Crystal structure of 10-[(3-oxo-3H-benzo[f]chromen-1-yl)meth-yl]-2-tri-fluoro-methyl-9a,10-di-hydro-benz[4,5]imidazo[1,2-a]pyrimidin-4(5aH)-one.

In the title compound, C25H14F3N3O3, the dihedral angle between the planes of the benz[4,5]imidazo[1,2-a]pyrimidine unit (r.m.s. deviation = 0.035 Å) and the benzochromene ring system (r.m.s. deviation = 0.106 Å) is 72.82 (5)°. In the crystal, mol-ecules are linked by C-H⋯O inter-actions, generating [010] C(9) chains. A weak aromatic π-π stacking inter-action [centroid-centroid separation = 3.5376 (15) Å] is also observed.

Related literature

For background to benzo­pyrimidine derivatives, see: Bodke et al. (2003 ▸); Moneam et al. (2004 ▸). For the synthesis of the title compound, see: Puttaraju et al. (2013 ▸). For a related structure, see: Chandra et al. (2013 ▸).

Experimental

Crystal data

C25H14F3N3O3

M = 461.39

Monoclinic,

a = 9.7665 (5) Å

b = 7.7950 (4) Å

c = 27.0602 (16) Å

β = 95.186 (5)°

V = 2051.66 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

9209 measured reflections

5020 independent reflections

2637 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.176

S = 1.00

5020 reflections

308 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.19 e Å−3

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015014425/hb7467sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015014425/hb7467Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015014425/hb7467Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015014425/hb7467fig1.tif

Perspective diagram of the mol­ecule with 50% probability displacement ellipsoids.

Click here for additional data file.

b . DOI: 10.1107/S2056989015014425/hb7467fig2.tif

Packing diagram of the mol­ecule viewed down the b axis.

CCDC reference: 1416062

Additional supporting information: crystallographic information; 3D view; checkCIF report

C25H14F3N3O3	F(000) = 944
Mr = 461.39	Dx = 1.494 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5020 reflections
a = 9.7665 (5) Å	θ = 2.7–28.3°
b = 7.7950 (4) Å	µ = 0.12 mm−1
c = 27.0602 (16) Å	T = 293 K
β = 95.186 (5)°	Bolck, yellow
V = 2051.66 (19) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	Rint = 0.033
ω and φ scans	θmax = 28.3°, θmin = 2.7°
9209 measured reflections	h = −11→12
5020 independent reflections	k = −5→10
2637 reflections with I > 2σ(I)	l = −27→36

