B···C10	2.7000
C10···H17C	3.0000	H16B···H10A	2.2400
C11···H13A	2.8200	H16B···H12A	2.4800
C11···H14B	2.7300	H16B···I1^xv	3.2300
C11···H17C	2.7100	H17B···C15	2.7500
C12···H10B	2.8000	H17B···H15B	2.3000
C13···H9C^ix	3.0700	H17C···C10	3.0000
C13···H11B	2.7600	H17C···C11	2.7100
C13···H7^ix	3.1000	H17C···H5	2.5200
C14···H11B	2.7200	H17C···H10A	2.4400
C15···H17B	2.7500	H17C···H11A	2.2800
C16···H10A	2.6900
C13—O1—C14	110.1 (2)	C8—C9—H9A	109.00
H2A—O2—H2B	92 (5)	C8—C9—H9C	109.00
C1—N1—C8	124.29 (19)	H9A—C9—H9B	109.00
C7—N1—C8	128.03 (19)	H9A—C9—H9C	109.00
C1—N1—C7	107.7 (2)	H9B—C9—H9C	110.00
C6—N2—C7	108.3 (2)	C8—C9—H9B	109.00
C6—N2—C10	127.0 (2)	N2—C10—H10B	110.00
C7—N2—C10	124.6 (2)	C11—C10—H10A	110.00
C11—N3—C12	112.90 (19)	N2—C10—H10A	110.00
C11—N3—C15	109.0 (2)	H10A—C10—H10B	108.00
C12—N3—C15	106.70 (18)	C11—C10—H10B	110.00
C12—N3—C16	106.1 (2)	N3—C11—H11A	109.00
C15—N3—C16	109.2 (2)	N3—C11—H11B	109.00
C11—N3—C16	112.66 (19)	C10—C11—H11B	109.00
N1—C1—C6	107.6 (2)	H11A—C11—H11B	108.00
C2—C1—C6	122.6 (2)	C10—C11—H11A	109.00
N1—C1—C2	129.8 (2)	N3—C12—H12B	109.00
C1—C2—C3	115.3 (3)	C13—C12—H12A	109.00
C2—C3—C4	122.4 (2)	C13—C12—H12B	109.00
C3—C4—C5	121.8 (2)	H12A—C12—H12B	108.00
C4—C5—C6	115.3 (2)	N3—C12—H12A	109.00
N2—C6—C1	105.8 (2)	O1—C13—H13A	109.00
C1—C6—C5	122.6 (2)	C12—C13—H13A	110.00
N2—C6—C5	131.7 (2)	C12—C13—H13B	109.00
N1—C7—N2	110.6 (2)	O1—C13—H13B	109.00
N1—C8—C9	112.2 (2)	H13A—C13—H13B	108.00
N2—C10—C11	108.9 (2)	O1—C14—H14B	110.00
N3—C11—C10	113.5 (2)	C15—C14—H14A	110.00
N3—C12—C13	112.4 (2)	O1—C14—H14A	110.00
O1—C13—C12	110.9 (2)	H14A—C14—H14B	108.00
O1—C14—C15	109.9 (2)	C15—C14—H14B	110.00
N3—C15—C14	112.3 (2)	N3—C15—H15A	109.00
N3—C16—C17	114.6 (2)	C14—C15—H15A	109.00
C3—C2—H2	122.00	C14—C15—H15B	109.00
C1—C2—H2	122.00	H15A—C15—H15B	108.00
C4—C3—H3	119.00	N3—C15—H15B	109.00
C2—C3—H3	119.00	N3—C16—H16A	109.00
C3—C4—H4	119.00	C17—C16—H16A	109.00
C5—C4—H4	119.00	C17—C16—H16B	109.00
C6—C5—H5	122.00	N3—C16—H16B	109.00
C4—C5—H5	122.00	H16A—C16—H16B	108.00
N1—C7—H7	125.00	C16—C17—H17B	109.00
N2—C7—H7	125.00	C16—C17—H17C	109.00
