Polymorph β of 1H-benzotriazole

A new polymorph of 1H-benzotriazole, C₆H₅N₃, with a melting point of 372 K and a crystal density of 1.33 Mg m⁻³, has been obtained by recrystallization from acetone. The triclinic unit cell contains ten mol­ecules joined by N—H...N hydrogen bonds into a discrete large supramolecular macrocycle.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.044
• wR factor = 0.105
• Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1A    -   C8A     ..       5.73 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C5B    -   C6B     ..       5.62 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N3D    -   C9D     ..       5.30 su
PLAT353_ALERT_3_C Long    N-H Bond (0.87A)   N1C    -   H1C    ...       1.02 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              C6 H5 N3
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          4
              C6 H5 N3

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXL97.

1H-Triazole

Crystal data

C6H5N3	Z = 10
Mr = 119.13	F(000) = 620
Triclinic, P1	Dx = 1.329 Mg m^−3
Hall symbol: - P 1	Melting point: 372 K
a = 4.2422 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 17.827 (6) Å	Cell parameters from 1854 reflections
c = 20.685 (7) Å	θ = 3–25°
α = 72.63 (3)°	µ = 0.09 mm^−1
β = 87.15 (2)°	T = 294 K
γ = 86.23 (3)°	Needle, colorless
V = 1489.0 (8) Å^3	0.50 × 0.15 × 0.03 mm

Data collection

Kuma KM4CCD κ geometry diffractometer	2688 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
Graphite monochromator	θmax = 25.0°, θmin = 4.1°
ω scans	h = −5→4
11571 measured reflections	k = −21→21
5181 independent reflections	l = −24→21

