8,9-Di­phenyl­imidazo­[1,2-c]­quinazoline

The title compound, C₂₂H₁₅N₃, was synthesized by the reaction of 4,5-di­phenyl-2-(2-nitro­phenyl)­imidazole with triethyl orthoformate, induced by a low-valent titanium reagent (TiCl₄/Zn). There are two independent mol­ecules of similar conformation in the asymmetric unit. X-ray analysis reveals that the imidazole ring and pyrimidine ring are essentially coplanar.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.094
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         48 Perc.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   0 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: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

8,9-diphenylimidazo[1,2-c]quinazoline

Crystal data

C22H15N3	F(000) = 1344
Mr = 321.37	Dx = 1.283 Mg m^−3
Monoclinic, P21/c	Melting point = 466–468 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.262 (2) Å	Cell parameters from 31 reflections
b = 10.814 (1) Å	θ = 3.1–13.4°
c = 23.462 (4) Å	µ = 0.08 mm^−1
β = 98.40 (1)°	T = 291 K
V = 3328.6 (8) Å^3	Block, colourless
Z = 8	0.44 × 0.42 × 0.40 mm

Data collection

Siemens P4 diffractometer	Rint = 0.015
Radiation source: normal-focus sealed tube	θmax = 25.0°, θmin = 1.6°
Graphite monochromator	h = 0→15
ω scans	k = 0→12
6709 measured reflections	l = −27→27
5856 independent reflections	3 standard reflections every 97 reflections
2804 reflections with I > 2σ(I)	intensity decay: 1.5%

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)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.0408P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.80	(Δ/σ)max < 0.001
5856 reflections	Δρmax = 0.17 e Å^−3
452 parameters	Δρmin = −0.14 e Å^−3
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0034 (2)

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
N1	0.09817 (13)	1.01090 (15)	0.62894 (7)	0.0445 (5)
N2	0.15065 (13)	0.82854 (15)	0.59964 (7)	0.0424 (5)
N3	0.15915 (14)	0.63997 (16)	0.64961 (8)	0.0534 (5)
C1	0.12270 (16)	0.7002 (2)	0.69491 (10)	0.0472 (6)
C2	0.10956 (17)	0.6314 (2)	0.74374 (10)	0.0588 (7)
H2	0.1246	0.5473	0.7451	0.071*
