1,3-Bis(9-ethyl­carbazol-3-yl)propane

In the title compund, C₃₁H₃₀N₂, π–π overlap is absent in the region where carbazole groups of two adjacent mol­ecules are inclined toward each other. The eth­yl groups which protrude from the plane of the carbazole groups and the alkyl­ene chain connecting the two carbazole groups are responsible for the poor mol­ecular stacking.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.052
• wR factor = 0.129
• Data-to-parameter ratio = 8.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.95
PLAT128_ALERT_4_C Non-standard setting of Space group Pca21   ....    P21ca
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C7
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C31 H30 N2

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           25.08
           From the CIF: _reflns_number_total               2370
           Count of symmetry unique reflns         2369
           Completeness (_total/calc)            100.04%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         1
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

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

   1 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
   4 ALERT type 4 Improvement, methodology, query or suggestion

---

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 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

1,3-bis(9-ethyl-9H-carbazol-3-yl)propane

Crystal data

C31H30N2	F(000) = 920
Mr = 430.57	Dx = 1.158 Mg m^−3
Orthorhombic, P21ca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2ac 2a	Cell parameters from 25 reflections
a = 8.1950 (8) Å	θ = 4.0–14.0°
b = 11.1921 (8) Å	µ = 0.07 mm^−1
c = 26.931 (3) Å	T = 293 K
V = 2470.1 (3) Å^3	Plate, colorless
Z = 4	0.36 × 0.32 × 0.23 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.023
Radiation source: fine-focus sealed tube	θmax = 25.1°, θmin = 1.5°
Graphite monochromator	h = −9→9
ω scans	k = −12→13
3373 measured reflections	l = −31→32
2370 independent reflections	3 standard reflections every 120 min
1246 reflections with I > 2σ(I)	intensity decay: 1.0%

Refinement

Refinement on F^2	1 restraint
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.052	w = 1/[σ^2(Fo^2) + (0.064P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.129	(Δ/σ)max < 0.001
S = 0.96	Δρmax = 0.13 e Å^−3
2370 reflections	Δρmin = −0.11 e Å^−3
298 parameters

