Diphen-yl[2-(2-pyridylamino-meth-yl)phen-yl]phosphine oxide.

The title compound, C(24)H(21)N(2)OP, was obtained by reacting 2-amino-pyridine and 2-(diphenyl-phosphin-yl)benzaldehyde in ethanol. It crystallizes with two crystallographically independent mol-ecules in the asymmetric unit. The amino-pyridine units and the benzene ring bonded to the phosphine oxide P atom form dihedral angles of 88.58 (7) and 82.47 (9)° in the two mol-ecules. The crystal structure displays strong N-H⋯O and weak C-H⋯O hydrogen bonds along the b axis and C-H⋯π aromatic intra- and inter-molecular inter-actions.

Related literature

For synthetic applications of pyridine-containing mol­ecules and amino­phosphines, see: Borah et al. (2010 ▶); Koprowski et al. (2002 ▶); Landaeta et al. (2006 ▶); Pfeiffer et al. (2000 ▶); Ribeiro et al. (2006 ▶). For similar structures, see: Pretorius et al. (2004 ▶); Sánchez et al. (2006 ▶).

Experimental

Crystal data

C24H21N2OP

M = 384.40

Monoclinic,

a = 24.130 (3) Å

b = 8.2397 (9) Å

c = 21.992 (2) Å

β = 109.108 (2)°

V = 4131.5 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.15 mm−1

T = 298 K

0.35 × 0.14 × 0.09 mm

Data collection

Bruker SMART APEX CCD area detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.950, T max = 0.987

32921 measured reflections

7544 independent reflections

4889 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.132

S = 1.06

7544 reflections

514 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810014893/bh2276sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014893/bh2276Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C24H21N2OP	F(000) = 1616
Mr = 384.40	Dx = 1.236 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6035 reflections
a = 24.130 (3) Å	θ = 2.2–23.8°
b = 8.2397 (9) Å	µ = 0.15 mm−1
c = 21.992 (2) Å	T = 298 K
β = 109.108 (2)°	Prism, colorless
V = 4131.5 (8) Å3	0.35 × 0.14 × 0.09 mm
Z = 8

