Crystal structures of 2,3,8,9,14,15-hexa­methyl-5,6,11,12,17,18-hexa­aza­tri­naphthyl­ene and 2,3,8,9,14,15-hexa­phenyl-5,6,11,12,17,18-hexa­za­tri­naphthyl­ene di­chloro­methane disolvate

2,3,8,9,14,15-Hexamethyl- and 2,3,8,9,14,15-hexa­phenyl-5,6,11,12,17,18-hexa­zatri­naphthyl­ene (HATNMe₆ and HATNPh₆) are derivatives of hexa­aza­tri­naphthyl­ene (HATN). In the crystal structures of the two compounds, pronounced π–π stacking dominates the packing.

Key indicators

Structure: 1

• Single-crystal X-ray study
• T = 153 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.032
• wR factor = 0.080
• Data-to-parameter ratio = 14.2

Structure: 2

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.039
• wR factor = 0.107
• Data-to-parameter ratio = 22.2

checkCIF/PLATON results

No syntax errors found



Datablock: 1


Alert level C
GOODF01_ALERT_2_C  The least squares goodness of fit parameter lies
            outside the range 0.80 <> 2.00
            Goodness of fit given =      0.746
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.096 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report

Alert level G
PLAT333_ALERT_2_G Large Aver C6-Ring C-C Dist. C1       -C1_a            1.45 Ang.
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         12 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          2 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT955_ALERT_1_G Reported (CIF) and Actual (FCF) Lmax Differ by .          1 Units
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          6 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

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




Datablock: 2


Alert level G
PLAT333_ALERT_2_G Large Aver C6-Ring C-C Dist. C1       -C6              1.45 Ang.
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         20 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

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

---

Computing details

Data collection: IPDS (Stoe, 1999) for (1); APEX2 (Bruker, 2013) for (2). Cell refinement: IPDS (Stoe, 1999) for (1); SAINT (Bruker, 2013) for (2). Data reduction: X-RED (Stoe, 2002) for (1); SAINT (Bruker, 2013) for (2). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (1); SHELXS2013/1 (Sheldrick, 2015a) for (2). For both structures, program(s) used to refine structure: SHELXL2017/1 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

2,3,8,9,14,15-Hexamethyl-5,6,11,12,17,18-hexaazatrinaphthylene (1)

Crystal data

C30H24N6	Dx = 1.320 Mg m^−3
Mr = 468.55	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbcn	Cell parameters from 5493 reflections
a = 11.6178 (8) Å	θ = 2.3–26.2°
b = 15.7762 (8) Å	µ = 0.08 mm^−1
c = 12.8621 (7) Å	T = 153 K
V = 2357.4 (2) Å^3	Prism, yellow
Z = 4	0.50 × 0.38 × 0.25 mm
F(000) = 984

Data collection

Stoe IPDS diffractometer	Rint = 0.057
Radiation source: sealed tube	θmax = 26.2°, θmin = 2.6°
φ scans	h = −14→14
23121 measured reflections	k = −19→19
2361 independent reflections	l = −15→16
1286 reflections with I > 2σ(I)

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H-atom parameters constrained
wR(F^2) = 0.080	w = 1/[σ^2(Fo^2) + (0.050P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.75	(Δ/σ)max < 0.001
2361 reflections	Δρmax = 0.16 e Å^−3
166 parameters	Δρmin = −0.14 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
N1	0.56074 (10)	0.64519 (8)	0.34566 (8)	0.0255 (3)
N2	0.62730 (10)	0.49478 (7)	0.43437 (8)	0.0265 (3)
N3	0.56076 (10)	0.34059 (8)	0.33894 (7)	0.0252 (3)
C1	0.53175 (13)	0.57382 (8)	0.29813 (10)	0.0226 (3)
C2	0.56581 (11)	0.49314 (9)	0.34649 (9)	0.0225 (3)
C3	0.53343 (12)	0.41546 (9)	0.29893 (9)	0.0225 (3)
C4	0.52959 (12)	0.71863 (9)	0.29846 (10)	0.0247 (3)
C5	0.55513 (12)	0.79701 (10)	0.34611 (10)	0.0283 (3)
H5	0.592691	0.797343	0.411715	0.034*
C6	0.52734 (13)	0.87212 (9)	0.30047 (11)	0.0314 (4)
C7	0.55470 (17)	0.95456 (11)	0.35433 (13)	0.0502 (5)
H7A	0.579276	0.943076	0.425845	0.075*
H7B	0.485952	0.990540	0.355234	0.075*
H7C	0.616673	0.983645	0.316924	0.075*
C8	0.65625 (12)	0.41882 (9)	0.47584 (10)	0.0246 (3)
C9	0.72310 (13)	0.41486 (9)	0.56818 (10)	0.0288 (4)
H9	0.745094	0.466061	0.601600	0.035*
C10	0.75658 (12)	0.33909 (9)	0.61015 (10)	0.0281 (3)
C11	0.72339 (12)	0.26111 (9)	0.56134 (10)	0.0266 (3)
C12	0.65713 (13)	0.26394 (9)	0.47327 (10)	0.0269 (3)
H12	0.633497	0.212331	0.441761	0.032*
C13	0.62308 (11)	0.34154 (9)	0.42814 (9)	0.0238 (3)
C14	0.82859 (14)	0.33631 (11)	0.70797 (11)	0.0398 (4)
H14A	0.846997	0.394234	0.729895	0.060*
H14B	0.900037	0.305244	0.694236	0.060*
H14C	0.785419	0.307648	0.763184	0.060*
C15	0.76172 (14)	0.17752 (9)	0.60460 (11)	0.0367 (4)
H15A	0.729041	0.131482	0.562831	0.055*
H15B	0.735262	0.172194	0.676654	0.055*
H15C	0.845931	0.174242	0.602613	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0268 (6)	0.0259 (7)	0.0237 (5)	−0.0006 (6)	−0.0010 (5)	0.0007 (5)
N2	0.0279 (6)	0.0280 (7)	0.0235 (6)	−0.0014 (6)	−0.0026 (5)	0.0015 (5)
N3	0.0279 (6)	0.0277 (7)	0.0201 (5)	0.0003 (6)	−0.0001 (5)	0.0010 (5)
C1	0.0211 (7)	0.0255 (9)	0.0213 (6)	−0.0007 (6)	0.0018 (6)	−0.0005 (5)
C2	0.0209 (7)	0.0265 (8)	0.0201 (6)	0.0010 (7)	0.0028 (6)	0.0001 (6)
C3	0.0224 (7)	0.0259 (8)	0.0191 (6)	0.0008 (6)	0.0034 (6)	0.0006 (5)
C4	0.0225 (7)	0.0271 (9)	0.0244 (7)	−0.0003 (7)	0.0010 (6)	0.0011 (6)
C5	0.0274 (8)	0.0313 (9)	0.0262 (7)	−0.0004 (7)	−0.0058 (6)	−0.0017 (6)
C6	0.0311 (8)	0.0272 (9)	0.0360 (8)	−0.0017 (7)	−0.0061 (6)	−0.0015 (6)
C7	0.0685 (13)	0.0294 (10)	0.0526 (9)	0.0004 (9)	−0.0288 (9)	−0.0037 (8)
C8	0.0236 (8)	0.0277 (9)	0.0225 (7)	0.0009 (6)	0.0014 (6)	0.0025 (6)
C9	0.0311 (9)	0.0301 (9)	0.0254 (7)	−0.0031 (7)	−0.0033 (6)	−0.0006 (6)
C10	0.0267 (8)	0.0323 (9)	0.0253 (6)	−0.0006 (7)	−0.0011 (6)	0.0061 (6)
C11	0.0261 (8)	0.0287 (9)	0.0252 (7)	0.0031 (6)	0.0044 (6)	0.0049 (6)
C12	0.0306 (8)	0.0257 (8)	0.0246 (7)	0.0003 (6)	0.0025 (6)	−0.0011 (5)
C13	0.0238 (7)	0.0277 (8)	0.0198 (6)	0.0012 (7)	0.0027 (5)	0.0010 (6)
C14	0.0426 (9)	0.0399 (10)	0.0370 (8)	−0.0030 (8)	−0.0141 (7)	0.0061 (7)
C15	0.0385 (10)	0.0365 (10)	0.0350 (8)	0.0033 (8)	−0.0042 (7)	0.0063 (6)

