6-Bromo-2-(diprop-2-ynyl-amino)-1H-benzo[de]isoquinoline-1,3(2H)-dione.

The asymmetric unit of the title compound, C(18)H(11)BrN(2)O(2), contains two independent mol-ecules in which the prop-2-ynyl-amino groups have different mutual orientations. In one mol-ecule, the Br atom is disordered over two positions, with refined occupancies of 0.742 (2) and 0.258 (2).

Related literature

For the applications and biological activity of naphthalimide compounds, see: Muth et al. (2007 ▶); Zhang & Zhou (2011 ▶); Zhang et al. (2011 ▶). For the synthesis, see: Wang et al. (2010 ▶).

Experimental

Crystal data

C18H11BrN2O2

M = 367.20

Triclinic,

a = 10.460 (3) Å

b = 11.816 (3) Å

c = 13.561 (3) Å

α = 75.128 (4)°

β = 75.725 (4)°

γ = 72.298 (4)°

V = 1517.2 (7) Å3

Z = 4

Mo Kα radiation

μ = 2.72 mm−1

T = 296 K

0.26 × 0.24 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.538, T max = 0.640

8441 measured reflections

5901 independent reflections

3709 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.189

S = 1.04

5901 reflections

425 parameters

1 restraint

H-atom parameters constrained

Δρmax = 2.20 e Å−3

Δρmin = −0.74 e Å−3

Data collection: APEX2 (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812022507/lh5464sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022507/lh5464Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812022507/lh5464Isup3.cml

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

C18H11BrN2O2	Z = 4
Mr = 367.20	F(000) = 736
Triclinic, P1	Dx = 1.608 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.460 (3) Å	Cell parameters from 1880 reflections
b = 11.816 (3) Å	θ = 2.4–23.5°
c = 13.561 (3) Å	µ = 2.72 mm−1
α = 75.128 (4)°	T = 296 K
β = 75.725 (4)°	Block, yellow
γ = 72.298 (4)°	0.26 × 0.24 × 0.18 mm
V = 1517.2 (7) Å3

Bruker APEXII CCD diffractometer	5901 independent reflections
Radiation source: fine-focus sealed tube	3709 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→12
Tmin = 0.538, Tmax = 0.640	k = −12→14
8441 measured reflections	l = −14→16

