N-Methyl-N'-(3-phthalimido­propyl)-4,4'-bipyridinium diiodide

The asymmetric unit of the title compound, C₂₂H₂₁N₃O₂²⁺·2I^-, consists of a substituted bipyridinium cation and two iodide anions. The dihedral angle between the two rings within the phthal­imide moiety is 1.7 (3)°, where the r.m.s. deviations for the five- and six-membered rings are 0.006 and 0.004 Å, respectively. On the other hand, the two pyridinium rings are tilted at an angle of 3.9 (3)° because of the steric contacts between the H atoms at the 3-, 5-, 3'- and 5'-positions of the 4,4'-bipyridinium moiety. The phthal­imide plane is tilted by 68.5 (1)° with respect to the pyridinium plane, directly attached to the propyl­ene moiety.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.041
• wR factor = 0.102
• Data-to-parameter ratio = 18.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.50
         From the CIF: _reflns_number_total               4883
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         5280
         Completeness (_total/calc)             92.48%
          Alert C: < 95% complete


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

S1. Comment

A photochemical system made up of Ru(bpy)₃²⁺ (bpy = 2,2'-bipyridine) and methylviologen (usually, N,N'-dimethyl-4,4'-bipyridinium dichloride) has been thought of as one of the promising candidates to achieve artificial photosynthetic devices. We previously reported that some amidate-bridged platinum dimers with the general formula of [Pt₂(NH₃)₄(µ-amidato)₂]²⁺ (amidate = acetamidate, α-pyrrolidinonate, α-pyridonate, etc.) serve as an effective H₂-producing catalyst in a well known photosystem consisting of edta, Ru(bpy)₃²⁺ and methylviologen (Sakai et al., 1993). Since then, various efforts have been made to develop a more effective system in which the chemical species mentioned above are linked together to give a single molecular device. The title compound, (I), is obtained as a precursor in such studies.

The molecular structure and the crystal packing diagram for (I) are shown in Figs. 1 and 2, respectively. All bond distances and angles in (I) are observed as expected.

S2. Experimental

A solution of N-methyl-4,4'-bipyridinium iodide (1.0 mmol; Van Emon et al., 1986) and N-(3-bromopropyl)phthalimide (1.1 mmol) in methanol (20 ml) was refluxed for 2 d. The red prisms or plates deposited were collected by filtration and air-dried (yield: 52%). The purity has been checked by ¹H NMR spectroscopy.

S3. Refinement

All H atoms were located at their idealized positions as riding atoms [C—H(aromatic) = 0.93 Å, C—H(methylene) = 0.97 Å and C—H(methyl) = 0.96 Å]. In the final difference Fourier synthesis, five residual peaks in the range 1.01–1.27 e Å⁻³ were observed within 0.94 Å of I atoms.

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: KENX (Sakai, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997), TEXSAN (Molecular Structure Corporation, 2001), KENX (Sakai, 2002) and ORTEPII (Johnson, 1976).

Figures

	Fig. 1. The structure of the independent cation and anions in (I), showing the atom-labeling scheme. Displacement ellipsoids are shown at the 50% probability level.
	Fig. 2. Crystal packing view down the a axis of (I).

N-Methyl-N'-(3-phthalimidopropyl)-4,4'-bipyridinium diiodide

Crystal data

C22H21N3O2^2+·2I^−	Z = 2
Mr = 613.22	F(000) = 592
Triclinic, P1	? # Insert any comments here.
Hall symbol: -P 1	Dx = 1.775 Mg m^−3
a = 6.0535 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.4674 (6) Å	Cell parameters from 3414 reflections
c = 25.776 (2) Å	θ = 2.8–27.2°
α = 83.715 (1)°	µ = 2.76 mm^−1
β = 88.570 (2)°	T = 296 K
γ = 82.223 (1)°	Plate, red
V = 1147.45 (16) Å^3	0.20 × 0.20 × 0.05 mm

