(Z)-2,3-Bis(2-phenyl­indolizin-3-yl)-2-butenedi­nitrile

The title compound, C₃₂H₂₀N₄, shows a Z configuration for the two 2-phenyl­indolizin-3-yl substituents. There are two intramolecular π–π interactions. The mol­ecule self-assembles into a three-dimensional framework structure through one intermolecular π–π interaction and two weak intermolecular C—H...N interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.065
• wR factor = 0.137
• Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C9     -   C10    ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C25    -   C26    ...       1.44 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H30A   ..  N3      ..       2.73 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

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

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(Z)-2,3-Bis(2-phenylindozin-3-yl)-2-butenedinitrile

Crystal data

C32H20N4	F(000) = 960
Mr = 460.52	Dx = 1.268 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3716 reflections
a = 11.663 (2) Å	θ = 2.3–22.6°
b = 11.695 (2) Å	µ = 0.08 mm^−1
c = 18.348 (4) Å	T = 293 K
β = 105.38 (3)°	Block, purple
V = 2413.0 (9) Å^3	0.32 × 0.26 × 0.24 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	4719 independent reflections
Radiation source: sealed tube	3207 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
φ and ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −13→13
Tmin = 0.97, Tmax = 0.98	k = −14→12
15789 measured reflections	l = −22→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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.05P)^2 + 0.66P] where P = (Fo^2 + 2Fc^2)/3
4719 reflections	(Δ/σ)max = 0.001
405 parameters	Δρmax = 0.13 e Å^−3
0 restraints	Δρmin = −0.14 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.

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

-2.8305(0.0138)x + 10.8987(0.0080)y + 5.9491(0.0226)z = 6.3129 (0.0187)

* 0.0016 (0.0019) C27 * 0.0037 (0.0021) C28 * -0.0065 (0.0023) C29 * 0.0040 (0.0023) C30 * 0.0014 (0.0024) C31 * -0.0042 (0.0021) C32

Rms deviation of fitted atoms = 0.0040

-7.4026(0.0069)x + 3.9595(0.0100)y + 5.3774(0.0103)z = 13.3962 (0.0103)

Angle to previous plane (with approximate e.s.d.) = 48.95 (0.11)

* 0.0103 (0.0021) C17 * -0.0005 (0.0023) C18 * 0.0056 (0.0024) C19 * 0.0030 (0.0022) C20 * -0.0150 (0.0022) C21 * 0.0074 (0.0020) C22 * 0.0053 (0.0019) C23 * 0.0055 (0.0018) C24 * -0.0216 (0.0018) N2

Rms deviation of fitted atoms = 0.0103

-1.3773(0.0095)x + 10.9620(0.0067)y + 6.3746(0.0142)z = 10.0359 (0.0130)

Angle to previous plane (with approximate e.s.d.) = 51.68 (0.08)

* 0.0075 (0.0021) C1 * -0.0096 (0.0023) C2 * -0.0361 (0.0024) C3 * 0.0080 (0.0023) C4 * 0.0341 (0.0024) C5 * 0.0058 (0.0021) C6 * -0.0380 (0.0018) C7 * -0.0123 (0.0019) C8 * 0.0407 (0.0019) N1

Rms deviation of fitted atoms = 0.0258

-7.0272(0.0121)x + 6.4263(0.0129)y + 13.1718(0.0165)z = 14.9251 (0.0188)

Angle to previous plane (with approximate e.s.d.) = 39.11 (0.11)

* -0.0038 (0.0018) C11 * 0.0047 (0.0021) C12 * -0.0002 (0.0023) C13 * -0.0052 (0.0023) C14 * 0.0060 (0.0021) C15 * -0.0015 (0.0019) C16

Rms deviation of fitted atoms = 0.0041

-7.4026(0.0069)x + 3.9595(0.0100)y + 15.3774(0.0103)z = 13.3962 (0.0103)

Angle to previous plane (with approximate e.s.d.) = 48.95 (0.11)

* 0.0103 (0.0021) C17 * -0.0005 (0.0023) C18 * 0.0056 (0.0024) C19 * 0.0030 (0.0022) C20 * -0.0150 (0.0022) C21 * 0.0074 (0.0020) C22 * 0.0053 (0.0019) C23 * 0.0055 (0.0018) C24 * -0.0216 (0.0018) N2

