N,N-Bis­(anthracen-9-yl­methyl)­propyl­amine

The title compound, C₃₃H₂₉N, was obtained by the reaction of 9-chloro­methyl­anthracene and n-propyl­amine. Two anthra­cenyl­methyl units are linked to the N atom of n-propyl­amine and the dihedral angle between the two anthracene systems is 64.3 (2)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.077
• wR factor = 0.208
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) .......          3

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.881     0.990
            Tmin' and Tmax expected:      0.978     0.986
            RR' =      0.898
            Please check that your absorption correction is appropriate.
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         41 Perc.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.90
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C24
PLAT301_ALERT_3_C Main Residue  Disorder .........................       8.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT410_ALERT_2_C Short Intra H...H Contact  H2A    ..  H15B    ..       1.98 Ang.
PLAT410_ALERT_2_C Short Intra H...H Contact  H19B   ..  H32A    ..       1.95 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      19.00 Deg.
              C16' -N1   -C16     1.555   1.555   1.555

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

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

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

N,N-Bis(anthracen-9-ylmethyl)propylamine

Crystal data

C33H29N	F(000) = 468
Mr = 439.57	Dx = 1.193 Mg m^−3
Triclinic, P1	Melting point: 282 K
a = 9.891 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.188 (4) Å	Cell parameters from 689 reflections
c = 13.592 (5) Å	θ = 2.3–22.3°
α = 106.179 (7)°	µ = 0.07 mm^−1
β = 106.822 (7)°	T = 293 K
γ = 97.750 (7)°	Block, yellow
V = 1224.1 (7) Å^3	0.32 × 0.24 × 0.20 mm
Z = 2

Data collection

Bruker SMART1000 CCD area-detector diffractometer	4975 independent reflections
Radiation source: fine-focus sealed tube	2036 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
φ and ω scans	θmax = 26.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→12
Tmin = 0.881, Tmax = 0.990	k = −12→9
7130 measured reflections	l = −15→17

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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.208	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0803P)^2] where P = (Fo^2 + 2Fc^2)/3
4975 reflections	(Δ/σ)max < 0.001
305 parameters	Δρmax = 0.23 e Å^−3
3 restraints	Δρmin = −0.23 e Å^−3

