Two rhodamine 6G derivative compounds: a structural and fluorescence single-crystal study

The synthesis, characterization, structural analysis and fluorescence properties of two rhodamine 6G derivatives are described, namely a propargylamine derivative, 3′,6′-bis(ethylamino)-2′,7′-dimethyl-2-(methylcyanide)spiro[iso­indole-1,9′-xanthen]-3(2H)-one (I), and a γ-aminobutyric acid (GABA) derivative, 3′,6′-bis(ethylamino)-2′,7′-dimethyl-3-oxospiro[isoindole-1,9′-xanthen]-2(3H)-yl)butyricacid (II). Both structures are compared with four similar ones from the Cambridge Structural Database (CSD), and the interactions involved in the stabilization are analyzed using the atoms in molecules (AIM) theory. Finally, a single-crystal in-situ reaction study is presented, carried out by fluorescence methods, which enabled the `opening' of the spirolactam ring in the solid phase.

Computing details

For both compounds, data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009).

(I)

Crystal data

C28H26N4O2	Z = 2
Mr = 450.53	F(000) = 476
Triclinic, P1	Dx = 1.230 Mg m^−3
a = 8.9389 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.7292 (7) Å	Cell parameters from 8908 reflections
c = 16.0650 (8) Å	θ = 3.8–28.9°
α = 89.067 (5)°	µ = 0.08 mm^−1
β = 78.856 (4)°	T = 170 K
γ = 62.927 (6)°	Blocks, orange
V = 1216.48 (14) Å^3	0.50 × 0.40 × 0.35 mm

Data collection

Oxford Diffraction Gemini CCD S Ultra diffractometer	3610 reflections with I > 2σ(I)
ω scans, thick slices	Rint = 0.042
Absorption correction: multi-scan CrysAlisPro, Oxford Diffraction (2009)	θmax = 29.3°, θmin = 3.7°
Tmin = 0.94, Tmax = 0.98	h = −12→12
18456 measured reflections	k = −13→13
5811 independent reflections	l = −21→20

