N,N'-[2,2'-(Phenyl-aza-nedi-yl)bis-(ethane-2,1-di-yl)]dipicolinamide.

The asymmetric unit of the title compound, C22H23N5O2, contains two independent mol-ecules with similar conformations; the terminal pyridine rings are oriented at dihedral angles of 23.99 (8) and 18.07 (8)° with respect to the central benzene ring in one mol-ecule and 28.99 (8) and 23.22 (8)° in the other. In the crystal, N-H⋯O and weak C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional supra-molecular structure. Weak inter-molecular C-H⋯π inter-actions are also observed in the crystal.

Related literature

For background to bis­(pyridine­carboxamide) derivatives, see: Cornman et al. (1999 ▶); Song et al. (2010 ▶); Singh et al. (2008 ▶). For the synthesis, see: Jain et al. (2004 ▶); Lee et al. (2006 ▶); Barnes et al. (1978 ▶). For related structures, see: Adolph et al. (2012 ▶); Munro & Wilson (2010 ▶); Yan et al. (2012 ▶).

Experimental

Crystal data

C22H23N5O2

M = 389.45

Monoclinic,

a = 8.64349 (7) Å

b = 24.8210 (3) Å

c = 18.40861 (18) Å

β = 90.5648 (8)°

V = 3949.20 (7) Å3

Z = 8

Cu Kα radiation

μ = 0.70 mm−1

T = 100 K

0.12 × 0.08 × 0.07 mm

Data collection

Agilent Xcalibur Atlas Gemini ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.886, T max = 0.950

28468 measured reflections

7050 independent reflections

6128 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.097

S = 1.14

7050 reflections

523 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813008696/xu5691sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008696/xu5691Isup2.hkl

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

C22H23N5O2	F(000) = 1648
Mr = 389.45	Dx = 1.310 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2yn	Cell parameters from 13020 reflections
a = 8.64349 (7) Å	θ = 3.0–67.1°
b = 24.8210 (3) Å	µ = 0.70 mm−1
c = 18.40861 (18) Å	T = 100 K
β = 90.5648 (8)°	Block, colorless
V = 3949.20 (7) Å3	0.12 × 0.08 × 0.07 mm
Z = 8

