N-Benzoyl-N-(1,4-dioxonaphthalen-2-yl)benzamide.

The title mol-ecule, C(24)H(15)NO(4), crystallizes with two mol-ecules in the asymmetric unit (Z' = 2). For both mol-ecules, the two amide groups are not coplanar, as the dihedral angles of the respective NCO groups are similar at 50.37 (14) and 51.22 (13)°. However, the orientations of the substituent phenyl rings with the central naphthalene system are significantly different for the two mol-ecules; for one mol-ecule, these dihedral angles are 80.29 (3) and 80.95 (4)°, while for the second mol-ecule they are 86.63 (3) and 72.82 (4)°. The crystal packing shows the mol-ecules to be linked by weak C-H⋯O inter-actions.

Related literature

For related structures, see: Akinboye, Butcher, Brandy et al. (2009 ▶); Akinboye, Butcher, Wright et al. (2009 ▶). For pharmacological properties of related compounds, see: Bakare et al. (2003 ▶); Khraiwesh et al. (2011 ▶); Berhe et al. (2008 ▶).

Experimental

Crystal data

C24H15NO4

M = 381.37

Triclinic,

a = 9.8704 (11) Å

b = 12.6776 (11) Å

c = 15.6472 (14) Å

α = 90.735 (7)°

β = 98.213 (9)°

γ = 108.187 (9)°

V = 1837.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 123 K

0.52 × 0.28 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 ▶) T min = 0.751, T max = 1.000

26547 measured reflections

26547 independent reflections

17970 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.221

S = 1.03

26547 reflections

524 parameters

H-atom parameters constrained

Δρmax = 0.70 e Å−3

Δρmin = −0.43 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812030231/jj2146sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030231/jj2146Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812030231/jj2146Isup3.cml

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

C24H15NO4	Z = 4
Mr = 381.37	F(000) = 792
Triclinic, P1	Dx = 1.378 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8704 (11) Å	Cell parameters from 3142 reflections
b = 12.6776 (11) Å	θ = 3.0–34.9°
c = 15.6472 (14) Å	µ = 0.10 mm−1
α = 90.735 (7)°	T = 123 K
β = 98.213 (9)°	Block, colorless
γ = 108.187 (9)°	0.52 × 0.28 × 0.15 mm
V = 1837.6 (3) Å3

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	26547 independent reflections
Radiation source: Enhance (Mo) X-ray Source	17970 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
Detector resolution: 10.5081 pixels mm-1	θmax = 35.2°, θmin = 3.1°
ω scans	h = −15→15
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −20→20
Tmin = 0.751, Tmax = 1.000	l = −24→21
26547 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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.221	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.1412P)2] where P = (Fo2 + 2Fc2)/3
26547 reflections	(Δ/σ)max = 0.001
524 parameters	Δρmax = 0.70 e Å−3
0 restraints	Δρmin = −0.43 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	0.61934 (11)	0.65075 (8)	1.11669 (6)	0.0244 (2)
O2A	0.15230 (10)	0.64038 (8)	0.89442 (6)	0.02104 (19)
O3A	0.50651 (10)	1.01393 (8)	0.90297 (6)	0.02088 (19)
O4A	0.18605 (11)	0.84042 (8)	1.00964 (6)	0.02152 (19)
N1A	0.36272 (12)	0.84143 (9)	0.93028 (7)	0.0166 (2)
C1A	0.37834 (13)	0.74566 (10)	0.97147 (7)	0.0153 (2)
C2A	0.49758 (14)	0.74697 (10)	1.02443 (8)	0.0173 (2)
H2AA	0.5767	0.8139	1.0342	0.021*
C3A	0.50990 (14)	0.64715 (10)	1.06827 (8)	0.0173 (2)
C4A	0.38274 (13)	0.54455 (10)	1.05355 (7)	0.0160 (2)
C5A	0.38512 (15)	0.45054 (11)	1.09716 (9)	0.0209 (2)
H5AA	0.4686	0.4515	1.1362	0.025*
C6A	0.26582 (16)	0.35463 (11)	1.08401 (9)	0.0240 (3)
H6AA	0.2685	0.2902	1.1137	0.029*
C7A	0.14371 (16)	0.35298 (11)	1.02791 (9)	0.0230 (3)
H7AA	0.0620	0.2877	1.0195	0.028*
C8A	0.14043 (15)	0.44648 (11)	0.98398 (8)	0.0198 (2)
H8AA	0.0567	0.4450	0.9449	0.024*
C9A	0.25916 (14)	0.54244 (10)	0.99677 (7)	0.0158 (2)
C10A	0.25331 (13)	0.64191 (10)	0.94990 (7)	0.0155 (2)
C11A	0.47714 (14)	0.91402 (10)	0.89268 (7)	0.0165 (2)
C12A	0.55113 (14)	0.86068 (10)	0.83735 (8)	0.0166 (2)
C13A	0.47877 (15)	0.75844 (11)	0.79278 (8)	0.0187 (2)
H13A	0.3835	0.7184	0.8017	0.022*
C14A	0.54511 (16)	0.71467 (12)	0.73529 (8)	0.0226 (3)
H14A	0.4952	0.6450	0.7046	0.027*
C15A	0.68457 (17)	0.77295 (13)	0.72280 (8)	0.0251 (3)
H15A	0.7307	0.7429	0.6840	0.030*
C16A	0.75694 (16)	0.87551 (13)	0.76714 (9)	0.0253 (3)
H16A	0.8525	0.9152	0.7585	0.030*
C17A	0.69028 (15)	0.92022 (11)	0.82395 (8)	0.0207 (2)
H17A	0.7392	0.9908	0.8534	0.025*
C18A	0.24559 (14)	0.87524 (10)	0.94867 (8)	0.0169 (2)
C19A	0.19812 (14)	0.95011 (11)	0.88779 (9)	0.0206 (2)
C20A	0.20504 (17)	0.94166 (13)	0.79946 (9)	0.0271 (3)
H20A	0.2413	0.8876	0.7771	0.033*
C21A	0.15885 (19)	1.01249 (15)	0.74495 (11)	0.0367 (4)
H21A	0.1623	1.0066	0.6848	0.044*
C22A	0.10775 (19)	1.09162 (14)	0.77739 (13)	0.0410 (4)
H22A	0.0791	1.1415	0.7397	0.049*
C23A	0.09770 (19)	1.09917 (14)	0.86423 (13)	0.0389 (4)
H23A	0.0609	1.1532	0.8860	0.047*
C24A	0.14178 (16)	1.02722 (12)	0.91974 (10)	0.0268 (3)
H24A	0.1333	1.0309	0.9793	0.032*
O1B	0.60121 (11)	0.13107 (9)	0.39332 (6)	0.0239 (2)
O2B	0.18809 (11)	0.14122 (8)	0.57590 (6)	0.02112 (19)
O3B	0.53144 (11)	0.51594 (8)	0.59971 (6)	0.01961 (18)
O4B	0.18878 (11)	0.32712 (8)	0.45919 (6)	0.0232 (2)
N1B	0.38724 (11)	0.33871 (9)	0.55734 (6)	0.01598 (19)
C1B	0.39502 (13)	0.23977 (10)	0.51787 (7)	0.0149 (2)
C2B	0.50258 (14)	0.23682 (11)	0.47547 (8)	0.0181 (2)
H2BA	0.5809	0.3029	0.4738	0.022*
C3B	0.50210 (14)	0.13280 (11)	0.43110 (8)	0.0176 (2)
C4B	0.37397 (14)	0.03230 (10)	0.43147 (7)	0.0170 (2)
C5B	0.36221 (16)	−0.06502 (11)	0.38440 (8)	0.0216 (3)
H5BA	0.4353	−0.0670	0.3515	0.026*
C6B	0.24392 (16)	−0.15902 (12)	0.38559 (9)	0.0248 (3)
H6BA	0.2356	−0.2249	0.3528	0.030*
C7B	0.13726 (15)	−0.15763 (11)	0.43448 (9)	0.0242 (3)
H7BA	0.0570	−0.2226	0.4354	0.029*
C8B	0.14839 (15)	−0.06103 (11)	0.48195 (9)	0.0215 (2)
H8BA	0.0764	−0.0600	0.5160	0.026*
C9B	0.26546 (13)	0.03420 (10)	0.47945 (8)	0.0163 (2)
C10B	0.27458 (13)	0.13758 (10)	0.52801 (7)	0.0157 (2)
C11B	0.50716 (13)	0.41715 (10)	0.60839 (7)	0.0155 (2)
C12B	0.59360 (13)	0.37346 (10)	0.67570 (7)	0.0164 (2)
C13B	0.53263 (14)	0.27461 (11)	0.71402 (8)	0.0179 (2)
H13B	0.4363	0.2297	0.6932	0.021*
C14B	0.61293 (16)	0.24183 (12)	0.78280 (8)	0.0226 (3)
H14B	0.5723	0.1742	0.8088	0.027*
C15B	0.75295 (17)	0.30876 (13)	0.81313 (8)	0.0258 (3)
H15B	0.8081	0.2866	0.8601	0.031*
C16B	0.81343 (16)	0.40773 (13)	0.77565 (8)	0.0247 (3)
H16B	0.9095	0.4529	0.7968	0.030*
C17B	0.73313 (14)	0.44047 (11)	0.70715 (8)	0.0199 (2)
H17B	0.7736	0.5087	0.6818	0.024*
C18B	0.26274 (14)	0.36802 (10)	0.52716 (8)	0.0174 (2)
C19B	0.22434 (13)	0.44303 (10)	0.58654 (8)	0.0176 (2)
C20B	0.23316 (15)	0.42713 (11)	0.67508 (8)	0.0211 (2)
H20B	0.2701	0.3713	0.6990	0.025*
C21B	0.18735 (16)	0.49364 (13)	0.72766 (9)	0.0251 (3)
H21B	0.1918	0.4826	0.7878	0.030*
C22B	0.13520 (16)	0.57591 (13)	0.69353 (10)	0.0266 (3)
H22B	0.1049	0.6215	0.7303	0.032*
C23B	0.12693 (16)	0.59214 (12)	0.60551 (10)	0.0257 (3)
H23B	0.0923	0.6493	0.5821	0.031*
C24B	0.16968 (15)	0.52406 (11)	0.55198 (9)	0.0215 (3)
H24B	0.1613	0.5332	0.4915	0.026*

	U11	U22	U33	U12	U13	U23
O1A	0.0214 (5)	0.0244 (5)	0.0260 (5)	0.0075 (4)	−0.0014 (4)	0.0038 (4)
O2A	0.0221 (5)	0.0188 (4)	0.0199 (4)	0.0053 (4)	−0.0014 (3)	0.0022 (3)
O3A	0.0260 (5)	0.0144 (4)	0.0220 (4)	0.0050 (4)	0.0060 (4)	0.0017 (3)
O4A	0.0227 (5)	0.0232 (5)	0.0195 (4)	0.0068 (4)	0.0074 (3)	0.0027 (4)
N1A	0.0217 (5)	0.0134 (4)	0.0162 (4)	0.0065 (4)	0.0057 (4)	0.0035 (4)
C1A	0.0192 (6)	0.0133 (5)	0.0144 (5)	0.0052 (4)	0.0049 (4)	0.0027 (4)
C2A	0.0181 (6)	0.0146 (5)	0.0184 (5)	0.0036 (4)	0.0038 (4)	0.0004 (4)
C3A	0.0185 (6)	0.0174 (5)	0.0163 (5)	0.0056 (4)	0.0034 (4)	0.0007 (4)
C4A	0.0178 (5)	0.0156 (5)	0.0154 (5)	0.0060 (4)	0.0041 (4)	0.0022 (4)
C5A	0.0237 (6)	0.0189 (6)	0.0217 (6)	0.0089 (5)	0.0033 (5)	0.0047 (5)
C6A	0.0289 (7)	0.0163 (6)	0.0272 (6)	0.0067 (5)	0.0062 (5)	0.0085 (5)
C7A	0.0245 (7)	0.0149 (5)	0.0287 (7)	0.0036 (5)	0.0074 (5)	0.0034 (5)
C8A	0.0197 (6)	0.0171 (5)	0.0219 (6)	0.0054 (5)	0.0025 (4)	0.0007 (4)
C9A	0.0191 (6)	0.0141 (5)	0.0151 (5)	0.0060 (4)	0.0040 (4)	0.0011 (4)
C10A	0.0193 (6)	0.0139 (5)	0.0140 (5)	0.0060 (4)	0.0035 (4)	0.0007 (4)
C11A	0.0196 (6)	0.0161 (5)	0.0134 (5)	0.0052 (4)	0.0027 (4)	0.0022 (4)
C12A	0.0211 (6)	0.0157 (5)	0.0142 (5)	0.0069 (4)	0.0042 (4)	0.0027 (4)
C13A	0.0243 (6)	0.0175 (5)	0.0153 (5)	0.0073 (5)	0.0044 (4)	0.0017 (4)
C14A	0.0323 (7)	0.0227 (6)	0.0156 (5)	0.0127 (5)	0.0037 (5)	−0.0005 (5)
C15A	0.0330 (8)	0.0327 (7)	0.0180 (6)	0.0197 (6)	0.0094 (5)	0.0056 (5)
C16A	0.0239 (7)	0.0294 (7)	0.0258 (6)	0.0100 (6)	0.0106 (5)	0.0083 (5)
C17A	0.0222 (6)	0.0197 (6)	0.0205 (6)	0.0054 (5)	0.0064 (5)	0.0051 (5)
C18A	0.0198 (6)	0.0138 (5)	0.0170 (5)	0.0054 (4)	0.0025 (4)	0.0001 (4)
C19A	0.0194 (6)	0.0186 (6)	0.0239 (6)	0.0067 (5)	0.0023 (5)	0.0040 (5)
C20A	0.0285 (7)	0.0295 (7)	0.0232 (6)	0.0092 (6)	0.0032 (5)	0.0074 (5)
C21A	0.0333 (9)	0.0418 (9)	0.0315 (8)	0.0086 (7)	0.0001 (6)	0.0172 (7)
C22A	0.0337 (9)	0.0283 (8)	0.0546 (11)	0.0075 (7)	−0.0095 (8)	0.0182 (8)
C23A	0.0348 (9)	0.0237 (7)	0.0571 (11)	0.0149 (7)	−0.0085 (8)	0.0021 (7)
C24A	0.0244 (7)	0.0212 (6)	0.0355 (7)	0.0105 (5)	−0.0001 (6)	−0.0019 (6)
O1B	0.0253 (5)	0.0267 (5)	0.0251 (5)	0.0130 (4)	0.0103 (4)	0.0033 (4)
O2B	0.0216 (5)	0.0201 (4)	0.0223 (4)	0.0056 (4)	0.0079 (4)	−0.0004 (4)
O3B	0.0238 (5)	0.0150 (4)	0.0200 (4)	0.0059 (3)	0.0039 (3)	0.0006 (3)
O4B	0.0240 (5)	0.0264 (5)	0.0197 (4)	0.0112 (4)	−0.0021 (4)	−0.0034 (4)
N1B	0.0171 (5)	0.0149 (5)	0.0164 (4)	0.0062 (4)	0.0018 (4)	−0.0007 (4)
C1B	0.0176 (5)	0.0134 (5)	0.0146 (5)	0.0066 (4)	0.0015 (4)	0.0004 (4)
C2B	0.0198 (6)	0.0179 (5)	0.0178 (5)	0.0070 (5)	0.0047 (4)	0.0020 (4)
C3B	0.0201 (6)	0.0198 (6)	0.0161 (5)	0.0104 (5)	0.0038 (4)	0.0029 (4)
C4B	0.0213 (6)	0.0180 (5)	0.0144 (5)	0.0105 (5)	0.0012 (4)	0.0011 (4)
C5B	0.0271 (7)	0.0208 (6)	0.0199 (6)	0.0125 (5)	0.0025 (5)	−0.0024 (5)
C6B	0.0307 (7)	0.0189 (6)	0.0258 (6)	0.0116 (5)	−0.0004 (5)	−0.0050 (5)
C7B	0.0218 (6)	0.0157 (6)	0.0317 (7)	0.0040 (5)	−0.0021 (5)	−0.0029 (5)
C8B	0.0191 (6)	0.0183 (6)	0.0269 (6)	0.0066 (5)	0.0017 (5)	−0.0015 (5)
C9B	0.0177 (6)	0.0153 (5)	0.0169 (5)	0.0073 (4)	0.0007 (4)	−0.0002 (4)
C10B	0.0166 (5)	0.0154 (5)	0.0157 (5)	0.0061 (4)	0.0017 (4)	0.0004 (4)
C11B	0.0172 (5)	0.0167 (5)	0.0137 (5)	0.0063 (4)	0.0035 (4)	0.0001 (4)
C12B	0.0183 (6)	0.0184 (5)	0.0137 (5)	0.0073 (4)	0.0029 (4)	−0.0001 (4)
C13B	0.0212 (6)	0.0170 (5)	0.0157 (5)	0.0057 (4)	0.0042 (4)	0.0007 (4)
C14B	0.0344 (7)	0.0233 (6)	0.0149 (5)	0.0148 (6)	0.0066 (5)	0.0034 (5)
C15B	0.0326 (8)	0.0350 (8)	0.0153 (5)	0.0194 (6)	0.0017 (5)	0.0035 (5)
C16B	0.0233 (7)	0.0324 (7)	0.0184 (6)	0.0104 (6)	0.0000 (5)	0.0013 (5)
C17B	0.0203 (6)	0.0216 (6)	0.0171 (5)	0.0063 (5)	0.0018 (4)	0.0000 (4)
C18B	0.0172 (6)	0.0171 (5)	0.0192 (5)	0.0073 (4)	0.0025 (4)	0.0017 (4)
C19B	0.0159 (5)	0.0179 (5)	0.0200 (5)	0.0065 (4)	0.0029 (4)	−0.0016 (4)
C20B	0.0207 (6)	0.0225 (6)	0.0212 (6)	0.0079 (5)	0.0047 (5)	0.0007 (5)
C21B	0.0239 (7)	0.0299 (7)	0.0228 (6)	0.0088 (6)	0.0071 (5)	−0.0020 (5)
C22B	0.0228 (7)	0.0274 (7)	0.0308 (7)	0.0103 (5)	0.0045 (5)	−0.0098 (6)
C23B	0.0243 (7)	0.0239 (7)	0.0314 (7)	0.0134 (5)	−0.0001 (5)	−0.0030 (5)
C24B	0.0198 (6)	0.0228 (6)	0.0229 (6)	0.0097 (5)	−0.0001 (5)	−0.0003 (5)

O1A—C3A	1.2154 (16)	O1B—C3B	1.2188 (15)
O2A—C10A	1.2199 (15)	O2B—C10B	1.2243 (15)
O3A—C11A	1.2109 (15)	O3B—C11B	1.2127 (15)
O4A—C18A	1.2080 (15)	O4B—C18B	1.2086 (15)
N1A—C18A	1.4158 (16)	N1B—C18B	1.4125 (16)
N1A—C1A	1.4218 (15)	N1B—C11B	1.4152 (16)
N1A—C11A	1.4226 (16)	N1B—C1B	1.4192 (15)
C1A—C2A	1.3345 (17)	C1B—C2B	1.3395 (17)
C1A—C10A	1.4911 (18)	C1B—C10B	1.4882 (17)
C2A—C3A	1.4769 (18)	C2B—C3B	1.4807 (17)
C2A—H2AA	0.9500	C2B—H2BA	0.9500
C3A—C4A	1.4869 (18)	C3B—C4B	1.4897 (19)
C4A—C5A	1.3858 (17)	C4B—C5B	1.3933 (17)
C4A—C9A	1.3955 (17)	C4B—C9B	1.3988 (17)
C5A—C6A	1.392 (2)	C5B—C6B	1.386 (2)
C5A—H5AA	0.9500	C5B—H5BA	0.9500
C6A—C7A	1.380 (2)	C6B—C7B	1.391 (2)
C6A—H6AA	0.9500	C6B—H6BA	0.9500
C7A—C8A	1.3846 (18)	C7B—C8B	1.3903 (18)
C7A—H7AA	0.9500	C7B—H7BA	0.9500
C8A—C9A	1.3893 (18)	C8B—C9B	1.3920 (18)
C8A—H8AA	0.9500	C8B—H8BA	0.9500
C9A—C10A	1.4793 (17)	C9B—C10B	1.4780 (16)
C11A—C12A	1.4880 (17)	C11B—C12B	1.4824 (17)
C12A—C13A	1.3904 (18)	C12B—C17B	1.3877 (18)
C12A—C17A	1.3926 (18)	C12B—C13B	1.3942 (18)
C13A—C14A	1.3886 (18)	C13B—C14B	1.3901 (18)
C13A—H13A	0.9500	C13B—H13B	0.9500
C14A—C15A	1.387 (2)	C14B—C15B	1.388 (2)
C14A—H14A	0.9500	C14B—H14B	0.9500
C15A—C16A	1.392 (2)	C15B—C16B	1.388 (2)
C15A—H15A	0.9500	C15B—H15B	0.9500
C16A—C17A	1.3897 (18)	C16B—C17B	1.3869 (18)
C16A—H16A	0.9500	C16B—H16B	0.9500
C17A—H17A	0.9500	C17B—H17B	0.9500
C18A—C19A	1.4836 (18)	C18B—C19B	1.4881 (17)
C19A—C24A	1.3860 (19)	C19B—C24B	1.3841 (18)
C19A—C20A	1.398 (2)	C19B—C20B	1.3967 (18)
C20A—C21A	1.380 (2)	C20B—C21B	1.3852 (18)
C20A—H20A	0.9500	C20B—H20B	0.9500
C21A—C22A	1.376 (3)	C21B—C22B	1.382 (2)
C21A—H21A	0.9500	C21B—H21B	0.9500
C22A—C23A	1.381 (3)	C22B—C23B	1.390 (2)
C22A—H22A	0.9500	C22B—H22B	0.9500
C23A—C24A	1.391 (2)	C23B—C24B	1.3907 (19)
C23A—H23A	0.9500	C23B—H23B	0.9500
C24A—H24A	0.9500	C24B—H24B	0.9500
C18A—N1A—C1A	115.64 (10)	C18B—N1B—C11B	119.88 (10)
C18A—N1A—C11A	121.20 (10)	C18B—N1B—C1B	115.62 (10)
C1A—N1A—C11A	121.16 (11)	C11B—N1B—C1B	123.00 (10)
C2A—C1A—N1A	122.76 (11)	C2B—C1B—N1B	123.34 (11)
C2A—C1A—C10A	121.76 (11)	C2B—C1B—C10B	121.83 (11)
N1A—C1A—C10A	115.46 (11)	N1B—C1B—C10B	114.83 (10)
C1A—C2A—C3A	121.80 (11)	C1B—C2B—C3B	121.46 (12)
C1A—C2A—H2AA	119.1	C1B—C2B—H2BA	119.3
C3A—C2A—H2AA	119.1	C3B—C2B—H2BA	119.3
O1A—C3A—C2A	120.50 (12)	O1B—C3B—C2B	120.78 (12)
O1A—C3A—C4A	121.68 (12)	O1B—C3B—C4B	121.54 (12)
C2A—C3A—C4A	117.79 (11)	C2B—C3B—C4B	117.63 (11)
C5A—C4A—C9A	119.36 (12)	C5B—C4B—C9B	119.45 (12)
C5A—C4A—C3A	120.22 (11)	C5B—C4B—C3B	119.95 (12)
C9A—C4A—C3A	120.41 (11)	C9B—C4B—C3B	120.60 (11)
C4A—C5A—C6A	120.35 (13)	C6B—C5B—C4B	120.00 (13)
C4A—C5A—H5AA	119.8	C6B—C5B—H5BA	120.0
C6A—C5A—H5AA	119.8	C4B—C5B—H5BA	120.0
C7A—C6A—C5A	120.09 (12)	C5B—C6B—C7B	120.52 (12)
C7A—C6A—H6AA	120.0	C5B—C6B—H6BA	119.7
C5A—C6A—H6AA	120.0	C7B—C6B—H6BA	119.7
C6A—C7A—C8A	119.95 (13)	C8B—C7B—C6B	119.88 (13)
C6A—C7A—H7AA	120.0	C8B—C7B—H7BA	120.1
C8A—C7A—H7AA	120.0	C6B—C7B—H7BA	120.1
C7A—C8A—C9A	120.24 (13)	C7B—C8B—C9B	119.75 (13)
C7A—C8A—H8AA	119.9	C7B—C8B—H8BA	120.1
C9A—C8A—H8AA	119.9	C9B—C8B—H8BA	120.1
C8A—C9A—C4A	120.00 (11)	C8B—C9B—C4B	120.37 (11)
C8A—C9A—C10A	119.53 (11)	C8B—C9B—C10B	119.53 (11)
C4A—C9A—C10A	120.48 (11)	C4B—C9B—C10B	120.10 (11)
O2A—C10A—C9A	122.29 (11)	O2B—C10B—C9B	122.45 (11)
O2A—C10A—C1A	120.24 (11)	O2B—C10B—C1B	119.78 (11)
C9A—C10A—C1A	117.45 (11)	C9B—C10B—C1B	117.77 (11)
O3A—C11A—N1A	120.52 (11)	O3B—C11B—N1B	120.39 (11)
O3A—C11A—C12A	122.84 (12)	O3B—C11B—C12B	122.35 (11)
N1A—C11A—C12A	116.56 (11)	N1B—C11B—C12B	117.14 (11)
C13A—C12A—C17A	120.08 (12)	C17B—C12B—C13B	120.25 (12)
C13A—C12A—C11A	121.06 (12)	C17B—C12B—C11B	117.80 (12)
C17A—C12A—C11A	118.55 (12)	C13B—C12B—C11B	121.52 (11)
C14A—C13A—C12A	120.29 (13)	C14B—C13B—C12B	119.90 (13)
C14A—C13A—H13A	119.9	C14B—C13B—H13B	120.1
C12A—C13A—H13A	119.9	C12B—C13B—H13B	120.1
C15A—C14A—C13A	119.78 (13)	C15B—C14B—C13B	119.42 (13)
C15A—C14A—H14A	120.1	C15B—C14B—H14B	120.3
C13A—C14A—H14A	120.1	C13B—C14B—H14B	120.3
C14A—C15A—C16A	119.99 (12)	C14B—C15B—C16B	120.80 (13)
C14A—C15A—H15A	120.0	C14B—C15B—H15B	119.6
C16A—C15A—H15A	120.0	C16B—C15B—H15B	119.6
C17A—C16A—C15A	120.40 (13)	C17B—C16B—C15B	119.74 (14)
C17A—C16A—H16A	119.8	C17B—C16B—H16B	120.1
C15A—C16A—H16A	119.8	C15B—C16B—H16B	120.1
C16A—C17A—C12A	119.45 (13)	C16B—C17B—C12B	119.88 (13)
C16A—C17A—H17A	120.3	C16B—C17B—H17B	120.1
C12A—C17A—H17A	120.3	C12B—C17B—H17B	120.1
O4A—C18A—N1A	120.27 (11)	O4B—C18B—N1B	120.19 (11)
O4A—C18A—C19A	123.00 (12)	O4B—C18B—C19B	123.43 (12)
N1A—C18A—C19A	116.68 (11)	N1B—C18B—C19B	116.20 (11)
C24A—C19A—C20A	120.03 (13)	C24B—C19B—C20B	120.16 (12)
C24A—C19A—C18A	118.57 (12)	C24B—C19B—C18B	118.96 (11)
C20A—C19A—C18A	121.36 (12)	C20B—C19B—C18B	120.72 (11)
C21A—C20A—C19A	119.50 (15)	C21B—C20B—C19B	119.25 (13)
C21A—C20A—H20A	120.3	C21B—C20B—H20B	120.4
C19A—C20A—H20A	120.3	C19B—C20B—H20B	120.4
C22A—C21A—C20A	120.30 (16)	C22B—C21B—C20B	120.66 (13)
C22A—C21A—H21A	119.8	C22B—C21B—H21B	119.7
C20A—C21A—H21A	119.8	C20B—C21B—H21B	119.7
C21A—C22A—C23A	120.65 (15)	C21B—C22B—C23B	120.15 (13)
C21A—C22A—H22A	119.7	C21B—C22B—H22B	119.9
C23A—C22A—H22A	119.7	C23B—C22B—H22B	119.9
C22A—C23A—C24A	119.68 (16)	C22B—C23B—C24B	119.52 (13)
C22A—C23A—H23A	120.2	C22B—C23B—H23B	120.2
C24A—C23A—H23A	120.2	C24B—C23B—H23B	120.2
C19A—C24A—C23A	119.77 (15)	C19B—C24B—C23B	120.22 (13)
C19A—C24A—H24A	120.1	C19B—C24B—H24B	119.9
C23A—C24A—H24A	120.1	C23B—C24B—H24B	119.9
C18A—N1A—C1A—C2A	−121.12 (13)	C18B—N1B—C1B—C2B	121.05 (13)
C11A—N1A—C1A—C2A	42.95 (17)	C11B—N1B—C1B—C2B	−44.89 (17)
C18A—N1A—C1A—C10A	60.33 (14)	C18B—N1B—C1B—C10B	−59.77 (14)
C11A—N1A—C1A—C10A	−135.60 (11)	C11B—N1B—C1B—C10B	134.29 (12)
N1A—C1A—C2A—C3A	178.38 (11)	N1B—C1B—C2B—C3B	−176.55 (11)
C10A—C1A—C2A—C3A	−3.15 (18)	C10B—C1B—C2B—C3B	4.32 (18)
C1A—C2A—C3A—O1A	−179.48 (12)	C1B—C2B—C3B—O1B	−179.43 (12)
C1A—C2A—C3A—C4A	−1.66 (18)	C1B—C2B—C3B—C4B	2.96 (17)
O1A—C3A—C4A—C5A	1.75 (19)	O1B—C3B—C4B—C5B	−3.17 (18)
C2A—C3A—C4A—C5A	−176.04 (11)	C2B—C3B—C4B—C5B	174.43 (11)
O1A—C3A—C4A—C9A	−179.21 (12)	O1B—C3B—C4B—C9B	176.20 (12)
C2A—C3A—C4A—C9A	2.99 (17)	C2B—C3B—C4B—C9B	−6.21 (17)
C9A—C4A—C5A—C6A	0.46 (19)	C9B—C4B—C5B—C6B	−0.20 (19)
C3A—C4A—C5A—C6A	179.50 (12)	C3B—C4B—C5B—C6B	179.17 (12)
C4A—C5A—C6A—C7A	−0.6 (2)	C4B—C5B—C6B—C7B	−0.9 (2)
C5A—C6A—C7A—C8A	0.7 (2)	C5B—C6B—C7B—C8B	0.6 (2)
C6A—C7A—C8A—C9A	−0.6 (2)	C6B—C7B—C8B—C9B	0.8 (2)
C7A—C8A—C9A—C4A	0.51 (19)	C7B—C8B—C9B—C4B	−1.84 (19)
C7A—C8A—C9A—C10A	−179.45 (12)	C7B—C8B—C9B—C10B	178.24 (12)
C5A—C4A—C9A—C8A	−0.42 (18)	C5B—C4B—C9B—C8B	1.57 (18)
C3A—C4A—C9A—C8A	−179.46 (11)	C3B—C4B—C9B—C8B	−177.80 (12)
C5A—C4A—C9A—C10A	179.53 (11)	C5B—C4B—C9B—C10B	−178.51 (11)
C3A—C4A—C9A—C10A	0.49 (17)	C3B—C4B—C9B—C10B	2.11 (17)
C8A—C9A—C10A—O2A	−6.40 (18)	C8B—C9B—C10B—O2B	5.41 (19)
C4A—C9A—C10A—O2A	173.65 (11)	C4B—C9B—C10B—O2B	−174.51 (11)
C8A—C9A—C10A—C1A	174.88 (11)	C8B—C9B—C10B—C1B	−175.12 (11)
C4A—C9A—C10A—C1A	−5.08 (17)	C4B—C9B—C10B—C1B	4.96 (17)
C2A—C1A—C10A—O2A	−172.23 (12)	C2B—C1B—C10B—O2B	171.11 (12)
N1A—C1A—C10A—O2A	6.34 (17)	N1B—C1B—C10B—O2B	−8.09 (16)
C2A—C1A—C10A—C9A	6.52 (17)	C2B—C1B—C10B—C9B	−8.38 (17)
N1A—C1A—C10A—C9A	−174.91 (10)	N1B—C1B—C10B—C9B	172.42 (10)
C18A—N1A—C11A—O3A	26.32 (17)	C18B—N1B—C11B—O3B	−29.07 (17)
C1A—N1A—C11A—O3A	−136.86 (12)	C1B—N1B—C11B—O3B	136.30 (12)
C18A—N1A—C11A—C12A	−150.51 (11)	C18B—N1B—C11B—C12B	146.89 (11)
C1A—N1A—C11A—C12A	46.31 (15)	C1B—N1B—C11B—C12B	−47.74 (15)
O3A—C11A—C12A—C13A	−148.30 (13)	O3B—C11B—C12B—C17B	−24.03 (17)
N1A—C11A—C12A—C13A	28.45 (17)	N1B—C11B—C12B—C17B	160.09 (11)
O3A—C11A—C12A—C17A	25.29 (18)	O3B—C11B—C12B—C13B	148.41 (12)
N1A—C11A—C12A—C17A	−157.96 (11)	N1B—C11B—C12B—C13B	−27.47 (16)
C17A—C12A—C13A—C14A	0.56 (19)	C17B—C12B—C13B—C14B	−1.38 (18)
C11A—C12A—C13A—C14A	174.05 (11)	C11B—C12B—C13B—C14B	−173.64 (11)
C12A—C13A—C14A—C15A	0.46 (19)	C12B—C13B—C14B—C15B	0.62 (19)
C13A—C14A—C15A—C16A	−0.7 (2)	C13B—C14B—C15B—C16B	0.0 (2)
C14A—C15A—C16A—C17A	−0.1 (2)	C14B—C15B—C16B—C17B	0.1 (2)
C15A—C16A—C17A—C12A	1.1 (2)	C15B—C16B—C17B—C12B	−0.9 (2)
C13A—C12A—C17A—C16A	−1.33 (19)	C13B—C12B—C17B—C16B	1.51 (19)
C11A—C12A—C17A—C16A	−174.98 (11)	C11B—C12B—C17B—C16B	174.05 (11)
C1A—N1A—C18A—O4A	16.11 (17)	C11B—N1B—C18B—O4B	149.16 (12)
C11A—N1A—C18A—O4A	−147.96 (12)	C1B—N1B—C18B—O4B	−17.25 (17)
C1A—N1A—C18A—C19A	−161.39 (11)	C11B—N1B—C18B—C19B	−35.53 (16)
C11A—N1A—C18A—C19A	34.55 (16)	C1B—N1B—C18B—C19B	158.06 (11)
O4A—C18A—C19A—C24A	34.2 (2)	O4B—C18B—C19B—C24B	−42.44 (19)
N1A—C18A—C19A—C24A	−148.34 (13)	N1B—C18B—C19B—C24B	142.42 (12)
O4A—C18A—C19A—C20A	−143.71 (14)	O4B—C18B—C19B—C20B	132.94 (14)
N1A—C18A—C19A—C20A	33.72 (18)	N1B—C18B—C19B—C20B	−42.21 (17)
C24A—C19A—C20A—C21A	1.6 (2)	C24B—C19B—C20B—C21B	−0.3 (2)
C18A—C19A—C20A—C21A	179.56 (14)	C18B—C19B—C20B—C21B	−175.65 (13)
C19A—C20A—C21A—C22A	0.7 (3)	C19B—C20B—C21B—C22B	−0.9 (2)
C20A—C21A—C22A—C23A	−2.0 (3)	C20B—C21B—C22B—C23B	0.6 (2)
C21A—C22A—C23A—C24A	1.0 (3)	C21B—C22B—C23B—C24B	0.9 (2)
C20A—C19A—C24A—C23A	−2.6 (2)	C20B—C19B—C24B—C23B	1.8 (2)
C18A—C19A—C24A—C23A	179.40 (14)	C18B—C19B—C24B—C23B	177.18 (13)
C22A—C23A—C24A—C19A	1.3 (3)	C22B—C23B—C24B—C19B	−2.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C21A—H21A···O2Bi	0.95	2.41	3.1270 (19)	132
C14B—H14B···O3Aii	0.95	2.50	3.4345 (17)	168
C15B—H15B···O4Aiii	0.95	2.62	3.4638 (17)	148
C22B—H22B···O2A	0.95	2.54	3.2054 (17)	127
C14A—H14A···O3B	0.95	2.44	3.2303 (16)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21A—H21A⋯O2B i	0.95	2.41	3.1270 (19)	132
C14B—H14B⋯O3A ii	0.95	2.50	3.4345 (17)	168
C15B—H15B⋯O4A iii	0.95	2.62	3.4638 (17)	148
C22B—H22B⋯O2A	0.95	2.54	3.2054 (17)	127
C14A—H14A⋯O3B	0.95	2.44	3.2303 (16)	140

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