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The structures of the two isomeric hydrogen-bonded 1:1 co-crystals of 3-chloro-2-nitro­benzoic acid with 5-nitro­quinoline and 6-nitro­quinoline, and the 1:1 salt of 3-chloro-2-nitro­benzoic acid with 8-hy­droxy­qunoline have been determined at 190 K. In each crystal, the acid and base mol­ecules are linked by a short O—H...N or N—H...O hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019012799/lh5922sup1.cif
Contains datablocks global, I, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989019012799/lh5922Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989019012799/lh5922IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989019012799/lh5922IIIsup4.hkl
Contains datablock III

CCDC references: 1953605; 1953604; 1953603

Key indicators

Structure: I
  • Single-crystal X-ray study
  • T = 190 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.037
  • wR factor = 0.104
  • Data-to-parameter ratio = 19.0
Structure: II
  • Single-crystal X-ray study
  • T = 190 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.039
  • wR factor = 0.113
  • Data-to-parameter ratio = 19.3
Structure: III
  • Single-crystal X-ray study
  • T = 190 K
  • Mean [sigma](C-C) = 0.001 Å
  • R factor = 0.033
  • wR factor = 0.092
  • Data-to-parameter ratio = 19.2

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min). 5 Note
Alert level G PLAT013_ALERT_1_G N.O.K. _shelx_hkl_checksum Found in CIF ...... Please Check PLAT432_ALERT_2_G Short Inter X...Y Contact O3 ..C8 2.95 Ang. 1/2-x,3/2-y,1-z = 7_566 Check PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 6 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 11 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 1 ALERT level C = Check. Ensure it is not caused by an omission or oversight 4 ALERT level G = General information/check it is not something unexpected 1 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Datablock: II
Alert level B PLAT430_ALERT_2_B Short Inter D...A Contact O6 ..N3 . 2.85 Ang. 1-x,-y,1-z = 2_656 Check
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for O5 --N3 . 5.5 s.u. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 Note C7 H4 Cl N O4 PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min). 5 Note
Alert level G PLAT013_ALERT_1_G N.O.K. _shelx_hkl_checksum Found in CIF ...... Please Check PLAT432_ALERT_2_G Short Inter X...Y Contact O6 ..C13 3.02 Ang. 1-x,-y,1-z = 2_656 Check PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 3 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 16 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 3 ALERT level C = Check. Ensure it is not caused by an omission or oversight 4 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Datablock: III

Alert level G PLAT013_ALERT_1_G N.O.K. _shelx_hkl_checksum Found in CIF ...... Please Check PLAT431_ALERT_2_G Short Inter HL..A Contact Cl1 ..O3 . 3.07 Ang. 2-x,1-y,1-z = 3_766 Check PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 4 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 14 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 0 ALERT level C = Check. Ensure it is not caused by an omission or oversight 4 ALERT level G = General information/check it is not something unexpected 1 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

For all structures, data collection: RAPID-AUTO (Rigaku, 2006); cell refinement: RAPID-AUTO (Rigaku, 2006); data reduction: RAPID-AUTO (Rigaku, 2006); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: CrystalStructure (Rigaku, 2018) and PLATON (Spek, 2015).

3-Chloro-2-nitrobenzoic acid–5-nitroquinoline (1/1) (I) top
