N,N-Bis-(2,6-di-methyl-phen-yl)-N-hydroxyformamidine N,N'-bis-(2,6-dimethyl-phen-yl)-N-oxidoformamidinium dichloro-methane solvate.

The title compound, 2C(17)H(20)N(2)O·CH(2)Cl(2), was obtained by N-oxidation of the parent formamidine with m-chloro-peroxy-benzoic acid (m-CPBA). This is the first use of the above-mentioned synthetic route for the preparation of hydroxy-amidines. The title compound crystallizes as a cyclic dimer resulting from the presence of O-H⋯O and N-H⋯N hydrogen bonds.

Related literature

For synthesis, properties and applications of hydroxy­amidines and the parent amidines, see: Krahulic et al. (2005 ▶); Hirano et al. (2009 ▶); Coles (2006 ▶); Cotton et al. (2003 ▶); Chartrand & Hanan (2008 ▶); Briggs et al. (1976 ▶); Krajete et al. (2004 ▶); Kharsan & Mishra (1980 ▶); Satyanarayana & Mishra (1976 ▶).

Experimental

Crystal data

2C17H20N2O·CH2Cl2

M = 621.63

Orthorhombic,

a = 16.360 (5) Å

b = 18.137 (6) Å

c = 11.421 (4) Å

V = 3388.6 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 200 K

0.18 × 0.09 × 0.05 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.806, T max = 0.989

59541 measured reflections

6211 independent reflections

4233 reflections with I > 2σ(I)

R int = 0.082

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.136

S = 1.03

6211 reflections

405 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.34 e Å−3

Absolute structure: Flack (1983 ▶), 2931 Friedel Pairs

Flack parameter: 0.06 (9)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: UdMX (Maris, 2004 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809036708/ez2181sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036708/ez2181Isup2.hkl

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

2C17H20N2O·CH2Cl2	F(000) = 1320
Mr = 621.63	Dx = 1.218 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 6035 reflections
a = 16.360 (5) Å	θ = 2.3–19.7°
b = 18.137 (6) Å	µ = 0.23 mm−1
c = 11.421 (4) Å	T = 200 K
V = 3388.6 (18) Å3	Needle, colorless
Z = 4	0.18 × 0.09 × 0.05 mm

Bruker APEXII diffractometer	6211 independent reflections
Radiation source: X-ray sealed tube	4233 reflections with I > 2σ(I)
Graphite	Rint = 0.082
Detector resolution: 8.3 pixels mm-1	θmax = 25.4°, θmin = 1.7°
ω scans	h = −19→19
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −21→21
Tmin = 0.806, Tmax = 0.989	l = −13→13
59541 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.136	w = 1/[σ2(Fo2) + (0.067P)2 + 0.3477P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
6211 reflections	Δρmax = 0.24 e Å−3
405 parameters	Δρmin = −0.34 e Å−3
1 restraint	Absolute structure: Flack (1983), 2931 Friedel Pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.06 (9)

Experimental. X-ray crystallographic data for 1 were collected from a single-crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker smart diffractometer equiped with an APEX II CCD Detector, a graphite monochromator. The crystal-to-detector distance was 5.0 cm, and the data collection was carried out in 512 x 512 pixel mode. The initial unit-cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 10.0 degree scan in 33 frames over four different parts of the reciprocal space (132 frames total).

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.

