4-(Piperidin-1-yl)-4H-benzo[b]tetra-zolo[1,5-d][1,4]diazepin-5(6H)-one.

There are two crystallographically unique mol-ecules present in the asymmetric unit of the title compound, C(14)H(16)N(6)O; in both mol-ecules, the seven-membered diazepinone ring adopts a boat-like conformation and the chair conformation piperidine ring is an axial substituent on the diazepinone ring. In the crystal, each mol-ecule forms hydrogen bonds with its respective symmetry equivalents. Hydrogen bonding between mol-ecule A and symmetry equivalents forms two ring motifs, the first formed by inversion-related N-H⋯O inter-actions and the second formed by C-H⋯O and C-H⋯N inter-actions. The combination of both ring motifs results in the formation of an infinite double tape, which propagates in the a-axis direction. Hydrogen bonding between mol-ecule B and symmetry equivalents forms one ring motif by inversion-related N-H⋯O inter-actions and a second ring motif by C-H⋯O inter-actions, which propagate as a single tape parallel with the c axis.

Related literature

The structure of the title compound was determined as part of a larger study on development of synthetic methods for high-throughput medicinal chemistry. For background to the use of multi-component reactions in high-throughput medicinal chemistry, see: Gunawan et al. (2010 ▶); Hulme & Dietrich (2009 ▶); Hulme & Gore (2003 ▶). For the Ugi reaction, see: Ugi & Steinbrückner (1961 ▶). For graph-set notation for hydrogen bonding, see: Bernstein et al. (1995 ▶) and puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C14H16N6O

M = 284.33

Triclinic,

a = 8.8210 (7) Å

b = 13.1802 (10) Å

c = 13.4476 (11) Å

α = 105.549 (2)°

β = 99.490 (2)°

γ = 106.623 (2)°

V = 1392.99 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.39 × 0.28 × 0.09 mm

Data collection

Bruker Kappa APEXII DUO CCD diffractometer

Absorption correction: numerical (SADABS; Sheldrick, 1996 ▶) T min = 0.965, T max = 0.992

51078 measured reflections

12177 independent reflections

9733 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.123

S = 1.05

12177 reflections

507 parameters

All H-atom parameters refined

Δρmax = 0.59 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al. 2008 ▶); software used to prepare material for publication: SHELXTL and local programs.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810049950/kj2167sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049950/kj2167Isup2.hkl

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

C14H16N6O	Z = 4
Mr = 284.33	F(000) = 600
Triclinic, P1	Dx = 1.356 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8210 (7) Å	Cell parameters from 9970 reflections
b = 13.1802 (10) Å	θ = 2.5–35.5°
c = 13.4476 (11) Å	µ = 0.09 mm−1
α = 105.549 (2)°	T = 100 K
β = 99.490 (2)°	Prism, colourless
γ = 106.623 (2)°	0.39 × 0.28 × 0.09 mm
V = 1392.99 (19) Å3

Bruker Kappa APEXII DUO CCD diffractometer	12177 independent reflections
Radiation source: fine-focus sealed tube with Miracol optics	9733 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 35.0°, θmin = 1.6°
Absorption correction: numerical (SADABS; Sheldrick, 1996)	h = −8→14
Tmin = 0.965, Tmax = 0.992	k = −21→21
51078 measured reflections	l = −21→19