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)] = 0.057	H-atom parameters constrained
wR(F2) = 0.176	w = 1/[σ2(Fo2) + (0.0676P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
5020 reflections	Δρmax = 0.21 e Å−3
308 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXL, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0030 (8)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
F16	−0.06281 (18)	0.8341 (3)	0.10659 (8)	0.1073 (9)
F17	−0.01199 (16)	0.6009 (3)	0.07308 (6)	0.0921 (8)
F18	−0.14200 (15)	0.5991 (3)	0.13215 (7)	0.1024 (9)
O11	0.20544 (19)	0.5442 (3)	0.27911 (6)	0.0737 (8)
O23	0.4824 (2)	1.3933 (2)	0.15054 (8)	0.0862 (9)
O24	0.62445 (19)	1.3111 (2)	0.09616 (7)	0.0628 (7)
N1	0.31775 (19)	0.6564 (2)	0.21634 (7)	0.0455 (6)
N3	0.44740 (17)	0.7624 (2)	0.16034 (6)	0.0409 (6)
N14	0.21121 (18)	0.7121 (2)	0.13481 (7)	0.0463 (6)
C2	0.3181 (2)	0.7104 (3)	0.16781 (8)	0.0410 (7)
C4	0.5313 (2)	0.7441 (3)	0.20479 (8)	0.0447 (7)
C5	0.4513 (2)	0.6770 (3)	0.24038 (9)	0.0478 (8)
C6	0.5044 (3)	0.6466 (3)	0.28881 (9)	0.0618 (9)
C7	0.6405 (3)	0.6880 (4)	0.29999 (10)	0.0739 (11)
C8	0.7211 (3)	0.7556 (4)	0.26516 (11)	0.0725 (11)
C9	0.6678 (2)	0.7831 (3)	0.21638 (10)	0.0592 (9)
C10	0.1990 (3)	0.5950 (3)	0.23595 (9)	0.0545 (8)
C12	0.0819 (3)	0.6013 (3)	0.20043 (9)	0.0587 (9)
C13	0.0939 (2)	0.6575 (3)	0.15344 (9)	0.0515 (8)
C15	−0.0306 (3)	0.6693 (4)	0.11661 (10)	0.0623 (10)
C19	0.4956 (2)	0.7898 (3)	0.11163 (8)	0.0424 (7)
C20	0.5353 (2)	0.9744 (3)	0.10211 (8)	0.0402 (7)
C21	0.4909 (2)	1.0969 (3)	0.13174 (9)	0.0511 (8)
C22	0.5260 (3)	1.2748 (3)	0.12793 (10)	0.0608 (10)
C25	0.6706 (3)	1.1898 (3)	0.06486 (9)	0.0538 (8)
C26	0.6241 (2)	1.0222 (3)	0.06349 (8)	0.0418 (7)
C27	0.6713 (2)	0.9122 (3)	0.02498 (8)	0.0461 (7)
C28	0.7704 (2)	0.9786 (4)	−0.00588 (9)	0.0598 (9)
C29	0.8182 (3)	1.1485 (4)	0.00084 (11)	0.0763 (11)
C30	0.7689 (3)	1.2528 (4)	0.03478 (11)	0.0730 (11)
C31	0.8178 (3)	0.8749 (5)	−0.04365 (11)	0.0803 (13)
C32	0.7698 (3)	0.7147 (5)	−0.05239 (11)	0.0787 (13)
C33	0.6709 (3)	0.6507 (4)	−0.02363 (10)	0.0682 (10)
C34	0.6220 (3)	0.7459 (3)	0.01357 (9)	0.0536 (8)
H6	0.45110	0.60090	0.31240	0.0740*
H7	0.67990	0.66990	0.33210	0.0890*
H8	0.81240	0.78320	0.27460	0.0870*
H9	0.72200	0.82580	0.19270	0.0710*
H12	−0.00350	0.56670	0.20950	0.0700*
H19A	0.42380	0.75540	0.08650	0.0510*
H19B	0.57470	0.71680	0.10830	0.0510*
H21	0.43440	1.06460	0.15600	0.0610*
H29	0.88510	1.18930	−0.01850	0.0920*
H30	0.79970	1.36540	0.03820	0.0880*
H31	0.88380	0.91840	−0.06300	0.0960*
H32	0.80250	0.64810	−0.07730	0.0950*
H33	0.63690	0.54050	−0.02970	0.0820*
H34	0.55460	0.69940	0.03170	0.0640*

