[(2-{[3',6'-Bis(ethyl-amino)-2',7'-dimethyl-3-oxospiro-[1H-isoindole-1,9'-9H-xanthen]-2-yl}eth-yl)amino-meth-yl]phenol.

The title compound, C(35)H(38)N(4)O(3), was prepared as a spiro-lactam ring formation of rhodamine dye for comparison with a ring-opened form. The xanthene ring system is approximately planar. The dihedral angles formed by the spiro-lactam and phenol rings with the xanthene ring system are 85.7 and 109.4°, respectively. Each of the mol-ecules in the crystal structure contains one intra-molecular O-H⋯N hydrogen bond, and they form inter-molecular N-H⋯O hydrogen-bonded chains along the [100] direction. Weak inter-molecular C-H⋯O hydrogen-bonding contacts connect the infinite chains via crystallographic inversion centres to form a two-dimensional network.

Related literature

For related literature, see: Kwon et al. (2005 ▶); Wu et al. (2007 ▶); De Silva et al. (1997 ▶).

Experimental

Crystal data

C35H36N4O3

M = 560.68

Triclinic,

a = 11.6453 (5) Å

b = 11.8588 (3) Å

c = 12.9822 (3) Å

α = 116.3210 (10)°

β = 103.173 (2)°

γ = 98.337 (2)°

V = 1501.21 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 273 (2) K

0.30 × 0.30 × 0.25 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.976, T max = 0.980

9518 measured reflections

5018 independent reflections

3667 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.169

S = 1.01

5018 reflections

383 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Bruker, 1997 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807068742/si2058sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068742/si2058Isup2.hkl

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

C35H36N4O3	Z = 2
Mr = 560.68	F000 = 596
Triclinic, P1	Dx = 1.240 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 11.6453 (5) Å	Cell parameters from 2891 reflections
b = 11.8588 (3) Å	θ = 2.7–27.2º
c = 12.9822 (3) Å	µ = 0.08 mm−1
α = 116.3210 (10)º	T = 273 (2) K
β = 103.173 (2)º	Block, white
γ = 98.337 (2)º	0.30 × 0.30 × 0.25 mm
V = 1501.21 (8) Å3

Bruker APEXII CCD area-detector diffractometer	5018 independent reflections
Radiation source: fine-focus sealed tube	3667 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.020
T = 273(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.7º
Absorption correction: multi-scan(SADABS; Bruker, 1997)	h = −13→12
Tmin = 0.976, Tmax = 0.980	k = −14→13
9518 measured reflections	l = −15→15

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0943P)2 + 0.4133P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.056	(Δ/σ)max < 0.001
wR(F2) = 0.169	Δρmax = 0.55 e Å−3
S = 1.01	Δρmin = −0.34 e Å−3
5018 reflections	Extinction correction: none
383 parameters

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.

