4-(2-Nitro-benz-yl)-3-phenyl-3,4-di-hydro-2H-1,4-benzoxazin-2-ol.

The title compound, C21H18N2O4, crystallizes with two independent mol-ecules (A and B) in the asymmetric unit. In both mol-ecules the oxazine ring has an envelope conformation with the hydroxyl-substituted C atom as the flap. The nitro-benzyl ring and the phenyl ring are almost normal to the mean plane of the benzooxazine ring system with dihdral angles of 85.72 (15) and 82.69 (15)°, respectively, in mol-ecule A, and 85.79 (15) and 87.72 (15)°, respectively, in mol-ecule B. The main difference in the conformation of the two mol-ecules concerns the dihedral angle between the nitro-benzyl ring and the phenyl ring, viz. 79.67 (18) in mol-ecule A and 71.13 (18)° in mol-ecule B. In the crystal, the A and B mol-ecules are linked by an O-H⋯O hydrogen bond. These units are then linked via C-H⋯O hydrogen bonds, forming sheets lying parallel to (010). Further C-H⋯O hydrogen bonds link the sheets to form a three-dimensional network. There are also O-H⋯π and C-H⋯π inter-actions present, reinforcing the three-dimensional structure.

Related literature

For the preparation and applications of similar structures, see: Ozden et al. (1992 ▶); Hartenstein & Sicker (1994 ▶); Ilas et al. (2005 ▶); Touzeau et al. (2003 ▶); Torisu et al. (2004 ▶); Largeron et al. (1999 ▶).

Experimental

Crystal data

C21H18N2O4

M = 362.37

Orthorhombic,

a = 12.7332 (14) Å

b = 14.2777 (14) Å

c = 19.003 (2) Å

V = 3454.8 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 150 K

0.13 × 0.05 × 0.03 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.860, T max = 1.000

19156 measured reflections

3161 independent reflections

4907 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.114

S = 1.04

3161 reflections

489 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.71 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2011 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814015645/bq2396sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814015645/bq2396Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814015645/bq2396Isup3.cml

CCDC reference: 1012140

Additional supporting information: crystallographic information; 3D view; checkCIF report

C21H18N2O4	F(000) = 1520
Mr = 362.37	Dx = 1.393 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4509 reflections
a = 12.7332 (14) Å	θ = 2.4–24.4°
b = 14.2777 (14) Å	µ = 0.10 mm−1
c = 19.003 (2) Å	T = 150 K
V = 3454.8 (6) Å3	Stick, colourless
Z = 8	0.13 × 0.05 × 0.03 mm