Rms deviation of fitted atoms = 0.0103

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
N1	0.02927 (17)	0.38190 (16)	0.93035 (12)	0.0427 (5)
N2	0.43934 (17)	0.15133 (16)	1.04229 (11)	0.0411 (5)
N3	0.2596 (2)	0.5812 (2)	0.88642 (15)	0.0738 (8)
N4	0.5312 (2)	0.3902 (2)	0.92705 (15)	0.0708 (8)
C1	−0.0068 (2)	0.4174 (2)	0.85620 (16)	0.0501 (7)
C2	−0.1241 (3)	0.4218 (3)	0.8207 (2)	0.0597 (8)
C3	−0.2090 (3)	0.3868 (3)	0.8583 (2)	0.0658 (9)
C4	−0.1750 (2)	0.3533 (3)	0.9303 (2)	0.0614 (8)
C5	−0.0529 (2)	0.3484 (2)	0.96918 (16)	0.0486 (6)
C6	0.0109 (2)	0.3123 (2)	1.04051 (16)	0.0513 (7)
C7	0.1312 (2)	0.3206 (2)	1.04551 (13)	0.0410 (6)
C8	0.1433 (2)	0.36452 (19)	0.97656 (13)	0.0377 (5)
C9	0.2484 (2)	0.38738 (19)	0.95104 (13)	0.0384 (5)
C10	0.2550 (2)	0.4955 (2)	0.91475 (14)	0.0456 (6)
C11	0.2281 (2)	0.2904 (2)	1.11282 (14)	0.0442 (6)
C12	0.2176 (3)	0.1938 (3)	1.15503 (17)	0.0619 (8)
C13	0.3071 (4)	0.1630 (3)	1.21741 (19)	0.0783 (11)
C14	0.4086 (4)	0.2270 (4)	1.23993 (18)	0.0790 (12)
C15	0.4196 (3)	0.3239 (3)	1.19941 (17)	0.0676 (9)
C16	0.3316 (2)	0.3549 (3)	1.13675 (15)	0.0514 (7)
C17	0.5439 (2)	0.1995 (3)	1.08230 (15)	0.0498 (6)
C18	0.6213 (3)	0.1370 (3)	1.13495 (17)	0.0609 (8)
C19	0.5956 (3)	0.0259 (3)	1.15156 (18)	0.0685 (9)
C20	0.4915 (3)	−0.0217 (3)	1.11356 (16)	0.0588 (8)
C21	0.4093 (2)	0.0395 (2)	1.05705 (14)	0.0468 (6)
C22	0.2981 (2)	0.0180 (2)	1.01050 (14)	0.0466 (6)
C23	0.2581 (2)	0.11437 (19)	0.96630 (13)	0.0394 (5)
C24	0.3452 (2)	0.19779 (19)	0.98677 (13)	0.0374 (5)
C25	0.34443 (19)	0.3151 (2)	0.96161 (12)	0.0380 (5)
C26	0.4490 (2)	0.3581 (2)	0.94301 (14)	0.0466 (6)
C27	0.1461 (2)	0.12274 (19)	0.90609 (14)	0.0416 (6)
C28	0.1429 (3)	0.1616 (2)	0.83361 (15)	0.0504 (7)
C29	0.0368 (3)	0.1635 (3)	0.77806 (18)	0.0683 (9)
C30	−0.0666 (3)	0.1298 (3)	0.7924 (2)	0.0725 (10)
C31	−0.0649 (3)	0.0910 (3)	0.8638 (2)	0.0705 (9)
C32	0.0399 (3)	0.0875 (3)	0.91917 (19)	0.0563 (7)
H1A	0.046 (3)	0.447 (3)	0.8274 (19)	0.082 (10)*
H2A	−0.143 (3)	0.440 (3)	0.7718 (18)	0.071 (10)*
H3A	−0.292 (3)	0.385 (3)	0.8299 (18)	0.082 (10)*
H4A	−0.228 (3)	0.327 (3)	0.9555 (17)	0.070 (9)*
H6A	−0.022 (2)	0.286 (2)	1.0792 (16)	0.060 (8)*
H12A	0.151 (3)	0.151 (3)	1.1404 (18)	0.073 (10)*
H13A	0.294 (3)	0.092 (3)	1.247 (2)	0.099 (12)*
H14A	0.469 (3)	0.203 (3)	1.281 (2)	0.108 (13)*
H15A	0.487 (2)	0.359 (2)	1.2148 (15)	0.051 (8)*
H16A	0.340 (2)	0.419 (2)	1.1105 (15)	0.052 (8)*
H17A	0.563 (2)	0.274 (2)	1.0734 (15)	0.053 (8)*
H18A	0.696 (2)	0.169 (2)	1.1615 (15)	0.054 (8)*
H19A	0.648 (3)	−0.018 (3)	1.1867 (19)	0.082 (10)*
H20A	0.471 (3)	−0.094 (3)	1.1235 (17)	0.068 (9)*
H22A	0.255 (2)	−0.055 (2)	1.0065 (14)	0.050 (7)*
H28A	0.209 (2)	0.184 (2)	0.8259 (15)	0.050 (8)*
H29A	0.041 (2)	0.190 (2)	0.7315 (18)	0.063 (9)*
H30A	−0.139 (3)	0.129 (3)	0.759 (2)	0.093 (12)*
H31A	−0.131 (3)	0.071 (3)	0.874 (2)	0.092 (12)*