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
N'	0.1232 (4)	0.1271 (4)	0.35003 (14)	0.0692 (11)
N	0.8690 (5)	−0.6545 (4)	0.49351 (15)	0.0776 (12)
C1'	0.1921 (6)	−0.0892 (5)	0.34734 (19)	0.0796 (14)
C1	0.9753 (8)	−0.4785 (5)	0.4441 (2)	0.0878 (15)
C2'	0.3075 (7)	−0.1686 (5)	0.3306 (2)	0.0851 (16)
C2	0.9478 (8)	−0.4130 (5)	0.4025 (2)	0.0886 (16)
C3'	0.4458 (6)	−0.1323 (5)	0.30350 (18)	0.0740 (14)
C3	0.8246 (7)	−0.4404 (5)	0.36885 (19)	0.0757 (14)
C4'	0.4619 (6)	−0.0143 (5)	0.29139 (15)	0.0686 (12)
C4	0.7231 (6)	−0.5343 (4)	0.37911 (17)	0.0696 (13)
C4A'	0.3482 (5)	0.0672 (5)	0.30766 (15)	0.0608 (12)
C4A	0.7446 (6)	−0.6025 (4)	0.42122 (16)	0.0628 (12)
C4B'	0.3339 (6)	0.1951 (5)	0.30329 (16)	0.0623 (12)
C4B	0.6622 (6)	−0.7041 (4)	0.44167 (16)	0.0688 (13)
C5'	0.4285 (6)	0.2828 (5)	0.27995 (18)	0.0797 (15)
C5	0.5276 (6)	−0.7719 (6)	0.4272 (2)	0.0918 (17)
C6'	0.3795 (7)	0.3992 (6)	0.2839 (2)	0.0888 (17)
C6	0.4822 (9)	−0.8685 (6)	0.4548 (3)	0.1085 (19)
C7'	0.2423 (8)	0.4296 (6)	0.3108 (2)	0.0976 (18)
C7	0.5673 (11)	−0.8984 (6)	0.4972 (3)	0.120 (2)
C8'	0.1474 (7)	0.3460 (5)	0.33397 (19)	0.0820 (15)
C8	0.6983 (9)	−0.8324 (6)	0.5137 (2)	0.0959 (18)
C8A'	0.1935 (5)	0.2285 (5)	0.33006 (16)	0.0639 (12)
C8A	0.7445 (7)	−0.7365 (5)	0.48570 (18)	0.0728 (14)
C9A'	0.2131 (6)	0.0296 (5)	0.33634 (17)	0.0643 (12)
C9A	0.8723 (6)	−0.5735 (5)	0.4541 (2)	0.0702 (13)
C10'	−0.0316 (6)	0.1234 (5)	0.37672 (18)	0.0794 (14)
C10	0.9940 (8)	−0.6628 (5)	0.5313 (2)	0.107 (2)
C11'	−0.1736 (7)	0.1014 (7)	0.3419 (2)	0.118 (2)
C11	1.1351 (10)	−0.7386 (7)	0.5159 (3)	0.148 (3)
C12'	0.5749 (8)	−0.2233 (5)	0.29012 (19)	0.0947 (17)
C12	0.7946 (8)	−0.3616 (5)	0.3240 (2)	0.0966 (18)
C13	0.6555 (9)	−0.2732 (5)	0.33376 (19)	0.109 (2)
H1'	0.1024	−0.1151	0.3656	0.095*
H1	1.0613	−0.4601	0.4653	0.105*
H10A	−0.0479	0.1987	0.3939	0.095*
H10B	−0.0279	0.0604	0.4014	0.095*
H10C	0.9464	−0.6959	0.5613	0.129*
H10D	1.0331	−0.5832	0.539	0.129*
H11A	−0.2735	0.1007	0.3605	0.178*
H11B	−0.1594	0.0257	0.3256	0.178*
H11C	−0.1777	0.1638	0.3174	0.178*
H11D	1.2127	−0.7428	0.5425	0.222*
H11E	1.1861	−0.7042	0.4872	0.222*
H11F	1.0972	−0.8175	0.5081	0.222*
H12A	0.7673	−0.4112	0.2956	0.116*
H12B	0.8934	−0.3178	0.3161	0.116*
H12C	0.5248	−0.2876	0.2714	0.114*
H12D	0.6561	−0.1858	0.269	0.114*
H13A	0.5736	−0.3132	0.3538	0.13*
H13B	0.6984	−0.2076	0.3533	0.13*
H2'	0.2938	−0.2494	0.3375	0.102*
H2	1.0139	−0.3472	0.3963	0.106*
H4'	0.5497	0.0109	0.2722	0.082*
H4	0.6385	−0.5524	0.3574	0.084*