Agilent Xcalibur Atlas Gemini ultra diffractometer	7050 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	6128 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.038
Detector resolution: 10.5095 pixels mm-1	θmax = 67.2°, θmin = 3.0°
ω scans	h = −8→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −29→29
Tmin = 0.886, Tmax = 0.950	l = −21→21
28468 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0328P)2 + 1.7734P] where P = (Fo2 + 2Fc2)/3
7050 reflections	(Δ/σ)max < 0.001
523 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.26 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
O3	0.01667 (13)	0.20717 (5)	0.70802 (6)	0.0213 (3)
O4	0.42663 (14)	0.41541 (5)	0.43618 (7)	0.0262 (3)
N10	0.72634 (16)	0.38111 (6)	0.56121 (7)	0.0211 (3)
N8	0.05731 (16)	0.30231 (6)	0.48259 (8)	0.0210 (3)
N6	−0.24832 (18)	0.10919 (6)	0.64032 (8)	0.0253 (3)
N9	0.47932 (15)	0.33680 (6)	0.49331 (7)	0.0194 (3)
H9	0.5429	0.3194	0.5208	0.023*
C40	0.64956 (18)	0.41244 (7)	0.51379 (8)	0.0189 (3)
N7	−0.14356 (16)	0.20756 (6)	0.60938 (7)	0.0211 (3)
H7	−0.2159	0.1904	0.5868	0.025*
C39	0.50887 (18)	0.38841 (7)	0.47694 (9)	0.0195 (3)
C28	−0.08427 (18)	0.18567 (7)	0.66985 (8)	0.0172 (3)
C27	−0.15311 (18)	0.13184 (7)	0.68976 (8)	0.0178 (3)
C36	−0.02993 (18)	0.32728 (7)	0.42846 (8)	0.0177 (3)
C41	0.6897 (2)	0.46544 (8)	0.49946 (10)	0.0251 (4)
H41	0.6331	0.4858	0.4661	0.030*
C32	−0.26386 (18)	0.33195 (7)	0.35478 (9)	0.0195 (3)
H32	−0.3619	0.3187	0.3437	0.023*
C37	0.19986 (18)	0.32603 (7)	0.50953 (9)	0.0194 (3)
H37A	0.2156	0.3153	0.5597	0.023*
H37B	0.1901	0.3650	0.5085	0.023*
C23	−0.3065 (2)	0.06086 (8)	0.65665 (10)	0.0282 (4)
H23	−0.3722	0.0445	0.6230	0.034*
C26	−0.11910 (18)	0.10871 (7)	0.75624 (9)	0.0187 (3)
H26	−0.0554	0.1263	0.7896	0.022*
C31	−0.17940 (18)	0.30923 (7)	0.41132 (8)	0.0175 (3)
H31	−0.2227	0.2815	0.4384	0.021*
C24	−0.2747 (2)	0.03374 (7)	0.72098 (10)	0.0256 (4)
H24	−0.3149	−0.0004	0.7293	0.031*
C30	0.01142 (18)	0.25116 (7)	0.51395 (9)	0.0186 (3)
H30A	0.1032	0.2313	0.5285	0.022*
H30B	−0.0431	0.2301	0.4775	0.022*
C33	−0.20453 (19)	0.37409 (8)	0.31463 (9)	0.0238 (4)
H33	−0.2608	0.3889	0.2762	0.029*
C34	−0.0595 (2)	0.39369 (8)	0.33289 (10)	0.0262 (4)
H34	−0.0198	0.4228	0.3073	0.031*
C43	0.8975 (2)	0.45549 (8)	0.58395 (10)	0.0259 (4)
H43	0.9832	0.4691	0.6088	0.031*
C44	0.8496 (2)	0.40288 (7)	0.59447 (9)	0.0241 (4)
H44	0.9063	0.3814	0.6265	0.029*
C29	−0.0926 (2)	0.25855 (7)	0.57982 (9)	0.0210 (4)
H29A	−0.0365	0.2783	0.6171	0.025*
H29B	−0.1823	0.2797	0.5658	0.025*
C42	0.8154 (2)	0.48745 (8)	0.53567 (10)	0.0272 (4)
