2,3,4,6-Tetra­phenyl-2H-pyrazolo­[3,4-d]­pyridazin-7(6H)-one

The title compound, C₂₉H₂₀N₄O, is a derivative of 2H-pyrazolo­[3,4-d]­pyridazine and is non-planar, although consisting of planar fragments. The structure consists of planar fragments. There are two independent mol­ecules in the asymmetric unit. The dihedral angle between the fused pyridazine and pyrazole rings is 2.61 (11)° in mol­ecule A [3.19 (11)° in mol­ecule B]. The crystal structure is stabilized by intramolecular and intermolecular C—H...O interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.050
• wR factor = 0.089
• Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.138
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.14
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         49 Perc.

   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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 1997; software used to prepare material for publication: WinGX (Farrugia, 1999).

2,3,4,6-Tetraphenyl-2H-pyrazolo[3,4-d]pyridazin-7(6H)-one

Crystal data

C29H20N4O	Z = 4
Mr = 440.49	F(000) = 920
Triclinic, P1	Dx = 1.315 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2616 (12) Å	Cell parameters from 15351 reflections
b = 10.5057 (12) Å	θ = 1.9–26.9°
c = 21.264 (2) Å	µ = 0.08 mm^−1
α = 95.064 (9)°	T = 293 K
β = 93.438 (9)°	Prism, colourless
γ = 102.158 (9)°	0.50 × 0.33 × 0.23 mm
V = 2225.0 (4) Å^3

Data collection

Stoe IPDS 2 diffractometer	3864 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube	Rint = 0.138
Plane graphite monochromator	θmax = 25.0°, θmin = 1.9°
Detector resolution: 6.67 pixels mm^-1	h = −12→11
w rotation scans	k = −12→12
28743 measured reflections	l = −25→25
7844 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)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.089	w = 1/[σ^2(Fo^2) + (0.0101P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.81	(Δ/σ)max < 0.001
7844 reflections	Δρmax = 0.31 e Å^−3
614 parameters	Δρmin = −0.24 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: 0.0137 (8)

Special details

Experimental. Experiments were followed by thin-layer chromatography using DC Alufolien Kieselgel 60 F₂₅₄ Merck and Camag TLC lamp (254/366 nm). After completion of the reactions, solvents were evaporated with a rotary evaporator (Buchi RE model 111). Melting point was determined on an Electrothermal 9200 apparatus and is uncorrected. Microanalysis was performed with a Carlo Erba Elemental Analyser Model 1108.

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
O1A	0.37948 (17)	0.21835 (16)	0.46585 (8)	0.0755 (5)
N1A	0.35737 (17)	0.41939 (18)	0.43884 (8)	0.0519 (4)
N2A	0.31799 (17)	0.53729 (17)	0.45070 (8)	0.0546 (5)
N3A	0.23610 (17)	0.26289 (18)	0.57472 (8)	0.0564 (5)
N4A	0.17278 (17)	0.32908 (18)	0.61639 (8)	0.0543 (5)
C1A	0.2584 (2)	0.5605 (2)	0.50130 (10)	0.0492 (5)
C2A	0.2310 (2)	0.4653 (2)	0.54599 (9)	0.0476 (5)
C3A	0.2707 (2)	0.3475 (2)	0.53251 (10)	0.0505 (5)