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)] = 0.044	Hydrogen site location: difference Fourier map
wR(F^2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	w = 1/[σ^2(Fo^2) + (0.0454P)^2] where P = (Fo^2 + 2Fc^2)/3
5181 reflections	(Δ/σ)max < 0.001
426 parameters	Δρmax = 0.11 e Å^−3
0 restraints	Δρmin = −0.18 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. 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
N1A	0.3578 (5)	0.33353 (12)	0.15913 (11)	0.0741 (6)
H1A	0.318 (6)	0.3045 (15)	0.1298 (13)	0.114 (10)*
N2A	0.2496 (5)	0.31403 (11)	0.22389 (11)	0.0847 (6)
N3A	0.3282 (5)	0.36777 (11)	0.25028 (9)	0.0746 (6)
C4A	0.6165 (6)	0.49234 (13)	0.20429 (12)	0.0720 (7)
H4A	0.6069	0.5071	0.2439	0.086*
C5A	0.7569 (6)	0.53672 (14)	0.14663 (16)	0.0847 (8)
H5A	0.8458	0.5830	0.1467	0.102*
C6A	0.7722 (6)	0.51507 (16)	0.08708 (14)	0.0893 (8)
H6A	0.8681	0.5477	0.0484	0.107*
C7A	0.6507 (6)	0.44742 (15)	0.08379 (11)	0.0788 (7)
H7A	0.6642	0.4325	0.0443	0.095*
C8A	0.5061 (5)	0.40223 (12)	0.14265 (10)	0.0572 (6)
C9A	0.4867 (5)	0.42346 (12)	0.20166 (10)	0.0551 (6)
N1B	0.1888 (5)	0.30865 (12)	0.39099 (11)	0.0689 (6)
H1B	0.207 (6)	0.3414 (15)	0.3451 (13)	0.127 (11)*
N2B	0.0046 (5)	0.33190 (12)	0.43684 (12)	0.0860 (6)
N3B	0.0266 (5)	0.27699 (14)	0.49515 (10)	0.0816 (6)
C4B	0.3349 (7)	0.14555 (16)	0.53218 (11)	0.0794 (8)
H4B	0.2699	0.1310	0.5776	0.095*
C5B	0.5380 (7)	0.09846 (16)	0.50662 (14)	0.0878 (8)
H5B	0.6118	0.0504	0.5353	0.105*
C6B	0.6388 (6)	0.12011 (16)	0.43874 (13)	0.0816 (7)
H6B	0.7780	0.0860	0.4236	0.098*
C7B	0.5410 (5)	0.18886 (15)	0.39433 (11)	0.0679 (6)
H7B	0.6095	0.2030	0.3491	0.081*
C8B	0.3333 (5)	0.23747 (14)	0.41948 (10)	0.0559 (6)
C9B	0.2284 (6)	0.21709 (15)	0.48658 (10)	0.0627 (6)
N1C	−0.3832 (5)	0.27657 (11)	0.60894 (10)	0.0665 (5)
H1C	−0.237 (6)	0.2751 (14)	0.5685 (13)	0.117 (9)*
N2C	−0.3926 (5)	0.21120 (11)	0.66150 (11)	0.0760 (6)
N3C	−0.5863 (5)	0.22501 (11)	0.70836 (9)	0.0717 (5)
C4C	−0.9097 (6)	0.3461 (2)	0.71519 (14)	0.0865 (8)
H4C	−0.9981	0.3252	0.7584	0.104*
C5C	−0.9766 (7)	0.4220 (2)	0.6779 (2)	0.1084 (11)
H5C	−1.1134	0.4537	0.6963	0.130*
C6C	−0.8467 (9)	0.45342 (17)	0.6133 (2)	0.1087 (10)
H6C	−0.9002	0.5055	0.5898	0.130*
C7C	−0.6466 (7)	0.41139 (15)	0.58342 (13)	0.0846 (8)
H7C	−0.5623	0.4327	0.5399	0.102*
C8C	−0.5731 (5)	0.33447 (12)	0.62120 (10)	0.0555 (5)
C9C	−0.7017 (5)	0.30125 (14)	0.68522 (10)	0.0577 (6)
