3′,6′-Bis(diethyl­amino)-2-(quinolin-8-yl)spiro­[1H-isoindoline-1,9′-xanthen]-3(2H)-one

The title compound, C₃₇H₃₆N₄O₂, has been obtained by the reaction of 2-[3,6-bis­(diethyl­amino)-9H-xanthen-9-yl]benzoyl chloride with 8-amino­quinoline. The mol­ecular packing in the crystal structure is stabilized by weak C—H...O hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 223 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.048
• wR factor = 0.139
• Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT410_ALERT_2_C Short Intra H...H Contact  H4A    ..  H30B    ..       1.98 Ang.
PLAT410_ALERT_2_C Short Intra H...H Contact  H10A   ..  H36A    ..       1.98 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

3',6'-Bis(diethylamino)-2-(quinolin-8-yl)spiro[1H-isoindoline-1,9'- xanthen]-3(2H)-one

Crystal data

C37H36N4O2	F(000) = 1208
Mr = 568.70	Dx = 1.281 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5261 reflections
a = 10.634 (2) Å	θ = 2.2–27.6°
b = 23.577 (4) Å	µ = 0.08 mm^−1
c = 12.614 (2) Å	T = 223 K
β = 111.222 (3)°	Block, colorless
V = 2948.1 (9) Å^3	0.41 × 0.41 × 0.40 mm
Z = 4

Data collection

Bruker APEX area-detector diffractometer	4748 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
Graphite monochromator	θmax = 26.0°, θmin = 1.7°
φ and ω scans	h = −13→7
15966 measured reflections	k = −27→29
5771 independent reflections	l = −14→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.139	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0876P)^2 + 0.4047P] where P = (Fo^2 + 2Fc^2)/3
5771 reflections	(Δ/σ)max < 0.001
392 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
O1	0.16435 (11)	0.01475 (4)	0.58887 (9)	0.0298 (3)
C2	0.12368 (15)	−0.07151 (6)	0.65838 (13)	0.0269 (3)
H2A	0.1479	−0.0884	0.6010	0.032*
O2	0.10871 (12)	0.15763 (5)	1.00345 (9)	0.0369 (3)
N1	0.08054 (14)	−0.16379 (5)	0.71894 (12)	0.0334 (3)
C13	0.17163 (15)	0.07313 (6)	0.59310 (12)	0.0251 (3)
C1	0.12551 (14)	−0.01321 (6)	0.66820 (12)	0.0242 (3)
C7	0.08312 (15)	0.07796 (6)	0.75506 (12)	0.0254 (3)
C12	0.22003 (16)	0.09742 (6)	0.51570 (13)	0.0281 (3)
H12A	0.2465	0.0740	0.4672	0.034*
N3	0.15559 (12)	0.10157 (5)	0.87174 (10)	0.0253 (3)
C9	0.14281 (16)	0.16350 (6)	0.66013 (13)	0.0305 (4)
H9A	0.1159	0.1865	0.7090	0.037*