Geometric parameters (Å, º)

N1—C1	1.3248 (17)	C7—H7C	0.9800
N1—C4	1.3571 (18)	C8—C13	1.4181 (19)
N2—C2	1.3374 (15)	C8—C9	1.4205 (19)
N2—C8	1.3541 (18)	C9—C10	1.368 (2)
N3—C3	1.3270 (17)	C9—H9	0.9500
N3—C13	1.3568 (16)	C10—C11	1.434 (2)
C1—C1^i	1.441 (3)	C10—C14	1.5115 (19)
C1—C2	1.4709 (19)	C11—C12	1.3703 (19)
C2—C3	1.4203 (19)	C11—C15	1.4990 (19)
C3—C3^i	1.479 (3)	C12—C13	1.4115 (19)
C4—C5	1.412 (2)	C12—H12	0.9500
C4—C4^i	1.424 (3)	C14—H14A	0.9800
C5—C6	1.361 (2)	C14—H14B	0.9800
C5—H5	0.9500	C14—H14C	0.9800
C6—C6^i	1.445 (3)	C15—H15A	0.9800
C6—C7	1.507 (2)	C15—H15B	0.9800
C7—H7A	0.9800	C15—H15C	0.9800
C7—H7B	0.9800
C1—N1—C4	116.83 (11)	C13—C8—C9	118.20 (12)
C2—N2—C8	116.65 (12)	C10—C9—C8	121.58 (14)
C3—N3—C13	116.47 (12)	C10—C9—H9	119.2
N1—C1—C1^i	121.77 (8)	C8—C9—H9	119.2
N1—C1—C2	118.16 (12)	C9—C10—C11	120.03 (12)
C1^i—C1—C2	120.07 (7)	C9—C10—C14	120.74 (14)
N2—C2—C3	121.48 (13)	C11—C10—C14	119.24 (13)
N2—C2—C1	118.97 (13)	C12—C11—C10	119.02 (13)
C3—C2—C1	119.55 (11)	C12—C11—C15	120.17 (13)
N3—C3—C2	122.52 (12)	C10—C11—C15	120.81 (12)
N3—C3—C3^i	117.11 (7)	C11—C12—C13	121.71 (13)
C2—C3—C3^i	120.37 (8)	C11—C12—H12	119.1
N1—C4—C5	119.83 (12)	C13—C12—H12	119.1
N1—C4—C4^i	121.37 (7)	N3—C13—C12	119.18 (13)
C5—C4—C4^i	118.80 (8)	N3—C13—C8	121.36 (12)
C6—C5—C4	121.70 (12)	C12—C13—C8	119.45 (11)
C6—C5—H5	119.1	C10—C14—H14A	109.5
C4—C5—H5	119.1	C10—C14—H14B	109.5
C5—C6—C6^i	119.44 (8)	H14A—C14—H14B	109.5
C5—C6—C7	120.19 (13)	C10—C14—H14C	109.5
C6^i—C6—C7	120.36 (9)	H14A—C14—H14C	109.5
C6—C7—H7A	109.5	H14B—C14—H14C	109.5
C6—C7—H7B	109.5	C11—C15—H15A	109.5
H7A—C7—H7B	109.5	C11—C15—H15B	109.5
C6—C7—H7C	109.5	H15A—C15—H15B	109.5
H7A—C7—H7C	109.5	C11—C15—H15C	109.5
H7B—C7—H7C	109.5	H15A—C15—H15C	109.5
N2—C8—C13	121.52 (12)	H15B—C15—H15C	109.5
N2—C8—C9	120.27 (13)
C4—N1—C1—C1^i	−1.1 (2)	C2—N2—C8—C13	0.12 (18)
C4—N1—C1—C2	179.08 (13)	C2—N2—C8—C9	178.97 (12)
C8—N2—C2—C3	−0.44 (17)	N2—C8—C9—C10	−178.02 (13)
C8—N2—C2—C1	179.87 (12)	C13—C8—C9—C10	0.9 (2)
N1—C1—C2—N2	−1.96 (18)	C8—C9—C10—C11	−0.5 (2)
C1^i—C1—C2—N2	178.26 (15)	C8—C9—C10—C14	179.46 (14)
N1—C1—C2—C3	178.35 (13)	C9—C10—C11—C12	−0.7 (2)
C1^i—C1—C2—C3	−1.4 (2)	C14—C10—C11—C12	179.35 (13)
C13—N3—C3—C2	−0.70 (18)	C9—C10—C11—C15	178.43 (14)
C13—N3—C3—C3^i	179.36 (15)	C14—C10—C11—C15	−1.56 (19)
N2—C2—C3—N3	0.77 (19)	C10—C11—C12—C13	1.5 (2)
C1—C2—C3—N3	−179.54 (13)	C15—C11—C12—C13	−177.59 (13)
N2—C2—C3—C3^i	−179.28 (15)	C3—N3—C13—C12	−178.55 (12)
C1—C2—C3—C3^i	0.4 (2)	C3—N3—C13—C8	0.36 (17)
C1—N1—C4—C5	178.39 (14)	C11—C12—C13—N3	177.78 (13)
C1—N1—C4—C4^i	−1.1 (2)	C11—C12—C13—C8	−1.2 (2)
N1—C4—C5—C6	178.74 (15)	N2—C8—C13—N3	−0.1 (2)
C4^i—C4—C5—C6	−1.7 (2)	C9—C8—C13—N3	−178.96 (13)
C4—C5—C6—C6^i	−1.5 (3)	N2—C8—C13—C12	178.83 (14)
C4—C5—C6—C7	179.25 (15)	C9—C8—C13—C12	−0.04 (18)

Symmetry code: (i) −x+1, y, −z+1/2.