Data collection

Bruker SMART APEX CCD-detector diffractometer	4883 independent reflections
Radiation source: fine-focus sealed tube	4060 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 8.366 pixels mm^-1	θmax = 27.5°, θmin = 2.4°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −8→9
Tmin = 0.586, Tmax = 0.871	l = −24→33
6983 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.102	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.048P)^2 + 0.5905P] where P = (Fo^2 + 2Fc^2)/3
4883 reflections	(Δ/σ)max = 0.001
263 parameters	Δρmax = 1.27 e Å^−3
0 restraints	Δρmin = −0.44 e Å^−3

Special details

Experimental. The first 50 frames were rescanned at the end of data collection to evaluate any possible decay phenomenon. Since it was judged to be negligible, no decay correction was applied to the data.

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

− 3.2752 (0.0107) x − 3.4850 (0.0128) y + 17.5481 (0.0380) z = 5.2837 (0.0195)

* 0.0038 (0.0025) N1 * 0.0018 (0.0025) C1 * −0.0069 (0.0026) C2 * 0.0091 (0.0026) C7 * −0.0077 (0.0024) C8 0.0319 (0.0065) O1 − 0.0086 (0.0065) O2

Rms deviation of fitted atoms = 0.0064

− 3.1971 (0.0099) x − 3.6691 (0.0124) y + 17.3429 (0.0361) z = 5.1130 (0.0218)

Angle to previous plane (with approximate e.s.d.) = 1.72 (0.31)

* −0.0021 (0.0030) C2 * −0.0016 (0.0032) C3 * 0.0056 (0.0034) C4 * −0.0057 (0.0036) C5 * 0.0019 (0.0034) C6 * 0.0019 (0.0030) C7 0.1042 (0.0082) O1 0.0235 (0.0081) O2

Rms deviation of fitted atoms = 0.0036

− 3.2327 (0.0078) x − 3.5891 (0.0060) y + 17.4312 (0.0251) z = 5.2054 (0.0128)

Angle to previous plane (with approximate e.s.d.) = 0.76 (0.26)

* 0.0199 (0.0029) N1 * 0.0107 (0.0032) C1 * −0.0231 (0.0037) C2 * −0.0109 (0.0035) C3 * 0.0142 (0.0038) C4 * 0.0084 (0.0041) C5 * 0.0040 (0.0038) C6 * −0.0135 (0.0037) C7 * −0.0097 (0.0032) C8 0.0534 (0.0055) O1 − 0.0088 (0.0055) O2

Rms deviation of fitted atoms = 0.0138

3.5617 (0.0072) x − 1.9039 (0.0123) y + 18.2690 (0.0275) z = 6.0355 (0.0080)

Angle to previous plane (with approximate e.s.d.) = 68.45 (0.10)

* 0.0053 (0.0025) N2 * 0.0009 (0.0026) C12 * −0.0071 (0.0028) C13 * 0.0073 (0.0026) C14 * −0.0014 (0.0027) C15 * −0.0049 (0.0028) C16

Rms deviation of fitted atoms = 0.0051

3.5183 (0.0076) x − 2.3694 (0.0130) y + 17.4322 (0.0308) z = 5.8040 (0.0118)

Angle to previous plane (with approximate e.s.d.) = 3.87 (1/4)

* −0.0065 (0.0026) N3 * −0.0017 (0.0030) C17 * 0.0093 (0.0030) C18 * −0.0089 (0.0027) C19 * 0.0011 (0.0027) C20 * 0.0067 (0.0027) C21

