[N,N'-Diphenyl­ureato(2-)][phthalo­cyaninato(2-)]titanium(IV)

In the title complex, [Ti(C₃₂H₁₆N₈)(C₁₃H₁₀N₂O)], the geometry around the Ti atom is square pyramidal, with the four isoindoline N atoms forming the basal plane and the ureate group at the apical site. The crystal structure is formed by close packing of centrosymmetric dimers, consisting of slightly offset mol­ecules related by a crystallographic center of inversion in a face-to-face manner.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.042
• wR factor = 0.091
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.01
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        229
            O41 -C41 -TI1 -N49    78.00  3.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        231
            O41 -C41 -TI1 -N42  -108.00  3.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        233
            O41 -C41 -TI1 -N32   164.00  3.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        236
            O41 -C41 -TI1 -N12   -15.00  3.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        239
            O41 -C41 -TI1 -N22  -103.00  3.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        242
            O41 -C41 -TI1 -N1     73.00  3.00   1.555   1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 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
   0 ALERT type 3 Indicator that the structure quality may be low
   7 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2003); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

[N,N'-Diphenylureato(2-)][phthalocyaninato(2-)]titanium(IV)

Crystal data

[Ti(C32H16N8)(C13H10N2O)]	F(000) = 1584
Mr = 770.66	Dx = 1.49 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 10560 reflections
a = 11.8342 (10) Å	θ = 1.6–16°
b = 26.0933 (19) Å	µ = 0.31 mm^−1
c = 12.4701 (11) Å	T = 193 K
β = 116.845 (6)°	Prism, black
V = 3435.7 (5) Å^3	0.3 × 0.12 × 0.08 mm
Z = 4

Data collection

Stoe IPDS-2 diffractometer	3564 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.072
ω scans	θmax = 26.3°, θmin = 1.6°
Absorption correction: multi-scan (Blessing, 1995)	h = −14→14
Tmin = 0.923, Tmax = 0.962	k = −32→32
25798 measured reflections	l = −15→15
6900 independent reflections

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) = 0.091	w = 1/[σ^2(Fo^2) + (0.0405P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.80	(Δ/σ)max < 0.001
6900 reflections	Δρmax = 0.25 e Å^−3
515 parameters	Δρmin = −0.34 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: 0.00083 (16)

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.

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

	x	y	z	Uiso*/Ueq
C2	−0.2646 (2)	0.08878 (11)	−0.1973 (2)	0.0417 (7)
C3	−0.3900 (3)	0.06647 (11)	−0.2455 (2)	0.0436 (7)
