9-Ethyl-3-(9H-9-ethyl­carbazol-3-yl)-4-nitro­-9H-carbazole

In the mol­ecule of the title compound, C₂₈H₂₃N₃O₂, the nitro group is almost perpendicular to the carbazole ring to which it is attached. The crystal packing is determined by C—H...O and π–π inter­actions, where the nitrated carbazole ring of one mol­ecule associates in a shifted parallel planar orientation with the centrosymmetrically related non-nitrated carbazole ring of a neighbouring mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.038
• wR factor = 0.106
• Data-to-parameter ratio = 6.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         N4

Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       6.61
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.03
           From the CIF: _reflns_number_total               1975
           Count of symmetry unique reflns         1985
           Completeness (_total/calc)             99.50%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

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

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

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Computing details

Data collection: CAD-4 PC Software (Enraf–Nonius, 1993); cell refinement: CAD-4 PC Software; data reduction: DATRD2 in NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

9-Ethyl-3-(9-ethyl-9H-carbazol-3-yl)-4-nitro-9H-carbazole

Crystal data

C28H23N3O2	F(000) = 912
Mr = 433.49	Dx = 1.287 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 25 reflections
a = 16.2810 (13) Å	θ = 5.7–18.4°
b = 13.8472 (8) Å	µ = 0.08 mm^−1
c = 9.9233 (9) Å	T = 295 K
β = 90.721 (7)°	Slab, yellow
V = 2237.0 (3) Å^3	0.51 × 0.27 × 0.17 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.010
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 1.9°
Graphite monochromator	h = −19→19
ω scan b/P/b	k = −16→16
2071 measured reflections	l = 0→11
1975 independent reflections	3 standard reflections every 120 min
1466 reflections with I > 2σ(I)	intensity decay: 1.1%

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0661P)^2 + 0.1062P] where P = (Fo^2 + 2Fc^2)/3
1975 reflections	(Δ/σ)max = 0.017
299 parameters	Δρmax = 0.14 e Å^−3
2 restraints	Δρmin = −0.17 e Å^−3

Special details

Experimental. Spectroscopic analysis: ¹H NMR (300 MHz, CDCl₃, δ, p.p.m.): 8.19 (d, J = 1.83 Hz, 1H), 8.11 (d, J = 7.31 Hz, 1H), 7.98 (d, J = 8.04 Hz, 1H), 7.65–7.40 (m, 8H), 7.30–7.20 (m, 2H), 4.44 (q, J = 7.31 Hz, 2H), 4.38 (q, J = 7.31 Hz, 2H), 1.45 (t, J = 7.13 Hz, 6H).

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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

13.2893 (0.0611) x - 4.2421 (0.0826) y - 4.9618 (0.0339) z = 6.3368 (0.0537)

* 0.0000 (0.0000) N4 * 0.0000 (0.0000) O1 * 0.0000 (0.0000) O2

Rms deviation of fitted atoms = 0.0000

2.7290 (0.0139) x - 7.0608 (0.0115) y + 8.3511 (0.0043) z = 4.5188 (0.0133)

Angle to previous plane (with approximate e.s.d.) = 83.10 (1/4)

* -0.0440 (0.0039) C1 * -0.0549 (0.0037) C2 * -0.0134 (0.0036) C3 * 0.0500 (0.0037) C4 * 0.0470 (0.0038) C4a * 0.0388 (0.0040) C4b * -0.0222 (0.0040) C5 * -0.0500 (0.0041) C6 * -0.0258 (0.0044) C7 * 0.0108 (0.0039) C8 * 0.0244 (0.0044) C8a * 0.0203 (0.0039) C9a * 0.0190 (0.0036) N9

Rms deviation of fitted atoms = 0.0356

2.2053 (0.0134) x + 7.3527 (0.0107) y + 8.2831 (0.0044) z = 7.2323 (0.0053)

Angle to previous plane (with approximate e.s.d.) = 62.76 (0.05)

* 0.0053 (0.0039) C1' * 0.0357 (0.0036) C2' * 0.0117 (0.0036) C3' * -0.0238 (0.0038) C4' * -0.0378 (0.0039) C4a' * -0.0238 (0.0042) C4b' * 0.0024 (0.0041) C5' * 0.0422 (0.0039) C6' * 0.0122 (0.0044) C7' * -0.0143 (0.0041) C8' * -0.0191 (0.0041) C8a' * -0.0022 (0.0041) C9a' * 0.0115 (0.0035) N9'

