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
CCDC references: 1953605; 1953604; 1953603
Key indicators
Structure: I
- Single-crystal X-ray study
- T = 190 K
- Mean
(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
(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
(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
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·C9H6N2O2 | F(000) = 1536.00 |
Mr = 375.72 | Dx = 1.594 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71075 Å |
a = 20.5876 (4) Å | Cell parameters from 25710 reflections |
b = 7.6889 (3) Å | θ = 3.1–30.1° |
c = 20.4312 (4) Å | µ = 0.29 mm−1 |
β = 104.5338 (7)° | T = 190 K |
V = 3130.70 (16) Å3 | Block, colorless |
Z = 8 | 0.45 × 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-1 | Rint = 0.022 |
ω scans | θmax = 30.0°, θmin = 3.1° |
Absorption correction: numerical (NUMABS; Higashi, 1999) | h = −26→28 |
Tmin = 0.837, Tmax = 0.918 | k = −10→10 |
30107 measured reflections | l = −28→28 |
4549 independent reflections | |
Refinement top
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)] = 0.037 | Hydrogen site location: mixed |
wR(F2) = 0.104 | H 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 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
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 | 0.03434 (2) | 0.24994 (4) | 0.50043 (2) | 0.03753 (9) | |
O1 | 0.34832 (4) | 0.34621 (10) | 0.61778 (4) | 0.03292 (17) | |
O2 | 0.27238 (4) | 0.55880 (10) | 0.60848 (5) | 0.03766 (19) | |
O3 | 0.14558 (5) | 0.57618 (11) | 0.50150 (4) | 0.0412 (2) | |
O4 | 0.12329 (5) | 0.55420 (11) | 0.59855 (5) | 0.0414 (2) | |
O5 | 0.64633 (4) | 0.97971 (11) | 0.75715 (4) | 0.03764 (19) | |
O6 | 0.72372 (4) | 0.82403 (14) | 0.73078 (5) | 0.0472 (2) | |
N1 | 0.14396 (4) | 0.49673 (11) | 0.55218 (5) | 0.02666 (17) | |
N2 | 0.43699 (4) | 0.60692 (11) | 0.64264 (4) | 0.02613 (17) | |
N3 | 0.66566 (4) | 0.84775 (12) | 0.73417 (4) | 0.02984 (18) | |
C1 | 0.23369 (5) | 0.26976 (12) | 0.58259 (5) | 0.02307 (18) | |
C2 | 0.16614 (4) | 0.31430 (12) | 0.55708 (5) | 0.02215 (17) | |
C3 | 0.11699 (5) | 0.18860 (13) | 0.53478 (5) | 0.02620 (19) | |
C4 | 0.13470 (5) | 0.01433 (14) | 0.53907 (6) | 0.0320 (2) | |
H4 | 0.101547 | −0.072633 | 0.523966 | 0.038* | |
C5 | 0.20130 (6) | −0.03225 (14) | 0.56561 (6) | 0.0344 (2) | |
H5 | 0.213441 | −0.151718 | 0.569282 | 0.041* | |
C6 | 0.25043 (5) | 0.09415 (13) | 0.58689 (6) | 0.0296 (2) | |
H6 | 0.295828 | 0.060186 | 0.604524 | 0.035* | |
C7 | 0.28632 (5) | 0.40747 (12) | 0.60433 (5) | 0.02479 (18) | |
C8 | 0.41075 (5) | 0.76300 (13) | 0.63187 (5) | 0.0281 (2) | |
H8 | 0.363528 | 0.772862 | 0.614770 | 0.034* | |
C9 | 0.44900 (5) | 0.91633 (13) | 0.64438 (5) | 0.0290 (2) | |
H9 | 0.427911 | 1.026448 | 0.634382 | 0.035* | |
C10 | 0.51692 (5) | 0.90588 (12) | 0.67109 (5) | 0.02615 (19) | |
H10 | 0.543243 | 1.008630 | 0.680454 | 0.031* | |
C11 | 0.54753 (5) | 0.74008 (11) | 0.68461 (5) | 0.02182 (17) | |