C8	0.13287 (14)	0.10481 (6)	0.66806 (12)	0.0255 (3)
C4	0.05572 (15)	−0.07826 (6)	0.81928 (13)	0.0289 (3)
H4A	0.0327	−0.0998	0.8723	0.035*
C3	0.08640 (14)	−0.10589 (6)	0.73225 (13)	0.0259 (3)
C5	0.05922 (15)	−0.02030 (6)	0.82702 (13)	0.0275 (3)
H5A	0.0382	−0.0031	0.8857	0.033*
N4	0.23584 (13)	0.04218 (6)	1.07687 (12)	0.0343 (3)
C10	0.18983 (16)	0.18904 (6)	0.58471 (13)	0.0314 (4)
H10A	0.1955	0.2288	0.5834	0.038*
N2	0.27321 (14)	0.18155 (6)	0.42897 (11)	0.0327 (3)
C11	0.23029 (15)	0.15630 (6)	0.50828 (13)	0.0275 (3)
C6	0.09274 (14)	0.01421 (6)	0.75140 (12)	0.0244 (3)
C22	0.33323 (15)	0.06195 (6)	1.03998 (13)	0.0286 (3)
C32	0.12557 (17)	−0.19060 (7)	0.63569 (14)	0.0355 (4)
H32A	0.0872	−0.1700	0.5636	0.043*
H32B	0.0902	−0.2294	0.6228	0.043*
C20	0.07363 (16)	0.13151 (6)	0.91423 (13)	0.0275 (3)
C14	−0.05956 (15)	0.09720 (6)	0.73574 (13)	0.0264 (3)
C19	−0.06405 (15)	0.12736 (6)	0.82747 (13)	0.0276 (3)
C26	0.47297 (16)	0.05429 (7)	1.10295 (14)	0.0337 (4)
C15	−0.17516 (16)	0.08765 (7)	0.64143 (14)	0.0333 (4)
H15A	−0.1725	0.0667	0.5789	0.040*
C21	0.29487 (15)	0.09112 (6)	0.93421 (13)	0.0269 (3)
C29	0.39166 (16)	0.10833 (7)	0.89344 (14)	0.0349 (4)
H29A	0.3658	0.1272	0.8232	0.042*
C36	0.31780 (17)	0.24072 (7)	0.44547 (15)	0.0354 (4)
H36A	0.2510	0.2631	0.4641	0.042*
H36B	0.3211	0.2553	0.3738	0.042*
C34	0.3244 (2)	0.14489 (8)	0.36058 (16)	0.0442 (4)
H34A	0.2581	0.1148	0.3277	0.053*
H34B	0.4072	0.1267	0.4113	0.053*
C18	−0.18435 (17)	0.14935 (7)	0.82923 (15)	0.0360 (4)
H18A	−0.1871	0.1697	0.8924	0.043*
C27	0.56924 (16)	0.07250 (8)	1.05796 (16)	0.0394 (4)
H27A	0.6616	0.0669	1.0994	0.047*
C30	0.03421 (17)	−0.20092 (7)	0.78906 (15)	0.0367 (4)
H30A	−0.0246	−0.2300	0.7404	0.044*
H30B	−0.0200	−0.1787	0.8224	0.044*
C28	0.52898 (17)	0.09818 (8)	0.95500 (16)	0.0414 (4)
H28A	0.5937	0.1093	0.9244	0.050*
C25	0.50858 (17)	0.02716 (8)	1.20918 (16)	0.0430 (4)
H25A	0.5999	0.0218	1.2543	0.052*
C23	0.27635 (18)	0.01653 (8)	1.17611 (16)	0.0435 (4)
H23A	0.2098	0.0023	1.2018	0.052*
C24	0.41137 (18)	0.00887 (8)	1.24616 (17)	0.0477 (5)
H24A	0.4340	−0.0087	1.3176	0.057*
C35	0.3544 (2)	0.17303 (9)	0.26633 (16)	0.0495 (5)
H35A	0.3806	0.1446	0.2227	0.074*
H35B	0.4275	0.1999	0.2979	0.074*
H35C	0.2746	0.1928	0.2172	0.074*