C4	−0.5019 (3)	0.07827 (12)	−0.3462 (3)	0.0484 (7)
H4	−0.5048	0.1042	−0.4008	0.058*
C5	−0.6086 (3)	0.05102 (12)	−0.3642 (3)	0.0510 (7)
H5	−0.6864	0.0581	−0.4329	0.061*
C6	−0.6048 (3)	0.01345 (12)	−0.2839 (3)	0.0522 (8)
H6	−0.68	−0.0048	−0.2992	0.063*
C7	−0.4941 (3)	0.00188 (11)	−0.1817 (3)	0.0483 (7)
H7	−0.4918	−0.0236	−0.1263	0.058*
C8	−0.3867 (2)	0.02932 (11)	−0.1643 (2)	0.0425 (7)
C9	−0.2594 (3)	0.03057 (11)	−0.0653 (3)	0.0421 (7)
C11	−0.1117 (3)	0.00527 (11)	0.1260 (2)	0.0425 (7)
C13	0.0889 (3)	0.02535 (11)	0.2470 (3)	0.0435 (7)
C14	0.0521 (3)	−0.01314 (11)	0.3088 (3)	0.0437 (7)
C15	0.1166 (3)	−0.03543 (11)	0.4207 (3)	0.0497 (7)
H15	0.2022	−0.0267	0.4724	0.06*
C16	0.0523 (3)	−0.07074 (12)	0.4545 (3)	0.0541 (8)
H16	0.0937	−0.086	0.5319	0.065*
C17	−0.0726 (3)	−0.08470 (12)	0.3775 (3)	0.0548 (8)
H17	−0.1142	−0.1096	0.4026	0.066*
C18	−0.1358 (3)	−0.06266 (11)	0.2657 (3)	0.0497 (7)
H18	−0.2203	−0.0722	0.2129	0.06*
C19	−0.0728 (3)	−0.02622 (11)	0.2323 (3)	0.0423 (7)
C21	0.2405 (2)	0.07591 (11)	0.2281 (2)	0.0405 (7)
C23	0.2404 (2)	0.12946 (11)	0.0894 (2)	0.0396 (6)
C24	0.3699 (2)	0.12712 (11)	0.1848 (2)	0.0430 (7)
C25	0.4791 (3)	0.15248 (12)	0.2004 (3)	0.0478 (7)
H25	0.4795	0.1754	0.1413	0.057*
C26	0.5883 (3)	0.14296 (12)	0.3065 (3)	0.0528 (8)
H26	0.6648	0.1598	0.3204	0.063*
C27	0.5876 (3)	0.10918 (12)	0.3927 (3)	0.0496 (7)
H27	0.6634	0.1039	0.4647	0.059*
C28	0.4791 (3)	0.08329 (11)	0.3757 (3)	0.0466 (7)
H28	0.4794	0.0595	0.4336	0.056*
C29	0.3694 (2)	0.09328 (11)	0.2708 (2)	0.0415 (7)
C31	0.0884 (2)	0.15994 (11)	−0.0943 (2)	0.0424 (7)
C33	−0.1167 (3)	0.14364 (11)	−0.2112 (2)	0.0429 (7)
C34	−0.0742 (3)	0.17591 (11)	−0.2801 (2)	0.0425 (7)
C35	−0.1347 (3)	0.19353 (12)	−0.3986 (3)	0.0514 (8)
H35	−0.2224	0.1876	−0.448	0.062*
C36	−0.0620 (3)	0.21998 (12)	−0.4411 (3)	0.0544 (8)
H36	−0.1002	0.2309	−0.5225	0.065*
C37	0.0648 (3)	0.23111 (12)	−0.3689 (3)	0.0508 (8)
H37	0.1112	0.25	−0.401	0.061*
C38	0.1244 (3)	0.21490 (11)	−0.2504 (3)	0.0468 (7)
H38	0.2107	0.2229	−0.2	0.056*
C39	0.0536 (3)	0.18650 (11)	−0.2075 (2)	0.0412 (7)
C41	−0.1016 (2)	0.17239 (11)	0.1610 (2)	0.0406 (7)
C43	0.1292 (2)	0.17887 (10)	0.2802 (2)	0.0389 (6)
C44	0.2192 (3)	0.20765 (11)	0.2653 (3)	0.0437 (7)
H44	0.2043	0.2183	0.1872	0.052*
C45	0.3313 (3)	0.22103 (12)	0.3642 (3)	0.0492 (7)
H45	0.3938	0.2399	0.353	0.059*
C46	0.3531 (3)	0.20716 (12)	0.4790 (3)	0.0517 (8)
H46	0.4301	0.2161	0.5465	0.062*
C47	0.2611 (3)	0.18017 (12)	0.4936 (3)	0.0540 (8)
H47	0.2741	0.1713	0.5722	0.065*
C48	0.1496 (3)	0.16566 (12)	0.3951 (2)	0.0484 (7)
H48	0.0874	0.1467	0.4066	0.058*
C50	−0.3102 (2)	0.14632 (10)	0.0020 (2)	0.0373 (6)
C51	−0.3844 (2)	0.11166 (12)	0.0261 (2)	0.0441 (7)
H51	−0.3463	0.0868	0.0878	0.053*
C52	−0.5153 (3)	0.11366 (12)	−0.0409 (3)	0.0477 (7)
H52	−0.5668	0.0895	−0.0264	0.057*
C53	−0.5705 (3)	0.15030 (11)	−0.1278 (3)	0.0480 (7)
