2-[(2,4-Dihydroxy-benzyl-idene)amino]-3',6'-bis-(ethyl-amino)spiro-[isoindoline-1,9'-xanthen]-3-one.

The title compound, C(35)H(36)N(4)O(4), was prepared as a spiro-lactam ring formation of rhodamine B dye for comparison with a ring-opened form. The xanthene ring system is approximately planar. The r.m.s. deviation from planarity is 0.064 (6) Å for the xanthene ring. The dihedral angles formed by the spiro-lactam and 2,4-dihydroxy-benzene rings with the xanthene ring system are 86.6 (9) and 88.0 (9)°, respectively.

Related literature

For the structures of rhodamine derivatives bearing a lactam moiety, see: Deng et al. (2009 ▶); Kwon et al. (2005 ▶); Tian & Peng (2008 ▶); Wu et al. (2007 ▶); Xu et al. (2009 ▶); Zhang et al. (2008 ▶).

Experimental

Crystal data

C35H36N4O4

M = 576.68

Monoclinic,

a = 9.4461 (4) Å

b = 26.6905 (12) Å

c = 12.2453 (5) Å

β = 104.423 (2)°

V = 2990.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.25 × 0.23 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.979, T max = 0.982

15630 measured reflections

5310 independent reflections

2162 reflections with I > 2σ(I)

R int = 0.087

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.215

S = 1.02

5310 reflections

393 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810015126/jh2147sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015126/jh2147Isup2.hkl

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

C35H36N4O4	F(000) = 1224
Mr = 576.68	Dx = 1.281 Mg m−3Dm = 1.281 Mg m−3Dm measured by not measured
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.4461 (4) Å	Cell parameters from 922 reflections
b = 26.6905 (12) Å	θ = 2.3–17.5°
c = 12.2453 (5) Å	µ = 0.09 mm−1
β = 104.423 (2)°	T = 296 K
V = 2990.0 (2) Å3	Block, colorless
Z = 4	0.25 × 0.23 × 0.21 mm

Bruker APEXII CCD diffractometer	5310 independent reflections
Radiation source: fine-focus sealed tube	2162 reflections with I > 2σ(I)
graphite	Rint = 0.087
φ and ω scans	θmax = 25.1°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→7
Tmin = 0.979, Tmax = 0.982	k = −31→30
15630 measured reflections	l = −14→14