Bruker APEXII CCD area-detector diffractometer	4907 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
φ and ω scans	θmax = 25.1°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −15→14
Tmin = 0.860, Tmax = 1.000	k = −17→16
19156 measured reflections	l = −20→22
3161 independent 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0733P)2 + 1.1329P] where P = (Fo2 + 2Fc2)/3
3161 reflections	(Δ/σ)max < 0.001
489 parameters	Δρmax = 0.71 e Å−3
1 restraint	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
O1A	0.35335 (19)	0.31206 (17)	0.27744 (14)	0.0169 (6)
O1B	0.08759 (19)	0.32183 (18)	0.40303 (14)	0.0188 (6)
O2B	−0.0900 (2)	0.35721 (17)	0.41491 (15)	0.0223 (6)
H2B	−0.0909	0.3919	0.3805	0.034*
O2A	0.1747 (2)	0.3367 (2)	0.26572 (16)	0.0290 (7)
H2A	0.1429	0.3446	0.3028	0.043*
O22B	−0.0711 (3)	0.2367 (2)	0.80910 (16)	0.0368 (8)
O21B	−0.0793 (3)	0.13604 (19)	0.72486 (16)	0.0353 (8)
O22A	0.1994 (3)	0.1316 (2)	−0.04698 (17)	0.0341 (7)
C20A	0.4687 (3)	0.4126 (2)	0.2155 (2)	0.0157 (8)
H20A	0.4941	0.4337	0.2585	0.019*
N1A	0.2735 (2)	0.2432 (2)	0.15006 (17)	0.0156 (7)
N1B	−0.0003 (2)	0.2559 (2)	0.52882 (17)	0.0157 (6)
N2B	−0.0921 (3)	0.2144 (2)	0.74825 (18)	0.0230 (8)
C16A	0.3515 (3)	0.3115 (2)	0.1502 (2)	0.0142 (7)
C8A	0.2519 (3)	0.2689 (3)	0.2753 (2)	0.0168 (8)
H8A	0.2393	0.2368	0.3201	0.02*
C10A	0.3123 (3)	0.1121 (2)	0.23395 (18)	0.0151 (8)
C4A	0.0388 (3)	0.4109 (3)	0.0605 (2)	0.0281 (10)
H4A	0.0101	0.4577	0.0886	0.034*
C5B	−0.2489 (3)	0.4199 (3)	0.6959 (2)	0.0275 (9)
H5B	−0.294	0.4629	0.7168	0.033*
N2A	0.1720 (3)	0.2069 (2)	−0.06923 (18)	0.0265 (8)
C13A	0.4302 (3)	−0.0451 (3)	0.2722 (2)	0.0223 (9)
H13A	0.4693	−0.0974	0.2849	0.027*
C14A	0.4782 (3)	0.0306 (3)	0.2398 (2)	0.0222 (9)
H14A	0.55	0.0292	0.2309	0.027*
C18A	0.4715 (3)	0.4166 (2)	0.0898 (2)	0.0173 (8)
H18A	0.4984	0.4405	0.048	0.021*
C19B	0.2465 (3)	0.4503 (3)	0.5305 (2)	0.0242 (9)
H19B	0.302	0.4927	0.5306	0.029*
C6A	0.0553 (3)	0.3375 (3)	−0.0502 (2)	0.0279 (10)
H6A	0.0382	0.3337	−0.0977	0.033*
C1A	0.2318 (3)	0.2083 (2)	0.0850 (2)	0.0159 (8)
H1A1	0.1954	0.1499	0.0939	0.019*
H1A2	0.2894	0.1953	0.0531	0.019*
C13B	0.1290 (3)	−0.0456 (3)	0.4143 (2)	0.0211 (9)
H13B	0.1623	−0.1022	0.4048	0.025*