Bruker SMART APEX CCD area detector diffractometer	7544 independent reflections
Radiation source: fine-focus sealed tube	4889 reflections with I > 2σ(I)
graphite	Rint = 0.062
Detector resolution: 0.83 pixels mm-1	θmax = 25.4°, θmin = 1.8°
ω scans	h = −29→29
Absorption correction: multi-scan (SADABS; Bruker, 1999)	k = −9→9
Tmin = 0.950, Tmax = 0.987	l = −26→26
32921 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0576P)2] where P = (Fo2 + 2Fc2)/3
7544 reflections	(Δ/σ)max < 0.001
514 parameters	Δρmax = 0.31 e Å−3
2 restraints	Δρmin = −0.21 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
P1	0.36928 (3)	0.34803 (8)	0.48820 (3)	0.04454 (19)
O1	0.31222 (7)	0.26622 (19)	0.47912 (8)	0.0533 (5)
C1	0.36101 (11)	0.5619 (3)	0.47160 (12)	0.0469 (6)
C2	0.38693 (12)	0.6430 (3)	0.43397 (14)	0.0618 (8)
H2	0.4128	0.5883	0.4178	0.074*
C3	0.37526 (14)	0.8053 (3)	0.41956 (16)	0.0750 (9)
H3	0.3931	0.8592	0.3938	0.090*
C4	0.33743 (14)	0.8863 (3)	0.44333 (16)	0.0718 (9)
H4	0.3294	0.9954	0.4336	0.086*
C5	0.31182 (17)	0.8090 (4)	0.48059 (19)	0.0929 (12)
H5	0.2860	0.8645	0.4965	0.112*
C6	0.32358 (15)	0.6479 (4)	0.49535 (17)	0.0840 (10)
H6	0.3060	0.5960	0.5218	0.101*
C7	0.41605 (11)	0.3290 (3)	0.57041 (12)	0.0488 (6)
C8	0.40174 (13)	0.2123 (3)	0.60849 (14)	0.0624 (8)
H8	0.3692	0.1460	0.5909	0.075*
C9	0.43526 (16)	0.1944 (4)	0.67180 (17)	0.0819 (10)
H9	0.4251	0.1172	0.6971	0.098*
C10	0.48385 (16)	0.2899 (5)	0.69802 (16)	0.0838 (10)
H10	0.5069	0.2757	0.7408	0.101*
C11	0.49844 (14)	0.4056 (4)	0.66157 (16)	0.0817 (10)
H11	0.5314	0.4699	0.6796	0.098*
C12	0.46437 (12)	0.4276 (4)	0.59788 (14)	0.0652 (8)
H12	0.4739	0.5085	0.5735	0.078*
C13	0.40760 (11)	0.2646 (3)	0.43713 (12)	0.0444 (6)
C14	0.37875 (11)	0.2465 (3)	0.37016 (13)	0.0490 (6)
C15	0.40969 (14)	0.1765 (3)	0.33377 (14)	0.0642 (8)
H15	0.3915	0.1638	0.2897	0.077*
C16	0.46664 (15)	0.1255 (3)	0.36129 (17)	0.0713 (9)
H16	0.4863	0.0794	0.3356	0.086*
C17	0.49465 (13)	0.1416 (3)	0.42583 (15)	0.0636 (8)
H17	0.5332	0.1065	0.4442	0.076*
C18	0.46515 (11)	0.2104 (3)	0.46333 (13)	0.0527 (7)
H18	0.4842	0.2209	0.5074	0.063*
C19	0.31515 (12)	0.2952 (4)	0.33873 (13)	0.0620 (8)
H19A	0.2907	0.2172	0.3511	0.063 (8)*
H19B	0.3092	0.3999	0.3558	0.060 (8)*
N20	0.29567 (11)	0.3056 (3)	0.27000 (12)	0.0717 (7)
H20	0.2706 (10)	0.229 (3)	0.2485 (13)	0.088 (11)*
C21	0.30509 (12)	0.4386 (4)	0.23887 (14)	0.0626 (8)
N22	0.34046 (11)	0.5533 (3)	0.27378 (12)	0.0762 (7)
C23	0.34899 (16)	0.6856 (5)	0.2426 (2)	0.0977 (12)
