9-Benzyl-9H-carbazole.

The asymmetric unit of the title compound, C(19)H(15)N, contains two crystallographically independent mol-ecules. In both mol-ecules, the planar carbazole moieties [maximum deviations = 0.037 (4) and 0.042 (3) Å] are oriented with respect to the adjacent benzene rings, at dihedral angles of 85.29 (8) and 89.89 (7)°, respectively. In the crystal structure, weak C-H⋯π inter-actions are observed involving the carbazole rings.

Related literature

For tetra­hydro­carbazole systems present in the framework of a number of indole-type alkaloids of biological inter­est, see: Phillipson & Zenk (1980 ▶); Saxton (1983 ▶); Abraham (1975 ▶). For related structures, see: Hökelek et al. (1994 ▶, 1998 ▶, 1999 ▶, 2004 ▶, 2006 ▶); Patır et al. (1997 ▶); Hökelek & Patır (1999 ▶, 2002 ▶); Çaylak et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C19H15N

M = 257.32

Monoclinic,

a = 14.9305 (4) Å

b = 5.5612 (2) Å

c = 32.7916 (8) Å

β = 94.518 (3)°

V = 2714.27 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.07 mm−1

T = 100 K

0.27 × 0.15 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.981, T max = 0.990

24870 measured reflections

6816 independent reflections

3384 reflections with I > 2σ(I)

R int = 0.103

Refinement

R[F 2 > 2σ(F 2)] = 0.076

wR(F 2) = 0.210

S = 1.03

6816 reflections

474 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810012444/xu2745sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012444/xu2745Isup2.hkl

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

C19H15N	F(000) = 1088
Mr = 257.32	Dx = 1.259 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1669 reflections
a = 14.9305 (4) Å	θ = 2.5–22.9°
b = 5.5612 (2) Å	µ = 0.07 mm−1
c = 32.7916 (8) Å	T = 100 K
β = 94.518 (3)°	Block, colorless
V = 2714.27 (14) Å3	0.27 × 0.15 × 0.14 mm
Z = 8

Bruker Kappa APEXII CCD area-detector diffractometer	6816 independent reflections
Radiation source: fine-focus sealed tube	3384 reflections with I > 2σ(I)
graphite	Rint = 0.103
φ and ω scans	θmax = 28.4°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −19→18
Tmin = 0.981, Tmax = 0.990	k = −7→7
24870 measured reflections	l = −42→43

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)] = 0.076	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.210	w = 1/[σ2(Fo2) + (0.0918P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
6816 reflections	Δρmax = 0.27 e Å−3
474 parameters	Δρmin = −0.26 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0068 (11)

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.

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.