Crystal data top
C7H4ClNO4·C9H6N2O2F(000) = 1536.00
Mr = 375.72Dx = 1.594 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71075 Å
a = 20.5876 (4) ÅCell parameters from 25710 reflections
b = 7.6889 (3) Åθ = 3.1–30.1°
c = 20.4312 (4) ŵ = 0.29 mm1
β = 104.5338 (7)°T = 190 K
V = 3130.70 (16) Å3Block, colorless
Z = 80.45 × 0.40 × 0.30 mm
Data collection top
Rigaku R-AXIS RAPIDII
diffractometer
4077 reflections with I > 2σ(I)
Detector resolution: 10.000 pixels mm-1Rint = 0.022
ω scansθmax = 30.0°, θmin = 3.1°
Absorption correction: numerical
(NUMABS; Higashi, 1999)
h = 2628
Tmin = 0.837, Tmax = 0.918k = 1010
30107 measured reflectionsl = 2828
4549 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: mixed
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0636P)2 + 1.2587P]
where P = (Fo2 + 2Fc2)/3
4549 reflections(Δ/σ)max = 0.001
239 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.35 e Å3
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
xyzUiso*/Ueq
Cl10.03434 (2)0.24994 (4)0.50043 (2)0.03753 (9)
O10.34832 (4)0.34621 (10)0.61778 (4)0.03292 (17)
O20.27238 (4)0.55880 (10)0.60848 (5)0.03766 (19)
O30.14558 (5)0.57618 (11)0.50150 (4)0.0412 (2)
O40.12329 (5)0.55420 (11)0.59855 (5)0.0414 (2)
O50.64633 (4)0.97971 (11)0.75715 (4)0.03764 (19)
O60.72372 (4)0.82403 (14)0.73078 (5)0.0472 (2)
N10.14396 (4)0.49673 (11)0.55218 (5)0.02666 (17)
N20.43699 (4)0.60692 (11)0.64264 (4)0.02613 (17)
N30.66566 (4)0.84775 (12)0.73417 (4)0.02984 (18)
C10.23369 (5)0.26976 (12)0.58259 (5)0.02307 (18)
C20.16614 (4)0.31430 (12)0.55708 (5)0.02215 (17)
C30.11699 (5)0.18860 (13)0.53478 (5)0.02620 (19)
C40.13470 (5)0.01433 (14)0.53907 (6)0.0320 (2)
H40.1015470.0726330.5239660.038*
C50.20130 (6)0.03225 (14)0.56561 (6)0.0344 (2)
H50.2134410.1517180.5692820.041*
C60.25043 (5)0.09415 (13)0.58689 (6)0.0296 (2)
H60.2958280.0601860.6045240.035*
C70.28632 (5)0.40747 (12)0.60433 (5)0.02479 (18)
C80.41075 (5)0.76300 (13)0.63187 (5)0.0281 (2)
H80.3635280.7728620.6147700.034*
C90.44900 (5)0.91633 (13)0.64438 (5)0.0290 (2)
H90.4279111.0264480.6343820.035*
C100.51692 (5)0.90588 (12)0.67109 (5)0.02615 (19)
H100.5432431.0086300.6804540.031*
C110.54753 (5)0.74008 (11)0.68461 (5)0.02182 (17)
C120.61745 (5)0.70585 (13)0.71097 (5)0.02475 (18)
C130.64371 (5)0.54231 (14)0.71854 (6)0.0311 (2)
H130.6906810.5257410.7353250.037*
C140.60078 (6)0.39830 (14)0.70133 (6)0.0356 (2)
H140.6187480.2838730.7066700.043*
C150.53282 (6)0.42258 (13)0.67677 (6)0.0313 (2)
H150.5040640.3245620.6656990.038*
C160.50536 (5)0.59203 (12)0.66783 (5)0.02310 (18)
H10.3780 (11)0.430 (3)0.6264 (10)0.073 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.02113 (13)0.03817 (16)0.04799 (17)0.00501 (9)0.00126 (11)0.00276 (10)
O10.0197 (3)0.0265 (4)0.0495 (5)0.0024 (3)0.0029 (3)0.0014 (3)
O20.0245 (4)0.0230 (3)0.0615 (5)0.0035 (3)0.0033 (3)0.0040 (3)
O30.0537 (5)0.0289 (4)0.0359 (4)0.0016 (3)0.0018 (4)0.0084 (3)
O40.0421 (5)0.0322 (4)0.0559 (5)0.0007 (3)0.0237 (4)0.0094 (4)
O50.0346 (4)0.0320 (4)0.0431 (4)0.0071 (3)0.0037 (3)0.0078 (3)
O60.0214 (4)0.0566 (6)0.0631 (6)0.0097 (4)0.0097 (4)0.0088 (5)
N10.0211 (4)0.0221 (4)0.0344 (4)0.0018 (3)0.0025 (3)0.0014 (3)
N20.0195 (4)0.0268 (4)0.0299 (4)0.0039 (3)0.0020 (3)0.0007 (3)
N30.0221 (4)0.0337 (4)0.0314 (4)0.0067 (3)0.0022 (3)0.0007 (3)
C10.0209 (4)0.0210 (4)0.0265 (4)0.0031 (3)0.0044 (3)0.0008 (3)
C20.0215 (4)0.0196 (4)0.0248 (4)0.0018 (3)0.0047 (3)0.0002 (3)
C30.0216 (4)0.0260 (4)0.0294 (4)0.0046 (3)0.0036 (3)0.0019 (3)
C40.0300 (5)0.0237 (5)0.0405 (5)0.0075 (4)0.0057 (4)0.0040 (4)
C50.0341 (5)0.0196 (4)0.0477 (6)0.0026 (4)0.0068 (5)0.0018 (4)
C60.0259 (4)0.0221 (4)0.0391 (5)0.0000 (3)0.0050 (4)0.0001 (4)
