10-Methyl-9-phenoxy-carbonyl-acridinium trifluoro-methane-sulfonate monohydrate.

In the crystal structure of the title compound, C(21)H(16)NO(2) (+)·CF(3)SO(3) (-)·H(2)O, the anions and the water mol-ecules are linked by O-H⋯O inter-actions, while the cations form inversion dimers through π-π inter-actions between acridine ring systems. These dimers are linked by C-H⋯O and C-F⋯π inter-actions to adjacent anions, and by C-H⋯π inter-actions to neighboring cations. The water mol-ecule links two H atoms of the cation by C-H⋯O inter-actions and two adjacent anions by O-H⋯O inter-actions. The acridine and benzene ring systems are oriented at 15.6 (1)°. The carboxyl group is twisted at an angle of 77.0 (1)° relative to the acridine skeleton. The mean planes of the adjacent acridine units are either parallel or inclined at an angle of 18.4 (1)°.

Related literature

For background to the chemiluminogenic properties of 9-phenoxy­carbonyl-10-methyl­acridinium trifluoro­meth­ane­sulf­on­ates, see: Brown et al. (2009 ▶); Rak et al. (1999 ▶); Roda et al. (2003 ▶); Zomer & Jacquemijns (2001 ▶). For related structures, see: Sikorski et al. (2007 ▶); Trzybiński et al. (2009 ▶). For inter­molecular inter­actions, see: Bianchi et al. (2004 ▶); Dorn et al. (2005 ▶); Hunter et al. (2001 ▶); Novoa et al. (2006 ▶); Takahashi et al. (2001 ▶). For the synthesis, see: Sato (1996 ▶); Trzybiński et al. (2009 ▶).

Experimental

Crystal data

C21H16NO2 +·CF3SO3 −·H2O

M = 481.44

Monoclinic,

a = 11.3807 (4) Å

b = 9.5785 (2) Å

c = 19.7134 (6) Å

β = 98.172 (3)°

V = 2127.14 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 295 K

0.78 × 0.16 × 0.10 mm

Data collection

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶). T min = 0.741, T max = 1.000

46462 measured reflections

3792 independent reflections

2422 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.211

S = 1.03

3792 reflections

305 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.59 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810009979/ng2742sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009979/ng2742Isup2.hkl

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

C21H16NO2+·CF3SO3−·H2O	F(000) = 992
Mr = 481.44	Dx = 1.503 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 15973 reflections
a = 11.3807 (4) Å	θ = 3.0–29.3°
b = 9.5785 (2) Å	µ = 0.22 mm−1
c = 19.7134 (6) Å	T = 295 K
β = 98.172 (3)°	Needle, yellow
V = 2127.14 (11) Å3	0.78 × 0.16 × 0.10 mm
Z = 4

Oxford Diffraction Gemini R Ultra Ruby CCD diffractometer	3792 independent reflections
Radiation source: Enhanced (Mo) X-ray Source	2422 reflections with I > 2σ(I)
graphite	Rint = 0.060
Detector resolution: 10.4002 pixels mm-1	θmax = 25.1°, θmin = 3.0°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008).	k = −11→11
Tmin = 0.741, Tmax = 1.000	l = −23→23
46462 measured reflections

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.211	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.146P)2] where P = (Fo2 + 2Fc2)/3
3792 reflections	(Δ/σ)max < 0.001
305 parameters	Δρmax = 0.59 e Å−3
3 restraints	Δρmin = −0.39 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.