C16	−0.29482 (17)	0.11023 (8)	0.64279 (16)	0.0405 (4)
H16A	−0.3747	0.1050	0.5794	0.049*
C17	−0.29914 (17)	0.14041 (8)	0.73569 (16)	0.0420 (4)
H17A	−0.3819	0.1550	0.7346	0.050*
C37	0.4541 (2)	0.24900 (9)	0.53788 (18)	0.0541 (5)
H37A	0.4740	0.2892	0.5483	0.081*
H37B	0.5225	0.2303	0.5164	0.081*
H37C	0.4533	0.2329	0.6084	0.081*
C33	0.27738 (19)	−0.19280 (8)	0.66931 (17)	0.0460 (5)
H33A	0.2996	−0.2094	0.6080	0.069*
H33B	0.3159	−0.2157	0.7373	0.069*
H33C	0.3138	−0.1547	0.6842	0.069*
C31	0.1455 (2)	−0.22960 (9)	0.88296 (17)	0.0536 (5)
H31A	0.1076	−0.2507	0.9303	0.080*
H31B	0.2078	−0.2013	0.9287	0.080*
H31C	0.1930	−0.2554	0.8507	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0439 (7)	0.0218 (5)	0.0297 (6)	−0.0029 (4)	0.0207 (5)	−0.0011 (4)
C2	0.0298 (8)	0.0266 (8)	0.0242 (8)	−0.0005 (6)	0.0095 (6)	−0.0024 (6)
O2	0.0418 (7)	0.0385 (7)	0.0333 (6)	−0.0021 (5)	0.0170 (5)	−0.0100 (5)
N1	0.0402 (8)	0.0245 (7)	0.0386 (8)	−0.0026 (5)	0.0179 (6)	0.0024 (5)
C13	0.0270 (8)	0.0221 (7)	0.0240 (7)	0.0001 (6)	0.0064 (6)	0.0010 (6)
C1	0.0229 (7)	0.0259 (8)	0.0227 (7)	−0.0010 (6)	0.0071 (6)	0.0024 (6)
C7	0.0264 (8)	0.0265 (8)	0.0229 (8)	0.0007 (6)	0.0085 (6)	−0.0012 (6)
C12	0.0323 (8)	0.0274 (8)	0.0267 (8)	−0.0001 (6)	0.0132 (7)	−0.0014 (6)
N3	0.0251 (7)	0.0281 (7)	0.0233 (6)	−0.0005 (5)	0.0094 (5)	−0.0028 (5)
C9	0.0369 (9)	0.0267 (8)	0.0298 (8)	0.0024 (6)	0.0145 (7)	−0.0028 (6)
C8	0.0255 (8)	0.0269 (8)	0.0234 (7)	0.0005 (6)	0.0081 (6)	0.0009 (6)
C4	0.0276 (8)	0.0313 (8)	0.0289 (8)	−0.0012 (6)	0.0114 (7)	0.0068 (6)
C3	0.0215 (7)	0.0258 (8)	0.0266 (8)	−0.0007 (6)	0.0042 (6)	0.0023 (6)
C5	0.0249 (8)	0.0321 (8)	0.0270 (8)	0.0018 (6)	0.0111 (6)	0.0009 (6)
N4	0.0286 (7)	0.0383 (8)	0.0349 (8)	−0.0038 (6)	0.0102 (6)	0.0030 (6)
C10	0.0388 (9)	0.0219 (8)	0.0343 (9)	−0.0014 (6)	0.0144 (7)	0.0001 (6)
N2	0.0407 (8)	0.0293 (7)	0.0321 (7)	−0.0023 (6)	0.0181 (6)	0.0028 (6)
C11	0.0274 (8)	0.0279 (8)	0.0259 (8)	−0.0011 (6)	0.0081 (6)	0.0023 (6)
C6	0.0216 (7)	0.0258 (8)	0.0248 (8)	−0.0001 (6)	0.0071 (6)	0.0000 (6)
C22	0.0254 (8)	0.0285 (8)	0.0311 (8)	−0.0007 (6)	0.0092 (7)	−0.0051 (6)
C32	0.0416 (9)	0.0258 (8)	0.0377 (9)	−0.0040 (7)	0.0125 (8)	−0.0025 (7)
C20	0.0330 (8)	0.0253 (8)	0.0286 (8)	−0.0012 (6)	0.0164 (7)	−0.0002 (6)
C14	0.0280 (8)	0.0242 (7)	0.0282 (8)	0.0003 (6)	0.0119 (6)	0.0056 (6)