C70.0200 (4)0.0239 (4)0.0290 (4)0.0032 (3)0.0035 (3)0.0002 (3)
C80.0197 (4)0.0304 (5)0.0321 (5)0.0014 (3)0.0025 (4)0.0042 (4)
C90.0245 (4)0.0241 (4)0.0369 (5)0.0014 (3)0.0053 (4)0.0051 (4)
C100.0230 (4)0.0216 (4)0.0332 (5)0.0019 (3)0.0059 (4)0.0017 (3)
C110.0186 (4)0.0219 (4)0.0243 (4)0.0020 (3)0.0042 (3)0.0004 (3)
C120.0187 (4)0.0275 (4)0.0267 (4)0.0030 (3)0.0032 (3)0.0015 (3)
C130.0223 (4)0.0319 (5)0.0368 (5)0.0049 (4)0.0032 (4)0.0004 (4)
C140.0325 (5)0.0246 (5)0.0470 (6)0.0061 (4)0.0047 (5)0.0010 (4)
C150.0287 (5)0.0218 (4)0.0409 (5)0.0016 (3)0.0038 (4)0.0022 (4)
C160.0203 (4)0.0220 (4)0.0259 (4)0.0027 (3)0.0037 (3)0.0007 (3)
Geometric parameters (Å, º) top
Cl1—C31.7352 (10)C5—C61.3913 (14)
O1—C71.3231 (12)C5—H50.9500
O1—H10.88 (2)C6—H60.9500
O2—C71.2065 (13)C8—C91.4051 (14)
O3—N11.2099 (12)C8—H80.9500
O4—N11.2150 (12)C9—C101.3699 (13)
O5—N31.2256 (13)C9—H90.9500
O6—N31.2282 (12)C10—C111.4182 (13)
N1—C21.4708 (12)C10—H100.9500
N2—C81.3118 (13)C11—C161.4205 (12)
N2—C161.3768 (12)C11—C121.4290 (13)
N3—C121.4711 (13)C12—C131.3621 (14)
C1—C61.3909 (13)C13—C141.4053 (16)
C1—C21.3997 (13)C13—H130.9500
C1—C71.5002 (13)C14—C151.3755 (16)
C2—C31.3909 (12)C14—H140.9500
C3—C41.3857 (14)C15—C161.4138 (13)
C4—C51.3889 (16)C15—H150.9500
C4—H40.9500
C7—O1—H1111.7 (14)O1—C7—C1113.43 (8)
O3—N1—O4125.03 (10)N2—C8—C9123.28 (9)
O3—N1—C2117.71 (9)N2—C8—H8118.4
O4—N1—C2117.21 (9)C9—C8—H8118.4
C8—N2—C16118.56 (8)C10—C9—C8119.51 (9)
O5—N3—O6123.97 (9)C10—C9—H9120.2
O5—N3—C12118.67 (8)C8—C9—H9120.2
O6—N3—C12117.33 (9)C9—C10—C11119.32 (9)
C6—C1—C2117.92 (8)C9—C10—H10120.3
C6—C1—C7121.16 (9)C11—C10—H10120.3
C2—C1—C7120.92 (8)C10—C11—C16117.28 (8)
C3—C2—C1121.68 (9)C10—C11—C12126.54 (8)
C3—C2—N1116.90 (8)C16—C11—C12116.12 (8)
C1—C2—N1121.41 (8)C13—C12—C11123.12 (9)
C4—C3—C2119.53 (9)C13—C12—N3115.57 (9)
C4—C3—Cl1120.28 (7)C11—C12—N3121.28 (9)
C2—C3—Cl1120.18 (8)C12—C13—C14119.48 (9)
C3—C4—C5119.50 (9)C12—C13—H13120.3
C3—C4—H4120.3C14—C13—H13120.3
C5—C4—H4120.3C15—C14—C13120.17 (10)
C4—C5—C6120.72 (10)C15—C14—H14119.9
C4—C5—H5119.6C13—C14—H14119.9
C6—C5—H5119.6C14—C15—C16120.63 (9)
C1—C6—C5120.61 (10)C14—C15—H15119.7
C1—C6—H6119.7C16—C15—H15119.7
C5—C6—H6119.7N2—C16—C15117.59 (8)
O2—C7—O1124.25 (9)N2—C16—C11121.96 (8)
O2—C7—C1122.32 (9)C15—C16—C11120.46 (9)
C6—C1—C2—C31.77 (14)C8—C9—C10—C111.01 (15)
C7—C1—C2—C3178.02 (9)C9—C10—C11—C161.49 (14)
C6—C1—C2—N1178.69 (9)C9—C10—C11—C12178.64 (9)
C7—C1—C2—N11.53 (14)C10—C11—C12—C13175.60 (10)
O3—N1—C2—C392.47 (11)C16—C11—C12—C131.57 (14)
O4—N1—C2—C385.14 (11)C10—C11—C12—N36.67 (15)
O3—N1—C2—C187.09 (12)C16—C11—C12—N3176.16 (8)
O4—N1—C2—C195.29 (11)O5—N3—C12—C13148.03 (10)
C1—C2—C3—C41.39 (15)O6—N3—C12—C1330.14 (14)
N1—C2—C3—C4179.05 (9)O5—N3—C12—C1129.86 (14)
C1—C2—C3—Cl1177.45 (7)O6—N3—C12—C11151.97 (10)
N1—C2—C3—Cl12.11 (12)C11—C12—C13—C141.45 (16)
C2—C3—C4—C50.03 (16)N3—C12—C13—C14176.40 (10)
Cl1—C3—C4—C5178.87 (9)C12—C13—C14—C150.27 (18)
C3—C4—C5—C61.02 (18)C13—C14—C15—C160.68 (18)
C2—C1—C6—C50.76 (16)C8—N2—C16—C15177.79 (10)
C7—C1—C6—C5179.03 (10)C8—N2—C16—C112.30 (14)
C4—C5—C6—C10.62 (18)C14—C15—C16—N2179.60 (10)
C6—C1—C7—O2171.24 (11)C14—C15—C16—C110.50 (16)
C2—C1—C7—O28.99 (15)C10—C11—C16—N23.23 (14)
C6—C1—C7—O19.12 (14)C12—C11—C16—N2179.32 (8)
C2—C1—C7—O1170.66 (9)C10—C11—C16—C15176.87 (9)
C16—N2—C8—C90.41 (16)C12—C11—C16—C150.58 (14)
N2—C8—C9—C102.09 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N20.88 (2)1.80 (2)2.6727 (12)178 (2)
C8—H8···O20.952.483.1820 (13)131
C5—H5···O2i0.952.573.4860 (14)163
C14—H14···O5i0.952.563.4644 (14)159
C13—H13···O6ii0.952.323.1495 (14)146
Symmetry codes: (i) x, y1, z; (ii) x+3/2, y1/2, z+3/2.