	x	y	z	Uiso*/Ueq
O1	0.61529 (16)	0.99784 (14)	0.12430 (14)	0.0552 (4)
O2	0.52746 (17)	1.55773 (17)	0.38418 (16)	0.0697 (5)
O3	0.10319 (17)	1.2888 (2)	−0.06993 (17)	0.0752 (6)
H3A	0.1732	1.3180	−0.0213	0.113*
N1	0.55473 (16)	1.35526 (16)	0.27576 (15)	0.0430 (4)
N2	0.34153 (17)	1.29474 (18)	−0.01746 (17)	0.0496 (5)
N3	0.88189 (19)	1.10924 (19)	−0.06256 (18)	0.0571 (5)
H3B	0.9285	1.1680	−0.0682	0.068*
N4	0.35515 (18)	0.83845 (18)	0.29282 (19)	0.0539 (5)
H4A	0.3082	0.8541	0.3369	0.065*
C1	0.6847 (2)	1.0985 (2)	0.11824 (19)	0.0440 (5)
C2	0.7442 (2)	1.0584 (2)	0.0336 (2)	0.0477 (6)
H2B	0.7345	0.9694	−0.0143	0.057*
C3	0.8187 (2)	1.1487 (2)	0.0184 (2)	0.0443 (5)
C4	0.82894 (19)	1.2838 (2)	0.0902 (2)	0.0439 (5)
C5	0.7681 (2)	1.3186 (2)	0.1733 (2)	0.0442 (5)
H5A	0.7758	1.4072	0.2205	0.053*
C6	0.69504 (19)	1.2290 (2)	0.19164 (19)	0.0413 (5)
C7	0.63690 (19)	1.2743 (2)	0.29058 (19)	0.0407 (5)
C8	0.56535 (19)	1.1577 (2)	0.29171 (19)	0.0413 (5)
C9	0.5015 (2)	1.1743 (2)	0.37370 (19)	0.0448 (5)
H9A	0.5057	1.2593	0.4294	0.054*
C10	0.4326 (2)	1.0719 (2)	0.3771 (2)	0.0448 (5)
C11	0.4261 (2)	0.9423 (2)	0.2921 (2)	0.0441 (5)
C12	0.4884 (2)	0.9238 (2)	0.2102 (2)	0.0477 (6)
H12A	0.4847	0.8392	0.1540	0.057*
C13	0.5566 (2)	1.0302 (2)	0.21049 (19)	0.0432 (5)
C14	0.9068 (2)	1.3854 (2)	0.0759 (2)	0.0593 (7)
H14A	0.8967	1.4698	0.1244	0.089*
H14B	0.8818	1.3633	−0.0080	0.089*
H14C	0.9916	1.3879	0.1023	0.089*
C15	0.8734 (3)	0.9726 (2)	−0.1390 (2)	0.0617 (7)
H15A	0.7899	0.9267	−0.1946	0.074*
H15B	0.8922	0.9328	−0.0884	0.074*
C16	0.9601 (3)	0.9574 (3)	−0.2109 (3)	0.0731 (8)
H16A	0.9549	0.8663	−0.2572	0.110*
H16B	1.0426	1.0050	−0.1563	0.110*