Rms deviation of fitted atoms = 0.0065

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
I1	0.19500 (5)	0.72933 (4)	0.254201 (15)	0.06628 (13)
I2	0.84565 (5)	0.74396 (4)	0.065322 (12)	0.05327 (11)
O1	0.4876 (5)	0.2479 (5)	0.44316 (13)	0.0672 (9)
O2	−0.1257 (6)	0.3202 (5)	0.34073 (14)	0.0749 (10)
N1	0.1978 (6)	0.2446 (5)	0.38681 (13)	0.0492 (8)
N2	0.5727 (5)	0.2105 (4)	0.24093 (12)	0.0377 (7)
N3	1.4807 (5)	0.2657 (4)	0.06983 (12)	0.0398 (7)
C1	0.3138 (7)	0.3200 (6)	0.42332 (16)	0.0499 (10)
C2	0.1766 (7)	0.4947 (6)	0.43191 (16)	0.0489 (10)
C3	0.2117 (8)	0.6203 (6)	0.46498 (18)	0.0586 (11)
H3	0.3390	0.6064	0.4853	0.070*
C4	0.0484 (10)	0.7685 (7)	0.4666 (2)	0.0697 (14)
H4	0.0648	0.8558	0.4889	0.084*
C5	−0.1378 (10)	0.7887 (8)	0.4359 (2)	0.0776 (16)
H5	−0.2434	0.8909	0.4373	0.093*
C6	−0.1721 (9)	0.6599 (8)	0.4028 (2)	0.0715 (14)
H6	−0.2990	0.6727	0.3824	0.086*
C7	−0.0104 (7)	0.5141 (6)	0.40176 (17)	0.0527 (10)
C8	0.0021 (7)	0.3550 (7)	0.37156 (17)	0.0552 (11)
C9	0.2768 (8)	0.0703 (6)	0.36789 (16)	0.0530 (11)
H9A	0.1530	0.0257	0.3525	0.064*
H9B	0.3287	−0.0163	0.3973	0.064*
C10	0.4626 (7)	0.0793 (5)	0.32801 (15)	0.0465 (9)
H10A	0.5837	0.1301	0.3425	0.056*
H10B	0.5191	−0.0427	0.3201	0.056*
C11	0.3849 (6)	0.1939 (5)	0.27838 (15)	0.0434 (9)
H11A	0.2703	0.1391	0.2626	0.052*
H11B	0.3203	0.3139	0.2864	0.052*
C12	0.6752 (7)	0.3591 (5)	0.23621 (15)	0.0433 (9)
H12	0.6250	0.4538	0.2560	0.052*
C13	0.8524 (6)	0.3747 (5)	0.20284 (16)	0.0420 (9)
H13	0.9205	0.4798	0.1997	0.050*
C14	0.9306 (6)	0.2327 (5)	0.17358 (14)	0.0345 (7)
C15	0.8192 (6)	0.0811 (5)	0.17903 (15)	0.0420 (9)
H15	0.8659	−0.0154	0.1597	0.050*
C16	0.6415 (7)	0.0722 (5)	0.21254 (16)	0.0453 (9)
H16	0.5679	−0.0300	0.2157	0.054*
C17	1.3702 (7)	0.1209 (6)	0.07274 (17)	0.0503 (10)
H17	1.4133	0.0294	0.0514	0.060*
C18	1.1957 (7)	0.1061 (5)	0.10658 (17)	0.0478 (10)
H18	1.1224	0.0037	0.1086	0.057*
C19	1.1264 (6)	0.2432 (5)	0.13816 (14)	0.0361 (8)
C20	1.2465 (7)	0.3901 (5)	0.13447 (15)	0.0425 (9)
H20	1.2072	0.4838	0.1553	0.051*
C21	1.4225 (6)	0.3974 (5)	0.10025 (15)	0.0417 (9)
H21	1.5025	0.4958	0.0983	0.050*
C22	1.6680 (7)	0.2759 (6)	0.03166 (17)	0.0495 (10)
H22A	1.6097	0.3005	−0.0031	0.074*
H22B	1.7645	0.1622	0.0347	0.074*