3-Chloro-2-nitrobenzoicacid–6-nitroquinoline (1/1) (II) top
Crystal data top
C7H4ClNO4·C9H6N2O2Z = 2
Mr = 375.72F(000) = 384.00
Triclinic, P1Dx = 1.571 Mg m3
a = 7.7282 (10) ÅMo Kα radiation, λ = 0.71075 Å
b = 10.2839 (14) ÅCell parameters from 14524 reflections
c = 11.2828 (16) Åθ = 3.1–30.1°
α = 71.990 (4)°µ = 0.28 mm1
β = 79.724 (4)°T = 190 K
γ = 69.051 (3)°Block, colorless
V = 794.08 (19) Å30.38 × 0.35 × 0.30 mm
Data collection top
Rigaku R-AXIS RAPIDII
diffractometer
4029 reflections with I > 2σ(I)
Detector resolution: 10.000 pixels mm-1Rint = 0.026
ω scansθmax = 30.0°, θmin = 3.1°
Absorption correction: numerical
(NUMABS; Higashi, 1999)
h = 1010
Tmin = 0.887, Tmax = 0.919k = 1414
16549 measured reflectionsl = 1515
4622 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: mixed
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.072P)2 + 0.0976P]
where P = (Fo2 + 2Fc2)/3
4622 reflections(Δ/σ)max = 0.001
239 parametersΔρmax = 0.50 e Å3
0 restraintsΔρmin = 0.33 e Å3
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
xyzUiso*/Ueq
Cl10.21217 (4)1.44247 (3)0.00166 (3)0.04778 (11)
O10.17321 (12)0.77718 (8)0.24868 (9)0.03883 (19)
O20.30609 (12)0.94833 (9)0.20949 (10)0.0464 (2)
O30.23107 (11)1.23134 (10)0.01395 (9)0.0439 (2)
O40.12561 (13)1.25965 (10)0.19770 (10)0.0477 (2)
O50.83957 (13)0.07571 (9)0.45563 (10)0.0469 (2)
O60.58065 (12)0.04120 (8)0.38490 (8)0.03651 (18)
N10.12435 (12)1.22061 (9)0.10689 (9)0.03234 (19)
N20.50541 (13)0.60187 (9)0.31357 (9)0.03239 (19)
N30.69185 (13)0.00332 (9)0.41169 (8)0.03128 (18)
C10.00331 (13)1.01631 (10)0.15345 (9)0.02609 (18)
C20.02570 (12)1.16317 (10)0.10624 (9)0.02667 (18)
C30.18851 (13)1.26120 (10)0.05510 (10)0.0299 (2)
C40.33392 (14)1.21363 (12)0.04976 (10)0.0325 (2)
H40.4458731.2803970.0151460.039*
C50.31344 (14)1.06810 (12)0.09541 (10)0.0318 (2)
H50.4117931.0346960.0919860.038*
C60.14952 (13)0.97031 (11)0.14634 (9)0.02906 (19)
H60.1370310.8705690.1767560.035*
C70.17485 (14)0.91108 (10)0.20737 (10)0.0302 (2)
C80.62786 (17)0.65774 (11)0.32741 (12)0.0382 (2)
H80.5933730.7598630.3093650.046*
C90.80676 (17)0.57424 (13)0.36745 (13)0.0413 (3)
H90.8905180.6196630.3746990.050*
C100.85796 (16)0.42727 (12)0.39567 (12)0.0367 (2)
H100.9770470.3687700.4241930.044*
C110.73037 (14)0.36326 (10)0.38169 (9)0.02805 (19)
C120.77423 (14)0.21193 (10)0.40730 (10)0.02926 (19)
H120.8904520.1480540.4373930.035*
C130.64508 (14)0.16024 (10)0.38761 (9)0.02718 (19)
C140.47039 (14)0.24888 (11)0.34310 (10)0.0302 (2)
H140.3856360.2078830.3296220.036*
C150.42557 (14)0.39522 (11)0.31976 (10)0.0310 (2)
H150.3079260.4570140.2906740.037*
C160.55426 (13)0.45484 (10)0.33887 (9)0.02686 (18)
H10.285 (3)0.723 (3)0.270 (2)0.089 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.03623 (16)0.02349 (14)0.0773 (2)0.00733 (10)0.02054 (14)0.00154 (12)
O10.0321 (4)0.0222 (3)0.0574 (5)0.0076 (3)0.0081 (3)0.0028 (3)