N1—C8—H8B	109.00	C16—C17—H17A	109.00
C9—C8—H8A	109.00	H17A—C17—H17C	110.00
N1—C8—H8A	109.00	H17B—C17—H17C	110.00
H8A—C8—H8B	108.00	H17A—C17—H17B	109.00
C9—C8—H8B	109.00
C14—O1—C13—C12	61.5 (3)	C12—N3—C16—C17	179.6 (2)
C13—O1—C14—C15	−62.3 (3)	C16—N3—C11—C10	53.8 (3)
C7—N1—C1—C6	−1.1 (3)	C16—N3—C15—C14	−167.2 (2)
C8—N1—C1—C2	−0.5 (4)	C15—N3—C11—C10	175.14 (19)
C1—N1—C8—C9	−178.7 (2)	C16—N3—C12—C13	168.0 (2)
C8—N1—C1—C6	179.8 (2)	C15—N3—C16—C17	−65.7 (3)
C8—N1—C7—N2	179.7 (3)	C15—N3—C12—C13	51.6 (3)
C7—N1—C8—C9	2.4 (4)	C11—N3—C12—C13	−68.1 (3)
C1—N1—C7—N2	0.7 (3)	C2—C1—C6—N2	−178.7 (2)
C7—N1—C1—C2	178.6 (3)	N1—C1—C2—C3	178.8 (3)
C7—N2—C10—C11	−102.9 (3)	N1—C1—C6—C5	−178.2 (2)
C10—N2—C7—N1	−177.3 (2)	C6—C1—C2—C3	−1.6 (4)
C6—N2—C10—C11	80.4 (3)	C2—C1—C6—C5	2.1 (4)
C7—N2—C6—C5	178.5 (3)	N1—C1—C6—N2	1.0 (3)
C10—N2—C6—C5	−4.4 (4)	C1—C2—C3—C4	0.5 (5)
C10—N2—C6—C1	176.5 (2)	C2—C3—C4—C5	0.2 (5)
C6—N2—C7—N1	0.0 (3)	C3—C4—C5—C6	0.2 (4)
C7—N2—C6—C1	−0.7 (3)	C4—C5—C6—N2	179.7 (3)
C11—N3—C15—C14	69.3 (2)	C4—C5—C6—C1	−1.3 (4)
C12—N3—C15—C14	−52.9 (3)	N2—C10—C11—N3	177.39 (18)
C12—N3—C11—C10	−66.5 (3)	N3—C12—C13—O1	−57.3 (3)
C11—N3—C16—C17	55.6 (3)	O1—C14—C15—N3	59.7 (3)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x, −y+1, −z+1; (iii) x+1, −y+1/2, z+1/2; (iv) x+1, y, z+1; (v) −x+1, y−1/2, −z+1/2; (vi) x−1, y, z; (vii) x, y, z+1; (viii) −x, −y+1, −z; (ix) x, −y+1/2, z−1/2; (x) −x+1, −y+1, −z+1; (xi) −x+1, −y+1, −z; (xii) x, y, z−1; (xiii) −x+1, y+1/2, −z+1/2; (xiv) x+1, y, z; (xv) x−1, −y+1/2, z−1/2; (xvi) x−1, y, z−1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···I2	0.94 (4)	2.58 (4)	3.517 (3)	175 (4)
O2—H2B···I2^ii	0.83 (6)	2.83 (6)	3.631 (3)	162 (6)
C2—H2···O2^x	0.93	2.40	3.307 (5)	166
C3—H3···I1^xiii	0.93	3.03	3.899 (3)	157
C7—H7···O1^i	0.93	2.22	3.059 (4)	149
C11—H11A···O2^xii	0.97	2.41	3.366 (4)	168
C12—H12B···I1^xvi	0.97	2.98	3.911 (4)	161
C13—H13A···I1^ix	0.97	3.01	3.949 (4)	163

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x, −y+1, −z+1; (ix) x, −y+1/2, z−1/2; (x) −x+1, −y+1, −z+1; (xii) x, y, z−1; (xiii) −x+1, y+1/2, −z+1/2; (xvi) x−1, y, z−1.