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)] = 0.043	Hydrogen site location: difference Fourier map
wR(F2) = 0.123	All H-atom parameters refined
S = 1.05	w = 1/[σ2(Fo2) + (0.0711P)2 + 0.1991P] where P = (Fo2 + 2Fc2)/3
12177 reflections	(Δ/σ)max < 0.001
507 parameters	Δρmax = 0.59 e Å−3
0 restraints	Δρmin = −0.23 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
O1	0.38761 (7)	0.05350 (5)	0.43124 (5)	0.01571 (11)
N1	0.60561 (8)	0.01832 (6)	0.38204 (5)	0.01320 (11)
H1N	0.6179 (16)	−0.0054 (11)	0.4346 (11)	0.022 (3)*
N2	0.28444 (8)	−0.02275 (6)	0.10021 (5)	0.01491 (11)
N3	0.31273 (9)	−0.10081 (6)	0.02234 (5)	0.01668 (12)
N4	0.45718 (9)	−0.10612 (6)	0.05193 (5)	0.01538 (12)
N5	0.52683 (8)	−0.02989 (5)	0.15250 (5)	0.01189 (10)
N6	0.60485 (8)	0.20364 (5)	0.29571 (5)	0.01251 (11)
C1	0.48112 (9)	0.05928 (6)	0.37255 (6)	0.01170 (11)
C2	0.45700 (9)	0.11124 (6)	0.28435 (6)	0.01159 (11)
H2	0.3595 (15)	0.1330 (10)	0.2855 (10)	0.017 (3)*
C3	0.41921 (9)	0.02050 (6)	0.17984 (6)	0.01156 (11)
C4	0.68763 (9)	−0.01103 (6)	0.21140 (6)	0.01208 (12)
C5	0.80602 (10)	−0.02132 (7)	0.15637 (7)	0.01617 (13)
H5	0.7760 (17)	−0.0426 (12)	0.0765 (11)	0.027 (3)*
C6	0.96362 (10)	−0.00308 (7)	0.21295 (7)	0.01873 (14)
H6	1.0457 (18)	−0.0093 (12)	0.1781 (12)	0.030 (3)*
C7	1.00262 (10)	0.02641 (7)	0.32418 (7)	0.01900 (14)
H7	1.1107 (19)	0.0416 (12)	0.3635 (12)	0.033 (4)*
C8	0.88362 (9)	0.03591 (7)	0.37831 (7)	0.01614 (13)
H8	0.9081 (16)	0.0536 (11)	0.4581 (11)	0.022 (3)*
C9	0.72383 (9)	0.01681 (6)	0.32280 (6)	0.01220 (12)
C10	0.57954 (10)	0.25511 (7)	0.21242 (6)	0.01617 (13)
H10A	0.5286 (16)	0.1938 (11)	0.1401 (11)	0.023 (3)*
H10B	0.4961 (17)	0.2921 (11)	0.2234 (11)	0.025 (3)*
C11	0.74158 (12)	0.33854 (7)	0.21560 (8)	0.02248 (16)
H11A	0.8144 (18)	0.2980 (13)	0.1966 (12)	0.033 (4)*
H11	0.722 (2)	0.3742 (13)	0.1604 (13)	0.040 (4)*
C12	0.81799 (14)	0.42864 (8)	0.32592 (9)	0.02767 (19)
H12A	0.753 (2)	0.4792 (14)	0.3395 (13)	0.039 (4)*
H12B	0.933 (2)	0.4793 (14)	0.3300 (13)	0.039 (4)*
C13	0.82547 (12)	0.37556 (8)	0.41398 (8)	0.02422 (17)
H13A	0.9033 (18)	0.3335 (12)	0.4088 (12)	0.031 (4)*
H13B	0.8589 (17)	0.4330 (12)	0.4846 (11)	0.027 (3)*