O20.0339 (4)0.0274 (4)0.0765 (6)0.0091 (3)0.0234 (4)0.0020 (4)
O30.0315 (4)0.0410 (4)0.0603 (5)0.0196 (3)0.0013 (4)0.0068 (4)
O40.0429 (5)0.0451 (5)0.0664 (6)0.0136 (4)0.0170 (4)0.0240 (4)
O50.0430 (4)0.0235 (4)0.0679 (6)0.0034 (3)0.0177 (4)0.0047 (4)
O60.0471 (4)0.0304 (4)0.0395 (4)0.0196 (3)0.0002 (3)0.0132 (3)
N10.0246 (4)0.0221 (4)0.0508 (5)0.0070 (3)0.0109 (4)0.0065 (3)
N20.0329 (4)0.0204 (4)0.0417 (5)0.0051 (3)0.0079 (3)0.0066 (3)
N30.0368 (4)0.0225 (4)0.0340 (4)0.0100 (3)0.0023 (3)0.0066 (3)
C10.0231 (4)0.0236 (4)0.0311 (4)0.0078 (3)0.0029 (3)0.0060 (3)
C20.0217 (4)0.0244 (4)0.0349 (4)0.0085 (3)0.0041 (3)0.0071 (3)
C30.0250 (4)0.0238 (4)0.0389 (5)0.0071 (3)0.0065 (4)0.0042 (4)
C40.0220 (4)0.0342 (5)0.0401 (5)0.0080 (4)0.0063 (4)0.0075 (4)
C50.0255 (4)0.0365 (5)0.0374 (5)0.0152 (4)0.0011 (4)0.0099 (4)
C60.0273 (4)0.0282 (4)0.0335 (4)0.0132 (4)0.0008 (3)0.0075 (4)
C70.0287 (4)0.0229 (4)0.0370 (5)0.0068 (3)0.0050 (4)0.0054 (3)
C80.0433 (6)0.0228 (4)0.0506 (6)0.0102 (4)0.0097 (5)0.0097 (4)
C90.0420 (6)0.0310 (5)0.0588 (7)0.0157 (4)0.0144 (5)0.0122 (5)
C100.0328 (5)0.0294 (5)0.0518 (6)0.0100 (4)0.0144 (4)0.0099 (4)
C110.0282 (4)0.0229 (4)0.0343 (5)0.0078 (3)0.0074 (3)0.0071 (3)
C120.0269 (4)0.0218 (4)0.0373 (5)0.0048 (3)0.0091 (4)0.0054 (3)
C130.0303 (4)0.0204 (4)0.0307 (4)0.0082 (3)0.0044 (3)0.0055 (3)
C140.0298 (4)0.0270 (4)0.0359 (5)0.0115 (4)0.0083 (4)0.0055 (4)
C150.0270 (4)0.0258 (4)0.0385 (5)0.0068 (3)0.0103 (4)0.0041 (4)
C160.0275 (4)0.0210 (4)0.0309 (4)0.0064 (3)0.0054 (3)0.0053 (3)
Geometric parameters (Å, º) top
Cl1—C31.7257 (10)C5—C61.3921 (14)
O1—C71.3142 (12)C5—H50.9500
O1—H10.87 (3)C6—H60.9500
O2—C71.2117 (13)C8—C91.4096 (16)
O3—N11.2153 (13)C8—H80.9500
O4—N11.2132 (13)C9—C101.3646 (15)
O5—N31.2243 (12)C9—H90.9500
O6—N31.2244 (12)C10—C111.4193 (14)
N1—C21.4796 (12)C10—H100.9500
N2—C81.3218 (14)C11—C121.4142 (13)
N2—C161.3688 (12)C11—C161.4175 (13)
N3—C131.4682 (12)C12—C131.3637 (14)
C1—C21.3940 (13)C12—H120.9500
C1—C61.3947 (13)C13—C141.4088 (13)
C1—C71.5044 (13)C14—C151.3671 (14)
C2—C31.3873 (13)C14—H140.9500
C3—C41.3934 (13)C15—C161.4163 (14)
C4—C51.3832 (15)C15—H150.9500
C4—H40.9500
C7—O1—H1107.0 (16)O1—C7—C1113.28 (9)
O4—N1—O3125.19 (9)N2—C8—C9123.66 (10)
O4—N1—C2117.34 (9)N2—C8—H8118.2
O3—N1—C2117.37 (9)C9—C8—H8118.2
C8—N2—C16118.54 (9)C10—C9—C8119.08 (10)
O5—N3—O6123.52 (9)C10—C9—H9120.5
O5—N3—C13118.83 (9)C8—C9—H9120.5
O6—N3—C13117.64 (9)C9—C10—C11118.90 (10)
C2—C1—C6117.80 (9)C9—C10—H10120.5
C2—C1—C7120.79 (8)C11—C10—H10120.5
C6—C1—C7121.39 (8)C12—C11—C16119.20 (9)
C3—C2—C1121.41 (9)C12—C11—C10122.22 (9)
C3—C2—N1117.24 (8)C16—C11—C10118.57 (9)
C1—C2—N1121.35 (8)C13—C12—C11118.16 (9)
C2—C3—C4120.06 (9)C13—C12—H12120.9
C2—C3—Cl1120.21 (7)C11—C12—H12120.9
C4—C3—Cl1119.73 (8)C12—C13—C14123.80 (9)
C5—C4—C3119.26 (9)C12—C13—N3118.24 (9)
C5—C4—H4120.4C14—C13—N3117.95 (8)
C3—C4—H4120.4C15—C14—C13118.50 (9)
C4—C5—C6120.36 (9)C15—C14—H14120.8
