N,N'-Bis(1-naphthyl)-N,N'-diphenyl-1,1'-biphenyl-4,4'-diamine

The title complex, C₄₄H₃₂N₂, is a useful charge-carrier transport material in organic electroluminescence devices. There are two half-molecules in the asymmetric unit; each molecule possesses a centre of symmetry at the mid-point of the central C-C bond.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.124
• Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C25    -   C26     ..      11.44 su

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.754     1.000
            Tmin(prime) and Tmax expected:      0.965     0.994
            RR(prime) =      0.777
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.78
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.57 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C27    -   C28     ..       6.02 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C29    -   C30     ..       5.21 su

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

   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
   2 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, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

N,N'-Bis(1-naphthyl)-N,N'-diphenyl-1,1'-biphenyl-4,4'-diamine

Crystal data

C44H32N2	Z = 2
Mr = 588.72	F(000) = 620
Triclinic, P1	Dx = 1.223 Mg m^−3
a = 10.3089 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.3382 (10) Å	Cell parameters from 984 reflections
c = 14.5056 (13) Å	θ = 2.4–25.7°
α = 82.378 (1)°	µ = 0.07 mm^−1
β = 77.671 (2)°	T = 293 K
γ = 75.565 (1)°	Needle, yellow
V = 1598.4 (2) Å^3	0.50 × 0.30 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer	6574 independent reflections
Radiation source: fine-focus sealed tube	4494 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.011
φ and ω scans	θmax = 27.8°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→12
Tmin = 0.754, Tmax = 1.000	k = −14→14
9404 measured reflections	l = −18→12

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)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.124	w = 1/[σ^2(Fo^2) + (0.0633P)^2 + 0.0935P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
6574 reflections	Δρmax = 0.19 e Å^−3
416 parameters	Δρmin = −0.16 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0078 (17)

