organic compounds
(E)-2-{[4-(Dimethylamino)benzylidene]amino}-5-nitrophenol
aChemistry Department, Morgan State University, 1700 East Cold Spring Lane, Baltimore, MD 21251, USA, bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, and cDepartment of Chemistry, Keene State College, Keene, NH 03410, USA
*Correspondence e-mail: rbutcher99@yahoo.com
The title Schiff base compound, C15H15N3O3, crystallizes with two molecules (A and B) in the Each molecule adopts an E conformation around the C= N imine bond. The two molecules have minor differences in their conformations. In molecule 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 molecule B are 5.7 (1) and 2.45 (6)°, respectively. In each molecule, there is an intramolecular O—H⋯N hydrogen bond. In the crystal, inversion-related molecules 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).
CCDC reference: 997774
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 as anion sensors, see: Hijji et al. (2009), and in non-linear optics, see: Muñoz et al. (2008).
Experimental
Crystal data
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Data collection: CrysAlis PRO (Agilent, 2012); cell 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.
Supporting information
CCDC reference: 997774
10.1107/S160053681400871X/su2709sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681400871X/su2709Isup2.hkl
Supporting information file. DOI: 10.1107/S160053681400871X/su2709Isup3.cml
Schiff bases are used as ligands to form complexes with metals and borane and such complexes have application in non-linear optical dyes (Rodríguez et al., 2012; Reyes et al., 2004) and as anion sensors (Hijji et al., 2009; Muñoz et al. 2008). Related structures were reported by (Gül et al., 2007; Muñoz et al., 2008; Valkonen et al., 2012; Hijji et al., 2014).
The title compound is a Schiff base prepared by the reaction of 4-dimethylaminobenzaldehyde with 2-amino-5-nitrophenol under microwave conditions.It crystallized with two molecules (A and B) in the ═N2A in A and C7B═N2B in B. The two molecules in the have minor differences in their conformations: In molecule A the dihedral angle between the nitro group (N1A/O2A/O3A) and its benzene ring (C1A—C6A) is 2.1 (2)° and between the two benzene rings (C1A—C6A and C8A—C13A) is only 0.88 (7)°, while for molecule B the corresponding angles are 5.7 (1)° and 2.45 (6)°, respectively. For each molecule there is an intramolecular hydrogen bond (Table 1 and Fig. 1) involving the OH group.
Fig. 1. Each molecule adopts an E conformation about the C=N imine bond: C7AIn the crystal, inversion related individual molecules are linked via O—H···O hydrogen bonds forming A—A and B—B dimers (Table 1 and Fig. 2). These dimers are linked via C—H···O hydrogen bonds involving the nitro group O atoms forming -A—A—A- and -B—B—B- slabs that lie parallel to one another and to (010) - see Fig. 3.
In a related 4-nitrophenyl derivative (Hijji et al., 2014) there are no intermolecular C—H···O hydrogen bonds involving the nitro group.
4-dimethaminobenzaldehyde (0.150 g, 1.0 mmol) and 5-nitro-2-amino phenol (0.15 g, 1.0mmol) were placed in a Biotage microwave tube. The mixture was heated in the Biotage initiator microwave for 5 min at 393 K. Upon cooling a brown solid formed. It was dissolved in ethanol and allowed to recrystallize to provide purple crystals (0.20g, 70% yield; M.p. 495-498 K). A sample was recrystallized from ethanol by slow evaporation to provide crystals suitable for X-ray
Spectroscopic data for the title compound is available in the archived CIF.The hydroxyl H atoms were located in a difference Fourier map and freely refined. The C-bound H atoms were placed in calculated positions and treated as riding atoms: C—H = 0.95 and 0.99 Å for CH and CH3 H atoms, respectively, with Uiso(H) = 1.5Ueq(C-methyl) and = 1.2Ueq(C) for other H atoms.
Data collection: CrysAlis PRO (Agilent, 2012); cell
CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); 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 (Sheldrick, 2008).Fig. 1. A view of the molecular structure of the two independent molecules (A and B) of the title compound, with atom labelling. The intramolecular N—H···O hydrogen bonds are shown as dashed lines (see Table 1 for details). | |
Fig. 2. Crystal packing diagram for the title compound viewed along the a axis. The hydrogen bonds are shown as dashed lines (see Table 1 for details). | |
Fig. 3. The -A-A-A- and -B-B-B- slabs that lie parallel to one another and to (010) |
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 |
C15H15N3O3 | γ = 96.033 (4)° |
Mr = 285.30 | V = 1322.37 (13) Å3 |
Triclinic, P1 | Z = 4 |
a = 6.1435 (3) Å | Cu Kα radiation |
b = 14.3844 (8) Å | µ = 0.84 mm−1 |
c = 15.8516 (9) Å | T = 123 K |
α = 108.038 (5)° | 0.32 × 0.24 × 0.19 mm |
β = 91.258 (4)° |
Agilent Xcalibur (Ruby, Gemini) diffractometer | 9056 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | 7791 reflections with I > 2σ(I) |
Tmin = 0.938, Tmax = 1.000 | Rint = 0.034 |
9056 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.119 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.32 e Å−3 |
9056 reflections | Δρmin = −0.21 e Å−3 |
392 parameters |
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 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) x−1, y, z; (iv) x−1, y, z−1. |
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 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) x−1, y, z; (iv) x−1, y, z−1. |
Footnotes
‡Present Address: Department of Chemistry and Earth Sciences, Qatar University, PO Box 2713, Doha, Qatar.
Acknowledgements
YH thanks the Department of Chemistry and Earth Sciences at Qatar University for support. RJB acknowledges the National Science Foundation MRI program (CHE0619278) for funds to purchase the diffractometer and the Howard University Nanoscience Facility for access to liquid nitrogen.
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