C4—C5—H5119.8C13—C14—H14120.8
C6—C5—H5119.8C14—C15—C16120.10 (9)
C5—C6—C1121.10 (9)C14—C15—H15120.0
C5—C6—H6119.4C16—C15—H15119.9
C1—C6—H6119.4N2—C16—C15118.54 (9)
O2—C7—O1124.46 (9)N2—C16—C11121.22 (9)
O2—C7—C1122.25 (9)C15—C16—C11120.23 (9)
C6—C1—C2—C30.76 (15)N2—C8—C9—C101.0 (2)
C7—C1—C2—C3179.34 (9)C8—C9—C10—C111.07 (19)
C6—C1—C2—N1178.31 (9)C9—C10—C11—C12179.07 (11)
C7—C1—C2—N10.27 (15)C9—C10—C11—C160.01 (17)
O4—N1—C2—C390.22 (12)C16—C11—C12—C131.04 (15)
O3—N1—C2—C386.34 (12)C10—C11—C12—C13178.04 (10)
O4—N1—C2—C190.67 (12)C11—C12—C13—C140.05 (16)
O3—N1—C2—C192.76 (12)C11—C12—C13—N3178.77 (9)
C1—C2—C3—C40.19 (16)O5—N3—C13—C124.41 (15)
N1—C2—C3—C4178.92 (9)O6—N3—C13—C12174.69 (9)
C1—C2—C3—Cl1179.61 (8)O5—N3—C13—C14176.79 (10)
N1—C2—C3—Cl11.28 (14)O6—N3—C13—C144.11 (14)
C2—C3—C4—C50.26 (16)C12—C13—C14—C150.97 (16)
Cl1—C3—C4—C5179.94 (8)N3—C13—C14—C15179.70 (9)
C3—C4—C5—C60.12 (16)C13—C14—C15—C160.76 (15)
C4—C5—C6—C10.48 (15)C8—N2—C16—C15177.77 (10)
C2—C1—C6—C50.90 (14)C8—N2—C16—C111.38 (15)
C7—C1—C6—C5179.48 (9)C14—C15—C16—N2179.46 (9)
C2—C1—C7—O21.69 (16)C14—C15—C16—C110.30 (15)
C6—C1—C7—O2176.84 (11)C12—C11—C16—N2179.64 (9)
C2—C1—C7—O1179.50 (9)C10—C11—C16—N21.25 (15)
C6—C1—C7—O11.96 (14)C12—C11—C16—C151.22 (15)
C16—N2—C8—C90.26 (18)C10—C11—C16—C15177.89 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N20.87 (3)1.76 (3)2.6310 (14)176 (3)
C8—H8···O20.952.533.2082 (16)128
C8—H8···O6i0.952.413.2387 (15)145
C14—H14···O4ii0.952.523.3226 (16)142
C12—H12···O5iii0.952.373.2526 (16)155
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z; (iii) x+2, y, z+1.
8-Hydroxyquinoliniumb 3-chloro-2-nitrobenzoate (III) top
Crystal data top
C7H3ClNO4·C9H8NOF(000) = 712.00
Mr = 346.73Dx = 1.561 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71075 Å
a = 7.3409 (5) ÅCell parameters from 25520 reflections
b = 7.4689 (4) Åθ = 3.0–30.0°
c = 27.0427 (14) ŵ = 0.29 mm1
β = 95.7158 (19)°T = 190 K
V = 1475.33 (15) Å3Block, pale yellow
Z = 40.45 × 0.30 × 0.26 mm
Data collection top
Rigaku R-AXIS RAPIDII
diffractometer
3937 reflections with I > 2σ(I)
Detector resolution: 10.000 pixels mm-1Rint = 0.019
ω scansθmax = 30.0°, θmin = 3.0°
Absorption correction: numerical
(NUMABS; Higashi, 1999)
h = 1010
Tmin = 0.844, Tmax = 0.927k = 1010
29560 measured reflectionsl = 3737
4311 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: mixed
wR(F2) = 0.092H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0517P)2 + 0.422P]
where P = (Fo2 + 2Fc2)/3
4311 reflections(Δ/σ)max = 0.001
225 parametersΔρmax = 0.39 e Å3
0 restraintsΔρmin = 0.29 e Å3
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
xyzUiso*/Ueq
Cl10.86076 (4)0.71237 (3)0.49827 (2)0.03111 (8)
O10.49893 (14)0.57049 (11)0.27915 (3)0.0388 (2)
O20.50879 (12)0.37292 (10)0.34157 (3)0.03253 (18)
O30.81650 (12)0.34758 (10)0.42238 (3)0.03453 (19)
O40.56116 (14)0.41075 (12)0.45203 (3)0.0406 (2)