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0813P)2 + 2.8703P] where P = (Fo2 + 2Fc2)/3
5901 reflections	(Δ/σ)max < 0.001
425 parameters	Δρmax = 2.20 e Å−3
1 restraint	Δρmin = −0.74 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br2	0.55459 (14)	0.50977 (11)	0.76724 (11)	0.0989 (5)	0.742 (2)
C19	0.6750 (6)	0.5968 (6)	0.7825 (5)	0.0631 (18)
C27	0.4943 (7)	0.6809 (6)	0.9230 (5)	0.0630 (18)
H27	0.4352	0.6387	0.9177	0.076*	0.742 (2)
Br2'	0.3819 (3)	0.5988 (3)	0.9048 (3)	0.0711 (11)	0.258 (2)
H19'	0.6195	0.5535	0.7732	0.076*	0.258 (2)
O3	1.0432 (4)	0.7900 (4)	0.7554 (3)	0.0576 (11)
O4	0.7320 (4)	0.9391 (4)	1.0192 (3)	0.0579 (11)
N3	0.8868 (4)	0.8680 (4)	0.8839 (3)	0.0391 (10)
N4	0.9653 (5)	0.9410 (4)	0.8921 (3)	0.0429 (11)
C20	0.7978 (8)	0.5865 (6)	0.7231 (5)	0.0658 (18)
H20A	0.8266	0.5359	0.6751	0.079*
C21	0.8830 (7)	0.6511 (6)	0.7325 (5)	0.0554 (16)
H21A	0.9684	0.6451	0.6899	0.067*
C22	0.8417 (6)	0.7239 (5)	0.8044 (4)	0.0440 (13)
C23	0.7107 (5)	0.7359 (5)	0.8683 (4)	0.0398 (12)
C24	0.6694 (5)	0.8110 (5)	0.9422 (4)	0.0384 (12)
C25	0.5441 (6)	0.8219 (6)	1.0036 (4)	0.0512 (15)
H25A	0.5160	0.8725	1.0516	0.061*
C26	0.4565 (6)	0.7562 (6)	0.9943 (5)	0.0622 (18)
H26A	0.3711	0.7637	1.0372	0.075*
C28	0.6227 (6)	0.6695 (5)	0.8594 (5)	0.0506 (15)
C29	0.9338 (6)	0.7938 (5)	0.8102 (4)	0.0415 (13)
C30	0.7610 (5)	0.8777 (5)	0.9544 (4)	0.0416 (13)
C31	1.0955 (6)	0.8715 (6)	0.9279 (5)	0.0524 (15)
H31A	1.1567	0.8304	0.8741	0.063*
H31B	1.1389	0.9269	0.9406	0.063*
C32	1.0719 (6)	0.7828 (6)	1.0224 (5)	0.0516 (15)
C33	1.0549 (7)	0.7110 (6)	1.0983 (5)	0.0650 (18)
H33	1.0414	0.6537	1.1587	0.078*
C34	0.9868 (6)	1.0320 (5)	0.7990 (5)	0.0529 (15)
H34A	1.0319	1.0855	0.8126	0.063*
H34B	1.0468	0.9922	0.7440	0.063*
C35	0.8608 (7)	1.1035 (6)	0.7643 (5)	0.0513 (15)
C36	0.7616 (8)	1.1615 (7)	0.7340 (6)	0.073 (2)
H36	0.6821	1.2079	0.7098	0.088*
Br1	0.59705 (8)	0.00106 (6)	0.23760 (5)	0.0651 (3)
O1	0.5025 (4)	0.3271 (4)	0.6119 (4)	0.0619 (12)
O2	0.0699 (4)	0.2945 (4)	0.6614 (3)	0.0534 (10)
N1	0.2845 (4)	0.3213 (4)	0.6295 (3)	0.0384 (10)
N2	0.2348 (5)	0.4032 (4)	0.6985 (3)	0.0411 (10)
C1	0.5383 (7)	0.0905 (5)	0.3449 (4)	0.0507 (15)
C2	0.6289 (6)	0.1396 (6)	0.3650 (4)	0.0513 (15)
H2A	0.7169	0.1289	0.3260	0.062*
C3	0.5900 (6)	0.2068 (5)	0.4446 (5)	0.0526 (15)
H3A	0.6525	0.2389	0.4593	0.063*
C4	0.4603 (6)	0.2243 (5)	0.4999 (4)	0.0431 (13)
C5	0.3643 (6)	0.1758 (4)	0.4791 (4)	0.0412 (13)
C6	0.2311 (6)	0.1948 (5)	0.5347 (4)	0.0417 (13)
C7	0.1384 (6)	0.1445 (5)	0.5174 (4)	0.0500 (14)
H7A	0.0501	0.1577	0.5557	0.060*
C8	0.1779 (7)	0.0727 (6)	0.4415 (5)	0.0566 (16)
H8A	0.1162	0.0370	0.4304	0.068*
C9	0.3051 (7)	0.0557 (5)	0.3849 (4)	0.0536 (15)
H9A	0.3286	0.0097	0.3338	0.064*
C10	0.4030 (6)	0.1046 (5)	0.4001 (4)	0.0470 (14)
C11	0.1848 (6)	0.2737 (5)	0.6133 (4)	0.0405 (13)
C12	0.4232 (6)	0.2937 (5)	0.5833 (4)	0.0460 (13)
C13	0.2805 (6)	0.3486 (5)	0.7979 (4)	0.0514 (15)
H13A	0.2603	0.2703	0.8244	0.062*
H13B	0.3784	0.3363	0.7882	0.062*
C14	0.2116 (7)	0.4275 (6)	0.8720 (5)	0.0590 (16)
C15	0.1620 (9)	0.4915 (8)	0.9295 (6)	0.091 (3)
H15	0.1218	0.5435	0.9762	0.109*
C16	0.2598 (6)	0.5219 (5)	0.6495 (5)	0.0499 (14)
H16A	0.2196	0.5768	0.6977	0.060*
H16B	0.3573	0.5144	0.6322	0.060*
C17	0.2019 (6)	0.5705 (5)	0.5570 (5)	0.0508 (15)
C18	0.1566 (8)	0.6073 (6)	0.4818 (6)	0.073 (2)
H18	0.1203	0.6370	0.4213	0.088*

