The structural and nonlinear optical properties of a new anilinium hybrid crystal of chemical formula (C
6H
7NCl
+·NO
3−)
3 have been investigated. The crystal structure was determined from single-crystal X-ray diffraction measurements performed at a temperature of 100 K which show that the compound crystallizes in a noncentrosymmetric space group (
Pna2
1). The structural analysis was coupled with Hirshfeld surface analysis to evaluate the contribution of the different intermolecular interactions to the formation of supramolecular assemblies in the solid state that exhibit nonlinear optical features. This analysis reveals that the studied compound is characterized by a three-dimensional network of hydrogen bonds and the main contributions are provided by the O
H, C
H, H
H and Cl
H interactions, which alone represent ∼85% of the total contributions to the Hirshfeld surfaces. It is noteworthy that the halogen
H contributions are quite comparable with those of the H
H contacts. The nonlinear optical properties were investigated by nonlinear diffuse femtosecond-pulse reflectometry and the obtained results were compared with those of the reference material LiNbO
3. The hybrid crystals exhibit notable second (SHG) and third (THG) harmonic generation which confirms its polarity is generated by the different intermolecular interactions. These measurements also highlight that the THG signal of the new anilinium compound normalized to its SHG counterpart is more pronounced than for LiNbO
3.
Supporting information
CCDC reference: 1530349
Data collection: CrysAlis PRO 1.171.38.46 (Rigaku Oxford Diffraction, 2017); cell refinement: CrysAlis PRO 1.171.38.46 (Rigaku Oxford Diffraction, 2017); data reduction: CrysAlis PRO 1.171.38.46 (Rigaku Oxford Diffraction, 2017); program(s) used to solve structure: SHELXS97 (Sheldrick, 2014); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2014); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and and ORTEP-3 for Windows (Farrugia,
1997); software used to prepare material for publication: 'enCIFer (Allen et al., 2004)'.
tri-(o-Chloroanilinium Nitrate
top
Crystal data top
3((C6H7ClN)+·(NO3)−) | Dx = 1.529 Mg m−3 |
Mr = 571.76 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 117559 reflections |
a = 16.8015 (5) Å | θ = 3.0–37.9° |
b = 6.5945 (2) Å | µ = 0.43 mm−1 |
c = 22.4243 (6) Å | T = 100 K |
V = 2484.56 (12) Å3 | Prism, brown |
Z = 4 | 0.22 × 0.18 × 0.14 mm |
F(000) = 1176 | |
Data collection top