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
C1	0.41040 (17)	0.62586 (16)	0.31713 (13)	0.0755 (5)
H1	0.3561	0.6972	0.2938	0.091*
C2	0.5431 (2)	0.6213 (2)	0.31879 (17)	0.1029 (7)
H2	0.5787	0.6897	0.2964	0.124*
C3	0.6262 (2)	0.5152 (3)	0.35366 (19)	0.1160 (8)
H3	0.7164	0.5137	0.3550	0.139*
C4	0.5772 (2)	0.4157 (2)	0.38521 (15)	0.0983 (6)
H4	0.6341	0.3457	0.4080	0.118*
C5	0.44089 (17)	0.41486 (16)	0.38466 (11)	0.0703 (4)
C6	0.3886 (2)	0.30983 (17)	0.41437 (13)	0.0855 (5)
H6	0.4450	0.2385	0.4357	0.103*
C7	0.2582 (2)	0.31074 (16)	0.41247 (13)	0.0865 (5)
H7	0.2258	0.2401	0.4318	0.104*
C8	0.17137 (17)	0.41790 (14)	0.38143 (12)	0.0703 (4)
H8	0.0811	0.4180	0.3814	0.084*
C9	0.21719 (14)	0.52175 (12)	0.35127 (10)	0.0546 (3)
C10	0.35466 (14)	0.52274 (13)	0.35069 (10)	0.0576 (4)
C11	0.07005 (14)	0.62887 (11)	0.23901 (9)	0.0511 (3)
C12	0.15249 (15)	0.58513 (13)	0.15738 (10)	0.0617 (4)
H12	0.2449	0.5523	0.1562	0.074*
C13	0.09919 (17)	0.58950 (15)	0.07715 (11)	0.0727 (4)
H13	0.1562	0.5596	0.0223	0.087*
C14	−0.03615 (18)	0.63710 (16)	0.07724 (12)	0.0766 (5)
H14	−0.0712	0.6412	0.0226	0.092*
C15	−0.11943 (17)	0.67864 (17)	0.15871 (13)	0.0823 (5)
H15	−0.2119	0.7107	0.1595	0.099*
C16	−0.06782 (15)	0.67354 (15)	0.23990 (12)	0.0699 (4)
H16	−0.1259	0.7002	0.2953	0.084*
C17	0.09035 (13)	0.73389 (11)	0.37175 (9)	0.0490 (3)
C18	0.04489 (15)	0.84910 (12)	0.32941 (10)	0.0585 (4)
H18	0.0377	0.8579	0.2659	0.070*
C19	0.01016 (14)	0.95077 (12)	0.37903 (9)	0.0548 (3)
H19	−0.0208	1.0266	0.3481	0.066*
C20	0.01938 (12)	0.94475 (11)	0.47352 (8)	0.0451 (3)
C21	0.06817 (17)	0.82849 (13)	0.51459 (10)	0.0651 (4)
H21	0.0780	0.8199	0.5776	0.078*
C22	0.10255 (17)	0.72559 (13)	0.46563 (10)	0.0644 (4)
H22	0.1344	0.6496	0.4961	0.077*
C23	0.28870 (14)	0.06342 (12)	0.13774 (10)	0.0544 (3)
C24	0.32630 (19)	−0.04746 (14)	0.10105 (12)	0.0721 (4)
H24	0.4175	−0.0888	0.0925	0.086*
C25	0.2324 (3)	−0.10004 (18)	0.07629 (13)	0.0871 (5)
H25	0.2606	−0.1759	0.0517	0.104*
C26	0.1000 (2)	−0.04088 (19)	0.08796 (12)	0.0873 (6)
H26	0.0375	−0.0765	0.0708	0.105*
C27	0.05368 (16)	0.07575 (16)	0.12622 (10)	0.0670 (4)
C28	−0.0831 (2)	0.1400 (3)	0.14090 (14)	0.0949 (7)
H28	−0.1473	0.1075	0.1228	0.114*
C29	−0.12430 (19)	0.2470 (3)	0.18023 (16)	0.1049 (7)
H29	−0.2161	0.2865	0.1900	0.126*
C30	−0.02962 (17)	0.29955 (19)	0.20655 (13)	0.0854 (5)