H22C	1.7506	0.3714	0.0387	0.074*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0654 (2)	0.03703 (17)	0.1002 (3)	−0.01153 (14)	−0.01225 (18)	−0.01576 (15)
I2	0.05358 (18)	0.03899 (16)	0.0708 (2)	−0.01621 (12)	−0.00222 (14)	−0.00893 (13)
O1	0.062 (2)	0.074 (2)	0.066 (2)	0.0056 (17)	−0.0165 (17)	−0.0240 (17)
O2	0.066 (2)	0.090 (3)	0.075 (2)	−0.0285 (19)	−0.0166 (18)	−0.0111 (19)
N1	0.052 (2)	0.056 (2)	0.0440 (19)	−0.0184 (17)	−0.0002 (16)	−0.0115 (16)
N2	0.0386 (16)	0.0334 (16)	0.0407 (17)	−0.0050 (13)	0.0008 (13)	−0.0016 (13)
N3	0.0373 (16)	0.0357 (16)	0.0467 (18)	−0.0064 (13)	−0.0003 (14)	−0.0041 (13)
C1	0.054 (2)	0.058 (3)	0.041 (2)	−0.014 (2)	0.0009 (19)	−0.0103 (18)
C2	0.053 (2)	0.051 (2)	0.043 (2)	−0.0112 (19)	0.0062 (19)	−0.0053 (18)
C3	0.068 (3)	0.054 (3)	0.055 (3)	−0.009 (2)	0.003 (2)	−0.010 (2)
C4	0.094 (4)	0.051 (3)	0.063 (3)	−0.009 (3)	0.011 (3)	−0.007 (2)
C5	0.081 (4)	0.064 (3)	0.080 (4)	0.006 (3)	0.019 (3)	0.004 (3)
C6	0.062 (3)	0.081 (4)	0.065 (3)	−0.003 (3)	−0.002 (2)	0.011 (3)
C7	0.051 (2)	0.057 (3)	0.050 (2)	−0.011 (2)	0.0036 (19)	0.002 (2)
C8	0.052 (3)	0.070 (3)	0.047 (2)	−0.025 (2)	0.000 (2)	−0.001 (2)
C9	0.068 (3)	0.052 (2)	0.044 (2)	−0.026 (2)	0.001 (2)	−0.0043 (18)
C10	0.052 (2)	0.041 (2)	0.049 (2)	−0.0124 (18)	−0.0018 (19)	−0.0051 (17)
C11	0.043 (2)	0.040 (2)	0.048 (2)	−0.0071 (17)	0.0019 (17)	−0.0038 (16)
C12	0.049 (2)	0.037 (2)	0.045 (2)	−0.0068 (17)	−0.0011 (18)	−0.0115 (16)
C13	0.042 (2)	0.0325 (18)	0.055 (2)	−0.0131 (16)	0.0019 (17)	−0.0110 (16)
C14	0.0359 (18)	0.0293 (17)	0.0384 (19)	−0.0046 (14)	−0.0029 (15)	−0.0033 (14)
C15	0.046 (2)	0.0301 (18)	0.050 (2)	−0.0065 (16)	0.0041 (18)	−0.0079 (16)
C16	0.054 (2)	0.0302 (18)	0.053 (2)	−0.0114 (17)	0.0057 (19)	−0.0052 (16)
C17	0.047 (2)	0.045 (2)	0.065 (3)	−0.0169 (18)	0.009 (2)	−0.0222 (19)
C18	0.049 (2)	0.039 (2)	0.062 (3)	−0.0173 (18)	0.007 (2)	−0.0207 (18)
C19	0.0368 (18)	0.0293 (17)	0.042 (2)	−0.0052 (14)	−0.0060 (15)	−0.0023 (14)
C20	0.051 (2)	0.0305 (18)	0.048 (2)	−0.0105 (16)	0.0002 (18)	−0.0067 (15)
C21	0.046 (2)	0.0293 (18)	0.051 (2)	−0.0118 (16)	−0.0008 (18)	−0.0027 (16)
C22	0.045 (2)	0.048 (2)	0.057 (3)	−0.0128 (18)	0.0096 (19)	−0.0081 (19)