C14	0.65953 (10)	0.28969 (7)	0.40202 (6)	0.01774 (14)
H14A	0.6707 (17)	0.2514 (11)	0.4561 (11)	0.026 (3)*
H14B	0.5794 (18)	0.3278 (12)	0.4109 (11)	0.029 (3)*
O51	0.52486 (10)	0.64389 (6)	0.05346 (5)	0.02384 (13)
N51	0.40757 (10)	0.50343 (6)	0.11293 (6)	0.01766 (13)
H51N	0.4212 (19)	0.4560 (13)	0.0574 (13)	0.036 (4)*
N52	0.67271 (10)	0.77756 (6)	0.37934 (6)	0.02130 (14)
N53	0.72173 (10)	0.73295 (7)	0.45426 (6)	0.02402 (15)
N54	0.62468 (10)	0.63061 (7)	0.43334 (6)	0.02147 (14)
N55	0.50786 (9)	0.60616 (6)	0.34204 (5)	0.01671 (12)
N56	0.26638 (9)	0.67324 (6)	0.22010 (5)	0.01605 (12)
C51	0.45755 (11)	0.61293 (7)	0.11881 (6)	0.01729 (14)
C52	0.43580 (10)	0.69955 (6)	0.21216 (6)	0.01637 (13)
H52	0.4837 (16)	0.7759 (11)	0.2025 (10)	0.020 (3)*
C53	0.53997 (10)	0.69786 (7)	0.31100 (6)	0.01685 (13)
C54	0.38196 (10)	0.49889 (6)	0.29242 (6)	0.01599 (13)
C55	0.31368 (11)	0.44075 (7)	0.35588 (7)	0.01975 (15)
H55	0.3508 (16)	0.4735 (11)	0.4336 (11)	0.022 (3)*
C56	0.19621 (11)	0.33379 (8)	0.30809 (8)	0.02194 (16)
H56	0.1541 (17)	0.2909 (12)	0.3505 (11)	0.027 (3)*
C57	0.14557 (11)	0.28606 (7)	0.19694 (8)	0.02214 (16)
H57	0.0629 (17)	0.2098 (12)	0.1595 (12)	0.029 (3)*
C58	0.21359 (11)	0.34480 (7)	0.13379 (7)	0.01951 (15)
H58	0.1781 (17)	0.3104 (12)	0.0555 (11)	0.027 (3)*
C59	0.33285 (10)	0.45203 (6)	0.18068 (6)	0.01597 (13)
C60	0.14703 (12)	0.64876 (7)	0.11863 (7)	0.02103 (15)
H60	0.1632 (16)	0.7177 (11)	0.1003 (11)	0.023 (3)*
H60B	0.1633 (17)	0.5889 (12)	0.0625 (11)	0.028 (3)*
C61	−0.02563 (12)	0.60567 (8)	0.13221 (8)	0.02450 (17)
H61A	−0.1061 (19)	0.5883 (13)	0.0638 (13)	0.038 (4)*
H61B	−0.0431 (17)	0.5330 (12)	0.1488 (11)	0.027 (3)*
C62	−0.05395 (13)	0.69164 (9)	0.22197 (9)	0.0310 (2)
H62A	−0.059 (2)	0.7574 (15)	0.1989 (14)	0.049 (5)*
H62B	−0.164 (2)	0.6604 (14)	0.2299 (13)	0.039 (4)*
C63	0.08227 (13)	0.73000 (9)	0.32478 (8)	0.02806 (19)
H63A	0.075 (2)	0.6703 (14)	0.3558 (13)	0.039 (4)*
H63B	0.0736 (19)	0.7914 (13)	0.3791 (13)	0.038 (4)*
C64	0.25074 (11)	0.76573 (7)	0.30339 (7)	0.02088 (15)
H64A	0.3370 (17)	0.7863 (11)	0.3681 (11)	0.025 (3)*
H64B	0.2700 (17)	0.8337 (12)	0.2788 (11)	0.030 (3)*