	U11	U22	U33	U12	U13	U23
Br2	0.1274 (11)	0.0833 (8)	0.1227 (10)	−0.0587 (8)	−0.0590 (8)	−0.0111 (7)
C19	0.090 (5)	0.042 (4)	0.072 (4)	−0.024 (3)	−0.040 (4)	−0.004 (3)
C27	0.062 (4)	0.057 (4)	0.073 (4)	−0.021 (3)	−0.025 (4)	0.000 (4)
Br2'	0.0594 (18)	0.0600 (18)	0.103 (2)	−0.0243 (13)	−0.0217 (15)	−0.0145 (15)
C19'	0.090 (5)	0.042 (4)	0.072 (4)	−0.024 (3)	−0.040 (4)	−0.004 (3)
C27'	0.062 (4)	0.057 (4)	0.073 (4)	−0.021 (3)	−0.025 (4)	0.000 (4)
O3	0.045 (2)	0.071 (3)	0.062 (3)	−0.021 (2)	0.011 (2)	−0.034 (2)
O4	0.056 (3)	0.072 (3)	0.053 (2)	−0.019 (2)	0.008 (2)	−0.038 (2)
N3	0.040 (3)	0.043 (3)	0.037 (2)	−0.012 (2)	−0.0010 (19)	−0.0156 (19)
N4	0.046 (3)	0.046 (3)	0.041 (2)	−0.019 (2)	−0.008 (2)	−0.010 (2)
C20	0.075 (5)	0.059 (4)	0.072 (4)	−0.016 (4)	−0.016 (4)	−0.026 (4)
C21	0.060 (4)	0.056 (4)	0.051 (3)	−0.009 (3)	−0.010 (3)	−0.018 (3)
C22	0.054 (4)	0.035 (3)	0.042 (3)	−0.010 (3)	−0.007 (3)	−0.010 (2)
C23	0.041 (3)	0.036 (3)	0.042 (3)	−0.012 (2)	−0.015 (2)	0.002 (2)
C24	0.040 (3)	0.037 (3)	0.035 (3)	−0.007 (2)	−0.007 (2)	−0.003 (2)
C25	0.044 (4)	0.055 (4)	0.048 (3)	−0.011 (3)	−0.009 (3)	−0.002 (3)
C26	0.033 (3)	0.071 (5)	0.071 (4)	−0.019 (3)	−0.009 (3)	0.011 (4)
C28	0.058 (4)	0.042 (3)	0.055 (3)	−0.016 (3)	−0.024 (3)	0.003 (3)
C29	0.040 (3)	0.043 (3)	0.039 (3)	−0.008 (2)	−0.005 (3)	−0.009 (2)
C30	0.045 (3)	0.044 (3)	0.035 (3)	−0.007 (2)	−0.008 (2)	−0.010 (2)
C31	0.055 (4)	0.059 (4)	0.050 (3)	−0.022 (3)	−0.011 (3)	−0.014 (3)
C32	0.055 (4)	0.057 (4)	0.048 (3)	−0.013 (3)	−0.012 (3)	−0.019 (3)
C33	0.080 (5)	0.064 (4)	0.051 (4)	−0.017 (4)	−0.011 (3)	−0.016 (3)
C34	0.058 (4)	0.048 (4)	0.054 (3)	−0.018 (3)	−0.002 (3)	−0.014 (3)