H30	−0.0588	0.3742	0.2331	0.102*
C31	0.10469 (14)	0.24200 (14)	0.19356 (11)	0.0616 (4)
H31	0.1669	0.2770	0.2117	0.074*
C32	0.15002 (13)	0.12874 (13)	0.15242 (9)	0.0532 (3)
C33	0.45866 (13)	0.04461 (11)	0.23532 (10)	0.0534 (3)
C34	0.38887 (17)	−0.00181 (14)	0.31808 (11)	0.0675 (4)
H34	0.2947	0.0089	0.3273	0.081*
C35	0.4589 (2)	−0.06424 (17)	0.38726 (14)	0.0923 (6)
H35	0.4115	−0.0959	0.4431	0.111*
C36	0.5970 (2)	−0.08016 (18)	0.37480 (17)	0.1058 (7)
H36	0.6432	−0.1202	0.4227	0.127*
C37	0.6666 (2)	−0.03718 (17)	0.29197 (18)	0.1035 (7)
H37	0.7608	−0.0488	0.2829	0.124*
C38	0.59859 (16)	0.02323 (15)	0.22177 (14)	0.0785 (5)
H38	0.6473	0.0500	0.1645	0.094*
C39	0.42173 (12)	0.22089 (11)	0.11699 (9)	0.0470 (3)
C40	0.39261 (14)	0.26281 (12)	0.02784 (10)	0.0535 (3)
H40	0.3518	0.2181	−0.0020	0.064*
C41	0.42363 (14)	0.37048 (12)	−0.01718 (9)	0.0527 (3)
H41	0.4032	0.3962	−0.0771	0.063*
C42	0.48434 (11)	0.44171 (10)	0.02383 (9)	0.0427 (3)
C43	0.51196 (13)	0.39799 (11)	0.11371 (9)	0.0500 (3)
H43	0.5525	0.4426	0.1439	0.060*
C44	0.48138 (13)	0.29122 (12)	0.15930 (10)	0.0525 (3)
H44	0.5010	0.2657	0.2194	0.063*
N1	0.12645 (12)	0.62980 (10)	0.32012 (8)	0.0586 (3)
N2	0.38804 (11)	0.11247 (10)	0.16463 (9)	0.0559 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0703 (10)	0.0688 (10)	0.0874 (12)	−0.0164 (8)	−0.0027 (9)	−0.0246 (9)
C2	0.0754 (13)	0.1040 (16)	0.1327 (18)	−0.0315 (12)	0.0082 (12)	−0.0457 (14)
C3	0.0628 (12)	0.144 (2)	0.146 (2)	−0.0160 (14)	−0.0135 (13)	−0.0539 (18)
C4	0.0723 (12)	0.1169 (17)	0.1000 (15)	0.0112 (12)	−0.0318 (11)	−0.0264 (13)
C5	0.0725 (10)	0.0745 (11)	0.0597 (9)	0.0030 (8)	−0.0224 (8)	−0.0132 (8)
C6	0.0995 (14)	0.0708 (11)	0.0743 (11)	0.0065 (10)	−0.0299 (10)	0.0080 (9)
C7	0.1084 (15)	0.0584 (10)	0.0899 (13)	−0.0174 (10)	−0.0259 (11)	0.0121 (9)
C8	0.0775 (10)	0.0569 (9)	0.0798 (11)	−0.0155 (8)	−0.0232 (9)	−0.0031 (8)
C9	0.0656 (9)	0.0470 (7)	0.0512 (8)	−0.0043 (6)	−0.0175 (7)	−0.0096 (6)
C10	0.0626 (9)	0.0585 (8)	0.0517 (8)	−0.0057 (7)	−0.0134 (7)	−0.0165 (6)
C11	0.0569 (8)	0.0458 (7)	0.0531 (8)	−0.0076 (6)	−0.0173 (6)	−0.0093 (6)
C12	0.0586 (8)	0.0627 (9)	0.0604 (9)	0.0025 (7)	−0.0155 (7)	−0.0175 (7)
C13	0.0809 (11)	0.0757 (10)	0.0583 (9)	0.0004 (8)	−0.0176 (8)	−0.0222 (8)
C14	0.0861 (12)	0.0809 (11)	0.0710 (11)	−0.0082 (9)	−0.0370 (9)	−0.0202 (9)
C15	0.0588 (9)	0.1061 (14)	0.0888 (13)	−0.0072 (9)	−0.0290 (9)	−0.0299 (11)