C4A	0.3398 (2)	0.3188 (2)	0.47758 (10)	0.0550 (6)
C5A	0.1679 (2)	0.4527 (2)	0.60165 (9)	0.0493 (5)
C6A	0.4153 (2)	0.4100 (2)	0.37880 (10)	0.0567 (6)
C7A	0.4088 (3)	0.2904 (3)	0.34444 (11)	0.0757 (7)
H7A	0.3705	0.2131	0.3606	0.091*
C8A	0.4601 (3)	0.2872 (4)	0.28538 (12)	0.0931 (9)
H8A	0.4570	0.2070	0.2623	0.112*
C9A	0.5147 (3)	0.3995 (4)	0.26101 (13)	0.0952 (10)
H9A	0.5487	0.3961	0.2215	0.114*
C10A	0.5199 (3)	0.5173 (3)	0.29458 (13)	0.0815 (8)
H10A	0.5568	0.5941	0.2775	0.098*
C11A	0.4710 (2)	0.5241 (3)	0.35347 (11)	0.0649 (6)
H11A	0.4754	0.6050	0.3761	0.078*
C12A	0.2203 (2)	0.6896 (2)	0.50708 (9)	0.0496 (5)
C13A	0.3130 (2)	0.8007 (2)	0.49783 (11)	0.0646 (6)
H13A	0.3987	0.7944	0.4880	0.078*
C14A	0.2788 (3)	0.9216 (2)	0.50313 (11)	0.0696 (7)
H14A	0.3415	0.9963	0.4968	0.083*
C15A	0.1534 (3)	0.9312 (2)	0.51755 (10)	0.0662 (7)
H15A	0.1312	1.0127	0.5214	0.079*
C16A	0.0599 (2)	0.8215 (2)	0.52642 (10)	0.0626 (6)
H16A	−0.0255	0.8287	0.5363	0.075*
C17A	0.0929 (2)	0.7001 (2)	0.52064 (9)	0.0550 (6)
H17A	0.0291	0.6254	0.5259	0.066*
C18A	0.1001 (2)	0.5386 (2)	0.63991 (9)	0.0530 (6)
C19A	0.1673 (2)	0.6654 (2)	0.66179 (10)	0.0615 (6)
H19A	0.2565	0.6943	0.6542	0.074*
C20A	0.1012 (3)	0.7489 (3)	0.69489 (10)	0.0764 (8)
H20A	0.1458	0.8341	0.7091	0.092*
C21A	−0.0292 (3)	0.7061 (3)	0.70662 (12)	0.0839 (9)
H21A	−0.0728	0.7621	0.7293	0.101*
C22A	−0.0964 (3)	0.5816 (3)	0.68538 (12)	0.0786 (8)
H22A	−0.1852	0.5533	0.6937	0.094*
C23A	−0.0326 (2)	0.4977 (3)	0.65161 (10)	0.0638 (6)
H23A	−0.0791	0.4135	0.6367	0.077*
C24A	0.1163 (2)	0.2624 (2)	0.66758 (10)	0.0574 (6)
C25A	0.1423 (2)	0.3189 (3)	0.72939 (11)	0.0688 (7)
H25A	0.1961	0.4023	0.7389	0.083*
C26A	0.0862 (3)	0.2485 (4)	0.77709 (12)	0.0834 (9)
H26A	0.1028	0.2848	0.8190	0.100*
C27A	0.0070 (3)	0.1263 (4)	0.76277 (15)	0.0909 (9)
H27A	−0.0305	0.0802	0.7950	0.109*
C28A	−0.0176 (3)	0.0715 (3)	0.70144 (15)	0.0866 (8)
H28A	−0.0711	−0.0120	0.6921	0.104*
C29A	0.0366 (2)	0.1395 (3)	0.65326 (12)	0.0731 (7)
H29A	0.0193	0.1025	0.6114	0.088*
O1B	0.24279 (16)	0.40437 (18)	−0.07833 (7)	0.0754 (5)
N1B	0.35184 (17)	0.36119 (18)	0.01190 (8)	0.0560 (5)
N2B	0.45216 (17)	0.31407 (19)	0.04302 (8)	0.0556 (5)
N3B	0.40763 (18)	0.2659 (2)	−0.14961 (8)	0.0597 (5)
N4B	0.50580 (18)	0.19895 (19)	−0.15988 (8)	0.0571 (5)
C1B	0.5332 (2)	0.2576 (2)	0.01165 (10)	0.0514 (5)
C2B	0.5190 (2)	0.2408 (2)	−0.05663 (10)	0.0509 (5)
C3B	0.4175 (2)	0.2898 (2)	−0.08684 (10)	0.0535 (6)
C4B	0.3282 (2)	0.3574 (2)	−0.05369 (10)	0.0568 (6)
C5B	0.5773 (2)	0.1825 (2)	−0.10587 (10)	0.0525 (6)
C6B	0.2680 (2)	0.4124 (2)	0.05542 (10)	0.0561 (6)
C7B	0.1340 (2)	0.4032 (3)	0.04005 (12)	0.0736 (7)
H7B	0.0955	0.3672	0.0000	0.088*
C8B	0.0572 (3)	0.4479 (3)	0.08464 (15)	0.0902 (9)
H8B	−0.0330	0.4435	0.0741	0.108*
C9B	0.1123 (3)	0.4984 (3)	0.14395 (13)	0.0884 (9)
H9B	0.0596	0.5272	0.1738	0.106*
C10B	0.2439 (3)	0.5065 (3)	0.15914 (12)	0.0776 (8)
H10B	0.2814	0.5408	0.1996	0.093*
C11B	0.3223 (2)	0.4644 (2)	0.11535 (11)	0.0649 (6)
H11B	0.4128	0.4710	0.1262	0.078*