	x	y	z	Uiso*/Ueq
C1	0.6362 (3)	0.0857 (3)	0.60005 (15)	0.0534 (7)
H1	0.6328	0.1816	0.6067	0.064*
C2	0.7417 (3)	0.0248 (3)	0.59672 (17)	0.0647 (8)
H2	0.8103	0.0788	0.5999	0.078*
C3	0.7481 (3)	−0.1205 (4)	0.58836 (19)	0.0703 (9)
H3	0.8218	−0.1620	0.5877	0.084*
C4	0.6494 (3)	−0.2020 (3)	0.58122 (16)	0.0613 (8)
H4	0.6561	−0.2979	0.5753	0.074*
C5	0.2201 (3)	−0.2410 (3)	0.56540 (18)	0.0700 (10)
H5	0.2234	−0.3363	0.5567	0.084*
C6	0.1149 (4)	−0.1788 (4)	0.5680 (2)	0.0859 (12)
H6	0.0464	−0.2332	0.5615	0.103*
C7	0.1041 (3)	−0.0366 (4)	0.5799 (2)	0.0822 (11)
H7	0.0296	0.0029	0.5805	0.099*
C8	0.2025 (3)	0.0440 (3)	0.59056 (17)	0.0637 (9)
H8	0.1954	0.1389	0.5991	0.076*
C9	0.4195 (3)	0.0648 (2)	0.59775 (13)	0.0450 (7)
N10	0.4351 (2)	−0.2193 (2)	0.57446 (11)	0.0476 (6)
C11	0.5304 (3)	0.0064 (3)	0.59353 (12)	0.0439 (7)
C12	0.5374 (3)	−0.1418 (3)	0.58269 (13)	0.0468 (7)
C13	0.3168 (3)	−0.0151 (3)	0.58886 (14)	0.0493 (7)
C14	0.3255 (3)	−0.1614 (3)	0.57599 (14)	0.0506 (7)
C15	0.4143 (2)	0.2199 (3)	0.61254 (14)	0.0454 (7)
O16	0.4005 (2)	0.24024 (17)	0.67778 (10)	0.0597 (6)
O17	0.4242 (2)	0.30844 (19)	0.57195 (10)	0.0647 (6)
C18	0.4040 (3)	0.3808 (3)	0.70187 (14)	0.0523 (8)
C19	0.3003 (3)	0.4502 (3)	0.70065 (17)	0.0635 (9)
H19	0.2286	0.4080	0.6836	0.076*
C20	0.3034 (4)	0.5869 (4)	0.7257 (2)	0.0763 (11)
H20	0.2335	0.6375	0.7252	0.092*
C21	0.4108 (4)	0.6459 (4)	0.7509 (2)	0.0797 (11)
H21	0.4134	0.7366	0.7679	0.096*
C22	0.5133 (4)	0.5729 (4)	0.7514 (2)	0.0815 (11)
H22	0.5855	0.6142	0.7683	0.098*
C23	0.5108 (3)	0.4375 (3)	0.72675 (17)	0.0669 (9)
H23	0.5805	0.3866	0.7272	0.080*
C24	0.4419 (3)	−0.3729 (3)	0.56256 (17)	0.0637 (9)
H24A	0.3966	−0.4213	0.5928	0.095*
H24B	0.5232	−0.4026	0.5714	0.095*
H24C	0.4102	−0.3937	0.5159	0.095*
O25	0.1330 (4)	0.3806 (6)	0.5581 (2)	0.1480 (15)
H25A	0.136 (7)	0.397 (9)	0.5162 (16)	0.222*
H25B	0.064 (4)	0.350 (10)	0.563 (4)	0.222*
S26	0.15677 (9)	0.55386 (9)	0.38344 (5)	0.0715 (4)
O27	0.1121 (4)	0.4342 (3)	0.41645 (19)	0.1242 (12)
O28	0.0899 (3)	0.6777 (3)	0.38719 (15)	0.0997 (9)
O29	0.2829 (3)	0.5641 (3)	0.39743 (18)	0.1067 (10)
C30	0.1269 (4)	0.5037 (5)	0.2942 (2)	0.0903 (12)
F31	0.1687 (3)	0.6041 (3)	0.25626 (16)	0.1375 (12)
F32	0.0152 (3)	0.4950 (4)	0.27144 (17)	0.1380 (12)
F33	0.1787 (3)	0.3873 (3)	0.28194 (15)	0.1227 (10)