C19	0.0301 (8)	0.0232 (7)	0.0330 (8)	0.0007 (6)	0.0155 (7)	0.0039 (6)
C26	0.0263 (8)	0.0339 (9)	0.0365 (9)	0.0000 (7)	0.0063 (7)	−0.0057 (7)
C15	0.0321 (9)	0.0380 (9)	0.0287 (8)	0.0004 (7)	0.0097 (7)	0.0061 (7)
C21	0.0249 (8)	0.0275 (8)	0.0281 (8)	−0.0023 (6)	0.0094 (6)	−0.0075 (6)
C29	0.0326 (9)	0.0432 (10)	0.0309 (9)	−0.0065 (7)	0.0139 (7)	−0.0043 (7)
C36	0.0426 (10)	0.0273 (8)	0.0400 (9)	0.0001 (7)	0.0194 (8)	0.0078 (7)
C34	0.0589 (12)	0.0386 (10)	0.0431 (10)	0.0023 (8)	0.0281 (9)	0.0035 (8)
C18	0.0368 (9)	0.0324 (9)	0.0454 (10)	0.0074 (7)	0.0228 (8)	0.0044 (7)
C27	0.0225 (8)	0.0494 (11)	0.0427 (10)	−0.0015 (7)	0.0075 (7)	−0.0083 (8)
C30	0.0414 (9)	0.0266 (8)	0.0438 (10)	−0.0065 (7)	0.0174 (8)	0.0028 (7)
C28	0.0293 (9)	0.0556 (11)	0.0436 (10)	−0.0083 (8)	0.0183 (8)	−0.0086 (8)
C25	0.0279 (9)	0.0476 (11)	0.0430 (10)	0.0029 (7)	0.0002 (8)	0.0039 (8)
C23	0.0352 (9)	0.0513 (11)	0.0412 (10)	−0.0041 (8)	0.0105 (8)	0.0133 (8)
C24	0.0412 (10)	0.0533 (12)	0.0398 (10)	−0.0017 (9)	0.0042 (8)	0.0140 (9)
C35	0.0562 (12)	0.0553 (12)	0.0432 (11)	−0.0026 (9)	0.0255 (10)	0.0009 (9)
C16	0.0272 (8)	0.0470 (10)	0.0410 (10)	0.0021 (7)	0.0049 (7)	0.0135 (8)
C17	0.0303 (9)	0.0421 (10)	0.0566 (12)	0.0108 (7)	0.0193 (9)	0.0149 (9)
C37	0.0493 (12)	0.0487 (12)	0.0584 (13)	−0.0132 (9)	0.0124 (10)	0.0027 (9)
C33	0.0439 (10)	0.0458 (11)	0.0492 (11)	0.0053 (8)	0.0178 (9)	−0.0036 (8)
C31	0.0653 (13)	0.0567 (12)	0.0397 (11)	0.0068 (10)	0.0201 (10)	0.0148 (9)

Geometric parameters (Å, º)

O1—C13	1.3784 (18)	C19—C18	1.388 (2)
O1—C1	1.3804 (17)	C26—C27	1.405 (2)
C2—C1	1.380 (2)	C26—C25	1.407 (3)
C2—C3	1.396 (2)	C15—C16	1.385 (2)
C2—H2A	0.9400	C15—H15A	0.9400
O2—C20	1.2169 (18)	C21—C29	1.368 (2)
N1—C3	1.374 (2)	C29—C28	1.404 (2)
N1—C32	1.448 (2)	C29—H29A	0.9400
N1—C30	1.452 (2)	C36—C37	1.508 (3)
C13—C8	1.380 (2)	C36—H36A	0.9800
C13—C12	1.382 (2)	C36—H36B	0.9800
C1—C6	1.380 (2)	C34—C35	1.493 (2)
C7—N3	1.4997 (19)	C34—H34A	0.9800
C7—C6	1.508 (2)	C34—H34B	0.9800
C7—C14	1.516 (2)	C18—C17	1.373 (3)
C7—C8	1.518 (2)	C18—H18A	0.9400
C12—C11	1.398 (2)	C27—C28	1.354 (3)
C12—H12A	0.9400	C27—H27A	0.9400
N3—C20	1.3723 (19)	C30—C31	1.498 (3)
N3—C21	1.4248 (19)	C30—H30A	0.9800
C9—C10	1.365 (2)	C30—H30B	0.9800