Geometric parameters (Å, º)

O1—C1	1.213 (5)	C10—C11	1.507 (5)
O2—C8	1.195 (5)	C10—H10A	0.9700
N1—C8	1.387 (6)	C10—H10B	0.9700
N1—C1	1.397 (5)	C11—H11A	0.9700
N1—C9	1.456 (5)	C11—H11B	0.9700
N2—C12	1.336 (5)	C12—C13	1.367 (5)
N2—C16	1.345 (5)	C12—H12	0.9300
N2—C11	1.482 (5)	C13—C14	1.392 (5)
N3—C21	1.329 (5)	C13—H13	0.9300
N3—C17	1.341 (5)	C14—C15	1.386 (5)
N3—C22	1.486 (5)	C14—C19	1.483 (5)
C1—C2	1.483 (6)	C15—C16	1.367 (5)
C2—C7	1.372 (6)	C15—H15	0.9300
C2—C3	1.375 (6)	C16—H16	0.9300
C3—C4	1.384 (7)	C17—C18	1.362 (6)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.375 (8)	C18—C19	1.392 (5)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.393 (8)	C19—C20	1.389 (5)
C5—H5	0.9300	C20—C21	1.369 (5)
C6—C7	1.364 (7)	C20—H20	0.9300
C6—H6	0.9300	C21—H21	0.9300
C7—C8	1.483 (6)	C22—H22A	0.9600
C9—C10	1.508 (5)	C22—H22B	0.9600
C9—H9A	0.9700	C22—H22C	0.9600
C9—H9B	0.9700
C8—N1—C1	111.9 (4)	H10A—C10—H10B	107.9
C8—N1—C9	125.2 (4)	N2—C11—C10	110.9 (3)
C1—N1—C9	122.9 (4)	N2—C11—H11A	109.5
C12—N2—C16	120.5 (3)	C10—C11—H11A	109.5
C12—N2—C11	120.5 (3)	N2—C11—H11B	109.5
C16—N2—C11	119.1 (3)	C10—C11—H11B	109.5
C21—N3—C17	120.5 (3)	H11A—C11—H11B	108.0
C21—N3—C22	121.0 (3)	N2—C12—C13	121.2 (3)
C17—N3—C22	118.5 (3)	N2—C12—H12	119.4
O1—C1—N1	124.3 (4)	C13—C12—H12	119.4
O1—C1—C2	130.2 (4)	C12—C13—C14	119.8 (3)
N1—C1—C2	105.5 (4)	C12—C13—H13	120.1
C7—C2—C3	122.1 (5)	C14—C13—H13	120.1
C7—C2—C1	108.4 (4)	C15—C14—C13	117.5 (3)
C3—C2—C1	129.5 (4)	C15—C14—C19	121.4 (3)
C2—C3—C4	116.8 (5)	C13—C14—C19	121.1 (3)
C2—C3—H3	121.6	C16—C15—C14	120.7 (3)
C4—C3—H3	121.6	C16—C15—H15	119.7
C5—C4—C3	121.0 (5)	C14—C15—H15	119.7
C5—C4—H4	119.5	N2—C16—C15	120.3 (3)
C3—C4—H4	119.5	N2—C16—H16	119.8
C4—C5—C6	121.6 (5)	C15—C16—H16	119.8
C4—C5—H5	119.2	N3—C17—C18	120.9 (4)
C6—C5—H5	119.2	N3—C17—H17	119.6
C7—C6—C5	116.7 (5)	C18—C17—H17	119.6
C7—C6—H6	121.7	C17—C18—C19	120.3 (4)
C5—C6—H6	121.7	C17—C18—H18	119.8
C6—C7—C2	121.8 (5)	C19—C18—H18	119.8