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. Disorder prsent in n-Pr group, modelled over 2 sites with isotropic adps, distance restraints and occupancies 0.621 (14) and 0.379 (14).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.6097 (3)	0.1547 (2)	0.33354 (18)	0.0464 (7)
C1	0.7259 (4)	0.2229 (3)	0.1282 (2)	0.0462 (8)
C2	0.8757 (4)	0.2315 (4)	0.1809 (3)	0.0620 (10)
H2A	0.9012	0.1907	0.2349	0.074*
C3	0.9818 (4)	0.2969 (4)	0.1549 (3)	0.0776 (12)
H3A	1.0783	0.2991	0.1903	0.093*
C4	0.9482 (5)	0.3612 (5)	0.0755 (3)	0.0861 (14)
H4A	1.0219	0.4063	0.0583	0.103*
C5	0.8094 (5)	0.3576 (4)	0.0242 (3)	0.0745 (12)
H5A	0.7884	0.4015	−0.0281	0.089*
C6	0.6936 (4)	0.2893 (3)	0.0470 (2)	0.0532 (9)
C7	0.5511 (4)	0.2856 (3)	−0.0067 (3)	0.0589 (10)
H7A	0.5310	0.3300	−0.0587	0.071*
C8	0.4370 (4)	0.2182 (3)	0.0140 (2)	0.0515 (9)
C9	0.2915 (4)	0.2146 (4)	−0.0421 (3)	0.0714 (11)
H9A	0.2714	0.2584	−0.0945	0.086*
C10	0.1821 (4)	0.1492 (5)	−0.0213 (3)	0.0813 (13)
H10A	0.0867	0.1472	−0.0593	0.098*
C11	0.2112 (4)	0.0834 (4)	0.0581 (3)	0.0759 (12)
H11A	0.1345	0.0388	0.0727	0.091*
C12	0.3484 (4)	0.0840 (4)	0.1135 (3)	0.0575 (9)
H12A	0.3650	0.0386	0.1650	0.069*
C13	0.4675 (3)	0.1524 (3)	0.0945 (2)	0.0442 (8)
C14	0.6120 (3)	0.1543 (3)	0.1515 (2)	0.0431 (8)
C15	0.6398 (4)	0.0822 (3)	0.2356 (2)	0.0486 (9)
H15A	0.5796	−0.0128	0.2033	0.058*
H15B	0.7405	0.0760	0.2565	0.058*
C19	0.6103 (4)	0.0668 (3)	0.4028 (2)	0.0530 (9)
H19A	0.6000	0.1214	0.4701	0.064*
H19B	0.7036	0.0422	0.4216	0.064*
C20	0.4920 (4)	−0.0663 (3)	0.3508 (2)	0.0473 (8)
C21	0.3473 (4)	−0.0585 (4)	0.3389 (2)	0.0542 (9)
C22	0.3068 (5)	0.0703 (4)	0.3711 (3)	0.0691 (11)
H22A	0.3772	0.1542	0.3989	0.083*
C23	0.1669 (5)	0.0744 (5)	0.3625 (3)	0.0877 (13)
H23A	0.1433	0.1603	0.3858	0.105*
C24	0.0596 (6)	−0.0490 (7)	0.3191 (4)	0.1057 (17)
H24A	−0.0358	−0.0450	0.3128	0.127*
C25	0.0913 (5)	−0.1734 (6)	0.2863 (4)	0.0925 (15)
H25A	0.0174	−0.2548	0.2569	0.111*
C26	0.2338 (4)	−0.1839 (4)	0.2952 (3)	0.0629 (10)
C27	0.2708 (5)	−0.3111 (4)	0.2641 (3)	0.0733 (12)
H27A	0.1972	−0.3927	0.2355	0.088*
C28	0.4087 (5)	−0.3241 (4)	0.2729 (3)	0.0619 (10)
C29	0.4431 (6)	−0.4569 (4)	0.2391 (3)	0.0849 (14)
H29A	0.3694	−0.5384	0.2105	0.102*
C30	0.5777 (7)	−0.4669 (5)	0.2475 (4)	0.0964 (16)
H30A	0.5970	−0.5548	0.2236	0.116*
C31	0.6909 (6)	−0.3464 (6)	0.2920 (3)	0.0895 (14)
H31A	0.7853	−0.3547	0.2984	0.107*
C32	0.6641 (5)	−0.2172 (4)	0.3258 (3)	0.0724 (11)
H32A	0.7412	−0.1385	0.3553	0.087*
C33	0.5234 (4)	−0.1984 (4)	0.3179 (2)	0.0539 (9)
C16	0.7425 (12)	0.2746 (10)	0.3940 (8)	0.060 (4)*	0.379 (14)
H16A	0.8247	0.2398	0.4268	0.072*	0.379 (14)
H16B	0.7661	0.3172	0.3437	0.072*	0.379 (14)
C17	0.7123 (17)	0.3819 (9)	0.4811 (8)	0.070 (4)*	0.379 (14)
H17A	0.6920	0.3395	0.5325	0.085*	0.379 (14)
H17B	0.6271	0.4128	0.4482	0.085*	0.379 (14)