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.215	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0857P)2] where P = (Fo2 + 2Fc2)/3
5310 reflections	(Δ/σ)max < 0.001
393 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.3223 (7)	0.6153 (3)	0.9041 (5)	0.133 (2)
H1A	0.3370	0.6138	0.8294	0.199*
H1B	0.3921	0.5940	0.9532	0.199*
H1C	0.3348	0.6491	0.9313	0.199*
C2	0.1753 (7)	0.5984 (2)	0.9018 (4)	0.103 (2)
H2A	0.1604	0.5990	0.9774	0.124*
H2B	0.1613	0.5644	0.8736	0.124*
C3	0.0711 (7)	0.6969 (3)	0.9716 (6)	0.157 (3)
H3A	0.0060	0.7223	0.9861	0.236*
H3B	0.1598	0.7123	0.9635	0.236*
H3C	0.0932	0.6737	1.0335	0.236*
C4	0.0080 (7)	0.6728 (3)	0.8778 (5)	0.142 (3)
H4A	−0.0179	0.6983	0.8199	0.170*
H4B	−0.0835	0.6601	0.8892	0.170*
C5	0.0391 (5)	0.62734 (19)	0.7115 (4)	0.0658 (13)
C6	−0.0518 (5)	0.66052 (17)	0.6381 (4)	0.0682 (14)
H6	−0.0908	0.6879	0.6675	0.082*
C7	−0.0847 (4)	0.65369 (17)	0.5250 (4)	0.0619 (12)
H7	−0.1472	0.6764	0.4792	0.074*
C8	−0.0288 (4)	0.61409 (15)	0.4742 (3)	0.0472 (10)
C9	0.0635 (4)	0.58217 (15)	0.5468 (3)	0.0501 (11)
C10	0.0969 (5)	0.58814 (18)	0.6619 (4)	0.0651 (13)
H10	0.1595	0.5654	0.7076	0.078*
C11	0.1123 (4)	0.53531 (15)	0.3966 (3)	0.0490 (11)
C12	0.1954 (5)	0.49728 (16)	0.3683 (4)	0.0580 (12)
H12	0.2569	0.4789	0.4253	0.070*
C13	0.1896 (4)	0.48581 (17)	0.2564 (4)	0.0562 (11)
C14	0.3593 (6)	0.41531 (19)	0.3137 (4)	0.0833 (16)
H14A	0.3737	0.3835	0.2797	0.100*
H14B	0.3058	0.4088	0.3703	0.100*
C15	0.5050 (6)	0.4366 (2)	0.3703 (5)	0.110 (2)
H15A	0.5603	0.4420	0.3154	0.165*
H15B	0.5563	0.4135	0.4265	0.165*
H15C	0.4920	0.4678	0.4053	0.165*
C16	0.3493 (8)	0.4691 (3)	0.0552 (6)	0.142 (3)
H16A	0.3051	0.5018	0.0458	0.213*
H16B	0.3526	0.4560	−0.0172	0.213*
H16C	0.4468	0.4716	0.1023	0.213*
C17	0.2632 (7)	0.4358 (2)	0.1076 (5)	0.1038 (19)