C35	0.056 (4)	0.049 (4)	0.050 (3)	−0.017 (3)	−0.012 (3)	−0.006 (3)
C36	0.072 (5)	0.067 (5)	0.081 (5)	−0.014 (4)	−0.024 (4)	−0.011 (4)
Br1	0.0852 (5)	0.0556 (4)	0.0410 (3)	−0.0003 (3)	−0.0023 (3)	−0.0167 (3)
O1	0.047 (3)	0.075 (3)	0.073 (3)	−0.019 (2)	−0.005 (2)	−0.031 (2)
O2	0.044 (2)	0.075 (3)	0.046 (2)	−0.018 (2)	−0.0006 (19)	−0.024 (2)
N1	0.035 (2)	0.038 (2)	0.038 (2)	−0.0026 (19)	−0.0018 (19)	−0.0125 (19)
N2	0.050 (3)	0.036 (2)	0.038 (2)	−0.007 (2)	−0.011 (2)	−0.0098 (19)
C1	0.063 (4)	0.041 (3)	0.034 (3)	−0.001 (3)	−0.004 (3)	−0.005 (2)
C2	0.041 (3)	0.060 (4)	0.042 (3)	−0.007 (3)	0.006 (3)	−0.011 (3)
C3	0.053 (4)	0.045 (3)	0.054 (3)	−0.011 (3)	−0.003 (3)	−0.008 (3)
C4	0.043 (3)	0.037 (3)	0.039 (3)	−0.001 (2)	−0.004 (2)	−0.004 (2)
C5	0.056 (4)	0.030 (3)	0.030 (2)	−0.004 (2)	−0.011 (2)	0.001 (2)
C6	0.050 (3)	0.039 (3)	0.032 (3)	−0.008 (2)	−0.008 (2)	−0.005 (2)
C7	0.055 (4)	0.051 (4)	0.046 (3)	−0.012 (3)	−0.011 (3)	−0.015 (3)
C8	0.066 (4)	0.057 (4)	0.056 (4)	−0.020 (3)	−0.018 (3)	−0.015 (3)
C9	0.071 (5)	0.046 (4)	0.044 (3)	−0.012 (3)	−0.011 (3)	−0.013 (3)
C10	0.058 (4)	0.037 (3)	0.033 (3)	−0.002 (3)	−0.007 (3)	0.001 (2)
C11	0.050 (4)	0.040 (3)	0.029 (2)	−0.009 (3)	−0.009 (3)	−0.003 (2)
C12	0.046 (4)	0.041 (3)	0.048 (3)	−0.008 (3)	−0.012 (3)	−0.006 (3)
C13	0.061 (4)	0.052 (4)	0.040 (3)	−0.010 (3)	−0.015 (3)	−0.006 (3)
C14	0.069 (4)	0.061 (4)	0.048 (3)	−0.010 (3)	−0.012 (3)	−0.020 (3)
C15	0.131 (7)	0.081 (6)	0.060 (4)	−0.008 (5)	−0.021 (5)	−0.032 (4)
C16	0.050 (3)	0.040 (3)	0.059 (3)	−0.003 (3)	−0.018 (3)	−0.010 (3)
C17	0.061 (4)	0.038 (3)	0.047 (3)	−0.002 (3)	−0.010 (3)	−0.009 (3)
C18	0.089 (5)	0.054 (4)	0.066 (4)	0.002 (4)	−0.020 (4)	−0.012 (3)

