(E)-2-{[4-(Di-methyl-amino)-benzyl-idene]amino}-5-nitro-phenol.

The title Schiff base compound, C15H15N3O3, crystallizes with two mol-ecules (A and B) in the asymmetric unit. Each mol-ecule adopts an E conformation around the C= N imine bond. The two mol-ecules have minor differences in their conformations. In mol-ecule A, the dihedral angle between the nitro group and its benzene ring is 2.1 (2)° and that between the two benzene rings is 0.88 (7)°, while the corresponding angles for mol-ecule B are 5.7 (1) and 2.45 (6)°, respectively. In each mol-ecule, there is an intra-molecular O-H⋯N hydrogen bond. In the crystal, inversion-related mol-ecules are linked via O-H⋯O hydrogen bonds forming A-A and B-B dimers. These dimers are linked via C-H⋯O hydrogen bonds involving the nitro O atoms, forming A-A-A and B-B-B slabs that lie parallel to one another and to (010).

Related literature

For related structures, see: Rodríguez et al. (2012 ▶); Valkonen et al. (2012 ▶); Gül et al. (2007 ▶); Reyes et al. (2004 ▶); Hijji et al. (2014 ▶). For the applications of Schiff bases as anion n class="Gene">sensors, see: Hijji et al. (2009 ▶), and in non-linear optics, see: Muñoz et al. (2008 ▶).

Experimental

Crystal data

C15H15N3O3

M = 285.30

Triclinic,

a = 6.1435 (3) Å

b = 14.3844 (8) Å

c = 15.8516 (9) Å

α = 108.038 (5)°

β = 91.258 (4)°

γ = 96.033 (4)°

V = 1322.37 (13) Å3

Z = 4

Cu Kα radiation

μ = 0.84 mm−1

T = 123 K

0.32 × 0.24 × 0.19 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.938, T max = 1.000

9056 measured reflections

9056 independent reflections

7791 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.119

S = 1.04

9056 reflections

392 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S160053681400871X/su2709sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681400871X/su2709Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681400871X/su2709Isup3.cml

CCDC reference: 997774

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

C15H15N3O3	Z = 4
Mr = 285.30	F(000) = 600
Triclinic, P1	Dx = 1.433 Mg m−3
a = 6.1435 (3) Å	Cu Kα radiation, λ = 1.54184 Å
b = 14.3844 (8) Å	Cell parameters from 3857 reflections
c = 15.8516 (9) Å	θ = 5.0–74.3°
α = 108.038 (5)°	µ = 0.84 mm−1
β = 91.258 (4)°	T = 123 K
γ = 96.033 (4)°	Block, yellow-brown
V = 1322.37 (13) Å3	0.32 × 0.24 × 0.19 mm

Agilent Xcalibur (Ruby, Gemini) diffractometer	9056 independent reflections
Radiation source: Enhance (Cu) X-ray Source	7791 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 10.5081 pixels mm-1	θmax = 74.2°, θmin = 5.0°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −17→17
Tmin = 0.938, Tmax = 1.000	l = −19→19
9056 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0805P)2 + 0.1015P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
9056 reflections	Δρmax = 0.32 e Å−3
392 parameters	Δρmin = −0.21 e Å−3

Experimental. Spectroscopic data for the title compound : 1H-NMR (400 MHz) δ ppm (DMSO-d6): 10.07 (s, 1H), 9.74 (s, 1H), 7.768 (d, J = 8.86 Hz, 1H), 7.68 (d, J = 8.97, 2H), 7.606 (dd, J = 8.87, 2.5 Hz, 1 H), 7.49 (d, J = 2.5 Hz, 1H), 6.78 (d, J = 8.97, 2 H), 6.63 (d, J = 8.87, 1 H), 3.069 (s, 6 H). 13C-NMR (DMSO-d6, 100 MHz) δ ppm: 189.82, 154.16, 145.54, 142.41, 135.46, 131.50, 124.48, 118.29, 111.12, 111.02, 108.59, 39.60.