H17A	0.2971	0.4017	0.1033	0.125*
H17B	0.1619	0.4373	0.0650	0.125*
C18	0.0957 (5)	0.51575 (18)	0.1741 (4)	0.0656 (13)
H18	0.0884	0.5099	0.0980	0.079*
C19	0.0150 (5)	0.55344 (17)	0.2056 (4)	0.0637 (13)
H19	−0.0455	0.5726	0.1496	0.076*
C20	0.0197 (4)	0.56410 (15)	0.3172 (3)	0.0471 (10)
C21	−0.0665 (4)	0.60681 (15)	0.3484 (3)	0.0477 (10)
C22	−0.2316 (4)	0.60356 (16)	0.2994 (3)	0.0493 (10)
C23	−0.3254 (5)	0.56787 (17)	0.3198 (3)	0.0613 (12)
H23	−0.2916	0.5398	0.3635	0.074*
C24	−0.4729 (5)	0.57535 (19)	0.2726 (4)	0.0709 (14)
H24	−0.5396	0.5519	0.2859	0.085*
C25	−0.5239 (5)	0.6164 (2)	0.2065 (4)	0.0705 (14)
H25	−0.6240	0.6206	0.1777	0.085*
C26	−0.4286 (5)	0.65122 (17)	0.1826 (4)	0.0640 (13)
H26	−0.4621	0.6785	0.1359	0.077*
C27	−0.2806 (4)	0.64420 (15)	0.2306 (3)	0.0489 (11)
C28	−0.1560 (4)	0.67624 (17)	0.2241 (4)	0.0535 (11)
C29	0.1563 (5)	0.70297 (18)	0.2756 (4)	0.0663 (13)
H29	0.0997	0.7142	0.2066	0.080*
C30	0.3057 (5)	0.72331 (17)	0.3196 (4)	0.0587 (12)
C31	0.3612 (6)	0.75637 (19)	0.2560 (4)	0.0783 (15)
H31	0.3067	0.7650	0.1842	0.094*
C32	0.4987 (6)	0.7771 (2)	0.2981 (5)	0.0872 (17)
H32	0.5375	0.7990	0.2541	0.105*
C33	0.5776 (5)	0.7650 (2)	0.4060 (5)	0.0733 (14)
C34	0.5267 (5)	0.73148 (19)	0.4713 (4)	0.0706 (14)
H34	0.5822	0.7228	0.5427	0.085*
C35	0.3870 (5)	0.71047 (17)	0.4268 (4)	0.0649 (13)
N1	0.0690 (5)	0.63236 (18)	0.8272 (4)	0.0940 (15)
N2	0.2709 (4)	0.44784 (15)	0.2266 (3)	0.0749 (12)
N3	−0.0361 (3)	0.65359 (12)	0.2909 (3)	0.0519 (9)
N4	0.1058 (4)	0.67119 (13)	0.3293 (3)	0.0587 (10)
O1	−0.1568 (3)	0.71531 (11)	0.1705 (3)	0.0705 (9)
O2	0.7101 (4)	0.78780 (16)	0.4427 (3)	0.1002 (13)
H2	0.7411	0.7832	0.5106	0.150*
O3	0.3414 (4)	0.67909 (15)	0.4958 (3)	0.0928 (12)
H3	0.2595	0.6687	0.4647	0.139*
O4	0.1295 (3)	0.54163 (11)	0.5103 (2)	0.0666 (9)