2,3,8,9,14,15-Hexaphenyl-5,6,11,12,17,18-hexazatrinaphthylene dichloromethane disolvate (2)

Crystal data

C60H36N6·2CH2Cl2	Z = 2
Mr = 1010.80	F(000) = 1044
Triclinic, P1	Dx = 1.364 Mg m^−3
a = 9.2629 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 16.3829 (6) Å	Cell parameters from 9893 reflections
c = 18.4366 (6) Å	θ = 2.3–30.0°
α = 64.2659 (13)°	µ = 0.29 mm^−1
β = 78.2616 (15)°	T = 100 K
γ = 88.3530 (17)°	Block, yellow
V = 2461.98 (16) Å^3	0.30 × 0.12 × 0.10 mm

Data collection

Bruker APEX-II CCD diffractometer	11804 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.043
φ and ω scans	θmax = 30.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −13→13
Tmin = 0.970, Tmax = 1.000	k = −23→23
87137 measured reflections	l = −25→25
14377 independent reflections

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)] = 0.039	Hydrogen site location: difference Fourier map
wR(F^2) = 0.107	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.050P)^2 + 1.2P] where P = (Fo^2 + 2Fc^2)/3
14377 reflections	(Δ/σ)max = 0.001
649 parameters	Δρmax = 0.84 e Å^−3
0 restraints	Δρmin = −0.84 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
N1	0.11926 (11)	0.44967 (7)	0.60814 (6)	0.01193 (18)
N2	0.18060 (11)	0.60400 (7)	0.45277 (6)	0.01252 (19)
N3	0.41523 (11)	0.61360 (7)	0.33603 (6)	0.01264 (19)
N4	0.59471 (11)	0.46401 (7)	0.36209 (6)	0.01232 (19)
N5	0.53889 (11)	0.31547 (7)	0.51241 (6)	0.01196 (18)
N6	0.27642 (11)	0.29872 (7)	0.62955 (6)	0.01280 (19)
C1	0.22651 (12)	0.45307 (8)	0.54672 (7)	0.0107 (2)
C2	0.25958 (12)	0.53194 (8)	0.46923 (7)	0.0111 (2)
C3	0.38735 (12)	0.53672 (8)	0.40497 (7)	0.0110 (2)
C4	0.47903 (12)	0.46219 (8)	0.41903 (7)	0.0109 (2)
C5	0.44562 (13)	0.38091 (8)	0.49903 (7)	0.0110 (2)
C6	0.31672 (12)	0.37406 (8)	0.55998 (7)	0.0113 (2)
C7	0.04205 (13)	0.52505 (8)	0.59315 (7)	0.0116 (2)
C8	−0.06780 (13)	0.53019 (8)	0.65653 (7)	0.0132 (2)
H8	−0.088884	0.479364	0.709104	0.016*
C9	−0.14549 (13)	0.60696 (8)	0.64431 (7)	0.0128 (2)
C10	−0.12054 (13)	0.68304 (8)	0.56292 (7)	0.0128 (2)
C11	−0.01485 (13)	0.67705 (8)	0.50117 (7)	0.0142 (2)
H11	0.000554	0.725739	0.447369	0.017*
C12	0.07124 (13)	0.60140 (8)	0.51484 (7)	0.0122 (2)
C13	−0.24727 (13)	0.60780 (8)	0.71806 (7)	0.0140 (2)
C14	−0.34319 (14)	0.53190 (9)	0.77210 (8)	0.0175 (2)
H14	−0.344709	0.480483	0.761037	0.021*
C15	−0.43664 (15)	0.53104 (10)	0.84210 (8)	0.0229 (3)
H15	−0.502156	0.479426	0.878182	0.028*
C16	−0.43391 (16)	0.60558 (11)	0.85904 (9)	0.0244 (3)
H16	−0.497906	0.605196	0.906536	0.029*
C17	−0.33734 (16)	0.68085 (10)	0.80636 (9)	0.0233 (3)
H17	−0.334699	0.731629	0.818261	0.028*
C18	−0.24461 (15)	0.68200 (9)	0.73633 (8)	0.0181 (2)
H18	−0.178930	0.733655	0.700611	0.022*
C19	−0.20291 (13)	0.76731 (8)	0.53886 (7)	0.0139 (2)
C20	−0.35316 (14)	0.76736 (9)	0.57128 (8)	0.0161 (2)
H20	−0.404730	0.713178	0.614174	0.019*
C21	−0.42778 (14)	0.84646 (9)	0.54103 (8)	0.0185 (2)
H21	−0.529303	0.845922	0.564415	0.022*
C22	−0.35570 (15)	0.92581 (9)	0.47732 (8)	0.0197 (3)
H22	−0.408316	0.978749	0.455846	0.024*
C23	−0.20617 (15)	0.92744 (9)	0.44508 (8)	0.0193 (2)
H23	−0.155738	0.981790	0.401845	0.023*
C24	−0.13024 (14)	0.84933 (9)	0.47618 (8)	0.0172 (2)
H24	−0.027381	0.851395	0.454697	0.021*
C25	0.53512 (13)	0.61711 (8)	0.27859 (7)	0.0127 (2)
C26	0.57330 (13)	0.69798 (8)	0.20488 (7)	0.0144 (2)
H26	0.516697	0.749110	0.198040	0.017*
C27	0.69015 (13)	0.70462 (8)	0.14283 (7)	0.0134 (2)
C28	0.77379 (13)	0.62586 (8)	0.15212 (7)	0.0136 (2)
C29	0.74119 (13)	0.54812 (8)	0.22552 (7)	0.0145 (2)
H29	0.799147	0.497494	0.232495	0.017*
C30	0.62378 (13)	0.54171 (8)	0.29071 (7)	0.0124 (2)
C31	0.72725 (13)	0.79506 (8)	0.07089 (7)	0.0135 (2)
C32	0.61387 (14)	0.84510 (9)	0.03578 (8)	0.0161 (2)
H32	0.515374	0.818781	0.054791	0.019*
C33	0.64453 (15)	0.93319 (9)	−0.02681 (8)	0.0183 (2)
H33	0.566824	0.966807	−0.050029	0.022*
C34	0.78795 (15)	0.97199 (9)	−0.05534 (8)	0.0184 (2)
H34	0.808594	1.032244	−0.097779	0.022*