C3	0.07475 (19)	0.6869 (2)	0.78952 (10)	0.0646 (7)
H3	0.0653	0.6401	0.8216	0.077*
C4	0.05334 (18)	0.8130 (2)	0.78843 (10)	0.0626 (7)
H4	0.0301	0.8501	0.8198	0.075*
C5	0.06642 (16)	0.8825 (2)	0.74135 (9)	0.0535 (6)
H5	0.0529	0.9669	0.7410	0.064*
C6	0.10001 (15)	0.8271 (2)	0.69384 (9)	0.0440 (6)
C7	0.11382 (15)	0.89340 (19)	0.64291 (9)	0.0411 (5)
C8	0.17297 (16)	0.70385 (19)	0.60530 (10)	0.0504 (6)
H8	0.1993	0.6643	0.5755	0.060*
C9	0.16099 (15)	0.91233 (19)	0.55547 (8)	0.0413 (5)
C10	0.12703 (15)	1.02286 (18)	0.57452 (8)	0.0405 (5)
C11	0.11670 (15)	1.14394 (18)	0.54554 (9)	0.0420 (5)
C12	0.10640 (17)	1.1550 (2)	0.48587 (10)	0.0565 (7)
H12	0.1059	1.0847	0.4631	0.068*
C13	0.09686 (19)	1.2707 (2)	0.46049 (11)	0.0677 (7)
H13	0.0921	1.2775	0.4207	0.081*
C14	0.09438 (18)	1.3758 (2)	0.49336 (12)	0.0676 (7)
H14	0.0879	1.4532	0.4759	0.081*
C15	0.10155 (17)	1.3656 (2)	0.55224 (12)	0.0616 (7)
H15	0.0989	1.4360	0.5747	0.074*
C16	0.11271 (16)	1.25084 (19)	0.57781 (9)	0.0494 (6)
H16	0.1177	1.2449	0.6177	0.059*
C17	0.20703 (16)	0.87552 (19)	0.50465 (8)	0.0428 (5)
C18	0.29418 (17)	0.9354 (2)	0.49284 (9)	0.0521 (6)
H18	0.3225	0.9987	0.5169	0.062*
C19	0.3391 (2)	0.9017 (2)	0.44576 (10)	0.0678 (8)
H19	0.3971	0.9426	0.4378	0.081*
C20	0.2979 (3)	0.8076 (3)	0.41067 (11)	0.0802 (9)
H20	0.3280	0.7851	0.3788	0.096*
C21	0.2129 (2)	0.7467 (2)	0.42211 (10)	0.0762 (9)
H21	0.1864	0.6820	0.3984	0.091*
C22	0.16606 (18)	0.7805 (2)	0.46868 (9)	0.0584 (6)
H22	0.1074	0.7399	0.4759	0.070*
N1'	0.40582 (13)	0.12548 (15)	0.60705 (7)	0.0438 (5)
N2'	0.35495 (12)	0.31016 (15)	0.63417 (7)	0.0405 (4)
N3'	0.33677 (14)	0.49298 (16)	0.57947 (8)	0.0585 (5)
C1'	0.36842 (16)	0.4280 (2)	0.53372 (10)	0.0513 (6)
C2'	0.36893 (19)	0.4906 (2)	0.48170 (11)	0.0714 (8)
H2'	0.3506	0.5736	0.4787	0.086*
C3'	0.3963 (2)	0.4301 (3)	0.43536 (11)	0.0820 (9)
H3'	0.3956	0.4720	0.4007	0.098*
C4'	0.4254 (2)	0.3062 (3)	0.43931 (11)	0.0723 (8)
H4'	0.4443	0.2662	0.4074	0.087*
C5'	0.42624 (17)	0.2435 (2)	0.49000 (9)	0.0583 (6)
H5'	0.4464	0.1611	0.4927	0.070*
C6'	0.39694 (16)	0.3031 (2)	0.53766 (9)	0.0462 (6)
C7'	0.38985 (15)	0.2416 (2)	0.59102 (8)	0.0410 (5)