	U11	U22	U33	U12	U13	U23
C1	0.120 (6)	0.175 (7)	0.096 (5)	0.019 (5)	0.013 (4)	−0.032 (5)
C2	0.098 (5)	0.142 (6)	0.069 (4)	−0.001 (4)	0.022 (4)	−0.030 (4)
C3	0.114 (6)	0.197 (8)	0.153 (7)	0.006 (5)	0.019 (5)	−0.095 (6)
C4	0.121 (5)	0.196 (8)	0.091 (5)	0.065 (5)	−0.009 (4)	−0.077 (5)
C5	0.049 (3)	0.086 (4)	0.056 (3)	0.009 (3)	0.000 (2)	−0.021 (3)
C6	0.054 (3)	0.072 (4)	0.074 (3)	0.012 (2)	0.006 (3)	−0.022 (3)
C7	0.055 (3)	0.058 (3)	0.064 (3)	0.013 (2)	−0.003 (2)	0.001 (2)
C8	0.038 (2)	0.048 (3)	0.050 (3)	−0.0026 (19)	0.001 (2)	0.000 (2)
C9	0.044 (3)	0.050 (3)	0.051 (3)	0.010 (2)	0.002 (2)	−0.004 (2)
C10	0.060 (3)	0.079 (4)	0.048 (3)	0.016 (2)	−0.002 (2)	−0.006 (3)
C11	0.055 (3)	0.050 (3)	0.038 (3)	0.001 (2)	0.003 (2)	0.002 (2)
C12	0.059 (3)	0.060 (3)	0.049 (3)	0.008 (2)	0.002 (2)	0.004 (2)
C13	0.051 (3)	0.058 (3)	0.057 (3)	0.001 (2)	0.009 (2)	−0.002 (2)
C14	0.096 (4)	0.068 (4)	0.090 (4)	0.023 (3)	0.032 (3)	−0.011 (3)
C15	0.078 (4)	0.108 (5)	0.139 (5)	0.017 (4)	0.018 (4)	0.001 (4)
C16	0.118 (6)	0.199 (8)	0.121 (6)	0.016 (5)	0.053 (5)	0.015 (5)
C17	0.114 (5)	0.110 (5)	0.093 (5)	0.028 (4)	0.037 (4)	−0.003 (4)
C18	0.068 (3)	0.080 (4)	0.045 (3)	0.013 (3)	0.008 (2)	0.000 (2)
C19	0.063 (3)	0.070 (3)	0.051 (3)	0.015 (2)	0.001 (2)	0.010 (2)
C20	0.045 (3)	0.051 (3)	0.043 (2)	0.000 (2)	0.006 (2)	0.006 (2)
C21	0.037 (2)	0.049 (3)	0.051 (3)	−0.0030 (19)	0.0008 (19)	0.004 (2)
C22	0.043 (3)	0.051 (3)	0.048 (2)	−0.006 (2)	0.000 (2)	−0.003 (2)
C23	0.047 (3)	0.068 (3)	0.062 (3)	−0.007 (2)	0.000 (2)	0.009 (2)
C24	0.054 (3)	0.078 (4)	0.075 (3)	−0.017 (2)	0.003 (3)	0.005 (3)
C25	0.040 (3)	0.087 (4)	0.076 (3)	−0.007 (3)	−0.003 (2)	0.006 (3)
C26	0.048 (3)	0.066 (3)	0.071 (3)	0.006 (2)	0.002 (2)	0.010 (3)
C27	0.039 (3)	0.049 (3)	0.052 (3)	−0.001 (2)	0.000 (2)	0.006 (2)
C28	0.051 (3)	0.051 (3)	0.055 (3)	0.003 (2)	0.006 (2)	0.004 (2)
C29	0.061 (3)	0.068 (4)	0.063 (3)	0.003 (3)	0.002 (3)	−0.003 (3)
C30	0.058 (3)	0.062 (3)	0.053 (3)	−0.003 (2)	0.007 (2)	−0.001 (2)
C31	0.087 (4)	0.085 (4)	0.066 (3)	−0.012 (3)	0.026 (3)	0.009 (3)
C32	0.079 (4)	0.102 (5)	0.081 (4)	−0.039 (3)	0.021 (3)	−0.010 (3)
C33	0.052 (3)	0.092 (4)	0.077 (4)	−0.024 (3)	0.018 (3)	−0.018 (3)
C34	0.054 (3)	0.084 (4)	0.071 (3)	−0.018 (3)	0.012 (3)	−0.009 (3)
C35	0.069 (3)	0.055 (3)	0.078 (4)	−0.009 (2)	0.032 (3)	0.005 (3)
N1	0.084 (3)	0.123 (4)	0.063 (3)	0.032 (3)	−0.004 (2)	−0.031 (3)
N2	0.083 (3)	0.080 (3)	0.061 (3)	0.027 (2)	0.016 (2)	−0.002 (2)
N3	0.037 (2)	0.051 (2)	0.062 (2)	−0.0056 (17)	0.0025 (17)	0.0110 (18)
N4	0.053 (2)	0.050 (2)	0.072 (3)	−0.0094 (18)	0.015 (2)	0.010 (2)
O1	0.058 (2)	0.061 (2)	0.084 (2)	0.0002 (15)	0.0007 (16)	0.0266 (18)
O2	0.070 (2)	0.137 (3)	0.092 (3)	−0.056 (2)	0.016 (2)	−0.017 (3)
O3	0.075 (3)	0.109 (3)	0.081 (2)	−0.028 (2)	−0.0046 (19)	0.027 (2)
O4	0.078 (2)	0.069 (2)	0.0468 (19)	0.0292 (17)	0.0047 (16)	0.0023 (16)