	x	y	z	Uiso*/Ueq
C1	0.5696 (2)	0.6160 (7)	0.83884 (11)	0.0399 (9)
H1	0.536 (2)	0.451 (6)	0.8446 (9)	0.042 (9)*
C2	0.5654 (2)	0.7192 (8)	0.80036 (11)	0.0495 (10)
H2	0.524 (2)	0.643 (6)	0.7769 (10)	0.040 (9)*
C3	0.6133 (2)	0.9241 (8)	0.79216 (10)	0.0486 (10)
H3	0.6077	0.9890	0.7659	0.058*
C4	0.6692 (2)	1.0341 (7)	0.82209 (10)	0.0364 (8)
H4	0.702 (2)	1.169 (6)	0.8155 (9)	0.030 (9)*
C4A	0.67613 (19)	0.9336 (6)	0.86118 (9)	0.0286 (7)
C5	0.7898 (2)	1.1740 (6)	0.91002 (10)	0.0286 (7)
H5	0.807 (2)	1.303 (6)	0.8898 (10)	0.052 (10)*
C5A	0.72814 (19)	0.9919 (5)	0.89881 (8)	0.0244 (6)
C6	0.8284 (2)	1.1795 (6)	0.94938 (10)	0.0308 (7)
H6	0.870 (2)	1.308 (6)	0.9577 (9)	0.045 (10)*
C7	0.8064 (2)	1.0064 (6)	0.97798 (10)	0.0294 (7)
H7	0.836 (2)	1.010 (6)	1.0055 (10)	0.037 (9)*
C8	0.7450 (2)	0.8268 (6)	0.96804 (9)	0.0284 (7)
H8	0.727 (2)	0.696 (6)	0.9883 (10)	0.045 (9)*
C8A	0.70640 (19)	0.8208 (5)	0.92781 (9)	0.0243 (6)
N9	0.64413 (16)	0.6597 (4)	0.90964 (7)	0.0263 (6)
C9A	0.62622 (19)	0.7261 (5)	0.86924 (9)	0.0274 (7)
C10	0.5991 (2)	0.4654 (6)	0.92981 (11)	0.0314 (7)
H10A	0.604 (2)	0.313 (6)	0.9142 (9)	0.036 (9)*
H10B	0.632 (2)	0.433 (5)	0.9553 (9)	0.031 (9)*
C11	0.50251 (19)	0.5224 (5)	0.93644 (9)	0.0260 (7)
C12	0.4798 (2)	0.7304 (6)	0.95693 (10)	0.0335 (8)
H12	0.527 (2)	0.852 (6)	0.9672 (10)	0.048 (10)*
C13	0.3908 (2)	0.7795 (6)	0.96297 (10)	0.0348 (8)
H13	0.375 (2)	0.931 (6)	0.9762 (10)	0.052 (10)*
C14	0.3239 (2)	0.6231 (6)	0.94863 (9)	0.0311 (7)
H14	0.263 (3)	0.675 (6)	0.9533 (10)	0.054 (11)*
C15	0.3458 (2)	0.4166 (6)	0.92833 (10)	0.0337 (8)
H15	0.296 (2)	0.295 (6)	0.9180 (9)	0.038 (9)*
C16	0.4348 (2)	0.3666 (6)	0.92232 (10)	0.0305 (7)
H16	0.4532 (19)	0.217 (5)	0.9088 (8)	0.027 (8)*