H53	−0.66	0.1511	−0.1737	0.058*
C54	−0.4980 (3)	0.18556 (11)	−0.1490 (3)	0.0486 (7)
H54	−0.5369	0.2115	−0.2079	0.058*
C55	−0.3666 (3)	0.18351 (11)	−0.0840 (3)	0.0448 (7)
H55	−0.3158	0.2079	−0.0992	0.054*
N1	−0.1871 (2)	0.06698 (8)	−0.08677 (19)	0.0398 (5)
N10	−0.2257 (2)	0.00180 (9)	0.0323 (2)	0.0451 (6)
N12	−0.0137 (2)	0.03771 (9)	0.1383 (2)	0.0420 (6)
N20	0.2059 (2)	0.04332 (9)	0.2894 (2)	0.0427 (6)
N22	0.16339 (19)	0.09827 (9)	0.11829 (19)	0.0395 (5)
N30	0.2058 (2)	0.15854 (9)	−0.0075 (2)	0.0439 (6)
N32	−0.0175 (2)	0.13546 (9)	−0.09667 (19)	0.0414 (5)
N40	−0.2320 (2)	0.12399 (9)	−0.2549 (2)	0.0443 (6)
N42	0.01951 (19)	0.16056 (9)	0.17731 (19)	0.0400 (5)
N49	−0.17500 (19)	0.14208 (8)	0.06171 (19)	0.0394 (5)
Ti1	−0.03397 (4)	0.10668 (2)	0.04952 (4)	0.03871 (14)
O41	−0.13570 (18)	0.20112 (8)	0.21765 (18)	0.0568 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0390 (15)	0.0464 (17)	0.0361 (16)	0.0044 (13)	0.0138 (13)	−0.0040 (13)
C3	0.0411 (16)	0.0485 (18)	0.0366 (16)	0.0030 (14)	0.0134 (14)	−0.0090 (14)
C4	0.0423 (16)	0.0566 (19)	0.0381 (17)	0.0024 (14)	0.0109 (14)	−0.0043 (15)
C5	0.0393 (16)	0.058 (2)	0.0446 (18)	−0.0005 (15)	0.0090 (14)	−0.0052 (16)
C6	0.0418 (17)	0.0516 (19)	0.055 (2)	−0.0042 (15)	0.0145 (16)	−0.0114 (16)
C7	0.0429 (17)	0.0455 (19)	0.0486 (18)	−0.0017 (14)	0.0137 (15)	−0.0050 (15)
C8	0.0360 (15)	0.0451 (18)	0.0402 (16)	0.0017 (13)	0.0119 (13)	−0.0076 (14)
C9	0.0389 (15)	0.0429 (17)	0.0412 (17)	0.0019 (13)	0.0150 (14)	−0.0058 (14)
C11	0.0375 (15)	0.0433 (17)	0.0416 (17)	0.0013 (13)	0.0133 (14)	−0.0033 (14)
C13	0.0367 (15)	0.0439 (17)	0.0432 (17)	0.0031 (13)	0.0122 (14)	−0.0021 (14)
C14	0.0416 (16)	0.0414 (17)	0.0432 (17)	0.0032 (14)	0.0147 (14)	0.0017 (14)
C15	0.0432 (17)	0.0467 (18)	0.0472 (18)	0.0014 (14)	0.0097 (15)	0.0032 (15)
C16	0.056 (2)	0.0492 (18)	0.0478 (18)	0.0008 (16)	0.0155 (17)	0.0057 (16)
C17	0.058 (2)	0.0435 (18)	0.062 (2)	−0.0041 (15)	0.0255 (18)	0.0056 (16)
C18	0.0443 (17)	0.0452 (18)	0.0522 (19)	−0.0033 (14)	0.0152 (15)	0.0003 (15)
C19	0.0382 (15)	0.0386 (17)	0.0445 (17)	0.0033 (13)	0.0138 (14)	0.0000 (14)
C21	0.0370 (15)	0.0460 (17)	0.0370 (16)	0.0049 (13)	0.0155 (14)	−0.0008 (14)
C23	0.0343 (14)	0.0457 (17)	0.0395 (16)	0.0033 (13)	0.0172 (13)	−0.0047 (14)
C24	0.0340 (14)	0.0537 (18)	0.0382 (16)	0.0020 (13)	0.0136 (13)	−0.0042 (14)
C25	0.0383 (16)	0.059 (2)	0.0448 (17)	−0.0008 (14)	0.0176 (14)	−0.0037 (15)
C26	0.0352 (16)	0.063 (2)	0.0515 (19)	−0.0027 (15)	0.0121 (15)	−0.0074 (17)
C27	0.0364 (15)	0.0546 (18)	0.0474 (17)	0.0009 (15)	0.0099 (13)	−0.0039 (17)
C28	0.0422 (16)	0.0505 (18)	0.0424 (17)	0.0064 (14)	0.0150 (14)	−0.0017 (14)
C29	0.0350 (14)	0.0488 (18)	0.0369 (16)	0.0025 (13)	0.0128 (13)	−0.0037 (14)
C31	0.0365 (15)	0.0511 (18)	0.0379 (16)	0.0028 (13)	0.0152 (14)	−0.0029 (14)