	U11	U22	U33	U12	U13	U23
O1	0.0141 (2)	0.0241 (3)	0.0131 (2)	0.0092 (2)	0.00717 (19)	0.0080 (2)
N1	0.0118 (2)	0.0199 (3)	0.0118 (2)	0.0077 (2)	0.0050 (2)	0.0080 (2)
N2	0.0124 (3)	0.0189 (3)	0.0118 (3)	0.0044 (2)	0.0018 (2)	0.0046 (2)
N3	0.0167 (3)	0.0181 (3)	0.0123 (3)	0.0043 (2)	0.0021 (2)	0.0034 (2)
N4	0.0179 (3)	0.0152 (3)	0.0108 (2)	0.0049 (2)	0.0028 (2)	0.0023 (2)
N5	0.0120 (2)	0.0138 (2)	0.0102 (2)	0.0050 (2)	0.00305 (19)	0.00371 (19)
N6	0.0132 (3)	0.0130 (2)	0.0109 (2)	0.0040 (2)	0.0037 (2)	0.00355 (19)
C1	0.0102 (3)	0.0149 (3)	0.0102 (3)	0.0048 (2)	0.0032 (2)	0.0038 (2)
C2	0.0109 (3)	0.0146 (3)	0.0103 (3)	0.0054 (2)	0.0035 (2)	0.0042 (2)
C3	0.0108 (3)	0.0142 (3)	0.0107 (3)	0.0047 (2)	0.0035 (2)	0.0050 (2)
C4	0.0105 (3)	0.0147 (3)	0.0127 (3)	0.0056 (2)	0.0041 (2)	0.0053 (2)
C5	0.0159 (3)	0.0203 (3)	0.0176 (3)	0.0096 (3)	0.0090 (3)	0.0084 (3)
C6	0.0142 (3)	0.0241 (4)	0.0242 (4)	0.0101 (3)	0.0104 (3)	0.0109 (3)
C7	0.0113 (3)	0.0238 (4)	0.0247 (4)	0.0079 (3)	0.0053 (3)	0.0099 (3)
C8	0.0114 (3)	0.0208 (3)	0.0168 (3)	0.0065 (2)	0.0026 (2)	0.0070 (3)
C9	0.0103 (3)	0.0150 (3)	0.0134 (3)	0.0055 (2)	0.0044 (2)	0.0059 (2)
C10	0.0185 (3)	0.0160 (3)	0.0159 (3)	0.0063 (3)	0.0051 (3)	0.0076 (2)
C11	0.0251 (4)	0.0194 (3)	0.0221 (4)	0.0027 (3)	0.0097 (3)	0.0090 (3)
C12	0.0297 (5)	0.0174 (3)	0.0284 (4)	−0.0010 (3)	0.0088 (4)	0.0050 (3)
C13	0.0205 (4)	0.0219 (4)	0.0203 (4)	−0.0014 (3)	0.0043 (3)	0.0015 (3)
C14	0.0177 (3)	0.0176 (3)	0.0132 (3)	0.0027 (3)	0.0049 (3)	0.0010 (2)
O51	0.0383 (4)	0.0196 (3)	0.0197 (3)	0.0109 (3)	0.0165 (3)	0.0097 (2)
N51	0.0272 (3)	0.0141 (3)	0.0140 (3)	0.0077 (2)	0.0090 (3)	0.0054 (2)
N52	0.0236 (3)	0.0198 (3)	0.0173 (3)	0.0063 (3)	0.0042 (3)	0.0032 (2)
N53	0.0253 (4)	0.0247 (3)	0.0186 (3)	0.0083 (3)	0.0019 (3)	0.0044 (3)
N54	0.0247 (4)	0.0246 (3)	0.0143 (3)	0.0102 (3)	0.0018 (3)	0.0056 (2)
N55	0.0202 (3)	0.0180 (3)	0.0126 (3)	0.0074 (2)	0.0042 (2)	0.0055 (2)
N56	0.0200 (3)	0.0147 (3)	0.0128 (3)	0.0066 (2)	0.0037 (2)	0.0033 (2)
C51	0.0245 (4)	0.0157 (3)	0.0137 (3)	0.0078 (3)	0.0070 (3)	0.0059 (2)
C52	0.0221 (3)	0.0142 (3)	0.0135 (3)	0.0063 (3)	0.0059 (3)	0.0049 (2)
C53	0.0206 (3)	0.0162 (3)	0.0143 (3)	0.0070 (3)	0.0060 (3)	0.0044 (2)
C54	0.0192 (3)	0.0163 (3)	0.0150 (3)	0.0075 (3)	0.0059 (3)	0.0068 (2)
C55	0.0243 (4)	0.0234 (4)	0.0189 (3)	0.0120 (3)	0.0102 (3)	0.0119 (3)
C56	0.0226 (4)	0.0242 (4)	0.0269 (4)	0.0099 (3)	0.0119 (3)	0.0159 (3)
C57	0.0207 (4)	0.0194 (3)	0.0278 (4)	0.0057 (3)	0.0071 (3)	0.0111 (3)
C58	0.0222 (4)	0.0165 (3)	0.0190 (3)	0.0057 (3)	0.0042 (3)	0.0065 (3)
C59	0.0202 (3)	0.0158 (3)	0.0150 (3)	0.0078 (3)	0.0065 (3)	0.0071 (2)
C60	0.0260 (4)	0.0214 (4)	0.0149 (3)	0.0088 (3)	0.0022 (3)	0.0060 (3)
C61	0.0238 (4)	0.0219 (4)	0.0229 (4)	0.0070 (3)	0.0005 (3)	0.0041 (3)
C62	0.0237 (4)	0.0301 (5)	0.0333 (5)	0.0114 (4)	0.0046 (4)	0.0010 (4)
C63	0.0242 (4)	0.0281 (4)	0.0259 (4)	0.0074 (3)	0.0098 (3)	−0.0006 (3)
C64	0.0229 (4)	0.0161 (3)	0.0193 (4)	0.0058 (3)	0.0058 (3)	−0.0001 (3)