	x	y	z	Uiso*/Ueq
Cl1	0.79719 (8)	0.13777 (9)	0.47507 (13)	0.1095 (5)
Cl2	0.62760 (8)	0.15036 (11)	0.53563 (14)	0.1307 (7)
O1	0.66822 (11)	0.09653 (12)	0.9961 (2)	0.0514 (6)
O2	0.62942 (12)	0.16297 (13)	0.1805 (2)	0.0495 (6)
N1	0.74883 (14)	0.10368 (14)	0.9705 (2)	0.0421 (6)
N2	0.73452 (18)	0.22848 (14)	0.9479 (2)	0.0426 (6)
N3	0.54544 (14)	0.17397 (14)	0.1661 (2)	0.0430 (6)
N4	0.56736 (14)	0.25572 (13)	0.0124 (2)	0.0406 (6)
C1	0.77938 (18)	0.16788 (18)	0.9475 (3)	0.0428 (7)
H1A	0.8360	0.1716	0.9298	0.051*
C2	0.52018 (18)	0.22085 (17)	0.0842 (3)	0.0400 (7)
H2A	0.4630	0.2293	0.0780	0.048*
C11	0.79546 (18)	0.03579 (17)	0.9723 (3)	0.0460 (8)
C12	0.8263 (2)	0.01206 (19)	1.0789 (3)	0.0545 (9)
C13	0.8652 (2)	−0.0568 (2)	1.0819 (4)	0.0694 (11)
H13	0.8860	−0.0753	1.1538	0.083*
C14	0.8734 (2)	−0.0968 (2)	0.9828 (5)	0.0807 (13)
H14	0.9015	−0.1426	0.9862	0.097*
C15	0.8425 (2)	−0.0736 (2)	0.8775 (5)	0.0732 (12)
H15	0.8488	−0.1038	0.8101	0.088*
C16	0.80118 (19)	−0.0047 (2)	0.8679 (3)	0.0569 (9)
C17	0.8183 (3)	0.0565 (2)	1.1877 (4)	0.0713 (11)
H17A	0.8334	0.0263	1.2554	0.107*
H17B	0.7616	0.0732	1.1962	0.107*
H17C	0.8545	0.0995	1.1832	0.107*
C18	0.7663 (3)	0.0240 (3)	0.7564 (4)	0.0731 (12)
H18A	0.7066	0.0258	0.7625	0.110*
H18B	0.7819	−0.0087	0.6918	0.110*
H18C	0.7875	0.0737	0.7416	0.110*
C21	0.76902 (17)	0.30074 (17)	0.9323 (3)	0.0425 (7)
C22	0.7740 (2)	0.33000 (19)	0.8192 (3)	0.0492 (8)
C23	0.8056 (2)	0.4009 (2)	0.8066 (4)	0.0630 (10)
H23	0.8094	0.4220	0.7307	0.076*
C24	0.8311 (2)	0.4405 (2)	0.9018 (4)	0.0659 (11)
H24	0.8525	0.4887	0.8913	0.079*
C25	0.8260 (2)	0.4108 (2)	1.0132 (4)	0.0628 (10)
H25	0.8445	0.4387	1.0784	0.075*
C26	0.79364 (18)	0.33988 (19)	1.0309 (3)	0.0490 (8)
C27	0.7843 (2)	0.3081 (2)	1.1515 (3)	0.0620 (10)
H27A	0.7271	0.2944	1.1644	0.093*
H27B	0.8008	0.3450	1.2097	0.093*
H27C	0.8190	0.2643	1.1591	0.093*
C28	0.7459 (3)	0.2863 (2)	0.7147 (3)	0.0675 (11)
H28A	0.6874	0.2757	0.7220	0.101*
H28B	0.7764	0.2398	0.7109	0.101*
H28C	0.7557	0.3147	0.6431	0.101*
C31	0.49473 (18)	0.14566 (18)	0.2579 (3)	0.0412 (7)
C32	0.48195 (19)	0.06980 (19)	0.2632 (3)	0.0474 (8)
C33	0.4336 (2)	0.0424 (2)	0.3538 (3)	0.0583 (9)
H33	0.4246	−0.0092	0.3602	0.070*
C34	0.3988 (2)	0.0896 (2)	0.4340 (3)	0.0636 (11)
H34	0.3651	0.0703	0.4944	0.076*