C1'	0.9099 (2)	0.8115 (6)	0.57706 (9)	0.0291 (7)
H1'	0.865 (2)	0.673 (5)	0.5719 (8)	0.032 (8)*
C2'	0.9229 (2)	0.9787 (6)	0.54711 (10)	0.0333 (8)
H2'	0.883 (2)	0.951 (5)	0.5217 (9)	0.029 (8)*
C3'	0.9879 (2)	1.1600 (6)	0.55305 (10)	0.0345 (8)
H3'	0.998 (2)	1.271 (6)	0.5318 (9)	0.035 (9)*
C4'	1.0415 (2)	1.1763 (6)	0.58923 (10)	0.0294 (7)
H4'	1.085 (3)	1.310 (7)	0.5918 (11)	0.063 (12)*
C4A'	1.02988 (19)	1.0096 (5)	0.61992 (9)	0.0258 (7)
C5'	1.1437 (2)	1.0841 (6)	0.68366 (10)	0.0325 (8)
H5'	1.177 (2)	1.222 (6)	0.6724 (9)	0.041 (9)*
C5A'	1.07331 (19)	0.9688 (5)	0.66042 (9)	0.0258 (7)
C6'	1.1713 (2)	0.9928 (7)	0.72151 (10)	0.0399 (8)
H6'	1.223 (3)	1.067 (7)	0.7361 (11)	0.061 (11)*
C7'	1.1302 (2)	0.7899 (6)	0.73662 (9)	0.0374 (8)
H7'	1.1509	0.7306	0.7622	0.045*
C8'	1.0594 (2)	0.6735 (6)	0.71486 (9)	0.0305 (7)
H8'	1.028 (2)	0.519 (6)	0.7270 (9)	0.043 (9)*
C8A'	1.03215 (19)	0.7642 (5)	0.67661 (8)	0.0249 (7)
N9'	0.96646 (16)	0.6806 (4)	0.64747 (7)	0.0255 (6)
C9A'	0.96460 (19)	0.8272 (5)	0.61347 (9)	0.0258 (7)
C10'	0.9071 (2)	0.4776 (5)	0.65181 (10)	0.0267 (7)
H10C	0.910 (2)	0.373 (6)	0.6277 (10)	0.042 (10)*
H10D	0.932 (2)	0.372 (5)	0.6747 (9)	0.033 (9)*
C11'	0.81229 (19)	0.5454 (5)	0.66032 (8)	0.0241 (6)
C12'	0.7931 (2)	0.7589 (6)	0.67972 (9)	0.0314 (7)
H12'	0.847 (2)	0.884 (6)	0.6895 (9)	0.047 (10)*
C13'	0.7052 (2)	0.8047 (7)	0.68913 (11)	0.0401 (9)
H13'	0.690 (2)	0.951 (6)	0.7018 (9)	0.042 (10)*
C14'	0.6376 (2)	0.6429 (7)	0.67937 (12)	0.0481 (10)
H14'	0.576 (3)	0.680 (7)	0.6901 (12)	0.075 (13)*
C15'	0.6564 (2)	0.4339 (7)	0.65933 (12)	0.0462 (10)
H15'	0.605 (3)	0.327 (6)	0.6506 (10)	0.054 (11)*
C16'	0.7434 (2)	0.3849 (6)	0.64961 (10)	0.0350 (8)
H16'	0.758 (2)	0.242 (6)	0.6364 (10)	0.041 (10)*