O50.25608 (11)0.64218 (10)0.18109 (3)0.03011 (17)
N10.68835 (12)0.44696 (11)0.42827 (3)0.02456 (17)
N20.41002 (11)0.32651 (12)0.21056 (3)0.02279 (16)
C10.63355 (12)0.66248 (12)0.35750 (3)0.02025 (17)
C20.69708 (12)0.62802 (12)0.40684 (3)0.01940 (16)
C30.77981 (12)0.76019 (13)0.43755 (3)0.02089 (17)
C40.80144 (13)0.93180 (13)0.41926 (4)0.02407 (18)
H40.8574611.0227840.4401090.029*
C50.74011 (14)0.96853 (13)0.37014 (4)0.02617 (19)
H50.7547061.0852670.3571500.031*
C60.65741 (13)0.83530 (13)0.33982 (4)0.02399 (18)
H60.6161640.8626930.3062630.029*
C70.53938 (13)0.52246 (13)0.32319 (4)0.02389 (18)
C80.47845 (15)0.17222 (14)0.22785 (4)0.0276 (2)
H80.5307310.1648200.2613640.033*
C90.47520 (16)0.02008 (14)0.19773 (4)0.0314 (2)
H90.5203960.0912260.2107890.038*
C100.40556 (15)0.03461 (14)0.14900 (4)0.0292 (2)
H100.4045560.0673230.1279640.035*
C110.33516 (13)0.19899 (13)0.12955 (4)0.02402 (19)
C120.26151 (15)0.22187 (16)0.07953 (4)0.0303 (2)
H120.2602340.1247670.0568130.036*
C130.19225 (15)0.38479 (17)0.06420 (4)0.0317 (2)
H130.1452740.4001800.0304470.038*
C140.18881 (14)0.53056 (16)0.09724 (4)0.0287 (2)
H140.1384680.6417730.0855980.034*
C150.25798 (13)0.51294 (13)0.14634 (4)0.02325 (18)
C160.33572 (12)0.34640 (13)0.16246 (3)0.02087 (17)
H20.421 (2)0.417 (2)0.2315 (6)0.044 (4)*
H5O0.173 (3)0.722 (2)0.1717 (7)0.049 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.04386 (16)0.02719 (13)0.02051 (12)0.00200 (9)0.00565 (9)0.00222 (8)
O10.0621 (6)0.0278 (4)0.0233 (4)0.0053 (4)0.0116 (3)0.0018 (3)
O20.0403 (4)0.0219 (3)0.0328 (4)0.0084 (3)0.0092 (3)0.0002 (3)
O30.0389 (4)0.0186 (3)0.0436 (5)0.0042 (3)0.0082 (3)0.0010 (3)
O40.0546 (5)0.0327 (4)0.0368 (4)0.0104 (4)0.0154 (4)0.0047 (3)
O50.0389 (4)0.0219 (3)0.0282 (4)0.0071 (3)0.0033 (3)0.0022 (3)
N10.0342 (4)0.0172 (3)0.0211 (4)0.0033 (3)0.0036 (3)0.0004 (3)
N20.0267 (4)0.0202 (4)0.0214 (4)0.0002 (3)0.0019 (3)0.0013 (3)
C10.0217 (4)0.0178 (4)0.0206 (4)0.0009 (3)0.0011 (3)0.0016 (3)
C20.0219 (4)0.0152 (4)0.0208 (4)0.0006 (3)0.0008 (3)0.0002 (3)
C30.0228 (4)0.0187 (4)0.0206 (4)0.0012 (3)0.0007 (3)0.0023 (3)
C40.0256 (4)0.0165 (4)0.0292 (5)0.0006 (3)0.0022 (3)0.0030 (3)
C50.0300 (5)0.0161 (4)0.0315 (5)0.0002 (3)0.0013 (4)0.0023 (3)
C60.0277 (4)0.0194 (4)0.0240 (4)0.0016 (3)0.0016 (3)0.0025 (3)
C70.0263 (4)0.0205 (4)0.0236 (4)0.0007 (3)0.0040 (3)0.0032 (3)
C80.0318 (5)0.0250 (5)0.0259 (4)0.0026 (4)0.0025 (4)0.0029 (4)
C90.0361 (5)0.0219 (5)0.0368 (5)0.0044 (4)0.0066 (4)0.0014 (4)
C100.0321 (5)0.0219 (4)0.0348 (5)0.0013 (4)0.0090 (4)0.0065 (4)
C110.0228 (4)0.0249 (4)0.0249 (4)0.0035 (3)0.0053 (3)0.0040 (3)
C120.0300 (5)0.0367 (6)0.0246 (5)0.0062 (4)0.0042 (4)0.0083 (4)
C130.0289 (5)0.0450 (6)0.0207 (4)0.0029 (4)0.0002 (3)0.0003 (4)
C140.0272 (4)0.0335 (5)0.0251 (5)0.0015 (4)0.0012 (4)0.0054 (4)
C150.0232 (4)0.0229 (4)0.0237 (4)0.0004 (3)0.0024 (3)0.0006 (3)
C160.0202 (4)0.0212 (4)0.0214 (4)0.0019 (3)0.0030 (3)0.0010 (3)