C35	0.4122 (2)	0.1640 (2)	0.4277 (3)	0.0577 (9)
H35	0.3874	0.1956	0.4837	0.069*
C36	0.46178 (18)	0.19438 (19)	0.3404 (3)	0.0471 (8)
C37	0.5179 (2)	0.0186 (2)	0.1726 (3)	0.0598 (9)
H37A	0.5031	0.0359	0.0941	0.090*
H37B	0.4965	−0.0313	0.1845	0.090*
H37C	0.5776	0.0180	0.1804	0.090*
C38	0.4799 (2)	0.2753 (2)	0.3355 (4)	0.0643 (10)
H38A	0.5372	0.2827	0.3136	0.096*
H38B	0.4698	0.2974	0.4125	0.096*
H38C	0.4444	0.2987	0.2772	0.096*
C41	0.52944 (17)	0.29863 (17)	−0.0770 (3)	0.0413 (7)
C42	0.52622 (19)	0.37486 (18)	−0.0640 (3)	0.0512 (8)
C43	0.4916 (2)	0.4163 (2)	−0.1540 (4)	0.0669 (11)
H43	0.4888	0.4685	−0.1467	0.080*
C44	0.4614 (2)	0.3830 (3)	−0.2536 (4)	0.0706 (12)
H44	0.4372	0.4118	−0.3138	0.085*
C45	0.4664 (2)	0.3084 (3)	−0.2652 (3)	0.0622 (11)
H45	0.4461	0.2858	−0.3344	0.075*
C46	0.50072 (19)	0.26419 (19)	−0.1777 (3)	0.0469 (8)
C47	0.5609 (3)	0.4121 (2)	0.0424 (4)	0.0740 (11)
H47A	0.5311	0.3956	0.1121	0.111*
H47B	0.5554	0.4656	0.0342	0.111*
H47C	0.6188	0.3992	0.0504	0.111*
C48	0.5076 (3)	0.1818 (2)	−0.1925 (4)	0.0653 (10)
H48A	0.5641	0.1664	−0.1780	0.098*
H48B	0.4918	0.1682	−0.2725	0.098*
H48C	0.4712	0.1572	−0.1366	0.098*
C51	0.7056 (4)	0.1803 (4)	0.4413 (4)	0.117 (2)
H51A	0.6905	0.1688	0.3593	0.140*
H51B	0.7119	0.2344	0.4482	0.140*
H1	0.688 (2)	0.229 (2)	0.962 (4)	0.064 (12)*
H2	0.653 (2)	0.138 (2)	0.105 (4)	0.070 (11)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0820 (8)	0.1623 (13)	0.0843 (8)	−0.0148 (8)	0.0124 (7)	−0.0280 (9)
Cl2	0.0660 (7)	0.233 (2)	0.0930 (9)	−0.0111 (9)	−0.0010 (7)	−0.0328 (11)
O1	0.0329 (11)	0.0577 (14)	0.0635 (15)	−0.0010 (9)	0.0056 (10)	−0.0061 (12)
O2	0.0333 (11)	0.0671 (15)	0.0482 (14)	0.0041 (10)	−0.0009 (10)	0.0057 (12)
N1	0.0339 (13)	0.0450 (16)	0.0474 (16)	0.0014 (12)	0.0002 (11)	−0.0052 (13)
N2	0.0332 (14)	0.0484 (17)	0.0462 (16)	0.0004 (13)	0.0021 (12)	0.0020 (12)
N3	0.0324 (13)	0.0541 (16)	0.0425 (15)	0.0037 (11)	0.0029 (11)	0.0073 (13)
N4	0.0325 (12)	0.0496 (15)	0.0399 (15)	0.0042 (11)	0.0018 (11)	0.0035 (13)
C1	0.0360 (15)	0.0491 (19)	0.0434 (19)	0.0038 (15)	−0.0012 (14)	−0.0071 (15)
C2	0.0333 (15)	0.0434 (18)	0.0432 (18)	0.0052 (14)	−0.0014 (13)	−0.0004 (15)
C11	0.0365 (15)	0.0438 (19)	0.058 (2)	0.0020 (13)	0.0077 (15)	−0.0050 (17)