C12B	0.6295 (2)	0.2115 (2)	0.05350 (10)	0.0526 (6)
C13B	0.6886 (2)	0.2906 (3)	0.10759 (10)	0.0652 (7)
H13B	0.6716	0.3739	0.1153	0.078*
C14B	0.7721 (3)	0.2477 (3)	0.15012 (12)	0.0803 (8)
H14B	0.8105	0.3020	0.1863	0.096*
C15B	0.7990 (2)	0.1254 (3)	0.13953 (12)	0.0751 (8)
H15B	0.8553	0.0967	0.1684	0.090*
C16B	0.7419 (2)	0.0459 (3)	0.08585 (11)	0.0668 (7)
H16B	0.7598	−0.0370	0.0784	0.080*
C17B	0.6578 (2)	0.0882 (2)	0.04271 (10)	0.0590 (6)
H17B	0.6202	0.0338	0.0064	0.071*
C18B	0.6828 (2)	0.1070 (2)	−0.10563 (10)	0.0543 (6)
C19B	0.8094 (2)	0.1647 (3)	−0.07877 (11)	0.0673 (7)
H19B	0.8306	0.2535	−0.0646	0.081*
C20B	0.9053 (3)	0.0901 (4)	−0.07298 (13)	0.0823 (8)
H20B	0.9905	0.1290	−0.0547	0.099*
C21B	0.8752 (3)	−0.0403 (4)	−0.09398 (14)	0.0898 (9)
H21B	0.9391	−0.0904	−0.0891	0.108*
C22B	0.7502 (3)	−0.0969 (3)	−0.12222 (12)	0.0823 (8)
H22B	0.7303	−0.1851	−0.1375	0.099*
C23B	0.6548 (3)	−0.0244 (3)	−0.12800 (11)	0.0665 (6)
H23B	0.5703	−0.0638	−0.1471	0.080*
C24B	0.5173 (2)	0.1525 (2)	−0.22502 (10)	0.0596 (6)
C25B	0.6396 (3)	0.1655 (3)	−0.24912 (11)	0.0744 (7)
H25B	0.7180	0.2014	−0.2237	0.089*
C26B	0.6432 (3)	0.1231 (3)	−0.31322 (13)	0.0905 (9)
H26B	0.7250	0.1313	−0.3308	0.109*
C27B	0.5282 (3)	0.0700 (3)	−0.35002 (13)	0.0954 (10)
H27B	0.5319	0.0412	−0.3924	0.114*
C28B	0.4071 (3)	0.0587 (3)	−0.32494 (12)	0.0892 (9)
H28B	0.3288	0.0226	−0.3503	0.107*
C29B	0.4008 (3)	0.1005 (3)	−0.26228 (11)	0.0727 (7)
H29B	0.3185	0.0936	−0.2453	0.087*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.1014 (13)	0.0495 (11)	0.0873 (12)	0.0349 (10)	0.0306 (9)	0.0100 (9)
N1A	0.0605 (11)	0.0426 (11)	0.0559 (11)	0.0178 (9)	0.0120 (9)	0.0025 (9)
N2A	0.0640 (12)	0.0406 (11)	0.0614 (12)	0.0170 (9)	0.0087 (9)	0.0016 (9)
N3A	0.0671 (12)	0.0436 (11)	0.0615 (11)	0.0173 (10)	0.0126 (9)	0.0037 (10)
N4A	0.0613 (11)	0.0487 (12)	0.0549 (11)	0.0158 (10)	0.0077 (9)	0.0055 (9)
C1A	0.0534 (13)	0.0379 (13)	0.0559 (13)	0.0123 (11)	0.0011 (11)	−0.0005 (10)
C2A	0.0526 (13)	0.0414 (13)	0.0489 (13)	0.0127 (11)	0.0012 (10)	0.0007 (10)
C3A	0.0564 (13)	0.0403 (13)	0.0564 (13)	0.0146 (11)	0.0050 (11)	0.0038 (11)
C4A	0.0589 (14)	0.0454 (15)	0.0632 (14)	0.0173 (12)	0.0082 (11)	0.0029 (12)
C5A	0.0539 (13)	0.0433 (13)	0.0515 (13)	0.0147 (11)	−0.0003 (11)	0.0026 (10)
C6A	0.0575 (14)	0.0597 (16)	0.0552 (14)	0.0199 (12)	0.0052 (11)	0.0002 (12)
C7A	0.0967 (19)	0.0655 (18)	0.0679 (17)	0.0294 (16)	0.0104 (14)	−0.0072 (13)
C8A	0.134 (3)	0.094 (3)	0.0634 (18)	0.057 (2)	0.0176 (17)	−0.0088 (16)
C9A	0.104 (2)	0.141 (3)	0.0616 (17)	0.066 (2)	0.0237 (16)	0.018 (2)
C10A	0.0718 (17)	0.107 (3)	0.0777 (19)	0.0339 (18)	0.0232 (14)	0.0257 (18)
C11A	0.0607 (14)	0.0692 (18)	0.0667 (16)	0.0156 (13)	0.0091 (12)	0.0112 (13)
C12A	0.0597 (14)	0.0399 (13)	0.0505 (12)	0.0159 (12)	0.0005 (10)	0.0026 (10)
C13A	0.0699 (16)	0.0468 (15)	0.0796 (16)	0.0158 (13)	0.0121 (12)	0.0075 (12)
C14A	0.0818 (18)	0.0402 (15)	0.0871 (18)	0.0138 (14)	0.0066 (14)	0.0079 (13)
C15A	0.0878 (18)	0.0476 (16)	0.0685 (15)	0.0312 (15)	−0.0022 (13)	0.0016 (12)