Rms deviation of fitted atoms = 0.0226

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
N4	0.64411 (18)	0.0612 (2)	0.3957 (3)	0.0577 (7)
O1	0.6469 (3)	−0.0107 (2)	0.4645 (4)	0.1079 (11)
O2	0.6068 (3)	0.0666 (2)	0.2912 (4)	0.1139 (13)
N9	0.8983 (2)	0.2210 (3)	0.4367 (4)	0.0572 (10)
C1	0.7774 (3)	0.3050 (3)	0.5396 (5)	0.0585 (13)
H1	0.8069	0.3581	0.5708	0.07*
C2	0.6937 (3)	0.2978 (3)	0.5596 (5)	0.0572 (12)
H2	0.6672	0.3471	0.6056	0.069*
C3	0.6472 (3)	0.2188 (3)	0.5130 (4)	0.0514 (12)
C4	0.6896 (3)	0.1458 (3)	0.4450 (4)	0.0485 (11)
C4a	0.7732 (3)	0.1496 (3)	0.4206 (4)	0.0489 (11)
C4b	0.8323 (3)	0.0897 (3)	0.3496 (4)	0.0494 (11)
C5	0.8275 (3)	0.0051 (4)	0.2724 (5)	0.0621 (13)
H5	0.7775	−0.0262	0.2597	0.074*
C6	0.8977 (3)	−0.0308 (4)	0.2157 (5)	0.0712 (14)
H6	0.8954	−0.0871	0.1647	0.085*
C7	0.9728 (3)	0.0169 (5)	0.2345 (5)	0.0711 (14)
H7	1.0196	−0.0091	0.196	0.085*
C8	0.9796 (3)	0.0990 (4)	0.3060 (5)	0.0681 (15)
H8	1.0302	0.1294	0.3171	0.082*
C8a	0.9084 (3)	0.1377 (4)	0.3636 (5)	0.0553 (12)
C9a	0.8160 (3)	0.2300 (3)	0.4713 (4)	0.0478 (11)
C10	0.9628 (3)	0.2899 (4)	0.4738 (5)	0.0714 (15)
H10A	0.9395	0.3544	0.4766	0.086*
H10B	1.0047	0.2893	0.4052	0.086*
C11	1.0019 (4)	0.2674 (5)	0.6083 (6)	0.0922 (19)
H11A	1.0441	0.3139	0.6279	0.138*
H11B	1.0256	0.2039	0.6059	0.138*
H11C	0.961	0.2698	0.6771	0.138*
N9'	0.3058 (2)	0.2217 (3)	0.5963 (4)	0.0535 (9)
C1'	0.4270 (3)	0.3021 (4)	0.4919 (4)	0.0563 (13)
H1'	0.3976	0.3528	0.4529	0.068*
C2'	0.5104 (3)	0.2958 (3)	0.4790 (5)	0.0571 (12)
H2'	0.5375	0.3446	0.4331	0.069*
C3'	0.5571 (3)	0.2183 (3)	0.5325 (4)	0.0491 (11)
C4'	0.5170 (3)	0.1471 (3)	0.6020 (4)	0.0483 (11)
H4'	0.5466	0.0956	0.6381	0.058*
C4a'	0.4323 (3)	0.1517 (3)	0.6189 (4)	0.0468 (11)
C4b'	0.3736 (3)	0.0925 (3)	0.6887 (5)	0.0511 (11)
C5'	0.3793 (3)	0.0082 (3)	0.7651 (5)	0.0592 (12)
H5'	0.4297	−0.0223	0.7777	0.071*
C6'	0.3091 (3)	−0.0292 (4)	0.8219 (5)	0.0687 (14)
H6'	0.313	−0.0842	0.8755	0.082*
C7'	0.2336 (3)	0.0129 (5)	0.8009 (5)	0.0788 (16)
H7'	0.1872	−0.0152	0.8379	0.095*
C8'	0.2255 (3)	0.0981 (4)	0.7243 (5)	0.0650 (14)
H8'	0.1746	0.1271	0.7104	0.078*
C8a'	0.2962 (3)	0.1367 (3)	0.6706 (4)	0.0511 (11)
C9a'	0.3874 (3)	0.2309 (3)	0.5648 (5)	0.0512 (12)
C10'	0.2417 (3)	0.2886 (4)	0.5556 (5)	0.0605 (13)
H10C	0.2641	0.3535	0.5538	0.073*
H10D	0.1983	0.2873	0.6217	0.073*
C11'	0.2052 (3)	0.2646 (4)	0.4167 (6)	0.0807 (17)