	U11	U22	U33	U12	U13	U23
F16	0.0900 (14)	0.0943 (15)	0.1297 (18)	0.0138 (11)	−0.0336 (12)	0.0102 (13)
F17	0.0675 (10)	0.1379 (17)	0.0697 (11)	−0.0180 (11)	−0.0005 (8)	−0.0251 (11)
F18	0.0503 (10)	0.1613 (19)	0.0968 (14)	−0.0305 (11)	0.0128 (9)	0.0081 (13)
O11	0.0810 (13)	0.0911 (15)	0.0517 (11)	−0.0130 (11)	0.0211 (9)	0.0169 (11)
O23	0.1251 (18)	0.0480 (11)	0.0847 (15)	0.0111 (11)	0.0045 (13)	−0.0181 (11)
O24	0.0774 (13)	0.0432 (9)	0.0664 (12)	−0.0115 (9)	−0.0012 (10)	0.0027 (9)
N1	0.0509 (11)	0.0471 (11)	0.0396 (10)	−0.0036 (9)	0.0106 (8)	0.0015 (9)
N3	0.0404 (10)	0.0434 (10)	0.0397 (10)	−0.0047 (9)	0.0083 (7)	−0.0002 (9)
N14	0.0429 (10)	0.0540 (12)	0.0426 (10)	−0.0056 (10)	0.0078 (8)	0.0004 (10)
C2	0.0463 (13)	0.0375 (12)	0.0402 (12)	−0.0020 (10)	0.0101 (9)	−0.0008 (10)
C4	0.0462 (13)	0.0448 (13)	0.0435 (12)	0.0003 (11)	0.0068 (10)	−0.0018 (11)
C5	0.0510 (14)	0.0490 (14)	0.0434 (12)	0.0005 (12)	0.0048 (10)	−0.0012 (12)
C6	0.0688 (17)	0.0678 (18)	0.0484 (14)	0.0022 (14)	0.0038 (12)	0.0029 (14)
C7	0.076 (2)	0.090 (2)	0.0520 (16)	0.0069 (17)	−0.0137 (14)	0.0015 (16)
C8	0.0582 (17)	0.086 (2)	0.0704 (19)	0.0014 (16)	−0.0095 (14)	−0.0032 (17)
C9	0.0480 (14)	0.0681 (17)	0.0612 (16)	−0.0014 (13)	0.0038 (12)	−0.0014 (15)
C10	0.0614 (15)	0.0549 (15)	0.0502 (14)	−0.0069 (13)	0.0210 (12)	0.0048 (13)
C12	0.0488 (14)	0.0646 (17)	0.0651 (17)	−0.0092 (13)	0.0189 (12)	0.0038 (14)
C13	0.0443 (13)	0.0544 (15)	0.0574 (15)	−0.0057 (12)	0.0136 (11)	0.0026 (13)
C15	0.0518 (16)	0.076 (2)	0.0597 (17)	−0.0108 (15)	0.0080 (12)	−0.0019 (16)
C19	0.0450 (12)	0.0405 (12)	0.0434 (12)	−0.0041 (10)	0.0128 (9)	−0.0030 (10)
C20	0.0414 (12)	0.0378 (11)	0.0409 (11)	−0.0025 (10)	0.0016 (9)	0.0000 (10)
C21	0.0587 (15)	0.0443 (13)	0.0506 (14)	0.0006 (12)	0.0070 (11)	−0.0034 (12)
C22	0.0789 (19)	0.0460 (15)	0.0558 (16)	0.0076 (14)	−0.0039 (14)	−0.0056 (13)
C25	0.0565 (15)	0.0501 (14)	0.0531 (14)	−0.0076 (12)	−0.0043 (11)	0.0045 (13)
C26	0.0403 (11)	0.0460 (13)	0.0384 (11)	−0.0023 (10)	0.0006 (9)	0.0052 (10)
C27	0.0388 (11)	0.0601 (15)	0.0391 (11)	0.0036 (11)	0.0018 (9)	0.0043 (12)
C28	0.0456 (14)	0.085 (2)	0.0498 (14)	−0.0011 (14)	0.0095 (11)	0.0087 (15)
C29	0.0701 (19)	0.097 (2)	0.0637 (19)	−0.0268 (18)	0.0162 (15)	0.0151 (18)
C30	0.0746 (19)	0.0704 (19)	0.0729 (19)	−0.0324 (16)	0.0013 (15)	0.0196 (17)
C31	0.0624 (18)	0.122 (3)	0.0605 (18)	0.006 (2)	0.0279 (14)	0.005 (2)
C32	0.077 (2)	0.108 (3)	0.0533 (17)	0.024 (2)	0.0178 (15)	−0.0043 (19)
C33	0.081 (2)	0.0726 (19)	0.0519 (15)	0.0111 (15)	0.0106 (14)	−0.0084 (15)
C34	0.0634 (15)	0.0552 (15)	0.0435 (13)	−0.0026 (13)	0.0115 (11)	−0.0066 (12)