H32A	0.044 (2)	0.059 (3)	0.9650 (17)	0.064 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0395 (11)	0.0362 (11)	0.0501 (12)	0.0005 (9)	0.0076 (9)	−0.0034 (9)
N2	0.0468 (11)	0.0385 (11)	0.0392 (11)	0.0088 (9)	0.0136 (9)	0.0013 (9)
N3	0.0805 (18)	0.0569 (16)	0.0704 (17)	−0.0161 (13)	−0.0036 (14)	0.0228 (14)
N4	0.0514 (14)	0.098 (2)	0.0659 (17)	−0.0111 (14)	0.0202 (12)	0.0085 (15)
C1	0.0499 (15)	0.0457 (15)	0.0456 (16)	−0.0018 (12)	−0.0032 (12)	0.0040 (12)
C2	0.0508 (17)	0.0555 (18)	0.062 (2)	−0.0002 (14)	−0.0038 (15)	−0.0040 (15)
C3	0.0400 (16)	0.0639 (19)	0.082 (2)	0.0080 (14)	−0.0038 (16)	−0.0108 (17)
C4	0.0411 (16)	0.0636 (19)	0.081 (2)	−0.0002 (14)	0.0190 (16)	−0.0152 (17)
C5	0.0404 (13)	0.0493 (15)	0.0578 (16)	0.0003 (11)	0.0162 (12)	−0.0117 (13)
C6	0.0506 (15)	0.0536 (16)	0.0541 (17)	0.0015 (13)	0.0217 (13)	−0.0029 (13)
C7	0.0436 (13)	0.0359 (12)	0.0444 (14)	−0.0006 (10)	0.0135 (11)	−0.0063 (11)
C8	0.0368 (12)	0.0312 (12)	0.0415 (13)	0.0014 (9)	0.0037 (10)	−0.0020 (10)
C9	0.0408 (13)	0.0344 (12)	0.0351 (12)	−0.0066 (10)	0.0015 (10)	0.0027 (10)
C10	0.0405 (13)	0.0455 (15)	0.0447 (14)	−0.0048 (11)	0.0006 (11)	0.0062 (12)
C11	0.0575 (15)	0.0415 (14)	0.0362 (13)	0.0095 (12)	0.0171 (11)	−0.0044 (11)
C12	0.087 (2)	0.0567 (18)	0.0476 (17)	0.0047 (17)	0.0274 (16)	0.0048 (14)
C13	0.111 (3)	0.078 (2)	0.0491 (19)	0.030 (2)	0.027 (2)	0.0197 (17)
C14	0.094 (3)	0.102 (3)	0.0363 (17)	0.046 (2)	0.0087 (17)	0.0026 (18)
C15	0.064 (2)	0.089 (2)	0.0442 (17)	0.0128 (19)	0.0052 (15)	−0.0129 (17)
C16	0.0556 (16)	0.0557 (18)	0.0413 (15)	0.0054 (14)	0.0101 (12)	−0.0051 (13)
C17	0.0423 (14)	0.0578 (18)	0.0469 (15)	0.0079 (13)	0.0075 (11)	−0.0023 (13)
C18	0.0533 (18)	0.073 (2)	0.0529 (17)	0.0122 (15)	0.0075 (14)	−0.0005 (15)
C19	0.072 (2)	0.078 (2)	0.0523 (18)	0.0360 (19)	0.0124 (16)	0.0135 (17)
C20	0.079 (2)	0.0523 (19)	0.0487 (17)	0.0185 (16)	0.0236 (16)	0.0124 (14)
C21	0.0616 (16)	0.0432 (14)	0.0380 (13)	0.0096 (12)	0.0173 (12)	−0.0011 (11)
C22	0.0639 (17)	0.0362 (14)	0.0429 (14)	−0.0019 (12)	0.0199 (12)	0.0020 (11)
C23	0.0475 (13)	0.0372 (13)	0.0367 (12)	−0.0020 (11)	0.0166 (10)	−0.0022 (10)
C24	0.0391 (12)	0.0354 (12)	0.0379 (12)	0.0045 (10)	0.0109 (10)	−0.0010 (10)
C25	0.0369 (12)	0.0442 (13)	0.0327 (12)	−0.0051 (10)	0.0085 (10)	−0.0002 (10)
C26	0.0432 (14)	0.0506 (15)	0.0456 (14)	−0.0031 (12)	0.0110 (11)	0.0014 (12)
C27	0.0499 (14)	0.0318 (12)	0.0432 (13)	−0.0051 (11)	0.0125 (11)	−0.0050 (10)
C28	0.0564 (17)	0.0532 (16)	0.0431 (15)	−0.0037 (13)	0.0157 (13)	−0.0023 (12)
C29	0.078 (2)	0.075 (2)	0.0436 (17)	0.0062 (18)	0.0024 (16)	−0.0068 (16)
C30	0.057 (2)	0.070 (2)	0.077 (2)	−0.0046 (17)	−0.0052 (18)	−0.0269 (18)
C31	0.0556 (19)	0.068 (2)	0.087 (3)	−0.0221 (16)	0.0164 (18)	−0.0143 (18)
C32	0.0575 (17)	0.0546 (17)	0.0584 (19)	−0.0154 (13)	0.0181 (14)	−0.0017 (14)