H23	0.3731	0.7665	0.2668	0.117*
C24	0.3252 (2)	0.7099 (6)	0.1788 (2)	0.1167 (15)
H24	0.3328	0.8039	0.1595	0.140*
C25	0.28940 (18)	0.5911 (6)	0.14356 (19)	0.1085 (14)
H25	0.2721	0.6039	0.0993	0.130*
C26	0.27881 (14)	0.4540 (5)	0.17265 (16)	0.0819 (10)
H26	0.2546	0.3727	0.1488	0.098*
P2	0.16172 (3)	0.96647 (8)	0.17338 (3)	0.0487 (2)
O2	0.21808 (8)	1.0515 (2)	0.20311 (8)	0.0655 (5)
C27	0.14545 (12)	0.8307 (3)	0.22969 (12)	0.0517 (7)
C28	0.09067 (13)	0.8167 (3)	0.23625 (13)	0.0598 (7)
H28	0.0595	0.8773	0.2099	0.072*
C29	0.08174 (15)	0.7131 (4)	0.28181 (14)	0.0728 (9)
H29	0.0447	0.7053	0.2860	0.087*
C30	0.1266 (2)	0.6228 (4)	0.32031 (16)	0.0897 (11)
H30	0.1203	0.5525	0.3505	0.108*
C31	0.1809 (2)	0.6356 (5)	0.31456 (18)	0.1041 (13)
H31	0.2117	0.5737	0.3409	0.125*
C32	0.19065 (15)	0.7397 (4)	0.27002 (16)	0.0855 (10)
H32	0.2281	0.7487	0.2671	0.103*
C33	0.10068 (11)	1.1037 (3)	0.14587 (12)	0.0479 (6)
C34	0.10371 (13)	1.2529 (3)	0.17540 (14)	0.0632 (8)
H34	0.1375	1.2822	0.2085	0.076*
C35	0.05676 (16)	1.3588 (4)	0.15592 (18)	0.0799 (10)
H35	0.0591	1.4591	0.1760	0.096*
C36	0.00708 (16)	1.3166 (4)	0.10740 (18)	0.0848 (10)
H36	−0.0244	1.3883	0.0947	0.102*
C37	0.00316 (14)	1.1700 (4)	0.07738 (15)	0.0808 (10)
H37	−0.0308	1.1418	0.0442	0.097*
C38	0.04992 (13)	1.0642 (4)	0.09665 (14)	0.0659 (8)
H38	0.0473	0.9644	0.0761	0.079*
C39	0.15882 (10)	0.8468 (3)	0.10359 (12)	0.0458 (6)
C40	0.17556 (10)	0.9141 (3)	0.05390 (12)	0.0472 (6)
C41	0.17159 (12)	0.8183 (4)	0.00108 (13)	0.0600 (7)
H41	0.1829	0.8612	−0.0321	0.072*
C42	0.15121 (13)	0.6606 (4)	−0.00373 (14)	0.0674 (8)
H42	0.1490	0.5988	−0.0398	0.081*
C43	0.13435 (12)	0.5957 (3)	0.04431 (14)	0.0658 (8)
H43	0.1204	0.4898	0.0412	0.079*
C44	0.13816 (12)	0.6885 (3)	0.09777 (13)	0.0574 (7)
H44	0.1266	0.6440	0.1306	0.069*
C45	0.19811 (12)	1.0878 (3)	0.05873 (13)	0.0596 (7)
H45A	0.1711	1.1572	0.0710	0.071*
H45B	0.2356	1.0929	0.0930	0.071*
N46	0.20546 (10)	1.1520 (3)	0.00087 (11)	0.0655 (7)
H46	0.2420 (6)	1.166 (3)	−0.0005 (14)	0.079*
C47	0.16033 (12)	1.2132 (3)	−0.04842 (13)	0.0517 (7)
N48	0.10652 (10)	1.1985 (3)	−0.04558 (12)	0.0667 (7)
C49	0.06305 (14)	1.2601 (4)	−0.0959 (2)	0.0875 (11)
H49	0.0249	1.2524	−0.0950	0.105*
C50	0.07112 (18)	1.3323 (4)	−0.1475 (2)	0.0947 (12)
H50	0.0394	1.3712	−0.1811	0.114*
C51	0.12719 (18)	1.3467 (4)	−0.14908 (15)	0.0808 (10)
H51	0.1341	1.3965	−0.1839	0.097*
C52	0.17227 (13)	1.2881 (3)	−0.09982 (13)	0.0600 (7)
H52	0.2106	1.2974	−0.1000	0.072*