	U11	U22	U33	U12	U13	U23
C1	0.065 (2)	0.0385 (14)	0.0567 (17)	−0.0056 (13)	0.0088 (14)	−0.0035 (12)
C2	0.061 (2)	0.0628 (19)	0.071 (2)	−0.0063 (16)	0.0092 (16)	−0.0077 (15)
C3	0.067 (2)	0.068 (2)	0.076 (2)	0.0102 (18)	0.0113 (17)	−0.0048 (17)
C4	0.078 (2)	0.0434 (16)	0.063 (2)	0.0136 (15)	0.0108 (16)	−0.0023 (13)
C5	0.082 (3)	0.0491 (17)	0.078 (2)	−0.0199 (17)	0.0084 (18)	−0.0067 (15)
C6	0.063 (3)	0.082 (3)	0.111 (3)	−0.027 (2)	0.008 (2)	−0.018 (2)
C7	0.056 (2)	0.086 (3)	0.104 (3)	−0.0065 (19)	0.011 (2)	−0.019 (2)
C8	0.064 (2)	0.0529 (17)	0.074 (2)	−0.0019 (15)	0.0097 (17)	−0.0084 (14)
C9	0.0643 (19)	0.0295 (13)	0.0413 (14)	−0.0039 (12)	0.0074 (13)	−0.0014 (10)
N10	0.0708 (17)	0.0262 (10)	0.0461 (13)	−0.0039 (10)	0.0091 (11)	−0.0018 (8)
C11	0.0603 (18)	0.0320 (13)	0.0392 (14)	−0.0017 (12)	0.0065 (12)	−0.0017 (10)
C12	0.0670 (19)	0.0334 (13)	0.0398 (14)	0.0012 (13)	0.0072 (13)	0.0018 (10)
C13	0.0632 (19)	0.0371 (14)	0.0469 (15)	−0.0020 (13)	0.0058 (13)	−0.0028 (11)
C14	0.066 (2)	0.0377 (14)	0.0481 (16)	−0.0117 (13)	0.0071 (13)	−0.0022 (11)
C15	0.0543 (18)	0.0311 (13)	0.0505 (17)	−0.0011 (11)	0.0071 (13)	−0.0024 (12)
O16	0.0985 (17)	0.0294 (9)	0.0546 (13)	−0.0024 (9)	0.0226 (11)	−0.0024 (8)
O17	0.1108 (19)	0.0318 (10)	0.0544 (12)	−0.0024 (10)	0.0214 (12)	0.0035 (9)
C18	0.082 (2)	0.0329 (14)	0.0457 (15)	−0.0025 (14)	0.0201 (15)	−0.0031 (11)
C19	0.072 (2)	0.0525 (18)	0.069 (2)	−0.0098 (16)	0.0234 (17)	−0.0085 (14)
C20	0.090 (3)	0.0555 (19)	0.091 (3)	0.0138 (18)	0.039 (2)	−0.0100 (17)
C21	0.111 (3)	0.0485 (18)	0.083 (3)	−0.011 (2)	0.026 (2)	−0.0207 (17)
C22	0.099 (3)	0.064 (2)	0.080 (3)	−0.017 (2)	0.010 (2)	−0.0235 (18)
C23	0.077 (2)	0.0539 (18)	0.069 (2)	0.0022 (16)	0.0076 (17)	−0.0084 (15)
C24	0.096 (2)	0.0253 (13)	0.072 (2)	−0.0041 (14)	0.0191 (17)	−0.0056 (12)
O25	0.121 (3)	0.191 (4)	0.130 (3)	0.034 (3)	0.009 (2)	0.014 (3)
S26	0.0867 (8)	0.0584 (5)	0.0688 (6)	−0.0088 (4)	0.0084 (5)	−0.0088 (4)
O27	0.174 (3)	0.092 (2)	0.118 (3)	−0.020 (2)	0.058 (2)	0.0251 (17)
O28	0.133 (3)	0.0679 (16)	0.098 (2)	0.0144 (16)	0.0154 (17)	−0.0183 (14)
O29	0.090 (2)	0.100 (2)	0.119 (2)	−0.0072 (16)	−0.0236 (17)	−0.0098 (17)
C30	0.094 (3)	0.081 (3)	0.092 (3)	0.014 (2)	0.001 (2)	−0.019 (2)
F31	0.192 (3)	0.131 (2)	0.0935 (19)	0.021 (2)	0.034 (2)	0.0265 (16)
F32	0.105 (2)	0.155 (3)	0.138 (2)	0.0063 (18)	−0.0372 (18)	−0.058 (2)
F33	0.161 (3)	0.0951 (18)	0.110 (2)	0.0314 (17)	0.0119 (17)	−0.0364 (14)