C12	0.0479 (19)	0.051 (2)	0.065 (2)	0.0089 (16)	−0.0008 (17)	−0.0021 (18)
C13	0.059 (2)	0.061 (3)	0.089 (3)	0.0135 (19)	0.002 (2)	0.004 (2)
C14	0.064 (3)	0.065 (3)	0.113 (4)	0.015 (2)	0.015 (3)	−0.004 (3)
C15	0.062 (2)	0.061 (3)	0.096 (3)	−0.006 (2)	0.021 (2)	−0.036 (3)
C16	0.0474 (18)	0.061 (2)	0.062 (2)	−0.0074 (17)	0.0105 (18)	−0.022 (2)
C17	0.085 (3)	0.069 (3)	0.060 (3)	0.008 (2)	−0.015 (2)	−0.007 (2)
C18	0.064 (2)	0.098 (3)	0.058 (3)	−0.010 (2)	0.005 (2)	−0.027 (2)
C21	0.0327 (15)	0.0456 (18)	0.049 (2)	0.0018 (14)	−0.0019 (14)	−0.0080 (16)
C22	0.0483 (18)	0.046 (2)	0.053 (2)	−0.0005 (16)	0.0012 (16)	0.0014 (17)
C23	0.066 (2)	0.055 (2)	0.068 (3)	−0.0045 (19)	0.009 (2)	0.005 (2)
C24	0.064 (2)	0.048 (2)	0.086 (3)	−0.0095 (18)	0.007 (2)	−0.005 (2)
C25	0.050 (2)	0.061 (2)	0.078 (3)	−0.0065 (17)	−0.0006 (19)	−0.025 (2)
C26	0.0363 (16)	0.063 (2)	0.048 (2)	0.0008 (15)	0.0034 (15)	−0.0074 (18)
C27	0.051 (2)	0.084 (3)	0.051 (2)	−0.0011 (19)	−0.0030 (17)	−0.012 (2)
C28	0.084 (3)	0.070 (3)	0.049 (2)	−0.009 (2)	−0.0037 (19)	0.0017 (19)
C31	0.0339 (15)	0.057 (2)	0.0327 (16)	0.0000 (14)	−0.0027 (13)	0.0086 (15)
C32	0.0471 (19)	0.056 (2)	0.0391 (19)	0.0010 (15)	−0.0064 (15)	0.0115 (16)
C33	0.058 (2)	0.065 (2)	0.052 (2)	−0.0081 (18)	−0.0047 (19)	0.019 (2)
C34	0.052 (2)	0.094 (3)	0.045 (2)	−0.014 (2)	0.0003 (17)	0.026 (2)
C35	0.0485 (18)	0.085 (3)	0.0396 (19)	−0.0058 (19)	0.0024 (16)	−0.0015 (19)
C36	0.0417 (16)	0.059 (2)	0.0405 (19)	−0.0029 (15)	−0.0019 (15)	−0.0061 (16)
C37	0.071 (2)	0.052 (2)	0.057 (2)	0.0046 (18)	−0.0014 (19)	0.0001 (18)
C38	0.060 (2)	0.069 (3)	0.064 (2)	−0.0091 (19)	0.0111 (19)	−0.018 (2)
C41	0.0299 (14)	0.0482 (19)	0.0458 (19)	0.0032 (13)	0.0050 (13)	0.0102 (15)
C42	0.0420 (16)	0.049 (2)	0.062 (2)	0.0033 (15)	0.0008 (17)	0.0049 (18)
C43	0.052 (2)	0.056 (2)	0.093 (3)	0.0073 (18)	0.006 (2)	0.021 (2)
C44	0.052 (2)	0.088 (3)	0.071 (3)	0.007 (2)	−0.001 (2)	0.037 (3)
C45	0.049 (2)	0.093 (3)	0.044 (2)	−0.001 (2)	0.0002 (16)	0.018 (2)
C46	0.0398 (16)	0.059 (2)	0.0422 (19)	0.0007 (16)	−0.0011 (14)	0.0013 (17)
C47	0.081 (3)	0.053 (2)	0.088 (3)	−0.002 (2)	−0.006 (2)	−0.010 (2)
C48	0.069 (2)	0.069 (3)	0.057 (2)	−0.006 (2)	−0.0015 (19)	−0.009 (2)
C51	0.145 (5)	0.148 (5)	0.058 (3)	0.027 (4)	−0.028 (3)	−0.011 (3)