C8'	0.32979 (16)	0.4338 (2)	0.62612 (10)	0.0520 (6)
H8'	0.3066	0.4762	0.6561	0.062*
C9'	0.34543 (15)	0.22973 (18)	0.67948 (8)	0.0388 (5)
C10'	0.37805 (15)	0.11753 (18)	0.66199 (8)	0.0399 (5)
C11'	0.38588 (16)	−0.00260 (19)	0.69202 (9)	0.0429 (5)
C12'	0.38904 (17)	−0.0123 (2)	0.75154 (9)	0.0582 (7)
H12'	0.3883	0.0590	0.7737	0.070*
C13'	0.3932 (2)	−0.1261 (2)	0.77775 (11)	0.0724 (8)
H13'	0.3938	−0.1310	0.8174	0.087*
C14'	0.39634 (18)	−0.2330 (2)	0.74614 (12)	0.0676 (7)
H14'	0.3990	−0.3097	0.7642	0.081*
C15'	0.39547 (18)	−0.2250 (2)	0.68757 (11)	0.0617 (7)
H15'	0.3982	−0.2967	0.6659	0.074*
C16'	0.39048 (16)	−0.11062 (19)	0.66061 (9)	0.0496 (6)
H16'	0.3902	−0.1062	0.6210	0.059*
C17'	0.30408 (16)	0.27214 (19)	0.73127 (8)	0.0410 (5)
C18'	0.21965 (17)	0.2149 (2)	0.74781 (9)	0.0545 (6)
H18'	0.1875	0.1512	0.7254	0.065*
C19'	0.18269 (19)	0.2514 (2)	0.79721 (10)	0.0665 (7)
H19'	0.1269	0.2109	0.8084	0.080*
C20'	0.2280 (2)	0.3473 (3)	0.82984 (11)	0.0722 (8)
H20'	0.2025	0.3721	0.8629	0.087*
C21'	0.3107 (2)	0.4062 (2)	0.81356 (10)	0.0689 (7)
H21'	0.3410	0.4716	0.8354	0.083*
C22'	0.34926 (17)	0.3685 (2)	0.76463 (9)	0.0536 (6)
H22'	0.4059	0.4082	0.7541	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0506 (12)	0.0366 (11)	0.0491 (11)	0.0034 (9)	0.0168 (9)	0.0005 (9)
N2	0.0458 (12)	0.0334 (11)	0.0497 (11)	0.0029 (9)	0.0126 (9)	−0.0011 (9)
N3	0.0627 (14)	0.0385 (11)	0.0610 (12)	0.0047 (10)	0.0156 (11)	0.0067 (10)
C1	0.0443 (14)	0.0430 (14)	0.0548 (15)	−0.0020 (12)	0.0086 (12)	0.0063 (12)
C2	0.0610 (17)	0.0502 (15)	0.0646 (16)	−0.0038 (13)	0.0074 (13)	0.0126 (14)
C3	0.0731 (18)	0.0680 (18)	0.0532 (16)	−0.0119 (15)	0.0113 (14)	0.0148 (14)
C4	0.0687 (18)	0.0692 (18)	0.0523 (16)	−0.0029 (15)	0.0172 (13)	0.0044 (14)
C5	0.0543 (16)	0.0521 (15)	0.0560 (15)	−0.0007 (13)	0.0142 (12)	0.0015 (13)
C6	0.0401 (14)	0.0437 (14)	0.0500 (14)	0.0006 (11)	0.0125 (11)	0.0032 (12)
C7	0.0401 (14)	0.0347 (13)	0.0498 (14)	0.0016 (11)	0.0106 (11)	−0.0015 (11)
C8	0.0564 (16)	0.0365 (14)	0.0604 (16)	0.0053 (12)	0.0156 (13)	−0.0034 (12)
C9	0.0436 (14)	0.0371 (13)	0.0440 (13)	−0.0014 (11)	0.0091 (11)	−0.0024 (11)