Geometric parameters (Å, º)

N1—C1	1.378 (3)	C14—H14A	0.93 (4)
N1—C8	1.390 (3)	C15—C16	1.371 (4)
N1—C5	1.393 (3)	C15—H15A	0.87 (3)
N2—C17	1.367 (3)	C16—H16A	0.91 (3)
N2—C24	1.395 (3)	C17—C18	1.349 (4)
N2—C21	1.399 (3)	C17—H17A	0.92 (3)
N3—C10	1.137 (3)	C18—C19	1.385 (5)
N4—C26	1.138 (3)	C18—H18A	0.95 (3)
C1—C2	1.351 (4)	C19—C20	1.350 (5)
C1—H1A	0.98 (3)	C19—H19A	0.92 (3)
C2—C3	1.410 (5)	C20—C21	1.407 (4)
C2—H2A	0.89 (3)	C20—H20A	0.91 (3)
C3—C4	1.334 (5)	C21—C22	1.374 (4)
C3—H3A	0.97 (3)	C22—C23	1.395 (3)
C4—C5	1.414 (4)	C22—H22A	0.99 (3)
C4—H4A	0.92 (3)	C23—C24	1.387 (3)
C5—C6	1.388 (4)	C23—C27	1.473 (3)
C6—C7	1.386 (3)	C24—C25	1.447 (3)
C6—H6A	0.94 (3)	C25—C26	1.441 (3)
C7—C8	1.407 (3)	C27—C32	1.386 (4)
C7—C11	1.479 (3)	C27—C28	1.396 (4)
C8—C9	1.449 (3)	C28—C29	1.378 (4)
C9—C25	1.375 (3)	C28—H28A	0.86 (3)
C9—C10	1.440 (3)	C29—C30	1.360 (5)
C11—C16	1.392 (4)	C29—H29A	0.92 (3)
C11—C12	1.393 (4)	C30—C31	1.381 (5)
C12—C13	1.377 (5)	C30—H30A	0.90 (4)
C12—H12A	0.91 (3)	C31—C32	1.367 (5)
C13—C14	1.368 (5)	C31—H31A	0.87 (4)
C13—H13A	1.03 (4)	C32—H32A	0.90 (3)
C14—C15	1.379 (5)
C1—N1—C8	129.7 (2)	C15—C16—C11	121.0 (3)
C1—N1—C5	121.2 (2)	C15—C16—H16A	120.1 (17)
C8—N1—C5	108.9 (2)	C11—C16—H16A	118.9 (17)
C17—N2—C24	130.5 (2)	C18—C17—N2	119.6 (3)
C17—N2—C21	121.0 (2)	C18—C17—H17A	119.2 (17)
C24—N2—C21	108.5 (2)	N2—C17—H17A	121.2 (17)
C2—C1—N1	119.5 (3)	C17—C18—C19	121.5 (3)
C2—C1—H1A	115.6 (19)	C17—C18—H18A	119.8 (17)
N1—C1—H1A	124.6 (19)	C19—C18—H18A	118.7 (16)
C1—C2—C3	120.4 (3)	C20—C19—C18	119.4 (3)
C1—C2—H2A	116 (2)	C20—C19—H19A	118 (2)
C3—C2—H2A	123 (2)	C18—C19—H19A	122 (2)
C4—C3—C2	120.4 (3)	C19—C20—C21	120.9 (3)
C4—C3—H3A	121.1 (19)	C19—C20—H20A	122.1 (19)
C2—C3—H3A	118.4 (19)	C21—C20—H20A	117.0 (19)
C3—C4—C5	120.5 (3)	C22—C21—N2	107.1 (2)