	U11	U22	U33	U12	U13	U23
C1	0.0220 (17)	0.053 (2)	0.045 (2)	−0.0002 (16)	0.0017 (14)	−0.0173 (18)
C2	0.029 (2)	0.085 (3)	0.034 (2)	0.009 (2)	−0.0012 (16)	−0.015 (2)
C3	0.031 (2)	0.086 (3)	0.0284 (18)	0.015 (2)	0.0033 (15)	0.0019 (19)
C4	0.0239 (18)	0.055 (2)	0.0316 (19)	0.0087 (17)	0.0072 (14)	0.0043 (17)
C4A	0.0183 (15)	0.0393 (18)	0.0288 (17)	0.0061 (14)	0.0056 (12)	−0.0019 (14)
C5	0.0219 (16)	0.0278 (16)	0.0372 (19)	0.0003 (13)	0.0090 (13)	−0.0011 (14)
C5A	0.0196 (15)	0.0290 (15)	0.0254 (15)	0.0057 (13)	0.0075 (12)	0.0015 (13)
C6	0.0225 (17)	0.0326 (17)	0.0379 (19)	−0.0054 (14)	0.0062 (14)	−0.0049 (15)
C7	0.0226 (16)	0.0366 (17)	0.0291 (17)	−0.0006 (14)	0.0024 (13)	−0.0058 (15)
C8	0.0247 (17)	0.0331 (16)	0.0280 (17)	0.0018 (14)	0.0059 (13)	0.0017 (14)
C8A	0.0172 (15)	0.0259 (15)	0.0308 (16)	0.0018 (12)	0.0074 (12)	−0.0026 (13)
N9	0.0188 (13)	0.0243 (12)	0.0358 (15)	−0.0004 (10)	0.0034 (10)	−0.0009 (11)
C9A	0.0153 (15)	0.0365 (17)	0.0305 (17)	0.0066 (13)	0.0030 (12)	−0.0057 (14)
C10	0.0203 (16)	0.0262 (17)	0.048 (2)	−0.0022 (13)	0.0043 (15)	0.0017 (16)
C11	0.0223 (16)	0.0238 (14)	0.0321 (16)	0.0021 (13)	0.0025 (12)	0.0043 (13)
C12	0.0273 (18)	0.0325 (17)	0.0408 (19)	−0.0022 (15)	0.0035 (14)	−0.0034 (15)
C13	0.0306 (19)	0.0331 (18)	0.042 (2)	0.0030 (15)	0.0097 (14)	−0.0013 (16)
C14	0.0210 (17)	0.0367 (18)	0.0360 (18)	0.0040 (15)	0.0046 (13)	0.0088 (15)
C15	0.0236 (17)	0.0416 (19)	0.0357 (18)	−0.0096 (15)	0.0011 (14)	0.0044 (16)
C16	0.0252 (17)	0.0284 (17)	0.0378 (19)	−0.0031 (14)	0.0021 (13)	−0.0021 (14)
C1'	0.0205 (16)	0.0371 (18)	0.0298 (17)	0.0043 (14)	0.0024 (13)	0.0036 (15)
C2'	0.0202 (16)	0.048 (2)	0.0318 (18)	0.0100 (15)	0.0054 (13)	0.0058 (16)
C3'	0.0312 (19)	0.0403 (19)	0.0336 (19)	0.0107 (15)	0.0126 (15)	0.0119 (16)
C4'	0.0245 (17)	0.0282 (16)	0.0376 (19)	0.0042 (14)	0.0154 (14)	0.0013 (14)
C4A'	0.0193 (15)	0.0261 (15)	0.0333 (16)	0.0024 (13)	0.0099 (12)	−0.0013 (13)
C5'	0.0248 (17)	0.0365 (18)	0.0378 (19)	−0.0033 (15)	0.0115 (14)	−0.0101 (15)
C5A'	0.0202 (15)	0.0294 (15)	0.0287 (16)	0.0016 (13)	0.0081 (12)	−0.0049 (13)
C6'	0.0304 (19)	0.054 (2)	0.0357 (19)	−0.0029 (18)	0.0048 (15)	−0.0164 (18)
C7'	0.0321 (19)	0.055 (2)	0.0249 (17)	0.0100 (17)	0.0017 (13)	−0.0072 (16)
C8'	0.0268 (17)	0.0378 (18)	0.0274 (17)	0.0045 (14)	0.0042 (13)	0.0007 (15)
C8A'	0.0199 (15)	0.0291 (16)	0.0263 (16)	0.0024 (13)	0.0060 (12)	−0.0036 (13)
N9'	0.0202 (13)	0.0284 (13)	0.0280 (13)	−0.0010 (11)	0.0030 (10)	0.0035 (11)
C9A'	0.0197 (15)	0.0291 (15)	0.0293 (16)	0.0026 (13)	0.0070 (12)	0.0011 (13)
C10'	0.0214 (16)	0.0252 (15)	0.0344 (18)	−0.0027 (13)	0.0075 (13)	−0.0020 (15)
C11'	0.0229 (15)	0.0278 (15)	0.0219 (15)	0.0012 (13)	0.0041 (12)	0.0057 (13)
C12'	0.0312 (18)	0.0352 (18)	0.0288 (17)	0.0031 (15)	0.0092 (13)	0.0028 (14)
C13'	0.039 (2)	0.043 (2)	0.042 (2)	0.0130 (18)	0.0205 (16)	0.0135 (18)
C14'	0.027 (2)	0.063 (3)	0.056 (2)	0.0101 (19)	0.0134 (17)	0.031 (2)
C15'	0.0245 (19)	0.051 (2)	0.062 (2)	−0.0046 (18)	−0.0030 (17)	0.022 (2)
C16'	0.0276 (18)	0.0325 (18)	0.044 (2)	−0.0049 (15)	−0.0042 (15)	0.0083 (16)