H11D	0.1625	0.3099	0.3949	0.121*
H11E	0.1829	0.2004	0.4179	0.121*
H11F	0.2475	0.2684	0.3503	0.121*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N4	0.0492 (16)	0.0518 (18)	0.072 (2)	0.0027 (13)	−0.0035 (14)	−0.0034 (16)
O1	0.144 (3)	0.0511 (15)	0.128 (3)	−0.0102 (17)	−0.023 (2)	0.015 (2)
O2	0.142 (3)	0.096 (2)	0.103 (2)	−0.031 (2)	−0.064 (2)	0.0035 (19)
N9	0.051 (2)	0.068 (2)	0.052 (2)	−0.011 (2)	−0.0044 (18)	0.000 (2)
C1	0.065 (3)	0.053 (3)	0.058 (3)	−0.007 (2)	−0.004 (2)	0.000 (2)
C2	0.058 (3)	0.059 (3)	0.055 (3)	0.002 (3)	−0.001 (2)	−0.009 (2)
C3	0.048 (3)	0.057 (3)	0.049 (3)	0.004 (2)	−0.004 (2)	0.004 (2)
C4	0.045 (3)	0.045 (2)	0.056 (3)	−0.002 (2)	−0.004 (2)	0.004 (2)
C4a	0.048 (3)	0.051 (3)	0.047 (3)	0.000 (2)	−0.007 (2)	0.004 (2)
C4b	0.055 (3)	0.054 (3)	0.039 (2)	0.002 (2)	−0.005 (2)	0.010 (2)
C5	0.071 (3)	0.058 (3)	0.057 (3)	0.006 (3)	−0.012 (2)	0.000 (2)
C6	0.080 (4)	0.067 (3)	0.067 (4)	0.022 (3)	0.002 (3)	−0.005 (3)
C7	0.064 (3)	0.084 (4)	0.066 (3)	0.017 (3)	0.014 (3)	0.008 (3)
C8	0.061 (3)	0.087 (4)	0.057 (3)	0.006 (3)	0.002 (3)	0.013 (3)
C8a	0.051 (3)	0.067 (3)	0.047 (3)	0.003 (3)	−0.009 (2)	0.005 (2)
C9a	0.045 (3)	0.055 (3)	0.043 (3)	−0.004 (2)	−0.003 (2)	0.002 (2)
C10	0.063 (3)	0.082 (4)	0.068 (3)	−0.007 (3)	−0.017 (3)	0.007 (3)
C11	0.082 (4)	0.124 (5)	0.071 (4)	−0.020 (4)	−0.019 (3)	0.010 (3)
N9'	0.042 (2)	0.059 (2)	0.059 (3)	0.0061 (19)	−0.0045 (17)	−0.0032 (19)
C1'	0.062 (3)	0.055 (3)	0.051 (3)	0.018 (2)	−0.005 (2)	0.008 (2)
C2'	0.066 (3)	0.050 (3)	0.055 (3)	0.003 (2)	0.002 (2)	0.006 (2)
C3'	0.056 (3)	0.047 (2)	0.044 (2)	0.005 (2)	0.002 (2)	0.000 (2)
C4'	0.050 (3)	0.047 (2)	0.048 (2)	0.007 (2)	−0.009 (2)	0.004 (2)
C4a'	0.050 (3)	0.049 (2)	0.041 (2)	0.003 (2)	−0.003 (2)	−0.001 (2)
C4b'	0.049 (3)	0.052 (3)	0.052 (3)	−0.003 (2)	−0.008 (2)	−0.001 (2)
C5'	0.054 (3)	0.058 (3)	0.066 (3)	−0.007 (3)	0.000 (2)	−0.002 (3)
C6'	0.079 (4)	0.065 (3)	0.061 (3)	−0.015 (3)	−0.004 (3)	0.003 (3)
C7'	0.072 (4)	0.087 (4)	0.077 (4)	−0.031 (3)	0.000 (3)	−0.004 (3)
C8'	0.043 (3)	0.079 (4)	0.073 (3)	0.000 (2)	0.004 (2)	−0.012 (3)
C8a'	0.051 (3)	0.056 (3)	0.047 (3)	−0.001 (3)	0.002 (2)	−0.011 (2)
C9a'	0.055 (3)	0.052 (3)	0.047 (3)	0.007 (2)	−0.008 (2)	−0.005 (2)
C10'	0.048 (3)	0.061 (3)	0.072 (3)	0.023 (2)	0.001 (2)	−0.011 (2)
C11'	0.078 (4)	0.077 (3)	0.086 (4)	0.028 (3)	−0.037 (3)	−0.013 (3)