C3—C4—H4A	122.4 (19)	C22—C21—C20	135.3 (3)
C5—C4—H4A	116.9 (19)	N2—C21—C20	117.5 (3)
C6—C5—N1	107.4 (2)	C21—C22—C23	109.2 (2)
C6—C5—C4	134.7 (3)	C21—C22—H22A	125.7 (15)
N1—C5—C4	117.9 (3)	C23—C22—H22A	125.0 (15)
C7—C6—C5	108.7 (2)	C24—C23—C22	107.7 (2)
C7—C6—H6A	125.5 (17)	C24—C23—C27	126.6 (2)
C5—C6—H6A	125.8 (17)	C22—C23—C27	125.7 (2)
C6—C7—C8	107.9 (2)	C23—C24—N2	107.6 (2)
C6—C7—C11	125.1 (2)	C23—C24—C25	129.7 (2)
C8—C7—C11	127.0 (2)	N2—C24—C25	122.7 (2)
N1—C8—C7	107.1 (2)	C9—C25—C26	117.5 (2)
N1—C8—C9	122.1 (2)	C9—C25—C24	124.3 (2)
C7—C8—C9	130.8 (2)	C26—C25—C24	118.2 (2)
C25—C9—C10	117.6 (2)	N4—C26—C25	178.5 (3)
C25—C9—C8	124.6 (2)	C32—C27—C28	117.5 (3)
C10—C9—C8	117.7 (2)	C32—C27—C23	120.4 (2)
N3—C10—C9	179.4 (3)	C28—C27—C23	122.1 (2)
C16—C11—C12	117.4 (3)	C29—C28—C27	120.1 (3)
C16—C11—C7	122.7 (2)	C29—C28—H28A	122.7 (18)
C12—C11—C7	119.9 (3)	C27—C28—H28A	117.2 (18)
C13—C12—C11	121.0 (4)	C30—C29—C28	121.3 (3)
C13—C12—H12A	120 (2)	C30—C29—H29A	123.0 (18)
C11—C12—H12A	119 (2)	C28—C29—H29A	115.7 (18)
C14—C13—C12	120.8 (4)	C29—C30—C31	119.2 (3)
C14—C13—H13A	121 (2)	C29—C30—H30A	126 (2)
C12—C13—H13A	118 (2)	C31—C30—H30A	114 (2)
C13—C14—C15	118.9 (3)	C32—C31—C30	120.0 (3)
C13—C14—H14A	119 (3)	C32—C31—H31A	120 (2)
C15—C14—H14A	122 (3)	C30—C31—H31A	120 (2)
C16—C15—C14	120.9 (4)	C31—C32—C27	121.8 (3)
C16—C15—H15A	124.1 (19)	C31—C32—H32A	121.9 (19)
C14—C15—H15A	114.9 (19)	C27—C32—H32A	116.3 (19)
C8—N1—C1—C2	176.0 (2)	N2—C17—C18—C19	−2.4 (4)
C5—N1—C1—C2	1.1 (4)	C17—C18—C19—C20	1.0 (5)
N1—C1—C2—C3	−2.0 (4)	C18—C19—C20—C21	0.4 (5)
C1—C2—C3—C4	2.6 (5)	C17—N2—C21—C22	177.4 (2)
C2—C3—C4—C5	−2.3 (5)	C24—N2—C21—C22	0.4 (3)
C1—N1—C5—C6	177.1 (2)	C17—N2—C21—C20	−1.0 (3)
C8—N1—C5—C6	1.3 (3)	C24—N2—C21—C20	−178.0 (2)
C1—N1—C5—C4	−0.7 (4)	C19—C20—C21—C22	−178.2 (3)