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. Refined as a 2-component twin.

	x	y	z	Uiso*/Ueq
O1A	1.00034 (17)	0.44325 (8)	0.56033 (7)	0.0261 (2)
H1A	0.918 (4)	0.4353 (16)	0.5142 (16)	0.045 (6)*
O2A	1.05386 (18)	0.41323 (9)	0.86286 (8)	0.0311 (3)
O3A	0.7307 (2)	0.35008 (10)	0.88265 (8)	0.0384 (3)
N1A	0.8610 (2)	0.38209 (9)	0.83748 (8)	0.0239 (3)
N2A	0.60070 (19)	0.38449 (8)	0.49667 (8)	0.0185 (2)
N3A	0.22830 (19)	0.38081 (9)	0.11251 (8)	0.0224 (3)
C1A	0.8619 (2)	0.41242 (10)	0.61406 (10)	0.0190 (3)
C2A	0.9351 (2)	0.41382 (10)	0.69739 (10)	0.0202 (3)
H2AA	1.0832	0.4363	0.7185	0.024*
C3A	0.7849 (2)	0.38121 (10)	0.74952 (9)	0.0194 (3)
C4A	0.5674 (2)	0.34761 (10)	0.72071 (10)	0.0217 (3)
H4AA	0.4688	0.3259	0.7579	0.026*
C5A	0.4968 (2)	0.34643 (10)	0.63666 (10)	0.0201 (3)
H5AA	0.3487	0.3232	0.6160	0.024*
C6A	0.6411 (2)	0.37909 (9)	0.58198 (9)	0.0173 (3)
C7A	0.4114 (2)	0.35695 (9)	0.45511 (9)	0.0179 (3)
H7AA	0.2949	0.3322	0.4836	0.021*
C8A	0.3686 (2)	0.36216 (9)	0.36702 (9)	0.0179 (3)
C9A	0.1576 (2)	0.33220 (10)	0.32528 (10)	0.0189 (3)
H9AA	0.0445	0.3081	0.3557	0.023*
C10A	0.1101 (2)	0.33680 (10)	0.24159 (10)	0.0204 (3)
H10A	−0.0344	0.3158	0.2153	0.024*
C11A	0.2740 (2)	0.37246 (10)	0.19399 (9)	0.0174 (3)
C12A	0.4886 (2)	0.40115 (10)	0.23598 (10)	0.0197 (3)
H12A	0.6033	0.4239	0.2054	0.024*
C13A	0.5328 (2)	0.39655 (10)	0.31967 (9)	0.0188 (3)
H13A	0.6772	0.4170	0.3463	0.023*
C14A	0.4024 (3)	0.40912 (13)	0.06081 (10)	0.0286 (3)
H14A	0.4798	0.4733	0.0951	0.043*
H14B	0.3383	0.4133	0.0051	0.043*
H14C	0.5058	0.3597	0.0476	0.043*
C15A	0.0107 (2)	0.34709 (12)	0.06894 (10)	0.0267 (3)
H15A	−0.0982	0.3811	0.1074	0.040*
H15B	−0.0213	0.2760	0.0576	0.040*