C16	0.0549 (9)	0.0883 (11)	0.0676 (10)	−0.0105 (8)	−0.0088 (7)	−0.0264 (8)
C17	0.0541 (7)	0.0468 (7)	0.0465 (7)	−0.0076 (6)	−0.0127 (6)	−0.0076 (6)
C18	0.0802 (10)	0.0520 (8)	0.0426 (7)	−0.0048 (7)	−0.0218 (7)	−0.0050 (6)
C19	0.0711 (9)	0.0450 (7)	0.0468 (7)	−0.0046 (6)	−0.0192 (7)	−0.0017 (6)
C20	0.0467 (7)	0.0474 (7)	0.0408 (7)	−0.0096 (5)	−0.0088 (5)	−0.0037 (5)
C21	0.0978 (11)	0.0532 (8)	0.0408 (7)	−0.0040 (8)	−0.0219 (7)	−0.0030 (6)
C22	0.0928 (11)	0.0453 (8)	0.0501 (8)	−0.0019 (7)	−0.0201 (8)	−0.0020 (6)
C23	0.0606 (8)	0.0495 (8)	0.0579 (8)	−0.0217 (6)	−0.0177 (7)	0.0071 (6)
C24	0.0914 (11)	0.0539 (9)	0.0741 (10)	−0.0206 (8)	−0.0192 (9)	−0.0031 (8)
C25	0.1295 (18)	0.0711 (11)	0.0758 (12)	−0.0429 (12)	−0.0311 (12)	−0.0024 (9)
C26	0.1329 (18)	0.1004 (14)	0.0617 (10)	−0.0808 (14)	−0.0406 (11)	0.0170 (10)
C27	0.0690 (10)	0.0929 (12)	0.0537 (9)	−0.0462 (9)	−0.0264 (7)	0.0195 (8)
C28	0.0682 (12)	0.156 (2)	0.0737 (12)	−0.0571 (13)	−0.0257 (10)	0.0241 (13)
C29	0.0476 (10)	0.166 (2)	0.0881 (15)	−0.0156 (12)	−0.0151 (10)	0.0209 (15)
C30	0.0581 (10)	0.1019 (14)	0.0821 (12)	−0.0017 (9)	−0.0094 (9)	0.0040 (10)
C31	0.0542 (8)	0.0645 (9)	0.0654 (9)	−0.0143 (7)	−0.0147 (7)	0.0045 (7)
C32	0.0543 (8)	0.0603 (8)	0.0497 (7)	−0.0246 (6)	−0.0174 (6)	0.0125 (6)
C33	0.0523 (8)	0.0413 (7)	0.0686 (9)	−0.0134 (6)	−0.0202 (7)	0.0080 (6)
C34	0.0681 (9)	0.0624 (9)	0.0721 (10)	−0.0199 (7)	−0.0160 (8)	0.0086 (8)
C35	0.1184 (16)	0.0841 (12)	0.0787 (12)	−0.0362 (11)	−0.0341 (12)	0.0295 (10)
C36	0.1193 (17)	0.0894 (14)	0.1245 (18)	−0.0354 (13)	−0.0759 (15)	0.0440 (13)
C37	0.0735 (12)	0.0809 (12)	0.159 (2)	−0.0200 (10)	−0.0577 (13)	0.0442 (13)
C38	0.0534 (9)	0.0703 (10)	0.1045 (13)	−0.0136 (7)	−0.0226 (9)	0.0296 (9)
C39	0.0397 (6)	0.0434 (7)	0.0566 (8)	−0.0097 (5)	−0.0104 (6)	0.0036 (6)
C40	0.0590 (8)	0.0508 (8)	0.0565 (8)	−0.0203 (6)	−0.0171 (7)	−0.0002 (6)
C41	0.0624 (8)	0.0510 (8)	0.0479 (7)	−0.0177 (6)	−0.0161 (6)	0.0026 (6)
C42	0.0365 (6)	0.0403 (6)	0.0485 (7)	−0.0063 (5)	−0.0061 (5)	−0.0018 (5)
C43	0.0521 (7)	0.0476 (7)	0.0550 (8)	−0.0163 (6)	−0.0183 (6)	0.0020 (6)
C44	0.0561 (8)	0.0518 (8)	0.0535 (8)	−0.0172 (6)	−0.0210 (6)	0.0088 (6)
N1	0.0706 (7)	0.0480 (6)	0.0580 (7)	0.0008 (5)	−0.0253 (6)	−0.0135 (5)
N2	0.0523 (6)	0.0497 (6)	0.0708 (8)	−0.0207 (5)	−0.0231 (6)	0.0135 (5)