C10B	0.0285 (3)	0.1225 (2)	0.44585 (19)	0.0143 (7)
C18B	0.2053 (3)	0.4181 (3)	0.5926 (2)	0.0231 (9)
H18B	0.2331	0.4392	0.6349	0.028*
C9A	0.2468 (3)	0.1974 (2)	0.21582 (19)	0.0148 (8)
H9A	0.1736	0.1766	0.2121	0.018*
C8B	−0.0167 (3)	0.2854 (2)	0.4040 (2)	0.0184 (8)
H8B	−0.0311	0.2556	0.3585	0.022*
C20B	0.2038 (3)	0.4185 (2)	0.4669 (2)	0.0190 (8)
H20B	0.2302	0.4405	0.4244	0.023*
C21A	0.3903 (3)	0.3462 (2)	0.21365 (19)	0.0138 (8)
C15A	0.4194 (3)	0.1085 (3)	0.2206 (2)	0.0197 (8)
H15A	0.4522	0.1588	0.1986	0.024*
O21A	0.1778 (3)	0.2291 (3)	−0.13132 (18)	0.0549 (11)
C12A	0.3238 (3)	−0.0421 (3)	0.2855 (2)	0.0253 (9)
H12A	0.2911	−0.0926	0.3073	0.03*
C12B	0.0268 (3)	−0.0320 (3)	0.39325 (19)	0.0186 (8)
H12B	−0.0085	−0.0787	0.3686	0.022*
C17A	0.3930 (3)	0.3493 (2)	0.0882 (2)	0.0161 (8)
H17A	0.3675	0.3288	0.045	0.019*
C16B	0.0804 (3)	0.3195 (2)	0.5305 (2)	0.0150 (8)
C6B	−0.2018 (3)	0.3512 (3)	0.7354 (2)	0.0246 (9)
H6B	−0.213	0.3481	0.7837	0.03*
C7B	−0.1375 (3)	0.2867 (3)	0.7026 (2)	0.0180 (8)
C3A	0.1106 (3)	0.3480 (3)	0.0891 (2)	0.0203 (8)
H3A	0.1288	0.3538	0.1363	0.024*
C1B	−0.0440 (3)	0.2183 (2)	0.5937 (2)	0.0184 (8)
H1B1	0.013	0.2008	0.6249	0.022*
H1B2	−0.0838	0.1621	0.583	0.022*
C17B	0.1231 (3)	0.3546 (3)	0.5934 (2)	0.0190 (8)
H17B	0.0956	0.3349	0.6363	0.023*
C19A	0.5096 (3)	0.4480 (2)	0.1537 (2)	0.0196 (8)
H19A	0.5626	0.4928	0.1551	0.023*
C2B	−0.1151 (3)	0.2880 (2)	0.6311 (2)	0.0149 (8)
C7A	0.1272 (3)	0.2745 (3)	−0.0214 (2)	0.0193 (8)
C5A	0.0100 (3)	0.4046 (3)	−0.0091 (2)	0.0309 (10)
H5A	−0.0396	0.4454	−0.0279	0.037*
C4B	−0.2285 (3)	0.4243 (3)	0.6249 (2)	0.0237 (9)
H4B	−0.2596	0.4709	0.5978	0.028*
C2A	0.1559 (3)	0.2770 (2)	0.0497 (2)	0.0157 (8)
C15B	0.1323 (3)	0.1074 (3)	0.4654 (2)	0.0201 (8)
H15B	0.1686	0.1539	0.4896	0.024*
C21B	0.1224 (3)	0.3544 (3)	0.4673 (2)	0.0166 (8)
C11A	0.2657 (3)	0.0354 (3)	0.2666 (2)	0.0199 (8)
H11A	0.194	0.0365	0.2759	0.024*
C3B	−0.1625 (3)	0.3602 (3)	0.5934 (2)	0.0199 (8)
H3B	−0.1491	0.3654	0.5454	0.024*
C14B	0.1824 (3)	0.0243 (3)	0.4494 (2)	0.0228 (9)
H14B	0.2521	0.0154	0.4624	0.027*
C9B	−0.0301 (3)	0.2126 (3)	0.46218 (19)	0.0163 (8)
H9B	−0.1051	0.1973	0.465	0.02*
C11B	−0.0240 (3)	0.0526 (2)	0.40908 (19)	0.0177 (8)
H11B	−0.0931	0.0619	0.3949	0.021*