H15C	0.0050	0.3615	0.0125	0.040*
O1B	0.52861 (17)	0.06146 (8)	0.59158 (7)	0.0240 (2)
H1B	0.449 (3)	0.0669 (15)	0.5502 (15)	0.038 (6)*
O2B	0.62214 (19)	0.12261 (10)	0.91582 (8)	0.0358 (3)
O3B	0.3155 (2)	0.17004 (9)	0.96784 (8)	0.0363 (3)
N1B	0.4363 (2)	0.14478 (9)	0.90623 (9)	0.0259 (3)
N2B	0.16151 (19)	0.12088 (8)	0.55922 (8)	0.0189 (2)
N3B	−0.22861 (19)	0.09965 (9)	0.17216 (8)	0.0224 (3)
C1B	0.4096 (2)	0.09763 (9)	0.66287 (9)	0.0182 (3)
C2B	0.4863 (2)	0.10243 (10)	0.74690 (10)	0.0204 (3)
H2BA	0.6231	0.0808	0.7562	0.024*
C3B	0.3569 (2)	0.13995 (10)	0.81726 (9)	0.0208 (3)
C4B	0.1556 (2)	0.17232 (10)	0.80674 (10)	0.0223 (3)
H4BA	0.0703	0.1970	0.8563	0.027*
C5B	0.0825 (2)	0.16755 (10)	0.72168 (10)	0.0199 (3)
H5BA	−0.0540	0.1898	0.7131	0.024*
C6B	0.2071 (2)	0.13050 (9)	0.64878 (9)	0.0175 (3)
C7B	−0.0179 (2)	0.14324 (9)	0.53189 (9)	0.0183 (3)
H7BA	−0.1218	0.1683	0.5741	0.022*
C8B	−0.0682 (2)	0.13184 (9)	0.43956 (9)	0.0176 (3)
C9B	−0.2682 (2)	0.15614 (9)	0.41343 (10)	0.0185 (3)
H9BA	−0.3687	0.1806	0.4573	0.022*
C10B	−0.3238 (2)	0.14565 (10)	0.32598 (9)	0.0189 (3)
H10B	−0.4613	0.1626	0.3107	0.023*
C11B	−0.1782 (2)	0.10990 (9)	0.25881 (9)	0.0180 (3)
C12B	0.0245 (2)	0.08440 (10)	0.28521 (10)	0.0194 (3)
H12B	0.1255	0.0597	0.2416	0.023*
C13B	0.0761 (2)	0.09487 (10)	0.37254 (10)	0.0185 (3)
H13B	0.2120	0.0768	0.3882	0.022*
C14B	−0.0722 (3)	0.06855 (12)	0.10417 (10)	0.0280 (3)
H14D	−0.0277	0.0051	0.1043	0.042*
H14E	0.0570	0.1179	0.1167	0.042*
H14F	−0.1406	0.0617	0.0458	0.042*
C15B	−0.4374 (2)	0.12439 (12)	0.14568 (10)	0.0269 (3)
H15D	−0.4564	0.1919	0.1810	0.040*
H15E	−0.5567	0.0788	0.1556	0.040*
H15F	−0.4398	0.1192	0.0825	0.040*

	U11	U22	U33	U12	U13	U23
O1A	0.0198 (5)	0.0421 (6)	0.0185 (5)	−0.0004 (4)	0.0012 (4)	0.0136 (4)
O2A	0.0304 (6)	0.0392 (6)	0.0236 (6)	0.0026 (5)	−0.0085 (5)	0.0109 (5)
O3A	0.0428 (7)	0.0556 (8)	0.0218 (6)	−0.0061 (6)	−0.0043 (5)	0.0239 (5)
N1A	0.0321 (7)	0.0237 (6)	0.0170 (6)	0.0046 (5)	−0.0035 (5)	0.0078 (5)
N2A	0.0214 (6)	0.0205 (5)	0.0140 (6)	0.0031 (4)	0.0001 (4)	0.0059 (4)
N3A	0.0194 (6)	0.0333 (6)	0.0164 (6)	0.0037 (5)	0.0002 (5)	0.0101 (5)
C1A	0.0206 (7)	0.0203 (6)	0.0166 (7)	0.0039 (5)	0.0027 (5)	0.0057 (5)
C2A	0.0195 (6)	0.0218 (6)	0.0189 (7)	0.0039 (5)	−0.0022 (5)	0.0057 (5)
C3A	0.0270 (7)	0.0183 (6)	0.0135 (7)	0.0045 (5)	−0.0016 (5)	0.0054 (5)
C4A	0.0259 (7)	0.0213 (6)	0.0192 (7)	−0.0005 (5)	0.0012 (6)	0.0093 (5)
C5A	0.0210 (6)	0.0212 (6)	0.0180 (7)	−0.0012 (5)	−0.0022 (5)	0.0075 (5)
C6A	0.0218 (6)	0.0146 (6)	0.0157 (7)	0.0033 (5)	−0.0010 (5)	0.0048 (5)
C7A	0.0205 (6)	0.0178 (6)	0.0164 (7)	0.0043 (5)	0.0024 (5)	0.0063 (5)
C8A	0.0209 (6)	0.0158 (6)	0.0168 (7)	0.0037 (5)	0.0003 (5)	0.0045 (5)
C9A	0.0205 (6)	0.0200 (6)	0.0170 (7)	0.0008 (5)	0.0014 (5)	0.0075 (5)
C10A	0.0168 (6)	0.0224 (6)	0.0212 (7)	0.0004 (5)	−0.0016 (5)	0.0066 (5)
C11A	0.0199 (6)	0.0194 (6)	0.0134 (7)	0.0052 (5)	−0.0004 (5)	0.0051 (5)
C12A	0.0184 (6)	0.0232 (6)	0.0180 (7)	0.0023 (5)	0.0020 (5)	0.0073 (5)
C13A	0.0175 (6)	0.0215 (6)	0.0171 (7)	0.0023 (5)	−0.0012 (5)	0.0055 (5)
C14A	0.0266 (8)	0.0452 (9)	0.0170 (7)	0.0020 (6)	0.0009 (6)	0.0150 (6)
C15A	0.0245 (7)	0.0421 (9)	0.0158 (7)	0.0054 (6)	−0.0025 (6)	0.0124 (6)
O1B	0.0217 (5)	0.0353 (6)	0.0183 (5)	0.0089 (4)	0.0041 (4)	0.0111 (4)
O2B	0.0342 (6)	0.0509 (7)	0.0255 (6)	0.0093 (5)	−0.0065 (5)	0.0158 (5)
O3B	0.0494 (7)	0.0472 (7)	0.0149 (6)	0.0183 (6)	0.0031 (5)	0.0094 (5)
N1B	0.0347 (7)	0.0252 (6)	0.0186 (7)	0.0039 (5)	−0.0035 (5)	0.0081 (5)
N2B	0.0219 (6)	0.0201 (5)	0.0150 (6)	0.0024 (4)	−0.0004 (4)	0.0062 (4)
N3B	0.0192 (6)	0.0340 (6)	0.0160 (6)	0.0058 (5)	0.0017 (5)	0.0099 (5)
C1B	0.0194 (6)	0.0189 (6)	0.0171 (7)	0.0007 (5)	0.0020 (5)	0.0073 (5)
C2B	0.0198 (6)	0.0213 (6)	0.0217 (7)	0.0026 (5)	−0.0014 (5)	0.0093 (5)
C3B	0.0284 (7)	0.0195 (6)	0.0141 (7)	−0.0006 (5)	−0.0029 (6)	0.0059 (5)
C4B	0.0284 (7)	0.0212 (6)	0.0172 (7)	0.0049 (5)	0.0034 (6)	0.0049 (5)
C5B	0.0215 (6)	0.0211 (6)	0.0179 (7)	0.0053 (5)	0.0009 (5)	0.0064 (5)
C6B	0.0206 (6)	0.0156 (6)	0.0169 (7)	0.0001 (5)	−0.0001 (5)	0.0066 (5)
C7B	0.0185 (6)	0.0174 (6)	0.0185 (7)	0.0008 (5)	0.0013 (5)	0.0054 (5)
C8B	0.0190 (6)	0.0161 (6)	0.0177 (7)	0.0000 (5)	−0.0006 (5)	0.0060 (5)
C9B	0.0199 (6)	0.0183 (6)	0.0174 (7)	0.0036 (5)	0.0028 (5)	0.0049 (5)
C10B	0.0179 (6)	0.0203 (6)	0.0195 (7)	0.0046 (5)	−0.0006 (5)	0.0069 (5)
C11B	0.0190 (6)	0.0183 (6)	0.0172 (7)	0.0005 (5)	−0.0012 (5)	0.0069 (5)
C12B	0.0174 (6)	0.0234 (6)	0.0186 (7)	0.0046 (5)	0.0033 (5)	0.0077 (5)
C13B	0.0162 (6)	0.0208 (6)	0.0203 (7)	0.0032 (5)	0.0005 (5)	0.0087 (5)
C14B	0.0273 (7)	0.0424 (9)	0.0168 (7)	0.0085 (6)	0.0036 (6)	0.0112 (6)
C15B	0.0269 (7)	0.0395 (8)	0.0171 (7)	0.0103 (6)	−0.0012 (6)	0.0109 (6)

O1A—C1A	1.3532 (18)	O1B—C1B	1.3545 (17)
O1A—H1A	0.85 (2)	O1B—H1B	0.84 (2)
O2A—N1A	1.2339 (17)	O2B—N1B	1.2357 (18)
O3A—N1A	1.2318 (18)	O3B—N1B	1.2268 (18)
N1A—C3A	1.4566 (18)	N1B—C3B	1.4609 (18)
N2A—C7A	1.2853 (19)	N2B—C7B	1.2827 (18)
N2A—C6A	1.3966 (18)	N2B—C6B	1.4021 (18)
N3A—C11A	1.3596 (19)	N3B—C11B	1.3605 (19)
N3A—C15A	1.4542 (19)	N3B—C15B	1.4535 (18)
N3A—C14A	1.4611 (19)	N3B—C14B	1.4569 (18)
C1A—C2A	1.379 (2)	C1B—C2B	1.382 (2)
C1A—C6A	1.4184 (19)	C1B—C6B	1.4132 (19)
C2A—C3A	1.392 (2)	C2B—C3B	1.387 (2)
C2A—H2AA	0.9500	C2B—H2BA	0.9500
C3A—C4A	1.389 (2)	C3B—C4B	1.391 (2)
C4A—C5A	1.387 (2)	C4B—C5B	1.391 (2)
C4A—H4AA	0.9500	C4B—H4BA	0.9500
C5A—C6A	1.3985 (19)	C5B—C6B	1.3960 (19)
C5A—H5AA	0.9500	C5B—H5BA	0.9500
C7A—C8A	1.441 (2)	C7B—C8B	1.444 (2)
C7A—H7AA	0.9500	C7B—H7BA	0.9500
C8A—C9A	1.4047 (19)	C8B—C9B	1.4002 (19)
C8A—C13A	1.4083 (19)	C8B—C13B	1.4099 (19)
C9A—C10A	1.375 (2)	C9B—C10B	1.378 (2)
C9A—H9AA	0.9500	C9B—H9BA	0.9500
C10A—C11A	1.418 (2)	C10B—C11B	1.4135 (19)
C10A—H10A	0.9500	C10B—H10B	0.9500
C11A—C12A	1.4245 (19)	C11B—C12B	1.4239 (19)
C12A—C13A	1.371 (2)	C12B—C13B	1.372 (2)
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—H13A	0.9500	C13B—H13B	0.9500
C14A—H14A	0.9800	C14B—H14D	0.9800
C14A—H14B	0.9800	C14B—H14E	0.9800
C14A—H14C	0.9800	C14B—H14F	0.9800
C15A—H15A	0.9800	C15B—H15D	0.9800
C15A—H15B	0.9800	C15B—H15E	0.9800
C15A—H15C	0.9800	C15B—H15F	0.9800
C1A—O1A—H1A	102.7 (15)	C1B—O1B—H1B	101.7 (14)
O3A—N1A—O2A	122.88 (13)	O3B—N1B—O2B	123.00 (13)
O3A—N1A—C3A	118.47 (12)	O3B—N1B—C3B	118.68 (12)
O2A—N1A—C3A	118.63 (13)	O2B—N1B—C3B	118.32 (13)
C7A—N2A—C6A	122.31 (12)	C7B—N2B—C6B	122.21 (12)
C11A—N3A—C15A	120.42 (12)	C11B—N3B—C15B	120.50 (12)
C11A—N3A—C14A	121.04 (12)	C11B—N3B—C14B	121.35 (12)
C15A—N3A—C14A	117.87 (12)	C15B—N3B—C14B	118.08 (12)
O1A—C1A—C2A	120.56 (12)	O1B—C1B—C2B	120.39 (12)
O1A—C1A—C6A	117.96 (13)	O1B—C1B—C6B	118.22 (13)
C2A—C1A—C6A	121.48 (13)	C2B—C1B—C6B	121.39 (13)
C1A—C2A—C3A	117.87 (13)	C1B—C2B—C3B	117.73 (13)
C1A—C2A—H2AA	121.1	C1B—C2B—H2BA	121.1
C3A—C2A—H2AA	121.1	C3B—C2B—H2BA	121.1
C4A—C3A—C2A	122.61 (13)	C2B—C3B—C4B	123.07 (13)
C4A—C3A—N1A	119.16 (13)	C2B—C3B—N1B	118.07 (13)
C2A—C3A—N1A	118.22 (12)	C4B—C3B—N1B	118.87 (13)
C5A—C4A—C3A	118.76 (13)	C3B—C4B—C5B	118.20 (13)
C5A—C4A—H4AA	120.6	C3B—C4B—H4BA	120.9
C3A—C4A—H4AA	120.6	C5B—C4B—H4BA	120.9
C4A—C5A—C6A	120.78 (13)	C4B—C5B—C6B	120.85 (13)
C4A—C5A—H5AA	119.6	C4B—C5B—H5BA	119.6
C6A—C5A—H5AA	119.6	C6B—C5B—H5BA	119.6
N2A—C6A—C5A	129.15 (13)	C5B—C6B—N2B	128.86 (12)
N2A—C6A—C1A	112.36 (12)	C5B—C6B—C1B	118.77 (13)
C5A—C6A—C1A	118.49 (13)	N2B—C6B—C1B	112.37 (12)
N2A—C7A—C8A	122.61 (13)	N2B—C7B—C8B	122.64 (13)
N2A—C7A—H7AA	118.7	N2B—C7B—H7BA	118.7
C8A—C7A—H7AA	118.7	C8B—C7B—H7BA	118.7
C9A—C8A—C13A	117.62 (13)	C9B—C8B—C13B	117.45 (13)
C9A—C8A—C7A	120.11 (12)	C9B—C8B—C7B	120.10 (12)
C13A—C8A—C7A	122.28 (12)	C13B—C8B—C7B	122.44 (12)
C10A—C9A—C8A	121.78 (13)	C10B—C9B—C8B	122.06 (13)
C10A—C9A—H9AA	119.1	C10B—C9B—H9BA	119.0
C8A—C9A—H9AA	119.1	C8B—C9B—H9BA	119.0
C9A—C10A—C11A	120.89 (13)	C9B—C10B—C11B	120.62 (12)
C9A—C10A—H10A	119.6	C9B—C10B—H10B	119.7
C11A—C10A—H10A	119.6	C11B—C10B—H10B	119.7
N3A—C11A—C10A	121.71 (13)	N3B—C11B—C10B	121.70 (12)
N3A—C11A—C12A	121.19 (13)	N3B—C11B—C12B	120.93 (12)
C10A—C11A—C12A	117.09 (13)	C10B—C11B—C12B	117.37 (13)
C13A—C12A—C11A	121.23 (13)	C13B—C12B—C11B	121.09 (12)
C13A—C12A—H12A	119.4	C13B—C12B—H12B	119.5
C11A—C12A—H12A	119.4	C11B—C12B—H12B	119.5
C12A—C13A—C8A	121.36 (13)	C12B—C13B—C8B	121.41 (12)
C12A—C13A—H13A	119.3	C12B—C13B—H13B	119.3
C8A—C13A—H13A	119.3	C8B—C13B—H13B	119.3
N3A—C14A—H14A	109.5	N3B—C14B—H14D	109.5
N3A—C14A—H14B	109.5	N3B—C14B—H14E	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
N3A—C14A—H14C	109.5	N3B—C14B—H14F	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5
N3A—C15A—H15A	109.5	N3B—C15B—H15D	109.5
N3A—C15A—H15B	109.5	N3B—C15B—H15E	109.5
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
N3A—C15A—H15C	109.5	N3B—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
O1A—C1A—C2A—C3A	179.99 (12)	O1B—C1B—C2B—C3B	−179.84 (12)
C6A—C1A—C2A—C3A	0.1 (2)	C6B—C1B—C2B—C3B	0.53 (19)
C1A—C2A—C3A—C4A	0.2 (2)	C1B—C2B—C3B—C4B	0.1 (2)
C1A—C2A—C3A—N1A	179.76 (11)	C1B—C2B—C3B—N1B	179.69 (12)
O3A—N1A—C3A—C4A	2.13 (19)	O3B—N1B—C3B—C2B	−174.00 (13)
O2A—N1A—C3A—C4A	−179.11 (13)	O2B—N1B—C3B—C2B	5.6 (2)
O3A—N1A—C3A—C2A	−177.50 (13)	O3B—N1B—C3B—C4B	5.6 (2)
O2A—N1A—C3A—C2A	1.26 (19)	O2B—N1B—C3B—C4B	−174.83 (13)
C2A—C3A—C4A—C5A	0.0 (2)	C2B—C3B—C4B—C5B	−0.6 (2)
N1A—C3A—C4A—C5A	−179.58 (12)	N1B—C3B—C4B—C5B	179.79 (12)
C3A—C4A—C5A—C6A	−0.5 (2)	C3B—C4B—C5B—C6B	0.5 (2)
C7A—N2A—C6A—C5A	−0.7 (2)	C4B—C5B—C6B—N2B	−179.40 (13)
C7A—N2A—C6A—C1A	179.33 (12)	C4B—C5B—C6B—C1B	0.1 (2)
C4A—C5A—C6A—N2A	−179.26 (13)	C7B—N2B—C6B—C5B	−3.0 (2)
C4A—C5A—C6A—C1A	0.7 (2)	C7B—N2B—C6B—C1B	177.45 (12)
O1A—C1A—C6A—N2A	−0.45 (17)	O1B—C1B—C6B—C5B	179.73 (11)
C2A—C1A—C6A—N2A	179.45 (12)	C2B—C1B—C6B—C5B	−0.6 (2)
O1A—C1A—C6A—C5A	179.58 (12)	O1B—C1B—C6B—N2B	−0.71 (17)
C2A—C1A—C6A—C5A	−0.5 (2)	C2B—C1B—C6B—N2B	178.93 (12)
C6A—N2A—C7A—C8A	−179.89 (11)	C6B—N2B—C7B—C8B	−178.80 (11)
N2A—C7A—C8A—C9A	−179.16 (12)	N2B—C7B—C8B—C9B	179.07 (13)
N2A—C7A—C8A—C13A	1.0 (2)	N2B—C7B—C8B—C13B	0.2 (2)
C13A—C8A—C9A—C10A	−0.6 (2)	C13B—C8B—C9B—C10B	−0.6 (2)
C7A—C8A—C9A—C10A	179.49 (12)	C7B—C8B—C9B—C10B	−179.44 (12)
C8A—C9A—C10A—C11A	−0.1 (2)	C8B—C9B—C10B—C11B	−0.3 (2)
C15A—N3A—C11A—C10A	−4.0 (2)	C15B—N3B—C11B—C10B	−0.7 (2)
C14A—N3A—C11A—C10A	−174.38 (13)	C14B—N3B—C11B—C10B	176.16 (13)
C15A—N3A—C11A—C12A	177.25 (13)	C15B—N3B—C11B—C12B	179.00 (13)
C14A—N3A—C11A—C12A	6.9 (2)	C14B—N3B—C11B—C12B	−4.1 (2)
C9A—C10A—C11A—N3A	−177.64 (13)	C9B—C10B—C11B—N3B	−179.46 (12)
C9A—C10A—C11A—C12A	1.2 (2)	C9B—C10B—C11B—C12B	0.80 (19)
N3A—C11A—C12A—C13A	177.30 (12)	N3B—C11B—C12B—C13B	179.83 (12)
C10A—C11A—C12A—C13A	−1.5 (2)	C10B—C11B—C12B—C13B	−0.43 (19)
C11A—C12A—C13A—C8A	0.8 (2)	C11B—C12B—C13B—C8B	−0.5 (2)
C9A—C8A—C13A—C12A	0.29 (19)	C9B—C8B—C13B—C12B	0.94 (19)
C7A—C8A—C13A—C12A	−179.84 (12)	C7B—C8B—C13B—C12B	179.79 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···N2A	0.85 (2)	1.99 (2)	2.5860 (16)	126 (2)
O1A—H1A···O1Ai	0.85 (2)	2.41 (2)	2.8738 (16)	114.7 (19)
O1B—H1B···N2B	0.84 (2)	1.993 (19)	2.5896 (16)	127.5 (19)
O1B—H1B···O1Bii	0.84 (2)	2.45 (2)	2.8853 (15)	113.7 (17)
C7B—H7BA···O1Biii	0.95	2.58	3.1870 (17)	122
C15A—H15C···O3Aiv	0.98	2.59	3.3989 (19)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1A⋯N2A	0.85 (2)	1.99 (2)	2.5860 (16)	126 (2)
O1A—H1A⋯O1A i	0.85 (2)	2.41 (2)	2.8738 (16)	114.7 (19)
O1B—H1B⋯N2B	0.84 (2)	1.993 (19)	2.5896 (16)	127.5 (19)
O1B—H1B⋯O1B ii	0.84 (2)	2.45 (2)	2.8853 (15)	113.7 (17)
C7B—H7BA⋯O1B iii	0.95	2.58	3.1870 (17)	122
C15A—H15C⋯O3A iv	0.98	2.59	3.3989 (19)	141

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