Cl1—C51	1.729 (6)	C26—C27	1.500 (5)
Cl2—C51	1.756 (7)	C27—H27a	0.98
O1—N1	1.357 (3)	C27—H27b	0.98
O2—N3	1.398 (3)	C27—H27c	0.98
O2—H2	1.05 (4)	C28—H28a	0.98
N1—C1	1.294 (4)	C28—H28b	0.98
N1—C11	1.449 (4)	C28—H28c	0.98
N2—C1	1.322 (4)	C31—C32	1.393 (5)
N2—C21	1.438 (4)	C31—C36	1.400 (5)
N2—H1	0.77 (4)	C32—C33	1.394 (5)
N3—C2	1.330 (4)	C32—C37	1.510 (5)
N3—C31	1.433 (4)	C33—C34	1.377 (5)
N4—C2	1.291 (4)	C33—H33	0.95
N4—C41	1.426 (4)	C34—C35	1.369 (5)
C1—H1a	0.95	C34—H34	0.95
C2—H2a	0.95	C35—C36	1.398 (5)
C11—C12	1.387 (5)	C35—H35	0.95
C11—C16	1.403 (5)	C36—C38	1.498 (5)
C12—C13	1.402 (5)	C37—H37a	0.98
C12—C17	1.487 (5)	C37—H37b	0.98
C13—C14	1.351 (6)	C37—H37c	0.98
C13—H13	0.95	C38—H38a	0.98
C14—C15	1.370 (7)	C38—H38b	0.98
C14—H14	0.95	C38—H38c	0.98
C15—C16	1.426 (6)	C41—C46	1.391 (4)
C15—H15	0.95	C41—C42	1.391 (4)
C16—C18	1.488 (6)	C42—C43	1.394 (5)
C17—H17a	0.98	C42—C47	1.502 (5)
C17—H17b	0.98	C43—C44	1.380 (6)
C17—H17c	0.98	C43—H43	0.95
C18—H18a	0.98	C44—C45	1.361 (6)
C18—H18b	0.98	C44—H44	0.95
C18—H18c	0.98	C45—C46	1.399 (5)
C21—C26	1.391 (5)	C45—H45	0.95
C21—C22	1.399 (5)	C46—C48	1.508 (5)
C22—C23	1.393 (5)	C47—H47a	0.98
C22—C28	1.504 (5)	C47—H47b	0.98
C23—C24	1.369 (6)	C47—H47c	0.98
C23—H23	0.95	C48—H48a	0.98
C24—C25	1.383 (6)	C48—H48b	0.98
C24—H24	0.95	C48—H48c	0.98
C25—C26	1.406 (5)	C51—H51a	0.99
C25—H25	0.95	C51—H51b	0.99
N3—O2—H2	109 (2)	C22—C28—H28B	109.5
C1—N1—O1	120.3 (2)	H28A—C28—H28B	109.5
C1—N1—C11	124.4 (2)	C22—C28—H28C	109.5
O1—N1—C11	115.3 (2)	H28A—C28—H28C	109.5
C1—N2—C21	122.7 (3)	H28B—C28—H28C	109.5
C1—N2—H1	123 (3)	C32—C31—C36	122.5 (3)
C21—N2—H1	114 (3)	C32—C31—N3	118.2 (3)
C2—N3—O2	118.6 (2)	C36—C31—N3	119.3 (3)
C2—N3—C31	124.4 (2)	C31—C32—C33	118.0 (3)
O2—N3—C31	115.6 (2)	C31—C32—C37	121.3 (3)
C2—N4—C41	117.5 (2)	C33—C32—C37	120.7 (3)
N1—C1—N2	122.2 (3)	C34—C33—C32	120.5 (3)
N1—C1—H1A	118.9	C34—C33—H33	119.8
N2—C1—H1A	118.9	C32—C33—H33	119.8
N4—C2—N3	125.0 (3)	C35—C34—C33	120.7 (3)
N4—C2—H2A	117.5	C35—C34—H34	119.6
N3—C2—H2A	117.5	C33—C34—H34	119.6
C12—C11—C16	124.1 (3)	C34—C35—C36	121.3 (3)
C12—C11—N1	117.9 (3)	C34—C35—H35	119.4