H16C	0.9382	0.9914	−0.2651	0.110*
C17	0.3645 (2)	1.0961 (2)	0.4661 (2)	0.0599 (7)
H17A	0.3775	1.1887	0.5149	0.090*
H17B	0.3941	1.0612	0.5177	0.090*
H17C	0.2783	1.0540	0.4229	0.090*
C18	0.3572 (2)	0.7054 (2)	0.2223 (2)	0.0558 (6)
H18A	0.4406	0.6995	0.2449	0.067*
H18B	0.3307	0.6794	0.1366	0.067*
C19	0.2740 (3)	0.6137 (3)	0.2434 (3)	0.0710 (8)
H19A	0.2798	0.5262	0.1987	0.106*
H19B	0.1907	0.6153	0.2162	0.106*
H19C	0.2986	0.6411	0.3286	0.106*
C20	0.7308 (2)	1.3743 (2)	0.41426 (19)	0.0440 (5)
C21	0.8369 (2)	1.3621 (2)	0.4758 (2)	0.0566 (6)
H21A	0.8599	1.2852	0.4427	0.068*
C22	0.9085 (3)	1.4675 (3)	0.5882 (3)	0.0679 (8)
H22A	0.9807	1.4613	0.6312	0.081*
C23	0.8745 (3)	1.5813 (3)	0.6375 (2)	0.0728 (8)
H23A	0.9235	1.6504	0.7138	0.087*
C24	0.7691 (3)	1.5944 (2)	0.5756 (2)	0.0646 (7)
H24A	0.7464	1.6715	0.6087	0.077*
C25	0.6977 (2)	1.4891 (2)	0.4624 (2)	0.0492 (6)
C26	0.5851 (2)	1.4766 (2)	0.3749 (2)	0.0497 (6)
C27	0.4445 (2)	1.3027 (2)	0.1728 (2)	0.0482 (6)
H27A	0.3760	1.3217	0.2018	0.058*
H27B	0.4277	1.2082	0.1272	0.058*
C28	0.4528 (2)	1.3576 (2)	0.0890 (2)	0.0518 (6)
H28A	0.4637	1.4514	0.1323	0.062*
H28B	0.5237	1.3433	0.0629	0.062*
C29	0.3371 (2)	1.3596 (2)	−0.0916 (2)	0.0552 (6)
H29A	0.3996	1.4300	−0.0749	0.066*
C30	0.2200 (2)	1.2987 (2)	−0.1972 (2)	0.0526 (6)
C31	0.2189 (3)	1.2780 (3)	−0.3105 (3)	0.0811 (9)
H31A	0.2927	1.2992	−0.3230	0.097*
C32	0.1091 (5)	1.2257 (4)	−0.4065 (3)	0.1077 (13)
H32A	0.1095	1.2120	−0.4827	0.129*
C33	0.0009 (4)	1.1948 (4)	−0.3886 (4)	0.1007 (12)
H33A	−0.0724	1.1579	−0.4533	0.121*
C34	−0.0008 (3)	1.2176 (3)	−0.2758 (3)	0.0790 (9)
H34A	−0.0752	1.1992	−0.2633	0.095*
C35	0.1079 (2)	1.2677 (2)	−0.1814 (2)	0.0554 (6)