C18	0.8415 (19)	0.5082 (12)	0.5414 (10)	0.104 (5)*	0.379 (14)
H18A	0.8177	0.5776	0.5937	0.155*	0.379 (14)
H18B	0.8641	0.5478	0.4901	0.155*	0.379 (14)
H18C	0.9240	0.4788	0.5785	0.155*	0.379 (14)
C17'	0.6394 (10)	0.3885 (6)	0.4702 (5)	0.064 (2)*	0.621 (14)
H17C	0.6126	0.3420	0.5175	0.077*	0.621 (14)
H17D	0.5523	0.4066	0.4260	0.077*	0.621 (14)
C18'	0.7495 (11)	0.5270 (7)	0.5392 (5)	0.088 (3)*	0.621 (14)
H18D	0.7073	0.5867	0.5839	0.132*	0.621 (14)
H18E	0.7766	0.5725	0.4924	0.132*	0.621 (14)
H18F	0.8341	0.5093	0.5850	0.132*	0.621 (14)
C16'	0.7009 (8)	0.2946 (5)	0.3976 (4)	0.0445 (19)*	0.621 (14)
H16C	0.7215	0.3403	0.3481	0.053*	0.621 (14)
H16D	0.7927	0.2852	0.4425	0.053*	0.621 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0668 (19)	0.0358 (15)	0.0322 (13)	0.0034 (13)	0.0131 (13)	0.0128 (12)
C1	0.055 (2)	0.0404 (19)	0.0383 (17)	0.0050 (16)	0.0173 (16)	0.0076 (15)
C2	0.056 (2)	0.074 (3)	0.055 (2)	0.007 (2)	0.0191 (19)	0.022 (2)
C3	0.053 (3)	0.102 (3)	0.068 (3)	0.000 (2)	0.018 (2)	0.024 (2)
C4	0.076 (3)	0.112 (4)	0.065 (3)	−0.016 (3)	0.027 (2)	0.035 (3)
C5	0.080 (3)	0.087 (3)	0.052 (2)	−0.008 (2)	0.021 (2)	0.031 (2)
C6	0.063 (2)	0.055 (2)	0.0409 (18)	0.0008 (18)	0.0209 (17)	0.0190 (17)
C7	0.075 (3)	0.064 (2)	0.0423 (19)	0.013 (2)	0.0195 (19)	0.0257 (18)
C8	0.057 (2)	0.057 (2)	0.0379 (18)	0.0114 (18)	0.0136 (17)	0.0159 (17)
C9	0.071 (3)	0.096 (3)	0.051 (2)	0.025 (2)	0.015 (2)	0.034 (2)
C10	0.051 (3)	0.124 (4)	0.068 (3)	0.021 (2)	0.014 (2)	0.037 (3)
C11	0.054 (3)	0.108 (3)	0.061 (2)	0.005 (2)	0.018 (2)	0.030 (2)
C12	0.056 (2)	0.068 (2)	0.0454 (19)	0.0042 (19)	0.0150 (17)	0.0212 (18)
C13	0.050 (2)	0.0437 (19)	0.0340 (17)	0.0057 (16)	0.0130 (15)	0.0098 (15)
C14	0.055 (2)	0.0368 (18)	0.0350 (16)	0.0044 (16)	0.0170 (16)	0.0093 (14)
C15	0.061 (2)	0.0408 (19)	0.0451 (18)	0.0092 (16)	0.0191 (16)	0.0161 (16)
C19	0.066 (2)	0.048 (2)	0.0442 (18)	0.0073 (17)	0.0142 (16)	0.0226 (17)
C20	0.065 (2)	0.041 (2)	0.0373 (17)	0.0058 (17)	0.0175 (16)	0.0178 (16)
C21	0.068 (3)	0.061 (2)	0.0409 (18)	0.014 (2)	0.0186 (18)	0.0278 (18)
C22	0.080 (3)	0.073 (3)	0.061 (2)	0.018 (2)	0.025 (2)	0.032 (2)
C23	0.080 (3)	0.111 (4)	0.090 (3)	0.040 (3)	0.034 (3)	0.047 (3)
C24	0.073 (4)	0.143 (5)	0.118 (4)	0.032 (4)	0.032 (3)	0.067 (4)
C25	0.064 (3)	0.117 (4)	0.092 (3)	0.003 (3)	0.015 (3)	0.049 (3)
C26	0.062 (3)	0.075 (3)	0.047 (2)	−0.001 (2)	0.0112 (19)	0.029 (2)
C27	0.088 (3)	0.066 (3)	0.049 (2)	−0.014 (2)	0.011 (2)	0.023 (2)
C28	0.098 (3)	0.047 (2)	0.0401 (19)	0.006 (2)	0.024 (2)	0.0186 (18)
C29	0.143 (5)	0.050 (3)	0.056 (2)	0.010 (3)	0.031 (3)	0.018 (2)
C30	0.159 (5)	0.076 (4)	0.074 (3)	0.051 (4)	0.050 (4)	0.035 (3)
C31	0.111 (4)	0.105 (4)	0.084 (3)	0.050 (3)	0.050 (3)	0.051 (3)
C32	0.104 (4)	0.063 (3)	0.075 (3)	0.033 (2)	0.044 (2)	0.039 (2)
C33	0.078 (3)	0.051 (2)	0.0399 (18)	0.012 (2)	0.0233 (18)	0.0246 (17)