H42	0.8442	0.5230	0.5277	0.033*
C38	0.34208 (19)	0.30960 (7)	0.46552 (9)	0.0211 (4)
H38A	0.3565	0.2709	0.4686	0.025*
H38B	0.3260	0.3190	0.4149	0.025*
C35	0.02825 (19)	0.37092 (7)	0.38850 (9)	0.0218 (4)
H35	0.1259	0.3846	0.3994	0.026*
C25	−0.18174 (19)	0.05870 (7)	0.77240 (9)	0.0218 (4)
H25	−0.1616	0.0423	0.8169	0.026*
O1	0.51720 (13)	0.20741 (5)	0.55318 (6)	0.0224 (3)
O2	0.92905 (13)	0.41536 (5)	0.82007 (6)	0.0233 (3)
N5	1.22283 (16)	0.37938 (6)	0.69577 (7)	0.0204 (3)
N3	0.55536 (15)	0.30360 (6)	0.77265 (7)	0.0206 (3)
N2	0.35218 (16)	0.20593 (6)	0.64857 (7)	0.0210 (3)
H2	0.2804	0.1881	0.6699	0.025*
N4	0.97851 (15)	0.33578 (6)	0.76493 (7)	0.0183 (3)
H4	1.0416	0.3178	0.7385	0.022*
N1	0.24906 (17)	0.10774 (6)	0.61151 (8)	0.0251 (3)
C5	0.35355 (18)	0.13041 (7)	0.56756 (9)	0.0183 (3)
C6	0.41614 (18)	0.18486 (7)	0.58916 (8)	0.0175 (3)
C17	1.00987 (18)	0.38738 (7)	0.78022 (8)	0.0179 (3)
C18	1.15194 (18)	0.41036 (7)	0.74477 (9)	0.0179 (3)
C9	0.47424 (18)	0.32890 (7)	0.82781 (8)	0.0174 (3)
C11	0.24738 (19)	0.33473 (7)	0.90377 (9)	0.0201 (3)
H11	0.1500	0.3219	0.9160	0.024*
C22	1.3487 (2)	0.39964 (7)	0.66449 (9)	0.0225 (4)
H22	1.4002	0.3784	0.6308	0.027*
C21	1.4069 (2)	0.45028 (8)	0.67933 (10)	0.0259 (4)
H21	1.4951	0.4628	0.6562	0.031*
C14	0.53710 (19)	0.37270 (7)	0.86626 (9)	0.0223 (4)
H14	0.6336	0.3863	0.8538	0.027*
C15	0.69885 (18)	0.32599 (7)	0.74607 (9)	0.0190 (3)
H15A	0.6910	0.3650	0.7458	0.023*
H15B	0.7138	0.3142	0.6964	0.023*
C8	0.50815 (18)	0.25151 (7)	0.74369 (9)	0.0188 (3)
H8A	0.4570	0.2311	0.7814	0.023*
H8B	0.5992	0.2316	0.7291	0.023*
C13	0.4555 (2)	0.39580 (8)	0.92285 (10)	0.0258 (4)
H13	0.4988	0.4247	0.9480	0.031*
C10	0.32600 (18)	0.31133 (7)	0.84680 (8)	0.0176 (3)
H10	0.2797	0.2835	0.8207	0.021*
C12	0.3113 (2)	0.37699 (7)	0.94294 (9)	0.0241 (4)
H12	0.2588	0.3923	0.9817	0.029*
C7	0.39857 (19)	0.25749 (7)	0.67850 (9)	0.0208 (3)
H7A	0.3071	0.2771	0.6933	0.025*
H7B	0.4493	0.2784	0.6411	0.025*
C16	0.84045 (19)	0.30946 (7)	0.79192 (9)	0.0198 (3)
H16A	0.8245	0.3195	0.8422	0.024*
H16B	0.8536	0.2707	0.7898	0.024*
C1	0.1974 (2)	0.05894 (8)	0.59321 (10)	0.0290 (4)
H1	0.1244	0.0427	0.6229	0.035*
C4	0.40508 (19)	0.10617 (7)	0.50462 (9)	0.0219 (4)
H4A	0.4750	0.1237	0.4747	0.026*
C3	0.3509 (2)	0.05546 (8)	0.48688 (10)	0.0269 (4)
H3	0.3842	0.0381	0.4451	0.032*
C19	1.2014 (2)	0.46160 (8)	0.76317 (10)	0.0272 (4)
H19	1.1488	0.4819	0.7975	0.033*
C20	1.3310 (2)	0.48193 (8)	0.72935 (11)	0.0310 (4)
H20	1.3666	0.5164	0.7401	0.037*
C2	0.2463 (2)	0.03102 (7)	0.53257 (10)	0.0285 (4)
H2A	0.2095	−0.0035	0.5228	0.034*