Br2—C19	1.927 (6)	Br1—C1	1.888 (6)
C19—C20	1.326 (9)	O1—C12	1.197 (7)
C19—C28	1.421 (9)	O2—C11	1.202 (6)
C27—C26	1.386 (9)	N1—C12	1.405 (7)
C27—C28	1.394 (9)	N1—C11	1.409 (7)
C27—H27	0.9300	N1—N2	1.415 (6)
O3—C29	1.196 (6)	N2—C16	1.462 (7)
O4—C30	1.205 (6)	N2—C13	1.465 (7)
N3—C29	1.397 (7)	C1—C2	1.361 (9)
N3—N4	1.399 (6)	C1—C10	1.411 (8)
N3—C30	1.416 (7)	C2—C3	1.410 (8)
N4—C34	1.452 (7)	C2—H2A	0.9300
N4—C31	1.486 (7)	C3—C4	1.361 (8)
C20—C21	1.383 (9)	C3—H3A	0.9300
C20—H20A	0.9300	C4—C5	1.409 (8)
C21—C22	1.369 (8)	C4—C12	1.473 (8)
C21—H21A	0.9300	C5—C6	1.392 (8)
C22—C23	1.417 (8)	C5—C10	1.437 (8)
C22—C29	1.474 (8)	C6—C7	1.372 (8)
C23—C24	1.411 (7)	C6—C11	1.491 (7)
C23—C28	1.421 (8)	C7—C8	1.405 (8)
C24—C25	1.357 (8)	C7—H7A	0.9300
C24—C30	1.473 (8)	C8—C9	1.346 (9)
C25—C26	1.414 (9)	C8—H8A	0.9300
C25—H25A	0.9300	C9—C10	1.396 (9)
C26—H26A	0.9300	C9—H9A	0.9300
C31—C32	1.454 (9)	C13—C14	1.453 (8)
C31—H31A	0.9700	C13—H13A	0.9700
C31—H31B	0.9700	C13—H13B	0.9700
C32—C33	1.168 (9)	C14—C15	1.147 (9)
C33—H33	0.9300	C15—H15	0.9300
C34—C35	1.449 (9)	C16—C17	1.436 (8)
C34—H34A	0.9700	C16—H16A	0.9700
C34—H34B	0.9700	C16—H16B	0.9700
C35—C36	1.161 (9)	C17—C18	1.157 (9)
C36—H36	0.9300	C18—H18	0.9300
C20—C19—C28	124.4 (6)	C12—N1—C11	125.4 (4)
C20—C19—Br2	120.0 (5)	C12—N1—N2	120.1 (4)
C28—C19—Br2	115.6 (5)	C11—N1—N2	114.5 (4)
C26—C27—C28	118.8 (6)	N1—N2—C16	111.9 (4)
C26—C27—H27	120.6	N1—N2—C13	111.2 (4)
C28—C27—H27	120.6	C16—N2—C13	115.4 (4)
C29—N3—N4	120.3 (4)	C2—C1—C10	122.8 (5)
C29—N3—C30	125.2 (5)	C2—C1—Br1	118.2 (4)
N4—N3—C30	114.5 (4)	C10—C1—Br1	119.0 (5)
N3—N4—C34	113.2 (4)	C1—C2—C3	120.3 (5)
N3—N4—C31	113.7 (4)	C1—C2—H2A	119.9
C34—N4—C31	111.7 (4)	C3—C2—H2A	119.9
C19—C20—C21	119.9 (6)	C4—C3—C2	119.5 (6)
C19—C20—H20A	120.0	C4—C3—H3A	120.2
C21—C20—H20A	120.0	C2—C3—H3A	120.2
C22—C21—C20	120.1 (6)	C3—C4—C5	121.1 (5)
C22—C21—H21A	120.0	C3—C4—C12	118.2 (6)
C20—C21—H21A	120.0	C5—C4—C12	120.7 (5)
C21—C22—C23	120.6 (6)	C6—C5—C4	121.2 (5)
C21—C22—C29	118.5 (5)	C6—C5—C10	118.6 (5)