C1—C2	1.383 (5)	C1'—C2'	1.377 (4)
C1—H1	1.07 (3)	C1'—H1'	1.03 (3)
C2—H2	1.04 (3)	C2'—H2'	0.99 (3)
C3—C2	1.383 (6)	C3'—C2'	1.403 (5)
C3—H3	0.9300	C3'—H3'	0.95 (3)
C4—C3	1.380 (5)	C4'—C3'	1.381 (5)
C4—H4	0.93 (3)	C4'—H4'	0.99 (4)
C4A—C4	1.395 (4)	C4A'—C4'	1.389 (4)
C5—H5	1.02 (4)	C4A'—C5A'	1.449 (4)
C5A—C4A	1.442 (4)	C5'—C6'	1.374 (5)
C5A—C5	1.398 (4)	C5'—H5'	1.00 (3)
C6—C5	1.372 (4)	C5A'—C5'	1.404 (4)
C6—C7	1.401 (4)	C6'—H6'	0.97 (4)
C6—H6	0.97 (4)	C7'—C6'	1.394 (5)
C7—H7	0.97 (3)	C7'—H7'	0.9300
C8—C7	1.377 (4)	C8'—C7'	1.387 (4)
C8—H8	1.04 (3)	C8'—H8'	1.07 (3)
C8A—C5A	1.401 (4)	C8A'—C5A'	1.416 (4)
C8A—C8	1.398 (4)	C8A'—C8'	1.383 (4)
N9—C8A	1.391 (4)	N9'—C8A'	1.394 (4)
N9—C9A	1.381 (4)	N9'—C9A'	1.379 (4)
N9—C10	1.458 (4)	N9'—C10'	1.450 (4)
C9A—C1	1.396 (4)	C9A'—C1'	1.395 (4)
C9A—C4A	1.410 (4)	C9A'—C4A'	1.411 (4)
C10—C11	1.509 (4)	C10'—C11'	1.511 (4)
C10—H10A	1.00 (3)	C10'—H10C	0.98 (3)
C10—H10B	0.95 (3)	C10'—H10D	1.00 (3)
C11—C12	1.393 (4)	C11'—C12'	1.388 (4)
C11—C16	1.384 (4)	C11'—C16'	1.386 (4)
C12—H12	1.02 (4)	C12'—C13'	1.395 (4)
C13—C12	1.386 (4)	C12'—H12'	1.09 (3)
C13—H13	0.98 (3)	C13'—H13'	0.95 (3)
C14—C13	1.379 (5)	C14'—C13'	1.371 (5)
C14—C15	1.379 (5)	C14'—C15'	1.375 (6)
C14—H14	0.99 (4)	C14'—H14'	1.03 (4)
C15—C16	1.387 (4)	C15'—H15'	1.00 (4)
C15—H15	1.04 (3)	C16'—C15'	1.388 (5)
C16—H16	0.99 (3)	C16'—H16'	0.94 (3)
C2—C1—C9A	116.8 (4)	C2'—C1'—C9A'	117.5 (3)
C2—C1—H1	122.0 (17)	C2'—C1'—H1'	121.1 (16)
C9A—C1—H1	121.0 (17)	C9A'—C1'—H1'	121.2 (16)
C1—C2—H2	119.3 (18)	C1'—C2'—C3'	121.4 (3)
C3—C2—C1	122.1 (3)	C1'—C2'—H2'	112.6 (17)
C3—C2—H2	118.6 (18)	C3'—C2'—H2'	126.0 (17)
C2—C3—H3	119.3	C2'—C3'—H3'	120.5 (19)
C4—C3—C2	121.3 (3)	C4'—C3'—C2'	121.0 (3)
C4—C3—H3	119.3	C4'—C3'—H3'	118.5 (19)
C3—C4—C4A	118.2 (4)	C3'—C4'—C4A'	118.8 (3)
C3—C4—H4	119.5 (19)	C3'—C4'—H4'	117 (2)
C4A—C4—H4	122.2 (19)	C4A'—C4'—H4'	124 (2)
C4—C4A—C9A	119.9 (3)	C4'—C4A'—C5A'	134.1 (3)
C4—C4A—C5A	133.8 (3)	C4'—C4A'—C9A'	119.7 (3)
C9A—C4A—C5A	106.3 (3)	C9A'—C4A'—C5A'	106.2 (2)
C5A—C5—H5	122 (2)	C5A'—C5'—H5'	121.5 (18)
C6—C5—C5A	118.8 (3)	C6'—C5'—C5A'	118.7 (3)
C6—C5—H5	119 (2)	C6'—C5'—H5'	119.6 (19)
C5—C5A—C4A	133.4 (3)	C5'—C5A'—C4A'	133.5 (3)
C5—C5A—C8A	119.8 (3)	C5'—C5A'—C8A'	119.5 (3)
C8A—C5A—C4A	106.8 (3)	C8A'—C5A'—C4A'	107.1 (2)
C5—C6—C7	120.7 (3)	C5'—C6'—C7'	120.7 (3)
C5—C6—H6	119.5 (19)	C5'—C6'—H6'	117 (2)
C7—C6—H6	119.8 (19)	C7'—C6'—H6'	122 (2)