Refinement

Refinement on F^2	6 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.065	H-atom parameters constrained
wR(F^2) = 0.203	w = 1/[σ^2(Fo^2) + (0.1002P)^2 + 0.6102P] where P = (Fo^2 + 2Fc^2)/3
S = 0.91	(Δ/σ)max < 0.001
5811 reflections	Δρmax = 0.37 e Å^−3
331 parameters	Δρmin = −0.26 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.0995 (2)	0.79651 (18)	0.16643 (9)	0.0470 (4)
O2	−0.3963 (2)	0.8173 (2)	0.51977 (10)	0.0595 (5)
N1	−0.1435 (3)	1.3471 (3)	0.17732 (14)	0.0619 (6)
N2	0.4244 (3)	0.2485 (2)	0.15632 (14)	0.0632 (6)
N3	−0.1976 (2)	0.8170 (2)	0.40511 (11)	0.0399 (4)
C1	−0.0277 (3)	0.9361 (2)	0.20754 (13)	0.0386 (5)
C2	−0.0219 (3)	1.0666 (3)	0.17407 (14)	0.0453 (5)
H2	0.0637	1.0552	0.1273	0.054*
C3	−0.1425 (3)	1.2134 (3)	0.20977 (15)	0.0460 (5)
C4	−0.2694 (3)	1.2286 (3)	0.28129 (15)	0.0477 (6)
C5	−0.2718 (3)	1.0964 (3)	0.31197 (15)	0.0453 (5)
H5	−0.3569	1.1070	0.3588	0.054*
C6	−0.1528 (3)	0.9472 (2)	0.27641 (13)	0.0371 (5)
C7	−0.1647 (3)	0.8065 (2)	0.31066 (12)	0.0358 (5)
C8	−0.0034 (3)	0.6606 (2)	0.27171 (13)	0.0371 (5)
C9	0.0301 (3)	0.5166 (2)	0.30231 (13)	0.0427 (5)
H9	−0.0471	0.5125	0.3491	0.051*
C10	0.1708 (3)	0.3802 (3)	0.26709 (14)	0.0446 (5)
C11	0.2867 (3)	0.3866 (3)	0.19534 (15)	0.0465 (5)
C12	0.2571 (3)	0.5287 (3)	0.16470 (14)	0.0455 (5)
H12	0.3341	0.5340	0.1183	0.055*
C13	0.1137 (3)	0.6630 (2)	0.20261 (13)	0.0385 (5)
C14	−0.4013 (4)	1.3856 (3)	0.3232 (2)	0.0714 (8)
H14A	−0.3445	1.4383	0.3427	0.107*
H14B	−0.4768	1.3737	0.3707	0.107*
H14C	−0.4666	1.4450	0.2829	0.107*
C15	0.1992 (4)	0.2289 (3)	0.30289 (17)	0.0620 (7)
H15A	0.2096	0.1577	0.2588	0.093*
H15B	0.1035	0.2454	0.3480	0.093*
H15C	0.3025	0.1868	0.3248	0.093*
C16	−0.0103 (4)	1.3426 (3)	0.10757 (16)	0.0665 (8)
H16A	0.0992	1.2586	0.1136	0.080*
H16B	−0.0028	1.4386	0.1114	0.080*
C17	−0.0413 (6)	1.3205 (5)	0.0217 (2)	0.0959 (12)
H17A	0.0511	1.3173	−0.0215	0.144*
H17B	−0.1476	1.4051	0.0145	0.144*
H17C	−0.0475	1.2250	0.0171	0.144*
C18A	0.5389 (8)	0.2514 (7)	0.0794 (4)	0.066 (2)	0.681 (8)
H18A	0.5985	0.3078	0.0924	0.079*	0.681 (8)
H18B	0.4719	0.3055	0.0377	0.079*	0.681 (8)
C19A	0.6677 (6)	0.0913 (5)	0.0424 (3)	0.0851 (19)	0.681 (8)
H19A	0.7485	0.0970	−0.0047	0.128*	0.681 (8)
H19B	0.6098	0.0396	0.0231	0.128*	0.681 (8)
H19C	0.7274	0.0346	0.0852	0.128*	0.681 (8)
C18B	0.5761 (13)	0.230 (2)	0.0949 (6)	0.081 (6)	0.319 (8)
H18C	0.6757	0.1339	0.1000	0.097*	0.319 (8)
H18D	0.6009	0.3158	0.1017	0.097*	0.319 (8)
C19B	0.5255 (16)	0.2275 (16)	0.0117 (8)	0.099 (5)	0.319 (8)
H19D	0.6127	0.2276	−0.0338	0.149*	0.319 (8)
H19E	0.4184	0.3175	0.0113	0.149*	0.319 (8)
H19F	0.5130	0.1359	0.0040	0.149*	0.319 (8)
C20	−0.3261 (3)	0.8009 (2)	0.29691 (13)	0.0381 (5)
C21	−0.3753 (3)	0.7932 (3)	0.22187 (16)	0.0510 (6)
H21	−0.3070	0.7904	0.1696	0.061*
C22	−0.5310 (4)	0.7896 (3)	0.22671 (19)	0.0617 (7)
H22	−0.5673	0.7849	0.1768	0.074*
C23	−0.6321 (3)	0.7928 (3)	0.3041 (2)	0.0621 (7)
H23	−0.7353	0.7902	0.3056	0.075*
C24	−0.5828 (3)	0.7998 (3)	0.37835 (18)	0.0539 (6)
H24	−0.6504	0.8011	0.4305	0.065*
C25	−0.4286 (3)	0.8048 (2)	0.37392 (14)	0.0413 (5)
C26	−0.3459 (3)	0.8138 (2)	0.44288 (14)	0.0415 (5)
C1X	−0.0887 (3)	0.8400 (3)	0.45357 (14)	0.0480 (6)
H1XA	−0.0457	0.9067	0.4240	0.058*
H1XB	−0.1577	0.8932	0.5085	0.058*
C2X	0.0554 (3)	0.6988 (3)	0.46708 (16)	0.0525 (6)
N2X	0.1730 (4)	0.5808 (4)	0.47839 (19)	0.1011 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0478 (9)	0.0446 (9)	0.0420 (9)	−0.0220 (8)	0.0068 (7)	0.0007 (7)
O2	0.0584 (11)	0.0637 (11)	0.0426 (10)	−0.0236 (9)	0.0073 (8)	0.0089 (8)
N1	0.0800 (16)	0.0546 (13)	0.0644 (14)	−0.0427 (12)	−0.0150 (12)	0.0201 (10)
N2	0.0433 (11)	0.0529 (13)	0.0725 (15)	−0.0092 (10)	0.0025 (10)	−0.0145 (11)
N3	0.0392 (9)	0.0429 (10)	0.0339 (9)	−0.0178 (8)	−0.0024 (7)	0.0029 (7)
C1	0.0379 (11)	0.0423 (12)	0.0355 (11)	−0.0196 (10)	−0.0041 (9)	−0.0003 (9)
C2	0.0504 (13)	0.0531 (14)	0.0386 (12)	−0.0315 (12)	−0.0032 (10)	0.0070 (10)
C3	0.0538 (14)	0.0451 (13)	0.0467 (13)	−0.0277 (11)	−0.0144 (11)	0.0096 (10)
C4	0.0503 (13)	0.0413 (12)	0.0503 (13)	−0.0206 (11)	−0.0091 (11)	0.0057 (10)
C5	0.0423 (12)	0.0430 (12)	0.0460 (13)	−0.0184 (10)	−0.0022 (10)	0.0039 (10)
C6	0.0375 (11)	0.0387 (11)	0.0352 (11)	−0.0183 (9)	−0.0056 (9)	0.0035 (8)
C7	0.0353 (10)	0.0389 (11)	0.0313 (10)	−0.0176 (9)	−0.0017 (8)	0.0030 (8)
C8	0.0351 (10)	0.0393 (11)	0.0335 (11)	−0.0151 (9)	−0.0044 (8)	−0.0006 (8)
C9	0.0448 (12)	0.0420 (12)	0.0362 (11)	−0.0177 (10)	−0.0029 (9)	0.0011 (9)
C10	0.0477 (13)	0.0400 (12)	0.0404 (12)	−0.0143 (10)	−0.0121 (10)	−0.0001 (9)
C11	0.0362 (11)	0.0461 (13)	0.0480 (13)	−0.0108 (10)	−0.0086 (10)	−0.0086 (10)
C12	0.0378 (11)	0.0502 (13)	0.0427 (12)	−0.0185 (10)	0.0007 (9)	−0.0054 (10)
C13	0.0372 (11)	0.0416 (11)	0.0367 (11)	−0.0194 (9)	−0.0043 (9)	−0.0004 (9)
C14	0.0762 (19)	0.0412 (14)	0.080 (2)	−0.0192 (14)	0.0006 (15)	0.0017 (13)
C15	0.0727 (18)	0.0436 (14)	0.0565 (16)	−0.0149 (13)	−0.0152 (13)	0.0067 (11)
C16	0.090 (2)	0.0698 (18)	0.0634 (17)	−0.0553 (17)	−0.0222 (15)	0.0266 (14)
C17	0.134 (3)	0.119 (3)	0.065 (2)	−0.080 (3)	−0.032 (2)	0.034 (2)
C18A	0.038 (3)	0.060 (3)	0.075 (4)	−0.007 (3)	0.007 (3)	−0.023 (3)
C19A	0.062 (3)	0.069 (3)	0.085 (3)	−0.006 (2)	0.011 (2)	−0.030 (2)
C18B	0.032 (6)	0.091 (11)	0.106 (12)	−0.017 (6)	−0.013 (6)	−0.013 (8)
C19B	0.091 (9)	0.111 (10)	0.072 (8)	−0.033 (8)	0.001 (6)	−0.024 (7)
C20	0.0354 (11)	0.0317 (10)	0.0449 (12)	−0.0142 (9)	−0.0065 (9)	0.0034 (8)
C21	0.0520 (14)	0.0505 (14)	0.0520 (14)	−0.0240 (12)	−0.0133 (11)	0.0064 (11)
C22	0.0602 (16)	0.0557 (15)	0.0757 (19)	−0.0256 (13)	−0.0310 (15)	0.0030 (13)
C23	0.0432 (14)	0.0531 (15)	0.093 (2)	−0.0246 (12)	−0.0139 (14)	0.0017 (14)
C24	0.0414 (13)	0.0435 (13)	0.0719 (17)	−0.0204 (11)	0.0010 (12)	0.0016 (11)
C25	0.0340 (11)	0.0303 (10)	0.0526 (13)	−0.0121 (9)	−0.0006 (9)	0.0034 (9)
C26	0.0397 (11)	0.0328 (11)	0.0415 (12)	−0.0127 (9)	0.0043 (9)	0.0041 (9)
C1X	0.0546 (14)	0.0529 (14)	0.0399 (12)	−0.0279 (12)	−0.0090 (10)	0.0023 (10)
C2X	0.0416 (13)	0.0640 (16)	0.0475 (14)	−0.0204 (12)	−0.0098 (11)	0.0102 (11)
N2X	0.083 (2)	0.126 (3)	0.086 (2)	−0.044 (2)	−0.0109 (16)	0.0209 (19)