C9—C8	1.394 (2)	C28—H28A	0.9400
C9—H9A	0.9400	C25—C24	1.349 (3)
C4—C5	1.370 (2)	C25—H25A	0.9400
C4—C3	1.412 (2)	C23—C24	1.399 (2)
C4—H4A	0.9400	C23—H23A	0.9400
C5—C6	1.395 (2)	C24—H24A	0.9400
C5—H5A	0.9400	C35—H35A	0.9700
N4—C23	1.315 (2)	C35—H35B	0.9700
N4—C22	1.362 (2)	C35—H35C	0.9700
C10—C11	1.418 (2)	C16—C17	1.386 (3)
C10—H10A	0.9400	C16—H16A	0.9400
N2—C11	1.3763 (19)	C17—H17A	0.9400
N2—C34	1.459 (2)	C37—H37A	0.9700
N2—C36	1.464 (2)	C37—H37B	0.9700
C22—C26	1.420 (2)	C37—H37C	0.9700
C22—C21	1.423 (2)	C33—H33A	0.9700
C32—C33	1.514 (2)	C33—H33B	0.9700
C32—H32A	0.9800	C33—H33C	0.9700
C32—H32B	0.9800	C31—H31A	0.9700
C20—C19	1.480 (2)	C31—H31B	0.9700
C14—C19	1.374 (2)	C31—H31C	0.9700
C14—C15	1.385 (2)
C13—O1—C1	118.43 (11)	C14—C15—H15A	121.3
C1—C2—C3	121.11 (14)	C16—C15—H15A	121.3
C1—C2—H2A	119.4	C29—C21—C22	119.76 (14)
C3—C2—H2A	119.4	C29—C21—N3	120.90 (14)
C3—N1—C32	120.67 (13)	C22—C21—N3	119.34 (13)
C3—N1—C30	122.35 (13)	C21—C29—C28	120.98 (16)
C32—N1—C30	116.94 (13)	C21—C29—H29A	119.5
O1—C13—C8	122.72 (13)	C28—C29—H29A	119.5
O1—C13—C12	114.62 (13)	N2—C36—C37	113.86 (14)
C8—C13—C12	122.66 (14)	N2—C36—H36A	108.8
C2—C1—O1	114.14 (13)	C37—C36—H36A	108.8
C2—C1—C6	122.38 (13)	N2—C36—H36B	108.8
O1—C1—C6	123.47 (13)	C37—C36—H36B	108.8
N3—C7—C6	112.56 (12)	H36A—C36—H36B	107.7
N3—C7—C14	100.10 (11)	N2—C34—C35	116.14 (15)
C6—C7—C14	111.61 (12)	N2—C34—H34A	108.3
N3—C7—C8	111.39 (12)	C35—C34—H34A	108.3
C6—C7—C8	110.37 (12)	N2—C34—H34B	108.3
C14—C7—C8	110.44 (12)	C35—C34—H34B	108.3
C13—C12—C11	121.11 (14)	H34A—C34—H34B	107.4
C13—C12—H12A	119.4	C17—C18—C19	117.83 (16)
C11—C12—H12A	119.4	C17—C18—H18A	121.1
C20—N3—C21	123.57 (12)	C19—C18—H18A	121.1
C20—N3—C7	113.63 (12)	C28—C27—C26	120.02 (16)
C21—N3—C7	122.72 (11)	C28—C27—H27A	120.0
C10—C9—C8	122.98 (14)	C26—C27—H27A	120.0
C10—C9—H9A	118.5	N1—C30—C31	114.13 (15)
C8—C9—H9A	118.5	N1—C30—H30A	108.7
C13—C8—C9	116.04 (14)	C31—C30—H30A	108.7
C13—C8—C7	122.56 (13)	N1—C30—H30B	108.7
C9—C8—C7	121.40 (13)	C31—C30—H30B	108.7
C5—C4—C3	120.50 (14)	H30A—C30—H30B	107.6
C5—C4—H4A	119.8	C27—C28—C29	120.73 (16)
C3—C4—H4A	119.8	C27—C28—H28A	119.6
N1—C3—C2	120.43 (14)	C29—C28—H28A	119.6
N1—C3—C4	122.68 (13)	C24—C25—C26	119.91 (16)
C2—C3—C4	116.88 (14)	C24—C25—H25A	120.0
C4—C5—C6	122.72 (14)	C26—C25—H25A	120.0