C16—C11—N1	117.9 (3)	C36—C35—H35	119.4
C11—C12—C13	117.6 (3)	C35—C36—C31	117.0 (3)
C11—C12—C17	122.2 (3)	C35—C36—C38	121.8 (3)
C13—C12—C17	120.2 (4)	C31—C36—C38	121.1 (3)
C14—C13—C12	120.2 (4)	C32—C37—H37A	109.5
C14—C13—H13	119.9	C32—C37—H37B	109.5
C12—C13—H13	119.9	H37A—C37—H37B	109.5
C13—C14—C15	122.2 (4)	C32—C37—H37C	109.5
C13—C14—H14	118.9	H37A—C37—H37C	109.5
C15—C14—H14	118.9	H37B—C37—H37C	109.5
C14—C15—C16	120.8 (4)	C36—C38—H38A	109.5
C14—C15—H15	119.6	C36—C38—H38B	109.5
C16—C15—H15	119.6	H38A—C38—H38B	109.5
C11—C16—C15	115.1 (4)	C36—C38—H38C	109.5
C11—C16—C18	121.2 (3)	H38A—C38—H38C	109.5
C15—C16—C18	123.6 (4)	H38B—C38—H38C	109.5
C12—C17—H17A	109.5	C46—C41—C42	121.4 (3)
C12—C17—H17B	109.5	C46—C41—N4	119.6 (3)
H17A—C17—H17B	109.5	C42—C41—N4	118.9 (3)
C12—C17—H17C	109.5	C41—C42—C43	118.3 (3)
H17A—C17—H17C	109.5	C41—C42—C47	121.2 (3)
H17B—C17—H17C	109.5	C43—C42—C47	120.5 (3)
C16—C18—H18A	109.5	C44—C43—C42	121.1 (4)
C16—C18—H18B	109.5	C44—C43—H43	119.5
H18A—C18—H18B	109.5	C42—C43—H43	119.5
C16—C18—H18C	109.5	C45—C44—C43	119.6 (4)
H18A—C18—H18C	109.5	C45—C44—H44	120.2
H18B—C18—H18C	109.5	C43—C44—H44	120.2
C26—C21—C22	122.5 (3)	C44—C45—C46	121.6 (4)
C26—C21—N2	118.6 (3)	C44—C45—H45	119.2
C22—C21—N2	118.9 (3)	C46—C45—H45	119.2
C23—C22—C21	117.8 (3)	C41—C46—C45	118.0 (3)
C23—C22—C28	121.2 (3)	C41—C46—C48	120.9 (3)
C21—C22—C28	121.0 (3)	C45—C46—C48	121.2 (3)
C24—C23—C22	121.0 (4)	C42—C47—H47A	109.5
C24—C23—H23	119.5	C42—C47—H47B	109.5
C22—C23—H23	119.5	H47A—C47—H47B	109.5
C23—C24—C25	120.5 (3)	C42—C47—H47C	109.5
C23—C24—H24	119.7	H47A—C47—H47C	109.5
C25—C24—H24	119.7	H47B—C47—H47C	109.5
C24—C25—C26	120.7 (3)	C46—C48—H48A	109.5
C24—C25—H25	119.6	C46—C48—H48B	109.5
C26—C25—H25	119.6	H48A—C48—H48B	109.5
C21—C26—C25	117.3 (3)	C46—C48—H48C	109.5
C21—C26—C27	121.2 (3)	H48A—C48—H48C	109.5
C25—C26—C27	121.4 (3)	H48B—C48—H48C	109.5
C26—C27—H27A	109.5	CL1—C51—CL2	110.8 (3)
C26—C27—H27B	109.5	CL1—C51—H51A	109.5
H27A—C27—H27B	109.5	CL2—C51—H51A	109.5
C26—C27—H27C	109.5	CL1—C51—H51B	109.5
H27A—C27—H27C	109.5	CL2—C51—H51B	109.5
H27B—C27—H27C	109.5	H51A—C51—H51B	108.1
C22—C28—H28A	109.5