C1—C2	1.453 (7)	C16—H16B	0.9600
C1—H1A	0.9600	C16—H16C	0.9600
C1—H1B	0.9600	C17—N2	1.476 (6)
C1—H1C	0.9600	C17—H17A	0.9700
C2—N1	1.486 (7)	C17—H17B	0.9700
C2—H2A	0.9700	C18—C19	1.374 (6)
C2—H2B	0.9700	C18—H18	0.9300
C3—C4	1.323 (7)	C19—C20	1.386 (5)
C3—H3A	0.9600	C19—H19	0.9300
C3—H3B	0.9600	C20—C21	1.504 (5)
C3—H3C	0.9600	C21—N3	1.496 (5)
C4—N1	1.434 (6)	C21—C22	1.527 (5)
C4—H4A	0.9700	C22—C23	1.366 (5)
C4—H4B	0.9700	C22—C27	1.381 (5)
C5—N1	1.380 (5)	C23—C24	1.384 (6)
C5—C10	1.388 (6)	C23—H23	0.9300
C5—C6	1.395 (6)	C24—C25	1.376 (6)
C6—C7	1.354 (5)	C24—H24	0.9300
C6—H6	0.9300	C25—C26	1.376 (6)
C7—C8	1.396 (5)	C25—H25	0.9300
C7—H7	0.9300	C26—C27	1.388 (5)
C8—C9	1.375 (5)	C26—H26	0.9300
C8—C21	1.504 (5)	C27—C28	1.473 (5)
C9—C10	1.375 (5)	C28—O1	1.231 (5)
C9—O4	1.377 (4)	C28—N3	1.362 (5)
C10—H10	0.9300	C29—N4	1.240 (5)
C11—C20	1.370 (5)	C29—C30	1.482 (6)
C11—O4	1.371 (4)	C29—H29	0.9300
C11—C12	1.380 (5)	C30—C31	1.365 (6)
C12—C13	1.391 (5)	C30—C35	1.389 (6)
C12—H12	0.9300	C31—C32	1.388 (6)
C13—N2	1.374 (5)	C31—H31	0.9300
C13—C18	1.413 (6)	C32—C33	1.385 (7)
C14—N2	1.465 (6)	C32—H32	0.9300
C14—C15	1.490 (7)	C33—O2	1.363 (5)
C14—H14A	0.9700	C33—C34	1.364 (6)
C14—H14B	0.9700	C34—C35	1.413 (6)
C15—H15A	0.9600	C34—H34	0.9300
C15—H15B	0.9600	C35—O3	1.335 (5)
C15—H15C	0.9600	N3—N4	1.388 (4)
C16—C17	1.458 (7)	O2—H2	0.8200
C16—H16A	0.9600	O3—H3	0.8200
C2—C1—H1A	109.5	N2—C17—H17B	108.8
C2—C1—H1B	109.5	H17A—C17—H17B	107.7
H1A—C1—H1B	109.5	C19—C18—C13	120.5 (4)
C2—C1—H1C	109.5	C19—C18—H18	119.8
H1A—C1—H1C	109.5	C13—C18—H18	119.8
H1B—C1—H1C	109.5	C18—C19—C20	122.9 (4)
C1—C2—N1	108.6 (5)	C18—C19—H19	118.5
C1—C2—H2A	110.0	C20—C19—H19	118.5
N1—C2—H2A	110.0	C11—C20—C19	116.3 (4)
C1—C2—H2B	110.0	C11—C20—C21	122.3 (4)
N1—C2—H2B	110.0	C19—C20—C21	121.3 (4)
H2A—C2—H2B	108.3	N3—C21—C8	110.5 (3)
C4—C3—H3A	109.5	N3—C21—C20	109.5 (3)
C4—C3—H3B	109.5	C8—C21—C20	110.6 (3)
H3A—C3—H3B	109.5	N3—C21—C22	99.2 (3)
C4—C3—H3C	109.5	C8—C21—C22	111.6 (3)
H3A—C3—H3C	109.5	C20—C21—C22	114.9 (3)
H3B—C3—H3C	109.5	C23—C22—C27	121.7 (4)
C3—C4—N1	126.8 (6)	C23—C22—C21	127.8 (4)
C3—C4—H4A	105.6	C27—C22—C21	110.5 (3)
N1—C4—H4A	105.6	C22—C23—C24	117.1 (4)
C3—C4—H4B	105.6	C22—C23—H23	121.5
N1—C4—H4B	105.6	C24—C23—H23	121.5
H4A—C4—H4B	106.1	C25—C24—C23	121.9 (4)