	U11	U22	U33	U12	U13	U23
O3	0.0171 (6)	0.0243 (6)	0.0225 (6)	−0.0026 (5)	−0.0031 (5)	−0.0003 (5)
O4	0.0194 (6)	0.0311 (7)	0.0280 (6)	0.0025 (5)	−0.0047 (5)	0.0053 (5)
N10	0.0197 (7)	0.0244 (8)	0.0191 (7)	−0.0006 (6)	−0.0016 (5)	−0.0002 (6)
N8	0.0154 (7)	0.0250 (8)	0.0226 (7)	−0.0057 (6)	−0.0056 (5)	0.0064 (6)
N6	0.0304 (8)	0.0253 (8)	0.0200 (7)	−0.0056 (6)	−0.0018 (6)	−0.0029 (6)
N9	0.0112 (7)	0.0268 (8)	0.0203 (7)	0.0014 (5)	−0.0017 (5)	0.0021 (6)
C40	0.0159 (8)	0.0244 (9)	0.0164 (8)	0.0026 (7)	0.0040 (6)	0.0003 (7)
N7	0.0205 (7)	0.0231 (8)	0.0196 (7)	−0.0061 (6)	−0.0039 (5)	0.0019 (6)
C39	0.0156 (8)	0.0264 (9)	0.0166 (8)	0.0031 (7)	0.0022 (6)	−0.0003 (7)
C28	0.0147 (8)	0.0208 (8)	0.0163 (8)	0.0016 (6)	0.0031 (6)	−0.0018 (6)
C27	0.0156 (8)	0.0195 (9)	0.0184 (8)	0.0007 (6)	0.0020 (6)	−0.0029 (6)
C36	0.0148 (8)	0.0224 (9)	0.0157 (8)	0.0014 (6)	0.0001 (6)	−0.0013 (6)
C41	0.0189 (9)	0.0280 (10)	0.0284 (9)	0.0027 (7)	0.0011 (7)	0.0054 (7)
C32	0.0130 (8)	0.0256 (9)	0.0198 (8)	0.0029 (6)	−0.0012 (6)	−0.0037 (7)
C37	0.0155 (8)	0.0240 (9)	0.0187 (8)	−0.0035 (6)	−0.0024 (6)	0.0016 (7)
C23	0.0348 (10)	0.0245 (10)	0.0253 (9)	−0.0089 (8)	−0.0011 (8)	−0.0053 (7)
C26	0.0134 (8)	0.0222 (9)	0.0205 (8)	0.0020 (6)	0.0013 (6)	−0.0013 (7)
C31	0.0155 (8)	0.0202 (8)	0.0170 (8)	0.0003 (6)	0.0023 (6)	−0.0020 (6)
C24	0.0270 (9)	0.0190 (9)	0.0310 (10)	−0.0018 (7)	0.0059 (7)	−0.0005 (7)
C30	0.0149 (8)	0.0206 (9)	0.0201 (8)	−0.0001 (6)	−0.0036 (6)	0.0021 (7)
C33	0.0189 (9)	0.0315 (10)	0.0209 (8)	0.0065 (7)	−0.0015 (7)	0.0043 (7)
C34	0.0233 (9)	0.0285 (10)	0.0269 (9)	0.0007 (7)	0.0022 (7)	0.0093 (8)
C43	0.0217 (9)	0.0307 (10)	0.0254 (9)	−0.0055 (7)	−0.0003 (7)	−0.0031 (8)
C44	0.0219 (9)	0.0292 (10)	0.0209 (8)	−0.0017 (7)	−0.0047 (7)	0.0017 (7)
C29	0.0244 (9)	0.0206 (9)	0.0181 (8)	−0.0013 (7)	−0.0006 (7)	0.0012 (7)
C42	0.0222 (9)	0.0243 (10)	0.0353 (10)	−0.0037 (7)	0.0042 (7)	0.0014 (8)
C38	0.0188 (8)	0.0254 (9)	0.0191 (8)	−0.0002 (7)	−0.0018 (6)	−0.0010 (7)
C35	0.0145 (8)	0.0266 (9)	0.0243 (9)	−0.0023 (7)	0.0000 (6)	0.0028 (7)
C25	0.0198 (8)	0.0220 (9)	0.0238 (9)	0.0040 (7)	0.0029 (7)	0.0037 (7)