C35	0.90129 (15)	0.92247 (9)	−0.02165 (8)	0.0186 (2)
H35	0.999785	0.948852	−0.041568	0.022*
C36	0.87189 (14)	0.83442 (9)	0.04111 (8)	0.0168 (2)
H36	0.950247	0.801027	0.063748	0.020*
C37	0.88799 (14)	0.62319 (8)	0.08340 (7)	0.0145 (2)
C38	0.86264 (15)	0.65702 (9)	0.00340 (8)	0.0192 (2)
H38	0.774443	0.686153	−0.008436	0.023*
C39	0.96540 (16)	0.64836 (10)	−0.05883 (8)	0.0222 (3)
H39	0.946888	0.671517	−0.112837	0.027*
C40	1.09477 (16)	0.60612 (9)	−0.04259 (9)	0.0226 (3)
H40	1.164511	0.600156	−0.085274	0.027*
C41	1.12205 (15)	0.57251 (9)	0.03644 (9)	0.0206 (3)
H41	1.210638	0.543670	0.047843	0.025*
C42	1.01925 (14)	0.58124 (9)	0.09874 (8)	0.0172 (2)
H42	1.038596	0.558314	0.152556	0.021*
C43	0.50237 (13)	0.23986 (8)	0.58462 (7)	0.0120 (2)
C44	0.59874 (13)	0.16847 (8)	0.60277 (7)	0.0136 (2)
H44	0.691680	0.176693	0.566382	0.016*
C45	0.56063 (13)	0.08732 (8)	0.67207 (7)	0.0127 (2)
C46	0.41889 (13)	0.07453 (8)	0.72707 (7)	0.0132 (2)
C47	0.32768 (13)	0.14531 (8)	0.71244 (7)	0.0142 (2)
H47	0.236793	0.137546	0.750318	0.017*
C48	0.36715 (13)	0.22959 (8)	0.64178 (7)	0.0126 (2)
C49	0.67019 (13)	0.01680 (8)	0.68874 (7)	0.0133 (2)
C50	0.74324 (14)	−0.00492 (9)	0.62584 (8)	0.0165 (2)
H50	0.717486	0.022263	0.573447	0.020*
C51	0.85324 (15)	−0.06598 (9)	0.63947 (8)	0.0197 (3)
H51	0.901409	−0.080790	0.596500	0.024*
C52	0.89332 (15)	−0.10554 (9)	0.71539 (8)	0.0198 (3)
H52	0.970025	−0.146296	0.724094	0.024*
C53	0.82030 (15)	−0.08504 (9)	0.77862 (8)	0.0189 (2)
H53	0.846503	−0.112295	0.830896	0.023*
C54	0.70939 (14)	−0.02491 (9)	0.76543 (8)	0.0162 (2)
H54	0.659286	−0.011860	0.809141	0.019*
C55	0.36807 (13)	−0.01519 (8)	0.79842 (7)	0.0143 (2)
C56	0.36616 (16)	−0.09418 (9)	0.78719 (8)	0.0212 (3)
H56	0.397645	−0.090807	0.733542	0.025*
C57	0.31856 (18)	−0.17757 (9)	0.85392 (9)	0.0259 (3)
H57	0.316230	−0.230743	0.845538	0.031*
C58	0.27434 (16)	−0.18366 (9)	0.93285 (9)	0.0226 (3)
H58	0.243054	−0.240893	0.978501	0.027*
C59	0.27614 (15)	−0.10594 (9)	0.94456 (8)	0.0184 (2)
H59	0.246541	−0.109943	0.998515	0.022*
C60	0.32114 (14)	−0.02160 (8)	0.87767 (8)	0.0153 (2)
H60	0.319801	0.031642	0.886143	0.018*
Cl1	0.11062 (5)	0.83590 (3)	0.26669 (2)	0.03512 (10)
Cl2	0.17654 (4)	0.72871 (3)	0.17281 (2)	0.02962 (9)
C61	0.10609 (16)	0.72602 (9)	0.27127 (8)	0.0218 (3)
H61A	0.002980	0.699304	0.291784	0.026*
H61B	0.165617	0.686843	0.310597	0.026*
Cl3	0.70558 (5)	0.30628 (3)	0.27367 (2)	0.03072 (9)
Cl4	0.84801 (4)	0.18745 (2)	0.40649 (2)	0.02374 (8)
C62	0.78838 (16)	0.29773 (9)	0.35492 (9)	0.0208 (3)
H62A	0.716264	0.311995	0.394731	0.025*
H62B	0.874064	0.342747	0.332468	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0112 (4)	0.0113 (4)	0.0130 (4)	0.0012 (4)	−0.0023 (4)	−0.0051 (4)
N2	0.0130 (4)	0.0120 (5)	0.0124 (4)	0.0027 (4)	−0.0030 (4)	−0.0051 (4)
N3	0.0135 (5)	0.0116 (5)	0.0116 (4)	0.0015 (4)	−0.0019 (4)	−0.0044 (4)
N4	0.0124 (4)	0.0119 (5)	0.0112 (4)	0.0011 (4)	−0.0016 (4)	−0.0041 (4)
N5	0.0127 (4)	0.0112 (5)	0.0111 (4)	0.0017 (4)	−0.0029 (4)	−0.0040 (4)
N6	0.0127 (4)	0.0119 (5)	0.0120 (4)	0.0020 (4)	−0.0020 (4)	−0.0040 (4)
C1	0.0102 (5)	0.0105 (5)	0.0117 (5)	0.0010 (4)	−0.0033 (4)	−0.0046 (4)
C2	0.0110 (5)	0.0108 (5)	0.0114 (5)	0.0011 (4)	−0.0026 (4)	−0.0047 (4)
C3	0.0106 (5)	0.0109 (5)	0.0110 (5)	0.0006 (4)	−0.0022 (4)	−0.0043 (4)
C4	0.0110 (5)	0.0107 (5)	0.0108 (5)	0.0008 (4)	−0.0025 (4)	−0.0043 (4)
C5	0.0112 (5)	0.0112 (5)	0.0102 (5)	0.0005 (4)	−0.0021 (4)	−0.0044 (4)
C6	0.0112 (5)	0.0110 (5)	0.0115 (5)	0.0013 (4)	−0.0031 (4)	−0.0046 (4)
C7	0.0113 (5)	0.0113 (5)	0.0122 (5)	0.0009 (4)	−0.0024 (4)	−0.0051 (4)
C8	0.0128 (5)	0.0128 (5)	0.0127 (5)	0.0003 (4)	−0.0015 (4)	−0.0048 (4)
C9	0.0111 (5)	0.0142 (5)	0.0135 (5)	0.0004 (4)	−0.0018 (4)	−0.0070 (4)
C10	0.0122 (5)	0.0120 (5)	0.0150 (5)	0.0021 (4)	−0.0034 (4)	−0.0064 (4)
C11	0.0150 (5)	0.0128 (5)	0.0132 (5)	0.0034 (4)	−0.0035 (4)	−0.0042 (4)
C12	0.0122 (5)	0.0121 (5)	0.0121 (5)	0.0012 (4)	−0.0032 (4)	−0.0049 (4)