N1D	−0.7189 (5)	0.06114 (13)	0.78499 (11)	0.0675 (6)
H1D	−0.703 (6)	0.1135 (15)	0.7681 (12)	0.107 (10)*
N2D	−0.5531 (5)	0.02014 (14)	0.83986 (10)	0.0781 (6)
N3D	−0.5823 (5)	−0.05494 (11)	0.84833 (9)	0.0697 (5)
C4D	−0.8592 (5)	−0.12914 (12)	0.78373 (11)	0.0608 (6)
H4D	−0.8003	−0.1794	0.8108	0.073*
C5D	−1.0403 (6)	−0.11808 (14)	0.72915 (12)	0.0686 (6)
H5D	−1.1036	−0.1615	0.7181	0.082*
C6D	−1.1332 (5)	−0.04258 (15)	0.68933 (11)	0.0701 (6)
H6D	−1.2625	−0.0373	0.6530	0.084*
C7D	−1.0427 (5)	0.02328 (13)	0.70147 (10)	0.0626 (6)
H7D	−1.1036	0.0733	0.6741	0.075*
C8D	−0.8534 (5)	0.01219 (12)	0.75703 (10)	0.0517 (5)
C9D	−0.7645 (5)	−0.06242 (12)	0.79778 (10)	0.0508 (5)
N1E	0.2275 (5)	0.17641 (12)	0.05792 (9)	0.0633 (5)
H1E	0.343 (6)	0.1334 (15)	0.0889 (12)	0.112 (10)*
N2E	0.1896 (5)	0.24789 (13)	0.06686 (10)	0.0756 (6)
N3E	0.0136 (5)	0.29397 (11)	0.01947 (11)	0.0794 (6)
C4E	−0.2484 (6)	0.27152 (18)	−0.07915 (13)	0.0885 (8)
H4E	−0.3433	0.3217	−0.0961	0.106*
C5E	−0.2808 (7)	0.2141 (3)	−0.10908 (14)	0.1092 (11)
H5E	−0.3993	0.2259	−0.1478	0.131*
C6E	−0.1437 (8)	0.1388 (2)	−0.08395 (16)	0.0993 (10)
H6E	−0.1751	0.1016	−0.1060	0.119*
C7E	0.0340 (6)	0.11780 (14)	−0.02828 (13)	0.0776 (7)
H3E	0.1266	0.0673	−0.0117	0.093*
C8E	0.0711 (5)	0.17539 (12)	0.00272 (10)	0.0520 (5)
C9E	−0.0638 (5)	0.25073 (13)	−0.02144 (11)	0.0588 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.1034 (17)	0.0589 (13)	0.0643 (14)	−0.0004 (12)	−0.0179 (12)	−0.0232 (11)
N2A	0.1135 (18)	0.0603 (13)	0.0753 (15)	−0.0148 (12)	−0.0070 (12)	−0.0095 (11)
N3A	0.1010 (16)	0.0642 (13)	0.0578 (12)	−0.0091 (12)	−0.0027 (11)	−0.0157 (11)
C4A	0.0752 (18)	0.0674 (16)	0.0815 (17)	−0.0017 (14)	−0.0030 (14)	−0.0346 (14)
C5A	0.0757 (19)	0.0594 (16)	0.117 (2)	−0.0105 (14)	0.0065 (16)	−0.0238 (17)
C6A	0.093 (2)	0.0743 (19)	0.0840 (19)	0.0003 (16)	0.0194 (15)	−0.0027 (15)
C7A	0.100 (2)	0.0768 (18)	0.0547 (14)	0.0105 (16)	0.0027 (13)	−0.0163 (14)
C8A	0.0747 (16)	0.0444 (13)	0.0510 (13)	0.0068 (12)	−0.0093 (11)	−0.0127 (11)
C9A	0.0634 (15)	0.0489 (13)	0.0522 (13)	0.0008 (12)	−0.0067 (11)	−0.0140 (11)
N1B	0.0813 (15)	0.0655 (14)	0.0595 (13)	−0.0059 (12)	0.0097 (11)	−0.0193 (12)
N2B	0.1002 (17)	0.0784 (15)	0.0857 (15)	0.0010 (13)	0.0099 (13)	−0.0370 (14)
N3B	0.0965 (17)	0.0903 (16)	0.0656 (13)	−0.0137 (14)	0.0183 (12)	−0.0359 (13)
C4B	0.102 (2)	0.0887 (19)	0.0449 (13)	−0.0337 (17)	−0.0018 (14)	−0.0098 (15)
C5B	0.105 (2)	0.0697 (17)	0.084 (2)	−0.0047 (17)	−0.0262 (16)	−0.0129 (16)