Geometric parameters (Å, º)

N1—C16'	1.453 (5)	C22—C23	1.362 (5)
N1—C15	1.465 (4)	C22—H22A	0.9300
N1—C19	1.469 (3)	C23—C24	1.385 (6)
N1—C16	1.508 (7)	C23—H23A	0.9300
C1—C14	1.405 (4)	C24—C25	1.333 (6)
C1—C2	1.426 (4)	C24—H24A	0.9300
C1—C6	1.431 (4)	C25—C26	1.400 (5)
C2—C3	1.352 (5)	C25—H25A	0.9300
C2—H2A	0.9300	C26—C27	1.380 (5)
C3—C4	1.397 (5)	C27—C28	1.363 (5)
C3—H3A	0.9300	C27—H27A	0.9300
C4—C5	1.338 (5)	C28—C29	1.423 (5)
C4—H4A	0.9300	C28—C33	1.440 (5)
C5—C6	1.416 (5)	C29—C30	1.323 (6)
C5—H5A	0.9300	C29—H29A	0.9300
C6—C7	1.377 (4)	C30—C31	1.397 (6)
C7—C8	1.381 (5)	C30—H30A	0.9300
C7—H7A	0.9300	C31—C32	1.357 (5)
C8—C9	1.411 (5)	C31—H31A	0.9300
C8—C13	1.417 (4)	C32—C33	1.408 (5)
C9—C10	1.335 (5)	C32—H32A	0.9300
C9—H9A	0.9300	C16—C17	1.503 (9)
C10—C11	1.404 (5)	C16—H16A	0.9700
C10—H10A	0.9300	C16—H16B	0.9700
C11—C12	1.347 (4)	C17—C18	1.524 (9)
C11—H11A	0.9300	C17—H17A	0.9700
C12—C13	1.413 (4)	C17—H17B	0.9700
C12—H12A	0.9300	C18—H18A	0.9600
C13—C14	1.409 (4)	C18—H18B	0.9600
C14—C15	1.504 (4)	C18—H18C	0.9600
C15—H15A	0.9700	C17'—C16'	1.496 (7)
C15—H15B	0.9700	C17'—C18'	1.521 (7)
C19—C20	1.505 (4)	C17'—H17C	0.9700
C19—H19A	0.9700	C17'—H17D	0.9700
C19—H19B	0.9700	C18'—H18D	0.9600
C20—C33	1.402 (4)	C18'—H18E	0.9600
C20—C21	1.409 (5)	C18'—H18F	0.9600
C21—C22	1.414 (5)	C16'—H16C	0.9700
C21—C26	1.431 (5)	C16'—H16D	0.9700
C16'—N1—C15	115.9 (4)	C22—C23—C24	120.3 (5)
C16'—N1—C19	110.5 (3)	C22—C23—H23A	119.9
C15—N1—C19	111.0 (2)	C24—C23—H23A	119.9
C16'—N1—C16	19.0 (5)	C25—C24—C23	120.8 (5)
C15—N1—C16	102.2 (5)	C25—C24—H24A	119.6
C19—N1—C16	106.5 (5)	C23—C24—H24A	119.6
C14—C1—C2	124.1 (3)	C24—C25—C26	121.3 (5)
C14—C1—C6	119.6 (3)	C24—C25—H25A	119.4
C2—C1—C6	116.3 (3)	C26—C25—H25A	119.4
C3—C2—C1	122.1 (4)	C27—C26—C25	122.7 (4)
C3—C2—H2A	118.9	C27—C26—C21	117.8 (4)
C1—C2—H2A	118.9	C25—C26—C21	119.4 (4)
C2—C3—C4	120.7 (4)	C28—C27—C26	123.9 (4)
C2—C3—H3A	119.6	C28—C27—H27A	118.1
C4—C3—H3A	119.6	C26—C27—H27A	118.1
C5—C4—C3	119.7 (4)	C27—C28—C29	122.5 (4)
C5—C4—H4A	120.2	C27—C28—C33	118.5 (4)
C3—C4—H4A	120.2	C29—C28—C33	119.1 (4)