Geometric parameters (Å, º)

O1—C13	1.376 (3)	C15—H15B	0.9600
O1—C1	1.381 (3)	C15—H15C	0.9600
O2—C26	1.226 (3)	C16—C17	1.495 (4)
N1—C3	1.391 (3)	C16—H16A	0.9700
N1—C16	1.453 (3)	C16—H16B	0.9700
N2—C11	1.392 (3)	C17—H17A	0.9600
N2—C18B	1.453 (3)	C17—H17B	0.9600
N2—C18A	1.454 (3)	C17—H17C	0.9600
N3—C26	1.361 (3)	C18A—C19A	1.496 (4)
N3—C1X	1.450 (3)	C18A—H18A	0.9700
N3—C7	1.485 (3)	C18A—H18B	0.9700
C1—C6	1.379 (3)	C19A—H19A	0.9600
C1—C2	1.389 (3)	C19A—H19B	0.9600
C2—C3	1.385 (3)	C19A—H19C	0.9600
C2—H2	0.9300	C18B—C19B	1.495 (4)
C3—C4	1.406 (3)	C18B—H18C	0.9700
C4—C5	1.378 (3)	C18B—H18D	0.9700
C4—C14	1.505 (3)	C19B—H19D	0.9600
C5—C6	1.397 (3)	C19B—H19E	0.9600
C5—H5	0.9300	C19B—H19F	0.9600
C6—C7	1.508 (3)	C20—C21	1.375 (3)
C7—C8	1.518 (3)	C20—C25	1.379 (3)
C7—C20	1.527 (3)	C21—C22	1.395 (3)
C8—C13	1.379 (3)	C21—H21	0.9300
C8—C9	1.395 (3)	C22—C23	1.381 (4)
C9—C10	1.376 (3)	C22—H22	0.9300
C9—H9	0.9300	C23—C24	1.361 (4)
C10—C11	1.414 (3)	C23—H23	0.9300
C10—C15	1.500 (3)	C24—C25	1.390 (3)
C11—C12	1.386 (3)	C24—H24	0.9300
C12—C13	1.386 (3)	C25—C26	1.470 (3)
C12—H12	0.9300	C1X—C2X	1.443 (3)
C14—H14A	0.9600	C1X—H1XA	0.9700
C14—H14B	0.9600	C1X—H1XB	0.9700
C14—H14C	0.9600	C2X—N2X	1.193 (4)
C15—H15A	0.9600
C13—O1—C1	117.82 (16)	C17—C16—H16A	108.9
C3—N1—C16	122.3 (2)	N1—C16—H16B	108.9
C11—N2—C18B	127.3 (9)	C17—C16—H16B	108.9
C11—N2—C18A	119.5 (3)	H16A—C16—H16B	107.7
C26—N3—C1X	122.42 (18)	C16—C17—H17A	109.5
C26—N3—C7	114.19 (17)	C16—C17—H17B	109.5
C1X—N3—C7	123.25 (17)	H17A—C17—H17B	109.5
C6—C1—O1	123.16 (19)	C16—C17—H17C	109.5
C6—C1—C2	121.8 (2)	H17A—C17—H17C	109.5
O1—C1—C2	115.04 (18)	H17B—C17—H17C	109.5
C3—C2—C1	120.5 (2)	N2—C18A—C19A	111.4 (4)
C3—C2—H2	119.7	N2—C18A—H18A	109.3
C1—C2—H2	119.7	C19A—C18A—H18A	109.3
C2—C3—N1	122.4 (2)	N2—C18A—H18B	109.3
C2—C3—C4	119.1 (2)	C19A—C18A—H18B	109.3
N1—C3—C4	118.5 (2)	H18A—C18A—H18B	108.0
C5—C4—C3	118.6 (2)	C18A—C19A—H19A	109.5
C5—C4—C14	120.4 (2)	C18A—C19A—H19B	109.5
C3—C4—C14	121.0 (2)	H19A—C19A—H19B	109.5
C4—C5—C6	123.4 (2)	C18A—C19A—H19C	109.5
C4—C5—H5	118.3	H19A—C19A—H19C	109.5
C6—C5—H5	118.3	H19B—C19A—H19C	109.5
C1—C6—C5	116.64 (19)	N2—C18B—C19B	102.6 (8)
C1—C6—C7	122.10 (18)	N2—C18B—H18C	111.2
C5—C6—C7	121.24 (18)	C19B—C18B—H18C	111.2
N3—C7—C6	111.22 (16)	N2—C18B—H18D	111.2
N3—C7—C8	111.86 (16)	C19B—C18B—H18D	111.2
C6—C7—C8	110.05 (16)	H18C—C18B—H18D	109.2
N3—C7—C20	99.84 (15)	C18B—C19B—H19D	109.5
C6—C7—C20	112.06 (17)	C18B—C19B—H19E	109.5
C8—C7—C20	111.51 (16)	H19D—C19B—H19E	109.5
C13—C8—C9	116.87 (19)	C18B—C19B—H19F	109.5
C13—C8—C7	121.68 (19)	H19D—C19B—H19F	109.5
C9—C8—C7	121.41 (18)	H19E—C19B—H19F	109.5
C10—C9—C8	123.6 (2)	C21—C20—C25	120.5 (2)
C10—C9—H9	118.2	C21—C20—C7	129.0 (2)
C8—C9—H9	118.2	C25—C20—C7	110.49 (18)
C9—C10—C11	118.0 (2)	C20—C21—C22	117.7 (2)
C9—C10—C15	121.0 (2)	C20—C21—H21	121.1
C11—C10—C15	121.0 (2)	C22—C21—H21	121.1
C12—C11—N2	122.2 (2)	C23—C22—C21	121.3 (2)
C12—C11—C10	119.3 (2)	C23—C22—H22	119.4
N2—C11—C10	118.5 (2)	C21—C22—H22	119.4