C1—C2	1.345 (4)	C15—O17	1.182 (3)
C1—C11	1.414 (4)	C15—O16	1.332 (3)
C1—H1	0.9300	O16—C18	1.426 (3)
C2—C3	1.405 (5)	C18—C19	1.352 (5)
C2—H2	0.9300	C18—C23	1.357 (5)
C3—C4	1.358 (5)	C19—C20	1.398 (5)
C3—H3	0.9300	C19—H19	0.9300
C4—C12	1.404 (4)	C20—C21	1.374 (6)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.345 (5)	C21—C22	1.358 (6)
C5—C14	1.412 (4)	C21—H21	0.9300
C5—H5	0.9300	C22—C23	1.384 (5)
C6—C7	1.391 (5)	C22—H22	0.9300
C6—H6	0.9300	C23—H23	0.9300
C7—C8	1.351 (5)	C24—H24A	0.9600
C7—H7	0.9300	C24—H24B	0.9600
C8—C13	1.424 (4)	C24—H24C	0.9600
C8—H8	0.9300	O25—H25A	0.85 (2)
C9—C13	1.387 (4)	O25—H25B	0.85 (2)
C9—C11	1.393 (4)	S26—O28	1.417 (3)
C9—C15	1.517 (3)	S26—O29	1.426 (3)
N10—C14	1.369 (4)	S26—O27	1.445 (3)
N10—C12	1.371 (4)	S26—C30	1.809 (5)
N10—C24	1.494 (3)	C30—F32	1.290 (5)
C11—C12	1.439 (4)	C30—F33	1.299 (5)
C13—C14	1.430 (4)	C30—F31	1.346 (5)
C2—C1—C11	121.2 (3)	O17—C15—O16	125.8 (2)
C2—C1—H1	119.4	O17—C15—C9	124.2 (2)
C11—C1—H1	119.4	O16—C15—C9	110.0 (2)
C1—C2—C3	119.8 (3)	C15—O16—C18	117.2 (2)
C1—C2—H2	120.1	C19—C18—C23	123.0 (3)
C3—C2—H2	120.1	C19—C18—O16	118.4 (3)
C4—C3—C2	121.8 (3)	C23—C18—O16	118.6 (3)
C4—C3—H3	119.1	C18—C19—C20	118.4 (3)
C2—C3—H3	119.1	C18—C19—H19	120.8
C3—C4—C12	120.1 (3)	C20—C19—H19	120.8
C3—C4—H4	120.0	C21—C20—C19	119.3 (3)
C12—C4—H4	120.0	C21—C20—H20	120.3
C6—C5—C14	119.8 (3)	C19—C20—H20	120.3
C6—C5—H5	120.1	C22—C21—C20	120.6 (3)
C14—C5—H5	120.1	C22—C21—H21	119.7
C5—C6—C7	122.7 (3)	C20—C21—H21	119.7
C5—C6—H6	118.6	C21—C22—C23	120.3 (4)
C7—C6—H6	118.6	C21—C22—H22	119.8
C8—C7—C6	119.7 (4)	C23—C22—H22	119.8
C8—C7—H7	120.2	C18—C23—C22	118.3 (4)
C6—C7—H7	120.2	C18—C23—H23	120.8
C7—C8—C13	120.6 (3)	C22—C23—H23	120.8
C7—C8—H8	119.7	N10—C24—H24A	109.5
C13—C8—H8	119.7	N10—C24—H24B	109.5
C13—C9—C11	121.7 (2)	H24A—C24—H24B	109.5
C13—C9—C15	120.6 (3)	N10—C24—H24C	109.5
C11—C9—C15	117.7 (2)	H24A—C24—H24C	109.5
C14—N10—C12	122.6 (2)	H24B—C24—H24C	109.5
C14—N10—C24	118.1 (2)	H25A—O25—H25B	110 (3)
C12—N10—C24	119.3 (2)	O28—S26—O29	117.75 (19)