	U11	U22	U33	U12	U13	U23
P1	0.0453 (4)	0.0368 (4)	0.0537 (4)	−0.0034 (3)	0.0191 (3)	−0.0036 (3)
O1	0.0440 (10)	0.0464 (10)	0.0716 (12)	−0.0070 (8)	0.0217 (9)	−0.0086 (9)
C1	0.0500 (15)	0.0384 (14)	0.0544 (16)	−0.0029 (12)	0.0197 (13)	−0.0058 (12)
C2	0.0686 (19)	0.0444 (16)	0.083 (2)	−0.0057 (14)	0.0391 (16)	−0.0039 (15)
C3	0.099 (3)	0.0467 (18)	0.091 (2)	−0.0119 (17)	0.047 (2)	0.0037 (17)
C4	0.083 (2)	0.0346 (16)	0.094 (2)	−0.0013 (16)	0.0242 (19)	−0.0019 (16)
C5	0.119 (3)	0.0454 (19)	0.144 (3)	0.0115 (19)	0.083 (3)	0.000 (2)
C6	0.114 (3)	0.0493 (19)	0.120 (3)	0.0035 (18)	0.080 (2)	0.0017 (19)
C7	0.0506 (15)	0.0481 (15)	0.0527 (16)	−0.0001 (13)	0.0236 (13)	−0.0009 (13)
C8	0.0638 (18)	0.0644 (19)	0.064 (2)	−0.0008 (15)	0.0276 (16)	0.0057 (16)
C9	0.096 (3)	0.091 (3)	0.066 (2)	0.010 (2)	0.037 (2)	0.0181 (19)
C10	0.087 (3)	0.113 (3)	0.0507 (19)	0.017 (2)	0.0218 (19)	0.002 (2)
C11	0.074 (2)	0.099 (3)	0.062 (2)	−0.0126 (19)	0.0089 (18)	−0.016 (2)
C12	0.0689 (19)	0.0671 (19)	0.0585 (19)	−0.0118 (16)	0.0195 (16)	−0.0020 (15)
C13	0.0473 (15)	0.0331 (13)	0.0570 (17)	−0.0022 (11)	0.0228 (13)	−0.0001 (12)
C14	0.0566 (17)	0.0376 (14)	0.0546 (17)	−0.0023 (12)	0.0208 (14)	0.0009 (12)
C15	0.088 (2)	0.0537 (17)	0.0581 (18)	0.0001 (17)	0.0334 (17)	−0.0043 (15)
C16	0.090 (2)	0.0592 (19)	0.083 (2)	0.0169 (17)	0.053 (2)	0.0038 (17)
C17	0.0638 (19)	0.0553 (18)	0.081 (2)	0.0141 (15)	0.0363 (17)	0.0095 (17)
C18	0.0564 (17)	0.0451 (15)	0.0610 (17)	0.0031 (13)	0.0254 (14)	0.0045 (13)
C19	0.0643 (19)	0.0597 (19)	0.0576 (19)	−0.0071 (15)	0.0140 (15)	−0.0010 (15)
N20	0.0771 (18)	0.0701 (18)	0.0536 (16)	−0.0213 (15)	0.0020 (13)	−0.0056 (14)
C21	0.0540 (17)	0.071 (2)	0.0556 (19)	0.0042 (16)	0.0077 (15)	−0.0050 (17)
N22	0.0786 (18)	0.0664 (17)	0.0721 (17)	−0.0081 (14)	0.0091 (14)	0.0047 (15)
C23	0.092 (3)	0.077 (3)	0.116 (3)	−0.006 (2)	0.023 (2)	0.018 (2)
C24	0.099 (3)	0.127 (4)	0.117 (4)	0.009 (3)	0.025 (3)	0.057 (3)
C25	0.089 (3)	0.153 (4)	0.072 (3)	0.027 (3)	0.010 (2)	0.038 (3)
C26	0.067 (2)	0.106 (3)	0.059 (2)	0.012 (2)	0.0026 (17)	0.002 (2)
P2	0.0565 (4)	0.0461 (4)	0.0431 (4)	−0.0054 (3)	0.0156 (3)	−0.0045 (3)
O2	0.0632 (12)	0.0670 (12)	0.0586 (12)	−0.0165 (10)	0.0093 (9)	−0.0092 (10)
C27	0.0675 (18)	0.0471 (15)	0.0407 (15)	0.0036 (14)	0.0177 (14)	−0.0023 (12)
C28	0.073 (2)	0.0579 (18)	0.0476 (16)	−0.0048 (15)	0.0185 (14)	−0.0008 (14)
C29	0.090 (2)	0.079 (2)	0.0545 (19)	−0.0183 (19)	0.0302 (18)	−0.0005 (17)
C30	0.133 (3)	0.080 (2)	0.057 (2)	−0.007 (2)	0.032 (2)	0.0119 (18)
C31	0.123 (3)	0.102 (3)	0.085 (3)	0.034 (3)	0.031 (2)	0.044 (2)
C32	0.087 (2)	0.095 (3)	0.079 (2)	0.020 (2)	0.032 (2)	0.026 (2)
C33	0.0635 (17)	0.0411 (14)	0.0449 (15)	−0.0039 (13)	0.0254 (14)	−0.0032 (12)
C34	0.074 (2)	0.0526 (18)	0.0677 (19)	−0.0069 (16)	0.0290 (16)	−0.0058 (15)
C35	0.095 (3)	0.0499 (19)	0.106 (3)	0.0034 (19)	0.048 (2)	−0.0115 (19)
C36	0.086 (3)	0.077 (2)	0.095 (3)	0.027 (2)	0.035 (2)	0.007 (2)
C37	0.071 (2)	0.088 (2)	0.074 (2)	0.0184 (19)	0.0108 (17)	−0.011 (2)
C38	0.071 (2)	0.0598 (18)	0.0625 (19)	0.0109 (16)	0.0159 (16)	−0.0121 (15)
C39	0.0469 (15)	0.0439 (15)	0.0452 (15)	0.0003 (12)	0.0134 (12)	−0.0017 (12)
C40	0.0451 (14)	0.0540 (16)	0.0409 (14)	0.0046 (12)	0.0118 (12)	−0.0015 (13)
C41	0.0615 (18)	0.076 (2)	0.0440 (16)	0.0086 (16)	0.0189 (14)	0.0014 (15)
C42	0.078 (2)	0.070 (2)	0.0513 (18)	0.0105 (17)	0.0161 (16)	−0.0166 (16)
C43	0.077 (2)	0.0509 (17)	0.067 (2)	0.0012 (15)	0.0200 (16)	−0.0128 (16)
C44	0.0658 (18)	0.0517 (17)	0.0573 (18)	−0.0040 (14)	0.0236 (14)	−0.0043 (14)
C45	0.0651 (18)	0.0654 (18)	0.0494 (16)	−0.0061 (15)	0.0204 (14)	0.0058 (14)
N46	0.0513 (14)	0.0871 (18)	0.0620 (15)	0.0015 (14)	0.0239 (13)	0.0205 (14)
C47	0.0514 (17)	0.0470 (15)	0.0569 (17)	0.0022 (13)	0.0180 (14)	−0.0001 (13)
N48	0.0519 (15)	0.0629 (16)	0.0865 (19)	0.0028 (12)	0.0244 (14)	0.0023 (14)
C49	0.051 (2)	0.067 (2)	0.132 (3)	0.0039 (17)	0.012 (2)	−0.006 (2)
C50	0.087 (3)	0.075 (2)	0.094 (3)	0.020 (2)	−0.010 (2)	0.003 (2)
C51	0.109 (3)	0.069 (2)	0.059 (2)	0.019 (2)	0.020 (2)	0.0099 (17)
C52	0.0700 (19)	0.0587 (18)	0.0553 (18)	0.0100 (15)	0.0260 (16)	0.0065 (15)