C4—C5—H5A	118.6	N4—C23—C24	124.66 (17)
C6—C5—H5A	118.6	N4—C23—H23A	117.7
C23—N4—C22	117.07 (14)	C24—C23—H23A	117.7
C9—C10—C11	120.78 (14)	C25—C24—C23	118.68 (17)
C9—C10—H10A	119.6	C25—C24—H24A	120.7
C11—C10—H10A	119.6	C23—C24—H24A	120.7
C11—N2—C34	117.81 (13)	C34—C35—H35A	109.5
C11—N2—C36	118.98 (13)	C34—C35—H35B	109.5
C34—N2—C36	118.54 (13)	H35A—C35—H35B	109.5
N2—C11—C12	122.17 (14)	C34—C35—H35C	109.5
N2—C11—C10	121.39 (14)	H35A—C35—H35C	109.5
C12—C11—C10	116.41 (14)	H35B—C35—H35C	109.5
C1—C6—C5	116.36 (14)	C15—C16—C17	121.30 (16)
C1—C6—C7	121.91 (13)	C15—C16—H16A	119.3
C5—C6—C7	121.57 (13)	C17—C16—H16A	119.3
N4—C22—C26	122.44 (15)	C18—C17—C16	120.96 (16)
N4—C22—C21	119.36 (14)	C18—C17—H17A	119.5
C26—C22—C21	118.21 (14)	C16—C17—H17A	119.5
N1—C32—C33	114.26 (14)	C36—C37—H37A	109.5
N1—C32—H32A	108.7	C36—C37—H37B	109.5
C33—C32—H32A	108.7	H37A—C37—H37B	109.5
N1—C32—H32B	108.7	C36—C37—H37C	109.5
C33—C32—H32B	108.7	H37A—C37—H37C	109.5
H32A—C32—H32B	107.6	H37B—C37—H37C	109.5
O2—C20—N3	126.59 (15)	C32—C33—H33A	109.5
O2—C20—C19	127.39 (14)	C32—C33—H33B	109.5
N3—C20—C19	105.98 (13)	H33A—C33—H33B	109.5
C19—C14—C15	121.13 (14)	C32—C33—H33C	109.5
C19—C14—C7	110.94 (13)	H33A—C33—H33C	109.5
C15—C14—C7	127.93 (14)	H33B—C33—H33C	109.5
C14—C19—C18	121.34 (15)	C30—C31—H31A	109.5
C14—C19—C20	109.29 (13)	C30—C31—H31B	109.5
C18—C19—C20	129.36 (15)	H31A—C31—H31B	109.5
C27—C26—C25	122.62 (15)	C30—C31—H31C	109.5
C27—C26—C22	120.19 (16)	H31A—C31—H31C	109.5
C25—C26—C22	117.18 (15)	H31B—C31—H31C	109.5
C14—C15—C16	117.42 (16)
C1—O1—C13—C8	−4.6 (2)	C23—N4—C22—C21	−178.68 (15)
C1—O1—C13—C12	175.81 (12)	C3—N1—C32—C33	74.74 (19)
C3—C2—C1—O1	−179.91 (13)	C30—N1—C32—C33	−103.17 (17)
C3—C2—C1—C6	0.8 (2)	C21—N3—C20—O2	7.9 (2)
C13—O1—C1—C2	−178.85 (12)	C7—N3—C20—O2	−175.30 (14)
C13—O1—C1—C6	0.4 (2)	C21—N3—C20—C19	−174.37 (13)
O1—C13—C12—C11	178.58 (13)	C7—N3—C20—C19	2.46 (16)
C8—C13—C12—C11	−1.0 (2)	N3—C7—C14—C19	0.63 (15)
C6—C7—N3—C20	−120.58 (13)	C6—C7—C14—C19	119.96 (13)
C14—C7—N3—C20	−1.96 (15)	C8—C7—C14—C19	−116.87 (13)
C8—C7—N3—C20	114.84 (14)	N3—C7—C14—C15	−179.41 (14)
C6—C7—N3—C21	56.28 (17)	C6—C7—C14—C15	−60.1 (2)
C14—C7—N3—C21	174.90 (12)	C8—C7—C14—C15	63.1 (2)
C8—C7—N3—C21	−68.30 (17)	C15—C14—C19—C18	0.1 (2)