SuperNova, Dual, Cu at zero, Atlas diffractometer | 13028 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source | 9377 reflections with I > 2σ(I) |
Detector resolution: 10.4508 pixels mm-1 | Rint = 0.072 |
ω scans | θmax = 37.9°, θmin = 3.0° |
Absorption correction: multi-scan CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | h = −28→28 |
Tmin = 0.826, Tmax = 0.992 | k = −11→11 |
117559 measured reflections | l = −38→38 |
Refinement top
Refinement on F2 | Hydrogen site location: difference Fourier map |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.047 | w = 1/[σ2(Fo2) + (0.0342P)2 + 0.1157P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.099 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.45 e Å−3 |
13028 reflections | Δρmin = −0.38 e Å−3 |
409 parameters | Absolute structure: Flack x determined using 3499 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
1 restraint | Absolute structure parameter: −0.050 (16) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 0.38372 (3) | 0.16209 (7) | 0.24812 (3) | 0.02480 (10) | |
Cl2 | 0.11473 (3) | 0.78871 (9) | 0.41627 (3) | 0.02871 (13) | |
Cl3 | 0.38460 (4) | 0.32023 (10) | 0.58072 (2) | 0.02871 (14) | |
O7 | 0.24503 (8) | 0.62791 (19) | 0.65042 (7) | 0.0190 (3) | |
O6 | 0.24147 (9) | 0.8922 (2) | 0.32153 (7) | 0.0209 (3) | |
O1 | 0.24883 (9) | 0.3831 (2) | 0.47678 (7) | 0.0225 (3) | |
O2 | 0.25547 (9) | 0.0581 (2) | 0.48710 (7) | 0.0236 (3) | |
O4 | 0.25759 (10) | 0.5715 (2) | 0.30643 (7) | 0.0270 (3) | |
O8 | 0.25819 (10) | 0.9537 (2) | 0.64560 (8) | 0.0275 (3) | |
O3 | 0.17049 (9) | 0.2300 (3) | 0.53939 (8) | 0.0284 (4) | |
O5 | 0.32754 (10) | 0.7245 (2) | 0.37433 (8) | 0.0286 (3) | |
O9 | 0.32904 (9) | 0.7808 (2) | 0.70863 (8) | 0.0278 (3) | |
N6 | 0.27838 (10) | 0.7897 (2) | 0.66911 (7) | 0.0166 (3) | |
N4 | 0.22386 (9) | 0.2216 (2) | 0.50211 (7) | 0.0163 (3) | |
N5 | 0.27653 (10) | 0.7290 (3) | 0.33496 (7) | 0.0173 (3) | |
N1 | 0.31848 (10) | 0.2376 (3) | 0.36864 (7) | 0.0168 (3) | |
N2 | 0.18133 (10) | 0.7134 (3) | 0.53670 (8) | 0.0156 (3) | |
N3 | 0.32057 (10) | 0.2974 (3) | 0.70392 (8) | 0.0168 (3) | |
C8 | 0.09461 (11) | 0.7114 (3) | 0.53327 (8) | 0.0152 (3) | |
C15 | 0.45232 (12) | 0.3177 (3) | 0.75138 (12) | 0.0218 (4) | |
C14 | 0.40697 (11) | 0.3123 (3) | 0.69968 (9) | 0.0149 (3) | |
C18 | 0.52529 (14) | 0.3378 (3) | 0.63992 (12) | 0.0282 (5) | |
C1 | 0.44176 (12) | 0.1889 (3) | 0.31153 (9) | 0.0184 (4) | |
C2 | 0.40471 (12) | 0.2229 (3) | 0.36588 (9) | 0.0169 (3) | |
C13 | 0.44297 (12) | 0.3228 (3) | 0.64420 (9) | 0.0192 (4) | |