C33	0.0377 (15)	0.0517 (18)	0.0356 (16)	0.0033 (14)	0.0134 (13)	−0.0015 (14)
C34	0.0427 (16)	0.0475 (18)	0.0357 (15)	0.0045 (14)	0.0163 (14)	−0.0008 (13)
C35	0.0475 (17)	0.057 (2)	0.0413 (17)	0.0042 (15)	0.0123 (15)	0.0040 (16)
C36	0.061 (2)	0.056 (2)	0.0434 (17)	0.0032 (16)	0.0207 (16)	0.0112 (16)
C37	0.0495 (18)	0.0523 (19)	0.0521 (19)	0.0070 (15)	0.0241 (16)	0.0082 (16)
C38	0.0418 (16)	0.0476 (18)	0.0487 (18)	0.0067 (14)	0.0183 (15)	0.0016 (15)
C39	0.0403 (15)	0.0480 (17)	0.0352 (15)	0.0059 (13)	0.0170 (13)	0.0001 (14)
C41	0.0388 (15)	0.0442 (17)	0.0381 (16)	0.0016 (13)	0.0167 (13)	−0.0007 (14)
C43	0.0370 (15)	0.0403 (16)	0.0377 (16)	0.0002 (13)	0.0154 (13)	−0.0056 (13)
C44	0.0432 (16)	0.0463 (17)	0.0382 (16)	−0.0004 (14)	0.0152 (14)	−0.0036 (14)
C45	0.0428 (16)	0.0478 (19)	0.057 (2)	−0.0050 (14)	0.0227 (16)	−0.0070 (15)
C46	0.0411 (16)	0.056 (2)	0.0482 (19)	0.0025 (15)	0.0114 (15)	−0.0066 (16)
C47	0.0531 (19)	0.064 (2)	0.0377 (17)	0.0008 (16)	0.0140 (15)	0.0008 (15)
C48	0.0456 (17)	0.0582 (19)	0.0386 (16)	−0.0073 (15)	0.0165 (14)	0.0024 (15)
C50	0.0331 (14)	0.0405 (16)	0.0341 (15)	0.0047 (12)	0.0115 (12)	−0.0030 (13)
C51	0.0401 (15)	0.0485 (17)	0.0444 (16)	0.0065 (14)	0.0197 (13)	0.0073 (15)
C52	0.0390 (15)	0.0527 (19)	0.0527 (18)	−0.0016 (14)	0.0217 (14)	0.0015 (16)
C53	0.0387 (16)	0.0502 (19)	0.0482 (18)	0.0045 (14)	0.0136 (14)	−0.0039 (15)
C54	0.0463 (17)	0.0422 (18)	0.0472 (18)	0.0052 (14)	0.0121 (15)	0.0062 (14)
C55	0.0425 (16)	0.0419 (17)	0.0460 (17)	−0.0022 (14)	0.0165 (14)	0.0009 (14)
N1	0.0356 (12)	0.0441 (14)	0.0353 (13)	0.0039 (11)	0.0121 (11)	−0.0011 (11)
N10	0.0413 (13)	0.0430 (14)	0.0432 (14)	0.0006 (11)	0.0120 (12)	−0.0026 (12)
N12	0.0351 (12)	0.0458 (14)	0.0383 (13)	0.0008 (11)	0.0106 (11)	−0.0020 (11)
N20	0.0358 (13)	0.0451 (14)	0.0414 (14)	0.0027 (11)	0.0125 (11)	−0.0011 (12)
N22	0.0353 (11)	0.0446 (14)	0.0349 (12)	0.0035 (11)	0.0125 (10)	−0.0023 (11)
N30	0.0375 (13)	0.0547 (15)	0.0372 (13)	0.0027 (11)	0.0150 (11)	−0.0005 (12)
N32	0.0351 (12)	0.0501 (14)	0.0352 (13)	0.0019 (11)	0.0124 (10)	−0.0038 (11)
N40	0.0392 (13)	0.0541 (16)	0.0356 (13)	−0.0003 (11)	0.0132 (11)	−0.0045 (12)
N42	0.0340 (12)	0.0475 (14)	0.0365 (13)	0.0007 (11)	0.0142 (11)	−0.0012 (11)
N49	0.0335 (12)	0.0432 (14)	0.0359 (13)	−0.0026 (10)	0.0107 (10)	−0.0064 (11)
Ti1	0.0338 (2)	0.0449 (3)	0.0341 (3)	0.0022 (2)	0.0124 (2)	−0.0030 (3)
O41	0.0449 (12)	0.0661 (14)	0.0578 (13)	−0.0006 (10)	0.0217 (11)	−0.0241 (12)

Geometric parameters (Å, º)

C2—N40	1.327 (3)	C31—N32	1.395 (3)
C2—N1	1.386 (3)	C31—C39	1.456 (4)
C2—C3	1.448 (4)	C33—N40	1.323 (3)
C3—C4	1.387 (4)	C33—N32	1.395 (3)
C3—C8	1.389 (4)	C33—C34	1.446 (4)
C4—C5	1.377 (4)	C34—C39	1.395 (4)
C4—H4	0.95	C34—C35	1.397 (4)
C5—C6	1.387 (4)	C35—C36	1.382 (4)
C5—H5	0.95	C35—H35	0.95
C6—C7	1.387 (4)	C36—C37	1.389 (4)