O1—C1	1.2329 (9)	O51—C51	1.2317 (10)
N1—H1N	0.850 (14)	N51—H51N	0.886 (16)
N1—C1	1.3578 (9)	N51—C51	1.3589 (10)
N1—C9	1.4142 (10)	N51—C59	1.4131 (11)
N2—N3	1.3686 (10)	N52—N53	1.3663 (11)
N2—C3	1.3229 (9)	N52—C53	1.3202 (11)
N3—N4	1.2983 (10)	N53—N54	1.2992 (12)
N4—N5	1.3640 (9)	N54—N55	1.3615 (10)
N5—C3	1.3499 (9)	N55—C53	1.3524 (11)
N5—C4	1.4225 (9)	N55—C54	1.4244 (11)
N6—C2	1.4605 (10)	N56—C52	1.4632 (11)
N6—C10	1.4752 (10)	N56—C60	1.4731 (11)
N6—C14	1.4674 (10)	N56—C64	1.4748 (11)
C1—C2	1.5351 (10)	C51—C52	1.5338 (11)
C2—H2	0.982 (12)	C52—H52	1.026 (13)
C2—C3	1.4944 (10)	C52—C53	1.4955 (11)
C4—C5	1.3923 (10)	C54—C55	1.3908 (11)
C4—C9	1.4004 (10)	C54—C59	1.4005 (11)
C5—H5	1.002 (14)	C55—H55	0.974 (13)
C5—C6	1.3897 (11)	C55—C56	1.3904 (13)
C6—H6	0.936 (15)	C56—H56	0.951 (14)
C6—C7	1.3959 (13)	C56—C57	1.3943 (14)
C7—H7	0.947 (15)	C57—H57	0.992 (14)
C7—C8	1.3877 (12)	C57—C58	1.3912 (13)
C8—H8	1.007 (13)	C58—H58	0.983 (14)
C8—C9	1.3988 (10)	C58—C59	1.3982 (12)
C10—H10A	1.014 (13)	C60—H60	0.982 (13)
C10—H10B	1.001 (14)	C60—H60B	0.997 (14)
C10—C11	1.5196 (12)	C60—C61	1.5258 (14)
C11—H11A	0.969 (15)	C61—H61A	0.991 (16)
C11—H11	0.996 (16)	C61—H61B	1.016 (14)
C11—C12	1.5275 (14)	C61—C62	1.5269 (14)
C12—H12A	0.996 (16)	C62—H62A	1.005 (18)
C12—H12B	1.023 (16)	C62—H62B	0.974 (17)
C12—C13	1.5300 (15)	C62—C63	1.5300 (16)
C13—H13A	0.998 (15)	C63—H63A	0.977 (16)
C13—H13B	0.979 (14)	C63—H63B	0.965 (16)
C13—C14	1.5252 (12)	C63—C64	1.5252 (14)
C14—H14A	0.998 (14)	C64—H64A	0.973 (14)
C14—H14B	0.982 (14)	C64—H64B	1.015 (14)
H1N—N1—C1	114.3 (9)	H51N—N51—C51	115.8 (10)
H1N—N1—C9	115.7 (9)	H51N—N51—C59	114.1 (10)
C1—N1—C9	129.81 (6)	C51—N51—C59	130.00 (7)
N3—N2—C3	105.55 (6)	N53—N52—C53	105.52 (7)
N2—N3—N4	111.36 (6)	N52—N53—N54	111.29 (7)
N3—N4—N5	106.08 (6)	N53—N54—N55	106.29 (7)
N4—N5—C3	108.10 (6)	N54—N55—C53	107.76 (7)
N4—N5—C4	122.45 (6)	N54—N55—C54	122.40 (7)
C3—N5—C4	129.44 (6)	C53—N55—C54	129.82 (7)
C2—N6—C10	111.02 (6)	C52—N56—C60	113.57 (7)