C13	0.0123 (5)	0.0162 (6)	0.0142 (5)	0.0032 (4)	−0.0038 (4)	−0.0069 (5)
C14	0.0157 (6)	0.0183 (6)	0.0179 (6)	0.0006 (5)	−0.0021 (5)	−0.0079 (5)
C15	0.0184 (6)	0.0267 (7)	0.0185 (6)	−0.0012 (5)	0.0012 (5)	−0.0072 (5)
C16	0.0208 (6)	0.0340 (8)	0.0176 (6)	0.0055 (6)	0.0006 (5)	−0.0129 (6)
C17	0.0267 (7)	0.0270 (7)	0.0212 (6)	0.0066 (6)	−0.0037 (5)	−0.0160 (6)
C18	0.0190 (6)	0.0181 (6)	0.0174 (6)	0.0019 (5)	−0.0021 (5)	−0.0089 (5)
C19	0.0152 (5)	0.0140 (5)	0.0146 (5)	0.0040 (4)	−0.0051 (4)	−0.0075 (5)
C20	0.0152 (5)	0.0163 (6)	0.0190 (6)	0.0027 (4)	−0.0039 (5)	−0.0098 (5)
C21	0.0140 (5)	0.0202 (6)	0.0252 (6)	0.0056 (5)	−0.0055 (5)	−0.0132 (5)
C22	0.0216 (6)	0.0173 (6)	0.0236 (6)	0.0089 (5)	−0.0095 (5)	−0.0104 (5)
C23	0.0228 (6)	0.0140 (6)	0.0185 (6)	0.0033 (5)	−0.0044 (5)	−0.0048 (5)
C24	0.0158 (6)	0.0175 (6)	0.0178 (6)	0.0037 (5)	−0.0022 (5)	−0.0080 (5)
C25	0.0127 (5)	0.0127 (5)	0.0120 (5)	0.0010 (4)	−0.0023 (4)	−0.0048 (4)
C26	0.0150 (5)	0.0117 (5)	0.0138 (5)	0.0025 (4)	−0.0031 (4)	−0.0032 (4)
C27	0.0135 (5)	0.0125 (5)	0.0121 (5)	0.0011 (4)	−0.0031 (4)	−0.0032 (4)
C28	0.0129 (5)	0.0142 (5)	0.0117 (5)	0.0007 (4)	−0.0015 (4)	−0.0044 (4)
C29	0.0142 (5)	0.0128 (5)	0.0139 (5)	0.0028 (4)	−0.0012 (4)	−0.0043 (4)
C30	0.0131 (5)	0.0114 (5)	0.0117 (5)	0.0010 (4)	−0.0026 (4)	−0.0041 (4)
C31	0.0153 (5)	0.0117 (5)	0.0108 (5)	0.0008 (4)	−0.0014 (4)	−0.0030 (4)
C32	0.0140 (5)	0.0176 (6)	0.0137 (5)	0.0018 (4)	−0.0018 (4)	−0.0046 (5)
C33	0.0222 (6)	0.0172 (6)	0.0135 (5)	0.0059 (5)	−0.0049 (5)	−0.0046 (5)
C34	0.0265 (7)	0.0135 (6)	0.0117 (5)	0.0006 (5)	−0.0018 (5)	−0.0033 (5)
C35	0.0179 (6)	0.0164 (6)	0.0171 (6)	−0.0037 (5)	0.0008 (5)	−0.0051 (5)
C36	0.0155 (6)	0.0153 (6)	0.0169 (6)	0.0012 (4)	−0.0032 (5)	−0.0047 (5)
C37	0.0158 (5)	0.0126 (5)	0.0122 (5)	−0.0013 (4)	0.0007 (4)	−0.0043 (4)
C38	0.0226 (6)	0.0170 (6)	0.0150 (6)	0.0012 (5)	−0.0023 (5)	−0.0052 (5)
C39	0.0304 (7)	0.0204 (6)	0.0127 (6)	−0.0022 (5)	0.0003 (5)	−0.0063 (5)
C40	0.0258 (7)	0.0195 (6)	0.0197 (6)	−0.0052 (5)	0.0071 (5)	−0.0108 (5)
C41	0.0176 (6)	0.0182 (6)	0.0236 (6)	−0.0008 (5)	0.0026 (5)	−0.0098 (5)
C42	0.0177 (6)	0.0158 (6)	0.0154 (6)	0.0005 (5)	−0.0008 (5)	−0.0054 (5)
C43	0.0136 (5)	0.0116 (5)	0.0104 (5)	0.0013 (4)	−0.0021 (4)	−0.0048 (4)
C44	0.0137 (5)	0.0138 (5)	0.0122 (5)	0.0032 (4)	−0.0017 (4)	−0.0052 (4)
C45	0.0148 (5)	0.0125 (5)	0.0112 (5)	0.0032 (4)	−0.0031 (4)	−0.0055 (4)
C46	0.0156 (5)	0.0116 (5)	0.0113 (5)	0.0012 (4)	−0.0027 (4)	−0.0041 (4)
C47	0.0143 (5)	0.0130 (5)	0.0122 (5)	0.0013 (4)	−0.0006 (4)	−0.0035 (4)
C48	0.0129 (5)	0.0120 (5)	0.0121 (5)	0.0014 (4)	−0.0025 (4)	−0.0046 (4)
C49	0.0143 (5)	0.0102 (5)	0.0134 (5)	0.0018 (4)	−0.0024 (4)	−0.0035 (4)
C50	0.0197 (6)	0.0153 (6)	0.0144 (5)	0.0038 (5)	−0.0033 (5)	−0.0067 (5)
C51	0.0227 (6)	0.0182 (6)	0.0196 (6)	0.0066 (5)	−0.0030 (5)	−0.0105 (5)
C52	0.0206 (6)	0.0162 (6)	0.0233 (6)	0.0073 (5)	−0.0063 (5)	−0.0090 (5)
C53	0.0228 (6)	0.0162 (6)	0.0172 (6)	0.0062 (5)	−0.0079 (5)	−0.0056 (5)
C54	0.0189 (6)	0.0151 (6)	0.0144 (5)	0.0044 (5)	−0.0035 (5)	−0.0065 (5)
C55	0.0143 (5)	0.0117 (5)	0.0135 (5)	0.0012 (4)	−0.0022 (4)	−0.0028 (4)
C56	0.0297 (7)	0.0156 (6)	0.0164 (6)	−0.0010 (5)	−0.0013 (5)	−0.0066 (5)
C57	0.0372 (8)	0.0130 (6)	0.0238 (7)	−0.0034 (6)	−0.0002 (6)	−0.0073 (5)
C58	0.0266 (7)	0.0133 (6)	0.0200 (6)	−0.0026 (5)	−0.0006 (5)	−0.0015 (5)
C59	0.0193 (6)	0.0169 (6)	0.0137 (5)	0.0003 (5)	0.0000 (5)	−0.0033 (5)
C60	0.0153 (5)	0.0136 (5)	0.0147 (5)	0.0012 (4)	−0.0015 (4)	−0.0048 (5)
Cl1	0.0569 (3)	0.01799 (17)	0.02317 (17)	−0.00789 (16)	−0.00341 (17)	−0.00389 (14)
Cl2	0.03465 (19)	0.0337 (2)	0.01836 (16)	0.00290 (15)	−0.00656 (14)	−0.00909 (14)
C61	0.0273 (7)	0.0158 (6)	0.0156 (6)	−0.0027 (5)	−0.0028 (5)	−0.0013 (5)
Cl3	0.0449 (2)	0.02792 (18)	0.01921 (16)	−0.00109 (16)	−0.01175 (15)	−0.00788 (14)
Cl4	0.02025 (15)	0.02240 (16)	0.02590 (16)	0.00880 (12)	−0.00300 (12)	−0.00941 (13)
C62	0.0233 (6)	0.0187 (6)	0.0233 (6)	0.0049 (5)	−0.0087 (5)	−0.0106 (5)