Geometric parameters (Å, º)

N4—O2	1.197 (4)	C11—H11C	0.96
N4—O1	1.208 (4)	N9'—C9a'	1.374 (6)
N4—C4	1.466 (5)	N9'—C8a'	1.398 (6)
N9—C8a	1.374 (6)	N9'—C10'	1.450 (5)
N9—C9a	1.392 (6)	C1'—C2'	1.368 (6)
N9—C10	1.463 (6)	C1'—C9a'	1.387 (7)
C1—C2	1.383 (7)	C1'—H1'	0.93
C1—C9a	1.394 (7)	C2'—C3'	1.415 (6)
C1—H1	0.93	C2'—H2'	0.93
C2—C3	1.406 (6)	C3'—C4'	1.373 (6)
C2—H2	0.93	C4'—C4a'	1.393 (6)
C3—C4	1.402 (6)	C4'—H4'	0.93
C3—C3'	1.482 (4)	C4a'—C9a'	1.420 (6)
C4—C4a	1.388 (6)	C4a'—C4b'	1.443 (6)
C4a—C9a	1.403 (6)	C4b'—C5'	1.394 (6)
C4a—C4b	1.458 (6)	C4b'—C8a'	1.410 (6)
C4b—C5	1.402 (7)	C5'—C6'	1.382 (6)
C4b—C8a	1.410 (6)	C5'—H5'	0.93
C5—C6	1.373 (7)	C6'—C7'	1.374 (7)
C5—H5	0.93	C6'—H6'	0.93
C6—C7	1.400 (8)	C7'—C8'	1.408 (8)
C6—H6	0.93	C7'—H7'	0.93
C7—C8	1.343 (8)	C8'—C8a'	1.382 (6)
C7—H7	0.93	C8'—H8'	0.93
C8—C8a	1.406 (7)	C10'—C11'	1.530 (6)
C8—H8	0.93	C10'—H10C	0.97
C10—C11	1.505 (7)	C10'—H10D	0.97
C10—H10A	0.97	C11'—H11D	0.96
C10—H10B	0.97	C11'—H11E	0.96
C11—H11A	0.96	C11'—H11F	0.96
C11—H11B	0.96
O2—N4—O1	123.8 (3)	H11B—C11—H11C	109.5
O2—N4—C4	119.2 (3)	C9a'—N9'—C8a'	108.3 (4)
O1—N4—C4	117.0 (3)	C9a'—N9'—C10'	124.9 (4)
C8a—N9—C9a	109.1 (4)	C8a'—N9'—C10'	126.9 (4)
C8a—N9—C10	126.2 (4)	C2'—C1'—C9a'	118.1 (4)
C9a—N9—C10	124.8 (4)	C2'—C1'—H1'	120.9
C2—C1—C9a	117.9 (4)	C9a'—C1'—H1'	120.9
C2—C1—H1	121.1	C1'—C2'—C3'	122.9 (5)
C9a—C1—H1	121.1	C1'—C2'—H2'	118.6
C1—C2—C3	122.4 (5)	C3'—C2'—H2'	118.6
C1—C2—H2	118.8	C4'—C3'—C2'	118.5 (5)
C3—C2—H2	118.8	C4'—C3'—C3	123.1 (4)
C4—C3—C2	117.0 (4)	C2'—C3'—C3	118.4 (4)
C4—C3—C3'	123.6 (4)	C3'—C4'—C4a'	120.4 (4)
C2—C3—C3'	119.4 (5)	C3'—C4'—H4'	119.8
C4a—C4—C3	123.1 (4)	C4a'—C4'—H4'	119.8
C4a—C4—N4	117.7 (4)	C4'—C4a'—C9a'	119.7 (4)
C3—C4—N4	119.2 (4)	C4'—C4a'—C4b'	134.1 (4)
C4—C4a—C9a	116.9 (4)	C9a'—C4a'—C4b'	106.2 (4)
C4—C4a—C4b	135.8 (4)	C5'—C4b'—C8a'	119.1 (5)
C9a—C4a—C4b	107.3 (4)	C5'—C4b'—C4a'	134.1 (4)