F16—C15	1.344 (4)	C21—C22	1.434 (3)
F17—C15	1.320 (3)	C25—C26	1.383 (3)
F18—C15	1.320 (3)	C25—C30	1.402 (4)
O11—C10	1.229 (3)	C26—C27	1.456 (3)
O23—C22	1.207 (3)	C27—C28	1.431 (3)
O24—C22	1.376 (3)	C27—C34	1.407 (3)
O24—C25	1.372 (3)	C28—C29	1.411 (4)
N1—C2	1.379 (3)	C28—C31	1.414 (4)
N1—C5	1.413 (3)	C29—C30	1.348 (4)
N1—C10	1.403 (3)	C31—C32	1.347 (5)
N3—C2	1.359 (3)	C32—C33	1.387 (4)
N3—C4	1.400 (3)	C33—C34	1.371 (4)
N3—C19	1.455 (3)	C6—H6	0.9300
N14—C2	1.311 (3)	C7—H7	0.9300
N14—C13	1.361 (3)	C8—H8	0.9300
C4—C5	1.396 (3)	C9—H9	0.9300
C4—C9	1.376 (3)	C12—H12	0.9300
C5—C6	1.386 (3)	C19—H19A	0.9700
C6—C7	1.375 (4)	C19—H19B	0.9700
C7—C8	1.386 (4)	C21—H21	0.9300
C8—C9	1.391 (4)	C29—H29	0.9300
C10—C12	1.427 (4)	C30—H30	0.9300
C12—C13	1.360 (3)	C31—H31	0.9300
C13—C15	1.504 (4)	C32—H32	0.9300
C19—C20	1.518 (3)	C33—H33	0.9300
C20—C21	1.344 (3)	C34—H34	0.9300
C20—C26	1.465 (3)
F16···N14	2.878 (3)	C32···C22iii	3.386 (4)
F16···C27i	3.310 (3)	C32···C21iii	3.502 (4)
F17···N14	2.763 (2)	C33···C22iii	3.320 (4)
F17···H30ii	2.7100	C33···O24iii	3.352 (3)
F17···H29iii	2.5900	C33···C30viii	3.572 (4)
F17···H32iv	2.8100	C34···C19	3.045 (3)
F18···H9i	2.8200	C34···C25iii	3.439 (4)
F18···H12	2.4000	C34···C26iii	3.534 (3)
O11···C6	3.015 (3)	C2···H21	3.0100
O11···C2v	2.991 (3)	C4···H21	2.9400
O11···N1v	3.035 (3)	C9···H19B	3.0300
O11···N3v	3.191 (3)	C10···H6	3.0700
O11···C21v	3.241 (3)	C19···H9	2.9800
O11···C4v	3.345 (3)	C19···H34	2.3900
O11···C5v	3.266 (3)	C20···H34	2.8900
O23···N3vi	2.912 (2)	C22···H7vii	3.0900
O23···C2vi	3.006 (3)	C22···H8vii	2.9500
O23···N1vi	3.237 (3)	C25···H7vii	3.0300
O23···C5vi	3.321 (3)	C27···H19B	2.9500
O23···C19vi	3.271 (3)	C30···H33vi	3.0500
O23···C4vi	3.120 (3)	C33···H30viii	2.9900
O24···C33iii	3.352 (3)	C34···H19B	2.6600
O11···H6	2.5200	C34···H19A	2.8900
O11···H21v	2.3300	H6···O11	2.5200
O23···H8vii	2.8500	H6···C10	3.0700
O24···H7vii	2.8200	H7···O24xi	2.8200
N1···O23viii	3.237 (3)	H7···C22xi	3.0900
N1···O11ix	3.035 (3)	H7···C25xi	3.0300
N3···O23viii	2.912 (2)	H8···O23xi	2.8500
N3···O11ix	3.191 (3)	H8···C22xi	2.9500
N14···F17	2.763 (2)	H9···F18x	2.8200
N14···F16	2.878 (3)	H9···C19	2.9800
N3···H21	2.3600	H12···F18	2.4000
N14···H19A	2.5700	H19A···N14	2.5700
C2···O23viii	3.006 (3)	H19A···C34	2.8900
C2···O11ix	2.991 (3)	H19A···H34	2.0900
C4···C21	3.389 (3)	H19B···C9	3.0300
C4···O23viii	3.120 (3)	H19B···C27	2.9500