P1—O1	1.4866 (17)	P2—O2	1.4782 (18)
P1—C1	1.798 (2)	P2—C33	1.797 (3)
P1—C7	1.798 (3)	P2—C27	1.805 (3)
P1—C13	1.808 (2)	P2—C39	1.806 (3)
C1—C2	1.364 (3)	C27—C32	1.380 (4)
C1—C6	1.378 (4)	C27—C28	1.381 (4)
C2—C3	1.382 (4)	C28—C29	1.386 (4)
C2—H2	0.9300	C28—H28	0.9300
C3—C4	1.365 (4)	C29—C30	1.358 (4)
C3—H3	0.9300	C29—H29	0.9300
C4—C5	1.338 (4)	C30—C31	1.361 (5)
C4—H4	0.9300	C30—H30	0.9300
C5—C6	1.374 (4)	C31—C32	1.378 (5)
C5—H5	0.9300	C31—H31	0.9300
C6—H6	0.9300	C32—H32	0.9300
C7—C12	1.387 (4)	C33—C34	1.381 (3)
C7—C8	1.391 (3)	C33—C38	1.382 (4)
C8—C9	1.370 (4)	C34—C35	1.382 (4)
C8—H8	0.9300	C34—H34	0.9300
C9—C10	1.372 (5)	C35—C36	1.363 (4)
C9—H9	0.9300	C35—H35	0.9300
C10—C11	1.364 (4)	C36—C37	1.365 (4)
C10—H10	0.9300	C36—H36	0.9300
C11—C12	1.385 (4)	C37—C38	1.379 (4)
C11—H11	0.9300	C37—H37	0.9300
C12—H12	0.9300	C38—H38	0.9300
C13—C18	1.391 (3)	C39—C44	1.387 (3)
C13—C14	1.416 (3)	C39—C40	1.398 (3)
C14—C15	1.386 (3)	C40—C41	1.382 (3)
C14—C19	1.516 (4)	C40—C45	1.522 (3)
C15—C16	1.374 (4)	C41—C42	1.381 (4)
C15—H15	0.9300	C41—H41	0.9300
C16—C17	1.364 (4)	C42—C43	1.360 (4)
C16—H16	0.9300	C42—H42	0.9300
C17—C18	1.376 (3)	C43—C44	1.380 (4)
C17—H17	0.9300	C43—H43	0.9300
C18—H18	0.9300	C44—H44	0.9300
C19—N20	1.431 (3)	C45—N46	1.442 (3)
C19—H19A	0.9700	C45—H45A	0.9700
C19—H19B	0.9700	C45—H45B	0.9700
N20—C21	1.350 (4)	N46—C47	1.357 (3)
N20—H20	0.895 (10)	N46—H46	0.899 (10)
C21—N22	1.335 (3)	C47—N48	1.326 (3)
C21—C26	1.391 (4)	C47—C52	1.398 (4)
N22—C23	1.339 (4)	N48—C49	1.350 (4)
C23—C24	1.346 (5)	C49—C50	1.350 (5)
C23—H23	0.9300	C49—H49	0.9300
C24—C25	1.366 (6)	C50—C51	1.370 (5)
C24—H24	0.9300	C50—H50	0.9300
C25—C26	1.363 (5)	C51—C52	1.348 (4)
C25—H25	0.9300	C51—H51	0.9300
C26—H26	0.9300	C52—H52	0.9300
O1—P1—C1	112.39 (11)	O2—P2—C33	112.62 (12)
O1—P1—C7	110.16 (11)	O2—P2—C27	111.44 (12)
C1—P1—C7	106.34 (12)	C33—P2—C27	106.42 (12)
O1—P1—C13	112.55 (10)	O2—P2—C39	114.12 (11)
C1—P1—C13	106.98 (11)	C33—P2—C39	104.94 (11)
C7—P1—C13	108.14 (12)	C27—P2—C39	106.73 (12)
C2—C1—C6	117.7 (2)	C32—C27—C28	118.0 (3)
C2—C1—P1	124.1 (2)	C32—C27—P2	118.3 (2)
C6—C1—P1	118.0 (2)	C28—C27—P2	123.6 (2)
C1—C2—C3	120.9 (3)	C27—C28—C29	120.5 (3)
C1—C2—H2	119.5	C27—C28—H28	119.7
C3—C2—H2	119.5	C29—C28—H28	119.7
C4—C3—C2	119.8 (3)	C30—C29—C28	120.5 (3)
C4—C3—H3	120.1	C30—C29—H29	119.8
C2—C3—H3	120.1	C28—C29—H29	119.8
C5—C4—C3	120.2 (3)	C29—C30—C31	119.7 (3)
C5—C4—H4	119.9	C29—C30—H30	120.2
C3—C4—H4	119.9	C31—C30—H30	120.2
C4—C5—C6	120.2 (3)	C30—C31—C32	120.5 (3)
C4—C5—H5	119.9	C30—C31—H31	119.8
C6—C5—H5	119.9	C32—C31—H31	119.8
C5—C6—C1	121.2 (3)	C31—C32—C27	120.8 (3)
C5—C6—H6	119.4	C31—C32—H32	119.6
C1—C6—H6	119.4	C27—C32—H32	119.6