C23—C22—C29	120.8 (5)	C4—C5—C10	120.2 (5)
C24—C23—C22	120.1 (5)	C7—C6—C5	121.5 (5)
C24—C23—C28	120.2 (5)	C7—C6—C11	118.2 (5)
C22—C23—C28	119.7 (5)	C5—C6—C11	120.2 (5)
C25—C24—C23	119.9 (5)	C6—C7—C8	119.5 (6)
C25—C24—C30	119.2 (5)	C6—C7—H7A	120.2
C23—C24—C30	120.9 (5)	C8—C7—H7A	120.2
C24—C25—C26	119.7 (6)	C9—C8—C7	120.0 (6)
C24—C25—H25A	120.1	C9—C8—H8A	120.0
C26—C25—H25A	120.1	C7—C8—H8A	120.0
C27—C26—C25	121.8 (6)	C8—C9—C10	122.5 (6)
C27—C26—H26A	119.1	C8—C9—H9A	118.8
C25—C26—H26A	119.1	C10—C9—H9A	118.8
C27—C28—C19	125.2 (6)	C9—C10—C1	126.1 (6)
C27—C28—C23	119.5 (6)	C9—C10—C5	117.8 (5)
C19—C28—C23	115.3 (6)	C1—C10—C5	116.1 (6)
O3—C29—N3	120.2 (5)	O2—C11—N1	121.6 (5)
O3—C29—C22	123.2 (5)	O2—C11—C6	122.4 (5)
N3—C29—C22	116.6 (5)	N1—C11—C6	116.0 (5)
O4—C30—N3	120.6 (5)	O1—C12—N1	119.9 (5)
O4—C30—C24	123.1 (5)	O1—C12—C4	124.3 (5)
N3—C30—C24	116.3 (4)	N1—C12—C4	115.8 (5)
C32—C31—N4	111.0 (5)	C14—C13—N2	109.8 (5)
C32—C31—H31A	109.4	C14—C13—H13A	109.7
N4—C31—H31A	109.4	N2—C13—H13A	109.7
C32—C31—H31B	109.4	C14—C13—H13B	109.7
N4—C31—H31B	109.4	N2—C13—H13B	109.7
H31A—C31—H31B	108.0	H13A—C13—H13B	108.2
C33—C32—C31	179.0 (7)	C15—C14—C13	177.1 (9)
C32—C33—H33	180.0	C14—C15—H15	180.0
C35—C34—N4	112.8 (5)	C17—C16—N2	110.5 (5)
C35—C34—H34A	109.0	C17—C16—H16A	109.5
N4—C34—H34A	109.0	N2—C16—H16A	109.5
C35—C34—H34B	109.0	C17—C16—H16B	109.5
N4—C34—H34B	109.0	N2—C16—H16B	109.5
H34A—C34—H34B	107.8	H16A—C16—H16B	108.1
C36—C35—C34	178.3 (7)	C18—C17—C16	178.6 (7)
C35—C36—H36	180.0	C17—C18—H18	180.0
C29—N3—N4—C34	62.9 (6)	C12—N1—N2—C16	58.3 (6)
C30—N3—N4—C34	−116.9 (5)	C11—N1—N2—C16	−121.7 (5)
C29—N3—N4—C31	−66.0 (6)	C12—N1—N2—C13	−72.5 (6)
C30—N3—N4—C31	114.2 (5)	C11—N1—N2—C13	107.6 (5)
C28—C19—C20—C21	−1.4 (10)	C10—C1—C2—C3	0.8 (9)
Br2—C19—C20—C21	178.6 (5)	Br1—C1—C2—C3	−179.7 (4)
C19—C20—C21—C22	1.2 (10)	C1—C2—C3—C4	−1.4 (9)
C20—C21—C22—C23	−1.3 (9)	C2—C3—C4—C5	0.3 (8)
C20—C21—C22—C29	−178.4 (5)	C2—C3—C4—C12	179.4 (5)
C21—C22—C23—C24	179.9 (5)	C3—C4—C5—C6	−179.2 (5)
C29—C22—C23—C24	−3.1 (8)	C12—C4—C5—C6	1.8 (7)