C4···O11ix	3.345 (3)	H19B···C34	2.6600
C5···O11ix	3.266 (3)	H19B···H34	2.0700
C5···O23viii	3.321 (3)	H21···N3	2.3600
C6···O11	3.015 (3)	H21···C2	3.0100
C9···C20	3.569 (3)	H21···C4	2.9400
C19···C34	3.045 (3)	H21···O11ix	2.3300
C19···O23viii	3.271 (3)	H29···H31	2.4300
C20···C9	3.569 (3)	H29···F17iii	2.5900
C21···O11ix	3.241 (3)	H30···F17xii	2.7100
C21···C4	3.389 (3)	H30···C33vi	2.9900
C21···C32iii	3.502 (4)	H31···H29	2.4300
C22···C33iii	3.320 (4)	H32···F17iv	2.8100
C22···C32iii	3.386 (4)	H33···C30viii	3.0500
C25···C34iii	3.439 (4)	H34···C19	2.3900
C26···C34iii	3.534 (3)	H34···C20	2.8900
C27···F16x	3.310 (3)	H34···H19A	2.0900
C30···C33vi	3.572 (4)	H34···H19B	2.0700
C22—O24—C25	122.07 (19)	C20—C26—C25	115.8 (2)
C2—N1—C5	108.78 (18)	C20—C26—C27	127.4 (2)
C2—N1—C10	122.53 (19)	C25—C26—C27	116.8 (2)
C5—N1—C10	128.7 (2)	C26—C27—C28	118.6 (2)
C2—N3—C4	108.75 (17)	C26—C27—C34	125.1 (2)
C2—N3—C19	124.04 (17)	C28—C27—C34	116.2 (2)
C4—N3—C19	125.53 (16)	C27—C28—C29	119.9 (2)
C2—N14—C13	112.93 (19)	C27—C28—C31	119.9 (3)
N1—C2—N3	108.36 (17)	C29—C28—C31	120.3 (2)
N1—C2—N14	125.54 (19)	C28—C29—C30	121.3 (3)
N3—C2—N14	126.1 (2)	C25—C30—C29	119.3 (3)
N3—C4—C5	108.08 (17)	C28—C31—C32	121.7 (3)
N3—C4—C9	130.8 (2)	C31—C32—C33	118.9 (3)
C5—C4—C9	121.1 (2)	C32—C33—C34	121.6 (3)
N1—C5—C4	106.02 (19)	C27—C34—C33	121.7 (2)
N1—C5—C6	131.8 (2)	C5—C6—H6	122.00
C4—C5—C6	122.1 (2)	C7—C6—H6	122.00
C5—C6—C7	116.1 (2)	C6—C7—H7	119.00
C6—C7—C8	122.5 (3)	C8—C7—H7	119.00
C7—C8—C9	121.1 (3)	C7—C8—H8	119.00
C4—C9—C8	117.0 (2)	C9—C8—H8	119.00
O11—C10—N1	119.8 (2)	C4—C9—H9	122.00
O11—C10—C12	128.3 (3)	C8—C9—H9	121.00
N1—C10—C12	111.9 (2)	C10—C12—H12	120.00
C10—C12—C13	120.6 (2)	C13—C12—H12	120.00
N14—C13—C12	126.4 (2)	N3—C19—H19A	109.00
N14—C13—C15	113.1 (2)	N3—C19—H19B	109.00
C12—C13—C15	120.4 (2)	C20—C19—H19A	109.00
F16—C15—F17	104.7 (2)	C20—C19—H19B	109.00
F16—C15—F18	106.0 (2)	H19A—C19—H19B	108.00
F16—C15—C13	110.7 (2)	C20—C21—H21	118.00
F17—C15—F18	107.5 (2)	C22—C21—H21	118.00
F17—C15—C13	113.5 (2)	C28—C29—H29	119.00
F18—C15—C13	113.8 (2)	C30—C29—H29	119.00
N3—C19—C20	113.66 (18)	C25—C30—H30	120.00
C19—C20—C21	118.11 (19)	C29—C30—H30	120.00
C19—C20—C26	122.60 (19)	C28—C31—H31	119.00
C21—C20—C26	119.3 (2)	C32—C31—H31	119.00
C20—C21—C22	123.5 (2)	C31—C32—H32	121.00
O23—C22—O24	117.3 (2)	C33—C32—H32	121.00
O23—C22—C21	127.3 (3)	C32—C33—H33	119.00
O24—C22—C21	115.4 (2)	C34—C33—H33	119.00