C12—C7—C8	118.8 (3)	C34—C33—C38	118.4 (3)
C12—C7—P1	123.3 (2)	C34—C33—P2	119.4 (2)
C8—C7—P1	117.9 (2)	C38—C33—P2	122.3 (2)
C9—C8—C7	120.4 (3)	C33—C34—C35	120.3 (3)
C9—C8—H8	119.8	C33—C34—H34	119.9
C7—C8—H8	119.8	C35—C34—H34	119.9
C8—C9—C10	120.3 (3)	C36—C35—C34	120.2 (3)
C8—C9—H9	119.9	C36—C35—H35	119.9
C10—C9—H9	119.9	C34—C35—H35	119.9
C11—C10—C9	120.2 (3)	C35—C36—C37	120.5 (3)
C11—C10—H10	119.9	C35—C36—H36	119.7
C9—C10—H10	119.9	C37—C36—H36	119.7
C10—C11—C12	120.3 (3)	C36—C37—C38	119.4 (3)
C10—C11—H11	119.9	C36—C37—H37	120.3
C12—C11—H11	119.9	C38—C37—H37	120.3
C11—C12—C7	120.0 (3)	C37—C38—C33	121.2 (3)
C11—C12—H12	120.0	C37—C38—H38	119.4
C7—C12—H12	120.0	C33—C38—H38	119.4
C18—C13—C14	118.8 (2)	C44—C39—C40	119.2 (2)
C18—C13—P1	120.6 (2)	C44—C39—P2	120.30 (19)
C14—C13—P1	120.59 (19)	C40—C39—P2	120.45 (19)
C15—C14—C13	118.0 (2)	C41—C40—C39	118.2 (2)
C15—C14—C19	120.2 (2)	C41—C40—C45	121.4 (2)
C13—C14—C19	121.7 (2)	C39—C40—C45	120.4 (2)
C16—C15—C14	121.5 (3)	C42—C41—C40	121.8 (3)
C16—C15—H15	119.2	C42—C41—H41	119.1
C14—C15—H15	119.2	C40—C41—H41	119.1
C17—C16—C15	120.8 (3)	C43—C42—C41	120.0 (3)
C17—C16—H16	119.6	C43—C42—H42	120.0
C15—C16—H16	119.6	C41—C42—H42	120.0
C16—C17—C18	119.1 (3)	C42—C43—C44	119.4 (3)
C16—C17—H17	120.4	C42—C43—H43	120.3
C18—C17—H17	120.4	C44—C43—H43	120.3
C17—C18—C13	121.7 (3)	C43—C44—C39	121.4 (3)
C17—C18—H18	119.1	C43—C44—H44	119.3
C13—C18—H18	119.1	C39—C44—H44	119.3
N20—C19—C14	115.5 (2)	N46—C45—C40	115.4 (2)
N20—C19—H19A	108.4	N46—C45—H45A	108.4
C14—C19—H19A	108.4	C40—C45—H45A	108.4
N20—C19—H19B	108.4	N46—C45—H45B	108.4
C14—C19—H19B	108.4	C40—C45—H45B	108.4
H19A—C19—H19B	107.5	H45A—C45—H45B	107.5
C21—N20—C19	122.2 (3)	C47—N46—C45	122.9 (2)
C21—N20—H20	120 (2)	C47—N46—H46	117.7 (19)
C19—N20—H20	117 (2)	C45—N46—H46	118.8 (19)
N22—C21—N20	117.7 (3)	N48—C47—N46	118.1 (3)
N22—C21—C26	121.6 (3)	N48—C47—C52	122.9 (3)
N20—C21—C26	120.7 (3)	N46—C47—C52	119.1 (2)
C21—N22—C23	117.3 (3)	C47—N48—C49	115.9 (3)
N22—C23—C24	124.8 (4)	C50—C49—N48	124.6 (3)
N22—C23—H23	117.6	C50—C49—H49	117.7
C24—C23—H23	117.6	N48—C49—H49	117.7
C23—C24—C25	117.4 (4)	C49—C50—C51	118.4 (3)
C23—C24—H24	121.3	C49—C50—H50	120.8
C25—C24—H24	121.3	C51—C50—H50	120.8
C26—C25—C24	120.6 (4)	C52—C51—C50	119.5 (3)
C26—C25—H25	119.7	C52—C51—H51	120.3
C24—C25—H25	119.7	C50—C51—H51	120.3
C25—C26—C21	118.4 (4)	C51—C52—C47	118.8 (3)
C25—C26—H26	120.8	C51—C52—H52	120.6
C21—C26—H26	120.8	C47—C52—H52	120.6
O1—P1—C1—C2	−132.3 (2)	O2—P2—C27—C32	−40.9 (3)
C7—P1—C1—C2	107.1 (2)	C33—P2—C27—C32	−164.1 (2)
C13—P1—C1—C2	−8.3 (3)	C39—P2—C27—C32	84.3 (2)
O1—P1—C1—C6	43.9 (3)	O2—P2—C27—C28	136.7 (2)