C6—H6	0.95	C36—H36	0.95
C7—C8	1.387 (4)	C37—C38	1.385 (4)
C7—H7	0.95	C37—H37	0.95
C8—C9	1.454 (4)	C38—C39	1.393 (4)
C9—N10	1.328 (3)	C38—H38	0.95
C9—N1	1.384 (3)	C41—O41	1.217 (3)
C11—N10	1.331 (3)	C41—N42	1.389 (3)
C11—N12	1.387 (3)	C41—N49	1.393 (3)
C11—C19	1.446 (4)	C41—Ti1	2.553 (3)
C13—N20	1.325 (3)	C43—C44	1.383 (4)
C13—N12	1.389 (3)	C43—C48	1.385 (4)
C13—C14	1.448 (4)	C43—N42	1.434 (3)
C14—C15	1.381 (4)	C44—C45	1.388 (4)
C14—C19	1.391 (4)	C44—H44	0.95
C15—C16	1.377 (4)	C45—C46	1.382 (4)
C15—H15	0.95	C45—H45	0.95
C16—C17	1.399 (4)	C46—C47	1.376 (4)
C16—H16	0.95	C46—H46	0.95
C17—C18	1.375 (4)	C47—C48	1.388 (4)
C17—H17	0.95	C47—H47	0.95
C18—C19	1.383 (4)	C48—H48	0.95
C18—H18	0.95	C50—C55	1.375 (4)
C21—N20	1.326 (3)	C50—C51	1.385 (4)
C21—N22	1.385 (3)	C50—N49	1.432 (3)
C21—C29	1.443 (4)	C51—C52	1.390 (4)
C23—N30	1.326 (3)	C51—H51	0.95
C23—N22	1.385 (3)	C52—C53	1.370 (4)
C23—C24	1.456 (4)	C52—H52	0.95
C24—C25	1.385 (4)	C53—C54	1.363 (4)
C24—C29	1.391 (4)	C53—H53	0.95
C25—C26	1.392 (4)	C54—C55	1.392 (4)
C25—H25	0.95	C54—H54	0.95
C26—C27	1.393 (4)	C55—H55	0.95
C26—H26	0.95	N1—Ti1	2.113 (2)
C27—C28	1.380 (4)	N12—Ti1	2.069 (2)
C27—H27	0.95	N22—Ti1	2.105 (2)
C28—C29	1.390 (4)	N32—Ti1	2.060 (2)
C28—H28	0.95	N42—Ti1	2.001 (2)
C31—N30	1.320 (3)	N49—Ti1	1.972 (2)
N40—C2—N1	126.8 (2)	C37—C38—H38	121.1
N40—C2—C3	123.2 (3)	C39—C38—H38	121.1
N1—C2—C3	110.0 (2)	C38—C39—C34	121.4 (3)
C4—C3—C8	121.1 (3)	C38—C39—C31	132.0 (3)
C4—C3—C2	131.8 (3)	C34—C39—C31	106.5 (2)
C8—C3—C2	106.9 (2)	O41—C41—N42	130.0 (3)
C5—C4—C3	117.6 (3)	O41—C41—N49	129.0 (2)
C5—C4—H4	121.2	N42—C41—N49	101.1 (2)
C3—C4—H4	121.2	O41—C41—Ti1	175.8 (2)
C4—C5—C6	121.3 (3)	N42—C41—Ti1	51.23 (13)
C4—C5—H5	119.4	N49—C41—Ti1	50.05 (12)
C6—C5—H5	119.4	C44—C43—C48	119.3 (3)
C7—C6—C5	121.7 (3)	C44—C43—N42	120.1 (2)
C7—C6—H6	119.1	C48—C43—N42	120.5 (2)
C5—C6—H6	119.1	C43—C44—C45	120.1 (3)
C6—C7—C8	116.7 (3)	C43—C44—H44	119.9
C6—C7—H7	121.6	C45—C44—H44	119.9
C8—C7—H7	121.6	C46—C45—C44	120.7 (3)
C7—C8—C3	121.6 (3)	C46—C45—H45	119.6
C7—C8—C9	131.9 (3)	C44—C45—H45	119.6
C3—C8—C9	106.3 (2)	C47—C46—C45	118.8 (3)
N10—C9—N1	127.5 (2)	C47—C46—H46	120.6
N10—C9—C8	122.2 (3)	C45—C46—H46	120.6
N1—C9—C8	110.2 (2)	C46—C47—C48	121.0 (3)
N10—C11—N12	127.1 (3)	C46—C47—H47	119.5
N10—C11—C19	122.9 (3)	C48—C47—H47	119.5
N12—C11—C19	110.0 (2)	C43—C48—C47	119.9 (3)
N20—C13—N12	127.1 (3)	C43—C48—H48	120
N20—C13—C14	123.0 (3)	C47—C48—H48	120
N12—C13—C14	109.9 (2)	C55—C50—C51	119.9 (2)
C15—C14—C19	121.4 (3)	C55—C50—N49	119.7 (2)
C15—C14—C13	131.9 (3)	C51—C50—N49	120.4 (2)
C19—C14—C13	106.7 (2)	C50—C51—C52	119.3 (3)
C16—C15—C14	117.5 (3)	C50—C51—H51	120.4
C16—C15—H15	121.3	C52—C51—H51	120.4
C14—C15—H15	121.3	C53—C52—C51	120.4 (3)
C15—C16—C17	121.5 (3)	C53—C52—H52	119.8
C15—C16—H16	119.3	C51—C52—H52	119.8