O24—C25—C26	122.8 (2)	C27—C34—H34	119.00
O24—C25—C30	113.4 (2)	C33—C34—H34	119.00
C26—C25—C30	123.8 (2)
C22—O24—C25—C30	178.8 (2)	C10—C12—C13—C15	−178.0 (2)
C25—O24—C22—O23	−173.1 (2)	C10—C12—C13—N14	0.0 (4)
C25—O24—C22—C21	9.3 (3)	N14—C13—C15—F16	−68.0 (3)
C22—O24—C25—C26	−1.3 (4)	C12—C13—C15—F18	−9.0 (4)
C5—N1—C2—N14	−178.9 (2)	N14—C13—C15—F17	49.4 (3)
C10—N1—C2—N3	179.82 (18)	N14—C13—C15—F18	172.8 (2)
C10—N1—C2—N14	0.3 (3)	C12—C13—C15—F16	110.3 (3)
C5—N1—C2—N3	0.7 (2)	C12—C13—C15—F17	−132.3 (3)
C2—N1—C10—O11	178.1 (2)	N3—C19—C20—C26	160.66 (18)
C2—N1—C10—C12	−1.9 (3)	N3—C19—C20—C21	−16.8 (3)
C5—N1—C10—O11	−3.0 (4)	C19—C20—C21—C22	177.3 (2)
C2—N1—C5—C4	−0.2 (2)	C21—C20—C26—C27	−173.5 (2)
C2—N1—C5—C6	178.2 (2)	C19—C20—C26—C25	−169.1 (2)
C10—N1—C5—C4	−179.3 (2)	C19—C20—C26—C27	9.1 (3)
C10—N1—C5—C6	−0.9 (4)	C26—C20—C21—C22	−0.2 (3)
C5—N1—C10—C12	177.1 (2)	C21—C20—C26—C25	8.3 (3)
C19—N3—C2—N14	−15.4 (3)	C20—C21—C22—O23	174.1 (3)
C2—N3—C4—C9	−178.1 (2)	C20—C21—C22—O24	−8.6 (4)
C19—N3—C4—C5	−164.93 (19)	O24—C25—C26—C20	−7.7 (3)
C2—N3—C4—C5	0.7 (2)	O24—C25—C26—C27	173.9 (2)
C2—N3—C19—C20	116.5 (2)	C30—C25—C26—C20	172.2 (2)
C4—N3—C19—C20	−80.0 (2)	C30—C25—C26—C27	−6.2 (4)
C19—N3—C2—N1	165.06 (18)	O24—C25—C30—C29	−177.2 (3)
C19—N3—C4—C9	16.2 (4)	C26—C25—C30—C29	2.9 (4)
C4—N3—C2—N1	−0.8 (2)	C20—C26—C27—C28	−173.0 (2)
C4—N3—C2—N14	178.7 (2)	C20—C26—C27—C34	10.4 (4)
C13—N14—C2—N3	−178.0 (2)	C25—C26—C27—C28	5.2 (3)
C2—N14—C13—C12	−1.6 (3)	C25—C26—C27—C34	−171.4 (2)
C2—N14—C13—C15	176.5 (2)	C26—C27—C28—C29	−1.2 (3)
C13—N14—C2—N1	1.5 (3)	C26—C27—C28—C31	−179.8 (2)
N3—C4—C9—C8	177.6 (2)	C34—C27—C28—C29	175.7 (2)
C5—C4—C9—C8	−1.2 (4)	C34—C27—C28—C31	−2.9 (3)
N3—C4—C5—N1	−0.3 (2)	C26—C27—C34—C33	179.4 (2)
N3—C4—C5—C6	−178.9 (2)	C28—C27—C34—C33	2.7 (4)
C9—C4—C5—N1	178.7 (2)	C27—C28—C29—C30	−2.3 (4)
C9—C4—C5—C6	0.1 (4)	C31—C28—C29—C30	176.3 (3)
C4—C5—C6—C7	0.6 (4)	C27—C28—C31—C32	1.5 (4)
N1—C5—C6—C7	−177.6 (2)	C29—C28—C31—C32	−177.1 (3)
C5—C6—C7—C8	−0.3 (4)	C28—C29—C30—C25	1.6 (4)
C6—C7—C8—C9	−0.8 (5)	C28—C31—C32—C33	0.3 (5)
C7—C8—C9—C4	1.5 (4)	C31—C32—C33—C34	−0.5 (5)
O11—C10—C12—C13	−178.2 (3)	C32—C33—C34—C27	−1.1 (4)
N1—C10—C12—C13	1.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O11ix	0.93	2.33	3.241 (3)	168

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C21H21O11i	0.93	2.33	3.241(3)	168

Symmetry code: (i) .