C9—C11—C1	123.1 (2)	O28—S26—O27	114.5 (2)
C9—C11—C12	118.3 (2)	O29—S26—O27	112.1 (2)
C1—C11—C12	118.6 (3)	O28—S26—C30	104.19 (19)
N10—C12—C4	122.2 (2)	O29—S26—C30	104.5 (2)
N10—C12—C11	119.2 (3)	O27—S26—C30	101.4 (2)
C4—C12—C11	118.6 (3)	F32—C30—F33	109.3 (4)
C9—C13—C8	122.3 (2)	F32—C30—F31	105.2 (4)
C9—C13—C14	119.0 (3)	F33—C30—F31	107.7 (4)
C8—C13—C14	118.7 (3)	F32—C30—S26	113.3 (3)
N10—C14—C5	122.4 (3)	F33—C30—S26	112.4 (3)
N10—C14—C13	119.2 (2)	F31—C30—S26	108.6 (3)
C5—C14—C13	118.5 (3)
C11—C1—C2—C3	−1.6 (5)	C6—C5—C14—N10	179.5 (3)
C1—C2—C3—C4	2.2 (5)	C6—C5—C14—C13	−0.4 (5)
C2—C3—C4—C12	−0.6 (5)	C9—C13—C14—N10	1.6 (4)
C14—C5—C6—C7	0.9 (6)	C8—C13—C14—N10	−179.8 (3)
C5—C6—C7—C8	−1.1 (7)	C9—C13—C14—C5	−178.5 (3)
C6—C7—C8—C13	0.8 (6)	C8—C13—C14—C5	0.1 (4)
C13—C9—C11—C1	177.8 (3)	C13—C9—C15—O17	−104.9 (4)
C15—C9—C11—C1	−2.2 (4)	C11—C9—C15—O17	75.1 (4)
C13—C9—C11—C12	−2.8 (4)	C13—C9—C15—O16	76.8 (3)
C15—C9—C11—C12	177.2 (2)	C11—C9—C15—O16	−103.2 (3)
C2—C1—C11—C9	178.9 (3)	O17—C15—O16—C18	−3.4 (4)
C2—C1—C11—C12	−0.4 (4)	C9—C15—O16—C18	174.8 (2)
C14—N10—C12—C4	179.8 (3)	C15—O16—C18—C19	94.4 (3)
C24—N10—C12—C4	−0.8 (4)	C15—O16—C18—C23	−87.5 (3)
C14—N10—C12—C11	0.1 (4)	C23—C18—C19—C20	0.5 (5)
C24—N10—C12—C11	179.5 (2)	O16—C18—C19—C20	178.6 (3)
C3—C4—C12—N10	178.8 (3)	C18—C19—C20—C21	−0.4 (5)
C3—C4—C12—C11	−1.5 (4)	C19—C20—C21—C22	0.4 (6)
C9—C11—C12—N10	2.3 (3)	C20—C21—C22—C23	−0.4 (6)
C1—C11—C12—N10	−178.3 (2)	C19—C18—C23—C22	−0.6 (5)
C9—C11—C12—C4	−177.4 (2)	O16—C18—C23—C22	−178.7 (3)
C1—C11—C12—C4	2.0 (4)	C21—C22—C23—C18	0.5 (6)
C11—C9—C13—C8	−177.7 (3)	O28—S26—C30—F32	−53.1 (4)
C15—C9—C13—C8	2.3 (4)	O29—S26—C30—F32	−177.2 (3)
C11—C9—C13—C14	0.9 (4)	O27—S26—C30—F32	66.1 (4)
C15—C9—C13—C14	−179.1 (2)	O28—S26—C30—F33	−177.6 (3)
C7—C8—C13—C9	178.3 (3)	O29—S26—C30—F33	58.2 (4)
C7—C8—C13—C14	−0.3 (5)	O27—S26—C30—F33	−58.5 (4)
C12—N10—C14—C5	178.0 (3)	O28—S26—C30—F31	63.3 (4)
C24—N10—C14—C5	−1.3 (4)	O29—S26—C30—F31	−60.8 (3)
C12—N10—C14—C13	−2.1 (4)	O27—S26—C30—F31	−177.5 (3)
C24—N10—C14—C13	178.6 (2)