C2—N6—C14	112.06 (6)	C52—N56—C64	110.57 (6)
C10—N6—C14	109.94 (6)	C60—N56—C64	109.24 (7)
O1—C1—N1	121.56 (7)	O51—C51—N51	121.40 (7)
O1—C1—C2	120.43 (6)	O51—C51—C52	119.90 (7)
N1—C1—C2	118.00 (6)	N51—C51—C52	118.64 (7)
N6—C2—C1	111.27 (6)	N56—C52—C51	113.38 (7)
N6—C2—H2	113.6 (7)	N56—C52—H52	113.6 (7)
N6—C2—C3	109.40 (6)	N56—C52—C53	108.84 (7)
C1—C2—H2	108.1 (7)	C51—C52—H52	105.9 (7)
C1—C2—C3	107.10 (6)	C51—C52—C53	105.63 (6)
H2—C2—C3	107.0 (7)	H52—C52—C53	109.1 (7)
N2—C3—N5	108.91 (6)	N52—C53—N55	109.13 (7)
N2—C3—C2	128.45 (7)	N52—C53—C52	128.94 (8)
N5—C3—C2	122.63 (6)	N55—C53—C52	121.92 (7)
N5—C4—C5	118.89 (7)	N55—C54—C55	119.38 (7)
N5—C4—C9	119.78 (6)	N55—C54—C59	119.52 (7)
C5—C4—C9	121.33 (7)	C55—C54—C59	121.06 (8)
C4—C5—H5	119.5 (8)	C54—C55—H55	120.3 (8)
C4—C5—C6	119.48 (7)	C54—C55—C56	119.71 (8)
H5—C5—C6	121.0 (8)	H55—C55—C56	119.9 (8)
C5—C6—H6	121.3 (9)	C55—C56—H56	120.7 (9)
C5—C6—C7	119.99 (7)	C55—C56—C57	119.95 (8)
H6—C6—C7	118.7 (9)	H56—C56—C57	119.3 (9)
C6—C7—H7	120.5 (9)	C56—C57—H57	122.7 (8)
C6—C7—C8	120.13 (7)	C56—C57—C58	120.12 (8)
H7—C7—C8	119.4 (9)	H57—C57—C58	117.2 (8)
C7—C8—H8	121.2 (8)	C57—C58—H58	119.8 (8)
C7—C8—C9	120.79 (7)	C57—C58—C59	120.60 (8)
H8—C8—C9	118.0 (8)	H58—C58—C59	119.6 (8)
N1—C9—C4	123.90 (6)	N51—C59—C54	123.27 (7)
N1—C9—C8	117.64 (7)	N51—C59—C58	117.95 (7)
C4—C9—C8	118.27 (7)	C54—C59—C58	118.55 (7)
N6—C10—H10A	109.2 (7)	N56—C60—H60	109.4 (8)
N6—C10—H10B	109.5 (8)	N56—C60—H60B	108.1 (8)
N6—C10—C11	109.81 (7)	N56—C60—C61	108.76 (7)
H10A—C10—H10B	105.0 (11)	H60—C60—H60B	111.6 (11)
H10A—C10—C11	111.8 (8)	H60—C60—C61	109.8 (8)
H10B—C10—C11	111.4 (8)	H60B—C60—C61	109.2 (8)
C10—C11—H11A	108.7 (9)	C60—C61—H61A	108.9 (9)
C10—C11—H11	108.8 (9)	C60—C61—H61B	109.5 (8)
C10—C11—C12	110.94 (8)	C60—C61—C62	111.39 (8)
H11A—C11—H11	107.3 (13)	H61A—C61—H61B	107.4 (12)
H11A—C11—C12	111.0 (9)	H61A—C61—C62	110.2 (9)
H11—C11—C12	109.9 (9)	H61B—C61—C62	109.4 (8)
C11—C12—H12A	110.7 (9)	C61—C62—H62A	109.2 (10)
C11—C12—H12B	110.5 (9)	C61—C62—H62B	109.1 (9)