H5	0.4691	−0.7514	0.3989	0.11*
H5'	0.5219	0.2625	0.2623	0.096*
H6	0.3934	−0.9145	0.445	0.13*
H6'	0.4394	0.4588	0.2681	0.107*
H7'	0.2134	0.5097	0.3133	0.117*
H7	0.5352	−0.9653	0.5152	0.144*
H8'	0.0548	0.368	0.3518	0.098*
H8	0.7531	−0.8523	0.5427	0.115*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N'	0.056 (2)	0.081 (3)	0.071 (3)	0.010 (2)	0.009 (2)	−0.006 (2)
N	0.089 (3)	0.082 (3)	0.062 (3)	0.008 (3)	−0.016 (2)	−0.010 (2)
C1'	0.064 (3)	0.083 (4)	0.091 (4)	0.008 (3)	0.004 (3)	0.000 (3)
C1	0.083 (3)	0.085 (4)	0.095 (4)	0.002 (4)	−0.020 (4)	−0.017 (3)
C2	0.085 (4)	0.075 (4)	0.105 (4)	0.003 (3)	−0.003 (4)	−0.009 (3)
C2'	0.091 (4)	0.068 (3)	0.096 (4)	−0.001 (3)	−0.015 (4)	0.000 (3)
C3'	0.069 (4)	0.091 (4)	0.062 (3)	0.015 (3)	−0.008 (3)	−0.017 (3)
C3	0.073 (3)	0.074 (4)	0.079 (4)	0.027 (3)	0.012 (3)	0.001 (3)
C4	0.057 (3)	0.083 (3)	0.069 (3)	0.020 (3)	0.002 (3)	−0.009 (3)
C4'	0.070 (3)	0.084 (4)	0.052 (3)	0.010 (3)	0.001 (3)	−0.002 (3)
C4A'	0.049 (3)	0.085 (4)	0.049 (2)	0.013 (3)	−0.003 (2)	−0.011 (3)
C4A	0.063 (3)	0.074 (3)	0.051 (3)	0.017 (3)	−0.007 (3)	−0.012 (3)
C4B'	0.056 (3)	0.076 (4)	0.056 (3)	0.004 (3)	−0.013 (3)	−0.003 (3)
C4B	0.062 (3)	0.079 (3)	0.065 (3)	0.014 (3)	0.001 (3)	−0.012 (3)
C5'	0.067 (3)	0.094 (4)	0.078 (3)	0.000 (3)	−0.004 (3)	0.007 (3)
C5	0.067 (4)	0.120 (5)	0.089 (4)	−0.005 (4)	−0.003 (3)	−0.018 (4)
C6'	0.086 (4)	0.086 (5)	0.094 (4)	−0.002 (3)	−0.017 (3)	0.016 (3)
C6	0.095 (4)	0.127 (5)	0.103 (5)	−0.030 (4)	0.015 (4)	−0.005 (4)
C7'	0.086 (4)	0.092 (4)	0.115 (5)	0.007 (4)	−0.014 (4)	−0.016 (4)
C7	0.127 (6)	0.105 (5)	0.127 (6)	−0.017 (5)	0.032 (5)	0.000 (5)
C8'	0.062 (3)	0.093 (4)	0.091 (4)	0.008 (3)	−0.003 (3)	−0.016 (3)
C8	0.114 (5)	0.094 (4)	0.080 (4)	0.017 (4)	0.013 (4)	0.002 (3)
C8A'	0.056 (3)	0.077 (3)	0.059 (3)	0.007 (3)	−0.006 (2)	−0.003 (3)
C8A	0.076 (3)	0.071 (4)	0.072 (3)	0.009 (3)	0.001 (3)	−0.012 (3)
C9A'	0.051 (3)	0.080 (4)	0.062 (3)	0.001 (3)	−0.005 (3)	−0.006 (3)
C9A	0.069 (3)	0.071 (3)	0.071 (3)	0.007 (3)	−0.013 (3)	−0.016 (3)
C10'	0.064 (3)	0.104 (4)	0.071 (3)	0.012 (3)	0.011 (3)	−0.005 (3)
C10	0.123 (5)	0.112 (5)	0.087 (4)	−0.003 (4)	−0.050 (4)	−0.010 (3)
C11'	0.062 (3)	0.175 (6)	0.119 (5)	−0.004 (4)	0.005 (4)	−0.042 (4)
C11	0.113 (5)	0.167 (7)	0.163 (6)	0.031 (6)	−0.061 (5)	−0.021 (6)
C12'	0.106 (4)	0.096 (4)	0.081 (4)	0.028 (4)	0.000 (3)	−0.016 (3)
C12	0.111 (5)	0.093 (4)	0.086 (4)	0.035 (4)	0.010 (3)	0.001 (3)
C13	0.148 (6)	0.094 (4)	0.085 (4)	0.064 (4)	−0.004 (4)	−0.001 (3)