C6—C7—H7	120 (2)	C6'—C7'—H7'	118.9
C8—C7—C6	121.8 (3)	C8'—C7'—C6'	122.3 (3)
C8—C7—H7	118.5 (19)	C8'—C7'—H7'	118.9
C7—C8—C8A	117.2 (3)	C7'—C8'—H8'	121.4 (17)
C7—C8—H8	124.1 (18)	C8A'—C8'—C7'	117.0 (3)
C8A—C8—H8	118.6 (19)	C8A'—C8'—H8'	121.6 (17)
N9—C8A—C5A	109.2 (2)	N9'—C8A'—C5A'	108.3 (2)
N9—C8A—C8	129.2 (3)	C8'—C8A'—C5A'	121.8 (3)
C8—C8A—C5A	121.6 (3)	C8'—C8A'—N9'	129.9 (3)
C8A—N9—C10	126.8 (3)	C8A'—N9'—C10'	126.5 (2)
C9A—N9—C8A	108.1 (2)	C9A'—N9'—C8A'	109.0 (2)
C9A—N9—C10	124.9 (3)	C9A'—N9'—C10'	124.5 (2)
N9—C9A—C1	128.9 (3)	C1'—C9A'—C4A'	121.6 (3)
N9—C9A—C4A	109.5 (3)	N9'—C9A'—C1'	128.9 (3)
C1—C9A—C4A	121.6 (3)	N9'—C9A'—C4A'	109.5 (2)
N9—C10—C11	112.9 (2)	N9'—C10'—C11'	114.4 (2)
N9—C10—H10B	108.5 (19)	N9'—C10'—H10C	108.6 (19)
N9—C10—H10A	109.9 (18)	N9'—C10'—H10D	109.6 (18)
C11—C10—H10B	110.0 (18)	C11'—C10'—H10C	113.1 (19)
C11—C10—H10A	111.5 (18)	C11'—C10'—H10D	108.0 (18)
H10B—C10—H10A	104 (3)	H10C—C10'—H10D	103 (2)
C12—C11—C10	121.0 (3)	C12'—C11'—C10'	121.9 (3)
C16—C11—C10	120.1 (3)	C16'—C11'—C10'	118.7 (3)
C16—C11—C12	118.9 (3)	C16'—C11'—C12'	119.4 (3)
C11—C12—H12	121.7 (19)	C11'—C12'—C13'	119.3 (3)
C13—C12—C11	120.3 (3)	C11'—C12'—H12'	120.4 (18)
C13—C12—H12	118.0 (19)	C13'—C12'—H12'	120.1 (18)
C12—C13—H13	120 (2)	C12'—C13'—H13'	121 (2)
C14—C13—C12	120.3 (3)	C14'—C13'—C12'	121.1 (4)
C14—C13—H13	120 (2)	C14'—C13'—H13'	118 (2)
C13—C14—C15	119.8 (3)	C13'—C14'—C15'	119.4 (3)
C13—C14—H14	115 (2)	C13'—C14'—H14'	117 (2)
C15—C14—H14	125 (2)	C15'—C14'—H14'	124 (2)
C14—C15—C16	120.1 (3)	C14'—C15'—C16'	120.4 (4)
C14—C15—H15	120.5 (18)	C14'—C15'—H15'	117 (2)
C16—C15—H15	119.3 (18)	C16'—C15'—H15'	122 (2)
C11—C16—C15	120.7 (3)	C11'—C16'—C15'	120.3 (3)
C11—C16—H16	117.0 (17)	C11'—C16'—H16'	118 (2)
C15—C16—H16	122.3 (18)	C15'—C16'—H16'	122 (2)
C9A—C1—C2—C3	−1.1 (5)	C9A'—C1'—C2'—C3'	−0.8 (5)
C4—C3—C2—C1	1.0 (6)	C4'—C3'—C2'—C1'	0.3 (5)
C4A—C4—C3—C2	−0.2 (5)	C4A'—C4'—C3'—C2'	−0.2 (4)
C5A—C4A—C4—C3	177.8 (3)	C5A'—C4A'—C4'—C3'	178.8 (3)
C9A—C4A—C4—C3	−0.5 (5)	C9A'—C4A'—C4'—C3'	0.5 (4)
C5—C5A—C4A—C4	1.2 (6)	C4'—C4A'—C5A'—C5'	0.0 (6)
C5—C5A—C4A—C9A	179.7 (3)	C4'—C4A'—C5A'—C8A'	−178.6 (3)
C8A—C5A—C4A—C4	−179.4 (3)	C9A'—C4A'—C5A'—C5'	178.5 (3)
C8A—C5A—C4A—C9A	−0.9 (3)	C9A'—C4A'—C5A'—C8A'	−0.2 (3)
C8A—C5A—C5—C6	0.6 (4)	C5A'—C5'—C6'—C7'	−0.1 (5)
C4A—C5A—C5—C6	179.9 (3)	C4A'—C5A'—C5'—C6'	−177.8 (3)