C7—P1—C1—C6	−76.7 (3)	C33—P2—C27—C28	13.6 (3)
C13—P1—C1—C6	167.9 (2)	C39—P2—C27—C28	−98.1 (2)
C6—C1—C2—C3	−0.9 (4)	C32—C27—C28—C29	−0.5 (4)
P1—C1—C2—C3	175.3 (2)	P2—C27—C28—C29	−178.2 (2)
C1—C2—C3—C4	0.2 (5)	C27—C28—C29—C30	−0.5 (4)
C2—C3—C4—C5	0.2 (5)	C28—C29—C30—C31	0.7 (5)
C3—C4—C5—C6	0.2 (6)	C29—C30—C31—C32	0.1 (6)
C4—C5—C6—C1	−1.0 (6)	C30—C31—C32—C27	−1.1 (6)
C2—C1—C6—C5	1.3 (5)	C28—C27—C32—C31	1.3 (5)
P1—C1—C6—C5	−175.2 (3)	P2—C27—C32—C31	179.1 (3)
O1—P1—C7—C12	−161.6 (2)	O2—P2—C33—C34	−26.9 (2)
C1—P1—C7—C12	−39.6 (3)	C27—P2—C33—C34	95.5 (2)
C13—P1—C7—C12	75.0 (2)	C39—P2—C33—C34	−151.6 (2)
O1—P1—C7—C8	16.5 (2)	O2—P2—C33—C38	154.4 (2)
C1—P1—C7—C8	138.5 (2)	C27—P2—C33—C38	−83.2 (2)
C13—P1—C7—C8	−106.9 (2)	C39—P2—C33—C38	29.7 (2)
C12—C7—C8—C9	−0.6 (4)	C38—C33—C34—C35	0.2 (4)
P1—C7—C8—C9	−178.8 (2)	P2—C33—C34—C35	−178.6 (2)
C7—C8—C9—C10	−1.0 (5)	C33—C34—C35—C36	0.1 (5)
C8—C9—C10—C11	1.3 (5)	C34—C35—C36—C37	−0.3 (5)
C9—C10—C11—C12	0.0 (5)	C35—C36—C37—C38	0.2 (5)
C10—C11—C12—C7	−1.7 (5)	C36—C37—C38—C33	0.1 (5)
C8—C7—C12—C11	2.0 (4)	C34—C33—C38—C37	−0.3 (4)
P1—C7—C12—C11	−179.9 (2)	P2—C33—C38—C37	178.5 (2)
O1—P1—C13—C18	−126.2 (2)	O2—P2—C39—C44	132.3 (2)
C1—P1—C13—C18	109.8 (2)	C33—P2—C39—C44	−103.9 (2)
C7—P1—C13—C18	−4.3 (2)	C27—P2—C39—C44	8.8 (2)
O1—P1—C13—C14	50.9 (2)	O2—P2—C39—C40	−49.7 (2)
C1—P1—C13—C14	−73.0 (2)	C33—P2—C39—C40	74.1 (2)
C7—P1—C13—C14	172.84 (19)	C27—P2—C39—C40	−173.3 (2)
C18—C13—C14—C15	−0.5 (3)	C44—C39—C40—C41	−1.0 (4)
P1—C13—C14—C15	−177.76 (18)	P2—C39—C40—C41	−178.93 (19)
C18—C13—C14—C19	177.0 (2)	C44—C39—C40—C45	179.7 (2)
P1—C13—C14—C19	−0.2 (3)	P2—C39—C40—C45	1.7 (3)
C13—C14—C15—C16	0.1 (4)	C39—C40—C41—C42	0.6 (4)
C19—C14—C15—C16	−177.5 (3)	C45—C40—C41—C42	180.0 (3)
C14—C15—C16—C17	0.3 (4)	C40—C41—C42—C43	0.0 (4)
C15—C16—C17—C18	−0.2 (4)	C41—C42—C43—C44	−0.4 (4)
C16—C17—C18—C13	−0.3 (4)	C42—C43—C44—C39	0.0 (4)
C14—C13—C18—C17	0.6 (4)	C40—C39—C44—C43	0.7 (4)
P1—C13—C18—C17	177.9 (2)	P2—C39—C44—C43	178.6 (2)
C15—C14—C19—N20	−16.3 (4)	C41—C40—C45—N46	9.8 (4)
C13—C14—C19—N20	166.2 (2)	C39—C40—C45—N46	−170.9 (2)
C14—C19—N20—C21	−82.7 (4)	C40—C45—N46—C47	81.3 (3)
C19—N20—C21—N22	9.1 (4)	C45—N46—C47—N48	−6.7 (4)
C19—N20—C21—C26	−171.1 (3)	C45—N46—C47—C52	173.5 (2)
N20—C21—N22—C23	−179.2 (3)	N46—C47—N48—C49	−179.5 (3)
C26—C21—N22—C23	1.0 (4)	C52—C47—N48—C49	0.3 (4)
C21—N22—C23—C24	−0.9 (5)	C47—N48—C49—C50	0.6 (5)
N22—C23—C24—C25	0.5 (7)	N48—C49—C50—C51	−0.9 (6)
C23—C24—C25—C26	−0.1 (6)	C49—C50—C51—C52	0.4 (5)
C24—C25—C26—C21	0.2 (6)	C50—C51—C52—C47	0.3 (5)
N22—C21—C26—C25	−0.7 (5)	N48—C47—C52—C51	−0.7 (4)
N20—C21—C26—C25	179.5 (3)	N46—C47—C52—C51	179.1 (3)