Geometric parameters (Å, º)

N1—C1	1.3278 (15)	C31—C32	1.4001 (17)
N1—C7	1.3588 (15)	C32—C33	1.3925 (18)
N2—C2	1.3231 (15)	C32—H32	0.9500
N2—C12	1.3513 (15)	C33—C34	1.3854 (19)
N3—C3	1.3279 (15)	C33—H33	0.9500
N3—C25	1.3529 (15)	C34—C35	1.3875 (19)
N4—C4	1.3296 (15)	C34—H34	0.9500
N4—C30	1.3585 (15)	C35—C36	1.3923 (18)
N5—C5	1.3268 (15)	C35—H35	0.9500
N5—C43	1.3528 (15)	C36—H36	0.9500
N6—C6	1.3286 (15)	C37—C42	1.3978 (18)
N6—C48	1.3567 (15)	C37—C38	1.4004 (17)
C1—C2	1.4305 (16)	C38—C39	1.3899 (18)
C1—C6	1.4763 (16)	C38—H38	0.9500
C2—C3	1.4713 (16)	C39—C40	1.387 (2)
C3—C4	1.4263 (16)	C39—H39	0.9500
C4—C5	1.4755 (16)	C40—C41	1.391 (2)
C5—C6	1.4328 (16)	C40—H40	0.9500
C7—C8	1.4159 (16)	C41—C42	1.3915 (18)
C7—C12	1.4192 (16)	C41—H41	0.9500
C8—C9	1.3851 (16)	C42—H42	0.9500
C8—H8	0.9500	C43—C44	1.4136 (16)
C9—C10	1.4526 (17)	C43—C48	1.4244 (16)
C9—C13	1.4939 (16)	C44—C45	1.3759 (17)
C10—C11	1.3792 (16)	C44—H44	0.9500
C10—C19	1.4934 (16)	C45—C46	1.4440 (16)
C11—C12	1.4103 (16)	C45—C49	1.4868 (16)
C11—H11	0.9500	C46—C47	1.3770 (17)
C13—C18	1.3973 (17)	C46—C55	1.4905 (16)
C13—C14	1.3984 (18)	C47—C48	1.4179 (16)
C14—C15	1.3948 (18)	C47—H47	0.9500
C14—H14	0.9500	C49—C54	1.3977 (17)
C15—C16	1.388 (2)	C49—C50	1.3979 (17)
C15—H15	0.9500	C50—C51	1.3891 (18)
C16—C17	1.391 (2)	C50—H50	0.9500
C16—H16	0.9500	C51—C52	1.3880 (19)
C17—C18	1.3907 (18)	C51—H51	0.9500
C17—H17	0.9500	C52—C53	1.3911 (19)
C18—H18	0.9500	C52—H52	0.9500
C19—C20	1.3987 (17)	C53—C54	1.3858 (17)
C19—C24	1.4075 (18)	C53—H53	0.9500
C20—C21	1.3949 (17)	C54—H54	0.9500
C20—H20	0.9500	C55—C60	1.3949 (17)
C21—C22	1.386 (2)	C55—C56	1.3976 (18)
C21—H21	0.9500	C56—C57	1.3889 (19)
C22—C23	1.3877 (19)	C56—H56	0.9500
C22—H22	0.9500	C57—C58	1.389 (2)
C23—C24	1.3915 (18)	C57—H57	0.9500
C23—H23	0.9500	C58—C59	1.3818 (19)
C24—H24	0.9500	C58—H58	0.9500
C25—C26	1.4124 (16)	C59—C60	1.3957 (17)
C25—C30	1.4237 (16)	C59—H59	0.9500
C26—C27	1.3736 (17)	C60—H60	0.9500
C26—H26	0.9500	Cl1—C61	1.7665 (14)
C27—C28	1.4489 (17)	Cl2—C61	1.7812 (14)
C27—C31	1.4865 (16)	C61—H61A	0.9900
C28—C29	1.3798 (17)	C61—H61B	0.9900
C28—C37	1.4920 (16)	Cl3—C62	1.7695 (14)
C29—C30	1.4155 (16)	Cl4—C62	1.7713 (14)
C29—H29	0.9500	C62—H62A	0.9900
C31—C36	1.3983 (17)	C62—H62B	0.9900
C1—N1—C7	116.30 (10)	C33—C32—C31	120.44 (12)
C2—N2—C12	116.39 (10)	C33—C32—H32	119.8
C3—N3—C25	116.16 (10)	C31—C32—H32	119.8
C4—N4—C30	116.49 (10)	C34—C33—C32	120.24 (12)
C5—N5—C43	116.77 (10)	C34—C33—H33	119.9
C6—N6—C48	116.57 (10)	C32—C33—H33	119.9
N1—C1—C2	121.85 (10)	C33—C34—C35	119.71 (12)
N1—C1—C6	118.82 (10)	C33—C34—H34	120.1
C2—C1—C6	119.30 (10)	C35—C34—H34	120.1
N2—C2—C1	122.22 (10)	C34—C35—C36	120.55 (12)
N2—C2—C3	117.20 (10)	C34—C35—H35	119.7
C1—C2—C3	120.56 (10)	C36—C35—H35	119.7
N3—C3—C4	122.47 (10)	C35—C36—C31	120.13 (12)
N3—C3—C2	117.23 (10)	C35—C36—H36	119.9
C4—C3—C2	120.26 (10)	C31—C36—H36	119.9
N4—C4—C3	121.81 (10)	C42—C37—C38	118.35 (11)
N4—C4—C5	118.87 (10)	C42—C37—C28	120.41 (11)
C3—C4—C5	119.32 (10)	C38—C37—C28	121.10 (11)
N5—C5—C6	121.65 (10)	C39—C38—C37	120.58 (13)
N5—C5—C4	117.87 (10)	C39—C38—H38	119.7
C6—C5—C4	120.48 (10)	C37—C38—H38	119.7
N6—C6—C5	121.95 (10)	C40—C39—C38	120.43 (13)
N6—C6—C1	118.34 (10)	C40—C39—H39	119.8
C5—C6—C1	119.70 (10)	C38—C39—H39	119.8
N1—C7—C8	120.43 (11)	C39—C40—C41	119.76 (12)
N1—C7—C12	121.41 (10)	C39—C40—H40	120.1
C8—C7—C12	118.14 (10)	C41—C40—H40	120.1
C9—C8—C7	122.09 (11)	C40—C41—C42	119.84 (13)
C9—C8—H8	119.0	C40—C41—H41	120.1
C7—C8—H8	119.0	C42—C41—H41	120.1
C8—C9—C10	119.46 (10)	C41—C42—C37	121.05 (12)
C8—C9—C13	117.04 (11)	C41—C42—H42	119.5
C10—C9—C13	123.45 (10)	C37—C42—H42	119.5
C11—C10—C9	118.05 (10)	N5—C43—C44	119.26 (10)
C11—C10—C19	116.27 (11)	N5—C43—C48	121.46 (11)