C13—C12—C11	120.5 (2)	C24—C23—C22	120.9 (2)
C13—C12—H12	119.7	C24—C23—H23	119.6
C11—C12—H12	119.7	C22—C23—H23	119.6
C8—C13—O1	123.44 (19)	C23—C24—C25	118.1 (2)
C8—C13—C12	121.7 (2)	C23—C24—H24	121.0
O1—C13—C12	114.88 (19)	C25—C24—H24	121.0
C4—C14—H14A	109.5	C20—C25—C24	121.5 (2)
C4—C14—H14B	109.5	C20—C25—C26	108.90 (18)
H14A—C14—H14B	109.5	C24—C25—C26	129.6 (2)
C4—C14—H14C	109.5	O2—C26—N3	125.2 (2)
H14A—C14—H14C	109.5	O2—C26—C25	128.2 (2)
H14B—C14—H14C	109.5	N3—C26—C25	106.56 (18)
C10—C15—H15A	109.5	C2X—C1X—N3	114.2 (2)
C10—C15—H15B	109.5	C2X—C1X—H1XA	108.7
H15A—C15—H15B	109.5	N3—C1X—H1XA	108.7
C10—C15—H15C	109.5	C2X—C1X—H1XB	108.7
H15A—C15—H15C	109.5	N3—C1X—H1XB	108.7
H15B—C15—H15C	109.5	H1XA—C1X—H1XB	107.6
N1—C16—C17	113.4 (3)	N2X—C2X—C1X	179.0 (3)
N1—C16—H16A	108.9
C13—O1—C1—C6	−8.3 (3)	C18A—N2—C11—C10	176.2 (4)
C13—O1—C1—C2	172.20 (18)	C9—C10—C11—C12	1.6 (3)
C6—C1—C2—C3	0.5 (3)	C15—C10—C11—C12	−179.3 (2)
O1—C1—C2—C3	−179.99 (19)	C9—C10—C11—N2	−176.5 (2)
C1—C2—C3—N1	−178.7 (2)	C15—C10—C11—N2	2.5 (3)
C1—C2—C3—C4	1.0 (3)	N2—C11—C12—C13	176.7 (2)
C16—N1—C3—C2	−4.8 (4)	C10—C11—C12—C13	−1.4 (3)
C16—N1—C3—C4	175.4 (2)	C9—C8—C13—O1	−178.85 (18)
C2—C3—C4—C5	−1.7 (3)	C7—C8—C13—O1	3.5 (3)
N1—C3—C4—C5	178.1 (2)	C9—C8—C13—C12	0.6 (3)
C2—C3—C4—C14	178.9 (2)	C7—C8—C13—C12	−177.08 (19)
N1—C3—C4—C14	−1.3 (4)	C1—O1—C13—C8	7.6 (3)
C3—C4—C5—C6	1.0 (4)	C1—O1—C13—C12	−171.84 (18)
C14—C4—C5—C6	−179.7 (2)	C11—C12—C13—C8	0.3 (3)
O1—C1—C6—C5	179.28 (19)	C11—C12—C13—O1	179.77 (18)
C2—C1—C6—C5	−1.2 (3)	C3—N1—C16—C17	84.4 (3)
O1—C1—C6—C7	−2.3 (3)	C11—N2—C18A—C19A	−174.4 (4)
C2—C1—C6—C7	177.22 (19)	C11—N2—C18B—C19B	−92.4 (13)
C4—C5—C6—C1	0.5 (3)	N3—C7—C20—C21	178.9 (2)
C4—C5—C6—C7	−177.9 (2)	C6—C7—C20—C21	61.0 (3)
C26—N3—C7—C6	120.02 (19)	C8—C7—C20—C21	−62.8 (3)
C1X—N3—C7—C6	−55.7 (3)	N3—C7—C20—C25	−1.0 (2)
C26—N3—C7—C8	−116.48 (19)	C6—C7—C20—C25	−118.84 (19)
C1X—N3—C7—C8	67.8 (2)	C8—C7—C20—C25	117.30 (19)
C26—N3—C7—C20	1.6 (2)	C25—C20—C21—C22	0.0 (3)
C1X—N3—C7—C20	−174.13 (18)	C7—C20—C21—C22	−179.9 (2)
C1—C6—C7—N3	136.5 (2)	C20—C21—C22—C23	−0.3 (4)
C5—C6—C7—N3	−45.2 (3)	C21—C22—C23—C24	0.1 (4)
C1—C6—C7—C8	12.0 (3)	C22—C23—C24—C25	0.5 (4)
C5—C6—C7—C8	−169.69 (19)	C21—C20—C25—C24	0.6 (3)
C1—C6—C7—C20	−112.7 (2)	C7—C20—C25—C24	−179.53 (19)
C5—C6—C7—C20	65.6 (3)	C21—C20—C25—C26	−179.66 (19)
N3—C7—C8—C13	−136.67 (19)	C7—C20—C25—C26	0.2 (2)
C6—C7—C8—C13	−12.5 (3)	C23—C24—C25—C20	−0.9 (3)
C20—C7—C8—C13	112.5 (2)	C23—C24—C25—C26	179.5 (2)
N3—C7—C8—C9	45.8 (3)	C1X—N3—C26—O2	−6.0 (3)
C6—C7—C8—C9	169.92 (18)	C7—N3—C26—O2	178.20 (19)
C20—C7—C8—C9	−65.1 (2)	C1X—N3—C26—C25	174.22 (18)
C13—C8—C9—C10	−0.3 (3)	C7—N3—C26—C25	−1.5 (2)
C7—C8—C9—C10	177.3 (2)	C20—C25—C26—O2	−178.9 (2)
C8—C9—C10—C11	−0.8 (3)	C24—C25—C26—O2	0.8 (4)
C8—C9—C10—C15	−179.8 (2)	C20—C25—C26—N3	0.8 (2)
C18B—N2—C11—C12	16.2 (7)	C24—C25—C26—N3	−179.5 (2)
C18A—N2—C11—C12	−1.9 (5)	C26—N3—C1X—C2X	98.0 (2)
C18B—N2—C11—C10	−165.7 (7)	C7—N3—C1X—C2X	−86.7 (3)