C16A	0.0705 (16)	0.0600 (17)	0.0636 (15)	0.0308 (15)	−0.0007 (12)	0.0039 (12)
C17A	0.0607 (14)	0.0462 (14)	0.0587 (13)	0.0166 (12)	−0.0047 (11)	0.0028 (11)
C18A	0.0580 (14)	0.0541 (15)	0.0499 (12)	0.0215 (12)	0.0005 (10)	0.0020 (11)
C19A	0.0731 (16)	0.0598 (17)	0.0522 (13)	0.0221 (14)	−0.0034 (11)	−0.0042 (12)
C20A	0.109 (2)	0.0627 (17)	0.0595 (15)	0.0315 (17)	0.0016 (15)	−0.0103 (13)
C21A	0.107 (2)	0.091 (2)	0.0677 (17)	0.054 (2)	0.0154 (16)	−0.0013 (16)
C22A	0.0676 (16)	0.107 (3)	0.0717 (17)	0.0405 (18)	0.0134 (13)	0.0112 (17)
C23A	0.0639 (16)	0.0679 (17)	0.0623 (14)	0.0225 (14)	0.0035 (12)	0.0020 (12)
C24A	0.0654 (14)	0.0584 (16)	0.0546 (14)	0.0217 (13)	0.0121 (11)	0.0149 (12)
C25A	0.0714 (16)	0.0798 (19)	0.0587 (15)	0.0262 (15)	0.0030 (13)	0.0041 (14)
C26A	0.092 (2)	0.113 (3)	0.0589 (16)	0.048 (2)	0.0146 (15)	0.0192 (18)
C27A	0.101 (2)	0.101 (3)	0.088 (2)	0.041 (2)	0.0371 (18)	0.040 (2)
C28A	0.101 (2)	0.0668 (19)	0.098 (2)	0.0182 (17)	0.0339 (17)	0.0251 (18)
C29A	0.0913 (18)	0.0580 (18)	0.0715 (16)	0.0139 (15)	0.0210 (14)	0.0105 (14)
O1B	0.0805 (11)	0.0882 (14)	0.0693 (10)	0.0483 (11)	−0.0016 (9)	0.0062 (9)
N1B	0.0572 (11)	0.0554 (12)	0.0591 (12)	0.0217 (10)	0.0047 (9)	0.0035 (9)
N2B	0.0538 (11)	0.0564 (12)	0.0594 (11)	0.0193 (10)	0.0044 (9)	0.0047 (9)
N3B	0.0623 (12)	0.0637 (13)	0.0583 (12)	0.0257 (11)	0.0065 (9)	0.0040 (10)
N4B	0.0644 (12)	0.0588 (13)	0.0501 (11)	0.0181 (10)	0.0062 (9)	0.0041 (9)
C1B	0.0527 (13)	0.0494 (14)	0.0535 (13)	0.0138 (11)	0.0053 (11)	0.0063 (11)
C2B	0.0525 (13)	0.0466 (13)	0.0552 (14)	0.0137 (11)	0.0050 (11)	0.0064 (11)
C3B	0.0585 (14)	0.0506 (14)	0.0528 (14)	0.0139 (12)	0.0049 (11)	0.0079 (11)
C4B	0.0600 (14)	0.0560 (15)	0.0562 (15)	0.0182 (12)	0.0013 (11)	0.0038 (11)
C5B	0.0530 (13)	0.0524 (14)	0.0545 (13)	0.0159 (11)	0.0036 (11)	0.0076 (11)
C6B	0.0606 (15)	0.0497 (14)	0.0618 (15)	0.0185 (12)	0.0115 (12)	0.0053 (11)
C7B	0.0624 (16)	0.083 (2)	0.0799 (17)	0.0282 (15)	0.0094 (13)	0.0028 (14)
C8B	0.0745 (18)	0.109 (3)	0.103 (2)	0.0447 (19)	0.0248 (17)	0.025 (2)
C9B	0.106 (2)	0.097 (2)	0.080 (2)	0.055 (2)	0.0338 (17)	0.0122 (17)
C10B	0.093 (2)	0.074 (2)	0.0716 (17)	0.0316 (17)	0.0182 (15)	−0.0013 (14)
C11B	0.0699 (15)	0.0583 (16)	0.0678 (16)	0.0174 (13)	0.0088 (13)	0.0033 (13)
C12B	0.0516 (13)	0.0604 (16)	0.0486 (13)	0.0151 (12)	0.0078 (10)	0.0114 (11)
C13B	0.0741 (16)	0.0678 (17)	0.0559 (14)	0.0225 (14)	0.0011 (12)	0.0041 (13)
C14B	0.093 (2)	0.086 (2)	0.0630 (16)	0.0298 (18)	−0.0134 (14)	0.0020 (15)
C15B	0.0724 (17)	0.092 (2)	0.0668 (17)	0.0288 (16)	−0.0012 (13)	0.0183 (16)
C16B	0.0674 (16)	0.0646 (17)	0.0756 (16)	0.0245 (14)	0.0108 (13)	0.0186 (14)
C17B	0.0552 (14)	0.0605 (16)	0.0641 (14)	0.0169 (12)	0.0082 (11)	0.0092 (12)
C18B	0.0568 (14)	0.0580 (16)	0.0529 (13)	0.0200 (13)	0.0112 (11)	0.0098 (11)
C19B	0.0606 (16)	0.0712 (18)	0.0742 (16)	0.0214 (14)	0.0079 (12)	0.0107 (13)
C20B	0.0589 (16)	0.105 (3)	0.0902 (19)	0.0284 (18)	0.0121 (14)	0.0215 (18)