	U11	U22	U33	U12	U13	U23
O1	0.0714 (11)	0.0304 (8)	0.0645 (10)	0.0073 (7)	0.0418 (9)	0.0170 (7)
O2	0.0791 (13)	0.0448 (11)	0.0760 (12)	0.0301 (9)	0.0223 (10)	0.0201 (9)
O3	0.0627 (12)	0.0906 (14)	0.0746 (12)	0.0092 (10)	0.0367 (10)	0.0397 (11)
N1	0.0433 (10)	0.0308 (9)	0.0472 (10)	0.0084 (7)	0.0125 (8)	0.0147 (8)
N2	0.0487 (11)	0.0499 (11)	0.0488 (10)	0.0077 (8)	0.0154 (9)	0.0255 (9)
N3	0.0664 (14)	0.0418 (11)	0.0643 (12)	0.0082 (9)	0.0374 (11)	0.0220 (9)
N4	0.0567 (12)	0.0400 (11)	0.0742 (13)	0.0135 (9)	0.0381 (11)	0.0281 (10)
C1	0.0464 (13)	0.0336 (12)	0.0499 (12)	0.0046 (9)	0.0183 (10)	0.0197 (10)
C2	0.0537 (14)	0.0333 (12)	0.0498 (12)	0.0064 (10)	0.0215 (11)	0.0150 (10)
C3	0.0421 (12)	0.0404 (12)	0.0481 (12)	0.0070 (9)	0.0154 (10)	0.0212 (10)
C4	0.0391 (12)	0.0396 (12)	0.0514 (12)	0.0053 (9)	0.0126 (10)	0.0240 (10)
C5	0.0444 (12)	0.0312 (11)	0.0534 (13)	0.0080 (9)	0.0160 (10)	0.0189 (10)
C6	0.0406 (12)	0.0339 (12)	0.0462 (12)	0.0068 (9)	0.0131 (10)	0.0188 (9)
C7	0.0417 (12)	0.0310 (11)	0.0478 (12)	0.0101 (9)	0.0164 (10)	0.0174 (9)
C8	0.0416 (12)	0.0332 (12)	0.0476 (12)	0.0088 (9)	0.0153 (10)	0.0189 (9)
C9	0.0490 (13)	0.0335 (12)	0.0476 (12)	0.0126 (9)	0.0182 (10)	0.0151 (9)
C10	0.0450 (13)	0.0414 (13)	0.0514 (12)	0.0144 (9)	0.0212 (10)	0.0226 (10)
C11	0.0429 (12)	0.0383 (12)	0.0551 (13)	0.0113 (9)	0.0207 (10)	0.0242 (10)
C12	0.0543 (14)	0.0306 (12)	0.0574 (13)	0.0099 (9)	0.0264 (11)	0.0180 (10)
C13	0.0467 (13)	0.0343 (12)	0.0500 (12)	0.0108 (9)	0.0225 (10)	0.0190 (9)
C14	0.0681 (17)	0.0454 (14)	0.0726 (16)	0.0115 (12)	0.0338 (14)	0.0323 (12)
C15	0.0718 (17)	0.0482 (15)	0.0566 (14)	0.0065 (12)	0.0287 (13)	0.0185 (11)
C16	0.090 (2)	0.0556 (17)	0.0761 (18)	0.0213 (14)	0.0462 (16)	0.0256 (14)
C17	0.0671 (17)	0.0506 (15)	0.0685 (16)	0.0173 (12)	0.0378 (14)	0.0272 (12)
C18	0.0567 (15)	0.0409 (14)	0.0734 (16)	0.0100 (11)	0.0284 (13)	0.0289 (12)
C19	0.0705 (18)	0.0525 (16)	0.103 (2)	0.0137 (13)	0.0413 (17)	0.0444 (15)
C20	0.0461 (13)	0.0355 (12)	0.0484 (12)	0.0045 (9)	0.0173 (10)	0.0203 (10)
C21	0.0550 (15)	0.0514 (15)	0.0626 (15)	0.0112 (11)	0.0156 (12)	0.0305 (12)
C22	0.0561 (16)	0.0651 (19)	0.0697 (17)	0.0000 (13)	0.0007 (13)	0.0373 (15)
C23	0.082 (2)	0.0507 (17)	0.0541 (15)	−0.0072 (14)	−0.0010 (15)	0.0191 (13)
C24	0.0790 (19)	0.0370 (14)	0.0550 (14)	0.0029 (12)	0.0096 (14)	0.0141 (11)
C25	0.0537 (14)	0.0350 (12)	0.0501 (13)	0.0052 (10)	0.0144 (11)	0.0173 (10)
C26	0.0579 (15)	0.0345 (13)	0.0537 (13)	0.0133 (10)	0.0216 (12)	0.0179 (10)
C27	0.0440 (13)	0.0391 (12)	0.0564 (13)	0.0067 (9)	0.0149 (11)	0.0218 (10)
C28	0.0499 (14)	0.0466 (13)	0.0555 (13)	0.0077 (10)	0.0193 (11)	0.0234 (11)
C29	0.0521 (14)	0.0588 (15)	0.0633 (15)	0.0076 (11)	0.0234 (12)	0.0377 (12)
C30	0.0605 (15)	0.0501 (14)	0.0597 (14)	0.0229 (11)	0.0288 (12)	0.0310 (12)
C31	0.096 (2)	0.105 (3)	0.0682 (19)	0.0437 (19)	0.0405 (18)	0.0533 (18)
C32	0.139 (4)	0.131 (3)	0.065 (2)	0.055 (3)	0.026 (2)	0.057 (2)
C33	0.099 (3)	0.100 (3)	0.095 (3)	0.023 (2)	−0.004 (2)	0.060 (2)
C34	0.0605 (18)	0.074 (2)	0.105 (2)	0.0163 (14)	0.0102 (17)	0.0549 (18)
C35	0.0571 (16)	0.0462 (14)	0.0669 (16)	0.0177 (11)	0.0229 (13)	0.0291 (12)