C6B	0.085 (2)	0.085 (2)	0.0794 (18)	0.0030 (16)	−0.0085 (15)	−0.0325 (16)
C7B	0.0713 (17)	0.0801 (17)	0.0553 (14)	−0.0069 (14)	0.0035 (12)	−0.0248 (14)
C8B	0.0627 (15)	0.0588 (15)	0.0489 (13)	−0.0108 (13)	0.0030 (11)	−0.0192 (11)
C9B	0.0761 (17)	0.0717 (16)	0.0456 (13)	−0.0217 (14)	0.0079 (12)	−0.0234 (13)
N1C	0.0865 (15)	0.0583 (13)	0.0553 (12)	0.0000 (11)	0.0066 (11)	−0.0199 (11)
N2C	0.0982 (17)	0.0518 (12)	0.0800 (14)	0.0012 (11)	−0.0097 (12)	−0.0226 (12)
N3C	0.0920 (16)	0.0619 (14)	0.0598 (12)	−0.0189 (12)	0.0010 (11)	−0.0134 (10)
C4C	0.0743 (19)	0.116 (2)	0.0882 (18)	−0.0175 (18)	0.0127 (15)	−0.0599 (19)
C5C	0.078 (2)	0.117 (3)	0.165 (3)	0.014 (2)	−0.009 (2)	−0.097 (3)
C6C	0.108 (3)	0.068 (2)	0.154 (3)	0.0121 (19)	−0.031 (2)	−0.038 (2)
C7C	0.098 (2)	0.0594 (17)	0.0871 (18)	−0.0065 (16)	−0.0068 (15)	−0.0064 (15)
C8C	0.0653 (16)	0.0472 (13)	0.0556 (13)	−0.0063 (12)	−0.0008 (11)	−0.0171 (11)
C9C	0.0636 (16)	0.0582 (15)	0.0578 (14)	−0.0154 (13)	0.0045 (11)	−0.0255 (12)
N1D	0.0765 (15)	0.0513 (13)	0.0727 (14)	−0.0082 (12)	0.0154 (11)	−0.0170 (12)
N2D	0.0849 (16)	0.0855 (16)	0.0680 (13)	−0.0174 (13)	0.0044 (11)	−0.0272 (12)
N3D	0.0754 (14)	0.0671 (14)	0.0605 (12)	−0.0047 (11)	−0.0001 (10)	−0.0099 (10)
C4D	0.0627 (16)	0.0420 (13)	0.0675 (15)	0.0014 (12)	0.0139 (12)	−0.0041 (11)
C5D	0.0684 (17)	0.0648 (16)	0.0768 (16)	−0.0093 (13)	0.0097 (13)	−0.0278 (13)
C6D	0.0659 (17)	0.0827 (18)	0.0596 (14)	−0.0050 (15)	0.0008 (11)	−0.0184 (14)
C7D	0.0634 (16)	0.0543 (14)	0.0557 (13)	0.0049 (12)	0.0085 (12)	0.0023 (11)
C8D	0.0560 (15)	0.0434 (13)	0.0508 (12)	−0.0028 (11)	0.0116 (11)	−0.0085 (11)
C9D	0.0509 (14)	0.0480 (13)	0.0476 (12)	−0.0018 (11)	0.0074 (10)	−0.0067 (10)
N1E	0.0788 (15)	0.0512 (12)	0.0557 (12)	−0.0110 (11)	−0.0021 (10)	−0.0082 (10)
N2E	0.1010 (17)	0.0691 (14)	0.0650 (13)	−0.0237 (13)	0.0097 (11)	−0.0303 (11)
N3E	0.0975 (17)	0.0556 (12)	0.0863 (15)	−0.0110 (12)	0.0141 (13)	−0.0239 (12)
C4E	0.0685 (19)	0.099 (2)	0.0742 (18)	−0.0063 (16)	−0.0002 (15)	0.0110 (17)
C5E	0.082 (2)	0.177 (4)	0.0628 (18)	−0.046 (3)	−0.0014 (15)	−0.019 (2)
C6E	0.093 (2)	0.144 (3)	0.086 (2)	−0.051 (2)	0.0214 (18)	−0.067 (2)
C7E	0.0796 (19)	0.0766 (17)	0.0892 (18)	−0.0201 (14)	0.0101 (15)	−0.0423 (15)
C8E	0.0563 (14)	0.0533 (14)	0.0472 (12)	−0.0113 (12)	0.0067 (10)	−0.0160 (11)
C9E	0.0629 (16)	0.0548 (14)	0.0549 (13)	−0.0086 (12)	0.0089 (11)	−0.0111 (12)