C10	0.0406 (14)	0.0367 (13)	0.0450 (13)	0.0003 (10)	0.0094 (11)	0.0002 (11)
C11	0.0416 (14)	0.0380 (13)	0.0474 (14)	0.0035 (11)	0.0094 (11)	0.0030 (11)
C12	0.0658 (17)	0.0507 (16)	0.0546 (15)	0.0131 (13)	0.0137 (13)	0.0043 (12)
C13	0.078 (2)	0.0656 (18)	0.0634 (16)	0.0199 (15)	0.0234 (14)	0.0199 (15)
C14	0.0635 (18)	0.0466 (16)	0.096 (2)	0.0120 (14)	0.0223 (16)	0.0213 (16)
C15	0.0609 (18)	0.0402 (14)	0.083 (2)	0.0017 (13)	0.0072 (15)	0.0006 (14)
C16	0.0502 (15)	0.0408 (14)	0.0567 (14)	0.0026 (11)	0.0064 (12)	−0.0041 (12)
C17	0.0491 (15)	0.0378 (13)	0.0413 (13)	0.0073 (11)	0.0060 (11)	0.0006 (11)
C18	0.0579 (16)	0.0569 (15)	0.0431 (14)	0.0030 (13)	0.0130 (12)	0.0032 (11)
C19	0.081 (2)	0.0748 (19)	0.0525 (16)	0.0206 (16)	0.0267 (15)	0.0154 (15)
C20	0.128 (3)	0.076 (2)	0.0421 (16)	0.040 (2)	0.0280 (18)	0.0085 (15)
C21	0.126 (3)	0.0570 (18)	0.0413 (15)	0.0181 (18)	−0.0024 (16)	−0.0128 (14)
C22	0.0650 (17)	0.0499 (15)	0.0567 (15)	0.0014 (13)	−0.0034 (13)	−0.0063 (13)
N1'	0.0516 (12)	0.0379 (11)	0.0431 (11)	0.0012 (9)	0.0114 (9)	−0.0008 (9)
N2'	0.0427 (11)	0.0329 (10)	0.0468 (11)	0.0029 (9)	0.0096 (9)	−0.0019 (9)
N3'	0.0656 (14)	0.0454 (12)	0.0672 (13)	0.0090 (11)	0.0186 (11)	0.0137 (11)
C1'	0.0462 (15)	0.0529 (15)	0.0556 (16)	0.0013 (12)	0.0099 (12)	0.0109 (13)
C2'	0.081 (2)	0.0657 (18)	0.0697 (18)	0.0042 (16)	0.0184 (16)	0.0282 (16)
C3'	0.093 (2)	0.098 (2)	0.0576 (18)	0.0009 (19)	0.0189 (16)	0.0298 (17)
C4'	0.080 (2)	0.086 (2)	0.0539 (17)	−0.0066 (17)	0.0196 (14)	0.0073 (15)
C5'	0.0646 (17)	0.0609 (16)	0.0521 (15)	−0.0039 (13)	0.0179 (13)	0.0049 (14)
C6'	0.0447 (14)	0.0509 (15)	0.0442 (14)	−0.0032 (12)	0.0103 (11)	0.0060 (12)
C7'	0.0389 (13)	0.0413 (14)	0.0435 (13)	−0.0002 (11)	0.0087 (10)	−0.0015 (11)
C8'	0.0541 (16)	0.0419 (14)	0.0618 (16)	0.0045 (12)	0.0142 (13)	−0.0016 (12)
C9'	0.0419 (13)	0.0378 (12)	0.0373 (12)	0.0007 (11)	0.0081 (10)	0.0019 (10)
C10'	0.0418 (14)	0.0376 (13)	0.0413 (13)	0.0012 (11)	0.0090 (10)	−0.0009 (11)
C11'	0.0445 (14)	0.0379 (13)	0.0471 (14)	0.0007 (11)	0.0091 (11)	0.0007 (11)
C12'	0.0742 (18)	0.0499 (15)	0.0535 (15)	0.0091 (13)	0.0194 (13)	0.0067 (12)