O1	0.0169 (6)	0.0250 (6)	0.0253 (6)	−0.0022 (5)	0.0045 (5)	−0.0001 (5)
O2	0.0182 (6)	0.0255 (7)	0.0262 (6)	0.0028 (5)	0.0042 (5)	−0.0038 (5)
N5	0.0199 (7)	0.0221 (8)	0.0192 (7)	−0.0011 (6)	0.0012 (5)	−0.0008 (6)
N3	0.0152 (7)	0.0252 (8)	0.0214 (7)	−0.0044 (6)	0.0057 (5)	−0.0062 (6)
N2	0.0204 (7)	0.0239 (8)	0.0187 (7)	−0.0054 (6)	0.0038 (5)	−0.0026 (6)
N4	0.0126 (6)	0.0212 (7)	0.0211 (7)	0.0018 (5)	0.0015 (5)	−0.0030 (6)
N1	0.0278 (8)	0.0275 (8)	0.0199 (7)	−0.0065 (6)	0.0022 (6)	0.0007 (6)
C5	0.0146 (8)	0.0220 (9)	0.0183 (8)	0.0008 (6)	−0.0011 (6)	0.0026 (7)
C6	0.0131 (8)	0.0218 (9)	0.0177 (8)	0.0015 (6)	−0.0027 (6)	0.0004 (6)
C17	0.0146 (8)	0.0226 (9)	0.0165 (8)	0.0032 (6)	−0.0032 (6)	0.0004 (7)
C18	0.0159 (8)	0.0210 (9)	0.0168 (8)	0.0026 (6)	−0.0033 (6)	0.0010 (6)
C9	0.0145 (8)	0.0207 (9)	0.0172 (8)	0.0026 (6)	0.0003 (6)	0.0015 (6)
C11	0.0156 (8)	0.0251 (9)	0.0197 (8)	0.0050 (7)	0.0016 (6)	0.0042 (7)
C22	0.0214 (9)	0.0273 (9)	0.0188 (8)	−0.0027 (7)	0.0035 (6)	−0.0019 (7)
C21	0.0233 (9)	0.0286 (10)	0.0260 (9)	−0.0062 (7)	0.0043 (7)	0.0012 (7)
C14	0.0160 (8)	0.0250 (9)	0.0257 (9)	−0.0005 (7)	0.0009 (7)	−0.0039 (7)
C15	0.0146 (8)	0.0240 (9)	0.0185 (8)	−0.0029 (6)	0.0033 (6)	−0.0022 (7)
C8	0.0161 (8)	0.0215 (9)	0.0190 (8)	0.0001 (6)	0.0037 (6)	−0.0029 (7)
C13	0.0199 (9)	0.0261 (10)	0.0312 (10)	0.0028 (7)	−0.0015 (7)	−0.0093 (8)
C10	0.0164 (8)	0.0198 (8)	0.0166 (8)	0.0007 (6)	−0.0013 (6)	0.0021 (6)
C12	0.0231 (9)	0.0275 (9)	0.0216 (8)	0.0081 (7)	0.0021 (7)	−0.0040 (7)
C7	0.0203 (8)	0.0216 (9)	0.0205 (8)	−0.0005 (7)	0.0011 (6)	−0.0017 (7)
C16	0.0182 (8)	0.0214 (9)	0.0198 (8)	0.0001 (7)	0.0033 (6)	0.0009 (7)
C1	0.0351 (10)	0.0271 (10)	0.0250 (9)	−0.0109 (8)	0.0020 (8)	0.0043 (8)
C4	0.0189 (8)	0.0243 (9)	0.0225 (8)	0.0006 (7)	0.0020 (6)	−0.0002 (7)
C3	0.0299 (10)	0.0250 (10)	0.0260 (9)	0.0030 (7)	0.0010 (7)	−0.0057 (7)
C19	0.0217 (9)	0.0260 (10)	0.0339 (10)	−0.0010 (7)	0.0048 (7)	−0.0086 (8)
C20	0.0259 (10)	0.0246 (10)	0.0427 (11)	−0.0076 (8)	0.0060 (8)	−0.0068 (8)
C2	0.0345 (10)	0.0199 (9)	0.0310 (10)	−0.0042 (8)	−0.0046 (8)	0.0006 (8)