O1—C13	1.382 (3)	C15—H15B	0.97
O1—C1	1.384 (2)	C16—H16A	0.96
O2—C26	1.229 (3)	C16—H16B	0.96
O3—C35	1.371 (3)	C16—H16C	0.96
O3—H3A	0.82	C17—H17A	0.96
N1—C26	1.362 (3)	C17—H17B	0.96
N1—C27	1.439 (3)	C17—H17C	0.96
N1—C7	1.491 (3)	C18—C19	1.509 (3)
N2—C28	1.461 (3)	C18—H18A	0.97
N2—C29	1.472 (3)	C18—H18B	0.97
N3—C3	1.372 (3)	C19—H19A	0.96
N3—C15	1.450 (3)	C19—H19B	0.96
N3—H3B	0.86	C19—H19C	0.96
N4—C11	1.385 (3)	C20—C21	1.375 (3)
N4—C18	1.438 (3)	C20—C25	1.379 (3)
N4—H4A	0.86	C21—C22	1.383 (4)
C1—C2	1.375 (3)	C21—H21A	0.93
C1—C6	1.380 (3)	C22—C23	1.376 (4)
C2—C3	1.390 (3)	C22—H22A	0.93
C2—H2B	0.93	C23—C24	1.376 (4)
C3—C4	1.421 (3)	C23—H23A	0.93
C4—C5	1.369 (3)	C24—C25	1.387 (3)
C4—C14	1.506 (3)	C24—H24A	0.93
C5—C6	1.401 (3)	C25—C26	1.466 (3)
C5—H5A	0.93	C27—C28	1.509 (3)
C6—C7	1.512 (3)	C27—H27A	0.97
C7—C8	1.514 (3)	C27—H27B	0.97
C7—C20	1.522 (3)	C28—H28A	0.97
C8—C13	1.379 (3)	C28—H28B	0.97
C8—C9	1.393 (3)	C29—C30	1.498 (3)
C9—C10	1.378 (3)	C29—H29A	0.93
C9—H9A	0.93	C30—C31	1.376 (4)
C10—C11	1.417 (3)	C30—C35	1.390 (3)
C10—C17	1.496 (3)	C31—C32	1.390 (5)
C11—C12	1.377 (3)	C31—H31A	0.93
C12—C13	1.387 (3)	C32—C33	1.360 (5)
C12—H12A	0.93	C32—H32A	0.93
C14—H14A	0.96	C33—C34	1.372 (5)
C14—H14B	0.96	C33—H33A	0.93
C14—H14C	0.96	C34—C35	1.374 (4)
C15—C16	1.501 (4)	C34—H34A	0.93
C15—H15A	0.97
C13—O1—C1	118.30 (16)	C10—C17—H17A	109.5
C35—O3—H3A	109.5	C10—C17—H17B	109.5
C26—N1—C27	123.37 (19)	H17A—C17—H17B	109.5
C26—N1—C7	113.76 (17)	C10—C17—H17C	109.5
C27—N1—C7	122.35 (16)	H17A—C17—H17C	109.5
C28—N2—C29	112.26 (18)	H17B—C17—H17C	109.5
C3—N3—C15	122.76 (19)	N4—C18—C19	110.8 (2)
C3—N3—H3B	118.6	N4—C18—H18A	109.5
C15—N3—H3B	118.6	C19—C18—H18A	109.5
C11—N4—C18	122.31 (19)	N4—C18—H18B	109.5
C11—N4—H4A	118.8	C19—C18—H18B	109.5
C18—N4—H4A	118.8	H18A—C18—H18B	108.1
C2—C1—C6	122.20 (19)	C18—C19—H19A	109.5
C2—C1—O1	114.70 (18)	C18—C19—H19B	109.5
C6—C1—O1	123.09 (19)	H19A—C19—H19B	109.5
C1—C2—C3	121.2 (2)	C18—C19—H19C	109.5
C1—C2—H2B	119.4	H19A—C19—H19C	109.5
C3—C2—H2B	119.4	H19B—C19—H19C	109.5
N3—C3—C2	121.2 (2)	C21—C20—C25	120.9 (2)
N3—C3—C4	120.58 (19)	C21—C20—C7	128.6 (2)
C2—C3—C4	118.2 (2)	C25—C20—C7	110.5 (2)
C5—C4—C3	118.36 (19)	C20—C21—C22	118.2 (3)
C5—C4—C14	121.3 (2)	C20—C21—H21A	120.9
C3—C4—C14	120.3 (2)	C22—C21—H21A	120.9
C4—C5—C6	124.1 (2)	C23—C22—C21	121.1 (3)
C4—C5—H5A	118.0	C23—C22—H22A	119.5