C13'	0.096 (2)	0.0631 (18)	0.0635 (17)	0.0135 (16)	0.0286 (15)	0.0207 (15)
C14'	0.0731 (19)	0.0451 (16)	0.086 (2)	0.0032 (14)	0.0167 (16)	0.0239 (15)
C15'	0.0624 (17)	0.0410 (15)	0.0789 (18)	0.0010 (13)	0.0011 (14)	−0.0011 (14)
C16'	0.0506 (15)	0.0399 (14)	0.0557 (14)	0.0017 (12)	−0.0003 (12)	−0.0013 (12)
C17'	0.0436 (14)	0.0411 (13)	0.0384 (12)	0.0051 (11)	0.0069 (10)	−0.0020 (11)
C18'	0.0528 (16)	0.0643 (16)	0.0480 (14)	−0.0028 (13)	0.0124 (12)	−0.0044 (12)
C19'	0.0628 (18)	0.085 (2)	0.0563 (16)	−0.0003 (16)	0.0230 (14)	0.0014 (16)
C20'	0.084 (2)	0.087 (2)	0.0509 (16)	0.0153 (17)	0.0270 (15)	−0.0057 (16)
C21'	0.090 (2)	0.0670 (17)	0.0497 (15)	0.0078 (16)	0.0099 (15)	−0.0169 (14)
C22'	0.0567 (16)	0.0524 (15)	0.0517 (14)	−0.0004 (13)	0.0080 (12)	−0.0075 (12)

Geometric parameters (Å, º)

N1—C7	1.321 (2)	N1'—C7'	1.320 (2)
N1—C10	1.391 (2)	N1'—C10'	1.394 (2)
N2—C7	1.380 (2)	N2'—C8'	1.384 (2)
N2—C8	1.383 (2)	N2'—C7'	1.387 (2)
N2—C9	1.398 (2)	N2'—C9'	1.394 (2)
N3—C8	1.283 (2)	N3'—C8'	1.283 (2)
N3—C1	1.392 (2)	N3'—C1'	1.398 (3)
C1—C2	1.398 (3)	C1'—C2'	1.397 (3)
C1—C6	1.405 (3)	C1'—C6'	1.401 (3)
C2—C3	1.368 (3)	C2'—C3'	1.363 (3)
C2—H2	0.9300	C2'—H2'	0.9300
C3—C4	1.392 (3)	C3'—C4'	1.393 (3)
C3—H3	0.9300	C3'—H3'	0.9300
C4—C5	1.368 (3)	C4'—C5'	1.368 (3)
C4—H4	0.9300	C4'—H4'	0.9300
C5—C6	1.394 (3)	C5'—C6'	1.394 (3)
C5—H5	0.9300	C5'—H5'	0.9300
C6—C7	1.428 (3)	C6'—C7'	1.433 (3)
C8—H8	0.9300	C8'—H8'	0.9300
C9—C10	1.375 (3)	C9'—C10'	1.371 (2)
C9—C17	1.472 (3)	C9'—C17'	1.477 (3)
C10—C11	1.472 (3)	C10'—C11'	1.474 (3)
C11—C16	1.387 (3)	C11'—C16'	1.387 (3)
C11—C12	1.392 (3)	C11'—C12'	1.395 (3)
C12—C13	1.383 (3)	C12'—C13'	1.373 (3)
C12—H12	0.9300	C12'—H12'	0.9300
C13—C14	1.377 (3)	C13'—C14'	1.377 (3)
C13—H13	0.9300	C13'—H13'	0.9300
C14—C15	1.375 (3)	C14'—C15'	1.375 (3)
C14—H14	0.9300	C14'—H14'	0.9300
C15—C16	1.377 (3)	C15'—C16'	1.387 (3)
C15—H15	0.9300	C15'—H15'	0.9300
C16—H16	0.9300	C16'—H16'	0.9300
C17—C18	1.388 (3)	C17'—C18'	1.384 (3)
C17—C22	1.389 (3)	C17'—C22'	1.386 (3)
C18—C19	1.378 (3)	C18'—C19'	1.381 (3)
C18—H18	0.9300	C18'—H18'	0.9300
C19—C20	1.371 (3)	C19'—C20'	1.374 (3)