	U11	U22	U33	U12	U13	U23
O1A	0.0165 (14)	0.0217 (13)	0.0126 (13)	−0.0024 (10)	−0.0029 (11)	−0.0010 (11)
O1B	0.0179 (14)	0.0223 (13)	0.0162 (14)	−0.0010 (11)	−0.0002 (11)	−0.0038 (10)
O2B	0.0200 (15)	0.0231 (14)	0.0240 (15)	0.0070 (11)	−0.0034 (12)	0.0018 (11)
O2A	0.0266 (16)	0.0328 (15)	0.0277 (17)	0.0095 (13)	0.0048 (13)	0.0000 (13)
O22B	0.065 (2)	0.0267 (16)	0.0185 (18)	0.0054 (15)	−0.0077 (15)	−0.0012 (13)
O21B	0.063 (2)	0.0168 (15)	0.0258 (17)	0.0039 (13)	0.0028 (16)	−0.0007 (12)
O22A	0.049 (2)	0.0251 (16)	0.0287 (17)	0.0089 (14)	−0.0047 (15)	−0.0047 (13)
C20A	0.0142 (18)	0.0158 (17)	0.0170 (19)	0.0008 (15)	−0.0041 (15)	−0.0056 (15)
N1A	0.0174 (16)	0.0162 (15)	0.0132 (16)	−0.0016 (13)	−0.0005 (13)	0.0023 (12)
N1B	0.0185 (16)	0.0180 (15)	0.0107 (16)	−0.0047 (13)	−0.0003 (13)	−0.0038 (13)
N2B	0.029 (2)	0.0204 (18)	0.0195 (19)	−0.0011 (14)	0.0045 (15)	0.0010 (14)
C16A	0.0096 (18)	0.0136 (17)	0.020 (2)	0.0007 (14)	−0.0004 (15)	−0.0009 (14)
C8A	0.0119 (17)	0.0217 (18)	0.017 (2)	0.0025 (14)	0.0003 (15)	0.0050 (15)
C10A	0.0170 (19)	0.0183 (18)	0.0100 (18)	0.0005 (15)	0.0015 (15)	−0.0036 (14)
C4A	0.024 (2)	0.028 (2)	0.032 (2)	0.0089 (19)	0.0022 (18)	−0.0013 (18)
C5B	0.021 (2)	0.029 (2)	0.033 (2)	0.0070 (18)	0.0082 (18)	−0.0042 (18)
N2A	0.036 (2)	0.0277 (19)	0.016 (2)	0.0025 (16)	−0.0012 (16)	0.0003 (14)
C13A	0.030 (2)	0.0200 (19)	0.017 (2)	0.0072 (16)	0.0006 (17)	−0.0013 (15)
C14A	0.0176 (19)	0.0186 (19)	0.030 (2)	0.0043 (15)	0.0035 (17)	−0.0020 (16)
C18A	0.0161 (19)	0.0146 (18)	0.021 (2)	0.0003 (16)	0.0007 (16)	0.0043 (15)
C19B	0.0126 (19)	0.0184 (19)	0.042 (3)	−0.0017 (15)	−0.0027 (18)	−0.0051 (18)
C6A	0.031 (2)	0.035 (2)	0.017 (2)	−0.0023 (19)	−0.0083 (19)	0.0076 (17)
C1A	0.0109 (18)	0.0176 (19)	0.019 (2)	−0.0025 (14)	−0.0031 (16)	−0.0023 (15)
C13B	0.033 (2)	0.0149 (18)	0.0155 (19)	0.0057 (16)	0.0098 (18)	−0.0005 (14)
C10B	0.0158 (18)	0.0165 (17)	0.0107 (18)	−0.0038 (14)	0.0017 (15)	0.0011 (14)
C18B	0.018 (2)	0.021 (2)	0.031 (2)	0.0032 (17)	−0.0048 (18)	−0.0104 (17)
C9A	0.0119 (18)	0.0184 (18)	0.0140 (19)	−0.0021 (14)	0.0011 (15)	0.0037 (14)
C8B	0.0165 (19)	0.0211 (19)	0.018 (2)	0.0013 (15)	−0.0035 (16)	−0.0037 (15)
C20B	0.0143 (19)	0.0160 (19)	0.027 (2)	0.0021 (15)	0.0031 (16)	0.0010 (16)
C21A	0.0116 (17)	0.0175 (19)	0.0122 (19)	0.0048 (14)	−0.0011 (15)	0.0021 (14)
C15A	0.019 (2)	0.0181 (19)	0.022 (2)	0.0004 (15)	0.0054 (17)	0.0004 (16)
O21A	0.085 (3)	0.058 (2)	0.022 (2)	0.031 (2)	0.0133 (19)	0.0036 (16)
C12A	0.030 (2)	0.0213 (19)	0.024 (2)	−0.0002 (17)	0.0033 (19)	0.0067 (17)
C12B	0.025 (2)	0.0182 (18)	0.0129 (19)	−0.0037 (15)	0.0028 (16)	−0.0066 (14)
C17A	0.0142 (19)	0.0178 (19)	0.0162 (19)	0.0020 (15)	−0.0026 (16)	0.0007 (15)
C16B	0.0121 (18)	0.0182 (18)	0.0148 (19)	0.0053 (15)	−0.0020 (15)	−0.0042 (14)
C6B	0.026 (2)	0.031 (2)	0.017 (2)	−0.0018 (18)	0.0058 (17)	0.0006 (16)
C7B	0.0161 (19)	0.017 (2)	0.021 (2)	−0.0041 (15)	0.0012 (16)	0.0028 (15)
C3A	0.019 (2)	0.023 (2)	0.020 (2)	0.0020 (16)	−0.0004 (17)	−0.0026 (16)
C1B	0.021 (2)	0.0147 (18)	0.020 (2)	−0.0007 (16)	−0.0014 (17)	−0.0009 (15)
C17B	0.018 (2)	0.021 (2)	0.018 (2)	0.0023 (16)	−0.0016 (16)	−0.0041 (15)
C19A	0.0130 (18)	0.0157 (18)	0.030 (2)	−0.0009 (15)	−0.0030 (17)	0.0003 (16)
C2B	0.0112 (18)	0.0133 (17)	0.020 (2)	−0.0040 (14)	0.0000 (15)	−0.0005 (14)
C7A	0.022 (2)	0.020 (2)	0.015 (2)	−0.0036 (15)	−0.0007 (16)	0.0013 (15)
C5A	0.024 (2)	0.035 (2)	0.034 (3)	0.013 (2)	−0.0023 (19)	0.0071 (19)
C4B	0.017 (2)	0.024 (2)	0.030 (2)	0.0067 (17)	−0.0015 (17)	0.0034 (17)
C2A	0.0142 (18)	0.0144 (18)	0.019 (2)	−0.0053 (15)	−0.0010 (15)	0.0039 (14)
C15B	0.018 (2)	0.020 (2)	0.022 (2)	0.0006 (16)	−0.0007 (16)	−0.0030 (16)
C21B	0.015 (2)	0.0167 (19)	0.018 (2)	0.0022 (15)	0.0002 (16)	−0.0049 (15)
C11A	0.015 (2)	0.027 (2)	0.017 (2)	−0.0021 (16)	0.0008 (15)	0.0062 (15)
C3B	0.018 (2)	0.023 (2)	0.018 (2)	0.0012 (16)	−0.0009 (16)	0.0009 (16)
C14B	0.018 (2)	0.027 (2)	0.022 (2)	0.0055 (16)	−0.0006 (17)	0.0008 (17)
C9B	0.0094 (18)	0.025 (2)	0.014 (2)	−0.0016 (15)	−0.0006 (15)	−0.0039 (15)
C11B	0.0180 (19)	0.0220 (19)	0.0130 (19)	−0.0021 (15)	0.0006 (16)	−0.0012 (15)