C6—C7—C8	129.9 (5)	C20—C19—C18	117.2 (3)
C2—C7—C8	108.3 (4)	C20—C19—C14	121.9 (3)
O2—C8—N1	124.5 (5)	C18—C19—C14	120.9 (3)
O2—C8—C7	129.6 (5)	C21—C20—C19	120.2 (4)
N1—C8—C7	105.8 (4)	C21—C20—H20	119.9
N1—C9—C10	113.5 (3)	C19—C20—H20	119.9
N1—C9—H9A	108.9	N3—C21—C20	121.0 (3)
C10—C9—H9A	108.9	N3—C21—H21	119.5
N1—C9—H9B	108.9	C20—C21—H21	119.5
C10—C9—H9B	108.9	N3—C22—H22A	109.5
H9A—C9—H9B	107.7	N3—C22—H22B	109.5
C11—C10—C9	111.7 (3)	H22A—C22—H22B	109.5
C11—C10—H10A	109.3	N3—C22—H22C	109.5
C9—C10—H10A	109.3	H22A—C22—H22C	109.5
C11—C10—H10B	109.3	H22B—C22—H22C	109.5
C9—C10—H10B	109.3
C8—N1—C1—O1	178.8 (4)	N1—C9—C10—C11	−65.6 (5)
C9—N1—C1—O1	−1.1 (7)	C12—N2—C11—C10	−99.4 (4)
C8—N1—C1—C2	0.2 (5)	C16—N2—C11—C10	79.2 (4)
C9—N1—C1—C2	−179.6 (3)	C9—C10—C11—N2	176.5 (3)
O1—C1—C2—C7	−177.6 (5)	C16—N2—C12—C13	−0.3 (6)
N1—C1—C2—C7	0.8 (5)	C11—N2—C12—C13	178.3 (4)
O1—C1—C2—C3	−0.2 (8)	N2—C12—C13—C14	−0.8 (6)
N1—C1—C2—C3	178.2 (4)	C12—C13—C14—C15	1.4 (6)
C7—C2—C3—C4	0.1 (7)	C12—C13—C14—C19	−178.3 (4)
C1—C2—C3—C4	−177.0 (4)	C13—C14—C15—C16	−0.9 (6)
C2—C3—C4—C5	−0.9 (7)	C19—C14—C15—C16	178.8 (4)
C3—C4—C5—C6	1.3 (8)	C12—N2—C16—C15	0.9 (6)
C4—C5—C6—C7	−0.9 (8)	C11—N2—C16—C15	−177.8 (4)
C5—C6—C7—C2	0.2 (7)	C14—C15—C16—N2	−0.3 (6)
C5—C6—C7—C8	179.4 (4)	C21—N3—C17—C18	0.4 (6)
C3—C2—C7—C6	0.2 (7)	C22—N3—C17—C18	−179.2 (4)
C1—C2—C7—C6	177.9 (4)	N3—C17—C18—C19	1.2 (7)
C3—C2—C7—C8	−179.1 (4)	C17—C18—C19—C20	−1.8 (6)
C1—C2—C7—C8	−1.5 (5)	C17—C18—C19—C14	177.4 (4)
C1—N1—C8—O2	180.0 (4)	C15—C14—C19—C20	−176.5 (3)
C9—N1—C8—O2	−0.2 (7)	C13—C14—C19—C20	3.2 (6)
C1—N1—C8—C7	−1.1 (5)	C15—C14—C19—C18	4.3 (6)
C9—N1—C8—C7	178.7 (3)	C13—C14—C19—C18	−176.0 (4)
C6—C7—C8—O2	1.1 (8)	C18—C19—C20—C21	1.0 (6)
C2—C7—C8—O2	−179.6 (5)	C14—C19—C20—C21	−178.2 (4)
C6—C7—C8—N1	−177.7 (4)	C17—N3—C21—C20	−1.2 (6)
C2—C7—C8—N1	1.6 (5)	C22—N3—C21—C20	178.3 (4)
C8—N1—C9—C10	103.0 (5)	C19—C20—C21—N3	0.5 (6)
C1—N1—C9—C10	−77.2 (5)