C6 | 0.52416 (14) | 0.1773 (3) | 0.30787 (12) | 0.0280 (5) | |
C3 | 0.44992 (12) | 0.2439 (3) | 0.41743 (12) | 0.0242 (4) | |
C7 | 0.05730 (12) | 0.7435 (3) | 0.47897 (10) | 0.0204 (4) | |
C4 | 0.53223 (14) | 0.2306 (4) | 0.41372 (15) | 0.0322 (5) | |
C9 | 0.05007 (13) | 0.6738 (3) | 0.58416 (11) | 0.0227 (4) | |
C17 | 0.57056 (13) | 0.3435 (3) | 0.69158 (15) | 0.0338 (6) | |
C10 | −0.03246 (14) | 0.6678 (4) | 0.58037 (14) | 0.0307 (5) | |
C5 | 0.56884 (15) | 0.1985 (4) | 0.35975 (15) | 0.0348 (6) | |
C16 | 0.53468 (13) | 0.3330 (3) | 0.74694 (16) | 0.0304 (5) | |
C12 | −0.02524 (14) | 0.7382 (4) | 0.47510 (13) | 0.0300 (5) | |
C11 | −0.06960 (14) | 0.6990 (4) | 0.52598 (15) | 0.0348 (6) | |
H3A | 0.3037 (15) | 0.183 (4) | 0.6891 (13) | 0.019 (6)* | |
H3C | 0.3067 (16) | 0.294 (4) | 0.7413 (16) | 0.038 (8)* | |
H6 | 0.5497 (15) | 0.151 (4) | 0.2714 (12) | 0.026 (7)* | |
H9 | 0.0758 (15) | 0.654 (4) | 0.6191 (13) | 0.022 (7)* | |
H2B | 0.2008 (15) | 0.614 (4) | 0.5155 (12) | 0.022 (6)* | |
H2C | 0.1949 (16) | 0.696 (4) | 0.5770 (14) | 0.024 (7)* | |
H18 | 0.5470 (15) | 0.349 (4) | 0.6007 (12) | 0.027 (7)* | |
H1C | 0.3026 (16) | 0.332 (4) | 0.3477 (14) | 0.028 (7)* | |
H2A | 0.2001 (16) | 0.832 (4) | 0.5258 (13) | 0.025 (7)* | |
H1A | 0.2971 (16) | 0.126 (4) | 0.3589 (13) | 0.025 (7)* | |
H12 | −0.0468 (16) | 0.763 (4) | 0.4384 (14) | 0.039 (8)* | |
H3B | 0.2973 (14) | 0.393 (4) | 0.6858 (12) | 0.017 (6)* | |
H15 | 0.4295 (16) | 0.306 (4) | 0.7873 (14) | 0.025 (7)* | |
H16 | 0.5629 (17) | 0.337 (4) | 0.7823 (14) | 0.035 (8)* | |
H17 | 0.6259 (19) | 0.367 (5) | 0.6864 (17) | 0.053 (10)* | |
H1B | 0.3026 (16) | 0.268 (4) | 0.4054 (14) | 0.030 (8)* | |
H10 | −0.0601 (17) | 0.644 (4) | 0.6156 (13) | 0.033 (8)* | |
H4 | 0.5598 (16) | 0.241 (5) | 0.4491 (14) | 0.043 (9)* | |
H3 | 0.4244 (15) | 0.264 (4) | 0.4530 (13) | 0.024 (7)* | |
H11 | −0.1288 (19) | 0.685 (5) | 0.5212 (16) | 0.048 (9)* | |
H5 | 0.628 (2) | 0.193 (5) | 0.3552 (18) | 0.065 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0339 (2) | 0.0265 (2) | 0.01404 (15) | −0.00014 (19) | 0.0046 (2) | −0.0021 (2) |
Cl2 | 0.0349 (3) | 0.0370 (3) | 0.0142 (2) | 0.0039 (2) | −0.0042 (2) | 0.0027 (3) |
Cl3 | 0.0369 (3) | 0.0357 (3) | 0.0135 (2) | −0.0016 (2) | 0.0051 (2) | −0.00025 (17) |
O7 | 0.0223 (7) | 0.0158 (6) | 0.0189 (6) | −0.0004 (5) | −0.0060 (5) | −0.0012 (5) |
O6 | 0.0223 (7) | 0.0187 (7) | 0.0216 (7) | 0.0002 (5) | −0.0035 (6) | 0.0027 (5) |
O1 | 0.0299 (8) | 0.0169 (6) | 0.0206 (7) | −0.0003 (5) | 0.0096 (6) | 0.0020 (5) |
O2 | 0.0284 (8) | 0.0170 (7) | 0.0256 (8) | 0.0007 (5) | 0.0066 (6) | −0.0012 (5) |
O4 | 0.0335 (9) | 0.0205 (7) | 0.0271 (8) | 0.0015 (6) | −0.0108 (6) | −0.0045 (6) |
O8 | 0.0342 (9) | 0.0177 (6) | 0.0306 (8) | −0.0018 (6) | −0.0079 (7) | 0.0053 (6) |
O3 | 0.0222 (8) | 0.0343 (9) | 0.0286 (8) | 0.0048 (6) | 0.0137 (6) | 0.0082 (6) |
O5 | 0.0239 (8) | 0.0330 (8) | 0.0290 (8) | 0.0039 (6) | −0.0144 (7) | −0.0030 (6) |
O9 | 0.0235 (8) | 0.0303 (8) | 0.0297 (9) | 0.0012 (6) | −0.0149 (6) | −0.0050 (6) |
N6 | 0.0145 (7) | 0.0177 (7) | 0.0178 (7) | −0.0001 (5) | 0.0007 (6) | −0.0013 (5) |
N4 | 0.0136 (7) | 0.0204 (7) | 0.0148 (7) | −0.0001 (5) | 0.0010 (5) | 0.0022 (5) |
N5 | 0.0161 (8) | 0.0222 (8) | 0.0136 (7) | −0.0007 (6) | −0.0013 (6) | 0.0005 (5) |
N1 | 0.0182 (8) | 0.0196 (8) | 0.0128 (7) | 0.0006 (6) | 0.0023 (6) | −0.0011 (5) |
N2 | 0.0162 (7) | 0.0157 (7) | 0.0149 (7) | 0.0002 (5) | −0.0012 (6) | 0.0004 (5) |
N3 | 0.0164 (7) | 0.0193 (7) | 0.0145 (7) | 0.0005 (5) | 0.0019 (6) | 0.0024 (6) |
C8 | 0.0157 (8) | 0.0141 (7) | 0.0157 (8) | 0.0007 (6) | −0.0005 (6) | −0.0012 (6) |
C15 | 0.0245 (9) | 0.0206 (9) | 0.0202 (9) | 0.0032 (7) | −0.0066 (9) | −0.0012 (8) |
C14 | 0.0138 (8) | 0.0155 (7) | 0.0155 (7) | 0.0000 (6) | 0.0006 (6) | 0.0003 (6) |
C18 | 0.0225 (11) | 0.0211 (10) | 0.0411 (14) | −0.0010 (7) | 0.0139 (9) | 0.0011 (8) |
C1 | 0.0199 (9) | 0.0166 (8) | 0.0187 (8) | 0.0004 (6) | 0.0045 (7) | 0.0004 (6) |
C2 | 0.0171 (9) | 0.0168 (8) | 0.0169 (8) | −0.0002 (6) | 0.0023 (6) | 0.0013 (6) |
C13 | 0.0216 (10) | 0.0177 (8) | 0.0184 (8) | −0.0006 (6) | 0.0063 (7) | −0.0002 (6) |
C6 | 0.0220 (11) | 0.0217 (10) | 0.0403 (13) | 0.0008 (8) | 0.0114 (10) | −0.0010 (8) |
C3 | 0.0251 (10) | 0.0263 (9) | 0.0212 (9) | −0.0029 (8) | −0.0047 (10) | 0.0016 (9) |
C7 | 0.0205 (9) | 0.0215 (9) | 0.0191 (9) | 0.0024 (7) | −0.0044 (7) | −0.0024 (6) |
C4 | 0.0241 (11) | 0.0307 (11) | 0.0418 (15) | −0.0033 (8) | −0.0123 (11) | 0.0006 (11) |
C9 | 0.0228 (10) | 0.0215 (9) | 0.0239 (10) | −0.0010 (7) | 0.0065 (8) | 0.0004 (7) |
C17 | 0.0162 (10) | 0.0230 (10) | 0.0621 (19) | −0.0014 (7) | 0.0003 (11) | 0.0009 (11) |
C10 | 0.0214 (11) | 0.0269 (10) | 0.0436 (15) | −0.0020 (8) | 0.0114 (10) | −0.0014 (9) |
C5 | 0.0156 (10) | 0.0301 (12) | 0.0586 (19) | −0.0005 (8) | 0.0005 (11) | 0.0031 (11) |
C16 | 0.0241 (10) | 0.0225 (10) | 0.0447 (13) | 0.0021 (7) | −0.0131 (12) | −0.0034 (10) |
C12 | 0.0237 (11) | 0.0299 (11) | 0.0363 (13) | 0.0041 (8) | −0.0125 (10) | −0.0054 (9) |
C11 | 0.0158 (10) | 0.0287 (12) | 0.0598 (19) | 0.0000 (8) | 0.0006 (11) | −0.0057 (11) |
Geometric parameters (Å, º) top
Cl1—C1 | 1.733 (2) | C15—C16 | 1.391 (3) |
Cl2—C7 | 1.731 (2) | C15—H15 | 0.90 (3) |
Cl3—C13 | 1.729 (2) | C14—C13 | 1.385 (3) |
O7—N6 | 1.276 (2) | C18—C17 | 1.386 (4) |
O6—N5 | 1.263 (2) | C18—C13 | 1.390 (3) |
O1—N4 | 1.278 (2) | C18—H18 | 0.95 (3) |
O2—N4 | 1.248 (2) | C1—C2 | 1.387 (3) |
O4—N5 | 1.261 (2) | C1—C6 | 1.389 (3) |
O8—N6 | 1.250 (2) | C2—C3 | 1.390 (3) |
O3—N4 | 1.227 (2) | C6—C5 | 1.392 (4) |
O5—N5 | 1.231 (2) | C6—H6 | 0.94 (3) |
O9—N6 | 1.230 (2) | C3—C4 | 1.388 (3) |
N1—C2 | 1.453 (2) | C3—H3 | 0.92 (3) |
N1—H1C | 0.82 (3) | C7—C12 | 1.390 (3) |
N1—H1A | 0.85 (3) | C4—C5 | 1.374 (5) |
N1—H1B | 0.89 (3) | C4—H4 | 0.92 (3) |
N2—C8 | 1.459 (2) | C9—C10 | 1.390 (3) |
N2—H2B | 0.87 (3) | C9—H9 | 0.91 (3) |
N2—H2C | 0.94 (3) | C17—C16 | 1.382 (5) |
N2—H2A | 0.88 (3) | C17—H17 | 0.95 (3) |
N3—C14 | 1.458 (2) | C10—C11 | 1.385 (4) |
N3—H3A | 0.87 (2) | C10—H10 | 0.93 (3) |
N3—H3C | 0.87 (4) | C5—H5 | 0.99 (4) |
N3—H3B | 0.84 (3) | C16—H16 | 0.92 (3) |
C8—C7 | 1.386 (3) | C12—C11 | 1.387 (4) |
C8—C9 | 1.387 (3) | C12—H12 | 0.91 (3) |
C15—C14 | 1.388 (3) | C11—H11 | 1.01 (3) |
| | | |
O9—N6—O8 | 122.19 (17) | C6—C1—Cl1 | 120.45 (17) |
O9—N6—O7 | 120.04 (16) | C1—C2—C3 | 120.1 (2) |
O8—N6—O7 | 117.76 (16) | C1—C2—N1 | 119.72 (18) |
O3—N4—O2 | 122.24 (16) | C3—C2—N1 | 120.17 (18) |
O3—N4—O1 | 120.35 (16) | C14—C13—C18 | 120.0 (2) |
O2—N4—O1 | 117.41 (16) | C14—C13—Cl3 | 119.43 (15) |
O5—N5—O4 | 121.30 (17) | C18—C13—Cl3 | 120.56 (17) |
O5—N5—O6 | 121.10 (17) | C1—C6—C5 | 118.9 (2) |
O4—N5—O6 | 117.60 (16) | C1—C6—H6 | 121.0 (16) |
C2—N1—H1C | 110.4 (19) | C5—C6—H6 | 120.0 (16) |
C2—N1—H1A | 110.6 (18) | C4—C3—C2 | 119.2 (3) |
H1C—N1—H1A | 112 (3) | C4—C3—H3 | 121.9 (17) |
C2—N1—H1B | 110.7 (18) | C2—C3—H3 | 118.9 (17) |
H1C—N1—H1B | 105 (3) | C8—C7—C12 | 120.2 (2) |
H1A—N1—H1B | 108 (3) | C8—C7—Cl2 | 119.20 (15) |
C8—N2—H2B | 109.8 (17) | C12—C7—Cl2 | 120.65 (18) |
C8—N2—H2C | 106.9 (17) | C5—C4—C3 | 120.6 (3) |
H2B—N2—H2C | 110 (2) | C5—C4—H4 | 123.0 (19) |
C8—N2—H2A | 110.6 (18) | C3—C4—H4 | 116.4 (19) |
H2B—N2—H2A | 113 (2) | C8—C9—C10 | 119.5 (2) |
H2C—N2—H2A | 107 (2) | C8—C9—H9 | 118.8 (17) |
C14—N3—H3A | 111.0 (17) | C10—C9—H9 | 121.6 (17) |
C14—N3—H3C | 109.3 (19) | C16—C17—C18 | 120.7 (2) |
H3A—N3—H3C | 105 (3) | C16—C17—H17 | 123 (2) |
C14—N3—H3B | 112.3 (16) | C18—C17—H17 | 116 (2) |
H3A—N3—H3B | 108 (2) | C11—C10—C9 | 119.9 (3) |
H3C—N3—H3B | 111 (2) | C11—C10—H10 | 123.2 (18) |
C7—C8—C9 | 120.41 (19) | C9—C10—H10 | 116.9 (18) |
C7—C8—N2 | 119.77 (17) | C4—C5—C6 | 120.7 (2) |
C9—C8—N2 | 119.81 (18) | C4—C5—H5 | 123 (2) |
C14—C15—C16 | 119.2 (3) | C6—C5—H5 | 117 (2) |
C14—C15—H15 | 120.9 (18) | C17—C16—C15 | 120.1 (3) |
C16—C15—H15 | 119.8 (18) | C17—C16—H16 | 123.0 (19) |
C13—C14—C15 | 120.61 (19) | C15—C16—H16 | 117 (2) |
C13—C14—N3 | 119.79 (17) | C11—C12—C7 | 119.3 (2) |
C15—C14—N3 | 119.60 (18) | C11—C12—H12 | 124.2 (17) |
C17—C18—C13 | 119.4 (2) | C7—C12—H12 | 116.5 (17) |
C17—C18—H18 | 123.9 (16) | C10—C11—C12 | 120.7 (2) |
C13—C18—H18 | 116.7 (16) | C10—C11—H11 | 122 (2) |
C2—C1—C6 | 120.5 (2) | C12—C11—H11 | 117 (2) |
C2—C1—Cl1 | 119.01 (16) | | |
| | | |
C16—C15—C14—C13 | −0.3 (3) | N2—C8—C7—C12 | 178.84 (19) |
C16—C15—C14—N3 | −179.66 (17) | C9—C8—C7—Cl2 | −179.67 (16) |
C6—C1—C2—C3 | −0.6 (3) | N2—C8—C7—Cl2 | −0.8 (3) |
Cl1—C1—C2—C3 | 179.67 (16) | C2—C3—C4—C5 | 0.5 (3) |
C6—C1—C2—N1 | 179.05 (18) | C7—C8—C9—C10 | 0.2 (3) |
Cl1—C1—C2—N1 | −0.7 (2) | N2—C8—C9—C10 | −178.62 (19) |
C15—C14—C13—C18 | 0.3 (3) | C13—C18—C17—C16 | 0.4 (3) |
N3—C14—C13—C18 | 179.74 (17) | C8—C9—C10—C11 | 0.0 (3) |
C15—C14—C13—Cl3 | −178.85 (14) | C3—C4—C5—C6 | −0.5 (4) |
N3—C14—C13—Cl3 | 0.6 (2) | C1—C6—C5—C4 | −0.1 (3) |
C17—C18—C13—C14 | −0.4 (3) | C18—C17—C16—C15 | −0.4 (3) |
C17—C18—C13—Cl3 | 178.75 (16) | C14—C15—C16—C17 | 0.3 (3) |
C2—C1—C6—C5 | 0.6 (3) | C8—C7—C12—C11 | −0.5 (3) |
Cl1—C1—C6—C5 | −179.66 (17) | Cl2—C7—C12—C11 | 179.15 (19) |
C1—C2—C3—C4 | 0.0 (3) | C9—C10—C11—C12 | −0.6 (4) |
N1—C2—C3—C4 | −179.58 (19) | C7—C12—C11—C10 | 0.8 (4) |
C9—C8—C7—C12 | 0.0 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1C···O4 | 0.82 (3) | 1.98 (3) | 2.800 (2) | 173 (3) |
N1—H1A···O6i | 0.85 (3) | 1.99 (3) | 2.825 (2) | 169 (3) |
N1—H1B···O1 | 0.89 (3) | 1.99 (3) | 2.858 (2) | 166 (3) |
N1—H1B···O2 | 0.89 (3) | 2.43 (3) | 3.095 (2) | 132 (2) |
N2—H2B···O1 | 0.87 (3) | 1.93 (3) | 2.799 (2) | 174 (3) |
N2—H2A···O2ii | 0.88 (3) | 1.96 (3) | 2.821 (2) | 166 (3) |
N2—H2C···O7 | 0.94 (3) | 1.90 (3) | 2.823 (2) | 166 (2) |
N2—H2C···O8 | 0.94 (3) | 2.53 (3) | 3.185 (2) | 127 (2) |
N3—H3B···O7 | 0.84 (3) | 1.95 (3) | 2.793 (2) | 175 (2) |
N3—H3A···O8i | 0.87 (2) | 1.96 (3) | 2.819 (2) | 171 (3) |
N3—H3C···O6iii | 0.87 (4) | 2.08 (3) | 2.904 (2) | 159 (2) |
N3—H3C···O4iii | 0.87 (4) | 2.34 (3) | 3.038 (2) | 138 (2) |
Symmetry codes: (i) x, y−1, z; (ii) x−1/2, −y+3/2, z; (iii) −x+1/2, y−1/2, z+1/2. |