O1A—C21A	1.389 (4)	C6A—C7A	1.395 (6)
O1A—C8A	1.432 (4)	C6A—H6A	0.93
O1B—C21B	1.379 (5)	C1A—C2A	1.532 (5)
O1B—C8B	1.426 (4)	C1A—H1A1	0.97
O2B—C8B	1.402 (4)	C1A—H1A2	0.97
O2B—H2B	0.82	C13B—C12B	1.375 (6)
O2A—C8A	1.391 (4)	C13B—C14B	1.380 (6)
O2A—H2A	0.82	C13B—H13B	0.93
O22B—N2B	1.229 (5)	C10B—C11B	1.390 (5)
O21B—N2B	1.215 (4)	C10B—C15B	1.390 (5)
O22A—N2A	1.207 (4)	C10B—C9B	1.519 (5)
C20A—C21A	1.376 (5)	C18B—C17B	1.385 (6)
C20A—C19A	1.380 (6)	C18B—H18B	0.93
C20A—H20A	0.93	C9A—H9A	0.98
N1A—C16A	1.393 (4)	C8B—C9B	1.527 (5)
N1A—C1A	1.434 (5)	C8B—H8B	0.98
N1A—C9A	1.451 (5)	C20B—C21B	1.382 (5)
N1B—C16B	1.372 (5)	C20B—H20B	0.93
N1B—C1B	1.455 (5)	C15A—H15A	0.93
N1B—C9B	1.459 (5)	C12A—C11A	1.379 (5)
N2B—C7B	1.467 (5)	C12A—H12A	0.93
C16A—C21A	1.393 (5)	C12B—C11B	1.403 (5)
C16A—C17A	1.401 (5)	C12B—H12B	0.93
C8A—C9A	1.524 (5)	C17A—H17A	0.93
C8A—H8A	0.98	C16B—C17B	1.406 (5)
C10A—C15A	1.389 (5)	C16B—C21B	1.407 (5)
C10A—C11A	1.392 (5)	C6B—C7B	1.381 (6)
C10A—C9A	1.516 (5)	C6B—H6B	0.93
C4A—C5A	1.375 (6)	C7B—C2B	1.389 (6)
C4A—C3A	1.393 (6)	C3A—C2A	1.386 (5)
C4A—H4A	0.93	C3A—H3A	0.93
C5B—C6B	1.375 (6)	C1B—C2B	1.522 (5)
C5B—C4B	1.376 (6)	C1B—H1B1	0.97
C5B—H5B	0.93	C1B—H1B2	0.97
N2A—O21A	1.224 (5)	C17B—H17B	0.93
N2A—C7A	1.443 (5)	C19A—H19A	0.93
C13A—C12A	1.378 (6)	C2B—C3B	1.393 (5)
C13A—C14A	1.386 (5)	C7A—C2A	1.401 (6)
C13A—H13A	0.93	C5A—H5A	0.93
C14A—C15A	1.390 (5)	C4B—C3B	1.378 (6)
C14A—H14A	0.93	C4B—H4B	0.93
C18A—C19A	1.384 (6)	C15B—C14B	1.381 (5)
C18A—C17A	1.386 (5)	C15B—H15B	0.93
C18A—H18A	0.93	C11A—H11A	0.93
C19B—C18B	1.370 (6)	C3B—H3B	0.93
C19B—C20B	1.401 (6)	C14B—H14B	0.93
C19B—H19B	0.93	C9B—H9B	0.98
C6A—C5A	1.363 (6)	C11B—H11B	0.93
C21A—O1A—C8A	115.6 (3)	C21B—C20B—H20B	119.9
C21B—O1B—C8B	114.3 (3)	C19B—C20B—H20B	119.9
C8B—O2B—H2B	109.5	C20A—C21A—O1A	117.8 (3)
C8A—O2A—H2A	109.5	C20A—C21A—C16A	121.6 (3)
C21A—C20A—C19A	120.3 (3)	O1A—C21A—C16A	120.6 (3)
C21A—C20A—H20A	119.8	C10A—C15A—C14A	120.7 (4)
C19A—C20A—H20A	119.8	C10A—C15A—H15A	119.6
C16A—N1A—C1A	120.6 (3)	C14A—C15A—H15A	119.6
C16A—N1A—C9A	118.7 (3)	C13A—C12A—C11A	120.3 (4)
C1A—N1A—C9A	119.9 (3)	C13A—C12A—H12A	119.9
C16B—N1B—C1B	120.7 (3)	C11A—C12A—H12A	119.9
C16B—N1B—C9B	119.7 (3)	C13B—C12B—C11B	119.7 (3)
C1B—N1B—C9B	118.6 (3)	C13B—C12B—H12B	120.2
O21B—N2B—O22B	123.6 (4)	C11B—C12B—H12B	120.2
O21B—N2B—C7B	119.0 (3)	C18A—C17A—C16A	121.4 (4)