(II)

Crystal data

C30H33N3O4	Z = 2
Mr = 499.59	F(000) = 532
Triclinic, P1	Dx = 1.292 Mg m^−3
a = 9.4250 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.6209 (4) Å	Cell parameters from 7543 reflections
c = 12.6080 (5) Å	θ = 3.9–28.1°
α = 88.708 (3)°	µ = 0.09 mm^−1
β = 68.696 (5)°	T = 170 K
γ = 86.313 (4)°	Blocks, orange
V = 1283.89 (11) Å^3	0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Gemini CCD S Ultra diffractometer	3882 reflections with I > 2σ(I)
ω scans, thick slices	Rint = 0.046
Absorption correction: multi-scan CrysAlisPro, Oxford Diffraction (2009)	θmax = 29.2°, θmin = 3.7°
Tmin = 0.97, Tmax = 0.99	h = −12→12
19816 measured reflections	k = −15→15
6120 independent reflections	l = −16→17

Refinement

Refinement on F^2	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.060	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.171	w = 1/[σ^2(Fo^2) + (0.0648P)^2 + 0.3526P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
6120 reflections	Δρmax = 0.31 e Å^−3
350 parameters	Δρmin = −0.29 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.14581 (16)	0.40503 (11)	0.50176 (11)	0.0271 (3)
O2	0.2582 (2)	0.15924 (14)	0.03857 (13)	0.0525 (5)
N1	−0.1936 (2)	0.12244 (17)	0.70654 (16)	0.0369 (5)
H1N	−0.267 (3)	0.085 (2)	0.710 (2)	0.056 (8)*
N2	0.5021 (2)	0.68697 (15)	0.33058 (15)	0.0306 (4)
H2N	0.520 (3)	0.7440 (19)	0.2848 (19)	0.050 (8)*
N3	0.2268 (2)	0.25289 (14)	0.20418 (14)	0.0304 (4)
C1	0.0527 (2)	0.31956 (15)	0.49677 (16)	0.0230 (4)
C2	−0.0225 (2)	0.26623 (16)	0.60005 (16)	0.0248 (4)
H2	−0.0095	0.2899	0.6657	0.030*
C3	−0.1174 (2)	0.17752 (16)	0.60551 (16)	0.0252 (4)
C4	−0.1353 (2)	0.14270 (16)	0.50438 (17)	0.0263 (4)
C5	−0.0607 (2)	0.19941 (16)	0.40494 (16)	0.0265 (4)
H5	−0.0750	0.1774	0.3392	0.032*
C6	0.0359 (2)	0.28873 (16)	0.39702 (16)	0.0239 (4)
C7	0.1221 (2)	0.34277 (16)	0.28328 (16)	0.0254 (4)
C8	0.2133 (2)	0.43961 (15)	0.29875 (16)	0.0229 (4)
C9	0.2997 (2)	0.50529 (16)	0.20553 (16)	0.0247 (4)
H9	0.2927	0.4924	0.1351	0.030*
C10	0.3943 (2)	0.58801 (16)	0.21284 (16)	0.0254 (4)
C11	0.4040 (2)	0.60797 (16)	0.32047 (16)	0.0245 (4)
C12	0.3179 (2)	0.54459 (16)	0.41415 (16)	0.0242 (4)
H12	0.3225	0.5579	0.4852	0.029*
C13	0.2250 (2)	0.46154 (16)	0.40225 (15)	0.0226 (4)
C14	−0.2301 (3)	0.04253 (18)	0.50496 (19)	0.0336 (5)
H14A	−0.3315	0.0568	0.5597	0.050*
H14B	−0.1846	−0.0268	0.5249	0.050*
H14C	−0.2346	0.0340	0.4307	0.050*
C15	0.4883 (3)	0.65322 (18)	0.10939 (18)	0.0340 (5)
H15A	0.5947	0.6369	0.0955	0.051*
H15B	0.4637	0.7344	0.1220	0.051*
H15C	0.4664	0.6300	0.0446	0.051*
C16	−0.1702 (3)	0.1401 (2)	0.81220 (18)	0.0356 (5)
H16A	−0.2563	0.1125	0.8748	0.043*
H16B	−0.1669	0.2221	0.8232	0.043*
C17	−0.0246 (3)	0.0790 (2)	0.8149 (2)	0.0430 (6)
H17A	−0.0166	0.0912	0.8875	0.065*
H17B	0.0616	0.1091	0.7558	0.065*
H17C	−0.0264	−0.0021	0.8030	0.065*
C18	0.5156 (3)	0.70902 (18)	0.43894 (18)	0.0332 (5)
H18A	0.5445	0.6376	0.4692	0.040*
H18B	0.4178	0.7385	0.4926	0.040*
C19	0.6339 (3)	0.7956 (2)	0.4249 (2)	0.0440 (6)
H19A	0.6491	0.8037	0.4956	0.066*
H19B	0.5996	0.8688	0.4032	0.066*
H19C	0.7284	0.7694	0.3670	0.066*
C20	0.0194 (2)	0.37728 (17)	0.21702 (16)	0.0270 (5)
C21	−0.1042 (3)	0.45691 (19)	0.24627 (19)	0.0358 (5)
H21	−0.1309	0.5013	0.3119	0.043*
C22	−0.1875 (3)	0.4690 (2)	0.1750 (2)	0.0460 (6)
H22	−0.2711	0.5219	0.1932	0.055*
C23	−0.1468 (3)	0.4026 (3)	0.0771 (2)	0.0546 (7)
H23	−0.2044	0.4114	0.0309	0.066*
C24	−0.0228 (3)	0.3239 (2)	0.0468 (2)	0.0474 (7)
H24	0.0051	0.2805	−0.0195	0.057*