C17—C16—H16	119.3	C54—C53—C52	120.5 (3)
C18—C17—C16	120.6 (3)	C54—C53—H53	119.7
C18—C17—H17	119.7	C52—C53—H53	119.7
C16—C17—H17	119.7	C53—C54—C55	119.8 (3)
C17—C18—C19	118.2 (3)	C53—C54—H54	120.1
C17—C18—H18	120.9	C55—C54—H54	120.1
C19—C18—H18	120.9	C50—C55—C54	120.1 (3)
C18—C19—C14	120.8 (3)	C50—C55—H55	119.9
C18—C19—C11	132.4 (3)	C54—C55—H55	119.9
C14—C19—C11	106.8 (2)	C9—N1—C2	106.5 (2)
N20—C21—N22	127.1 (2)	C9—N1—Ti1	124.19 (18)
N20—C21—C29	122.6 (3)	C2—N1—Ti1	122.73 (18)
N22—C21—C29	110.3 (2)	C9—N10—C11	122.2 (2)
N30—C23—N22	127.2 (2)	C11—N12—C13	106.5 (2)
N30—C23—C24	123.1 (2)	C11—N12—Ti1	125.65 (18)
N22—C23—C24	109.7 (2)	C13—N12—Ti1	124.26 (18)
C25—C24—C29	121.6 (3)	C13—N20—C21	122.4 (2)
C25—C24—C23	131.7 (3)	C21—N22—C23	106.7 (2)
C29—C24—C23	106.7 (2)	C21—N22—Ti1	124.14 (16)
C24—C25—C26	117.0 (3)	C23—N22—Ti1	124.91 (18)
C24—C25—H25	121.5	C31—N30—C23	122.7 (2)
C26—C25—H25	121.5	C33—N32—C31	106.5 (2)
C25—C26—C27	121.4 (3)	C33—N32—Ti1	126.11 (17)
C25—C26—H26	119.3	C31—N32—Ti1	126.20 (18)
C27—C26—H26	119.3	C33—N40—C2	122.9 (2)
C28—C27—C26	121.4 (3)	C41—N42—C43	121.0 (2)
C28—C27—H27	119.3	C41—N42—Ti1	96.02 (16)
C26—C27—H27	119.3	C43—N42—Ti1	141.22 (17)
C27—C28—C29	117.5 (3)	C41—N49—C50	121.3 (2)
C27—C28—H28	121.3	C41—N49—Ti1	97.17 (16)
C29—C28—H28	121.3	C50—N49—Ti1	141.41 (17)
C28—C29—C24	121.2 (3)	N49—Ti1—N42	65.42 (8)
C28—C29—C21	132.1 (3)	N49—Ti1—N32	108.59 (9)
C24—C29—C21	106.7 (2)	N42—Ti1—N32	109.04 (9)
N30—C31—N32	127.4 (3)	N49—Ti1—N12	105.29 (9)
N30—C31—C39	122.7 (2)	N42—Ti1—N12	105.45 (9)
N32—C31—C39	109.8 (2)	N32—Ti1—N12	139.10 (9)
N40—C33—N32	126.7 (2)	N49—Ti1—N22	147.07 (9)
N40—C33—C34	123.4 (2)	N42—Ti1—N22	81.67 (8)
N32—C33—C34	109.9 (2)	N32—Ti1—N22	82.40 (8)
C39—C34—C35	120.5 (3)	N12—Ti1—N22	81.50 (9)
C39—C34—C33	107.2 (2)	N49—Ti1—N1	81.00 (8)
C35—C34—C33	132.1 (3)	N42—Ti1—N1	146.41 (8)
C36—C35—C34	117.4 (3)	N32—Ti1—N1	81.73 (9)
C36—C35—H35	121.3	N12—Ti1—N1	81.60 (9)
C34—C35—H35	121.3	N22—Ti1—N1	131.86 (8)
C35—C36—C37	122.3 (3)	N49—Ti1—C41	32.78 (8)
C35—C36—H36	118.9	N42—Ti1—C41	32.75 (8)
C37—C36—H36	118.9	N32—Ti1—C41	114.52 (9)
C38—C37—C36	120.5 (3)	N12—Ti1—C41	106.38 (9)
C38—C37—H37	119.7	N22—Ti1—C41	114.30 (8)
C36—C37—H37	119.7	N1—Ti1—C41	113.66 (8)
C37—C38—C39	117.8 (3)
N40—C2—C3—C4	−7.9 (5)	N30—C23—N22—Ti1	−21.9 (4)
N1—C2—C3—C4	173.6 (3)	C24—C23—N22—Ti1	156.75 (17)
N40—C2—C3—C8	176.5 (2)	N32—C31—N30—C23	4.8 (4)
N1—C2—C3—C8	−2.0 (3)	C39—C31—N30—C23	−171.7 (2)
C8—C3—C4—C5	−1.5 (4)	N22—C23—N30—C31	−2.4 (4)
C2—C3—C4—C5	−176.6 (3)	C24—C23—N30—C31	179.1 (3)
C3—C4—C5—C6	0.6 (4)	N40—C33—N32—C31	174.8 (3)
C4—C5—C6—C7	0.5 (5)	C34—C33—N32—C31	−2.9 (3)
C5—C6—C7—C8	−0.7 (4)	N40—C33—N32—Ti1	−17.1 (4)
C6—C7—C8—C3	−0.2 (4)	C34—C33—N32—Ti1	165.30 (17)
C6—C7—C8—C9	174.4 (3)	N30—C31—N32—C33	−173.7 (3)
C4—C3—C8—C7	1.3 (4)	C39—C31—N32—C33	3.2 (3)
