A second monoclinic polymorph for 3-amino-1-(4-meth-oxy-phen-yl)-9,10-dihydro-phenanthrene-2,4-dicarbonitrile.

The title compound, C(23)H(17)N(3)O, has been previously described in a monoclinic P2(1)/c polymorph with Z = 4 [Asiri, Al-Youbi, Faidallah, Ng & Tiekink (2011). Acta Cryst. E67, o2449]. In the new monoclinic P2(1)/n form, with Z = 8, there are two independent mol-ecules, A and B, in the asymmetric unit. In both mol-ecules, the cyclo-hexa-1,3-diene ring has a screw-boat conformation, whereas it is a distorted half-chair in the original polymorph. There is a fold in each mol-ecule, as indicated by the dihedral angle between the benzene rings of the 1,2-dihydro-naphthalene and aniline residues of 33.19 (10)° (mol-ecule A) and 30.6 (10)° (mol-ecule B). The meth-oxy-benzene ring is twisted out of the plane of the aniline residue to which it is connected [dihedral angles = 49.22 (10) and 73.27 (10)°, in A and B respectively]. In the crystal, the two independent mol-ecules self-associate via N-H⋯N hydrogen bonds, generating a 12-membered {⋯HNC(3)N}(2) synthon. These are connected into a supra-molecular tape in the (-101) plane by N-H⋯O(meth-oxy) inter-actions. In the P2(1)/c polymorph, supra-molecular layers are formed by N-H⋯N and N-H⋯O inter-actions.

Related literature

For background to the biological activity of related phenanthrene compounds, see: Wang et al. (2010 ▶); Rostom et al. (2011 ▶). For related structures, see: Asiri et al. (2011a ▶,b ▶); Al-Youbi et al. (2012 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C23H17N3O

M = 351.40

Monoclinic,

a = 11.5197 (6) Å

b = 25.1585 (12) Å

c = 11.9564 (6) Å

β = 90.719 (5)°

V = 3464.9 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.35 × 0.35 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.971, T max = 0.992

20450 measured reflections

7990 independent reflections

5348 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.156

S = 1.04

7990 reflections

503 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); 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: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812011798/bt5850sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011798/bt5850Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812011798/bt5850Isup3.cml

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

C23H17N3O	F(000) = 1472
Mr = 351.40	Dx = 1.347 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4701 reflections
a = 11.5197 (6) Å	θ = 2.4–27.5°
b = 25.1585 (12) Å	µ = 0.09 mm−1
c = 11.9564 (6) Å	T = 100 K
β = 90.719 (5)°	Prism, orange
V = 3464.9 (3) Å3	0.35 × 0.35 × 0.10 mm
Z = 8