N1—C5—C10	121.3 (4)	C25—C24—H24	119.0
N1—C5—C6	122.4 (4)	C23—C24—H24	119.0
C10—C5—C6	116.3 (4)	C26—C25—C24	120.8 (4)
C7—C6—C5	121.4 (4)	C26—C25—H25	119.6
C7—C6—H6	119.3	C24—C25—H25	119.6
C5—C6—H6	119.3	C25—C26—C27	117.5 (4)
C6—C7—C8	122.9 (4)	C25—C26—H26	121.2
C6—C7—H7	118.6	C27—C26—H26	121.2
C8—C7—H7	118.6	C22—C27—C26	120.9 (4)
C9—C8—C7	115.5 (4)	C22—C27—C28	109.7 (4)
C9—C8—C21	122.2 (4)	C26—C27—C28	129.3 (4)
C7—C8—C21	122.4 (4)	O1—C28—N3	126.1 (4)
C8—C9—C10	122.5 (4)	O1—C28—C27	128.4 (4)
C8—C9—O4	122.8 (4)	N3—C28—C27	105.4 (4)
C10—C9—O4	114.6 (4)	N4—C29—C30	121.0 (4)
C9—C10—C5	121.4 (4)	N4—C29—H29	119.5
C9—C10—H10	119.3	C30—C29—H29	119.5
C5—C10—H10	119.3	C31—C30—C35	119.9 (4)
C20—C11—O4	123.0 (4)	C31—C30—C29	119.7 (4)
C20—C11—C12	122.4 (4)	C35—C30—C29	120.4 (4)
O4—C11—C12	114.5 (4)	C30—C31—C32	120.2 (5)
C11—C12—C13	121.6 (4)	C30—C31—H31	119.9
C11—C12—H12	119.2	C32—C31—H31	119.9
C13—C12—H12	119.2	C33—C32—C31	119.6 (5)
N2—C13—C12	122.4 (4)	C33—C32—H32	120.2
N2—C13—C18	121.4 (4)	C31—C32—H32	120.2
C12—C13—C18	116.2 (4)	O2—C33—C34	121.9 (5)
N2—C14—C15	114.0 (5)	O2—C33—C32	116.2 (5)
N2—C14—H14A	108.8	C34—C33—C32	121.9 (4)
C15—C14—H14A	108.8	C33—C34—C35	117.8 (4)
N2—C14—H14B	108.8	C33—C34—H34	121.1
C15—C14—H14B	108.8	C35—C34—H34	121.1
H14A—C14—H14B	107.7	O3—C35—C30	124.3 (4)
C14—C15—H15A	109.5	O3—C35—C34	115.0 (4)
C14—C15—H15B	109.5	C30—C35—C34	120.7 (4)
H15A—C15—H15B	109.5	C5—N1—C4	121.0 (5)
C14—C15—H15C	109.5	C5—N1—C2	120.4 (4)
H15A—C15—H15C	109.5	C4—N1—C2	118.4 (4)
H15B—C15—H15C	109.5	C13—N2—C14	119.9 (4)
C17—C16—H16A	109.5	C13—N2—C17	121.9 (4)
C17—C16—H16B	109.5	C14—N2—C17	117.9 (4)
H16A—C16—H16B	109.5	C28—N3—N4	129.9 (3)
C17—C16—H16C	109.5	C28—N3—C21	115.1 (3)
H16A—C16—H16C	109.5	N4—N3—C21	113.9 (3)
H16B—C16—H16C	109.5	C29—N4—N3	121.3 (4)
C16—C17—N2	114.0 (5)	C33—O2—H2	109.5
C16—C17—H17A	108.8	C35—O3—H3	109.5
N2—C17—H17A	108.8	C11—O4—C9	118.5 (3)
C16—C17—H17B	108.8
N1—C5—C6—C7	−177.1 (4)	C25—C26—C27—C28	−176.9 (4)
C10—C5—C6—C7	1.8 (7)	C22—C27—C28—O1	179.4 (4)
C5—C6—C7—C8	−1.2 (7)	C26—C27—C28—O1	−3.2 (8)
C6—C7—C8—C9	−0.3 (6)	C22—C27—C28—N3	−0.6 (5)
C6—C7—C8—C21	179.8 (4)	C26—C27—C28—N3	176.8 (4)
C7—C8—C9—C10	1.1 (6)	N4—C29—C30—C31	176.7 (4)
C21—C8—C9—C10	−179.0 (4)	N4—C29—C30—C35	−5.8 (7)