C21B	0.090 (2)	0.103 (3)	0.101 (2)	0.056 (2)	0.0392 (18)	0.040 (2)
C22B	0.104 (2)	0.0594 (18)	0.097 (2)	0.0375 (18)	0.0336 (18)	0.0171 (15)
C23B	0.0738 (16)	0.0570 (17)	0.0719 (16)	0.0200 (14)	0.0139 (12)	0.0052 (13)
C24B	0.0708 (16)	0.0629 (16)	0.0503 (13)	0.0248 (13)	0.0087 (13)	0.0075 (12)
C25B	0.0714 (17)	0.088 (2)	0.0685 (17)	0.0259 (15)	0.0111 (13)	0.0071 (14)
C26B	0.089 (2)	0.118 (3)	0.0716 (19)	0.033 (2)	0.0264 (16)	0.0118 (18)
C27B	0.110 (2)	0.125 (3)	0.0569 (16)	0.042 (2)	0.0066 (18)	−0.0038 (17)
C28B	0.095 (2)	0.113 (3)	0.0592 (17)	0.0289 (19)	0.0013 (15)	−0.0051 (16)
C29B	0.0721 (16)	0.087 (2)	0.0587 (16)	0.0192 (15)	0.0017 (13)	0.0036 (14)

Geometric parameters (Å, º)

O1A—C4A	1.220 (2)	O1B—C4B	1.208 (2)
N1A—C4A	1.385 (3)	N1B—N2B	1.390 (2)
N1A—N2A	1.389 (2)	N1B—C4B	1.397 (3)
N1A—C6A	1.444 (3)	N1B—C6B	1.445 (3)
N2A—C1A	1.299 (3)	N2B—C1B	1.301 (3)
N3A—C3A	1.330 (2)	N3B—C3B	1.330 (3)
N3A—N4A	1.357 (2)	N3B—N4B	1.362 (2)
N4A—C5A	1.372 (3)	N4B—C5B	1.369 (2)
N4A—C24A	1.432 (3)	N4B—C24B	1.448 (3)
C1A—C2A	1.437 (3)	C1B—C2B	1.442 (3)
C1A—C12A	1.485 (3)	C1B—C12B	1.475 (2)
C2A—C5A	1.386 (3)	C2B—C5B	1.395 (3)
C2A—C3A	1.394 (3)	C2B—C3B	1.403 (3)
C3A—C4A	1.444 (3)	C3B—C4B	1.450 (3)
C5A—C18A	1.471 (3)	C5B—C18B	1.471 (3)
C6A—C7A	1.383 (3)	C6B—C7B	1.375 (3)
C6A—C11A	1.384 (3)	C6B—C11B	1.377 (3)
C7A—C8A	1.391 (4)	C7B—C8B	1.381 (4)
C7A—H7A	0.9300	C7B—H7B	0.9300
C8A—C9A	1.356 (4)	C8B—C9B	1.364 (4)
C8A—H8A	0.9300	C8B—H8B	0.9300
C9A—C10A	1.362 (4)	C9B—C10B	1.353 (3)
C9A—H9A	0.9300	C9B—H9B	0.9300
C10A—C11A	1.378 (3)	C10B—C11B	1.370 (3)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.379 (3)	C12B—C13B	1.384 (3)
C12A—C17A	1.380 (3)	C12B—C17B	1.388 (3)
C13A—C14A	1.384 (3)	C13B—C14B	1.377 (3)
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—C15A	1.362 (3)	C14B—C15B	1.372 (4)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—C16A	1.371 (3)	C15B—C16B	1.375 (4)
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—C17A	1.384 (3)	C16B—C17B	1.386 (3)
C16A—H16A	0.9300	C16B—H16B	0.9300
C17A—H17A	0.9300	C17B—H17B	0.9300
C18A—C23A	1.384 (3)	C18B—C19B	1.378 (3)
C18A—C19A	1.390 (3)	C18B—C23B	1.384 (3)
C19A—C20A	1.387 (3)	C19B—C20B	1.387 (3)
C19A—H19A	0.9300	C19B—H19B	0.9300
C20A—C21A	1.364 (4)	C20B—C21B	1.367 (4)
C20A—H20A	0.9300	C20B—H20B	0.9300
C21A—C22A	1.367 (4)	C21B—C22B	1.372 (4)
C21A—H21A	0.9300	C21B—H21B	0.9300
C22A—C23A	1.381 (3)	C22B—C23B	1.368 (3)
C22A—H22A	0.9300	C22B—H22B	0.9300
C23A—H23A	0.9300	C23B—H23B	0.9300
C24A—C29A	1.373 (4)	C24B—C25B	1.368 (3)
C24A—C25A	1.380 (3)	C24B—C29B	1.375 (3)
C25A—C26A	1.390 (3)	C25B—C26B	1.401 (4)
C25A—H25A	0.9300	C25B—H25B	0.9300
C26A—C27A	1.364 (4)	C26B—C27B	1.361 (4)
C26A—H26A	0.9300	C26B—H26B	0.9300
C27A—C28A	1.365 (4)	C27B—C28B	1.368 (4)
C27A—H27A	0.9300	C27B—H27B	0.9300
C28A—C29A	1.378 (3)	C28B—C29B	1.375 (3)
C28A—H28A	0.9300	C28B—H28B	0.9300
C29A—H29A	0.9300	C29B—H29B	0.9300
C4A—N1A—N2A	125.42 (18)	N2B—N1B—C4B	125.68 (18)
C4A—N1A—C6A	122.71 (19)	N2B—N1B—C6B	112.21 (16)