O3—C28	1.236 (2)	O1—C6	1.235 (2)
O4—C39	1.227 (2)	O2—C17	1.232 (2)
N10—C40	1.340 (2)	N5—C18	1.338 (2)
N10—C44	1.337 (2)	N5—C22	1.335 (2)
N8—C36	1.390 (2)	N3—C9	1.390 (2)
N8—C37	1.449 (2)	N3—C15	1.449 (2)
N8—C30	1.452 (2)	N3—C8	1.455 (2)
N6—C27	1.344 (2)	N2—H2	0.8600
N6—C23	1.336 (2)	N2—C6	1.337 (2)
N9—H9	0.8600	N2—C7	1.448 (2)
N9—C39	1.341 (2)	N4—H4	0.8600
N9—C38	1.454 (2)	N4—C17	1.338 (2)
C40—C39	1.509 (2)	N4—C16	1.452 (2)
C40—C41	1.387 (3)	N1—C5	1.342 (2)
N7—H7	0.8600	N1—C1	1.333 (2)
N7—C28	1.336 (2)	C5—C6	1.508 (2)
N7—C29	1.448 (2)	C5—C4	1.383 (2)
C28—C27	1.509 (2)	C17—C18	1.508 (2)
C27—C26	1.381 (2)	C18—C19	1.383 (3)
C36—C31	1.400 (2)	C9—C14	1.404 (2)
C36—C35	1.405 (2)	C9—C10	1.401 (2)
C41—H41	0.9300	C11—H11	0.9300
C41—C42	1.382 (3)	C11—C10	1.383 (2)
C32—H32	0.9300	C11—C12	1.385 (3)
C32—C31	1.385 (2)	C22—H22	0.9300
C32—C33	1.382 (3)	C22—C21	1.380 (3)
C37—H37A	0.9700	C21—H21	0.9300
C37—H37B	0.9700	C21—C20	1.381 (3)
C37—C38	1.534 (2)	C14—H14	0.9300
C23—H23	0.9300	C14—C13	1.388 (2)
C23—C24	1.387 (3)	C15—H15A	0.9700
C26—H26	0.9300	C15—H15B	0.9700
C26—C25	1.388 (2)	C15—C16	1.536 (2)
C31—H31	0.9300	C8—H8A	0.9700
C24—H24	0.9300	C8—H8B	0.9700
C24—C25	1.382 (3)	C8—C7	1.529 (2)
C30—H30A	0.9700	C13—H13	0.9300
C30—H30B	0.9700	C13—C12	1.384 (3)
C30—C29	1.528 (2)	C10—H10	0.9300
C33—H33	0.9300	C12—H12	0.9300
C33—C34	1.383 (3)	C7—H7A	0.9700
C34—H34	0.9300	C7—H7B	0.9700
C34—C35	1.388 (3)	C16—H16A	0.9700
C43—H43	0.9300	C16—H16B	0.9700
C43—C44	1.384 (3)	C1—H1	0.9300
C43—C42	1.382 (3)	C1—C2	1.384 (3)
C44—H44	0.9300	C4—H4A	0.9300
C29—H29A	0.9700	C4—C3	1.381 (3)
C29—H29B	0.9700	C3—H3	0.9300
C42—H42	0.9300	C3—C2	1.381 (3)
C38—H38A	0.9700	C19—H19	0.9300
C38—H38B	0.9700	C19—C20	1.382 (3)
C35—H35	0.9300	C20—H20	0.9300
C25—H25	0.9300	C2—H2A	0.9300
C44—N10—C40	116.80 (15)	C22—N5—C18	117.06 (15)
C36—N8—C37	121.20 (14)	C9—N3—C15	120.88 (14)
C36—N8—C30	121.79 (13)	C9—N3—C8	121.83 (13)
C37—N8—C30	117.01 (13)	C15—N3—C8	117.07 (13)
C23—N6—C27	116.90 (15)	C6—N2—H2	118.6
C39—N9—H9	119.3	C6—N2—C7	122.80 (14)