C6—C5—H5A	118.0	C21—C22—H22A	119.5
C1—C6—C5	116.0 (2)	C22—C23—C24	120.9 (2)
C1—C6—C7	122.45 (18)	C22—C23—H23A	119.5
C5—C6—C7	121.51 (18)	C24—C23—H23A	119.5
N1—C7—C6	111.72 (17)	C23—C24—C25	118.1 (3)
N1—C7—C8	109.84 (17)	C23—C24—H24A	121.0
C6—C7—C8	110.45 (17)	C25—C24—H24A	121.0
N1—C7—C20	99.86 (16)	C20—C25—C24	120.8 (2)
C6—C7—C20	111.95 (17)	C20—C25—C26	109.02 (19)
C8—C7—C20	112.63 (17)	C24—C25—C26	130.1 (2)
C13—C8—C9	116.30 (19)	O2—C26—N1	124.8 (2)
C13—C8—C7	122.44 (19)	O2—C26—C25	128.6 (2)
C9—C8—C7	121.24 (18)	N1—C26—C25	106.6 (2)
C10—C9—C8	123.8 (2)	N1—C27—C28	113.04 (18)
C10—C9—H9A	118.1	N1—C27—H27A	109.0
C8—C9—H9A	118.1	C28—C27—H27A	109.0
C9—C10—C11	118.1 (2)	N1—C27—H27B	109.0
C9—C10—C17	121.2 (2)	C28—C27—H27B	109.0
C11—C10—C17	120.7 (2)	H27A—C27—H27B	107.8
C12—C11—N4	122.2 (2)	N2—C28—C27	110.51 (18)
C12—C11—C10	119.00 (19)	N2—C28—H28A	109.5
N4—C11—C10	118.74 (19)	C27—C28—H28A	109.5
C11—C12—C13	120.7 (2)	N2—C28—H28B	109.5
C11—C12—H12A	119.7	C27—C28—H28B	109.5
C13—C12—H12A	119.7	H28A—C28—H28B	108.1
C8—C13—O1	123.17 (18)	N2—C29—C30	111.97 (19)
C8—C13—C12	122.1 (2)	N2—C29—H29A	124.0
O1—C13—C12	114.72 (18)	C30—C29—H29A	124.0
C4—C14—H14A	109.5	C31—C30—C35	117.9 (3)
C4—C14—H14B	109.5	C31—C30—C29	121.6 (2)
H14A—C14—H14B	109.5	C35—C30—C29	120.4 (2)
C4—C14—H14C	109.5	C30—C31—C32	120.9 (3)
H14A—C14—H14C	109.5	C30—C31—H31A	119.5
H14B—C14—H14C	109.5	C32—C31—H31A	119.5
N3—C15—C16	111.8 (2)	C33—C32—C31	119.8 (3)
N3—C15—H15A	109.2	C33—C32—H32A	120.1
C16—C15—H15A	109.2	C31—C32—H32A	120.1
N3—C15—H15B	109.2	C32—C33—C34	120.5 (3)
C16—C15—H15B	109.2	C32—C33—H33A	119.8
H15A—C15—H15B	107.9	C34—C33—H33A	119.8
C15—C16—H16A	109.5	C33—C34—C35	119.6 (3)
C15—C16—H16B	109.5	C33—C34—H34A	120.2
H16A—C16—H16B	109.5	C35—C34—H34A	120.2
C15—C16—H16C	109.5	O3—C35—C34	118.3 (3)
H16A—C16—H16C	109.5	O3—C35—C30	120.5 (2)
H16B—C16—H16C	109.5	C34—C35—C30	121.2 (3)
C13—O1—C1—C2	177.43 (19)	C9—C8—C13—C12	−0.1 (3)
C13—O1—C1—C6	−2.0 (3)	C7—C8—C13—C12	−178.4 (2)
C6—C1—C2—C3	0.3 (4)	C1—O1—C13—C8	−1.0 (3)
O1—C1—C2—C3	−179.1 (2)	C1—O1—C13—C12	179.64 (19)
C15—N3—C3—C2	1.6 (4)	C11—C12—C13—C8	0.0 (4)
C15—N3—C3—C4	−179.2 (2)	C11—C12—C13—O1	179.4 (2)
C1—C2—C3—N3	177.4 (2)	C3—N3—C15—C16	−175.0 (2)
C1—C2—C3—C4	−1.9 (3)	C11—N4—C18—C19	178.4 (2)
N3—C3—C4—C5	−177.3 (2)	N1—C7—C20—C21	−175.0 (2)
C2—C3—C4—C5	1.9 (3)	C6—C7—C20—C21	−56.6 (3)