C2—C3—C8—C7	177.4 (2)	N30—C31—N32—Ti1	18.1 (4)
C4—C3—C8—C9	−174.5 (3)	C39—C31—N32—Ti1	−164.98 (17)
C2—C3—C8—C9	1.7 (3)	N32—C33—N40—C2	−7.2 (4)
C7—C8—C9—N10	0.6 (5)	C34—C33—N40—C2	170.2 (3)
C3—C8—C9—N10	175.8 (2)	N1—C2—N40—C33	−0.7 (4)
C7—C8—C9—N1	−176.0 (3)	C3—C2—N40—C33	−178.9 (3)
C3—C8—C9—N1	−0.9 (3)	O41—C41—N42—C43	6.9 (5)
N20—C13—C14—C15	6.8 (5)	N49—C41—N42—C43	−172.7 (2)
N12—C13—C14—C15	−175.8 (3)	Ti1—C41—N42—C43	−167.9 (3)
N20—C13—C14—C19	−173.9 (3)	O41—C41—N42—Ti1	174.8 (3)
N12—C13—C14—C19	3.6 (3)	N49—C41—N42—Ti1	−4.8 (2)
C19—C14—C15—C16	−0.8 (4)	C44—C43—N42—C41	−123.4 (3)
C13—C14—C15—C16	178.5 (3)	C48—C43—N42—C41	60.1 (4)
C14—C15—C16—C17	1.7 (5)	C44—C43—N42—Ti1	76.0 (4)
C15—C16—C17—C18	−1.1 (5)	C48—C43—N42—Ti1	−100.5 (3)
C16—C17—C18—C19	−0.5 (4)	O41—C41—N49—C50	8.1 (4)
C17—C18—C19—C14	1.4 (4)	N42—C41—N49—C50	−172.2 (2)
C17—C18—C19—C11	−177.1 (3)	Ti1—C41—N49—C50	−177.1 (3)
C15—C14—C19—C18	−0.8 (4)	O41—C41—N49—Ti1	−174.7 (3)
C13—C14—C19—C18	179.7 (3)	N42—C41—N49—Ti1	4.9 (2)
C15—C14—C19—C11	178.1 (3)	C55—C50—N49—C41	84.1 (3)
C13—C14—C19—C11	−1.4 (3)	C51—C50—N49—C41	−99.1 (3)
N10—C11—C19—C18	−3.0 (5)	C55—C50—N49—Ti1	−91.4 (3)
N12—C11—C19—C18	177.5 (3)	C51—C50—N49—Ti1	85.5 (3)
N10—C11—C19—C14	178.3 (3)	C41—N49—Ti1—N42	−3.66 (15)
N12—C11—C19—C14	−1.2 (3)	C50—N49—Ti1—N42	172.4 (3)
N30—C23—C24—C25	1.7 (5)	C41—N49—Ti1—N32	−106.65 (16)
N22—C23—C24—C25	−177.0 (3)	C50—N49—Ti1—N32	69.4 (3)
N30—C23—C24—C29	179.5 (2)	C41—N49—Ti1—N12	96.63 (16)
N22—C23—C24—C29	0.8 (3)	C50—N49—Ti1—N12	−87.3 (3)
C29—C24—C25—C26	−0.5 (4)	C41—N49—Ti1—N22	−1.4 (3)
C23—C24—C25—C26	177.1 (3)	C50—N49—Ti1—N22	174.7 (2)
C24—C25—C26—C27	0.3 (4)	C41—N49—Ti1—N1	175.29 (17)
C25—C26—C27—C28	0.9 (5)	C50—N49—Ti1—N1	−8.6 (3)
C26—C27—C28—C29	−1.8 (4)	C50—N49—Ti1—C41	176.1 (4)
C27—C28—C29—C24	1.6 (4)	C41—N42—Ti1—N49	3.67 (15)
C27—C28—C29—C21	−175.7 (3)	C43—N42—Ti1—N49	167.0 (3)
C25—C24—C29—C28	−0.5 (4)	C41—N42—Ti1—N32	105.96 (16)
C23—C24—C29—C28	−178.6 (2)	C43—N42—Ti1—N32	−90.7 (3)
C25—C24—C29—C21	177.5 (3)	C41—N42—Ti1—N12	−96.37 (16)
C23—C24—C29—C21	−0.6 (3)	C43—N42—Ti1—N12	67.0 (3)
N20—C21—C29—C28	−1.8 (5)	C41—N42—Ti1—N22	−175.10 (17)
N22—C21—C29—C28	177.9 (3)	C43—N42—Ti1—N22	−11.7 (3)
N20—C21—C29—C24	−179.4 (2)	C41—N42—Ti1—N1	1.8 (3)
N22—C21—C29—C24	0.2 (3)	C43—N42—Ti1—N1	165.2 (2)
N40—C33—C34—C39	−176.3 (3)	C43—N42—Ti1—C41	163.4 (4)
N32—C33—C34—C39	1.5 (3)	C33—N32—Ti1—N49	−46.2 (2)
N40—C33—C34—C35	−0.2 (5)	C31—N32—Ti1—N49	119.7 (2)
N32—C33—C34—C35	177.5 (3)	C33—N32—Ti1—N42	−115.8 (2)
C39—C34—C35—C36	2.2 (4)	C31—N32—Ti1—N42	50.1 (2)
C33—C34—C35—C36	−173.4 (3)	C33—N32—Ti1—N12	98.2 (2)
C34—C35—C36—C37	−2.9 (5)	C31—N32—Ti1—N12	−95.9 (2)
C35—C36—C37—C38	1.3 (5)	C33—N32—Ti1—N22	165.8 (2)
C36—C37—C38—C39	1.2 (4)	C31—N32—Ti1—N22	−28.3 (2)
C37—C38—C39—C34	−1.9 (4)	C33—N32—Ti1—N1	31.4 (2)