O22B—N2B—C7B	117.4 (3)	C18A—C17A—H17A	119.3
N1A—C16A—C21A	120.3 (3)	C16A—C17A—H17A	119.3
N1A—C16A—C17A	122.5 (3)	N1B—C16B—C17B	123.1 (3)
C21A—C16A—C17A	117.2 (3)	N1B—C16B—C21B	120.0 (3)
O2A—C8A—O1A	110.0 (3)	C17B—C16B—C21B	116.9 (3)
O2A—C8A—C9A	109.8 (3)	C5B—C6B—C7B	119.2 (4)
O1A—C8A—C9A	110.4 (3)	C5B—C6B—H6B	120.4
O2A—C8A—H8A	108.9	C7B—C6B—H6B	120.4
O1A—C8A—H8A	108.9	C6B—C7B—C2B	123.7 (4)
C9A—C8A—H8A	108.9	C6B—C7B—N2B	115.8 (3)
C15A—C10A—C11A	118.1 (3)	C2B—C7B—N2B	120.5 (3)
C15A—C10A—C9A	122.0 (3)	C2A—C3A—C4A	122.2 (4)
C11A—C10A—C9A	119.9 (3)	C2A—C3A—H3A	118.9
C5A—C4A—C3A	120.6 (4)	C4A—C3A—H3A	118.9
C5A—C4A—H4A	119.7	N1B—C1B—C2B	112.4 (3)
C3A—C4A—H4A	119.7	N1B—C1B—H1B1	109.1
C6B—C5B—C4B	119.1 (4)	C2B—C1B—H1B1	109.1
C6B—C5B—H5B	120.5	N1B—C1B—H1B2	109.1
C4B—C5B—H5B	120.5	C2B—C1B—H1B2	109.1
O22A—N2A—O21A	123.4 (4)	H1B1—C1B—H1B2	107.9
O22A—N2A—C7A	119.3 (3)	C18B—C17B—C16B	121.1 (4)
O21A—N2A—C7A	117.2 (3)	C18B—C17B—H17B	119.5
C12A—C13A—C14A	119.4 (4)	C16B—C17B—H17B	119.5
C12A—C13A—H13A	120.3	C20A—C19A—C18A	119.7 (3)
C14A—C13A—H13A	120.3	C20A—C19A—H19A	120.2
C13A—C14A—C15A	120.2 (4)	C18A—C19A—H19A	120.2
C13A—C14A—H14A	119.9	C7B—C2B—C3B	115.1 (3)
C15A—C14A—H14A	119.9	C7B—C2B—C1B	124.7 (3)
C19A—C18A—C17A	119.8 (4)	C3B—C2B—C1B	120.1 (4)
C19A—C18A—H18A	120.1	C6A—C7A—C2A	122.2 (4)
C17A—C18A—H18A	120.1	C6A—C7A—N2A	116.4 (4)
C18B—C19B—C20B	119.0 (4)	C2A—C7A—N2A	121.4 (3)
C18B—C19B—H19B	120.5	C6A—C5A—C4A	118.9 (4)
C20B—C19B—H19B	120.5	C6A—C5A—H5A	120.6
C5A—C6A—C7A	120.5 (4)	C4A—C5A—H5A	120.6
C5A—C6A—H6A	119.8	C5B—C4B—C3B	120.7 (4)
C7A—C6A—H6A	119.8	C5B—C4B—H4B	119.6
N1A—C1A—C2A	112.9 (3)	C3B—C4B—H4B	119.6
N1A—C1A—H1A1	109	C3A—C2A—C7A	115.6 (4)
C2A—C1A—H1A1	109	C3A—C2A—C1A	119.6 (3)
N1A—C1A—H1A2	109	C7A—C2A—C1A	124.8 (3)
C2A—C1A—H1A2	109	C14B—C15B—C10B	120.9 (4)
H1A1—C1A—H1A2	107.8	C14B—C15B—H15B	119.5
C12B—C13B—C14B	120.3 (3)	C10B—C15B—H15B	119.5
C12B—C13B—H13B	119.8	O1B—C21B—C20B	117.4 (3)
C14B—C13B—H13B	119.8	O1B—C21B—C16B	121.0 (3)
C11B—C10B—C15B	118.7 (3)	C20B—C21B—C16B	121.6 (4)
C11B—C10B—C9B	118.3 (3)	C12A—C11A—C10A	121.3 (4)
C15B—C10B—C9B	123.0 (3)	C12A—C11A—H11A	119.4
C19B—C18B—C17B	121.3 (4)	C10A—C11A—H11A	119.4
C19B—C18B—H18B	119.4	C4B—C3B—C2B	122.1 (4)
C17B—C18B—H18B	119.4	C4B—C3B—H3B	118.9
N1A—C9A—C10A	115.4 (3)	C2B—C3B—H3B	118.9