Agilent SuperNova Dual diffractometer with an Atlas detector	7990 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	5348 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.055
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.4°
ω scan	h = −14→14
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −24→32
Tmin = 0.971, Tmax = 0.992	l = −15→12
20450 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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.057P)2 + 0.839P] where P = (Fo2 + 2Fc2)/3
7990 reflections	(Δ/σ)max = 0.001
503 parameters	Δρmax = 0.33 e Å−3
4 restraints	Δρmin = −0.25 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.10070 (14)	0.15244 (6)	0.28185 (14)	0.0303 (4)
O2	0.84581 (15)	0.39154 (6)	1.09183 (14)	0.0328 (4)
N1	0.35813 (17)	0.54827 (8)	0.59073 (16)	0.0301 (5)
N2	0.44427 (18)	0.41933 (8)	0.60868 (17)	0.0286 (4)
N3	0.45795 (18)	0.28657 (8)	0.52814 (17)	0.0341 (5)
N4	0.48229 (19)	0.77085 (8)	0.78737 (19)	0.0377 (5)
N5	0.49102 (17)	0.64209 (8)	0.72209 (16)	0.0268 (4)
N6	0.56385 (16)	0.51011 (7)	0.73917 (15)	0.0249 (4)
C1	0.15965 (18)	0.40545 (8)	0.38717 (18)	0.0220 (5)
C2	0.04533 (18)	0.40182 (9)	0.32242 (19)	0.0242 (5)
H2A	0.0596	0.4063	0.2415	0.029*
H2B	0.0102	0.3664	0.3338	0.029*
C3	−0.03757 (19)	0.44473 (8)	0.36222 (19)	0.0256 (5)
H3A	−0.1106	0.4432	0.3178	0.031*
H3B	−0.0566	0.4386	0.4417	0.031*
C4	0.01701 (19)	0.49843 (9)	0.34957 (18)	0.0235 (5)
C5	−0.0443 (2)	0.54234 (9)	0.31252 (19)	0.0275 (5)
H5	−0.1252	0.5393	0.2974	0.033*
C6	0.0111 (2)	0.59115 (9)	0.29700 (19)	0.0292 (5)
H6	−0.0323	0.6216	0.2748	0.035*
C7	0.1298 (2)	0.59477 (9)	0.31422 (18)	0.0268 (5)
H7	0.1686	0.6273	0.2992	0.032*
C8	0.1925 (2)	0.55150 (9)	0.35315 (18)	0.0249 (5)
H8	0.2738	0.5546	0.3653	0.030*
C9	0.13701 (19)	0.50318 (8)	0.37478 (17)	0.0222 (5)
C10	0.19815 (18)	0.45619 (8)	0.41975 (18)	0.0220 (5)
C11	0.29307 (18)	0.46056 (8)	0.49625 (18)	0.0218 (5)
C12	0.35534 (19)	0.41555 (8)	0.53271 (18)	0.0225 (5)
C13	0.32176 (19)	0.36595 (8)	0.48802 (18)	0.0225 (5)
C14	0.22155 (19)	0.36049 (8)	0.41905 (18)	0.0211 (5)
C15	0.32687 (18)	0.51051 (9)	0.54559 (18)	0.0221 (5)
C16	0.3947 (2)	0.32124 (9)	0.51117 (18)	0.0256 (5)
C17	0.18686 (18)	0.30606 (8)	0.38398 (18)	0.0228 (5)
C18	0.1762 (2)	0.26602 (9)	0.46277 (19)	0.0268 (5)
H18	0.1886	0.2742	0.5396	0.032*
C19	0.1478 (2)	0.21416 (9)	0.4326 (2)	0.0278 (5)
H19	0.1418	0.1872	0.4879	0.033*
C20	0.12838 (18)	0.20240 (9)	0.3206 (2)	0.0248 (5)
C21	0.13611 (18)	0.24202 (9)	0.24038 (19)	0.0248 (5)
H21	0.1213	0.2339	0.1639	0.030*
C22	0.16527 (18)	0.29310 (9)	0.27145 (18)	0.0242 (5)
H22	0.1708	0.3199	0.2159	0.029*
C23	0.1006 (2)	0.11064 (9)	0.3630 (2)	0.0355 (6)
H23A	0.0808	0.0770	0.3263	0.053*
H23B	0.0430	0.1185	0.4204	0.053*
H23C	0.1777	0.1078	0.3980	0.053*
C24	0.69808 (19)	0.63961 (8)	1.01349 (18)	0.0218 (5)
C25	0.7659 (2)	0.64074 (9)	1.12243 (18)	0.0259 (5)
H25A	0.8455	0.6540	1.1092	0.031*
H25B	0.7717	0.6043	1.1535	0.031*