Geometric parameters (Å, º)

N—C10	1.446 (6)	C6'—C7'	1.381 (8)
N'—C10'	1.459 (6)	C6—H6	0.93
N—C8A	1.389 (7)	C6'—H6'	0.93
N'—C9A'	1.367 (6)	C7—C8	1.376 (9)
N—C9A	1.396 (6)	C7—H7	0.93
C1—C2	1.356 (7)	C7'—H7'	0.93
C1'—C2'	1.373 (7)	C8'—C7'	1.367 (8)
C1'—C9A'	1.373 (6)	C8—H8	0.93
C1—H1	0.93	C8'—H8'	0.93
C1'—H1'	0.93	C8A—C4B	1.412 (7)
C2—H2	0.93	C8A—C8	1.365 (7)
C2'—H2'	0.93	C8A'—C8'	1.373 (6)
C3'—C12'	1.513 (7)	C8A'—N'	1.382 (5)
C3—C12	1.515 (7)	C9A—C1	1.384 (7)
C3—C2	1.391 (7)	C10—C11	1.493 (9)
C3'—C2'	1.409 (7)	C10'—C11'	1.515 (7)
C3'—C4'	1.366 (6)	C10'—H10A	0.97
C4—C3	1.369 (6)	C10'—H10B	0.97
C4'—C4A'	1.376 (6)	C10—H10C	0.97
C4—H4	0.93	C10—H10D	0.97
C4'—H4'	0.93	C11'—H11A	0.96
C4A—C4	1.378 (6)	C11'—H11B	0.96
C4A—C4B	1.433 (6)	C11'—H11C	0.96
C4A—C9A	1.408 (6)	C11—H11D	0.96
C4A'—C9A'	1.414 (6)	C11—H11E	0.96
C4B'—C4A'	1.441 (6)	C11—H11F	0.96
C4B—C5	1.394 (7)	C12—C13	1.532 (7)
C4B'—C5'	1.400 (7)	C12—H12A	0.97
C4B'—C8A'	1.408 (6)	C12—H12B	0.97
C5—C6	1.363 (8)	C12'—H12C	0.97
C5'—C6'	1.367 (7)	C12'—H12D	0.97
C5—H5	0.93	C13—C12'	1.459 (7)
C5'—H5'	0.93	C13—H13A	0.97
C6—C7	1.379 (9)	C13—H13B	0.97
N'—C10'—C11'	111.5 (4)	C6—C7—H7	119
N—C10—C11	112.9 (5)	C7—C6—C5	120.3 (6)
N'—C10'—H10A	109.3	C7'—C6'—H6'	119.5
N'—C10'—H10B	109.3	C7—C6—H6	119.8
N—C10—H10C	109	C7'—C8'—C8A'	117.6 (5)
N—C10—H10D	109	C7'—C8'—H8'	121.2
N—C8A—C4B	108.0 (5)	C7—C8—H8	121.3
N'—C8A'—C4B'	108.8 (4)	C8'—C7'—C6'	122.3 (6)
N'—C9A'—C1'	130.3 (5)	C8'—C7'—H7'	118.8
N—C9A—C4A	108.3 (5)	C8—C7—H7	119
N'—C9A'—C4A'	109.3 (4)	C8'—C8A'—C4B'	121.3 (5)
C1'—C2'—C3'	122.5 (5)	C8—C8A—C4B	122.2 (6)
C1—C2—C3	122.7 (6)	C8—C8A—N	129.8 (6)
C1—C2—H2	118.7	C8'—C8A'—N'	129.9 (5)
C1'—C2'—H2'	118.8	C8A'—C4B'—C4A'	106.7 (4)
C1'—C9A'—C4A'	120.3 (5)	C8A—C4B—C4A	107.5 (4)
C1—C9A—C4A	120.5 (5)	C8A—C8—C7	117.4 (6)
C1—C9A—N	131.2 (5)	C8A'—C8'—H8'	121.2
C2'—C1'—C9A'	118.0 (5)	C8A—C8—H8	121.3