O1—N1—C1—N2	0.0 (4)	N2—C21—C26—C27	−0.3 (4)
C11—N1—C1—N2	−179.4 (3)	C24—C25—C26—C21	1.3 (5)
C21—N2—C1—N1	174.6 (3)	C24—C25—C26—C27	−177.4 (3)
C41—N4—C2—N3	174.3 (3)	C2—N3—C31—C32	118.6 (3)
O2—N3—C2—N4	2.8 (5)	O2—N3—C31—C32	−75.2 (4)
C31—N3—C2—N4	168.5 (3)	C2—N3—C31—C36	−63.1 (4)
C1—N1—C11—C12	94.1 (4)	O2—N3—C31—C36	103.1 (3)
O1—N1—C11—C12	−85.3 (3)	C36—C31—C32—C33	0.8 (5)
C1—N1—C11—C16	−90.7 (4)	N3—C31—C32—C33	179.0 (3)
O1—N1—C11—C16	89.9 (3)	C36—C31—C32—C37	179.7 (3)
C16—C11—C12—C13	−0.2 (5)	N3—C31—C32—C37	−2.0 (4)
N1—C11—C12—C13	174.6 (3)	C31—C32—C33—C34	1.0 (5)
C16—C11—C12—C17	−179.5 (3)	C37—C32—C33—C34	−177.9 (3)
N1—C11—C12—C17	−4.7 (5)	C32—C33—C34—C35	−1.3 (5)
C11—C12—C13—C14	1.5 (6)	C33—C34—C35—C36	−0.3 (5)
C17—C12—C13—C14	−179.2 (4)	C34—C35—C36—C31	2.0 (5)
C12—C13—C14—C15	−2.0 (6)	C34—C35—C36—C38	−177.4 (3)
C13—C14—C15—C16	1.1 (6)	C32—C31—C36—C35	−2.2 (4)
C12—C11—C16—C15	−0.6 (5)	N3—C31—C36—C35	179.5 (3)
N1—C11—C16—C15	−175.4 (3)	C32—C31—C36—C38	177.1 (3)
C12—C11—C16—C18	179.7 (3)	N3—C31—C36—C38	−1.1 (5)
N1—C11—C16—C18	4.9 (5)	C2—N4—C41—C46	−80.7 (3)
C14—C15—C16—C11	0.2 (5)	C2—N4—C41—C42	102.9 (3)
C14—C15—C16—C18	179.9 (4)	C46—C41—C42—C43	1.4 (5)
C1—N2—C21—C26	−90.6 (4)	N4—C41—C42—C43	177.7 (3)
C1—N2—C21—C22	91.6 (4)	C46—C41—C42—C47	−177.1 (3)
C26—C21—C22—C23	0.6 (5)	N4—C41—C42—C47	−0.8 (4)
N2—C21—C22—C23	178.3 (3)	C41—C42—C43—C44	−0.1 (5)
C26—C21—C22—C28	−179.4 (3)	C47—C42—C43—C44	178.4 (3)
N2—C21—C22—C28	−1.7 (5)	C42—C43—C44—C45	−0.9 (6)
C21—C22—C23—C24	0.1 (5)	C43—C44—C45—C46	0.8 (5)
C28—C22—C23—C24	−179.9 (4)	C42—C41—C46—C45	−1.6 (4)
C22—C23—C24—C25	−0.1 (6)	N4—C41—C46—C45	−177.9 (3)
C23—C24—C25—C26	−0.7 (6)	C42—C41—C46—C48	177.6 (3)
C22—C21—C26—C25	−1.3 (5)	N4—C41—C46—C48	1.3 (4)
N2—C21—C26—C25	−179.0 (3)	C44—C45—C46—C41	0.5 (5)
C22—C21—C26—C27	177.4 (3)	C44—C45—C46—C48	−178.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···N4i	0.77 (4)	2.12 (4)	2.875 (4)	166 (4)
O2—H2···O1ii	1.05 (4)	1.48 (4)	2.508 (3)	168 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯N4i	0.77 (4)	2.12 (4)	2.875 (4)	166 (4)
O2—H2⋯O1ii	1.05 (4)	1.48 (4)	2.508 (3)	168 (3)

Symmetry codes: (i) ; (ii) .