N2A—N1A—C6A	111.82 (17)	C4B—N1B—C6B	122.08 (17)
C1A—N2A—N1A	120.41 (17)	C1B—N2B—N1B	121.21 (17)
C3A—N3A—N4A	103.03 (17)	C3B—N3B—N4B	102.67 (15)
N3A—N4A—C5A	113.76 (17)	N3B—N4B—C5B	114.18 (17)
N3A—N4A—C24A	117.73 (18)	N3B—N4B—C24B	116.38 (16)
C5A—N4A—C24A	128.47 (19)	C5B—N4B—C24B	129.42 (19)
N2A—C1A—C2A	121.09 (19)	N2B—C1B—C2B	120.23 (17)
N2A—C1A—C12A	114.33 (19)	N2B—C1B—C12B	112.60 (18)
C2A—C1A—C12A	124.6 (2)	C2B—C1B—C12B	127.1 (2)
C5A—C2A—C3A	105.32 (18)	C5B—C2B—C3B	104.67 (17)
C5A—C2A—C1A	137.5 (2)	C5B—C2B—C1B	137.89 (19)
C3A—C2A—C1A	117.2 (2)	C3B—C2B—C1B	117.4 (2)
N3A—C3A—C2A	113.2 (2)	N3B—C3B—C2B	113.6 (2)
N3A—C3A—C4A	123.3 (2)	N3B—C3B—C4B	122.29 (18)
C2A—C3A—C4A	123.6 (2)	C2B—C3B—C4B	124.1 (2)
O1A—C4A—N1A	122.9 (2)	O1B—C4B—N1B	123.1 (2)
O1A—C4A—C3A	124.8 (2)	O1B—C4B—C3B	125.6 (2)
N1A—C4A—C3A	112.32 (19)	N1B—C4B—C3B	111.32 (18)
N4A—C5A—C2A	104.72 (19)	N4B—C5B—C2B	104.84 (17)
N4A—C5A—C18A	122.10 (19)	N4B—C5B—C18B	123.30 (19)
C2A—C5A—C18A	133.11 (19)	C2B—C5B—C18B	131.64 (18)
C7A—C6A—C11A	119.5 (2)	C7B—C6B—C11B	119.2 (2)
C7A—C6A—N1A	121.6 (2)	C7B—C6B—N1B	121.9 (2)
C11A—C6A—N1A	118.8 (2)	C11B—C6B—N1B	118.83 (19)
C6A—C7A—C8A	119.3 (3)	C6B—C7B—C8B	119.4 (3)
C6A—C7A—H7A	120.4	C6B—C7B—H7B	120.3
C8A—C7A—H7A	120.4	C8B—C7B—H7B	120.3
C9A—C8A—C7A	120.8 (3)	C9B—C8B—C7B	120.7 (3)
C9A—C8A—H8A	119.6	C9B—C8B—H8B	119.6
C7A—C8A—H8A	119.6	C7B—C8B—H8B	119.6
C8A—C9A—C10A	119.9 (3)	C10B—C9B—C8B	119.8 (3)
C8A—C9A—H9A	120.1	C10B—C9B—H9B	120.1
C10A—C9A—H9A	120.1	C8B—C9B—H9B	120.1
C9A—C10A—C11A	120.8 (3)	C9B—C10B—C11B	120.4 (3)
C9A—C10A—H10A	119.6	C9B—C10B—H10B	119.8
C11A—C10A—H10A	119.6	C11B—C10B—H10B	119.8
C10A—C11A—C6A	119.7 (3)	C10B—C11B—C6B	120.5 (2)
C10A—C11A—H11A	120.1	C10B—C11B—H11B	119.8
C6A—C11A—H11A	120.1	C6B—C11B—H11B	119.8
C13A—C12A—C17A	119.3 (2)	C13B—C12B—C17B	118.39 (18)
C13A—C12A—C1A	119.6 (2)	C13B—C12B—C1B	119.0 (2)
C17A—C12A—C1A	121.1 (2)	C17B—C12B—C1B	122.5 (2)
C12A—C13A—C14A	120.1 (2)	C14B—C13B—C12B	120.9 (2)
C12A—C13A—H13A	119.9	C14B—C13B—H13B	119.5
C14A—C13A—H13A	119.9	C12B—C13B—H13B	119.6
C15A—C14A—C13A	120.1 (2)	C15B—C14B—C13B	120.6 (3)
C15A—C14A—H14A	119.9	C15B—C14B—H14B	119.7
C13A—C14A—H14A	119.9	C13B—C14B—H14B	119.7
C14A—C15A—C16A	120.4 (2)	C14B—C15B—C16B	119.3 (2)
C14A—C15A—H15A	119.8	C14B—C15B—H15B	120.4
C16A—C15A—H15A	119.8	C16B—C15B—H15B	120.4
C15A—C16A—C17A	119.8 (2)	C15B—C16B—C17B	120.6 (2)
C15A—C16A—H16A	120.1	C15B—C16B—H16B	119.7
C17A—C16A—H16A	120.1	C17B—C16B—H16B	119.7
C12A—C17A—C16A	120.2 (2)	C16B—C17B—C12B	120.2 (2)
C12A—C17A—H17A	119.9	C16B—C17B—H17B	119.9
C16A—C17A—H17A	119.9	C12B—C17B—H17B	119.9
C23A—C18A—C19A	119.1 (2)	C19B—C18B—C23B	119.1 (2)
C23A—C18A—C5A	120.9 (2)	C19B—C18B—C5B	119.8 (2)
C19A—C18A—C5A	119.9 (2)	C23B—C18B—C5B	120.9 (2)
C20A—C19A—C18A	119.9 (2)	C18B—C19B—C20B	119.8 (3)
C20A—C19A—H19A	120.0	C18B—C19B—H19B	120.1
C18A—C19A—H19A	120.0	C20B—C19B—H19B	120.1
C21A—C20A—C19A	120.0 (3)	C21B—C20B—C19B	120.5 (3)
C21A—C20A—H20A	120.0	C21B—C20B—H20B	119.8
C19A—C20A—H20A	120.0	C19B—C20B—H20B	119.8