C37—C38—C39—C31	173.4 (3)	C31—N32—Ti1—N1	−162.7 (2)
C35—C34—C39—C38	0.2 (4)	C33—N32—Ti1—C41	−80.9 (2)
C33—C34—C39—C38	176.8 (3)	C31—N32—Ti1—C41	85.0 (2)
C35—C34—C39—C31	−176.1 (3)	C11—N12—Ti1—N49	45.1 (2)
C33—C34—C39—C31	0.5 (3)	C13—N12—Ti1—N49	−110.8 (2)
N30—C31—C39—C38	−1.0 (5)	C11—N12—Ti1—N42	113.2 (2)
N32—C31—C39—C38	−178.1 (3)	C13—N12—Ti1—N42	−42.6 (2)
N30—C31—C39—C34	174.8 (3)	C11—N12—Ti1—N32	−100.0 (2)
N32—C31—C39—C34	−2.3 (3)	C13—N12—Ti1—N32	104.1 (2)
C48—C43—C44—C45	3.0 (4)	C11—N12—Ti1—N22	−167.9 (2)
N42—C43—C44—C45	−173.5 (2)	C13—N12—Ti1—N22	36.3 (2)
C43—C44—C45—C46	−1.9 (4)	C11—N12—Ti1—N1	−33.2 (2)
C44—C45—C46—C47	−0.5 (4)	C13—N12—Ti1—N1	171.0 (2)
C45—C46—C47—C48	1.8 (5)	C11—N12—Ti1—C41	79.2 (2)
C44—C43—C48—C47	−1.7 (4)	C13—N12—Ti1—C41	−76.7 (2)
N42—C43—C48—C47	174.8 (3)	C21—N22—Ti1—N49	70.9 (3)
C46—C47—C48—C43	−0.7 (5)	C23—N22—Ti1—N49	−82.7 (3)
C55—C50—C51—C52	2.7 (4)	C21—N22—Ti1—N42	73.0 (2)
N49—C50—C51—C52	−174.1 (2)	C23—N22—Ti1—N42	−80.7 (2)
C50—C51—C52—C53	−1.6 (4)	C21—N22—Ti1—N32	−176.4 (2)
C51—C52—C53—C54	−0.6 (4)	C23—N22—Ti1—N32	30.0 (2)
C52—C53—C54—C55	1.7 (4)	C21—N22—Ti1—N12	−34.2 (2)
C51—C50—C55—C54	−1.7 (4)	C23—N22—Ti1—N12	172.2 (2)
N49—C50—C55—C54	175.2 (2)	C21—N22—Ti1—N1	−104.8 (2)
C53—C54—C55—C50	−0.6 (4)	C23—N22—Ti1—N1	101.6 (2)
N10—C9—N1—C2	−176.8 (2)	C21—N22—Ti1—C41	70.0 (2)
C8—C9—N1—C2	−0.4 (3)	C23—N22—Ti1—C41	−83.6 (2)
N10—C9—N1—Ti1	−24.8 (4)	C9—N1—Ti1—N49	−74.0 (2)
C8—C9—N1—Ti1	151.65 (18)	C2—N1—Ti1—N49	73.63 (19)
N40—C2—N1—C9	−177.0 (2)	C9—N1—Ti1—N42	−72.3 (3)
C3—C2—N1—C9	1.4 (3)	C2—N1—Ti1—N42	75.3 (2)
N40—C2—N1—Ti1	30.5 (3)	C9—N1—Ti1—N32	175.5 (2)
C3—C2—N1—Ti1	−151.09 (17)	C2—N1—Ti1—N32	−36.80 (19)
N1—C9—N10—C11	0.3 (4)	C9—N1—Ti1—N12	33.0 (2)
C8—C9—N10—C11	−175.7 (3)	C2—N1—Ti1—N12	−179.3 (2)
N12—C11—N10—C9	0.3 (4)	C9—N1—Ti1—N22	103.6 (2)
C19—C11—N10—C9	−179.1 (2)	C2—N1—Ti1—N22	−108.8 (2)
N10—C11—N12—C13	−176.1 (3)	C9—N1—Ti1—C41	−71.3 (2)
C19—C11—N12—C13	3.4 (3)	C2—N1—Ti1—C41	76.4 (2)
N10—C11—N12—Ti1	24.6 (4)	O41—C41—Ti1—N49	78 (3)
C19—C11—N12—Ti1	−155.90 (18)	N42—C41—Ti1—N49	−173.8 (3)
N20—C13—N12—C11	173.0 (3)	O41—C41—Ti1—N42	−108 (3)
C14—C13—N12—C11	−4.3 (3)	N49—C41—Ti1—N42	173.8 (3)
N20—C13—N12—Ti1	−27.3 (4)	O41—C41—Ti1—N32	164 (3)
C14—C13—N12—Ti1	155.39 (18)	N42—C41—Ti1—N32	−87.35 (17)
N12—C13—N20—C21	−1.8 (4)	N49—C41—Ti1—N32	86.49 (17)
C14—C13—N20—C21	175.2 (3)	O41—C41—Ti1—N12	−15 (3)
N22—C21—N20—C13	4.1 (4)	N42—C41—Ti1—N12	93.24 (17)
C29—C21—N20—C13	−176.3 (3)	N49—C41—Ti1—N12	−92.93 (16)
N20—C21—N22—C23	179.9 (3)	O41—C41—Ti1—N22	−103 (3)
C29—C21—N22—C23	0.3 (3)	N42—C41—Ti1—N22	5.32 (18)
N20—C21—N22—Ti1	22.3 (4)	N49—C41—Ti1—N22	179.15 (15)
C29—C21—N22—Ti1	−157.37 (17)	O41—C41—Ti1—N1	73 (3)
N30—C23—N22—C21	−179.3 (2)	N42—C41—Ti1—N1	−178.91 (15)
C24—C23—N22—C21	−0.7 (3)	N49—C41—Ti1—N1	−5.08 (18)