C11—C12—C13	110.97 (8)	C61—C62—C63	110.61 (8)
H12A—C12—H12B	105.6 (13)	H62A—C62—H62B	102.9 (13)
H12A—C12—C13	108.5 (9)	H62A—C62—C63	110.7 (10)
H12B—C12—C13	110.4 (9)	H62B—C62—C63	114.0 (9)
C12—C13—H13A	110.2 (9)	C62—C63—H63A	111.7 (10)
C12—C13—H13B	110.7 (8)	C62—C63—H63B	111.2 (9)
C12—C13—C14	111.35 (8)	C62—C63—C64	110.88 (9)
H13A—C13—H13B	110.0 (12)	H63A—C63—H63B	105.8 (13)
H13A—C13—C14	106.0 (8)	H63A—C63—C64	107.8 (9)
H13B—C13—C14	108.4 (8)	H63B—C63—C64	109.4 (9)
N6—C14—C13	109.53 (7)	N56—C64—C63	110.32 (7)
N6—C14—H14A	107.6 (8)	N56—C64—H64A	108.6 (8)
N6—C14—H14B	109.8 (8)	N56—C64—H64B	108.5 (8)
C13—C14—H14A	109.5 (8)	C63—C64—H64A	110.7 (8)
C13—C14—H14B	109.4 (8)	C63—C64—H64B	111.4 (8)
H14A—C14—H14B	111.0 (12)	H64A—C64—H64B	107.2 (12)
C3—N2—N3—N4	0.15 (9)	C53—N52—N53—N54	0.19 (10)
N2—N3—N4—N5	0.29 (8)	N52—N53—N54—N55	0.05 (10)
N3—N4—N5—C3	−0.62 (8)	N53—N54—N55—C53	−0.27 (9)
N3—N4—N5—C4	−179.48 (7)	N53—N54—N55—C54	177.97 (8)
C9—N1—C1—O1	179.78 (7)	C59—N51—C51—O51	178.22 (9)
C9—N1—C1—C2	1.11 (11)	C59—N51—C51—C52	0.99 (14)
C10—N6—C2—C1	−178.53 (6)	C60—N56—C52—C51	−50.44 (9)
C10—N6—C2—C3	63.32 (7)	C60—N56—C52—C53	−167.67 (6)
C14—N6—C2—C1	−55.17 (8)	C64—N56—C52—C51	−173.65 (7)
C14—N6—C2—C3	−173.31 (6)	C64—N56—C52—C53	69.12 (8)
O1—C1—C2—N6	123.80 (7)	O51—C51—C52—N56	126.51 (9)
O1—C1—C2—C3	−116.68 (7)	O51—C51—C52—C53	−114.40 (9)
N1—C1—C2—N6	−57.52 (8)	N51—C51—C52—N56	−56.22 (10)
N1—C1—C2—C3	62.01 (8)	N51—C51—C52—C53	62.87 (10)
N3—N2—C3—N5	−0.53 (8)	N53—N52—C53—N55	−0.36 (9)
N3—N2—C3—C2	178.55 (7)	N53—N52—C53—C52	−179.19 (8)
N4—N5—C3—N2	0.73 (8)	N54—N55—C53—N52	0.40 (9)
N4—N5—C3—C2	−178.43 (6)	N54—N55—C53—C52	179.32 (7)
C4—N5—C3—N2	179.49 (7)	C54—N55—C53—N52	−177.66 (8)
C4—N5—C3—C2	0.33 (12)	C54—N55—C53—C52	1.26 (13)
N6—C2—C3—N2	−121.66 (8)	N56—C52—C53—N52	−124.11 (9)
N6—C2—C3—N5	57.31 (9)	N56—C52—C53—N55	57.19 (10)
C1—C2—C3—N2	117.62 (8)	C51—C52—C53—N52	113.82 (9)
C1—C2—C3—N5	−63.41 (9)	C51—C52—C53—N55	−64.87 (10)