C19—H19	0.9300	C19'—H19'	0.9300
C20—C21	1.365 (4)	C20'—C21'	1.371 (3)
C20—H20	0.9300	C20'—H20'	0.9300
C21—C22	1.383 (3)	C21'—C22'	1.385 (3)
C21—H21	0.9300	C21'—H21'	0.9300
C22—H22	0.9300	C22'—H22'	0.9300
C7—N1—C10	105.23 (16)	C7'—N1'—C10'	105.62 (16)
C7—N2—C8	121.24 (19)	C8'—N2'—C7'	121.04 (18)
C7—N2—C9	107.41 (16)	C8'—N2'—C9'	131.30 (18)
C8—N2—C9	131.32 (18)	C7'—N2'—C9'	107.49 (16)
C8—N3—C1	118.26 (18)	C8'—N3'—C1'	118.11 (19)
N3—C1—C2	118.4 (2)	C2'—C1'—N3'	117.9 (2)
N3—C1—C6	122.7 (2)	C2'—C1'—C6'	119.3 (2)
C2—C1—C6	118.9 (2)	N3'—C1'—C6'	122.8 (2)
C3—C2—C1	120.5 (2)	C3'—C2'—C1'	120.0 (2)
C3—C2—H2	119.8	C3'—C2'—H2'	120.0
C1—C2—H2	119.8	C1'—C2'—H2'	120.0
C2—C3—C4	120.4 (2)	C2'—C3'—C4'	120.8 (2)
C2—C3—H3	119.8	C2'—C3'—H3'	119.6
C4—C3—H3	119.8	C4'—C3'—H3'	119.6
C5—C4—C3	120.2 (2)	C5'—C4'—C3'	120.1 (3)
C5—C4—H4	119.9	C5'—C4'—H4'	120.0
C3—C4—H4	119.9	C3'—C4'—H4'	120.0
C4—C5—C6	120.2 (2)	C4'—C5'—C6'	120.0 (2)
C4—C5—H5	119.9	C4'—C5'—H5'	120.0
C6—C5—H5	119.9	C6'—C5'—H5'	120.0
C5—C6—C1	119.9 (2)	C5'—C6'—C1'	119.8 (2)
C5—C6—C7	123.2 (2)	C5'—C6'—C7'	123.2 (2)
C1—C6—C7	116.9 (2)	C1'—C6'—C7'	116.9 (2)
N1—C7—N2	111.46 (18)	N1'—C7'—N2'	110.92 (17)
N1—C7—C6	130.98 (19)	N1'—C7'—C6'	131.5 (2)
N2—C7—C6	117.55 (18)	N2'—C7'—C6'	117.48 (19)
N3—C8—N2	123.3 (2)	N3'—C8'—N2'	123.5 (2)
N3—C8—H8	118.4	N3'—C8'—H8'	118.2
N2—C8—H8	118.4	N2'—C8'—H8'	118.2
C10—C9—N2	104.49 (16)	C10'—C9'—N2'	104.84 (16)
C10—C9—C17	133.86 (19)	C10'—C9'—C17'	133.81 (19)
N2—C9—C17	121.50 (18)	N2'—C9'—C17'	121.31 (18)
C9—C10—N1	111.38 (17)	C9'—C10'—N1'	111.09 (17)
C9—C10—C11	129.48 (18)	C9'—C10'—C11'	129.79 (18)
N1—C10—C11	119.13 (18)	N1'—C10'—C11'	119.11 (17)
C16—C11—C12	118.1 (2)	C16'—C11'—C12'	118.1 (2)
C16—C11—C10	119.83 (19)	C16'—C11'—C10'	119.58 (19)
C12—C11—C10	122.01 (19)	C12'—C11'—C10'	122.28 (19)
C13—C12—C11	120.0 (2)	C13'—C12'—C11'	120.6 (2)
C13—C12—H12	120.0	C13'—C12'—H12'	119.7
C11—C12—H12	120.0	C11'—C12'—H12'	119.7
C14—C13—C12	120.9 (2)	C12'—C13'—C14'	120.9 (2)
C14—C13—H13	119.5	C12'—C13'—H13'	119.6
C12—C13—H13	119.5	C14'—C13'—H13'	119.6
C15—C14—C13	119.5 (2)	C15'—C14'—C13'	119.3 (2)