Geometric parameters (Å, º)

C1—C2	1.361 (3)	C23—C24	1.364 (2)
C1—C10	1.414 (2)	C23—C32	1.4219 (19)
C1—H1	0.9300	C23—N2	1.4220 (17)
C2—C3	1.396 (3)	C24—C25	1.384 (2)
C2—H2	0.9300	C24—H24	0.9300
C3—C4	1.336 (3)	C25—C26	1.348 (3)
C3—H3	0.9300	C25—H25	0.9300
C4—C5	1.410 (3)	C26—C27	1.432 (3)
C4—H4	0.9300	C26—H26	0.9300
C5—C6	1.407 (3)	C27—C28	1.402 (3)
C5—C10	1.419 (2)	C27—C32	1.4180 (19)
C6—C7	1.348 (3)	C28—C29	1.342 (3)
C6—H6	0.9300	C28—H28	0.9300
C7—C8	1.402 (2)	C29—C30	1.401 (3)
C7—H7	0.9300	C29—H29	0.9300
C8—C9	1.361 (2)	C30—C31	1.360 (2)
C8—H8	0.9300	C30—H30	0.9300
C9—C10	1.418 (2)	C31—C32	1.417 (2)
C9—N1	1.4291 (17)	C31—H31	0.9300
C11—C12	1.3734 (19)	C33—C34	1.374 (2)
C11—C16	1.3827 (19)	C33—C38	1.377 (2)
C11—N1	1.4217 (16)	C33—N2	1.4156 (17)
C12—C13	1.380 (2)	C34—C35	1.377 (2)
C12—H12	0.9300	C34—H34	0.9300
C13—C14	1.364 (2)	C35—C36	1.365 (3)
C13—H13	0.9300	C35—H35	0.9300
C14—C15	1.367 (2)	C36—C37	1.359 (3)
C14—H14	0.9300	C36—H36	0.9300
C15—C16	1.381 (2)	C37—C38	1.370 (2)
C15—H15	0.9300	C37—H37	0.9300
C16—H16	0.9300	C38—H38	0.9300
C17—C18	1.3813 (18)	C39—C40	1.3856 (18)
C17—C22	1.3829 (18)	C39—C44	1.3878 (18)
C17—N1	1.4102 (16)	C39—N2	1.4122 (15)
C18—C19	1.3709 (18)	C40—C41	1.3832 (18)
C18—H18	0.9300	C40—H40	0.9300
C19—C20	1.3856 (18)	C41—C42	1.3915 (17)
C19—H19	0.9300	C41—H41	0.9300
C20—C21	1.3909 (18)	C42—C43	1.3940 (17)
C20—C20^i	1.481 (2)	C42—C42^ii	1.485 (2)
C21—C22	1.3773 (19)	C43—C44	1.3751 (17)
C21—H21	0.9300	C43—H43	0.9300
C22—H22	0.9300	C44—H44	0.9300
C2—C1—C10	120.38 (18)	C23—C24—C25	121.77 (18)
C2—C1—H1	119.8	C23—C24—H24	119.1
C10—C1—H1	119.8	C25—C24—H24	119.1
C1—C2—C3	120.7 (2)	C26—C25—C24	119.77 (18)
C1—C2—H2	119.6	C26—C25—H25	120.1
C3—C2—H2	119.6	C24—C25—H25	120.1
C4—C3—C2	120.5 (2)	C25—C26—C27	121.31 (15)
C4—C3—H3	119.8	C25—C26—H26	119.3
C2—C3—H3	119.8	C27—C26—H26	119.3
C3—C4—C5	121.3 (2)	C28—C27—C32	117.82 (18)
C3—C4—H4	119.4	C28—C27—C26	123.42 (17)
C5—C4—H4	119.4	C32—C27—C26	118.74 (16)
C6—C5—C4	122.20 (17)	C29—C28—C27	122.08 (18)
C6—C5—C10	118.98 (15)	C29—C28—H28	119.0
C4—C5—C10	118.80 (18)	C27—C28—H28	119.0
C7—C6—C5	121.21 (15)	C28—C29—C30	120.30 (18)
C7—C6—H6	119.4	C28—C29—H29	119.8
C5—C6—H6	119.4	C30—C29—H29	119.8