C26	0.7052 (2)	0.67681 (9)	1.20495 (18)	0.0262 (5)
H26A	0.6265	0.6630	1.2203	0.031*
H26B	0.7496	0.6780	1.2763	0.031*
C27	0.69672 (18)	0.73163 (9)	1.15568 (18)	0.0233 (5)
C28	0.71185 (19)	0.77700 (9)	1.22026 (19)	0.0269 (5)
H28	0.7195	0.7738	1.2992	0.032*
C29	0.71595 (19)	0.82680 (9)	1.1717 (2)	0.0290 (5)
H29	0.7253	0.8575	1.2172	0.035*
C30	0.7064 (2)	0.83184 (9)	1.0572 (2)	0.0279 (5)
H30	0.7140	0.8658	1.0233	0.033*
C31	0.68564 (19)	0.78737 (9)	0.99132 (19)	0.0252 (5)
H31	0.6764	0.7912	0.9127	0.030*
C32	0.67824 (18)	0.73687 (8)	1.03971 (19)	0.0229 (5)
C33	0.65311 (18)	0.68813 (8)	0.97334 (18)	0.0219 (5)
C34	0.58428 (18)	0.68879 (8)	0.87531 (18)	0.0213 (5)
C35	0.56000 (18)	0.64163 (8)	0.81431 (18)	0.0210 (5)
C36	0.61077 (18)	0.59420 (8)	0.85423 (18)	0.0213 (5)
C37	0.67812 (19)	0.59281 (8)	0.95346 (18)	0.0215 (5)
C38	0.5298 (2)	0.73604 (9)	0.8308 (2)	0.0275 (5)
C39	0.58701 (18)	0.54667 (9)	0.79306 (18)	0.0215 (5)
C40	0.72664 (19)	0.54034 (8)	0.99069 (17)	0.0209 (5)
C41	0.6805 (2)	0.51357 (9)	1.08273 (19)	0.0266 (5)
H41	0.6193	0.5293	1.1237	0.032*
C42	0.7230 (2)	0.46448 (9)	1.11451 (19)	0.0282 (5)
H42	0.6908	0.4467	1.1769	0.034*
C43	0.81266 (19)	0.44099 (9)	1.05564 (18)	0.0244 (5)
C44	0.8609 (2)	0.46710 (9)	0.96590 (19)	0.0253 (5)
H44	0.9237	0.4517	0.9266	0.030*
C45	0.81622 (19)	0.51622 (8)	0.93386 (18)	0.0240 (5)
H45	0.8482	0.5337	0.8710	0.029*
C46	0.9325 (2)	0.36427 (10)	1.0298 (2)	0.0368 (6)
H46A	0.9475	0.3295	1.0640	0.055*
H46B	1.0041	0.3852	1.0303	0.055*
H46C	0.9052	0.3593	0.9525	0.055*
H1	0.4837 (17)	0.3901 (6)	0.6221 (18)	0.020 (6)*
H2	0.466 (2)	0.4511 (6)	0.633 (2)	0.044 (8)*
H3	0.469 (2)	0.6121 (6)	0.690 (2)	0.037 (7)*
H4	0.460 (2)	0.6715 (6)	0.695 (2)	0.034 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0352 (9)	0.0210 (8)	0.0348 (9)	−0.0020 (7)	−0.0035 (8)	−0.0052 (7)
O2	0.0406 (10)	0.0253 (9)	0.0326 (9)	0.0105 (7)	0.0036 (8)	0.0064 (7)
N1	0.0324 (11)	0.0285 (11)	0.0292 (11)	0.0001 (9)	−0.0087 (9)	−0.0013 (9)
N2	0.0327 (11)	0.0217 (11)	0.0312 (11)	−0.0024 (9)	−0.0098 (9)	−0.0009 (9)
N3	0.0395 (12)	0.0264 (11)	0.0360 (12)	0.0011 (10)	−0.0081 (10)	0.0000 (9)
N4	0.0426 (12)	0.0272 (11)	0.0431 (13)	0.0031 (10)	−0.0126 (11)	0.0005 (10)
N5	0.0344 (11)	0.0204 (11)	0.0254 (10)	0.0015 (9)	−0.0075 (9)	0.0019 (9)
N6	0.0275 (10)	0.0229 (10)	0.0240 (10)	0.0010 (8)	−0.0055 (8)	0.0010 (8)
C1	0.0230 (11)	0.0243 (11)	0.0187 (10)	−0.0033 (9)	0.0022 (9)	−0.0005 (9)
C2	0.0256 (11)	0.0244 (11)	0.0226 (11)	−0.0036 (9)	−0.0024 (10)	−0.0009 (9)
C3	0.0243 (11)	0.0280 (12)	0.0246 (11)	−0.0025 (9)	−0.0003 (10)	−0.0016 (10)
C4	0.0249 (11)	0.0267 (12)	0.0190 (11)	0.0006 (9)	0.0006 (9)	−0.0039 (9)
C5	0.0280 (12)	0.0300 (13)	0.0245 (12)	−0.0007 (10)	−0.0009 (10)	−0.0031 (10)
C6	0.0370 (13)	0.0264 (12)	0.0243 (12)	0.0070 (10)	−0.0035 (11)	−0.0011 (10)
C7	0.0352 (13)	0.0240 (12)	0.0213 (11)	−0.0032 (10)	−0.0014 (10)	−0.0053 (9)
C8	0.0301 (12)	0.0242 (12)	0.0204 (11)	−0.0010 (9)	−0.0024 (10)	−0.0037 (9)