C15—C14—H14	120.3	C15'—C14'—H14'	120.4
C13—C14—H14	120.3	C13'—C14'—H14'	120.4
C14—C15—C16	119.8 (2)	C14'—C15'—C16'	120.3 (2)
C14—C15—H15	120.1	C14'—C15'—H15'	119.9
C16—C15—H15	120.1	C16'—C15'—H15'	119.9
C15—C16—C11	121.6 (2)	C15'—C16'—C11'	120.8 (2)
C15—C16—H16	119.2	C15'—C16'—H16'	119.6
C11—C16—H16	119.2	C11'—C16'—H16'	119.6
C18—C17—C22	119.2 (2)	C18'—C17'—C22'	118.6 (2)
C18—C17—C9	119.46 (19)	C18'—C17'—C9'	120.30 (19)
C22—C17—C9	121.4 (2)	C22'—C17'—C9'	121.1 (2)
C19—C18—C17	120.4 (2)	C19'—C18'—C17'	120.6 (2)
C19—C18—H18	119.8	C19'—C18'—H18'	119.7
C17—C18—H18	119.8	C17'—C18'—H18'	119.7
C20—C19—C18	119.7 (3)	C20'—C19'—C18'	120.3 (2)
C20—C19—H19	120.1	C20'—C19'—H19'	119.9
C18—C19—H19	120.1	C18'—C19'—H19'	119.9
C21—C20—C19	120.6 (2)	C21'—C20'—C19'	119.9 (2)
C21—C20—H20	119.7	C21'—C20'—H20'	120.1
C19—C20—H20	119.7	C19'—C20'—H20'	120.1
C20—C21—C22	120.4 (2)	C20'—C21'—C22'	120.1 (2)
C20—C21—H21	119.8	C20'—C21'—H21'	119.9
C22—C21—H21	119.8	C22'—C21'—H21'	119.9
C21—C22—C17	119.7 (2)	C21'—C22'—C17'	120.5 (2)
C21—C22—H22	120.2	C21'—C22'—H22'	119.7
C17—C22—H22	120.2	C17'—C22'—H22'	119.7
C8—N3—C1—C2	−178.7 (2)	C8'—N3'—C1'—C2'	175.5 (2)
C8—N3—C1—C6	0.4 (3)	C8'—N3'—C1'—C6'	−2.9 (3)
N3—C1—C2—C3	179.4 (2)	N3'—C1'—C2'—C3'	−178.1 (2)
C6—C1—C2—C3	0.3 (3)	C6'—C1'—C2'—C3'	0.4 (4)
C1—C2—C3—C4	−0.9 (4)	C1'—C2'—C3'—C4'	−0.9 (4)
C2—C3—C4—C5	0.4 (4)	C2'—C3'—C4'—C5'	0.4 (4)
C3—C4—C5—C6	0.8 (4)	C3'—C4'—C5'—C6'	0.7 (4)
C4—C5—C6—C1	−1.5 (3)	C4'—C5'—C6'—C1'	−1.1 (3)
C4—C5—C6—C7	179.0 (2)	C4'—C5'—C6'—C7'	176.1 (2)
N3—C1—C6—C5	−178.2 (2)	C2'—C1'—C6'—C5'	0.6 (3)
C2—C1—C6—C5	0.9 (3)	N3'—C1'—C6'—C5'	179.0 (2)
N3—C1—C6—C7	1.4 (3)	C2'—C1'—C6'—C7'	−176.8 (2)
C2—C1—C6—C7	−179.52 (19)	N3'—C1'—C6'—C7'	1.7 (3)
C10—N1—C7—N2	−0.6 (2)	C10'—N1'—C7'—N2'	1.4 (2)
C10—N1—C7—C6	178.7 (2)	C10'—N1'—C7'—C6'	−174.7 (2)
C8—N2—C7—N1	179.63 (18)	C8'—N2'—C7'—N1'	−177.82 (18)
C9—N2—C7—N1	1.3 (2)	C9'—N2'—C7'—N1'	−2.1 (2)
C8—N2—C7—C6	0.3 (3)	C8'—N2'—C7'—C6'	−1.1 (3)
C9—N2—C7—C6	−178.07 (18)	C9'—N2'—C7'—C6'	174.62 (18)
C5—C6—C7—N1	−1.3 (4)	C5'—C6'—C7'—N1'	−1.1 (4)
C1—C6—C7—N1	179.1 (2)	C1'—C6'—C7'—N1'	176.2 (2)
C5—C6—C7—N2	177.9 (2)	C5'—C6'—C7'—N2'	−176.9 (2)