C20A—C21A—C22A	120.6 (3)	C20B—C21B—C22B	119.7 (3)
C20A—C21A—H21A	119.7	C20B—C21B—H21B	120.2
C22A—C21A—H21A	119.7	C22B—C21B—H21B	120.2
C21A—C22A—C23A	120.2 (3)	C23B—C22B—C21B	120.4 (3)
C21A—C22A—H22A	119.9	C23B—C22B—H22B	119.8
C23A—C22A—H22A	119.9	C21B—C22B—H22B	119.8
C22A—C23A—C18A	120.2 (3)	C22B—C23B—C18B	120.6 (2)
C22A—C23A—H23A	119.9	C22B—C23B—H23B	119.7
C18A—C23A—H23A	119.9	C18B—C23B—H23B	119.7
C29A—C24A—C25A	121.0 (2)	C25B—C24B—C29B	121.5 (2)
C29A—C24A—N4A	117.8 (2)	C25B—C24B—N4B	121.0 (2)
C25A—C24A—N4A	121.2 (2)	C29B—C24B—N4B	117.5 (2)
C24A—C25A—C26A	118.5 (3)	C24B—C25B—C26B	118.0 (2)
C24A—C25A—H25A	120.8	C24B—C25B—H25B	121.0
C26A—C25A—H25A	120.8	C26B—C25B—H25B	121.0
C27A—C26A—C25A	120.4 (3)	C27B—C26B—C25B	120.7 (3)
C27A—C26A—H26A	119.8	C27B—C26B—H26B	119.7
C25A—C26A—H26A	119.8	C25B—C26B—H26B	119.7
C26A—C27A—C28A	120.4 (3)	C26B—C27B—C28B	120.2 (3)
C26A—C27A—H27A	119.8	C26B—C27B—H27B	119.9
C28A—C27A—H27A	119.8	C28B—C27B—H27B	119.9
C27A—C28A—C29A	120.3 (3)	C27B—C28B—C29B	120.2 (3)
C27A—C28A—H28A	119.9	C27B—C28B—H28B	119.9
C29A—C28A—H28A	119.9	C29B—C28B—H28B	119.9
C24A—C29A—C28A	119.4 (3)	C24B—C29B—C28B	119.4 (2)
C24A—C29A—H29A	120.3	C24B—C29B—H29B	120.3
C28A—C29A—H29A	120.3	C28B—C29B—H29B	120.3
C4A—N1A—N2A—C1A	−0.5 (3)	C4B—N1B—N2B—C1B	−1.7 (3)
C6A—N1A—N2A—C1A	176.96 (18)	C6B—N1B—N2B—C1B	176.2 (2)
C3A—N3A—N4A—C5A	−0.5 (2)	C3B—N3B—N4B—C5B	−1.0 (2)
C3A—N3A—N4A—C24A	177.28 (17)	C3B—N3B—N4B—C24B	177.3 (2)
N1A—N2A—C1A—C2A	−0.3 (3)	N1B—N2B—C1B—C2B	−1.0 (3)
N1A—N2A—C1A—C12A	−179.07 (16)	N1B—N2B—C1B—C12B	−178.36 (18)
N2A—C1A—C2A—C5A	−177.1 (2)	N2B—C1B—C2B—C5B	−175.9 (3)
C12A—C1A—C2A—C5A	1.5 (4)	C12B—C1B—C2B—C5B	1.0 (4)
N2A—C1A—C2A—C3A	−0.2 (3)	N2B—C1B—C2B—C3B	1.3 (3)
C12A—C1A—C2A—C3A	178.42 (19)	C12B—C1B—C2B—C3B	178.2 (2)
N4A—N3A—C3A—C2A	−0.2 (2)	N4B—N3B—C3B—C2B	0.2 (2)
N4A—N3A—C3A—C4A	−178.86 (19)	N4B—N3B—C3B—C4B	−178.3 (2)
C5A—C2A—C3A—N3A	0.8 (2)	C5B—C2B—C3B—N3B	0.6 (3)
C1A—C2A—C3A—N3A	−177.10 (17)	C1B—C2B—C3B—N3B	−177.49 (19)
C5A—C2A—C3A—C4A	179.43 (19)	C5B—C2B—C3B—C4B	179.0 (2)
C1A—C2A—C3A—C4A	1.6 (3)	C1B—C2B—C3B—C4B	0.9 (3)
N2A—N1A—C4A—O1A	−178.0 (2)	N2B—N1B—C4B—O1B	−177.0 (2)
C6A—N1A—C4A—O1A	4.8 (3)	C6B—N1B—C4B—O1B	5.3 (3)
N2A—N1A—C4A—C3A	1.7 (3)	N2B—N1B—C4B—C3B	3.5 (3)
C6A—N1A—C4A—C3A	−175.51 (18)	C6B—N1B—C4B—C3B	−174.2 (2)
N3A—C3A—C4A—O1A	−4.0 (3)	N3B—C3B—C4B—O1B	−4.2 (4)
C2A—C3A—C4A—O1A	177.5 (2)	C2B—C3B—C4B—O1B	177.5 (2)
N3A—C3A—C4A—N1A	176.29 (18)	N3B—C3B—C4B—N1B	175.2 (2)
C2A—C3A—C4A—N1A	−2.2 (3)	C2B—C3B—C4B—N1B	−3.1 (3)
N3A—N4A—C5A—C2A	1.0 (2)	N3B—N4B—C5B—C2B	1.4 (2)
C24A—N4A—C5A—C2A	−176.52 (19)	C24B—N4B—C5B—C2B	−176.6 (2)
N3A—N4A—C5A—C18A	178.17 (17)	N3B—N4B—C5B—C18B	176.5 (2)
C24A—N4A—C5A—C18A	0.7 (3)	C24B—N4B—C5B—C18B	−1.5 (4)
C3A—C2A—C5A—N4A	−1.0 (2)	C3B—C2B—C5B—N4B	−1.1 (2)
C1A—C2A—C5A—N4A	176.2 (2)	C1B—C2B—C5B—N4B	176.4 (2)
C3A—C2A—C5A—C18A	−177.7 (2)	C3B—C2B—C5B—C18B	−175.7 (2)
C1A—C2A—C5A—C18A	−0.6 (4)	C1B—C2B—C5B—C18B	1.8 (5)
C4A—N1A—C6A—C7A	25.9 (3)	N2B—N1B—C6B—C7B	−146.8 (2)