C9	0.0270 (11)	0.0222 (11)	0.0174 (10)	0.0000 (9)	0.0013 (9)	−0.0037 (9)
C10	0.0220 (11)	0.0244 (11)	0.0199 (11)	−0.0014 (9)	0.0044 (9)	−0.0006 (9)
C11	0.0222 (11)	0.0205 (11)	0.0228 (11)	−0.0030 (9)	0.0025 (9)	−0.0018 (9)
C12	0.0233 (11)	0.0238 (11)	0.0205 (11)	−0.0027 (9)	0.0033 (9)	0.0002 (9)
C13	0.0269 (11)	0.0213 (11)	0.0194 (11)	−0.0003 (9)	0.0017 (9)	0.0018 (9)
C14	0.0255 (11)	0.0200 (11)	0.0180 (10)	−0.0019 (9)	0.0035 (9)	−0.0004 (9)
C15	0.0218 (11)	0.0222 (11)	0.0221 (11)	0.0009 (9)	−0.0009 (9)	−0.0005 (9)
C16	0.0327 (12)	0.0219 (12)	0.0220 (11)	−0.0069 (10)	−0.0011 (10)	−0.0020 (9)
C17	0.0223 (11)	0.0224 (11)	0.0238 (11)	−0.0005 (9)	0.0010 (10)	−0.0008 (9)
C18	0.0326 (12)	0.0253 (12)	0.0225 (11)	−0.0028 (10)	−0.0016 (10)	−0.0028 (10)
C19	0.0330 (12)	0.0224 (12)	0.0279 (12)	−0.0025 (10)	0.0010 (11)	0.0024 (10)
C20	0.0212 (11)	0.0221 (11)	0.0311 (12)	−0.0010 (9)	0.0008 (10)	−0.0064 (10)
C21	0.0227 (11)	0.0276 (12)	0.0239 (11)	−0.0003 (9)	−0.0008 (10)	−0.0044 (10)
C22	0.0241 (11)	0.0273 (12)	0.0212 (11)	0.0005 (9)	0.0033 (10)	0.0007 (9)
C23	0.0446 (15)	0.0202 (12)	0.0415 (15)	−0.0017 (11)	−0.0057 (13)	−0.0033 (11)
C24	0.0239 (11)	0.0224 (11)	0.0191 (11)	−0.0022 (9)	0.0000 (9)	0.0012 (9)
C25	0.0321 (12)	0.0221 (11)	0.0232 (12)	−0.0008 (9)	−0.0065 (10)	−0.0004 (9)
C26	0.0326 (12)	0.0269 (12)	0.0190 (11)	−0.0045 (10)	−0.0032 (10)	0.0012 (9)
C27	0.0222 (11)	0.0253 (12)	0.0223 (11)	−0.0014 (9)	0.0005 (10)	−0.0021 (9)
C28	0.0280 (12)	0.0277 (12)	0.0250 (12)	0.0024 (10)	−0.0025 (10)	−0.0041 (10)
C29	0.0259 (12)	0.0286 (12)	0.0323 (13)	0.0041 (10)	−0.0031 (11)	−0.0106 (10)
C30	0.0296 (12)	0.0191 (11)	0.0349 (13)	0.0007 (9)	−0.0021 (11)	−0.0006 (10)
C31	0.0272 (11)	0.0239 (12)	0.0246 (12)	0.0012 (9)	−0.0014 (10)	−0.0003 (10)
C32	0.0210 (11)	0.0214 (11)	0.0266 (12)	−0.0008 (9)	0.0033 (10)	−0.0022 (9)
C33	0.0227 (11)	0.0238 (11)	0.0195 (11)	−0.0012 (9)	0.0031 (9)	0.0002 (9)
C34	0.0242 (11)	0.0191 (11)	0.0206 (11)	−0.0007 (9)	0.0009 (9)	0.0009 (9)
C35	0.0222 (11)	0.0222 (11)	0.0187 (11)	−0.0015 (9)	0.0016 (9)	−0.0004 (9)
C36	0.0250 (11)	0.0187 (11)	0.0201 (11)	−0.0016 (9)	0.0016 (9)	−0.0011 (9)
C37	0.0263 (11)	0.0199 (11)	0.0183 (10)	−0.0016 (9)	0.0019 (9)	0.0028 (9)
C38	0.0295 (12)	0.0256 (12)	0.0274 (12)	0.0002 (10)	−0.0029 (10)	−0.0034 (10)
C39	0.0212 (11)	0.0242 (11)	0.0193 (10)	0.0030 (9)	0.0003 (9)	0.0037 (9)
C40	0.0256 (11)	0.0199 (11)	0.0170 (10)	−0.0032 (9)	−0.0042 (9)	−0.0005 (9)
C41	0.0278 (12)	0.0273 (12)	0.0248 (11)	0.0025 (10)	0.0029 (10)	0.0012 (10)
C42	0.0332 (13)	0.0277 (12)	0.0240 (12)	−0.0001 (10)	0.0045 (11)	0.0057 (10)
C43	0.0285 (12)	0.0224 (11)	0.0223 (11)	0.0008 (9)	−0.0043 (10)	0.0018 (9)
C44	0.0263 (11)	0.0261 (12)	0.0236 (11)	0.0002 (9)	0.0022 (10)	−0.0038 (10)
C45	0.0301 (12)	0.0226 (11)	0.0191 (11)	−0.0052 (9)	0.0007 (10)	0.0010 (9)
C46	0.0420 (14)	0.0291 (13)	0.0392 (15)	0.0112 (11)	0.0017 (13)	0.0003 (11)