C5—C4b—C8a	119.4 (5)	C8a'—C4b'—C4a'	106.8 (4)
C5—C4b—C4a	135.0 (4)	C6'—C5'—C4b'	119.0 (5)
C8a—C4b—C4a	105.5 (4)	C6'—C5'—H5'	120.5
C6—C5—C4b	119.1 (5)	C4b'—C5'—H5'	120.5
C6—C5—H5	120.5	C7'—C6'—C5'	121.4 (5)
C4b—C5—H5	120.5	C7'—C6'—H6'	119.3
C5—C6—C7	120.2 (5)	C5'—C6'—H6'	119.3
C5—C6—H6	119.9	C6'—C7'—C8'	121.0 (5)
C7—C6—H6	119.9	C6'—C7'—H7'	119.5
C8—C7—C6	122.5 (5)	C8'—C7'—H7'	119.5
C8—C7—H7	118.8	C8a'—C8'—C7'	117.3 (5)
C6—C7—H7	118.8	C8a'—C8'—H8'	121.3
C7—C8—C8a	118.3 (5)	C7'—C8'—H8'	121.3
C7—C8—H8	120.9	C8'—C8a'—N9'	128.9 (4)
C8a—C8—H8	120.9	C8'—C8a'—C4b'	122.0 (5)
N9—C8a—C8	129.8 (5)	N9'—C8a'—C4b'	109.0 (4)
N9—C8a—C4b	109.7 (4)	N9'—C9a'—C1'	129.9 (4)
C8—C8a—C4b	120.5 (5)	N9'—C9a'—C4a'	109.7 (4)
N9—C9a—C1	128.9 (4)	C1'—C9a'—C4a'	120.4 (4)
N9—C9a—C4a	108.4 (4)	N9'—C10'—C11'	112.5 (4)
C1—C9a—C4a	122.7 (4)	N9'—C10'—H10C	109.1
N9—C10—C11	112.5 (5)	C11'—C10'—H10C	109.1
N9—C10—H10A	109.1	N9'—C10'—H10D	109.1
C11—C10—H10A	109.1	C11'—C10'—H10D	109.1
N9—C10—H10B	109.1	H10C—C10'—H10D	107.8
C11—C10—H10B	109.1	C10'—C11'—H11D	109.5
H10A—C10—H10B	107.8	C10'—C11'—H11E	109.5
C10—C11—H11A	109.5	H11D—C11'—H11E	109.5
C10—C11—H11B	109.5	C10'—C11'—H11F	109.5
H11A—C11—H11B	109.5	H11D—C11'—H11F	109.5
C10—C11—H11C	109.5	H11E—C11'—H11F	109.5
H11A—C11—H11C	109.5
C9a—C1—C2—C3	−0.5 (7)	C8a—N9—C10—C11	−91.3 (6)
C1—C2—C3—C4	0.4 (6)	C9a—N9—C10—C11	88.4 (6)
C1—C2—C3—C3'	−177.1 (4)	C9a'—C1'—C2'—C3'	2.3 (6)
C2—C3—C4—C4a	−1.3 (7)	C1'—C2'—C3'—C4'	−1.0 (6)
C3'—C3—C4—C4a	176.2 (4)	C1'—C2'—C3'—C3	−179.8 (4)
C2—C3—C4—N4	179.3 (3)	C4—C3—C3'—C4'	61.0 (4)
C3'—C3—C4—N4	−3.2 (6)	C2—C3—C3'—C4'	−121.6 (6)
O2—N4—C4—C4a	−98.0 (5)	C4—C3—C3'—C2'	−120.2 (6)
O1—N4—C4—C4a	82.0 (5)	C2—C3—C3'—C2'	57.2 (3)
O2—N4—C4—C3	81.5 (5)	C2'—C3'—C4'—C4a'	0.1 (7)
O1—N4—C4—C3	−98.6 (5)	C3—C3'—C4'—C4a'	178.9 (4)
C3—C4—C4a—C9a	2.0 (6)	C3'—C4'—C4a'—C9a'	−0.6 (6)