C4—C5—C6	122.1 (4)	C30—C29—C28	121.4 (5)
C4—C5—H5A	118.9	C30—C29—H29A	119.3
C6—C5—H5A	118.9	C28—C29—H29A	119.3
C7—C6—C5	121.6 (3)	C29—C30—C31	120.5 (5)
C7—C6—C1	119.3 (3)	C29—C30—H30A	119.7
C5—C6—C1	119.0 (3)	C31—C30—H30A	119.7
C6—C7—C8	122.2 (3)	C32—C31—C30	120.4 (5)
C6—C7—H7A	118.9	C32—C31—H31A	119.8
C8—C7—H7A	118.9	C30—C31—H31A	119.8
C7—C8—C9	121.6 (3)	C31—C32—C33	122.2 (4)
C7—C8—C13	119.0 (3)	C31—C32—H32A	118.9
C9—C8—C13	119.4 (3)	C33—C32—H32A	118.9
C10—C9—C8	121.0 (4)	C20—C33—C32	123.5 (3)
C10—C9—H9A	119.5	C20—C33—C28	120.1 (4)
C8—C9—H9A	119.5	C32—C33—C28	116.4 (4)
C9—C10—C11	120.0 (4)	C17—C16—N1	109.0 (7)
C9—C10—H10A	120.0	C17—C16—H16A	109.9
C11—C10—H10A	120.0	N1—C16—H16A	109.9
C12—C11—C10	121.0 (4)	C17—C16—H16B	109.9
C12—C11—H11A	119.5	N1—C16—H16B	109.9
C10—C11—H11A	119.5	H16A—C16—H16B	108.3
C11—C12—C13	121.0 (3)	C16—C17—C18	110.9 (9)
C11—C12—H12A	119.5	C16—C17—H17A	109.5
C13—C12—H12A	119.5	C18—C17—H17A	109.5
C14—C13—C12	122.0 (3)	C16—C17—H17B	109.5
C14—C13—C8	120.5 (3)	C18—C17—H17B	109.5
C12—C13—C8	117.6 (3)	H17A—C17—H17B	108.0
C1—C14—C13	119.4 (3)	C17—C18—H18A	109.5
C1—C14—C15	121.8 (3)	C17—C18—H18B	109.5
C13—C14—C15	118.9 (3)	H18A—C18—H18B	109.5
N1—C15—C14	113.3 (2)	C17—C18—H18C	109.5
N1—C15—H15A	108.9	H18A—C18—H18C	109.5
C14—C15—H15A	108.9	H18B—C18—H18C	109.5
N1—C15—H15B	108.9	C16'—C17'—C18'	110.7 (6)
C14—C15—H15B	108.9	C16'—C17'—H17C	109.5
H15A—C15—H15B	107.7	C18'—C17'—H17C	109.5
N1—C19—C20	114.0 (2)	C16'—C17'—H17D	109.5
N1—C19—H19A	108.7	C18'—C17'—H17D	109.5
C20—C19—H19A	108.7	H17C—C17'—H17D	108.1
N1—C19—H19B	108.7	C17'—C18'—H18D	109.5
C20—C19—H19B	108.7	C17'—C18'—H18E	109.5
H19A—C19—H19B	107.6	H18D—C18'—H18E	109.5
C33—C20—C21	119.2 (3)	C17'—C18'—H18F	109.5
C33—C20—C19	121.4 (3)	H18D—C18'—H18F	109.5
C21—C20—C19	119.3 (3)	H18E—C18'—H18F	109.5
C20—C21—C22	122.7 (3)	N1—C16'—C17'	115.8 (5)
C20—C21—C26	120.5 (4)	N1—C16'—H16C	108.3
C22—C21—C26	116.7 (4)	C17'—C16'—H16C	108.3
C23—C22—C21	121.4 (4)	N1—C16'—H16D	108.3
C23—C22—H22A	119.3	C17'—C16'—H16D	108.3
C21—C22—H22A	119.3	H16C—C16'—H16D	107.4
C14—C1—C2—C3	179.1 (3)	N1—C19—C20—C21	−72.8 (4)