Geometric parameters (Å, º)

N1A—N2A	1.345 (2)	C5C—C6C	1.388 (4)
N1A—C8A	1.357 (3)	C5C—H5C	0.9300
N1A—H1A	0.93 (3)	C6C—C7C	1.343 (4)
N2A—N3A	1.304 (2)	C6C—H6C	0.9300
N3A—C9A	1.369 (2)	C7C—C8C	1.385 (3)
C4A—C5A	1.353 (3)	C7C—H7C	0.9300
C4A—C9A	1.395 (3)	C8C—C9C	1.380 (3)
C4A—H4A	0.9300	N1D—C8D	1.350 (3)
C5A—C6A	1.394 (3)	N1D—N2D	1.354 (3)
C5A—H5A	0.9300	N1D—H1D	0.90 (3)
C6A—C7A	1.363 (3)	N2D—N3D	1.310 (2)
C6A—H6A	0.9300	N3D—C9D	1.373 (2)
C7A—C8A	1.383 (3)	C4D—C5D	1.355 (3)
C7A—H7A	0.9300	C4D—C9D	1.393 (3)
C8A—C9A	1.379 (3)	C4D—H4D	0.9300
N1B—N2B	1.342 (2)	C5D—C6D	1.395 (3)
N1B—C8B	1.349 (3)	C5D—H5D	0.9300
N1B—H1B	0.96 (3)	C6D—C7D	1.354 (3)
N2B—N3B	1.310 (2)	C6D—H6D	0.9300
N3B—C9B	1.372 (3)	C7D—C8D	1.393 (3)
C4B—C5B	1.360 (3)	C7D—H7D	0.9300
C4B—C9B	1.403 (3)	C8D—C9D	1.385 (3)
C4B—H4B	0.9300	N1E—N2E	1.340 (2)
C5B—C6B	1.393 (3)	N1E—C8E	1.354 (2)
C5B—H5B	0.9300	N1E—H1E	0.96 (3)
C6B—C7B	1.348 (3)	N2E—N3E	1.306 (2)
C6B—H6B	0.9300	N3E—C9E	1.367 (3)
C7B—C8B	1.386 (3)	C4E—C5E	1.362 (4)
C7B—H7B	0.9300	C4E—C9E	1.402 (3)
C8B—C9B	1.384 (3)	C4E—H4E	0.9300
N1C—N2C	1.337 (2)	C5E—C6E	1.387 (4)
N1C—C8C	1.344 (3)	C5E—H5E	0.9300
N1C—H1C	1.02 (3)	C6E—C7E	1.352 (4)
N2C—N3C	1.309 (2)	C6E—H6E	0.9300
N3C—C9C	1.365 (3)	C7E—C8E	1.384 (3)
C4C—C5C	1.361 (4)	C7E—H3E	0.9300
C4C—C9C	1.397 (3)	C8E—C9E	1.381 (3)
C4C—H4C	0.9300
N2A—N1A—C8A	110.8 (2)	C7C—C6C—H6C	118.8
N2A—N1A—H1A	122.6 (16)	C5C—C6C—H6C	118.8
C8A—N1A—H1A	126.4 (15)	C6C—C7C—C8C	116.1 (3)
N3A—N2A—N1A	108.10 (19)	C6C—C7C—H7C	121.9
N2A—N3A—C9A	108.51 (17)	C8C—C7C—H7C	121.9
C5A—C4A—C9A	117.0 (2)	N1C—C8C—C9C	104.42 (19)
C5A—C4A—H4A	121.5	N1C—C8C—C7C	132.8 (2)
C9A—C4A—H4A	121.5	C9C—C8C—C7C	122.7 (2)
C4A—C5A—C6A	121.9 (2)	N3C—C9C—C8C	108.5 (2)
C4A—C5A—H5A	119.0	N3C—C9C—C4C	131.4 (2)
C6A—C5A—H5A	119.0	C8C—C9C—C4C	120.1 (2)
C7A—C6A—C5A	122.0 (2)	C8D—N1D—N2D	110.99 (19)
C7A—C6A—H6A	119.0	C8D—N1D—H1D	128.3 (16)
C5A—C6A—H6A	119.0	N2D—N1D—H1D	119.9 (16)
C6A—C7A—C8A	116.1 (2)	N3D—N2D—N1D	107.78 (19)
C6A—C7A—H7A	121.9	N2D—N3D—C9D	108.48 (18)
C8A—C7A—H7A	121.9	C5D—C4D—C9D	117.6 (2)