N4—C4—C4a—C9a	−178.5 (4)	C3'—C4'—C4a'—C4b'	−177.3 (5)
C3—C4—C4a—C4b	−176.5 (5)	C4'—C4a'—C4b'—C5'	−0.4 (9)
N4—C4—C4a—C4b	3.0 (7)	C9a'—C4a'—C4b'—C5'	−177.4 (5)
C4—C4a—C4b—C5	3.1 (9)	C4'—C4a'—C4b'—C8a'	178.6 (5)
C9a—C4a—C4b—C5	−175.6 (5)	C9a'—C4a'—C4b'—C8a'	1.6 (5)
C4—C4a—C4b—C8a	179.3 (5)	C8a'—C4b'—C5'—C6'	−0.5 (7)
C9a—C4a—C4b—C8a	0.7 (5)	C4a'—C4b'—C5'—C6'	178.4 (5)
C8a—C4b—C5—C6	2.1 (7)	C4b'—C5'—C6'—C7'	2.2 (7)
C4a—C4b—C5—C6	178.0 (5)	C5'—C6'—C7'—C8'	−2.2 (8)
C4b—C5—C6—C7	−0.4 (7)	C6'—C7'—C8'—C8a'	0.5 (8)
C5—C6—C7—C8	−0.7 (8)	C7'—C8'—C8a'—N9'	−177.1 (5)
C6—C7—C8—C8a	0.0 (8)	C7'—C8'—C8a'—C4b'	1.2 (7)
C9a—N9—C8a—C8	179.2 (5)	C9a'—N9'—C8a'—C8'	179.7 (5)
C10—N9—C8a—C8	−1.0 (8)	C10'—N9'—C8a'—C8'	−1.6 (7)
C9a—N9—C8a—C4b	−0.4 (5)	C9a'—N9'—C8a'—C4b'	1.2 (5)
C10—N9—C8a—C4b	179.3 (4)	C10'—N9'—C8a'—C4b'	179.9 (4)
C7—C8—C8a—N9	−177.8 (5)	C5'—C4b'—C8a'—C8'	−1.2 (7)
C7—C8—C8a—C4b	1.8 (7)	C4a'—C4b'—C8a'—C8'	179.6 (4)
C5—C4b—C8a—N9	176.8 (4)	C5'—C4b'—C8a'—N9'	177.4 (4)
C4a—C4b—C8a—N9	−0.2 (5)	C4a'—C4b'—C8a'—N9'	−1.8 (5)
C5—C4b—C8a—C8	−2.9 (7)	C8a'—N9'—C9a'—C1'	179.4 (5)
C4a—C4b—C8a—C8	−179.9 (4)	C10'—N9'—C9a'—C1'	0.6 (8)
C8a—N9—C9a—C1	−176.8 (5)	C8a'—N9'—C9a'—C4a'	−0.2 (5)
C10—N9—C9a—C1	3.5 (7)	C10'—N9'—C9a'—C4a'	−178.9 (4)
C8a—N9—C9a—C4a	0.9 (5)	C2'—C1'—C9a'—N9'	177.7 (5)
C10—N9—C9a—C4a	−178.9 (4)	C2'—C1'—C9a'—C4a'	−2.8 (7)
C2—C1—C9a—N9	178.7 (4)	C4'—C4a'—C9a'—N9'	−178.4 (4)
C2—C1—C9a—C4a	1.3 (7)	C4b'—C4a'—C9a'—N9'	−0.9 (5)
C4—C4a—C9a—N9	−179.9 (4)	C4'—C4a'—C9a'—C1'	2.0 (6)
C4b—C4a—C9a—N9	−1.0 (5)	C4b'—C4a'—C9a'—C1'	179.5 (4)
C4—C4a—C9a—C1	−2.0 (6)	C9a'—N9'—C10'—C11'	87.1 (6)
C4b—C4a—C9a—C1	176.9 (4)	C8a'—N9'—C10'—C11'	−91.4 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11a···O2^i	0.96	2.52	3.379 (7)	149
C11′—H11d···O1^ii	0.96	2.59	3.290 (6)	130

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x−1/2, y+1/2, z.