C6—C7—C8	120.13 (17)	C31—C30—C29	120.4 (2)
C6—C7—H7	119.9	C31—C30—H30	119.8
C8—C7—H7	119.9	C29—C30—H30	119.8
C9—C8—C7	120.99 (16)	C30—C31—C32	120.10 (16)
C9—C8—H8	119.5	C30—C31—H31	119.9
C7—C8—H8	119.5	C32—C31—H31	119.9
C8—C9—C10	120.10 (13)	C31—C32—C27	119.29 (14)
C8—C9—N1	119.85 (14)	C31—C32—C23	122.87 (12)
C10—C9—N1	120.05 (13)	C27—C32—C23	117.83 (14)
C1—C10—C9	123.13 (13)	C34—C33—C38	119.00 (14)
C1—C10—C5	118.32 (15)	C34—C33—N2	120.58 (12)
C9—C10—C5	118.55 (14)	C38—C33—N2	120.42 (13)
C12—C11—C16	118.64 (13)	C33—C34—C35	119.73 (16)
C12—C11—N1	120.35 (12)	C33—C34—H34	120.1
C16—C11—N1	121.01 (12)	C35—C34—H34	120.1
C11—C12—C13	120.49 (14)	C36—C35—C34	120.74 (18)
C11—C12—H12	119.8	C36—C35—H35	119.6
C13—C12—H12	119.8	C34—C35—H35	119.6
C14—C13—C12	120.80 (15)	C37—C36—C35	119.56 (17)
C14—C13—H13	119.6	C37—C36—H36	120.2
C12—C13—H13	119.6	C35—C36—H36	120.2
C13—C14—C15	119.09 (15)	C36—C37—C38	120.35 (18)
C13—C14—H14	120.5	C36—C37—H37	119.8
C15—C14—H14	120.5	C38—C37—H37	119.8
C14—C15—C16	120.76 (15)	C37—C38—C33	120.50 (17)
C14—C15—H15	119.6	C37—C38—H38	119.7
C16—C15—H15	119.6	C33—C38—H38	119.7
C15—C16—C11	120.16 (14)	C40—C39—C44	117.68 (11)
C15—C16—H16	119.9	C40—C39—N2	121.31 (12)
C11—C16—H16	119.9	C44—C39—N2	120.98 (12)
C18—C17—C22	117.28 (12)	C41—C40—C39	120.69 (12)
C18—C17—N1	121.04 (12)	C41—C40—H40	119.7
C22—C17—N1	121.65 (12)	C39—C40—H40	119.7
C19—C18—C17	121.38 (12)	C40—C41—C42	122.43 (12)
C19—C18—H18	119.3	C40—C41—H41	118.8
C17—C18—H18	119.3	C42—C41—H41	118.8
C18—C19—C20	122.48 (12)	C41—C42—C43	115.81 (11)
C18—C19—H19	118.8	C41—C42—C42^ii	122.44 (14)
C20—C19—H19	118.8	C43—C42—C42^ii	121.75 (14)
C19—C20—C21	115.47 (12)	C44—C43—C42	122.33 (12)
C19—C20—C20^i	121.93 (14)	C44—C43—H43	118.8
C21—C20—C20^i	122.60 (14)	C42—C43—H43	118.8
C22—C21—C20	122.56 (12)	C43—C44—C39	121.06 (12)
C22—C21—H21	118.7	C43—C44—H44	119.5
C20—C21—H21	118.7	C39—C44—H44	119.5
C21—C22—C17	120.81 (13)	C17—N1—C11	120.98 (10)
C21—C22—H22	119.6	C17—N1—C9	119.88 (11)
C17—C22—H22	119.6	C11—N1—C9	119.10 (10)
C24—C23—C32	120.57 (13)	C39—N2—C33	121.31 (10)
C24—C23—N2	119.85 (14)	C39—N2—C23	120.59 (10)
C32—C23—N2	119.54 (12)	C33—N2—C23	117.93 (10)

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