C21—C22—C23—C28	1.5 (8)	C3—C4—C5—C10	1.3 (8)
C29—C22—C23—C28	178.5 (5)	C12—C4—C5—C10	−177.8 (5)
C22—C23—C24—C25	−179.8 (5)	C4—C5—C6—C7	−177.7 (5)
C28—C23—C24—C25	−1.4 (7)	C10—C5—C6—C7	1.8 (7)
C22—C23—C24—C30	−0.1 (7)	C4—C5—C6—C11	3.8 (7)
C28—C23—C24—C30	178.3 (5)	C10—C5—C6—C11	−176.7 (4)
C23—C24—C25—C26	1.1 (8)	C5—C6—C7—C8	−0.5 (8)
C30—C24—C25—C26	−178.5 (5)	C11—C6—C7—C8	178.1 (5)
C28—C27—C26—C25	0.4 (9)	C6—C7—C8—C9	−1.3 (9)
C24—C25—C26—C27	−0.6 (9)	C7—C8—C9—C10	1.7 (9)
C26—C27—C28—C19	−179.5 (6)	C8—C9—C10—C1	179.6 (6)
C26—C27—C28—C23	−0.6 (9)	C8—C9—C10—C5	−0.3 (8)
C20—C19—C28—C27	−179.6 (6)	C2—C1—C10—C9	−179.1 (6)
Br2—C19—C28—C27	0.5 (8)	Br1—C1—C10—C9	1.5 (8)
C20—C19—C28—C23	1.5 (9)	C2—C1—C10—C5	0.8 (8)
Br2—C19—C28—C23	−178.4 (4)	Br1—C1—C10—C5	−178.7 (4)
C24—C23—C28—C27	1.1 (8)	C6—C5—C10—C9	−1.5 (7)
C22—C23—C28—C27	179.5 (5)	C4—C5—C10—C9	178.1 (5)
C24—C23—C28—C19	−179.9 (5)	C6—C5—C10—C1	178.7 (5)
C22—C23—C28—C19	−1.5 (7)	C4—C5—C10—C1	−1.8 (7)
N4—N3—C29—O3	1.8 (8)	C12—N1—C11—O2	174.4 (5)
C30—N3—C29—O3	−178.4 (5)	N2—N1—C11—O2	−5.6 (7)
N4—N3—C29—C22	−177.6 (4)	C12—N1—C11—C6	−4.6 (7)
C30—N3—C29—C22	2.2 (7)	N2—N1—C11—C6	175.3 (4)
C21—C22—C29—O3	−0.2 (8)	C7—C6—C11—O2	−0.2 (8)
C23—C22—C29—O3	−177.3 (5)	C5—C6—C11—O2	178.4 (5)
C21—C22—C29—N3	179.2 (5)	C7—C6—C11—N1	178.9 (5)
C23—C22—C29—N3	2.1 (7)	C5—C6—C11—N1	−2.5 (7)
C29—N3—C30—O4	175.9 (5)	C11—N1—C12—O1	−170.7 (5)
N4—N3—C30—O4	−4.4 (7)	N2—N1—C12—O1	9.4 (8)
C29—N3—C30—C24	−5.1 (7)	C11—N1—C12—C4	9.8 (7)
N4—N3—C30—C24	174.6 (4)	N2—N1—C12—C4	−170.1 (4)
C25—C24—C30—O4	2.6 (8)	C3—C4—C12—O1	−6.8 (9)
C23—C24—C30—O4	−177.0 (5)	C5—C4—C12—O1	172.3 (5)
C25—C24—C30—N3	−176.3 (5)	C3—C4—C12—N1	172.8 (5)
C23—C24—C30—N3	4.0 (7)	C5—C4—C12—N1	−8.2 (7)
N3—N4—C31—C32	−51.7 (6)	N1—N2—C13—C14	−171.5 (5)
C34—N4—C31—C32	178.6 (5)	C16—N2—C13—C14	59.6 (7)
N4—C31—C32—C33	176 (100)	N2—C13—C14—C15	−99 (15)
N3—N4—C34—C35	51.8 (6)	N1—N2—C16—C17	55.8 (6)
C31—N4—C34—C35	−178.3 (5)	C13—N2—C16—C17	−175.6 (5)
N4—C34—C35—C36	−157 (25)	N2—C16—C17—C18	−52 (32)