O1—C13—C8—C9	−178.37 (13)	C7—C14—C19—C18	−179.99 (14)
C12—C13—C8—C9	1.2 (2)	C15—C14—C19—C20	−179.21 (13)
O1—C13—C8—C7	2.1 (2)	C7—C14—C19—C20	0.75 (16)
C12—C13—C8—C7	−178.39 (14)	O2—C20—C19—C14	175.79 (15)
C10—C9—C8—C13	−1.0 (2)	N3—C20—C19—C14	−1.95 (16)
C10—C9—C8—C7	178.53 (14)	O2—C20—C19—C18	−3.4 (3)
N3—C7—C8—C13	129.81 (14)	N3—C20—C19—C18	178.86 (15)
C6—C7—C8—C13	4.00 (19)	N4—C22—C26—C27	176.17 (15)
C14—C7—C8—C13	−119.89 (15)	C21—C22—C26—C27	−3.4 (2)
N3—C7—C8—C9	−49.75 (18)	N4—C22—C26—C25	−2.6 (2)
C6—C7—C8—C9	−175.55 (13)	C21—C22—C26—C25	177.75 (15)
C14—C7—C8—C9	60.56 (18)	C19—C14—C15—C16	0.7 (2)
C32—N1—C3—C2	6.2 (2)	C7—C14—C15—C16	−179.23 (15)
C30—N1—C3—C2	−176.03 (14)	N4—C22—C21—C29	−176.35 (14)
C32—N1—C3—C4	−173.88 (14)	C26—C22—C21—C29	3.3 (2)
C30—N1—C3—C4	3.9 (2)	N4—C22—C21—N3	3.1 (2)
C1—C2—C3—N1	177.73 (13)	C26—C22—C21—N3	−177.25 (13)
C1—C2—C3—C4	−2.2 (2)	C20—N3—C21—C29	−122.19 (16)
C5—C4—C3—N1	−178.08 (14)	C7—N3—C21—C29	61.3 (2)
C5—C4—C3—C2	1.9 (2)	C20—N3—C21—C22	58.33 (19)
C3—C4—C5—C6	−0.1 (2)	C7—N3—C21—C22	−118.22 (15)
C8—C9—C10—C11	0.7 (2)	C22—C21—C29—C28	−0.7 (2)
C34—N2—C11—C12	−7.5 (2)	N3—C21—C29—C28	179.85 (14)
C36—N2—C11—C12	−162.91 (14)	C11—N2—C36—C37	73.8 (2)
C34—N2—C11—C10	174.61 (15)	C34—N2—C36—C37	−81.46 (19)
C36—N2—C11—C10	19.2 (2)	C11—N2—C34—C35	172.92 (16)
C13—C12—C11—N2	−177.42 (14)	C36—N2—C34—C35	−31.5 (2)
C13—C12—C11—C10	0.6 (2)	C14—C19—C18—C17	−0.5 (2)
C9—C10—C11—N2	177.58 (15)	C20—C19—C18—C17	178.58 (15)
C9—C10—C11—C12	−0.5 (2)	C25—C26—C27—C28	179.71 (17)
C2—C1—C6—C5	0.9 (2)	C22—C26—C27—C28	1.0 (2)
O1—C1—C6—C5	−178.24 (13)	C3—N1—C30—C31	−100.84 (19)
C2—C1—C6—C7	−174.49 (13)	C32—N1—C30—C31	77.03 (19)
O1—C1—C6—C7	6.3 (2)	C26—C27—C28—C29	1.7 (3)
C4—C5—C6—C1	−1.3 (2)	C21—C29—C28—C27	−1.9 (3)
C4—C5—C6—C7	174.15 (13)	C27—C26—C25—C24	−177.71 (18)
N3—C7—C6—C1	−133.11 (14)	C22—C26—C25—C24	1.1 (3)
C14—C7—C6—C1	115.24 (15)	C22—N4—C23—C24	0.8 (3)
C8—C7—C6—C1	−7.97 (19)	C26—C25—C24—C23	1.2 (3)
N3—C7—C6—C5	51.71 (18)	N4—C23—C24—C25	−2.3 (3)
C14—C7—C6—C5	−59.94 (18)	C14—C15—C16—C17	−1.0 (2)
C8—C7—C6—C5	176.84 (13)	C19—C18—C17—C16	0.2 (2)
C23—N4—C22—C26	1.7 (2)	C15—C16—C17—C18	0.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C36—H36A···O2^i	0.98	2.56	3.521 (2)	166

Symmetry code: (i) x, −y+1/2, z−1/2.