N1A—C9A—C8A	109.0 (3)	C13B—C14B—C15B	120.0 (4)
C10A—C9A—C8A	110.3 (3)	C13B—C14B—H14B	120
N1A—C9A—H9A	107.3	C15B—C14B—H14B	120
C10A—C9A—H9A	107.3	N1B—C9B—C10B	114.1 (3)
C8A—C9A—H9A	107.3	N1B—C9B—C8B	108.1 (3)
O2B—C8B—O1B	110.8 (3)	C10B—C9B—C8B	111.9 (3)
O2B—C8B—C9B	108.4 (3)	N1B—C9B—H9B	107.5
O1B—C8B—C9B	111.2 (3)	C10B—C9B—H9B	107.5
O2B—C8B—H8B	108.8	C8B—C9B—H9B	107.5
O1B—C8B—H8B	108.8	C10B—C11B—C12B	120.3 (3)
C9B—C8B—H8B	108.8	C10B—C11B—H11B	119.8
C21B—C20B—C19B	120.1 (4)	C12B—C11B—H11B	119.8
C1A—N1A—C16A—C21A	178.9 (3)	C21A—C20A—C19A—C18A	0.1 (5)
C9A—N1A—C16A—C21A	−10.7 (5)	C17A—C18A—C19A—C20A	−0.5 (5)
C1A—N1A—C16A—C17A	−0.1 (5)	C6B—C7B—C2B—C3B	0.0 (5)
C9A—N1A—C16A—C17A	170.3 (3)	N2B—C7B—C2B—C3B	−179.8 (3)
C21A—O1A—C8A—O2A	−71.7 (4)	C6B—C7B—C2B—C1B	179.6 (4)
C21A—O1A—C8A—C9A	49.7 (4)	N2B—C7B—C2B—C1B	−0.2 (6)
C12A—C13A—C14A—C15A	−0.3 (6)	N1B—C1B—C2B—C7B	−156.3 (3)
C16A—N1A—C1A—C2A	−75.7 (4)	N1B—C1B—C2B—C3B	23.2 (5)
C9A—N1A—C1A—C2A	114.0 (3)	C5A—C6A—C7A—C2A	0.0 (6)
C20B—C19B—C18B—C17B	0.3 (6)	C5A—C6A—C7A—N2A	−179.2 (4)
C16A—N1A—C9A—C10A	−87.3 (4)	O22A—N2A—C7A—C6A	−151.1 (4)
C1A—N1A—C9A—C10A	83.1 (4)	O21A—N2A—C7A—C6A	27.3 (6)
C16A—N1A—C9A—C8A	37.4 (4)	O22A—N2A—C7A—C2A	29.7 (6)
C1A—N1A—C9A—C8A	−152.2 (3)	O21A—N2A—C7A—C2A	−151.9 (4)
C15A—C10A—C9A—N1A	38.8 (5)	C7A—C6A—C5A—C4A	2.0 (7)
C11A—C10A—C9A—N1A	−142.9 (3)	C3A—C4A—C5A—C6A	−2.1 (7)
C15A—C10A—C9A—C8A	−85.3 (4)	C6B—C5B—C4B—C3B	0.6 (7)
C11A—C10A—C9A—C8A	93.0 (4)	C4A—C3A—C2A—C7A	1.9 (6)
O2A—C8A—C9A—N1A	65.3 (4)	C4A—C3A—C2A—C1A	−178.2 (4)
O1A—C8A—C9A—N1A	−56.1 (4)	C6A—C7A—C2A—C3A	−1.9 (6)
O2A—C8A—C9A—C10A	−167.0 (3)	N2A—C7A—C2A—C3A	177.3 (3)
O1A—C8A—C9A—C10A	71.5 (4)	C6A—C7A—C2A—C1A	178.1 (4)
C21B—O1B—C8B—O2B	68.7 (4)	N2A—C7A—C2A—C1A	−2.7 (6)
C21B—O1B—C8B—C9B	−51.9 (4)	N1A—C1A—C2A—C3A	−19.0 (5)
C18B—C19B—C20B—C21B	−1.0 (5)	N1A—C1A—C2A—C7A	161.0 (3)
C19A—C20A—C21A—O1A	179.0 (3)	C11B—C10B—C15B—C14B	−0.7 (6)
C19A—C20A—C21A—C16A	1.3 (5)	C9B—C10B—C15B—C14B	180.0 (4)
C8A—O1A—C21A—C20A	159.9 (3)	C8B—O1B—C21B—C20B	−158.0 (3)
C8A—O1A—C21A—C16A	−22.3 (4)	C8B—O1B—C21B—C16B	25.5 (5)
N1A—C16A—C21A—C20A	178.9 (3)	C19B—C20B—C21B—O1B	−176.5 (3)
C17A—C16A—C21A—C20A	−2.1 (5)	C19B—C20B—C21B—C16B	0.0 (5)
N1A—C16A—C21A—O1A	1.2 (5)	N1B—C16B—C21B—O1B	−3.5 (5)
C17A—C16A—C21A—O1A	−179.7 (3)	C17B—C16B—C21B—O1B	178.0 (3)
C11A—C10A—C15A—C14A	−0.4 (6)	N1B—C16B—C21B—C20B	−179.9 (3)