C2—C1—C9A	118.3 (5)	C8A'—N'—C10'	125.3 (4)
C2—C1—H1	120.8	C8A—N—C10	125.7 (5)
C2'—C1'—H1'	121	C8A—N—C9A	109.1 (4)
C2'—C3'—C12'	119.5 (5)	C9A—C1—H1	120.8
C2—C3—C12	120.6 (6)	C9A'—C1'—H1'	121
C3—C12—C13	111.1 (5)	C9A'—C4A'—C4B'	106.1 (4)
C3—C12—H12A	109.4	C9A—C4A—C4B	106.9 (4)
C3—C12—H12B	109.4	C9A—N—C10	124.3 (5)
C3'—C12'—H12C	109.1	C9A'—N'—C10'	125.4 (4)
C3'—C12'—H12D	109.1	C9A'—N'—C8A'	109.0 (4)
C3—C2—H2	118.7	C10'—C11'—H11A	109.5
C3'—C2'—H2'	118.8	C10'—C11'—H11B	109.5
C3'—C4'—C4A'	119.9 (5)	C10'—C11'—H11C	109.5
C3—C4—H4	119.5	C10—C11—H11D	109.5
C3'—C4'—H4'	120	C10—C11—H11E	109.5
C4—C3—C12	120.6 (5)	C10—C11—H11F	109.5
C4'—C3'—C12'	121.7 (5)	C11'—C10'—H10A	109.3
C4—C3—C2	118.6 (5)	C11'—C10'—H10B	109.3
C4'—C3'—C2'	118.7 (5)	C11—C10—H10C	109
C4'—C4A'—C4B'	133.4 (5)	C11—C10—H10D	109
C4—C4A—C4B	134.0 (5)	C12'—C13—C12	116.5 (5)
C4—C4A—C9A	119.0 (5)	C12—C13—H13A	108.2
C4'—C4A'—C9A'	120.5 (5)	C12'—C13—H13A	108.2
C4A—C4—C3	120.9 (5)	C12—C13—H13B	108.2
C4A—C4—H4	119.5	C12'—C13—H13B	108.2
C4A'—C4'—H4'	120	C13—C12'—C3'	112.5 (4)
C4B—C5—H5	120.1	C13—C12—H12A	109.4
C4B'—C5'—H5'	120.9	C13—C12—H12B	109.4
C5'—C4B'—C4A'	133.5 (5)	C13—C12'—H12C	109.1
C5—C4B—C4A	134.3 (5)	C13—C12'—H12D	109.1
C5—C4B—C8A	118.2 (5)	H10A—C10'—H10B	108
C5'—C4B'—C8A'	119.7 (5)	H10C—C10—H10D	107.8
C5'—C6'—C7'	120.9 (6)	H11A—C11'—H11B	109.5
C5'—C6'—H6'	119.5	H11A—C11'—H11C	109.5
C5—C6—H6	119.8	H11B—C11'—H11C	109.5
C6'—C5'—C4B'	118.1 (5)	H11D—C11—H11E	109.5
C6—C5—C4B	119.7 (6)	H11D—C11—H11F	109.5
C6—C5—H5	120.1	H11E—C11—H11F	109.5
C6'—C5'—H5'	120.9	H12A—C12—H12B	108
C6—C7—C8	122.1 (7)	H12C—C12'—H12D	107.8
C6'—C7'—H7'	118.8	H13A—C13—H13B	107.3
N—C8A—C4B—C4A	2.7 (5)	C5'—C4B'—C4A'—C4'	1.8 (8)
N—C8A—C4B—C5	−177.8 (4)	C5'—C4B'—C4A'—C9A'	179.8 (5)
N'—C8A'—C8'—C7'	178.8 (5)	C5'—C4B'—C8A'—C8'	−0.3 (7)
N—C8A—C8—C7	179.1 (5)	C5'—C4B'—C8A'—N'	−179.2 (4)