C39—N9—C38	121.41 (14)	C7—N2—H2	118.6
C38—N9—H9	119.3	C17—N4—H4	119.2
N10—C40—C39	117.07 (15)	C17—N4—C16	121.59 (13)
N10—C40—C41	123.47 (16)	C16—N4—H4	119.2
C41—C40—C39	119.42 (15)	C1—N1—C5	117.02 (15)
C28—N7—H7	118.2	N1—C5—C6	117.30 (14)
C28—N7—C29	123.57 (14)	N1—C5—C4	123.14 (16)
C29—N7—H7	118.2	C4—C5—C6	119.55 (14)
O4—C39—N9	123.26 (16)	O1—C6—N2	124.18 (16)
O4—C39—C40	121.20 (16)	O1—C6—C5	121.22 (14)
N9—C39—C40	115.52 (14)	N2—C6—C5	114.60 (14)
O3—C28—N7	124.11 (15)	O2—C17—N4	123.34 (15)
O3—C28—C27	121.46 (14)	O2—C17—C18	120.88 (15)
N7—C28—C27	114.42 (14)	N4—C17—C18	115.78 (14)
N6—C27—C28	116.48 (14)	N5—C18—C17	117.03 (15)
N6—C27—C26	123.36 (15)	N5—C18—C19	123.43 (15)
C26—C27—C28	120.16 (15)	C19—C18—C17	119.54 (15)
N8—C36—C31	120.78 (15)	N3—C9—C14	121.52 (14)
N8—C36—C35	121.65 (15)	N3—C9—C10	120.73 (15)
C31—C36—C35	117.57 (15)	C10—C9—C14	117.75 (15)
C40—C41—H41	120.7	C10—C11—H11	119.5
C42—C41—C40	118.70 (17)	C10—C11—C12	121.09 (16)
C42—C41—H41	120.7	C12—C11—H11	119.5
C31—C32—H32	119.5	N5—C22—H22	118.1
C33—C32—H32	119.5	N5—C22—C21	123.70 (16)
C33—C32—C31	120.95 (15)	C21—C22—H22	118.1
N8—C37—H37A	108.9	C22—C21—H21	120.8
N8—C37—H37B	108.9	C22—C21—C20	118.38 (16)
N8—C37—C38	113.23 (14)	C20—C21—H21	120.8
H37A—C37—H37B	107.7	C9—C14—H14	120.0
C38—C37—H37A	108.9	C13—C14—C9	120.08 (16)
C38—C37—H37B	108.9	C13—C14—H14	120.0
N6—C23—H23	118.1	N3—C15—H15A	109.0
N6—C23—C24	123.76 (17)	N3—C15—H15B	109.0
C24—C23—H23	118.1	N3—C15—C16	113.09 (14)
C27—C26—H26	120.6	H15A—C15—H15B	107.8
C27—C26—C25	118.81 (16)	C16—C15—H15A	109.0
C25—C26—H26	120.6	C16—C15—H15B	109.0
C36—C31—H31	119.4	N3—C8—H8A	109.3
C32—C31—C36	121.14 (15)	N3—C8—H8B	109.3
C32—C31—H31	119.4	N3—C8—C7	111.76 (14)
C23—C24—H24	120.8	H8A—C8—H8B	107.9
C25—C24—C23	118.43 (17)	C7—C8—H8A	109.3
C25—C24—H24	120.8	C7—C8—H8B	109.3
N8—C30—H30A	109.2	C14—C13—H13	119.1
N8—C30—H30B	109.2	C12—C13—C14	121.79 (17)
N8—C30—C29	112.07 (14)	C12—C13—H13	119.1
H30A—C30—H30B	107.9	C9—C10—H10	119.5
C29—C30—H30A	109.2	C11—C10—C9	121.06 (16)