N1A—C8A—C9A	104.0 (2)	C5D—C4D—H4D	121.2
N1A—C8A—C7A	133.6 (2)	C9D—C4D—H4D	121.2
C9A—C8A—C7A	122.4 (2)	C4D—C5D—C6D	121.1 (2)
N3A—C9A—C8A	108.61 (18)	C4D—C5D—H5D	119.4
N3A—C9A—C4A	130.8 (2)	C6D—C5D—H5D	119.4
C8A—C9A—C4A	120.6 (2)	C7D—C6D—C5D	122.6 (2)
N2B—N1B—C8B	110.8 (2)	C7D—C6D—H6D	118.7
N2B—N1B—H1B	120.9 (16)	C5D—C6D—H6D	118.7
C8B—N1B—H1B	128.3 (16)	C6D—C7D—C8D	116.5 (2)
N3B—N2B—N1B	108.2 (2)	C6D—C7D—H7D	121.7
N2B—N3B—C9B	108.41 (18)	C8D—C7D—H7D	121.7
C5B—C4B—C9B	116.7 (2)	N1D—C8D—C9D	104.30 (19)
C5B—C4B—H4B	121.7	N1D—C8D—C7D	134.2 (2)
C9B—C4B—H4B	121.7	C9D—C8D—C7D	121.5 (2)
C4B—C5B—C6B	122.0 (2)	N3D—C9D—C8D	108.44 (18)
C4B—C5B—H5B	119.0	N3D—C9D—C4D	130.9 (2)
C6B—C5B—H5B	119.0	C8D—C9D—C4D	120.7 (2)
C7B—C6B—C5B	122.1 (2)	N2E—N1E—C8E	109.84 (19)
C7B—C6B—H6B	118.9	N2E—N1E—H1E	122.2 (14)
C5B—C6B—H6B	118.9	C8E—N1E—H1E	127.9 (14)
C6B—C7B—C8B	116.6 (2)	N3E—N2E—N1E	109.63 (18)
C6B—C7B—H7B	121.7	N2E—N3E—C9E	107.18 (18)
C8B—C7B—H7B	121.7	C5E—C4E—C9E	116.3 (3)
N1B—C8B—C9B	104.5 (2)	C5E—C4E—H4E	121.9
N1B—C8B—C7B	133.2 (2)	C9E—C4E—H4E	121.9
C9B—C8B—C7B	122.3 (2)	C4E—C5E—C6E	122.5 (3)
N3B—C9B—C8B	108.0 (2)	C4E—C5E—H5E	118.8
N3B—C9B—C4B	131.7 (2)	C6E—C5E—H5E	118.8
C8B—C9B—C4B	120.2 (2)	C7E—C6E—C5E	121.9 (3)
N2C—N1C—C8C	110.64 (19)	C7E—C6E—H6E	119.0
N2C—N1C—H1C	117.6 (14)	C5E—C6E—H6E	119.0
C8C—N1C—H1C	131.7 (14)	C6E—C7E—C8E	116.5 (3)
N3C—N2C—N1C	108.62 (19)	C6E—C7E—H3E	121.7
N2C—N3C—C9C	107.78 (18)	C8E—C7E—H3E	121.7
C5C—C4C—C9C	116.6 (3)	N1E—C8E—C9E	104.30 (19)
C5C—C4C—H4C	121.7	N1E—C8E—C7E	133.2 (2)
C9C—C4C—H4C	121.7	C9E—C8E—C7E	122.5 (2)
C4C—C5C—C6C	121.9 (3)	N3E—C9E—C8E	109.05 (19)
C4C—C5C—H5C	119.0	N3E—C9E—C4E	130.6 (3)
C6C—C5C—H5C	119.0	C8E—C9E—C4E	120.4 (2)
C7C—C6C—C5C	122.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···N2E	0.93 (3)	1.99 (3)	2.916 (3)	174 (2)
N1B—H1B···N3A	0.96 (3)	1.93 (3)	2.831 (3)	157 (2)
N1C—H1C···N3B	1.02 (3)	1.83 (3)	2.854 (3)	178 (2)
N1D—H1D···N3C	0.90 (3)	2.08 (3)	2.954 (3)	164 (2)
N1E—H1E···N3D^i	0.96 (3)	1.88 (3)	2.841 (3)	176 (2)

Symmetry code: (i) −x, −y, −z+1.