Geometric parameters (Å, º) top
Cl1—C31.7268 (10)C5—C61.3898 (14)
O1—C71.2511 (12)C5—H50.9500
O2—C71.2519 (13)C6—H60.9500
O3—N11.2211 (12)C8—C91.3969 (15)
O4—N11.2154 (12)C8—H80.9500
O5—C151.3483 (12)C9—C101.3695 (16)
O5—H5O0.872 (19)C9—H90.9500
N1—C21.4751 (12)C10—C111.4132 (15)
N2—C81.3236 (13)C10—H100.9500
N2—C161.3676 (12)C11—C161.4154 (13)
N2—H20.880 (16)C11—C121.4161 (14)
C1—C21.3930 (12)C12—C131.3671 (17)
C1—C61.3935 (13)C12—H120.9500
C1—C71.5180 (13)C13—C141.4103 (16)
C2—C31.3902 (12)C13—H130.9500
C3—C41.3887 (13)C14—C151.3798 (14)
C4—C51.3870 (14)C14—H140.9500
C4—H40.9500C15—C161.4189 (13)
C15—O5—H5O109.9 (12)N2—C8—C9121.23 (10)
O4—N1—O3125.17 (9)N2—C8—H8119.4
O4—N1—C2118.51 (9)C9—C8—H8119.4
O3—N1—C2116.22 (9)C10—C9—C8118.66 (10)
C8—N2—C16122.14 (9)C10—C9—H9120.7
C8—N2—H2115.9 (11)C8—C9—H9120.7
C16—N2—H2121.9 (11)C9—C10—C11120.97 (9)
C2—C1—C6117.27 (8)C9—C10—H10119.5
C2—C1—C7123.14 (8)C11—C10—H10119.5
C6—C1—C7119.58 (8)C10—C11—C16117.63 (9)
C3—C2—C1121.72 (8)C10—C11—C12123.44 (9)
C3—C2—N1116.73 (8)C16—C11—C12118.92 (9)
C1—C2—N1121.48 (8)C13—C12—C11119.49 (10)
C4—C3—C2120.08 (9)C13—C12—H12120.3
C4—C3—Cl1119.26 (7)C11—C12—H12120.3
C2—C3—Cl1120.64 (7)C12—C13—C14121.63 (10)
C5—C4—C3119.08 (9)C12—C13—H13119.2
C5—C4—H4120.5C14—C13—H13119.2
C3—C4—H4120.5C15—C14—C13120.53 (10)
C4—C5—C6120.29 (9)C15—C14—H14119.7
C4—C5—H5119.9C13—C14—H14119.7
C6—C5—H5119.9O5—C15—C14125.04 (9)
C5—C6—C1121.56 (9)O5—C15—C16116.43 (8)
C5—C6—H6119.2C14—C15—C16118.52 (9)
C1—C6—H6119.2N2—C16—C11119.30 (9)
O1—C7—O2126.78 (9)N2—C16—C15119.84 (8)
O1—C7—C1115.77 (9)C11—C16—C15120.85 (9)
O2—C7—C1117.44 (8)
C6—C1—C2—C30.47 (14)C16—N2—C8—C91.11 (16)
C7—C1—C2—C3178.81 (9)N2—C8—C9—C102.40 (16)
C6—C1—C2—N1176.32 (8)C8—C9—C10—C111.12 (16)
C7—C1—C2—N14.41 (14)C9—C10—C11—C161.33 (15)
O4—N1—C2—C385.64 (11)C9—C10—C11—C12179.99 (10)
O3—N1—C2—C391.03 (11)C10—C11—C12—C13178.41 (10)
O4—N1—C2—C197.42 (11)C16—C11—C12—C130.23 (14)
O3—N1—C2—C185.91 (11)C11—C12—C13—C141.28 (16)
C1—C2—C3—C40.17 (14)C12—C13—C14—C150.76 (16)
N1—C2—C3—C4176.76 (8)C13—C14—C15—O5177.90 (10)
C1—C2—C3—Cl1178.87 (7)C13—C14—C15—C161.27 (15)
N1—C2—C3—Cl11.94 (12)C8—N2—C16—C111.46 (14)
C2—C3—C4—C50.23 (14)C8—N2—C16—C15177.62 (9)
Cl1—C3—C4—C5178.49 (8)C10—C11—C16—N22.62 (13)
C3—C4—C5—C60.32 (15)C12—C11—C16—N2178.66 (9)
C4—C5—C6—C10.01 (15)C10—C11—C16—C15176.45 (9)
C2—C1—C6—C50.38 (14)C12—C11—C16—C152.27 (14)
C7—C1—C6—C5178.92 (9)O5—C15—C16—N22.60 (13)
C2—C1—C7—O1176.23 (9)C14—C15—C16—N2178.16 (9)
C6—C1—C7—O14.51 (14)O5—C15—C16—C11176.47 (8)
C2—C1—C7—O24.37 (14)C14—C15—C16—C112.77 (14)
C6—C1—C7—O2174.89 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O10.880 (16)1.776 (16)2.6355 (12)164.7 (14)
O5—H5O···O2i0.872 (19)1.756 (19)2.6247 (12)173.2 (19)
C4—H4···O3ii0.952.493.1082 (12)123
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x, y+1, z.
 

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