C8—N1—C5—C4	−176.5 (2)	C19—C20—C21—N2	−0.4 (4)
C3—C4—C5—C6	−175.7 (3)	N2—C21—C22—C23	0.4 (3)
C3—C4—C5—N1	1.3 (4)	C20—C21—C22—C23	178.4 (3)
N1—C5—C6—C7	−1.4 (3)	C21—C22—C23—C24	−1.1 (3)
C4—C5—C6—C7	175.8 (3)	C21—C22—C23—C27	176.0 (2)
C5—C6—C7—C8	1.1 (3)	C22—C23—C24—N2	1.3 (3)
C5—C6—C7—C11	179.8 (2)	C27—C23—C24—N2	−175.7 (2)
C1—N1—C8—C7	−176.0 (2)	C22—C23—C24—C25	−175.6 (2)
C5—N1—C8—C7	−0.6 (3)	C27—C23—C24—C25	7.4 (4)
C1—N1—C8—C9	2.3 (4)	C17—N2—C24—C23	−177.6 (2)
C5—N1—C8—C9	177.7 (2)	C21—N2—C24—C23	−1.0 (2)
C6—C7—C8—N1	−0.3 (3)	C17—N2—C24—C25	−0.5 (4)
C11—C7—C8—N1	−178.9 (2)	C21—N2—C24—C25	176.1 (2)
C6—C7—C8—C9	−178.4 (2)	C10—C9—C25—C26	6.5 (3)
C11—C7—C8—C9	3.0 (4)	C8—C9—C25—C26	−170.8 (2)
N1—C8—C9—C25	−134.2 (2)	C10—C9—C25—C24	−170.5 (2)
C7—C8—C9—C25	43.6 (4)	C8—C9—C25—C24	12.1 (4)
N1—C8—C9—C10	48.4 (3)	C23—C24—C25—C9	41.4 (4)
C7—C8—C9—C10	−133.7 (3)	N2—C24—C25—C9	−135.1 (2)
C6—C7—C11—C16	−139.9 (3)	C23—C24—C25—C26	−135.6 (3)
C8—C7—C11—C16	38.6 (4)	N2—C24—C25—C26	47.9 (3)
C6—C7—C11—C12	40.2 (4)	C24—C23—C27—C32	−134.5 (3)
C8—C7—C11—C12	−141.4 (3)	C22—C23—C27—C32	49.0 (4)
C16—C11—C12—C13	−0.7 (4)	C24—C23—C27—C28	48.0 (4)
C7—C11—C12—C13	179.2 (3)	C22—C23—C27—C28	−128.4 (3)
C11—C12—C13—C14	0.4 (5)	C32—C27—C28—C29	−0.3 (4)
C12—C13—C14—C15	0.5 (5)	C23—C27—C28—C29	177.2 (2)
C13—C14—C15—C16	−1.1 (5)	C27—C28—C29—C30	1.1 (5)
C14—C15—C16—C11	0.8 (4)	C28—C29—C30—C31	−1.1 (5)
C12—C11—C16—C15	0.1 (4)	C29—C30—C31—C32	0.4 (5)
C7—C11—C16—C15	−179.8 (2)	C30—C31—C32—C27	0.4 (5)
C24—N2—C17—C18	178.7 (2)	C28—C27—C32—C31	−0.4 (4)
C21—N2—C17—C18	2.4 (4)	C23—C27—C32—C31	−178.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···N3^i	0.92 (3)	2.62 (3)	3.386 (4)	140 (2)
C30—H30A···N3^ii	0.90 (4)	2.73 (4)	3.498 (4)	144 (3)

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