O1—C20	1.376 (3)	C20—C21	1.387 (3)
O1—C23	1.431 (3)	C21—C22	1.378 (3)
O2—C43	1.370 (3)	C21—H21	0.9500
O2—C46	1.427 (3)	C22—H22	0.9500
N1—C15	1.148 (3)	C23—H23A	0.9800
N2—C12	1.364 (3)	C23—H23B	0.9800
N2—H1	0.879 (9)	C23—H23C	0.9800
N2—H2	0.887 (10)	C24—C37	1.396 (3)
N3—C16	1.153 (3)	C24—C33	1.408 (3)
N4—C38	1.153 (3)	C24—C25	1.511 (3)
N5—C35	1.351 (3)	C25—C26	1.518 (3)
N5—H3	0.884 (10)	C25—H25A	0.9900
N5—H4	0.881 (10)	C25—H25B	0.9900
N6—C39	1.152 (3)	C26—C27	1.503 (3)
C1—C14	1.388 (3)	C26—H26A	0.9900
C1—C10	1.405 (3)	C26—H26B	0.9900
C1—C2	1.522 (3)	C27—C28	1.388 (3)
C2—C3	1.521 (3)	C27—C32	1.406 (3)
C2—H2A	0.9900	C28—C29	1.382 (3)
C2—H2B	0.9900	C28—H28	0.9500
C3—C4	1.499 (3)	C29—C30	1.378 (3)
C3—H3A	0.9900	C29—H29	0.9500
C3—H3B	0.9900	C30—C31	1.387 (3)
C4—C5	1.381 (3)	C30—H30	0.9500
C4—C9	1.416 (3)	C31—C32	1.399 (3)
C5—C6	1.398 (3)	C31—H31	0.9500
C5—H5	0.9500	C32—C33	1.487 (3)
C6—C7	1.383 (3)	C33—C34	1.407 (3)
C6—H6	0.9500	C34—C35	1.419 (3)
C7—C8	1.384 (3)	C34—C38	1.443 (3)
C7—H7	0.9500	C35—C36	1.410 (3)
C8—C9	1.399 (3)	C36—C37	1.410 (3)
C8—H8	0.9500	C36—C39	1.426 (3)
C9—C10	1.474 (3)	C37—C40	1.499 (3)
C10—C11	1.421 (3)	C40—C45	1.383 (3)
C11—C12	1.407 (3)	C40—C41	1.401 (3)
C11—C15	1.440 (3)	C41—C42	1.380 (3)
C12—C13	1.410 (3)	C41—H41	0.9500
C13—C14	1.417 (3)	C42—C43	1.389 (3)
C13—C16	1.429 (3)	C42—H42	0.9500
C14—C17	1.486 (3)	C43—C44	1.381 (3)
C17—C18	1.386 (3)	C44—C45	1.391 (3)
C17—C22	1.404 (3)	C44—H44	0.9500
C18—C19	1.391 (3)	C45—H45	0.9500
C18—H18	0.9500	C46—H46A	0.9800
C19—C20	1.387 (3)	C46—H46B	0.9800
C19—H19	0.9500	C46—H46C	0.9800
C20—O1—C23	116.44 (18)	H23A—C23—H23B	109.5
C43—O2—C46	117.81 (17)	O1—C23—H23C	109.5
C12—N2—H1	116.5 (15)	H23A—C23—H23C	109.5
C12—N2—H2	119.4 (18)	H23B—C23—H23C	109.5
H1—N2—H2	123 (2)	C37—C24—C33	119.9 (2)
C35—N5—H3	121.0 (18)	C37—C24—C25	122.62 (19)
C35—N5—H4	122.4 (17)	C33—C24—C25	117.50 (19)
H3—N5—H4	116 (2)	C24—C25—C26	109.51 (19)
C14—C1—C10	120.3 (2)	C24—C25—H25A	109.8
C14—C1—C2	121.95 (19)	C26—C25—H25A	109.8
C10—C1—C2	117.62 (19)	C24—C25—H25B	109.8