C9—C10—C19	125.65 (10)	C44—C43—C48	119.27 (11)
C10—C11—C12	122.52 (11)	C45—C44—C43	121.32 (11)
C10—C11—H11	118.7	C45—C44—H44	119.3
C12—C11—H11	118.7	C43—C44—H44	119.3
N2—C12—C11	118.80 (11)	C44—C45—C46	119.37 (11)
N2—C12—C7	121.68 (11)	C44—C45—C49	118.20 (11)
C11—C12—C7	119.51 (11)	C46—C45—C49	122.40 (10)
C18—C13—C14	118.81 (11)	C47—C46—C45	119.76 (11)
C18—C13—C9	121.17 (11)	C47—C46—C55	119.40 (11)
C14—C13—C9	119.97 (11)	C45—C46—C55	120.83 (10)
C15—C14—C13	120.58 (12)	C46—C47—C48	121.10 (11)
C15—C14—H14	119.7	C46—C47—H47	119.4
C13—C14—H14	119.7	C48—C47—H47	119.4
C16—C15—C14	119.99 (13)	N6—C48—C47	119.90 (11)
C16—C15—H15	120.0	N6—C48—C43	121.16 (11)
C14—C15—H15	120.0	C47—C48—C43	118.94 (11)
C15—C16—C17	119.89 (12)	C54—C49—C50	118.52 (11)
C15—C16—H16	120.1	C54—C49—C45	121.15 (11)
C17—C16—H16	120.1	C50—C49—C45	120.21 (11)
C16—C17—C18	120.19 (13)	C51—C50—C49	120.42 (12)
C16—C17—H17	119.9	C51—C50—H50	119.8
C18—C17—H17	119.9	C49—C50—H50	119.8
C17—C18—C13	120.53 (13)	C52—C51—C50	120.52 (12)
C17—C18—H18	119.7	C52—C51—H51	119.7
C13—C18—H18	119.7	C50—C51—H51	119.7
C20—C19—C24	117.96 (11)	C51—C52—C53	119.49 (12)
C20—C19—C10	122.87 (11)	C51—C52—H52	120.3
C24—C19—C10	118.98 (11)	C53—C52—H52	120.3
C21—C20—C19	120.42 (12)	C54—C53—C52	120.07 (12)
C21—C20—H20	119.8	C54—C53—H53	120.0
C19—C20—H20	119.8	C52—C53—H53	120.0
C22—C21—C20	120.84 (12)	C53—C54—C49	120.96 (11)
C22—C21—H21	119.6	C53—C54—H54	119.5
C20—C21—H21	119.6	C49—C54—H54	119.5
C21—C22—C23	119.57 (12)	C60—C55—C56	118.87 (11)
C21—C22—H22	120.2	C60—C55—C46	120.40 (11)
C23—C22—H22	120.2	C56—C55—C46	120.73 (11)
C22—C23—C24	119.89 (12)	C57—C56—C55	120.45 (12)
C22—C23—H23	120.1	C57—C56—H56	119.8
C24—C23—H23	120.1	C55—C56—H56	119.8
C23—C24—C19	121.27 (12)	C56—C57—C58	120.36 (13)
C23—C24—H24	119.4	C56—C57—H57	119.8
C19—C24—H24	119.4	C58—C57—H57	119.8
N3—C25—C26	118.94 (11)	C59—C58—C57	119.58 (12)
N3—C25—C30	121.74 (11)	C59—C58—H58	120.2
C26—C25—C30	119.32 (11)	C57—C58—H58	120.2
C27—C26—C25	121.72 (11)	C58—C59—C60	120.47 (12)
C27—C26—H26	119.1	C58—C59—H59	119.8
C25—C26—H26	119.1	C60—C59—H59	119.8
C26—C27—C28	119.20 (11)	C55—C60—C59	120.26 (12)
C26—C27—C31	117.00 (11)	C55—C60—H60	119.9
C28—C27—C31	123.74 (11)	C59—C60—H60	119.9
C29—C28—C27	119.15 (11)	Cl1—C61—Cl2	111.51 (7)
C29—C28—C37	118.19 (11)	Cl1—C61—H61A	109.3
C27—C28—C37	122.53 (11)	Cl2—C61—H61A	109.3
C28—C29—C30	121.82 (11)	Cl1—C61—H61B	109.3
C28—C29—H29	119.1	Cl2—C61—H61B	109.3
C30—C29—H29	119.1	H61A—C61—H61B	108.0
N4—C30—C29	120.21 (11)	Cl3—C62—Cl4	111.38 (7)
N4—C30—C25	121.24 (10)	Cl3—C62—H62A	109.4
C29—C30—C25	118.52 (11)	Cl4—C62—H62A	109.4
C36—C31—C32	118.92 (11)	Cl3—C62—H62B	109.4
C36—C31—C27	121.40 (11)	Cl4—C62—H62B	109.4
C32—C31—C27	119.51 (11)	H62A—C62—H62B	108.0
C7—N1—C1—C2	0.39 (16)	C25—C26—C27—C28	1.87 (18)
C7—N1—C1—C6	178.51 (10)	C25—C26—C27—C31	−175.41 (11)
C12—N2—C2—C1	3.53 (16)	C26—C27—C28—C29	−4.81 (18)
C12—N2—C2—C3	−174.71 (10)	C31—C27—C28—C29	172.28 (11)
N1—C1—C2—N2	−3.64 (17)	C26—C27—C28—C37	171.17 (11)
C6—C1—C2—N2	178.24 (10)	C31—C27—C28—C37	−11.75 (18)
N1—C1—C2—C3	174.54 (10)	C27—C28—C29—C30	2.96 (18)
C6—C1—C2—C3	−3.57 (16)	C37—C28—C29—C30	−173.19 (11)
C25—N3—C3—C4	1.04 (16)	C4—N4—C30—C29	−177.43 (11)
C25—N3—C3—C2	178.61 (10)	C4—N4—C30—C25	0.63 (16)
N2—C2—C3—N3	1.24 (16)	C28—C29—C30—N4	179.89 (11)
C1—C2—C3—N3	−177.04 (10)	C28—C29—C30—C25	1.78 (18)
N2—C2—C3—C4	178.87 (10)	N3—C25—C30—N4	−2.53 (18)
C1—C2—C3—C4	0.59 (16)	C26—C25—C30—N4	177.19 (11)
C30—N4—C4—C3	1.96 (16)	N3—C25—C30—C29	175.56 (11)
C30—N4—C4—C5	−177.66 (10)	C26—C25—C30—C29	−4.72 (17)
N3—C3—C4—N4	−2.97 (18)	C26—C27—C31—C36	130.02 (13)
C2—C3—C4—N4	179.52 (10)	C28—C27—C31—C36	−47.12 (18)
N3—C3—C4—C5	176.64 (10)	C26—C27—C31—C32	−45.20 (16)