Cg4 is the centroid of the C18–C23 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O28i	0.93	2.59	3.424 (4)	149
C8—H8···O25	0.93	2.52	3.360 (6)	150
C19—H19···O25	0.93	2.57	3.232 (5)	129
C24—H24A···Cg4ii	0.96	2.69	3.484 (4)	140
C24—H24C···O29ii	0.96	2.60	3.544 (5)	168
O25—H25A···O27	0.85 (4)	1.98 (3)	2.816 (5)	170 (8)
O25—H25B···O28iii	0.86 (4)	2.14 (6)	2.948 (6)	156 (7)

X—I···J	I···J	X···J	X—I···J
C30—F31···Cg2iv	3.269 (3)	4.075 (4)	117.8 (2)
C30—F32···Cg1iv	3.744 (3)	4.463 (4)	116.1 (3)

I	J	CgI···CgJ	Dihedral angle	CgI_Perp	CgI_Offset
1	2v	3.682 (2)	1.92 (1)	3.568 (1)	0.909 (1)
2	1v	3.682 (2)	1.92 (1)	3.591 (1)	0.814 (1)

Table 1

Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C18–C23 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O28i	0.93	2.59	3.424 (4)	149
C8—H8⋯O25	0.93	2.52	3.360 (6)	150
C19—H19⋯O25	0.93	2.57	3.232 (5)	129
C24—H24A⋯Cg4ii	0.96	2.69	3.484 (4)	140
C24—H24C⋯O29ii	0.96	2.60	3.544 (5)	168
O25—H25A⋯O27	0.85 (4)	1.98 (3)	2.816 (5)	170 (8)
O25—H25B⋯O28iii	0.86 (4)	2.14 (6)	2.948 (6)	156 (7)

Symmetry codes: (i) ; (ii) ; (iii) .

Table 2

C—F⋯π inter­actions (Å, °)

Cg1 and Cg2 are the centroids of the C9/N10/C11–C14 and C1–C4/C11/C12 rings, respectively.

X—I⋯J	I⋯J	X⋯J	X—I⋯J
C30—F31⋯Cg2iv	3.269 (3)	4.075 (4)	117.8 (2)
C30—F32⋯Cg1iv	3.744 (3)	4.463 (4)	116.1 (3)

Symmetry code: (iv) .

Table 3

π–π inter­actions (Å, °)

Cg1 and Cg2 are the centroids of the C9/N10/C11–C14 and C1–C4/C11/C12 rings, respectively. CgI⋯CgJ is the distance between ring centroids. The dihedral angle is that between the planes of the rings I and J. CgI_Perp is the perpendicular distance of CgI from ring J. CgI_Offset is the distance between CgI and the perpendicular projection of CgJ on ring I.

I	J	CgI⋯CgJ	Dihedral angle	CgI_Perp	CgI_Offset
1	2v	3.682 (2)	1.92 (1)	3.568 (1)	0.909 (1)
2	1v	3.682 (2)	1.92 (1)	3.591 (1)	0.814 (1)

Symmetry code: (v) −x + 1, −y, −z + 1.