C6—C1—C2—C3	−0.8 (5)	C33—C20—C21—C22	179.3 (3)
C1—C2—C3—C4	1.0 (6)	C19—C20—C21—C22	1.9 (4)
C2—C3—C4—C5	−0.3 (6)	C33—C20—C21—C26	0.9 (4)
C3—C4—C5—C6	−0.5 (6)	C19—C20—C21—C26	−176.6 (3)
C4—C5—C6—C7	−179.6 (4)	C20—C21—C22—C23	−177.5 (3)
C4—C5—C6—C1	0.6 (6)	C26—C21—C22—C23	1.0 (5)
C14—C1—C6—C7	0.4 (4)	C21—C22—C23—C24	−1.5 (6)
C2—C1—C6—C7	−179.7 (3)	C22—C23—C24—C25	0.7 (7)
C14—C1—C6—C5	−179.8 (3)	C23—C24—C25—C26	0.4 (7)
C2—C1—C6—C5	0.1 (4)	C24—C25—C26—C27	178.6 (4)
C5—C6—C7—C8	179.4 (3)	C24—C25—C26—C21	−0.9 (6)
C1—C6—C7—C8	−0.8 (5)	C20—C21—C26—C27	−0.8 (5)
C6—C7—C8—C9	−179.6 (3)	C22—C21—C26—C27	−179.4 (3)
C6—C7—C8—C13	1.0 (5)	C20—C21—C26—C25	178.7 (3)
C7—C8—C9—C10	−180.0 (4)	C22—C21—C26—C25	0.1 (5)
C13—C8—C9—C10	−0.5 (5)	C25—C26—C27—C28	−179.3 (4)
C8—C9—C10—C11	0.4 (6)	C21—C26—C27—C28	0.1 (5)
C9—C10—C11—C12	−0.6 (6)	C26—C27—C28—C29	−179.4 (3)
C10—C11—C12—C13	0.9 (6)	C26—C27—C28—C33	0.5 (5)
C11—C12—C13—C14	180.0 (3)	C27—C28—C29—C30	179.4 (4)
C11—C12—C13—C8	−0.9 (5)	C33—C28—C29—C30	−0.5 (6)
C7—C8—C13—C14	−0.7 (5)	C28—C29—C30—C31	1.2 (7)
C9—C8—C13—C14	179.9 (3)	C29—C30—C31—C32	−0.9 (7)
C7—C8—C13—C12	−179.8 (3)	C30—C31—C32—C33	−0.1 (6)
C9—C8—C13—C12	0.8 (5)	C21—C20—C33—C32	179.7 (3)
C2—C1—C14—C13	179.9 (3)	C19—C20—C33—C32	−2.9 (4)
C6—C1—C14—C13	−0.2 (4)	C21—C20—C33—C28	−0.2 (4)
C2—C1—C14—C15	−0.3 (5)	C19—C20—C33—C28	177.2 (3)
C6—C1—C14—C15	179.6 (3)	C31—C32—C33—C20	−179.1 (3)
C12—C13—C14—C1	179.4 (3)	C31—C32—C33—C28	0.8 (5)
C8—C13—C14—C1	0.3 (4)	C27—C28—C33—C20	−0.4 (4)
C12—C13—C14—C15	−0.4 (4)	C29—C28—C33—C20	179.4 (3)
C8—C13—C14—C15	−179.5 (3)	C27—C28—C33—C32	179.7 (3)
C16'—N1—C15—C14	−64.1 (4)	C29—C28—C33—C32	−0.5 (4)
C19—N1—C15—C14	168.7 (2)	C16'—N1—C16—C17	26.3 (14)
C16—N1—C15—C14	−78.1 (6)	C15—N1—C16—C17	164.7 (7)
C1—C14—C15—N1	110.1 (3)	C19—N1—C16—C17	−78.8 (9)
C13—C14—C15—N1	−70.2 (3)	N1—C16—C17—C18	−177.6 (9)
C16'—N1—C19—C20	165.7 (4)	C15—N1—C16'—C17'	157.9 (4)
C15—N1—C19—C20	−64.3 (4)	C19—N1—C16'—C17'	−74.7 (6)
C16—N1—C19—C20	−174.7 (6)	C16—N1—C16'—C17'	−156 (2)
N1—C19—C20—C33	109.8 (3)	C18'—C17'—C16'—N1	175.5 (5)