C29—C30—H30B	109.2	C11—C10—H10	119.5
C32—C33—H33	120.8	C11—C12—H12	120.9
C32—C33—C34	118.44 (16)	C13—C12—C11	118.16 (15)
C34—C33—H33	120.8	C13—C12—H12	120.9
C33—C34—H34	119.2	N2—C7—C8	112.33 (14)
C33—C34—C35	121.54 (16)	N2—C7—H7A	109.1
C35—C34—H34	119.2	N2—C7—H7B	109.1
C44—C43—H43	120.7	C8—C7—H7A	109.1
C42—C43—H43	120.7	C8—C7—H7B	109.1
C42—C43—C44	118.59 (17)	H7A—C7—H7B	107.9
N10—C44—C43	123.74 (17)	N4—C16—C15	110.18 (13)
N10—C44—H44	118.1	N4—C16—H16A	109.6
C43—C44—H44	118.1	N4—C16—H16B	109.6
N7—C29—C30	112.14 (14)	C15—C16—H16A	109.6
N7—C29—H29A	109.2	C15—C16—H16B	109.6
N7—C29—H29B	109.2	H16A—C16—H16B	108.1
C30—C29—H29A	109.2	N1—C1—H1	118.2
C30—C29—H29B	109.2	N1—C1—C2	123.69 (17)
H29A—C29—H29B	107.9	C2—C1—H1	118.2
C41—C42—C43	118.68 (17)	C5—C4—H4A	120.5
C41—C42—H42	120.7	C3—C4—C5	118.91 (16)
C43—C42—H42	120.7	C3—C4—H4A	120.5
N9—C38—C37	110.24 (13)	C4—C3—H3	120.7
N9—C38—H38A	109.6	C4—C3—C2	118.60 (17)
N9—C38—H38B	109.6	C2—C3—H3	120.7
C37—C38—H38A	109.6	C18—C19—H19	120.8
C37—C38—H38B	109.6	C20—C19—C18	118.40 (17)
H38A—C38—H38B	108.1	C20—C19—H19	120.8
C36—C35—H35	119.9	C21—C20—C19	119.02 (18)
C34—C35—C36	120.28 (16)	C21—C20—H20	120.5
C34—C35—H35	119.9	C19—C20—H20	120.5
C26—C25—H25	120.7	C1—C2—H2A	120.7
C24—C25—C26	118.65 (16)	C3—C2—C1	118.58 (17)
C24—C25—H25	120.7	C3—C2—H2A	120.7

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3	0.86	2.44	3.1099 (18)	135
N7—H7···O1i	0.86	2.42	3.0998 (18)	136
C24—H24···O2ii	0.93	2.48	3.311 (2)	149
C25—H25···O4iii	0.93	2.54	3.213 (2)	129
C8—H8A···Cg6iv	0.97	2.72	3.6468 (18)	161
C30—H30B···Cg5v	0.97	2.74	3.6584 (18)	159

Table 1

Hydrogen-bond geometry (Å, °)

Cg5 and Cg6 are the centroids of the C9–C14 benzene and C31–C36 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3	0.86	2.44	3.1099 (18)	135
N7—H7⋯O1i	0.86	2.42	3.0998 (18)	136
C24—H24⋯O2ii	0.93	2.48	3.311 (2)	149
C25—H25⋯O4iii	0.93	2.54	3.213 (2)	129
C8—H8A⋯Cg6iv	0.97	2.72	3.6468 (18)	161
C30—H30B⋯Cg5v	0.97	2.74	3.6584 (18)	159

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