C2—C3—C4—C5	−0.86 (16)	C28—C27—C31—C32	137.66 (13)
C43—N5—C5—C6	3.42 (16)	C36—C31—C32—C33	−1.07 (18)
C43—N5—C5—C4	−177.02 (10)	C27—C31—C32—C33	174.26 (11)
N4—C4—C5—N5	4.35 (16)	C31—C32—C33—C34	0.42 (19)
C3—C4—C5—N5	−175.28 (10)	C32—C33—C34—C35	0.43 (19)
N4—C4—C5—C6	−176.09 (10)	C33—C34—C35—C36	−0.6 (2)
C3—C4—C5—C6	4.28 (16)	C34—C35—C36—C31	−0.1 (2)
C48—N6—C6—C5	2.78 (16)	C32—C31—C36—C35	0.90 (19)
C48—N6—C6—C1	−176.00 (10)	C27—C31—C36—C35	−174.34 (12)
N5—C5—C6—N6	−6.51 (18)	C29—C28—C37—C42	−43.08 (17)
C4—C5—C6—N6	173.94 (10)	C27—C28—C37—C42	140.91 (13)
N5—C5—C6—C1	172.25 (10)	C29—C28—C37—C38	132.67 (13)
C4—C5—C6—C1	−7.29 (16)	C27—C28—C37—C38	−43.34 (18)
N1—C1—C6—N6	7.57 (16)	C42—C37—C38—C39	0.43 (19)
C2—C1—C6—N6	−174.26 (10)	C28—C37—C38—C39	−175.40 (12)
N1—C1—C6—C5	−171.24 (10)	C37—C38—C39—C40	−0.1 (2)
C2—C1—C6—C5	6.93 (16)	C38—C39—C40—C41	−0.2 (2)
C1—N1—C7—C8	−175.81 (10)	C39—C40—C41—C42	0.2 (2)
C1—N1—C7—C12	2.53 (16)	C40—C41—C42—C37	0.2 (2)
N1—C7—C8—C9	177.93 (11)	C38—C37—C42—C41	−0.48 (19)
C12—C7—C8—C9	−0.46 (17)	C28—C37—C42—C41	175.38 (12)
C7—C8—C9—C10	3.64 (18)	C5—N5—C43—C44	−179.04 (11)
C7—C8—C9—C13	−173.85 (11)	C5—N5—C43—C48	2.65 (16)
C8—C9—C10—C11	−2.59 (17)	N5—C43—C44—C45	−174.46 (11)
C13—C9—C10—C11	174.73 (11)	C48—C43—C44—C45	3.89 (18)
C8—C9—C10—C19	175.49 (11)	C43—C44—C45—C46	0.48 (18)
C13—C9—C10—C19	−7.18 (18)	C43—C44—C45—C49	−177.63 (11)
C9—C10—C11—C12	−1.63 (18)	C44—C45—C46—C47	−4.07 (17)
C19—C10—C11—C12	−179.89 (11)	C49—C45—C46—C47	173.96 (11)
C2—N2—C12—C11	178.93 (11)	C44—C45—C46—C55	174.32 (11)
C2—N2—C12—C7	−0.57 (17)	C49—C45—C46—C55	−7.66 (17)
C10—C11—C12—N2	−174.68 (11)	C45—C46—C47—C48	3.20 (18)
C10—C11—C12—C7	4.83 (18)	C55—C46—C47—C48	−175.21 (11)
N1—C7—C12—N2	−2.59 (18)	C6—N6—C48—C47	−176.64 (11)
C8—C7—C12—N2	175.78 (11)	C6—N6—C48—C43	3.29 (17)
N1—C7—C12—C11	177.91 (11)	C46—C47—C48—N6	−178.90 (11)
C8—C7—C12—C11	−3.71 (17)	C46—C47—C48—C43	1.18 (18)
C8—C9—C13—C18	131.14 (13)	N5—C43—C48—N6	−6.33 (18)
C10—C9—C13—C18	−46.24 (17)	C44—C43—C48—N6	175.36 (11)
C8—C9—C13—C14	−46.20 (16)	N5—C43—C48—C47	173.60 (11)
C10—C9—C13—C14	136.41 (12)	C44—C43—C48—C47	−4.71 (17)
C18—C13—C14—C15	1.27 (19)	C44—C45—C49—C54	128.73 (13)
C9—C13—C14—C15	178.68 (12)	C46—C45—C49—C54	−49.32 (17)
C13—C14—C15—C16	−0.6 (2)	C44—C45—C49—C50	−47.16 (17)
C14—C15—C16—C17	−0.3 (2)	C46—C45—C49—C50	134.79 (13)
C15—C16—C17—C18	0.7 (2)	C54—C49—C50—C51	−0.62 (19)
C16—C17—C18—C13	0.0 (2)	C45—C49—C50—C51	175.38 (12)
C14—C13—C18—C17	−0.95 (19)	C49—C50—C51—C52	−0.7 (2)
C9—C13—C18—C17	−178.32 (12)	C50—C51—C52—C53	1.3 (2)
C11—C10—C19—C20	143.00 (12)	C51—C52—C53—C54	−0.6 (2)
C9—C10—C19—C20	−35.12 (18)	C52—C53—C54—C49	−0.8 (2)
C11—C10—C19—C24	−31.82 (16)	C50—C49—C54—C53	1.35 (19)
C9—C10—C19—C24	150.07 (12)	C45—C49—C54—C53	−174.61 (12)
C24—C19—C20—C21	0.87 (18)	C47—C46—C55—C60	−54.54 (16)
C10—C19—C20—C21	−174.00 (11)	C45—C46—C55—C60	127.07 (13)
C19—C20—C21—C22	1.38 (19)	C47—C46—C55—C56	125.28 (14)
C20—C21—C22—C23	−2.2 (2)	C45—C46—C55—C56	−53.11 (17)
C21—C22—C23—C24	0.8 (2)	C60—C55—C56—C57	−0.1 (2)
C22—C23—C24—C19	1.5 (2)	C46—C55—C56—C57	−179.94 (13)
C20—C19—C24—C23	−2.31 (19)	C55—C56—C57—C58	−1.0 (2)
C10—C19—C24—C23	172.76 (11)	C56—C57—C58—C59	0.8 (2)
C3—N3—C25—C26	−178.15 (11)	C57—C58—C59—C60	0.4 (2)
C3—N3—C25—C30	1.57 (17)	C56—C55—C60—C59	1.33 (19)
N3—C25—C26—C27	−177.36 (11)	C46—C55—C60—C59	−178.84 (12)
C30—C25—C26—C27	2.91 (18)	C58—C59—C60—C55	−1.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C61—H61A···N1^i	0.99	2.46	3.2380 (17)	135
C61—H61B···N2	0.99	2.40	3.2745 (17)	146
C61—H61B···N3	0.99	2.61	3.4923 (18)	149
C62—H62A···N4	0.99	2.58	3.2547 (17)	126
C62—H62A···N5	0.99	2.46	3.4381 (17)	169

Symmetry code: (i) −x, −y+1, −z+1.