C7—C8—C9—O4	−179.2 (4)	C35—C30—C31—C32	0.1 (7)
C21—C8—C9—O4	0.7 (6)	C29—C30—C31—C32	177.6 (5)
C8—C9—C10—C5	−0.4 (7)	C30—C31—C32—C33	−1.6 (8)
O4—C9—C10—C5	179.8 (4)	C31—C32—C33—O2	−178.3 (5)
N1—C5—C10—C9	177.9 (4)	C31—C32—C33—C34	2.7 (8)
C6—C5—C10—C9	−1.1 (7)	O2—C33—C34—C35	178.8 (4)
C20—C11—C12—C13	−0.2 (7)	C32—C33—C34—C35	−2.2 (8)
O4—C11—C12—C13	179.5 (4)	C31—C30—C35—O3	179.1 (5)
C11—C12—C13—N2	−179.5 (4)	C29—C30—C35—O3	1.6 (7)
C11—C12—C13—C18	0.9 (6)	C31—C30—C35—C34	0.3 (7)
N2—C13—C18—C19	179.8 (4)	C29—C30—C35—C34	−177.1 (4)
C12—C13—C18—C19	−0.7 (7)	C33—C34—C35—O3	−178.1 (4)
C13—C18—C19—C20	−0.3 (7)	C33—C34—C35—C30	0.7 (7)
O4—C11—C20—C19	179.6 (4)	C10—C5—N1—C4	−179.5 (5)
C12—C11—C20—C19	−0.8 (6)	C6—C5—N1—C4	−0.6 (8)
O4—C11—C20—C21	2.7 (6)	C10—C5—N1—C2	5.7 (7)
C12—C11—C20—C21	−177.6 (4)	C6—C5—N1—C2	−175.4 (5)
C18—C19—C20—C11	1.0 (6)	C3—C4—N1—C5	−145.1 (8)
C18—C19—C20—C21	177.9 (4)	C3—C4—N1—C2	29.7 (12)
C9—C8—C21—N3	−126.4 (4)	C1—C2—N1—C5	78.6 (6)
C7—C8—C21—N3	53.5 (5)	C1—C2—N1—C4	−96.3 (7)
C9—C8—C21—C20	−5.0 (5)	C12—C13—N2—C14	4.7 (7)
C7—C8—C21—C20	174.9 (4)	C18—C13—N2—C14	−175.8 (4)
C9—C8—C21—C22	124.3 (4)	C12—C13—N2—C17	179.7 (5)
C7—C8—C21—C22	−55.8 (5)	C18—C13—N2—C17	−0.8 (7)
C11—C20—C21—N3	125.3 (4)	C15—C14—N2—C13	−83.1 (6)
C19—C20—C21—N3	−51.4 (5)	C15—C14—N2—C17	101.7 (6)
C11—C20—C21—C8	3.4 (5)	C16—C17—N2—C13	79.7 (7)
C19—C20—C21—C8	−173.3 (4)	C16—C17—N2—C14	−105.3 (6)
C11—C20—C21—C22	−124.1 (4)	O1—C28—N3—N4	11.1 (7)
C19—C20—C21—C22	59.2 (5)	C27—C28—N3—N4	−168.9 (4)
N3—C21—C22—C23	179.7 (4)	O1—C28—N3—C21	178.8 (4)
C8—C21—C22—C23	−63.9 (6)	C27—C28—N3—C21	−1.2 (5)
C20—C21—C22—C23	63.1 (6)	C8—C21—N3—C28	−115.0 (4)
N3—C21—C22—C27	−2.5 (4)	C20—C21—N3—C28	122.9 (4)
C8—C21—C22—C27	113.9 (4)	C22—C21—N3—C28	2.2 (4)
C20—C21—C22—C27	−119.1 (4)	C8—C21—N3—N4	54.7 (4)
C27—C22—C23—C24	−2.9 (7)	C20—C21—N3—N4	−67.4 (4)
C21—C22—C23—C24	174.6 (4)	C22—C21—N3—N4	171.9 (3)
C22—C23—C24—C25	1.0 (7)	C30—C29—N4—N3	177.2 (4)
C23—C24—C25—C26	1.6 (8)	C28—N3—N4—C29	−27.2 (7)
C24—C25—C26—C27	−2.2 (7)	C21—N3—N4—C29	165.0 (4)
C23—C22—C27—C26	2.3 (7)	C20—C11—O4—C9	−7.5 (6)
C21—C22—C27—C26	−175.6 (4)	C12—C11—O4—C9	172.8 (4)
C23—C22—C27—C28	180.0 (4)	C8—C9—O4—C11	5.7 (6)
C21—C22—C27—C28	2.1 (5)	C10—C9—O4—C11	−174.5 (4)
C25—C26—C27—C22	0.3 (6)