N3—C3—C4—C14	1.7 (3)	C8—C7—C20—C21	68.6 (3)
C2—C3—C4—C14	−179.1 (2)	N1—C7—C20—C25	4.0 (2)
C3—C4—C5—C6	−0.5 (3)	C6—C7—C20—C25	122.4 (2)
C14—C4—C5—C6	−179.5 (2)	C8—C7—C20—C25	−112.4 (2)
C2—C1—C6—C5	1.1 (3)	C25—C20—C21—C22	1.1 (3)
O1—C1—C6—C5	−179.5 (2)	C7—C20—C21—C22	180.0 (2)
C2—C1—C6—C7	−175.8 (2)	C20—C21—C22—C23	0.2 (4)
O1—C1—C6—C7	3.6 (3)	C21—C22—C23—C24	−1.0 (4)
C4—C5—C6—C1	−1.0 (3)	C22—C23—C24—C25	0.4 (4)
C4—C5—C6—C7	175.9 (2)	C21—C20—C25—C24	−1.6 (3)
C26—N1—C7—C6	−123.32 (19)	C7—C20—C25—C24	179.3 (2)
C27—N1—C7—C6	64.6 (2)	C21—C20—C25—C26	176.9 (2)
C26—N1—C7—C8	113.8 (2)	C7—C20—C25—C26	−2.2 (3)
C27—N1—C7—C8	−58.3 (2)	C23—C24—C25—C20	0.8 (4)
C26—N1—C7—C20	−4.8 (2)	C23—C24—C25—C26	−177.4 (2)
C27—N1—C7—C20	−176.83 (18)	C27—N1—C26—O2	−5.4 (4)
C1—C6—C7—N1	−124.7 (2)	C7—N1—C26—O2	−177.4 (2)
C5—C6—C7—N1	58.6 (3)	C27—N1—C26—C25	175.75 (19)
C1—C6—C7—C8	−2.1 (3)	C7—N1—C26—C25	3.8 (2)
C5—C6—C7—C8	−178.85 (18)	C20—C25—C26—O2	−179.7 (2)
C1—C6—C7—C20	124.3 (2)	C24—C25—C26—O2	−1.4 (4)
C5—C6—C7—C20	−52.5 (3)	C20—C25—C26—N1	−0.9 (3)
N1—C7—C8—C13	123.0 (2)	C24—C25—C26—N1	177.4 (2)
C6—C7—C8—C13	−0.7 (3)	C26—N1—C27—C28	77.5 (3)
C20—C7—C8—C13	−126.7 (2)	C7—N1—C27—C28	−111.2 (2)
N1—C7—C8—C9	−55.2 (3)	C29—N2—C28—C27	170.9 (2)
C6—C7—C8—C9	−178.86 (19)	N1—C27—C28—N2	176.43 (18)
C20—C7—C8—C9	55.1 (3)	C28—N2—C29—C30	−177.25 (19)
C13—C8—C9—C10	0.1 (3)	N2—C29—C30—C31	−139.0 (3)
C7—C8—C9—C10	178.4 (2)	N2—C29—C30—C35	44.5 (3)
C8—C9—C10—C11	−0.1 (3)	C35—C30—C31—C32	−1.0 (4)
C8—C9—C10—C17	−179.0 (2)	C29—C30—C31—C32	−177.6 (3)
C18—N4—C11—C12	10.5 (4)	C30—C31—C32—C33	0.2 (6)
C18—N4—C11—C10	−170.9 (2)	C31—C32—C33—C34	1.5 (6)
C9—C10—C11—C12	0.0 (3)	C32—C33—C34—C35	−2.3 (5)
C17—C10—C11—C12	178.9 (2)	C33—C34—C35—O3	−179.7 (3)
C9—C10—C11—N4	−178.7 (2)	C33—C34—C35—C30	1.4 (4)
C17—C10—C11—N4	0.2 (3)	C31—C30—C35—O3	−178.7 (2)
N4—C11—C12—C13	178.7 (2)	C29—C30—C35—O3	−2.0 (4)
C10—C11—C12—C13	0.1 (3)	C31—C30—C35—C34	0.2 (4)
C9—C8—C13—O1	−179.5 (2)	C29—C30—C35—C34	176.9 (2)
C7—C8—C13—O1	2.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N2	0.82	2.01	2.685 (3)	139
N3—H3B···O3i	0.86	2.32	3.144 (1)	160
C9—H9A···O2ii	0.93	2.59	3.468 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯N2	0.82	2.01	2.685 (3)	139
N3—H3B⋯O3i	0.86	2.32	3.144 (1)	160
C9—H9A⋯O2ii	0.93	2.59	3.468 (3)	157

Symmetry codes: (i) ; (ii) .