N2A—N1A—C6A—C7A	−151.7 (2)	C4B—N1B—C6B—C7B	31.1 (3)
C4A—N1A—C6A—C11A	−158.21 (19)	N2B—N1B—C6B—C11B	29.1 (3)
N2A—N1A—C6A—C11A	24.2 (3)	C4B—N1B—C6B—C11B	−153.0 (2)
C11A—C6A—C7A—C8A	0.9 (4)	C11B—C6B—C7B—C8B	0.9 (4)
N1A—C6A—C7A—C8A	176.7 (2)	N1B—C6B—C7B—C8B	176.8 (2)
C6A—C7A—C8A—C9A	−0.8 (4)	C6B—C7B—C8B—C9B	−1.3 (4)
C7A—C8A—C9A—C10A	0.1 (4)	C7B—C8B—C9B—C10B	0.8 (5)
C8A—C9A—C10A—C11A	0.5 (4)	C8B—C9B—C10B—C11B	0.1 (4)
C9A—C10A—C11A—C6A	−0.4 (4)	C9B—C10B—C11B—C6B	−0.5 (4)
C7A—C6A—C11A—C10A	−0.3 (3)	C7B—C6B—C11B—C10B	0.0 (4)
N1A—C6A—C11A—C10A	−176.31 (19)	N1B—C6B—C11B—C10B	−176.0 (2)
N2A—C1A—C12A—C13A	−48.2 (3)	N2B—C1B—C12B—C13B	−41.7 (3)
C2A—C1A—C12A—C13A	133.2 (2)	C2B—C1B—C12B—C13B	141.2 (2)
N2A—C1A—C12A—C17A	130.9 (2)	N2B—C1B—C12B—C17B	134.6 (2)
C2A—C1A—C12A—C17A	−47.8 (3)	C2B—C1B—C12B—C17B	−42.6 (3)
C17A—C12A—C13A—C14A	1.0 (3)	C17B—C12B—C13B—C14B	−0.8 (3)
C1A—C12A—C13A—C14A	−179.9 (2)	C1B—C12B—C13B—C14B	175.6 (2)
C12A—C13A—C14A—C15A	0.1 (4)	C12B—C13B—C14B—C15B	0.3 (4)
C13A—C14A—C15A—C16A	−0.5 (4)	C13B—C14B—C15B—C16B	0.1 (4)
C14A—C15A—C16A—C17A	−0.1 (3)	C14B—C15B—C16B—C17B	−0.1 (4)
C13A—C12A—C17A—C16A	−1.6 (3)	C15B—C16B—C17B—C12B	−0.4 (3)
C1A—C12A—C17A—C16A	179.37 (18)	C13B—C12B—C17B—C16B	0.8 (3)
C15A—C16A—C17A—C12A	1.1 (3)	C1B—C12B—C17B—C16B	−175.42 (19)
N4A—C5A—C18A—C23A	−55.4 (3)	N4B—C5B—C18B—C19B	124.5 (2)
C2A—C5A—C18A—C23A	120.9 (3)	C2B—C5B—C18B—C19B	−61.8 (3)
N4A—C5A—C18A—C19A	128.3 (2)	N4B—C5B—C18B—C23B	−60.1 (3)
C2A—C5A—C18A—C19A	−55.4 (3)	C2B—C5B—C18B—C23B	113.6 (3)
C23A—C18A—C19A—C20A	0.1 (3)	C23B—C18B—C19B—C20B	−1.8 (3)
C5A—C18A—C19A—C20A	176.46 (18)	C5B—C18B—C19B—C20B	173.7 (2)
C18A—C19A—C20A—C21A	0.8 (3)	C18B—C19B—C20B—C21B	0.3 (4)
C19A—C20A—C21A—C22A	−0.7 (4)	C19B—C20B—C21B—C22B	1.4 (4)
C20A—C21A—C22A—C23A	−0.1 (4)	C20B—C21B—C22B—C23B	−1.7 (4)
C21A—C22A—C23A—C18A	1.0 (4)	C21B—C22B—C23B—C18B	0.2 (4)
C19A—C18A—C23A—C22A	−0.9 (3)	C19B—C18B—C23B—C22B	1.6 (4)
C5A—C18A—C23A—C22A	−177.28 (19)	C5B—C18B—C23B—C22B	−173.9 (2)
N3A—N4A—C24A—C29A	−49.6 (3)	N3B—N4B—C24B—C25B	136.0 (2)
C5A—N4A—C24A—C29A	127.8 (2)	C5B—N4B—C24B—C25B	−46.1 (4)
N3A—N4A—C24A—C25A	129.7 (2)	N3B—N4B—C24B—C29B	−41.2 (3)
C5A—N4A—C24A—C25A	−53.0 (3)	C5B—N4B—C24B—C29B	136.7 (2)
C29A—C24A—C25A—C26A	0.2 (3)	C29B—C24B—C25B—C26B	−0.5 (4)
N4A—C24A—C25A—C26A	−179.00 (19)	N4B—C24B—C25B—C26B	−177.6 (2)
C24A—C25A—C26A—C27A	−0.2 (4)	C24B—C25B—C26B—C27B	−0.4 (4)
C25A—C26A—C27A—C28A	0.4 (4)	C25B—C26B—C27B—C28B	0.7 (5)
C26A—C27A—C28A—C29A	−0.5 (4)	C26B—C27B—C28B—C29B	−0.2 (5)
C25A—C24A—C29A—C28A	−0.3 (4)	C25B—C24B—C29B—C28B	1.0 (4)
N4A—C24A—C29A—C28A	178.9 (2)	N4B—C24B—C29B—C28B	178.1 (2)
C27A—C28A—C29A—C24A	0.5 (4)	C27B—C28B—C29B—C24B	−0.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7A—H7A···O1A	0.93	2.23	2.770 (3)	116
C7B—H7B···O1B	0.93	2.32	2.814 (3)	113
C14A—H14A···O1A^i	0.93	2.44	3.255 (3)	147
C13A—H13A···O1A^ii	0.93	2.46	3.255 (3)	144
C13B—H13B···O1B^iii	0.93	2.52	3.257 (3)	136

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