N—C9A—C1—C2	−179.1 (5)	C5—C6—C7—C8	0.9 (10)
C2'—C1'—C9A'—C4A'	1.4 (7)	C5'—C6'—C7'—C8'	−1.2 (8)
C2'—C1'—C9A'—N'	−176.5 (5)	C6—C7—C8—C8A	−1.5 (9)
C2'—C3'—C12'—C13	−64.0 (7)	C8—C8A—C4B—C4A	−178.5 (4)
C2—C3—C12—C13	−97.3 (6)	C8—C8A—C4B—C5	1.1 (7)
C2'—C3'—C4'—C4A'	3.0 (6)	C8'—C8A'—N'—C10'	6.7 (7)
C3—C12—C13—C12'	−158.6 (6)	C8'—C8A'—N'—C9A'	−179.5 (5)
C3'—C4'—C4A'—C4B'	177.0 (5)	C8A'—C4B'—C4A'—C4'	−177.1 (4)
C3'—C4'—C4A'—C9A'	−0.9 (6)	C8A'—C4B'—C4A'—C9A'	1.0 (5)
C4'—C3'—C12'—C13	113.8 (6)	C8A'—C4B'—C5'—C6'	−0.4 (7)
C4—C3—C12—C13	77.5 (6)	C8A—C4B—C5—C6	−1.8 (7)
C4—C3—C2—C1	2.7 (8)	C8A'—C8'—C7'—C6'	0.5 (8)
C4'—C3'—C2'—C1'	−3.1 (7)	C8A—N—C10—C11	84.1 (7)
C4—C4A—C4B—C5	−1.0 (9)	C8A'—N'—C10'—C11'	90.1 (6)
C4—C4A—C4B—C8A	178.5 (5)	C8A—N—C9A—C1	−177.9 (5)
C4—C4A—C9A—C1	−0.5 (6)	C8A'—N'—C9A'—C1'	179.5 (5)
C4'—C4A'—C9A'—C1'	−1.4 (7)	C8A'—N'—C9A'—C4A'	1.4 (5)
C4'—C4A'—C9A'—N'	176.9 (4)	C8A—N—C9A—C4A	1.7 (5)
C4—C4A—C9A—N	179.9 (4)	C9A'—C1'—C2'—C3'	0.8 (7)
C4A—C4—C3—C12	−176.6 (4)	C9A—C1—C2—C3	−2.6 (8)
C4A—C4—C3—C2	−1.6 (7)	C9A—C4A—C4—C3	0.6 (6)
C4A—C4B—C5—C6	177.6 (5)	C9A—C4A—C4B—C5	178.9 (5)
C4A'—C4B'—C5'—C6'	−179.1 (5)	C9A—C4A—C4B—C8A	−1.7 (5)
C4A'—C4B'—C8A'—C8'	178.7 (4)	C9A'—N'—C10'—C11'	−82.7 (6)
C4A'—C4B'—C8A'—N'	−0.2 (5)	C9A—N—C10—C11	−84.2 (7)
C4A—C9A—C1—C2	1.4 (7)	C9A—N—C8A—C4B	−2.7 (5)
C4B—C4A—C4—C3	−179.6 (5)	C9A—N—C8A—C8	178.6 (5)
C4B—C4A—C9A—C1	179.6 (4)	C10—N—C8A—C4B	−172.5 (5)
C4B'—C4A'—C9A'—C1'	−179.8 (4)	C10—N—C8A—C8	8.7 (8)
C4B—C4A—C9A—N	0.0 (5)	C10'—N'—C9A'—C1'	−6.7 (8)
C4B'—C4A'—C9A'—N'	−1.5 (5)	C10—N—C9A—C1	−7.9 (8)
C4B—C5—C6—C7	0.9 (9)	C10—N—C9A—C4A	171.6 (5)
C4B'—C5'—C6'—C7'	1.1 (8)	C10'—N'—C9A'—C4A'	175.2 (4)
C4B'—C8A'—C8'—C7'	0.2 (7)	C12—C13—C12'—C3'	−176.9 (5)
C4B—C8A—C8—C7	0.5 (7)	C12'—C3'—C2'—C1'	174.8 (5)
C4B'—C8A'—N'—C10'	−174.6 (4)	C12—C3—C2—C1	177.7 (5)
C4B'—C8A'—N'—C9A'	−0.8 (5)	C12'—C3'—C4'—C4A'	−174.8 (4)