C25	0.0590 (3)	0.31164 (19)	0.11906 (17)	0.0345 (5)
C26	0.1915 (3)	0.23186 (19)	0.11213 (17)	0.0361 (6)
C1X	0.3369 (3)	0.18022 (18)	0.23495 (19)	0.0363 (5)
H1XA	0.3461	0.1050	0.2004	0.044*
H1XB	0.2973	0.1696	0.3169	0.044*
C2X	0.4946 (3)	0.22520 (19)	0.2004 (2)	0.0384 (5)
H2XA	0.4872	0.3001	0.2351	0.046*
H2XB	0.5365	0.2349	0.1184	0.046*
C3X	0.6022 (3)	0.1425 (2)	0.23707 (19)	0.0396 (6)
H3XA	0.7007	0.1753	0.2165	0.047*
H3XB	0.5609	0.1335	0.3191	0.047*
C4X	0.6225 (3)	0.02633 (19)	0.18166 (18)	0.0333 (5)
O1X	0.5444 (2)	−0.05366 (14)	0.22250 (14)	0.0522 (5)
O2X	0.7318 (2)	0.02190 (15)	0.08066 (13)	0.0495 (5)
H2X	0.728 (5)	−0.058 (4)	0.039 (4)	0.140 (16)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0337 (8)	0.0266 (7)	0.0218 (7)	−0.0141 (6)	−0.0094 (6)	0.0050 (5)
O2	0.0624 (13)	0.0425 (10)	0.0376 (9)	−0.0136 (9)	0.0027 (9)	−0.0190 (8)
N1	0.0370 (12)	0.0410 (11)	0.0327 (10)	−0.0187 (9)	−0.0108 (9)	0.0137 (8)
N2	0.0333 (11)	0.0265 (9)	0.0348 (10)	−0.0126 (8)	−0.0144 (8)	0.0077 (8)
N3	0.0331 (10)	0.0243 (9)	0.0285 (9)	−0.0049 (7)	−0.0043 (8)	−0.0021 (7)
C1	0.0228 (10)	0.0196 (9)	0.0270 (10)	−0.0055 (8)	−0.0091 (8)	0.0023 (8)
C2	0.0252 (11)	0.0252 (10)	0.0240 (10)	−0.0062 (8)	−0.0082 (8)	0.0039 (8)
C3	0.0207 (10)	0.0246 (10)	0.0263 (10)	−0.0033 (8)	−0.0037 (8)	0.0050 (8)
C4	0.0226 (11)	0.0230 (10)	0.0325 (11)	−0.0040 (8)	−0.0088 (9)	0.0014 (8)
C5	0.0296 (12)	0.0255 (10)	0.0246 (10)	−0.0069 (8)	−0.0092 (9)	0.0007 (8)
C6	0.0260 (11)	0.0228 (10)	0.0217 (10)	−0.0040 (8)	−0.0071 (8)	0.0024 (7)
C7	0.0288 (11)	0.0226 (10)	0.0249 (10)	−0.0040 (8)	−0.0096 (9)	0.0001 (8)
C8	0.0242 (11)	0.0192 (9)	0.0243 (10)	−0.0053 (8)	−0.0071 (8)	0.0033 (7)
C9	0.0287 (11)	0.0243 (10)	0.0202 (9)	−0.0025 (8)	−0.0076 (8)	0.0026 (8)
C10	0.0250 (11)	0.0229 (10)	0.0259 (10)	−0.0036 (8)	−0.0062 (9)	0.0066 (8)
C11	0.0221 (11)	0.0225 (10)	0.0288 (10)	−0.0047 (8)	−0.0089 (8)	0.0032 (8)
C12	0.0274 (11)	0.0224 (10)	0.0241 (10)	−0.0052 (8)	−0.0102 (9)	0.0003 (8)
C13	0.0226 (10)	0.0206 (9)	0.0220 (10)	−0.0033 (8)	−0.0047 (8)	0.0030 (7)
C14	0.0333 (13)	0.0296 (11)	0.0381 (12)	−0.0129 (9)	−0.0118 (10)	0.0039 (9)
C15	0.0340 (13)	0.0334 (12)	0.0320 (11)	−0.0088 (10)	−0.0083 (10)	0.0097 (9)
C16	0.0385 (14)	0.0374 (12)	0.0277 (11)	−0.0086 (10)	−0.0077 (10)	0.0080 (9)
C17	0.0472 (16)	0.0432 (14)	0.0375 (13)	−0.0076 (11)	−0.0137 (11)	0.0089 (10)
C18	0.0348 (13)	0.0292 (11)	0.0403 (13)	−0.0120 (9)	−0.0182 (10)	0.0078 (9)
C19	0.0403 (14)	0.0413 (14)	0.0589 (16)	−0.0160 (11)	−0.0264 (13)	0.0064 (11)
C20	0.0285 (11)	0.0286 (11)	0.0253 (10)	−0.0112 (9)	−0.0102 (9)	0.0067 (8)
C21	0.0366 (13)	0.0387 (13)	0.0336 (12)	−0.0067 (10)	−0.0140 (10)	0.0074 (10)
C22	0.0459 (16)	0.0517 (15)	0.0476 (15)	−0.0070 (12)	−0.0256 (13)	0.0134 (12)
C23	0.0596 (19)	0.0696 (19)	0.0519 (16)	−0.0216 (15)	−0.0389 (15)	0.0187 (14)
C24	0.0637 (19)	0.0560 (16)	0.0303 (12)	−0.0269 (14)	−0.0229 (12)	0.0061 (11)
C25	0.0426 (14)	0.0342 (12)	0.0276 (11)	−0.0166 (10)	−0.0118 (10)	0.0049 (9)
C26	0.0438 (14)	0.0339 (12)	0.0244 (11)	−0.0198 (10)	−0.0022 (10)	0.0000 (9)
C1X	0.0356 (13)	0.0272 (11)	0.0379 (12)	−0.0010 (9)	−0.0039 (10)	0.0044 (9)
C2X	0.0376 (14)	0.0315 (12)	0.0426 (13)	−0.0026 (10)	−0.0104 (11)	−0.0005 (10)
C3X	0.0421 (14)	0.0396 (13)	0.0360 (12)	−0.0001 (10)	−0.0131 (11)	−0.0038 (10)
C4X	0.0317 (13)	0.0350 (12)	0.0297 (11)	0.0011 (10)	−0.0076 (10)	0.0032 (9)
O1X	0.0556 (12)	0.0335 (9)	0.0508 (10)	−0.0054 (8)	0.0007 (9)	0.0070 (8)
O2X	0.0553 (12)	0.0435 (10)	0.0366 (9)	−0.0117 (8)	0.0007 (8)	−0.0049 (8)