C9A—C10A—C15A—C14A	178.0 (3)	C17B—C16B—C21B—C20B	1.6 (5)
C13A—C14A—C15A—C10A	0.4 (6)	C13A—C12A—C11A—C10A	0.0 (6)
C14A—C13A—C12A—C11A	0.1 (6)	C15A—C10A—C11A—C12A	0.2 (6)
C14B—C13B—C12B—C11B	−1.4 (6)	C9A—C10A—C11A—C12A	−178.2 (4)
C19A—C18A—C17A—C16A	−0.4 (5)	C5B—C4B—C3B—C2B	1.0 (6)
N1A—C16A—C17A—C18A	−179.3 (3)	C7B—C2B—C3B—C4B	−1.3 (5)
C21A—C16A—C17A—C18A	1.7 (5)	C1B—C2B—C3B—C4B	179.1 (4)
C1B—N1B—C16B—C17B	−2.3 (5)	C12B—C13B—C14B—C15B	1.8 (6)
C9B—N1B—C16B—C17B	−171.1 (3)	C10B—C15B—C14B—C13B	−0.8 (6)
C1B—N1B—C16B—C21B	179.3 (3)	C16B—N1B—C9B—C10B	89.6 (4)
C9B—N1B—C16B—C21B	10.4 (5)	C1B—N1B—C9B—C10B	−79.4 (4)
C4B—C5B—C6B—C7B	−1.8 (6)	C16B—N1B—C9B—C8B	−35.5 (4)
C5B—C6B—C7B—C2B	1.5 (6)	C1B—N1B—C9B—C8B	155.4 (3)
C5B—C6B—C7B—N2B	−178.7 (4)	C11B—C10B—C9B—N1B	146.7 (3)
O21B—N2B—C7B—C6B	145.4 (4)	C15B—C10B—C9B—N1B	−33.9 (5)
O22B—N2B—C7B—C6B	−33.2 (5)	C11B—C10B—C9B—C8B	−90.2 (4)
O21B—N2B—C7B—C2B	−34.8 (5)	C15B—C10B—C9B—C8B	89.2 (4)
O22B—N2B—C7B—C2B	146.6 (4)	O2B—C8B—C9B—N1B	−66.3 (4)
C5A—C4A—C3A—C2A	0.0 (7)	O1B—C8B—C9B—N1B	55.8 (4)
C16B—N1B—C1B—C2B	75.9 (4)	O2B—C8B—C9B—C10B	167.3 (3)
C9B—N1B—C1B—C2B	−115.1 (3)	O1B—C8B—C9B—C10B	−70.7 (4)
C19B—C18B—C17B—C16B	1.4 (6)	C15B—C10B—C11B—C12B	1.0 (5)
N1B—C16B—C17B—C18B	179.3 (3)	C9B—C10B—C11B—C12B	−179.5 (3)
C21B—C16B—C17B—C18B	−2.3 (5)	C13B—C12B—C11B—C10B	0.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O2A—H2A···O1B	0.82	2.06	2.843 (4)	161
C6B—H6B···O21Ai	0.93	2.40	3.175 (5)	141
C8B—H8B···O1Aii	0.98	2.34	3.234 (4)	151
C14A—H14A···O2Aiii	0.93	2.57	3.177 (5)	123
C19A—H19A···O21Biv	0.93	2.45	3.134 (4)	131
C19B—H19B···O22Av	0.93	2.47	3.057 (5)	121
O2B—H2B···Cg1ii	0.82	2.69	3.484 (3)	164
C18A—H18A···Cg2iv	0.93	2.83	3.564 (4)	137
C18B—H18B···Cg1v	0.93	2.94	3.601 (4)	130

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the controids of the C10A–C15A and C10B–C15B rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2A—H2A⋯O1B	0.82	2.06	2.843 (4)	161
C6B—H6B⋯O21A i	0.93	2.40	3.175 (5)	141
C8B—H8B⋯O1A ii	0.98	2.34	3.234 (4)	151
C14A—H14A⋯O2A iii	0.93	2.57	3.177 (5)	123
C19A—H19A⋯O21B iv	0.93	2.45	3.134 (4)	131
C19B—H19B⋯O22A v	0.93	2.47	3.057 (5)	121
O2B—H2B⋯Cg1ii	0.82	2.69	3.484 (3)	164
C18A—H18A⋯Cg2iv	0.93	2.83	3.564 (4)	137
C18B—H18B⋯Cg1v	0.93	2.94	3.601 (4)	130

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