C7—C6—C5—C5A	−0.2 (4)	C8A'—C5A'—C5'—C6'	0.7 (4)
C5—C6—C7—C8	−0.7 (5)	C8'—C7'—C6'—C5'	−1.0 (5)
C8A—C8—C7—C6	1.2 (4)	C8A'—C8'—C7'—C6'	1.5 (5)
C8—C8A—C5A—C4A	−179.5 (3)	N9'—C8A'—C5A'—C4A'	0.3 (3)
C8—C8A—C5A—C5	0.0 (4)	N9'—C8A'—C5A'—C5'	−178.5 (3)
N9—C8A—C5A—C4A	0.4 (3)	C8'—C8A'—C5A'—C4A'	178.7 (3)
N9—C8A—C5A—C5	179.9 (2)	C8'—C8A'—C5A'—C5'	−0.1 (4)
N9—C8A—C8—C7	179.2 (3)	N9'—C8A'—C8'—C7'	177.1 (3)
C5A—C8A—C8—C7	−0.8 (4)	C5A'—C8A'—C8'—C7'	−0.9 (4)
C9A—N9—C8A—C5A	0.2 (3)	C9A'—N9'—C8A'—C5A'	−0.3 (3)
C9A—N9—C8A—C8	−179.8 (3)	C9A'—N9'—C8A'—C8'	−178.6 (3)
C10—N9—C8A—C5A	−175.1 (3)	C10'—N9'—C8A'—C8'	3.0 (5)
C10—N9—C8A—C8	4.8 (5)	C10'—N9'—C8A'—C5A'	−178.7 (3)
C8A—N9—C9A—C1	178.6 (3)	C8A'—N9'—C9A'—C1'	179.9 (3)
C8A—N9—C9A—C4A	−0.8 (3)	C8A'—N9'—C9A'—C4A'	0.2 (3)
C10—N9—C9A—C1	−5.9 (5)	C10'—N9'—C9A'—C1'	−1.7 (5)
C10—N9—C9A—C4A	174.7 (3)	C10'—N9'—C9A'—C4A'	178.6 (3)
C8A—N9—C10—C11	104.4 (3)	C8A'—N9'—C10'—C11'	102.9 (3)
C9A—N9—C10—C11	−70.2 (4)	C9A'—N9'—C10'—C11'	−75.2 (4)
N9—C9A—C1—C2	−178.9 (3)	N9'—C9A'—C1'—C2'	−178.5 (3)
C4A—C9A—C1—C2	0.5 (5)	C4A'—C9A'—C1'—C2'	1.1 (4)
N9—C9A—C4A—C4	179.8 (3)	N9'—C9A'—C4A'—C4'	178.7 (2)
N9—C9A—C4A—C5A	1.1 (3)	N9'—C9A'—C4A'—C5A'	0.0 (3)
C1—C9A—C4A—C4	0.3 (4)	C1'—C9A'—C4A'—C4'	−1.0 (4)
C1—C9A—C4A—C5A	−178.4 (3)	C1'—C9A'—C4A'—C5A'	−179.7 (3)
N9—C10—C11—C12	−54.4 (4)	N9'—C10'—C11'—C16'	155.3 (3)
N9—C10—C11—C16	125.9 (3)	N9'—C10'—C11'—C12'	−26.9 (4)
C10—C11—C12—C13	−179.6 (3)	C10'—C11'—C12'—C13'	−175.9 (3)
C16—C11—C12—C13	0.0 (5)	C16'—C11'—C12'—C13'	1.9 (4)
C10—C11—C16—C15	179.8 (3)	C10'—C11'—C16'—C15'	175.8 (3)
C12—C11—C16—C15	0.2 (5)	C12'—C11'—C16'—C15'	−2.0 (5)
C14—C13—C12—C11	−0.2 (5)	C11'—C12'—C13'—C14'	−0.3 (5)
C15—C14—C13—C12	0.2 (5)	C15'—C14'—C13'—C12'	−1.1 (5)
C13—C14—C15—C16	−0.1 (5)	C13'—C14'—C15'—C16'	1.0 (5)
C14—C15—C16—C11	−0.1 (5)	C11'—C16'—C15'—C14'	0.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cg1'i	0.97 (4)	2.940 (4)	3.636 (5)	129.46 (5)
C10'—H10C···Cg1'ii	0.98 (3)	2.787 (4)	3.700 (5)	154.92 (4)
C4'—H4'···Cg3i	0.99 (4)	2.706 (4)	3.554 (4)	144.36 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cg1′i	0.97 (4)	2.940 (4)	3.636 (5)	129.46 (5)
C10′—H10C⋯Cg1′ii	0.98 (3)	2.787 (4)	3.700 (5)	154.92 (4)
C4′—H4′⋯Cg3i	0.99 (4)	2.706 (4)	3.554 (4)	144.36 (5)

Symmetry codes: (i) ; (ii) . Cg1′ and Cg3 are the centroids of the C1′–C4′/C4A′/C9A′ and C5A/C5–C8/C8A rings, respectively.