Geometric parameters (Å, º)

O1—C13	1.381 (2)	C15—H15B	0.9600
O1—C1	1.384 (2)	C15—H15C	0.9600
O2—C26	1.229 (3)	C16—C17	1.516 (3)
N1—C3	1.380 (3)	C16—H16A	0.9700
N1—C16	1.448 (3)	C16—H16B	0.9700
N1—H1N	0.83 (2)	C17—H17A	0.9600
N2—C11	1.384 (2)	C17—H17B	0.9600
N2—C18	1.447 (3)	C17—H17C	0.9600
N2—H2N	0.85 (2)	C18—C19	1.511 (3)
N3—C26	1.350 (3)	C18—H18A	0.9700
N3—C1X	1.451 (3)	C18—H18B	0.9700
N3—C7	1.503 (3)	C19—H19A	0.9600
C1—C6	1.381 (3)	C19—H19B	0.9600
C1—C2	1.390 (3)	C19—H19C	0.9600
C2—C3	1.392 (3)	C20—C21	1.383 (3)
C2—H2	0.9300	C20—C25	1.385 (3)
C3—C4	1.416 (3)	C21—C22	1.391 (3)
C4—C5	1.372 (3)	C21—H21	0.9300
C4—C14	1.511 (3)	C22—C23	1.388 (4)
C5—C6	1.403 (3)	C22—H22	0.9300
C5—H5	0.9300	C23—C24	1.379 (4)
C6—C7	1.513 (3)	C23—H23	0.9300
C7—C8	1.517 (3)	C24—C25	1.391 (3)
C7—C20	1.523 (3)	C24—H24	0.9300
C8—C13	1.379 (3)	C25—C26	1.483 (3)
C8—C9	1.404 (3)	C1X—C2X	1.513 (3)
C9—C10	1.379 (3)	C1X—H1XA	0.9700
C9—H9	0.9300	C1X—H1XB	0.9700
C10—C11	1.418 (3)	C2X—C3X	1.537 (3)
C10—C15	1.504 (3)	C2X—H2XA	0.9700
C11—C12	1.392 (3)	C2X—H2XB	0.9700
C12—C13	1.389 (3)	C3X—C4X	1.503 (3)
C12—H12	0.9300	C3X—H3XA	0.9700
C14—H14A	0.9600	C3X—H3XB	0.9700
C14—H14B	0.9600	C4X—O1X	1.209 (3)
C14—H14C	0.9600	C4X—O2X	1.315 (3)
C15—H15A	0.9600	O2X—H2X	1.09 (4)
C13—O1—C1	118.18 (14)	C17—C16—H16A	109.0
C3—N1—C16	124.43 (18)	N1—C16—H16B	109.0
C3—N1—H1N	117.7 (19)	C17—C16—H16B	109.0
C16—N1—H1N	117.2 (18)	H16A—C16—H16B	107.8
C11—N2—C18	121.40 (17)	C16—C17—H17A	109.5
C11—N2—H2N	117.6 (17)	C16—C17—H17B	109.5
C18—N2—H2N	114.6 (17)	H17A—C17—H17B	109.5
C26—N3—C1X	122.50 (18)	C16—C17—H17C	109.5
C26—N3—C7	114.09 (18)	H17A—C17—H17C	109.5
C1X—N3—C7	122.42 (16)	H17B—C17—H17C	109.5
C6—C1—O1	122.87 (16)	N2—C18—C19	110.33 (17)
C6—C1—C2	122.27 (17)	N2—C18—H18A	109.6
O1—C1—C2	114.86 (16)	C19—C18—H18A	109.6
C1—C2—C3	120.20 (17)	N2—C18—H18B	109.6
C1—C2—H2	119.9	C19—C18—H18B	109.6
C3—C2—H2	119.9	H18A—C18—H18B	108.1
N1—C3—C2	121.76 (18)	C18—C19—H19A	109.5
N1—C3—C4	119.32 (17)	C18—C19—H19B	109.5
C2—C3—C4	118.91 (17)	H19A—C19—H19B	109.5
C5—C4—C3	118.67 (17)	C18—C19—H19C	109.5
C5—C4—C14	120.52 (18)	H19A—C19—H19C	109.5
C3—C4—C14	120.78 (17)	H19B—C19—H19C	109.5
C4—C5—C6	123.54 (18)	C21—C20—C25	120.7 (2)
C4—C5—H5	118.2	C21—C20—C7	128.55 (18)
C6—C5—H5	118.2	C25—C20—C7	110.70 (19)
C1—C6—C5	116.39 (17)	C20—C21—C22	118.3 (2)
C1—C6—C7	122.74 (17)	C20—C21—H21	120.8
C5—C6—C7	120.80 (17)	C22—C21—H21	120.8
N3—C7—C6	109.85 (15)	C23—C22—C21	120.5 (3)
N3—C7—C8	109.97 (16)	C23—C22—H22	119.7
C6—C7—C8	110.27 (15)	C21—C22—H22	119.7
N3—C7—C20	99.79 (15)	C24—C23—C22	121.5 (2)
C6—C7—C20	112.42 (17)	C24—C23—H23	119.3
C8—C7—C20	114.05 (15)	C22—C23—H23	119.3
C13—C8—C9	116.91 (17)	C23—C24—C25	117.6 (2)
C13—C8—C7	121.97 (16)	C23—C24—H24	121.2
C9—C8—C7	120.94 (17)	C25—C24—H24	121.2
C10—C9—C8	123.47 (18)	C20—C25—C24	121.4 (2)
C10—C9—H9	118.3	C20—C25—C26	108.56 (19)
C8—C9—H9	118.3	C24—C25—C26	130.0 (2)
C9—C10—C11	118.10 (17)	O2—C26—N3	125.2 (2)
C9—C10—C15	121.25 (18)	O2—C26—C25	128.0 (2)
C11—C10—C15	120.63 (17)	N3—C26—C25	106.79 (18)
N2—C11—C12	120.81 (18)	N3—C1X—C2X	115.45 (17)