Cg1, Cg2 and Cg3 are the centroids of the C13–C18, C39–C44 and N48,C47,C49–C52 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N20—H20···O2i	0.90 (1)	1.98 (1)	2.872 (3)	177 (3)
N46—H46···O1ii	0.90 (1)	1.97 (1)	2.850 (3)	166 (3)
C4—H4···O1iii	0.93	2.53	3.329	144
C52—H52···O1ii	0.93	2.55	3.282	135
C3—H3···Cg1iii	0.93	2.95	3.627 (3)	131
C25—H25···Cg2	0.93	2.95	3.495 (5)	119
C30—H30···Cg3iv	0.93	2.93	3.772 (4)	152
C42—H42···Cg3i	0.93	2.96	3.746 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C13–C18, C39–C44 and N48,C47,C49–C52 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N20—H20⋯O2i	0.90 (1)	1.98 (1)	2.872 (3)	177 (3)
N46—H46⋯O1ii	0.90 (1)	1.97 (1)	2.850 (3)	166 (3)
C4—H4⋯O1iii	0.93	2.53	3.329	144
C52—H52⋯O1ii	0.93	2.55	3.282	135
C3—H3⋯Cg1iii	0.93	2.95	3.627 (3)	131
C25—H25⋯Cg2	0.93	2.95	3.495 (5)	119
C30—H30⋯Cg3iv	0.93	2.93	3.772 (4)	152
C42—H42⋯Cg3i	0.93	2.96	3.746 (3)	154

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .