




Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S205698901500571X/hb7385sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S205698901500571X/hb7385Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S205698901500571X/hb7385Isup3.cml |
CCDC reference: 1055171
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.060
- wR factor = 0.176
- Data-to-parameter ratio = 28.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT242_ALERT_2_C Low Ueq as Compared to Neighbors for ..... N1 Check PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ... -1.917 Report
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 9 Note PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF Please Do ! PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings Differ Please Check PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 5 Note PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL 2014 Note PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ... 1 Report PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 49 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 8 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
The quinoline nucleus is found in many synthetic and natural products having a wide range of pharmacological activities such as anti-viral (Font et al., 1997), and anti-inflammatory (Sloboda et al., 1991) activities.
We herewith report the crystal structure of the title compound (I), (Fig.1). The asymmetric unit of the title compound consists of C9 H8 N O+ cation, C8 H4 N O6- anion and a water molecule. The geometric parameters of the title compound are comparable to the reported structures [Castañeda et al., 2014; Kafka et al., 2012; Li & Chai (2007)]. The benzene ring (C1—C6) of anion makes the dihedral angle of 58.18 (6)° with the quinolinium ring (C9—C12/N2/C13—C17) of cation.
The molecular structure is stabilized by weak intramolecular N—H···O and O—H···O hydrogen bonds (Table 1). The crystal structure is formed by weak intermolecular N—H···O, O—H···O and C—H···O hydrogen bonds (Table 1 & Fig. 2) by linking the adjacent anions and cations by bridging water molecules through O—H···O hydrogen bonds into infinite two-dimensional network along [1 0 0] plane. The crystal structure is further stabilized by weak C—H···π (Table 1) and π–π [Cg1···Cg1i = 3.6507 (9); Cg2···Cg2ii = 3.6507 (9)Å; (i) -x,1-y,1-z; (ii) x,1/2-y,1/2+z; Cg1 and Cg2 are the centroids of the rings (C1—C6) and (N2/C12/C11/C10/C9/C13)] interactions.
The title compound was synthesized by taking at 1:1 ratio of 8-hydroxyquinoline and of 3-nitrophthalic acid was dissolved in a mixed solvent of methanol and water. The salt was formed while adding the base instanstaouly. The solution was stirred for about 2 h to get a homogenous solution. The solution was filtered off and kept aside for slow evaporation at room temperature which yields single crystals suitable for X-ray diffraction.
C-bound H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). H atoms for O atoms were located from Fourier map and refined with O—H = 0.82 (1)Å and Uiso(H) = 1.5 Ueq(O). H atom for N atom was located from Fourier map and refined freely with N—H = 0.88 (1)Å.
The quinoline nucleus is found in many synthetic and natural products having a wide range of pharmacological activities such as anti-viral (Font et al., 1997), and anti-inflammatory (Sloboda et al., 1991) activities.
We herewith report the crystal structure of the title compound (I), (Fig.1). The asymmetric unit of the title compound consists of C9 H8 N O+ cation, C8 H4 N O6- anion and a water molecule. The geometric parameters of the title compound are comparable to the reported structures [Castañeda et al., 2014; Kafka et al., 2012; Li & Chai (2007)]. The benzene ring (C1—C6) of anion makes the dihedral angle of 58.18 (6)° with the quinolinium ring (C9—C12/N2/C13—C17) of cation.
The molecular structure is stabilized by weak intramolecular N—H···O and O—H···O hydrogen bonds (Table 1). The crystal structure is formed by weak intermolecular N—H···O, O—H···O and C—H···O hydrogen bonds (Table 1 & Fig. 2) by linking the adjacent anions and cations by bridging water molecules through O—H···O hydrogen bonds into infinite two-dimensional network along [1 0 0] plane. The crystal structure is further stabilized by weak C—H···π (Table 1) and π–π [Cg1···Cg1i = 3.6507 (9); Cg2···Cg2ii = 3.6507 (9)Å; (i) -x,1-y,1-z; (ii) x,1/2-y,1/2+z; Cg1 and Cg2 are the centroids of the rings (C1—C6) and (N2/C12/C11/C10/C9/C13)] interactions.
For the biological activity of quinoline derivatives, see: Font et al. (1997); Sloboda et al. (1991). For similar structures, see: Castañeda et al. (2014); Kafka et al. (2012); Li & Chai (2007).
The title compound was synthesized by taking at 1:1 ratio of 8-hydroxyquinoline and of 3-nitrophthalic acid was dissolved in a mixed solvent of methanol and water. The salt was formed while adding the base instanstaouly. The solution was stirred for about 2 h to get a homogenous solution. The solution was filtered off and kept aside for slow evaporation at room temperature which yields single crystals suitable for X-ray diffraction.
C-bound H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). H atoms for O atoms were located from Fourier map and refined with O—H = 0.82 (1)Å and Uiso(H) = 1.5 Ueq(O). H atom for N atom was located from Fourier map and refined freely with N—H = 0.88 (1)Å.
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
C9H8NO+·C8H4NO6−·H2O | F(000) = 776 |
Mr = 374.30 | Dx = 1.581 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9900 reflections |
a = 14.4283 (5) Å | θ = 2.8–33.4° |
b = 13.8196 (5) Å | µ = 0.13 mm−1 |
c = 8.0483 (3) Å | T = 295 K |
β = 101.441 (2)° | Block, colourless |
V = 1572.89 (10) Å3 | 0.26 × 0.22 × 0.18 mm |
Z = 4 |
Bruker Kappa APEXII CCD diffractometer | 7431 independent reflections |
Radiation source: fine-focus sealed tube | 4272 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
ω and φ scans | θmax = 36.1°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −23→23 |
Tmin = 0.968, Tmax = 0.977 | k = −19→22 |
58922 measured reflections | l = −13→12 |
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)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.176 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0619P)2 + 0.9848P] where P = (Fo2 + 2Fc2)/3 |
7431 reflections | (Δ/σ)max < 0.001 |
260 parameters | Δρmax = 0.50 e Å−3 |
5 restraints | Δρmin = −0.38 e Å−3 |
C9H8NO+·C8H4NO6−·H2O | V = 1572.89 (10) Å3 |
Mr = 374.30 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.4283 (5) Å | µ = 0.13 mm−1 |
b = 13.8196 (5) Å | T = 295 K |
c = 8.0483 (3) Å | 0.26 × 0.22 × 0.18 mm |
β = 101.441 (2)° |
Bruker Kappa APEXII CCD diffractometer | 7431 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4272 reflections with I > 2σ(I) |
Tmin = 0.968, Tmax = 0.977 | Rint = 0.034 |
58922 measured reflections |
R[F2 > 2σ(F2)] = 0.060 | 5 restraints |
wR(F2) = 0.176 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.50 e Å−3 |
7431 reflections | Δρmin = −0.38 e Å−3 |
260 parameters |
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. |
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 > 2sigma(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 | ||
C1 | 0.17265 (9) | 0.48978 (9) | 0.55989 (18) | 0.0237 (2) | |
C2 | 0.13410 (10) | 0.48988 (10) | 0.70682 (19) | 0.0262 (3) | |
C3 | 0.06506 (11) | 0.42272 (12) | 0.7270 (2) | 0.0331 (3) | |
H3 | 0.0403 | 0.4238 | 0.8252 | 0.040* | |
C4 | 0.03290 (11) | 0.35481 (12) | 0.6037 (2) | 0.0370 (4) | |
H4 | −0.0117 | 0.3091 | 0.6203 | 0.044* | |
C5 | 0.06716 (11) | 0.35508 (12) | 0.4557 (2) | 0.0339 (3) | |
H5 | 0.0449 | 0.3108 | 0.3702 | 0.041* | |
C6 | 0.13531 (10) | 0.42230 (10) | 0.43632 (19) | 0.0267 (3) | |
C7 | 0.24827 (10) | 0.56315 (10) | 0.53939 (18) | 0.0249 (3) | |
C8 | 0.16432 (11) | 0.56359 (11) | 0.84160 (19) | 0.0294 (3) | |
C9 | 0.46422 (11) | 0.34368 (10) | 0.87844 (19) | 0.0288 (3) | |
C10 | 0.53122 (13) | 0.40133 (12) | 0.8201 (2) | 0.0377 (4) | |
H10 | 0.5225 | 0.4680 | 0.8125 | 0.045* | |
C11 | 0.60883 (13) | 0.36137 (14) | 0.7744 (2) | 0.0424 (4) | |
H11 | 0.6521 | 0.4002 | 0.7341 | 0.051* | |
C12 | 0.62252 (11) | 0.26245 (14) | 0.7886 (2) | 0.0390 (4) | |
H12 | 0.6752 | 0.2346 | 0.7575 | 0.047* | |
C13 | 0.48139 (9) | 0.24333 (10) | 0.89029 (18) | 0.0247 (3) | |
C14 | 0.41699 (10) | 0.18003 (10) | 0.94525 (19) | 0.0284 (3) | |
C15 | 0.33963 (11) | 0.21885 (13) | 0.9934 (2) | 0.0364 (3) | |
H15 | 0.2978 | 0.1785 | 1.0346 | 0.044* | |
C16 | 0.32192 (13) | 0.31850 (15) | 0.9818 (2) | 0.0432 (4) | |
H16 | 0.2680 | 0.3428 | 1.0140 | 0.052* | |
C17 | 0.38181 (13) | 0.38061 (12) | 0.9246 (2) | 0.0390 (4) | |
H17 | 0.3685 | 0.4465 | 0.9160 | 0.047* | |
N1 | 0.16655 (10) | 0.42040 (10) | 0.27386 (18) | 0.0337 (3) | |
N2 | 0.56126 (9) | 0.20732 (9) | 0.84612 (17) | 0.0305 (3) | |
H2 | 0.5741 (15) | 0.1450 (8) | 0.866 (3) | 0.047 (6)* | |
O1 | 0.22455 (12) | 0.47889 (11) | 0.24810 (18) | 0.0545 (4) | |
O2 | 0.13344 (13) | 0.35960 (13) | 0.1701 (2) | 0.0684 (5) | |
O3 | 0.33312 (7) | 0.53639 (8) | 0.57868 (15) | 0.0318 (2) | |
O4 | 0.22067 (8) | 0.64521 (8) | 0.49029 (15) | 0.0326 (2) | |
O5 | 0.09894 (10) | 0.57856 (11) | 0.93152 (18) | 0.0465 (3) | |
H5A | 0.1152 (18) | 0.6216 (15) | 1.002 (3) | 0.070* | |
O6 | 0.23875 (9) | 0.60562 (10) | 0.86357 (17) | 0.0435 (3) | |
O7 | 0.43930 (9) | 0.08565 (8) | 0.94455 (17) | 0.0378 (3) | |
H7 | 0.3990 (13) | 0.0519 (15) | 0.981 (3) | 0.057* | |
O8 | 0.13275 (9) | 0.78915 (10) | 0.66412 (16) | 0.0392 (3) | |
H8A | 0.1644 (15) | 0.8061 (18) | 0.7569 (18) | 0.059* | |
H8B | 0.1616 (16) | 0.7423 (13) | 0.635 (3) | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0214 (5) | 0.0215 (5) | 0.0289 (6) | 0.0023 (4) | 0.0070 (5) | 0.0021 (5) |
C2 | 0.0244 (6) | 0.0266 (6) | 0.0286 (7) | 0.0001 (5) | 0.0074 (5) | 0.0023 (5) |
C3 | 0.0308 (7) | 0.0365 (8) | 0.0344 (8) | −0.0042 (6) | 0.0123 (6) | 0.0047 (6) |
C4 | 0.0300 (7) | 0.0364 (8) | 0.0457 (9) | −0.0096 (6) | 0.0101 (7) | 0.0028 (7) |
C5 | 0.0298 (7) | 0.0321 (7) | 0.0395 (8) | −0.0067 (6) | 0.0064 (6) | −0.0041 (6) |
C6 | 0.0244 (6) | 0.0262 (6) | 0.0304 (7) | 0.0012 (5) | 0.0076 (5) | −0.0007 (5) |
C7 | 0.0269 (6) | 0.0238 (6) | 0.0262 (6) | −0.0013 (5) | 0.0109 (5) | −0.0016 (5) |
C8 | 0.0323 (7) | 0.0301 (7) | 0.0269 (7) | 0.0003 (5) | 0.0084 (5) | 0.0024 (5) |
C9 | 0.0337 (7) | 0.0212 (6) | 0.0294 (7) | 0.0003 (5) | 0.0014 (5) | 0.0015 (5) |
C10 | 0.0465 (9) | 0.0239 (7) | 0.0395 (8) | −0.0065 (6) | 0.0006 (7) | 0.0066 (6) |
C11 | 0.0365 (8) | 0.0441 (9) | 0.0449 (10) | −0.0124 (7) | 0.0041 (7) | 0.0152 (8) |
C12 | 0.0267 (7) | 0.0467 (9) | 0.0441 (9) | −0.0008 (6) | 0.0088 (6) | 0.0120 (7) |
C13 | 0.0249 (6) | 0.0221 (6) | 0.0264 (6) | −0.0004 (4) | 0.0034 (5) | 0.0023 (5) |
C14 | 0.0289 (7) | 0.0256 (6) | 0.0303 (7) | −0.0042 (5) | 0.0052 (5) | 0.0017 (5) |
C15 | 0.0316 (7) | 0.0420 (9) | 0.0371 (8) | −0.0043 (6) | 0.0103 (6) | 0.0004 (7) |
C16 | 0.0377 (8) | 0.0510 (10) | 0.0427 (9) | 0.0119 (7) | 0.0126 (7) | −0.0041 (8) |
C17 | 0.0446 (9) | 0.0305 (7) | 0.0415 (9) | 0.0111 (7) | 0.0072 (7) | −0.0023 (7) |
N1 | 0.0339 (7) | 0.0353 (7) | 0.0334 (7) | −0.0031 (5) | 0.0103 (5) | −0.0067 (5) |
N2 | 0.0281 (6) | 0.0267 (6) | 0.0368 (7) | 0.0031 (4) | 0.0069 (5) | 0.0071 (5) |
O1 | 0.0734 (10) | 0.0545 (8) | 0.0431 (7) | −0.0271 (7) | 0.0301 (7) | −0.0107 (6) |
O2 | 0.0782 (11) | 0.0794 (12) | 0.0555 (9) | −0.0402 (9) | 0.0328 (8) | −0.0384 (8) |
O3 | 0.0249 (5) | 0.0287 (5) | 0.0439 (6) | 0.0004 (4) | 0.0122 (4) | −0.0032 (4) |
O4 | 0.0375 (6) | 0.0241 (5) | 0.0365 (6) | 0.0007 (4) | 0.0084 (5) | 0.0031 (4) |
O5 | 0.0434 (7) | 0.0575 (8) | 0.0442 (7) | −0.0089 (6) | 0.0222 (6) | −0.0169 (6) |
O6 | 0.0428 (7) | 0.0496 (7) | 0.0410 (7) | −0.0147 (6) | 0.0153 (5) | −0.0122 (6) |
O7 | 0.0393 (6) | 0.0232 (5) | 0.0537 (7) | −0.0050 (4) | 0.0161 (5) | 0.0044 (5) |
O8 | 0.0429 (7) | 0.0397 (7) | 0.0361 (6) | 0.0043 (5) | 0.0104 (5) | 0.0014 (5) |
C1—C6 | 1.392 (2) | C11—C12 | 1.383 (3) |
C1—C2 | 1.4030 (19) | C11—H11 | 0.9300 |
C1—C7 | 1.5222 (18) | C12—N2 | 1.318 (2) |
C2—C3 | 1.394 (2) | C12—H12 | 0.9300 |
C2—C8 | 1.489 (2) | C13—N2 | 1.3655 (18) |
C3—C4 | 1.378 (2) | C13—C14 | 1.4097 (19) |
C3—H3 | 0.9300 | C14—O7 | 1.3437 (18) |
C4—C5 | 1.377 (2) | C14—C15 | 1.362 (2) |
C4—H4 | 0.9300 | C15—C16 | 1.400 (3) |
C5—C6 | 1.384 (2) | C15—H15 | 0.9300 |
C5—H5 | 0.9300 | C16—C17 | 1.362 (3) |
C6—N1 | 1.4654 (19) | C16—H16 | 0.9300 |
C7—O4 | 1.2404 (17) | C17—H17 | 0.9300 |
C7—O3 | 1.2577 (17) | N1—O1 | 1.2106 (18) |
C8—O6 | 1.2028 (19) | N1—O2 | 1.2137 (19) |
C8—O5 | 1.3142 (19) | N2—H2 | 0.889 (9) |
C9—C10 | 1.403 (2) | O5—H5A | 0.823 (10) |
C9—C13 | 1.4085 (19) | O7—H7 | 0.841 (9) |
C9—C17 | 1.410 (2) | O8—H8A | 0.828 (10) |
C10—C11 | 1.363 (3) | O8—H8B | 0.829 (10) |
C10—H10 | 0.9300 | ||
C6—C1—C2 | 116.16 (12) | C10—C11—C12 | 119.32 (15) |
C6—C1—C7 | 123.58 (12) | C10—C11—H11 | 120.3 |
C2—C1—C7 | 120.21 (12) | C12—C11—H11 | 120.3 |
C3—C2—C1 | 120.61 (14) | N2—C12—C11 | 120.37 (16) |
C3—C2—C8 | 118.90 (13) | N2—C12—H12 | 119.8 |
C1—C2—C8 | 120.46 (12) | C11—C12—H12 | 119.8 |
C4—C3—C2 | 121.06 (14) | N2—C13—C9 | 119.16 (13) |
C4—C3—H3 | 119.5 | N2—C13—C14 | 119.89 (13) |
C2—C3—H3 | 119.5 | C9—C13—C14 | 120.94 (13) |
C5—C4—C3 | 119.59 (14) | O7—C14—C15 | 126.44 (14) |
C5—C4—H4 | 120.2 | O7—C14—C13 | 115.32 (13) |
C3—C4—H4 | 120.2 | C15—C14—C13 | 118.23 (14) |
C4—C5—C6 | 118.98 (15) | C14—C15—C16 | 121.17 (15) |
C4—C5—H5 | 120.5 | C14—C15—H15 | 119.4 |
C6—C5—H5 | 120.5 | C16—C15—H15 | 119.4 |
C5—C6—C1 | 123.52 (14) | C17—C16—C15 | 121.51 (16) |
C5—C6—N1 | 116.10 (13) | C17—C16—H16 | 119.2 |
C1—C6—N1 | 120.38 (12) | C15—C16—H16 | 119.2 |
O4—C7—O3 | 125.72 (13) | C16—C17—C9 | 119.08 (15) |
O4—C7—C1 | 116.86 (12) | C16—C17—H17 | 120.5 |
O3—C7—C1 | 117.37 (12) | C9—C17—H17 | 120.5 |
O6—C8—O5 | 124.10 (15) | O1—N1—O2 | 122.38 (15) |
O6—C8—C2 | 124.14 (14) | O1—N1—C6 | 119.10 (13) |
O5—C8—C2 | 111.75 (13) | O2—N1—C6 | 118.52 (14) |
C10—C9—C13 | 117.26 (14) | C12—N2—C13 | 122.68 (14) |
C10—C9—C17 | 123.74 (14) | C12—N2—H2 | 119.6 (14) |
C13—C9—C17 | 119.00 (14) | C13—N2—H2 | 117.5 (14) |
C11—C10—C9 | 121.17 (15) | C8—O5—H5A | 110.8 (19) |
C11—C10—H10 | 119.4 | C14—O7—H7 | 110.7 (17) |
C9—C10—H10 | 119.4 | H8A—O8—H8B | 105 (2) |
C6—C1—C2—C3 | 2.4 (2) | C9—C10—C11—C12 | −1.1 (3) |
C7—C1—C2—C3 | −179.76 (13) | C10—C11—C12—N2 | −0.1 (3) |
C6—C1—C2—C8 | −175.78 (13) | C10—C9—C13—N2 | 0.3 (2) |
C7—C1—C2—C8 | 2.0 (2) | C17—C9—C13—N2 | −179.84 (14) |
C1—C2—C3—C4 | 0.0 (2) | C10—C9—C13—C14 | −179.04 (14) |
C8—C2—C3—C4 | 178.20 (15) | C17—C9—C13—C14 | 0.8 (2) |
C2—C3—C4—C5 | −2.1 (3) | N2—C13—C14—O7 | −2.0 (2) |
C3—C4—C5—C6 | 1.7 (3) | C9—C13—C14—O7 | 177.38 (14) |
C4—C5—C6—C1 | 0.8 (2) | N2—C13—C14—C15 | 177.96 (14) |
C4—C5—C6—N1 | −178.24 (15) | C9—C13—C14—C15 | −2.7 (2) |
C2—C1—C6—C5 | −2.9 (2) | O7—C14—C15—C16 | −177.32 (17) |
C7—C1—C6—C5 | 179.40 (14) | C13—C14—C15—C16 | 2.8 (2) |
C2—C1—C6—N1 | 176.16 (13) | C14—C15—C16—C17 | −1.0 (3) |
C7—C1—C6—N1 | −1.6 (2) | C15—C16—C17—C9 | −1.0 (3) |
C6—C1—C7—O4 | 96.24 (16) | C10—C9—C17—C16 | −179.12 (17) |
C2—C1—C7—O4 | −81.38 (17) | C13—C9—C17—C16 | 1.0 (2) |
C6—C1—C7—O3 | −85.96 (18) | C5—C6—N1—O1 | 178.42 (16) |
C2—C1—C7—O3 | 96.42 (16) | C1—C6—N1—O1 | −0.7 (2) |
C3—C2—C8—O6 | 157.79 (16) | C5—C6—N1—O2 | −2.0 (2) |
C1—C2—C8—O6 | −24.0 (2) | C1—C6—N1—O2 | 178.93 (17) |
C3—C2—C8—O5 | −23.5 (2) | C11—C12—N2—C13 | 1.5 (3) |
C1—C2—C8—O5 | 154.77 (14) | C9—C13—N2—C12 | −1.6 (2) |
C13—C9—C10—C11 | 1.0 (2) | C14—C13—N2—C12 | 177.75 (15) |
C17—C9—C10—C11 | −178.83 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O3i | 0.89 (1) | 2.00 (1) | 2.8112 (16) | 151 (2) |
O5—H5A···O8ii | 0.82 (1) | 1.78 (1) | 2.5928 (18) | 171 (3) |
O7—H7···O3iii | 0.84 (1) | 1.82 (1) | 2.6482 (15) | 168 (2) |
O8—H8B···O4 | 0.83 (1) | 2.07 (1) | 2.8683 (17) | 163 (2) |
O8—H8A···O4ii | 0.83 (1) | 2.01 (1) | 2.8288 (18) | 170 (2) |
C11—H11···O1iv | 0.93 | 2.42 | 3.295 (2) | 156 |
C12—H12···O6i | 0.93 | 2.48 | 3.343 (2) | 155 |
C16—H16···O2v | 0.93 | 2.52 | 3.413 (2) | 160 |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x, −y+3/2, z+1/2; (iii) x, −y+1/2, z+1/2; (iv) −x+1, −y+1, −z+1; (v) x, y, z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O3i | 0.889 (9) | 2.002 (14) | 2.8112 (16) | 151 (2) |
O5—H5A···O8ii | 0.823 (10) | 1.777 (11) | 2.5928 (18) | 171 (3) |
O7—H7···O3iii | 0.841 (9) | 1.820 (11) | 2.6482 (15) | 168 (2) |
O8—H8B···O4 | 0.829 (10) | 2.067 (12) | 2.8683 (17) | 163 (2) |
O8—H8A···O4ii | 0.828 (10) | 2.009 (11) | 2.8288 (18) | 170 (2) |
C11—H11···O1iv | 0.93 | 2.42 | 3.295 (2) | 156 |
C12—H12···O6i | 0.93 | 2.48 | 3.343 (2) | 155 |
C16—H16···O2v | 0.93 | 2.52 | 3.413 (2) | 160 |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x, −y+3/2, z+1/2; (iii) x, −y+1/2, z+1/2; (iv) −x+1, −y+1, −z+1; (v) x, y, z+1. |