C3—C2—C1	109.93 (18)	C26—C25—H25B	109.8
C3—C2—H2A	109.7	H25A—C25—H25B	108.2
C1—C2—H2A	109.7	C27—C26—C25	108.80 (17)
C3—C2—H2B	109.7	C27—C26—H26A	109.9
C1—C2—H2B	109.7	C25—C26—H26A	109.9
H2A—C2—H2B	108.2	C27—C26—H26B	109.9
C4—C3—C2	110.02 (18)	C25—C26—H26B	109.9
C4—C3—H3A	109.7	H26A—C26—H26B	108.3
C2—C3—H3A	109.7	C28—C27—C32	119.2 (2)
C4—C3—H3B	109.7	C28—C27—C26	122.0 (2)
C2—C3—H3B	109.7	C32—C27—C26	118.74 (19)
H3A—C3—H3B	108.2	C29—C28—C27	121.1 (2)
C5—C4—C9	119.7 (2)	C29—C28—H28	119.5
C5—C4—C3	122.7 (2)	C27—C28—H28	119.5
C9—C4—C3	117.7 (2)	C30—C29—C28	119.9 (2)
C4—C5—C6	120.8 (2)	C30—C29—H29	120.1
C4—C5—H5	119.6	C28—C29—H29	120.1
C6—C5—H5	119.6	C29—C30—C31	120.1 (2)
C7—C6—C5	119.4 (2)	C29—C30—H30	120.0
C7—C6—H6	120.3	C31—C30—H30	120.0
C5—C6—H6	120.3	C30—C31—C32	120.6 (2)
C6—C7—C8	120.6 (2)	C30—C31—H31	119.7
C6—C7—H7	119.7	C32—C31—H31	119.7
C8—C7—H7	119.7	C31—C32—C27	118.9 (2)
C7—C8—C9	120.5 (2)	C31—C32—C33	122.7 (2)
C7—C8—H8	119.7	C27—C32—C33	118.35 (19)
C9—C8—H8	119.7	C24—C33—C34	119.70 (19)
C8—C9—C4	118.7 (2)	C24—C33—C32	117.69 (19)
C8—C9—C10	123.2 (2)	C34—C33—C32	122.59 (19)
C4—C9—C10	118.07 (19)	C33—C34—C35	121.59 (19)
C1—C10—C11	119.1 (2)	C33—C34—C38	123.69 (19)
C1—C10—C9	118.7 (2)	C35—C34—C38	114.69 (19)
C11—C10—C9	122.21 (19)	N5—C35—C36	121.38 (19)
C12—C11—C10	121.5 (2)	N5—C35—C34	121.51 (19)
C12—C11—C15	116.2 (2)	C36—C35—C34	117.11 (19)
C10—C11—C15	122.23 (19)	C35—C36—C37	121.83 (19)
N2—C12—C13	121.0 (2)	C35—C36—C39	117.39 (19)
N2—C12—C11	121.7 (2)	C37—C36—C39	120.71 (19)
C13—C12—C11	117.3 (2)	C24—C37—C36	119.81 (19)
C12—C13—C14	121.6 (2)	C24—C37—C40	122.10 (19)
C12—C13—C16	117.7 (2)	C36—C37—C40	118.09 (18)
C14—C13—C16	120.6 (2)	N4—C38—C34	173.6 (2)
C1—C14—C13	119.5 (2)	N6—C39—C36	175.8 (2)
C1—C14—C17	122.6 (2)	C45—C40—C41	117.9 (2)
C13—C14—C17	117.90 (19)	C45—C40—C37	121.21 (18)
N1—C15—C11	175.0 (2)	C41—C40—C37	120.86 (19)
N3—C16—C13	176.7 (2)	C42—C41—C40	120.6 (2)
C18—C17—C22	117.8 (2)	C42—C41—H41	119.7
C18—C17—C14	120.3 (2)	C40—C41—H41	119.7
C22—C17—C14	121.90 (19)	C41—C42—C43	120.3 (2)