N4—N5—C4—C5	33.23 (10)	N54—N55—C54—C55	36.85 (11)
N4—N5—C4—C9	−146.46 (7)	N54—N55—C54—C59	−140.99 (8)
C3—N5—C4—C5	−145.37 (8)	C53—N55—C54—C55	−145.34 (9)
C3—N5—C4—C9	34.94 (11)	C53—N55—C54—C59	36.82 (12)
N5—C4—C5—C6	179.98 (7)	N55—C54—C55—C56	−177.01 (8)
C9—C4—C5—C6	−0.34 (12)	C59—C54—C55—C56	0.80 (13)
C4—C5—C6—C7	−0.64 (12)	C54—C55—C56—C57	−0.99 (13)
C5—C6—C7—C8	0.98 (13)	C55—C56—C57—C58	0.65 (14)
C6—C7—C8—C9	−0.34 (13)	C56—C57—C58—C59	−0.11 (14)
C7—C8—C9—N1	174.59 (7)	C57—C58—C59—N51	174.60 (8)
C7—C8—C9—C4	−0.62 (11)	C57—C58—C59—C54	−0.09 (13)
N5—C4—C9—N1	5.76 (11)	N55—C54—C59—N51	3.16 (12)
N5—C4—C9—C8	−179.36 (7)	N55—C54—C59—C58	177.55 (7)
C5—C4—C9—N1	−173.92 (7)	C55—C54—C59—N51	−174.65 (8)
C5—C4—C9—C8	0.96 (11)	C55—C54—C59—C58	−0.26 (12)
C1—N1—C9—C4	−43.24 (12)	C51—N51—C59—C54	−41.97 (13)
C1—N1—C9—C8	141.84 (8)	C51—N51—C59—C58	143.61 (9)
C2—N6—C10—C11	−171.45 (6)	C52—N56—C60—C61	171.56 (7)
C14—N6—C10—C11	63.98 (8)	C64—N56—C60—C61	−64.50 (9)
N6—C10—C11—C12	−57.34 (10)	N56—C60—C61—C62	58.95 (10)
C10—C11—C12—C13	50.96 (11)	C60—C61—C62—C63	−52.02 (12)
C11—C12—C13—C14	−50.81 (11)	C61—C62—C63—C64	50.42 (12)
C2—N6—C14—C13	172.62 (7)	C52—N56—C64—C63	−170.26 (8)
C10—N6—C14—C13	−63.41 (9)	C60—N56—C64—C63	64.06 (10)
C12—C13—C14—N6	56.84 (10)	C62—C63—C64—N56	−56.70 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.850 (14)	2.069 (14)	2.9089 (9)	169.4 (13)
N51—H51N···O51ii	0.886 (16)	1.929 (16)	2.8116 (10)	173.6 (14)
C6—H6···N2iii	0.936 (15)	2.531 (15)	3.4638 (11)	174.8 (12)
C7—H7···O1iii	0.947 (15)	2.406 (15)	3.3394 (10)	168.4 (13)
C55—H55···N54iv	0.974 (13)	2.548 (13)	3.2293 (11)	127.0 (10)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.850 (14)	2.069 (14)	2.9089 (9)	169.4 (13)
N51—H51N⋯O51ii	0.886 (16)	1.929 (16)	2.8116 (10)	173.6 (14)
C6—H6⋯N2iii	0.936 (15)	2.531 (15)	3.4638 (11)	174.8 (12)
C7—H7⋯O1iii	0.947 (15)	2.406 (15)	3.3394 (10)	168.4 (13)
C55—H55⋯N54iv	0.974 (13)	2.548 (13)	3.2293 (11)	127.0 (10)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .