3,3'-Dinitro-bis-phenol A.

THE TITLE COMPOUND [SYSTEMATIC NAME: 2,2'-dinitro-4,4'-(propane-2,2-di-yl)diphenol], C(15)H(14)N(2)O(6), crystallizes with two mol-ecules in the asymmetric unit. Both have a trans conformation for their OH groups, and in each, the two aromatic rings are nearly orthogonal, with dihedral angles of 88.30 (3) and 89.62 (2)°. The nitro groups are nearly in the planes of their attached benzene rings, with C-C-N-O torsion angles in the range 1.21 (17)-4.06 (17)°, and they each accept an intra-molecular O-H⋯O hydrogen bond from their adjacent OH groups. One of the OH groups also forms a weak inter-molecular O-H⋯O hydrogen bond.

Related literature

For background information on bis­phenol A and its uses and environmental effects, see: Hong-Mei & Nicell (2008 ▶); Lang et al. (2008 ▶); Masuda et al. (2005 ▶); Murrell (2006 ▶); Nakamura et al. (2011 ▶); Richter et al. (2007 ▶); Sakuyama et al. (2003 ▶); Toyoizumi et al. (2007 ▶); Vandenberg et al. (2009 ▶); Wang et al. (2007 ▶). For related structures, see: Bel’skii et al. (1983 ▶); Goldberg et al. (1991 ▶); Lim & Tanski (2007 ▶); Okada (1996 ▶); Wang et al. (1982 ▶). For graph-set analysis, see: Etter (1990 ▶).

Experimental

Crystal data

C15H14N2O6

M = 318.28

Triclinic,

a = 8.3989 (5) Å

b = 12.5738 (7) Å

c = 15.3757 (9) Å

α = 66.967 (2)°

β = 76.565 (2)°

γ = 77.833 (2)°

V = 1440.34 (14) Å3

Z = 4

Cu Kα radiation

μ = 0.98 mm−1

T = 90 K

0.30 × 0.24 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.758, T max = 0.867

17716 measured reflections

5276 independent reflections

5010 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.092

S = 1.04

5276 reflections

432 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811035458/hb6392sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035458/hb6392Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811035458/hb6392Isup3.cml

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

C15H14N2O6	Z = 4
Mr = 318.28	F(000) = 664
Triclinic, P1	Dx = 1.468 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 8.3989 (5) Å	Cell parameters from 9978 reflections
b = 12.5738 (7) Å	θ = 3.8–69.4°
c = 15.3757 (9) Å	µ = 0.98 mm−1
α = 66.967 (2)°	T = 90 K
β = 76.565 (2)°	Needle fragment, yellow
γ = 77.833 (2)°	0.30 × 0.24 × 0.15 mm
V = 1440.34 (14) Å3

Bruker Kappa APEXII CCD diffractometer	5276 independent reflections
Radiation source: fine-focus sealed tube	5010 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 69.8°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −8→10
Tmin = 0.758, Tmax = 0.867	k = −15→15
17716 measured reflections	l = −16→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.0456P)2 + 0.5723P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
5276 reflections	Δρmax = 0.32 e Å−3
432 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0019 (2)

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	0.22904 (13)	0.58866 (9)	0.48806 (7)	0.0294 (2)
H1	0.123 (3)	0.5893 (17)	0.4943 (14)	0.044*
O2	0.73621 (11)	0.03318 (7)	0.95361 (6)	0.02063 (19)
H2	0.829 (2)	0.0338 (15)	0.9658 (12)	0.031*
O3	−0.07766 (12)	0.57717 (8)	0.56906 (7)	0.0292 (2)
O4	−0.15232 (11)	0.55090 (9)	0.71963 (7)	0.0287 (2)
O5	0.97246 (11)	0.12665 (8)	0.96739 (7)	0.0272 (2)
O6	0.93932 (12)	0.30789 (8)	0.95141 (9)	0.0350 (3)
N1	−0.04492 (13)	0.55927 (9)	0.64899 (8)	0.0224 (2)
N2	0.88736 (13)	0.22431 (9)	0.95078 (8)	0.0212 (2)
C1	0.25048 (16)	0.56709 (11)	0.57760 (9)	0.0216 (3)
C2	0.12602 (15)	0.54936 (10)	0.65832 (9)	0.0194 (3)
C3	0.16117 (15)	0.52384 (10)	0.74984 (9)	0.0176 (2)
H3	0.0743	0.5110	0.8034	0.021*
C4	0.32013 (14)	0.51728 (10)	0.76286 (8)	0.0163 (2)
C5	0.44549 (15)	0.53631 (10)	0.68122 (9)	0.0197 (3)
H5	0.5562	0.5318	0.6886	0.024*
C6	0.41164 (16)	0.56111 (11)	0.59161 (9)	0.0225 (3)
H6	0.4988	0.5744	0.5383	0.027*
C7	0.36794 (14)	0.48809 (10)	0.86086 (8)	0.0162 (2)
C8	0.47801 (14)	0.36988 (10)	0.88453 (8)	0.0153 (2)
C9	0.63366 (14)	0.35074 (10)	0.90618 (8)	0.0166 (2)
H9	0.6805	0.4137	0.9054	0.020*
C10	0.72413 (14)	0.23857 (10)	0.92944 (8)	0.0169 (2)
C11	0.66033 (15)	0.14318 (10)	0.93106 (8)	0.0167 (2)
C12	0.50322 (15)	0.16441 (10)	0.90675 (8)	0.0177 (2)
H12	0.4569	0.1023	0.9056	0.021*
C13	0.41528 (14)	0.27400 (10)	0.88453 (8)	0.0172 (2)
H13	0.3086	0.2859	0.8686	0.021*
C14	0.45545 (14)	0.58693 (10)	0.85565 (9)	0.0178 (2)
H14A	0.5557	0.5933	0.8072	0.027*
H14B	0.4851	0.5697	0.9182	0.027*
H14C	0.3812	0.6607	0.8382	0.027*
C15	0.21674 (14)	0.47754 (11)	0.94100 (9)	0.0187 (2)
H15A	0.1425	0.5515	0.9260	0.028*
H15B	0.2531	0.4593	1.0020	0.028*
H15C	0.1582	0.4151	0.9461	0.028*
O7	0.02131 (15)	−0.30550 (9)	0.30590 (8)	0.0365 (3)
H7	−0.080 (3)	−0.2877 (18)	0.2880 (15)	0.055*
O8	0.33303 (13)	0.14153 (10)	0.57674 (7)	0.0320 (2)
H8	0.435 (3)	0.1460 (17)	0.5692 (14)	0.048*
O9	−0.24524 (14)	−0.19241 (10)	0.24194 (8)	0.0392 (3)
O10	−0.28330 (13)	−0.00440 (11)	0.18519 (9)	0.0416 (3)
O11	0.63606 (12)	0.15267 (9)	0.49364 (7)	0.0294 (2)
O12	0.71117 (11)	0.15854 (9)	0.34782 (7)	0.0308 (2)
N3	−0.20026 (14)	−0.09626 (11)	0.22333 (9)	0.0295 (3)
N4	0.60419 (13)	0.15289 (9)	0.41816 (8)	0.0229 (2)
C16	0.05818 (17)	−0.19784 (11)	0.28560 (9)	0.0243 (3)
C17	−0.04478 (15)	−0.09397 (12)	0.24732 (9)	0.0221 (3)
C18	−0.00188 (15)	0.01496 (11)	0.23027 (8)	0.0194 (3)
H18	−0.0754	0.0838	0.2053	0.023*
C19	0.14606 (14)	0.02296 (10)	0.24948 (8)	0.0169 (2)
C20	0.25088 (15)	−0.08150 (11)	0.28611 (8)	0.0200 (3)
H20	0.3541	−0.0778	0.2994	0.024*
C21	0.20879 (17)	−0.18877 (11)	0.30335 (9)	0.0238 (3)
H21	0.2833	−0.2573	0.3276	0.029*
C22	0.20487 (14)	0.13939 (10)	0.22818 (8)	0.0179 (2)
C23	0.24781 (15)	0.13806 (10)	0.32030 (8)	0.0171 (2)
C24	0.40497 (15)	0.14409 (10)	0.32903 (9)	0.0180 (2)
H24	0.4928	0.1474	0.2768	0.022*
C25	0.43654 (15)	0.14534 (10)	0.41427 (9)	0.0194 (3)
C26	0.31108 (16)	0.14011 (11)	0.49325 (9)	0.0225 (3)
C27	0.15235 (16)	0.13151 (11)	0.48457 (9)	0.0234 (3)
H27	0.0646	0.1264	0.5371	0.028*
C28	0.12238 (15)	0.13041 (11)	0.40085 (9)	0.0203 (3)
H28	0.0136	0.1243	0.3970	0.024*
C29	0.07223 (16)	0.24398 (11)	0.19345 (9)	0.0223 (3)
H29A	−0.0281	0.2348	0.2419	0.033*
H29B	0.0469	0.2477	0.1332	0.033*
H29C	0.1133	0.3161	0.1832	0.033*
C30	0.35372 (16)	0.15349 (11)	0.14636 (9)	0.0216 (3)
H30A	0.3934	0.2279	0.1305	0.032*
H30B	0.3203	0.1523	0.0898	0.032*
H30C	0.4423	0.0893	0.1666	0.032*

	U11	U22	U33	U12	U13	U23
O1	0.0321 (5)	0.0389 (6)	0.0185 (5)	−0.0099 (4)	−0.0084 (4)	−0.0066 (4)
O2	0.0209 (4)	0.0159 (4)	0.0250 (5)	−0.0003 (3)	−0.0054 (4)	−0.0075 (3)
O3	0.0303 (5)	0.0322 (5)	0.0299 (5)	−0.0016 (4)	−0.0171 (4)	−0.0107 (4)
O4	0.0172 (4)	0.0393 (6)	0.0358 (5)	−0.0012 (4)	−0.0053 (4)	−0.0207 (4)
O5	0.0218 (5)	0.0205 (4)	0.0398 (5)	0.0046 (4)	−0.0127 (4)	−0.0110 (4)
O6	0.0249 (5)	0.0259 (5)	0.0648 (7)	0.0000 (4)	−0.0213 (5)	−0.0216 (5)
N1	0.0219 (5)	0.0199 (5)	0.0285 (6)	−0.0001 (4)	−0.0103 (5)	−0.0100 (4)
N2	0.0191 (5)	0.0199 (5)	0.0266 (5)	0.0000 (4)	−0.0077 (4)	−0.0097 (4)
C1	0.0280 (6)	0.0189 (6)	0.0184 (6)	−0.0035 (5)	−0.0071 (5)	−0.0053 (5)
C2	0.0185 (6)	0.0163 (6)	0.0248 (6)	−0.0004 (4)	−0.0078 (5)	−0.0073 (5)
C3	0.0175 (6)	0.0153 (5)	0.0204 (6)	−0.0010 (4)	−0.0031 (5)	−0.0075 (5)
C4	0.0172 (5)	0.0138 (5)	0.0182 (6)	−0.0009 (4)	−0.0042 (4)	−0.0058 (4)
C5	0.0171 (6)	0.0206 (6)	0.0215 (6)	−0.0026 (5)	−0.0034 (5)	−0.0077 (5)
C6	0.0226 (6)	0.0253 (6)	0.0188 (6)	−0.0063 (5)	0.0001 (5)	−0.0077 (5)
C7	0.0148 (5)	0.0164 (6)	0.0179 (6)	−0.0019 (4)	−0.0036 (4)	−0.0064 (4)
C8	0.0167 (5)	0.0168 (6)	0.0120 (5)	−0.0026 (4)	−0.0011 (4)	−0.0053 (4)
C9	0.0179 (6)	0.0167 (6)	0.0168 (5)	−0.0038 (4)	−0.0027 (4)	−0.0072 (4)
C10	0.0150 (5)	0.0201 (6)	0.0163 (5)	−0.0024 (4)	−0.0030 (4)	−0.0071 (5)
C11	0.0203 (6)	0.0159 (6)	0.0123 (5)	−0.0023 (4)	0.0000 (4)	−0.0049 (4)
C12	0.0203 (6)	0.0179 (6)	0.0169 (6)	−0.0070 (4)	−0.0006 (4)	−0.0075 (5)
C13	0.0157 (5)	0.0207 (6)	0.0163 (5)	−0.0041 (4)	−0.0025 (4)	−0.0070 (5)
C14	0.0183 (6)	0.0162 (6)	0.0204 (6)	−0.0021 (4)	−0.0050 (5)	−0.0071 (5)
C15	0.0161 (5)	0.0220 (6)	0.0189 (6)	−0.0020 (4)	−0.0021 (5)	−0.0092 (5)
O7	0.0443 (6)	0.0244 (5)	0.0442 (6)	−0.0143 (5)	0.0001 (5)	−0.0154 (5)
O8	0.0334 (5)	0.0488 (6)	0.0207 (5)	−0.0137 (5)	−0.0033 (4)	−0.0161 (4)
O9	0.0400 (6)	0.0526 (7)	0.0410 (6)	−0.0249 (5)	0.0004 (5)	−0.0283 (5)
O10	0.0264 (5)	0.0546 (7)	0.0569 (7)	0.0005 (5)	−0.0169 (5)	−0.0316 (6)
O11	0.0324 (5)	0.0335 (5)	0.0261 (5)	−0.0102 (4)	−0.0129 (4)	−0.0075 (4)
O12	0.0200 (5)	0.0425 (6)	0.0307 (5)	−0.0095 (4)	−0.0009 (4)	−0.0132 (4)
N3	0.0243 (6)	0.0443 (7)	0.0306 (6)	−0.0096 (5)	−0.0001 (5)	−0.0246 (6)
N4	0.0236 (5)	0.0203 (5)	0.0247 (6)	−0.0057 (4)	−0.0068 (5)	−0.0051 (4)
C16	0.0325 (7)	0.0219 (6)	0.0199 (6)	−0.0096 (5)	0.0034 (5)	−0.0105 (5)
C17	0.0209 (6)	0.0308 (7)	0.0197 (6)	−0.0074 (5)	0.0009 (5)	−0.0149 (5)
C18	0.0201 (6)	0.0225 (6)	0.0164 (6)	−0.0006 (5)	−0.0021 (4)	−0.0096 (5)
C19	0.0193 (6)	0.0188 (6)	0.0128 (5)	−0.0027 (5)	−0.0006 (4)	−0.0070 (4)
C20	0.0206 (6)	0.0216 (6)	0.0173 (6)	−0.0019 (5)	−0.0039 (5)	−0.0066 (5)
C21	0.0293 (7)	0.0186 (6)	0.0193 (6)	−0.0001 (5)	−0.0023 (5)	−0.0050 (5)
C22	0.0190 (6)	0.0173 (6)	0.0172 (6)	−0.0027 (5)	−0.0027 (5)	−0.0060 (5)
C23	0.0197 (6)	0.0137 (5)	0.0175 (6)	−0.0027 (4)	−0.0028 (5)	−0.0053 (4)
C24	0.0188 (6)	0.0156 (5)	0.0174 (6)	−0.0035 (4)	−0.0007 (4)	−0.0044 (4)
C25	0.0196 (6)	0.0172 (6)	0.0212 (6)	−0.0051 (4)	−0.0046 (5)	−0.0047 (5)
C26	0.0288 (7)	0.0224 (6)	0.0178 (6)	−0.0060 (5)	−0.0037 (5)	−0.0078 (5)
C27	0.0229 (6)	0.0276 (7)	0.0200 (6)	−0.0071 (5)	0.0027 (5)	−0.0104 (5)
C28	0.0181 (6)	0.0221 (6)	0.0216 (6)	−0.0045 (5)	−0.0016 (5)	−0.0088 (5)
C29	0.0257 (6)	0.0176 (6)	0.0230 (6)	−0.0006 (5)	−0.0070 (5)	−0.0060 (5)
C30	0.0240 (6)	0.0235 (6)	0.0171 (6)	−0.0072 (5)	−0.0002 (5)	−0.0068 (5)

O1—C1	1.3431 (15)	O7—C16	1.3516 (16)
O1—H1	0.88 (2)	O7—H7	0.91 (2)
O2—C11	1.3398 (14)	O8—C26	1.3460 (15)
O2—H2	0.844 (19)	O8—H8	0.85 (2)
O3—N1	1.2456 (14)	O9—N3	1.2481 (16)
O4—N1	1.2246 (15)	O10—N3	1.2185 (17)
O5—N2	1.2464 (14)	O11—N4	1.2490 (14)
O6—N2	1.2240 (14)	O12—N4	1.2237 (15)
N1—C2	1.4504 (16)	N3—C17	1.4457 (17)
N2—C10	1.4418 (15)	N4—C25	1.4475 (16)
C1—C2	1.4005 (18)	C16—C21	1.3903 (19)
C1—C6	1.4014 (18)	C16—C17	1.3997 (19)
C2—C3	1.4037 (17)	C17—C18	1.3991 (18)
C3—C4	1.3763 (17)	C18—C19	1.3739 (17)
C3—H3	0.9500	C18—H18	0.9500
C4—C5	1.4138 (17)	C19—C20	1.4077 (17)
C4—C7	1.5339 (16)	C19—C22	1.5326 (16)
C5—C6	1.3729 (18)	C20—C21	1.3755 (18)
C5—H5	0.9500	C20—H20	0.9500
C6—H6	0.9500	C21—H21	0.9500
C7—C8	1.5331 (16)	C22—C23	1.5340 (16)
C7—C15	1.5377 (16)	C22—C29	1.5378 (16)
C7—C14	1.5398 (15)	C22—C30	1.5379 (16)
C8—C9	1.3729 (17)	C23—C24	1.3779 (17)
C8—C13	1.4137 (16)	C23—C28	1.4128 (17)
C9—C10	1.4051 (17)	C24—C25	1.4028 (17)
C9—H9	0.9500	C24—H24	0.9500
C10—C11	1.4028 (17)	C25—C26	1.4006 (18)
C11—C12	1.3981 (17)	C26—C27	1.4004 (18)
C12—C13	1.3715 (17)	C27—C28	1.3736 (18)
C12—H12	0.9500	C27—H27	0.9500
C13—H13	0.9500	C28—H28	0.9500
C14—H14A	0.9800	C29—H29A	0.9800
C14—H14B	0.9800	C29—H29B	0.9800
C14—H14C	0.9800	C29—H29C	0.9800
C15—H15A	0.9800	C30—H30A	0.9800
C15—H15B	0.9800	C30—H30B	0.9800
C15—H15C	0.9800	C30—H30C	0.9800
C1—O1—H1	103.2 (13)	C16—O7—H7	100.9 (14)
C11—O2—H2	106.1 (12)	C26—O8—H8	104.9 (14)
O4—N1—O3	122.20 (10)	O10—N3—O9	121.88 (12)
O4—N1—C2	119.00 (10)	O10—N3—C17	119.13 (12)
O3—N1—C2	118.80 (11)	O9—N3—C17	118.99 (12)
O6—N2—O5	121.75 (10)	O12—N4—O11	121.70 (11)
O6—N2—C10	119.57 (10)	O12—N4—C25	119.28 (10)
O5—N2—C10	118.68 (10)	O11—N4—C25	119.02 (10)
O1—C1—C2	125.71 (12)	O7—C16—C21	118.19 (12)
O1—C1—C6	117.15 (11)	O7—C16—C17	124.50 (13)
C2—C1—C6	117.14 (11)	C21—C16—C17	117.31 (11)
C1—C2—C3	121.63 (11)	C18—C17—C16	121.91 (12)
C1—C2—N1	120.44 (11)	C18—C17—N3	117.65 (12)
C3—C2—N1	117.92 (11)	C16—C17—N3	120.45 (12)
C4—C3—C2	120.71 (11)	C19—C18—C17	120.35 (11)
C4—C3—H3	119.6	C19—C18—H18	119.8
C2—C3—H3	119.6	C17—C18—H18	119.8
C3—C4—C5	117.64 (11)	C18—C19—C20	117.60 (11)
C3—C4—C7	123.54 (10)	C18—C19—C22	123.22 (11)
C5—C4—C7	118.81 (10)	C20—C19—C22	119.09 (10)
C6—C5—C4	121.82 (11)	C21—C20—C19	122.20 (12)
C6—C5—H5	119.1	C21—C20—H20	118.9
C4—C5—H5	119.1	C19—C20—H20	118.9
C5—C6—C1	121.04 (11)	C20—C21—C16	120.59 (12)
C5—C6—H6	119.5	C20—C21—H21	119.7
C1—C6—H6	119.5	C16—C21—H21	119.7
C8—C7—C4	107.24 (9)	C19—C22—C23	108.55 (9)
C8—C7—C15	108.16 (9)	C19—C22—C29	112.24 (10)
C4—C7—C15	112.37 (9)	C23—C22—C29	108.67 (9)
C8—C7—C14	112.85 (9)	C19—C22—C30	107.55 (9)
C4—C7—C14	108.79 (9)	C23—C22—C30	112.75 (10)
C15—C7—C14	107.52 (9)	C29—C22—C30	107.13 (10)
C9—C8—C13	117.69 (10)	C24—C23—C28	117.43 (11)
C9—C8—C7	124.27 (10)	C24—C23—C22	123.05 (10)
C13—C8—C7	118.04 (10)	C28—C23—C22	119.52 (10)
C8—C9—C10	120.35 (11)	C23—C24—C25	120.66 (11)
C8—C9—H9	119.8	C23—C24—H24	119.7
C10—C9—H9	119.8	C25—C24—H24	119.7
C11—C10—C9	121.81 (11)	C26—C25—C24	121.68 (11)
C11—C10—N2	120.50 (10)	C26—C25—N4	120.59 (11)
C9—C10—N2	117.69 (10)	C24—C25—N4	117.73 (11)
O2—C11—C12	116.73 (10)	O8—C26—C27	118.06 (11)
O2—C11—C10	126.02 (11)	O8—C26—C25	124.59 (12)
C12—C11—C10	117.25 (11)	C27—C26—C25	117.35 (11)
C13—C12—C11	120.63 (11)	C28—C27—C26	120.63 (11)
C13—C12—H12	119.7	C28—C27—H27	119.7
C11—C12—H12	119.7	C26—C27—H27	119.7
C12—C13—C8	122.25 (11)	C27—C28—C23	122.24 (11)
C12—C13—H13	118.9	C27—C28—H28	118.9
C8—C13—H13	118.9	C23—C28—H28	118.9
C7—C14—H14A	109.5	C22—C29—H29A	109.5
C7—C14—H14B	109.5	C22—C29—H29B	109.5
H14A—C14—H14B	109.5	H29A—C29—H29B	109.5
C7—C14—H14C	109.5	C22—C29—H29C	109.5
H14A—C14—H14C	109.5	H29A—C29—H29C	109.5
H14B—C14—H14C	109.5	H29B—C29—H29C	109.5
C7—C15—H15A	109.5	C22—C30—H30A	109.5
C7—C15—H15B	109.5	C22—C30—H30B	109.5
H15A—C15—H15B	109.5	H30A—C30—H30B	109.5
C7—C15—H15C	109.5	C22—C30—H30C	109.5
H15A—C15—H15C	109.5	H30A—C30—H30C	109.5
H15B—C15—H15C	109.5	H30B—C30—H30C	109.5
O1—C1—C2—C3	178.07 (11)	O7—C16—C17—C18	178.18 (11)
C6—C1—C2—C3	−1.52 (18)	C21—C16—C17—C18	−2.11 (18)
O1—C1—C2—N1	−3.15 (19)	O7—C16—C17—N3	−2.24 (19)
C6—C1—C2—N1	177.26 (11)	C21—C16—C17—N3	177.47 (11)
O4—N1—C2—C1	−175.24 (11)	O10—N3—C17—C18	3.63 (17)
O3—N1—C2—C1	4.06 (17)	O9—N3—C17—C18	−176.67 (11)
O4—N1—C2—C3	3.58 (16)	O10—N3—C17—C16	−175.96 (12)
O3—N1—C2—C3	−177.12 (10)	O9—N3—C17—C16	3.73 (18)
C1—C2—C3—C4	1.06 (18)	C16—C17—C18—C19	1.12 (18)
N1—C2—C3—C4	−177.74 (10)	N3—C17—C18—C19	−178.47 (10)
C2—C3—C4—C5	−0.42 (17)	C17—C18—C19—C20	0.22 (17)
C2—C3—C4—C7	−179.08 (10)	C17—C18—C19—C22	177.00 (10)
C3—C4—C5—C6	0.32 (17)	C18—C19—C20—C21	−0.52 (18)
C7—C4—C5—C6	179.05 (11)	C22—C19—C20—C21	−177.43 (11)
C4—C5—C6—C1	−0.85 (19)	C19—C20—C21—C16	−0.53 (19)
O1—C1—C6—C5	−178.22 (11)	O7—C16—C21—C20	−178.48 (11)
C2—C1—C6—C5	1.41 (18)	C17—C16—C21—C20	1.79 (18)
C3—C4—C7—C8	113.79 (12)	C18—C19—C22—C23	126.24 (11)
C5—C4—C7—C8	−64.86 (13)	C20—C19—C22—C23	−57.03 (13)
C3—C4—C7—C15	−4.93 (15)	C18—C19—C22—C29	6.11 (16)
C5—C4—C7—C15	176.43 (10)	C20—C19—C22—C29	−177.16 (10)
C3—C4—C7—C14	−123.86 (12)	C18—C19—C22—C30	−111.48 (12)
C5—C4—C7—C14	57.49 (13)	C20—C19—C22—C30	65.25 (13)
C4—C7—C8—C9	124.49 (11)	C19—C22—C23—C24	116.54 (12)
C15—C7—C8—C9	−114.11 (12)	C29—C22—C23—C24	−121.12 (12)
C14—C7—C8—C9	4.71 (16)	C30—C22—C23—C24	−2.51 (16)
C4—C7—C8—C13	−55.80 (13)	C19—C22—C23—C28	−63.49 (13)
C15—C7—C8—C13	65.61 (13)	C29—C22—C23—C28	58.84 (14)
C14—C7—C8—C13	−175.57 (10)	C30—C22—C23—C28	177.46 (10)
C13—C8—C9—C10	−1.38 (16)	C28—C23—C24—C25	−1.49 (17)
C7—C8—C9—C10	178.33 (10)	C22—C23—C24—C25	178.47 (10)
C8—C9—C10—C11	0.28 (17)	C23—C24—C25—C26	0.25 (18)
C8—C9—C10—N2	179.55 (10)	C23—C24—C25—N4	−179.43 (10)
O6—N2—C10—C11	−178.15 (11)	O12—N4—C25—C26	−179.27 (11)
O5—N2—C10—C11	2.44 (17)	O11—N4—C25—C26	1.21 (17)
O6—N2—C10—C9	2.57 (17)	O12—N4—C25—C24	0.42 (17)
O5—N2—C10—C9	−176.84 (11)	O11—N4—C25—C24	−179.11 (10)
C9—C10—C11—O2	−179.00 (11)	C24—C25—C26—O8	−179.66 (12)
N2—C10—C11—O2	1.75 (18)	N4—C25—C26—O8	0.01 (19)
C9—C10—C11—C12	1.15 (17)	C24—C25—C26—C27	1.07 (18)
N2—C10—C11—C12	−178.10 (10)	N4—C25—C26—C27	−179.26 (11)
O2—C11—C12—C13	178.70 (10)	O8—C26—C27—C28	179.59 (12)
C10—C11—C12—C13	−1.43 (17)	C25—C26—C27—C28	−1.10 (19)
C11—C12—C13—C8	0.33 (18)	C26—C27—C28—C23	−0.17 (19)
C9—C8—C13—C12	1.11 (17)	C24—C23—C28—C27	1.48 (18)
C7—C8—C13—C12	−178.63 (10)	C22—C23—C28—C27	−178.49 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.88 (2)	1.80 (2)	2.5947 (14)	149.6 (18)
O2—H2···O5	0.844 (19)	1.856 (18)	2.5955 (13)	145.3 (16)
O2—H2···O5i	0.844 (19)	2.380 (18)	2.9832 (13)	128.8 (14)
O7—H7···O9	0.91 (2)	1.72 (2)	2.5667 (17)	154 (2)
O8—H8···O11	0.85 (2)	1.81 (2)	2.5747 (14)	148.8 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3	0.88 (2)	1.80 (2)	2.5947 (14)	149.6 (18)
O2—H2⋯O5	0.844 (19)	1.856 (18)	2.5955 (13)	145.3 (16)
O2—H2⋯O5i	0.844 (19)	2.380 (18)	2.9832 (13)	128.8 (14)
O7—H7⋯O9	0.91 (2)	1.72 (2)	2.5667 (17)	154 (2)
O8—H8⋯O11	0.85 (2)	1.81 (2)	2.5747 (14)	148.8 (19)

Symmetry code: (i) .