C17—C18—C19	121.9 (2)	C41—C42—H42	119.8
C17—C18—H18	119.1	C43—C42—H42	119.8
C19—C18—H18	119.1	O2—C43—C44	124.35 (19)
C20—C19—C18	119.0 (2)	O2—C43—C42	115.62 (19)
C20—C19—H19	120.5	C44—C43—C42	120.0 (2)
C18—C19—H19	120.5	C43—C44—C45	119.1 (2)
O1—C20—C19	123.6 (2)	C43—C44—H44	120.5
O1—C20—C21	116.1 (2)	C45—C44—H44	120.5
C19—C20—C21	120.2 (2)	C40—C45—C44	122.0 (2)
C22—C21—C20	120.1 (2)	C40—C45—H45	119.0
C22—C21—H21	119.9	C44—C45—H45	119.0
C20—C21—H21	119.9	O2—C46—H46A	109.5
C21—C22—C17	121.0 (2)	O2—C46—H46B	109.5
C21—C22—H22	119.5	H46A—C46—H46B	109.5
C17—C22—H22	119.5	O2—C46—H46C	109.5
O1—C23—H23A	109.5	H46A—C46—H46C	109.5
O1—C23—H23B	109.5	H46B—C46—H46C	109.5
C14—C1—C2—C3	142.7 (2)	C37—C24—C25—C26	−137.3 (2)
C10—C1—C2—C3	−33.8 (3)	C33—C24—C25—C26	42.0 (3)
C1—C2—C3—C4	57.0 (2)	C24—C25—C26—C27	−59.1 (2)
C2—C3—C4—C5	139.7 (2)	C25—C26—C27—C28	−141.3 (2)
C2—C3—C4—C9	−38.9 (3)	C25—C26—C27—C32	35.7 (3)
C9—C4—C5—C6	1.5 (3)	C32—C27—C28—C29	−3.9 (3)
C3—C4—C5—C6	−177.0 (2)	C26—C27—C28—C29	173.1 (2)
C4—C5—C6—C7	2.9 (3)	C27—C28—C29—C30	−0.8 (3)
C5—C6—C7—C8	−4.0 (3)	C28—C29—C30—C31	3.9 (3)
C6—C7—C8—C9	0.6 (3)	C29—C30—C31—C32	−2.2 (3)
C7—C8—C9—C4	3.9 (3)	C30—C31—C32—C27	−2.5 (3)
C7—C8—C9—C10	−177.96 (19)	C30—C31—C32—C33	178.4 (2)
C5—C4—C9—C8	−4.9 (3)	C28—C27—C32—C31	5.5 (3)
C3—C4—C9—C8	173.76 (19)	C26—C27—C32—C31	−171.6 (2)
C5—C4—C9—C10	176.82 (19)	C28—C27—C32—C33	−175.32 (19)
C3—C4—C9—C10	−4.5 (3)	C26—C27—C32—C33	7.6 (3)
C14—C1—C10—C11	−7.3 (3)	C37—C24—C33—C34	2.6 (3)
C2—C1—C10—C11	169.22 (19)	C25—C24—C33—C34	−176.74 (18)
C14—C1—C10—C9	173.81 (19)	C37—C24—C33—C32	−179.21 (18)
C2—C1—C10—C9	−9.7 (3)	C25—C24—C33—C32	1.5 (3)
C8—C9—C10—C1	−147.5 (2)	C31—C32—C33—C24	151.2 (2)
C4—C9—C10—C1	30.7 (3)	C27—C32—C33—C24	−27.9 (3)
C8—C9—C10—C11	33.7 (3)	C31—C32—C33—C34	−30.6 (3)
C4—C9—C10—C11	−148.1 (2)	C27—C32—C33—C34	150.2 (2)
C1—C10—C11—C12	5.4 (3)	C24—C33—C34—C35	−0.9 (3)
C9—C10—C11—C12	−175.76 (19)	C32—C33—C34—C35	−179.01 (19)
C1—C10—C11—C15	−171.03 (18)	C24—C33—C34—C38	176.9 (2)
C9—C10—C11—C15	7.8 (3)	C32—C33—C34—C38	−1.2 (3)