C1—C6—C7—N2	−1.6 (3)	C1'—C6'—C7'—N2'	0.3 (3)
C1—N3—C8—N2	−2.0 (3)	C1'—N3'—C8'—N2'	2.1 (3)
C7—N2—C8—N3	1.7 (3)	C7'—N2'—C8'—N3'	−0.1 (3)
C9—N2—C8—N3	179.5 (2)	C9'—N2'—C8'—N3'	−174.7 (2)
C7—N2—C9—C10	−1.4 (2)	C8'—N2'—C9'—C10'	176.9 (2)
C8—N2—C9—C10	−179.5 (2)	C7'—N2'—C9'—C10'	1.8 (2)
C7—N2—C9—C17	174.68 (19)	C8'—N2'—C9'—C17'	−1.3 (3)
C8—N2—C9—C17	−3.4 (3)	C7'—N2'—C9'—C17'	−176.47 (18)
N2—C9—C10—N1	1.1 (2)	N2'—C9'—C10'—N1'	−1.0 (2)
C17—C9—C10—N1	−174.3 (2)	C17'—C9'—C10'—N1'	176.9 (2)
N2—C9—C10—C11	−177.8 (2)	N2'—C9'—C10'—C11'	179.6 (2)
C17—C9—C10—C11	6.8 (4)	C17'—C9'—C10'—C11'	−2.5 (4)
C7—N1—C10—C9	−0.4 (2)	C7'—N1'—C10'—C9'	−0.3 (2)
C7—N1—C10—C11	178.66 (18)	C7'—N1'—C10'—C11'	179.23 (18)
C9—C10—C11—C16	−159.3 (2)	C9'—C10'—C11'—C16'	160.2 (2)
N1—C10—C11—C16	21.9 (3)	N1'—C10'—C11'—C16'	−19.2 (3)
C9—C10—C11—C12	23.5 (3)	C9'—C10'—C11'—C12'	−19.9 (4)
N1—C10—C11—C12	−155.3 (2)	N1'—C10'—C11'—C12'	160.7 (2)
C16—C11—C12—C13	2.7 (3)	C16'—C11'—C12'—C13'	−2.1 (3)
C10—C11—C12—C13	180.0 (2)	C10'—C11'—C12'—C13'	178.0 (2)
C11—C12—C13—C14	−1.9 (4)	C11'—C12'—C13'—C14'	1.3 (4)
C12—C13—C14—C15	0.0 (4)	C12'—C13'—C14'—C15'	0.1 (4)
C13—C14—C15—C16	1.0 (4)	C13'—C14'—C15'—C16'	−0.6 (4)
C14—C15—C16—C11	−0.2 (4)	C14'—C15'—C16'—C11'	−0.3 (4)
C12—C11—C16—C15	−1.7 (3)	C12'—C11'—C16'—C15'	1.6 (3)
C10—C11—C16—C15	−179.0 (2)	C10'—C11'—C16'—C15'	−178.5 (2)
C10—C9—C17—C18	55.1 (3)	C10'—C9'—C17'—C18'	−55.0 (3)
N2—C9—C17—C18	−119.7 (2)	N2'—C9'—C17'—C18'	122.7 (2)
C10—C9—C17—C22	−126.0 (3)	C10'—C9'—C17'—C22'	124.3 (3)
N2—C9—C17—C22	59.2 (3)	N2'—C9'—C17'—C22'	−58.1 (3)
C22—C17—C18—C19	0.5 (3)	C22'—C17'—C18'—C19'	−1.4 (3)
C9—C17—C18—C19	179.43 (19)	C9'—C17'—C18'—C19'	177.9 (2)
C17—C18—C19—C20	−0.6 (3)	C17'—C18'—C19'—C20'	1.6 (4)
C18—C19—C20—C21	−0.3 (4)	C18'—C19'—C20'—C21'	−0.6 (4)
C19—C20—C21—C22	1.2 (4)	C19'—C20'—C21'—C22'	−0.6 (4)
C20—C21—C22—C17	−1.3 (4)	C20'—C21'—C22'—C17'	0.8 (4)
C18—C17—C22—C21	0.4 (3)	C18'—C17'—C22'—C21'	0.2 (3)
C9—C17—C22—C21	−178.5 (2)	C9'—C17'—C22'—C21'	−179.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···N3′	0.93	2.59	3.267 (3)	130
C8′—H8′···N3	0.93	2.63	3.280 (3)	128