N2—C11—C10	119.91 (17)	N3—C1X—H1XA	108.4
C12—C11—C10	119.24 (17)	C2X—C1X—H1XA	108.4
C13—C12—C11	120.49 (17)	N3—C1X—H1XB	108.4
C13—C12—H12	119.8	C2X—C1X—H1XB	108.4
C11—C12—H12	119.8	H1XA—C1X—H1XB	107.5
C8—C13—O1	123.62 (16)	C1X—C2X—C3X	111.43 (19)
C8—C13—C12	121.78 (17)	C1X—C2X—H2XA	109.3
O1—C13—C12	114.59 (16)	C3X—C2X—H2XA	109.3
C4—C14—H14A	109.5	C1X—C2X—H2XB	109.3
C4—C14—H14B	109.5	C3X—C2X—H2XB	109.3
H14A—C14—H14B	109.5	H2XA—C2X—H2XB	108.0
C4—C14—H14C	109.5	C4X—C3X—C2X	111.44 (19)
H14A—C14—H14C	109.5	C4X—C3X—H3XA	109.3
H14B—C14—H14C	109.5	C2X—C3X—H3XA	109.3
C10—C15—H15A	109.5	C4X—C3X—H3XB	109.3
C10—C15—H15B	109.5	C2X—C3X—H3XB	109.3
H15A—C15—H15B	109.5	H3XA—C3X—H3XB	108.0
C10—C15—H15C	109.5	O1X—C4X—O2X	123.0 (2)
H15A—C15—H15C	109.5	O1X—C4X—C3X	124.5 (2)
H15B—C15—H15C	109.5	O2X—C4X—C3X	112.48 (19)
N1—C16—C17	112.93 (19)	C4X—O2X—H2X	109 (2)
N1—C16—H16A	109.0
C13—O1—C1—C6	0.0 (3)	C9—C10—C11—C12	−0.4 (3)
C13—O1—C1—C2	179.65 (17)	C15—C10—C11—C12	−178.73 (19)
C6—C1—C2—C3	0.8 (3)	N2—C11—C12—C13	−176.96 (18)
O1—C1—C2—C3	−178.87 (17)	C10—C11—C12—C13	0.9 (3)
C16—N1—C3—C2	−7.6 (3)	C9—C8—C13—O1	179.19 (18)
C16—N1—C3—C4	172.0 (2)	C7—C8—C13—O1	−5.7 (3)
C1—C2—C3—N1	179.84 (19)	C9—C8—C13—C12	−0.1 (3)
C1—C2—C3—C4	0.2 (3)	C7—C8—C13—C12	175.08 (18)
N1—C3—C4—C5	179.0 (2)	C1—O1—C13—C8	1.8 (3)
C2—C3—C4—C5	−1.3 (3)	C1—O1—C13—C12	−178.92 (17)
N1—C3—C4—C14	−3.0 (3)	C11—C12—C13—C8	−0.7 (3)
C2—C3—C4—C14	176.63 (19)	C11—C12—C13—O1	−179.99 (17)
C3—C4—C5—C6	1.6 (3)	C3—N1—C16—C17	−76.7 (3)
C14—C4—C5—C6	−176.34 (19)	C11—N2—C18—C19	178.10 (19)
O1—C1—C6—C5	179.09 (18)	N3—C7—C20—C21	178.85 (19)
C2—C1—C6—C5	−0.5 (3)	C6—C7—C20—C21	62.5 (3)
O1—C1—C6—C7	2.2 (3)	C8—C7—C20—C21	−64.0 (3)
C2—C1—C6—C7	−177.44 (19)	N3—C7—C20—C25	2.37 (19)
C4—C5—C6—C1	−0.7 (3)	C6—C7—C20—C25	−113.99 (18)
C4—C5—C6—C7	176.28 (19)	C8—C7—C20—C25	119.53 (18)
C26—N3—C7—C6	115.45 (18)	C25—C20—C21—C22	0.2 (3)
C1X—N3—C7—C6	−53.4 (2)	C7—C20—C21—C22	−175.99 (19)
C26—N3—C7—C8	−123.01 (18)	C20—C21—C22—C23	−0.1 (3)
C1X—N3—C7—C8	68.1 (2)	C21—C22—C23—C24	−0.6 (4)
C26—N3—C7—C20	−2.83 (19)	C22—C23—C24—C25	1.1 (4)
C1X—N3—C7—C20	−171.68 (16)	C21—C20—C25—C24	0.4 (3)
C1—C6—C7—N3	116.1 (2)	C7—C20—C25—C24	177.19 (18)
C5—C6—C7—N3	−60.7 (2)	C21—C20—C25—C26	−178.09 (18)
C1—C6—C7—C8	−5.2 (3)	C7—C20—C25—C26	−1.3 (2)
C5—C6—C7—C8	177.97 (18)	C23—C24—C25—C20	−1.0 (3)
C1—C6—C7—C20	−133.7 (2)	C23—C24—C25—C26	177.1 (2)
C5—C6—C7—C20	49.5 (2)	C1X—N3—C26—O2	−8.5 (3)
N3—C7—C8—C13	−114.4 (2)	C7—N3—C26—O2	−177.39 (18)
C6—C7—C8—C13	6.9 (3)	C1X—N3—C26—C25	171.07 (17)
C20—C7—C8—C13	134.5 (2)	C7—N3—C26—C25	2.2 (2)
N3—C7—C8—C9	60.5 (2)	C20—C25—C26—O2	179.1 (2)
C6—C7—C8—C9	−178.17 (18)	C24—C25—C26—O2	0.8 (4)
C20—C7—C8—C9	−50.6 (3)	C20—C25—C26—N3	−0.5 (2)
C13—C8—C9—C10	0.6 (3)	C24—C25—C26—N3	−178.8 (2)
C7—C8—C9—C10	−174.61 (19)	C26—N3—C1X—C2X	99.8 (2)
C8—C9—C10—C11	−0.4 (3)	C7—N3—C1X—C2X	−92.3 (2)
C8—C9—C10—C15	177.98 (19)	N3—C1X—C2X—C3X	179.81 (18)
C18—N2—C11—C12	−1.8 (3)	C1X—C2X—C3X—C4X	61.3 (3)
C18—N2—C11—C10	−179.63 (19)	C2X—C3X—C4X—O1X	−91.3 (3)
C9—C10—C11—N2	177.49 (19)	C2X—C3X—C4X—O2X	86.3 (2)
C15—C10—C11—N2	−0.9 (3)