C10—C11—C12—N2	−178.0 (2)	C33—C34—C35—N5	177.97 (19)
C15—C11—C12—N2	−1.4 (3)	C38—C34—C35—N5	0.0 (3)
C10—C11—C12—C13	1.6 (3)	C33—C34—C35—C36	−1.9 (3)
C15—C11—C12—C13	178.25 (18)	C38—C34—C35—C36	−179.84 (19)
N2—C12—C13—C14	172.7 (2)	N5—C35—C36—C37	−176.77 (19)
C11—C12—C13—C14	−6.9 (3)	C34—C35—C36—C37	3.1 (3)
N2—C12—C13—C16	−9.5 (3)	N5—C35—C36—C39	0.3 (3)
C11—C12—C13—C16	170.85 (19)	C34—C35—C36—C39	−179.80 (18)
C10—C1—C14—C13	2.2 (3)	C33—C24—C37—C36	−1.4 (3)
C2—C1—C14—C13	−174.18 (19)	C25—C24—C37—C36	177.87 (19)
C10—C1—C14—C17	−178.03 (18)	C33—C24—C37—C40	178.31 (18)
C2—C1—C14—C17	5.6 (3)	C25—C24—C37—C40	−2.4 (3)
C12—C13—C14—C1	5.1 (3)	C35—C36—C37—C24	−1.5 (3)
C16—C13—C14—C1	−172.57 (19)	C39—C36—C37—C24	−178.50 (19)
C12—C13—C14—C17	−174.65 (18)	C35—C36—C37—C40	178.76 (18)
C16—C13—C14—C17	7.6 (3)	C39—C36—C37—C40	1.7 (3)
C1—C14—C17—C18	−129.0 (2)	C24—C37—C40—C45	−108.3 (2)
C13—C14—C17—C18	50.8 (3)	C36—C37—C40—C45	71.4 (3)
C1—C14—C17—C22	51.8 (3)	C24—C37—C40—C41	73.3 (3)
C13—C14—C17—C22	−128.4 (2)	C36—C37—C40—C41	−107.0 (2)
C22—C17—C18—C19	1.5 (3)	C45—C40—C41—C42	−0.5 (3)
C14—C17—C18—C19	−177.7 (2)	C37—C40—C41—C42	177.9 (2)
C17—C18—C19—C20	−0.7 (3)	C40—C41—C42—C43	0.2 (4)
C23—O1—C20—C19	−4.4 (3)	C46—O2—C43—C44	−2.8 (3)
C23—O1—C20—C21	175.8 (2)	C46—O2—C43—C42	176.1 (2)
C18—C19—C20—O1	179.52 (19)	C41—C42—C43—O2	−177.9 (2)
C18—C19—C20—C21	−0.7 (3)	C41—C42—C43—C44	1.0 (4)
O1—C20—C21—C22	−178.95 (18)	O2—C43—C44—C45	177.0 (2)
C19—C20—C21—C22	1.2 (3)	C42—C43—C44—C45	−1.8 (3)
C20—C21—C22—C17	−0.4 (3)	C41—C40—C45—C44	−0.3 (3)
C18—C17—C22—C21	−1.0 (3)	C37—C40—C45—C44	−178.8 (2)
C14—C17—C22—C21	178.30 (19)	C43—C44—C45—C40	1.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N6	0.89 (1)	2.25 (2)	3.081 (3)	157 (3)
N5—H3···N1	0.88 (1)	2.36 (1)	3.213 (3)	162 (2)
N2—H1···O1i	0.88 (2)	2.56 (2)	3.271 (3)	139 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N6	0.89 (1)	2.25 (2)	3.081 (3)	157 (3)
N5—H3⋯N1	0.88 (1)	2.36 (1)	3.213 (3)	162 (2)
N2—H1⋯O1i	0.88 (2)	2.56 (2)	3.271 (3)	139 (2)

Symmetry code: (i) .