C12 | 0.61745 (5) | 0.70585 (13) | 0.71097 (5) | 0.02475 (18) | |
C13 | 0.64371 (5) | 0.54231 (14) | 0.71854 (6) | 0.0311 (2) | |
H13 | 0.690681 | 0.525741 | 0.735325 | 0.037* | |
C14 | 0.60078 (6) | 0.39830 (14) | 0.70133 (6) | 0.0356 (2) | |
H14 | 0.618748 | 0.283873 | 0.706670 | 0.043* | |
C15 | 0.53282 (6) | 0.42258 (13) | 0.67677 (6) | 0.0313 (2) | |
H15 | 0.504064 | 0.324562 | 0.665699 | 0.038* | |
C16 | 0.50536 (5) | 0.59203 (12) | 0.66783 (5) | 0.02310 (18) | |
H1 | 0.3780 (11) | 0.430 (3) | 0.6264 (10) | 0.073 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.02113 (13) | 0.03817 (16) | 0.04799 (17) | −0.00501 (9) | −0.00126 (11) | −0.00276 (10) |
O1 | 0.0197 (3) | 0.0265 (4) | 0.0495 (5) | −0.0024 (3) | 0.0029 (3) | −0.0014 (3) |
O2 | 0.0245 (4) | 0.0230 (3) | 0.0615 (5) | −0.0035 (3) | 0.0033 (3) | −0.0040 (3) |
O3 | 0.0537 (5) | 0.0289 (4) | 0.0359 (4) | 0.0016 (3) | 0.0018 (4) | 0.0084 (3) |
O4 | 0.0421 (5) | 0.0322 (4) | 0.0559 (5) | 0.0007 (3) | 0.0237 (4) | −0.0094 (4) |
O5 | 0.0346 (4) | 0.0320 (4) | 0.0431 (4) | −0.0071 (3) | 0.0037 (3) | −0.0078 (3) |
O6 | 0.0214 (4) | 0.0566 (6) | 0.0631 (6) | −0.0097 (4) | 0.0097 (4) | −0.0088 (5) |
N1 | 0.0211 (4) | 0.0221 (4) | 0.0344 (4) | −0.0018 (3) | 0.0025 (3) | −0.0014 (3) |
N2 | 0.0195 (4) | 0.0268 (4) | 0.0299 (4) | −0.0039 (3) | 0.0020 (3) | 0.0007 (3) |
N3 | 0.0221 (4) | 0.0337 (4) | 0.0314 (4) | −0.0067 (3) | 0.0022 (3) | −0.0007 (3) |
C1 | 0.0209 (4) | 0.0210 (4) | 0.0265 (4) | −0.0031 (3) | 0.0044 (3) | −0.0008 (3) |
C2 | 0.0215 (4) | 0.0196 (4) | 0.0248 (4) | −0.0018 (3) | 0.0047 (3) | −0.0002 (3) |
C3 | 0.0216 (4) | 0.0260 (4) | 0.0294 (4) | −0.0046 (3) | 0.0036 (3) | −0.0019 (3) |
C4 | 0.0300 (5) | 0.0237 (5) | 0.0405 (5) | −0.0075 (4) | 0.0057 (4) | −0.0040 (4) |
C5 | 0.0341 (5) | 0.0196 (4) | 0.0477 (6) | −0.0026 (4) | 0.0068 (5) | −0.0018 (4) |
C6 | 0.0259 (4) | 0.0221 (4) | 0.0391 (5) | 0.0000 (3) | 0.0050 (4) | −0.0001 (4) |
C7 | 0.0200 (4) | 0.0239 (4) | 0.0290 (4) | −0.0032 (3) | 0.0035 (3) | 0.0002 (3) |
C8 | 0.0197 (4) | 0.0304 (5) | 0.0321 (5) | −0.0014 (3) | 0.0025 (4) | 0.0042 (4) |
C9 | 0.0245 (4) | 0.0241 (4) | 0.0369 (5) | 0.0014 (3) | 0.0053 (4) | 0.0051 (4) |
C10 | 0.0230 (4) | 0.0216 (4) | 0.0332 (5) | −0.0019 (3) | 0.0059 (4) | 0.0017 (3) |
C11 | 0.0186 (4) | 0.0219 (4) | 0.0243 (4) | −0.0020 (3) | 0.0042 (3) | −0.0004 (3) |
C12 | 0.0187 (4) | 0.0275 (4) | 0.0267 (4) | −0.0030 (3) | 0.0032 (3) | −0.0015 (3) |
C13 | 0.0223 (4) | 0.0319 (5) | 0.0368 (5) | 0.0049 (4) | 0.0032 (4) | 0.0004 (4) |
C14 | 0.0325 (5) | 0.0246 (5) | 0.0470 (6) | 0.0061 (4) | 0.0047 (5) | −0.0010 (4) |
C15 | 0.0287 (5) | 0.0218 (4) | 0.0409 (5) | −0.0016 (3) | 0.0038 (4) | −0.0022 (4) |
C16 | 0.0203 (4) | 0.0220 (4) | 0.0259 (4) | −0.0027 (3) | 0.0037 (3) | −0.0007 (3) |
Geometric parameters (Å, º) top
Cl1—C3 | 1.7352 (10) | C5—C6 | 1.3913 (14) |
O1—C7 | 1.3231 (12) | C5—H5 | 0.9500 |
O1—H1 | 0.88 (2) | C6—H6 | 0.9500 |
O2—C7 | 1.2065 (13) | C8—C9 | 1.4051 (14) |
O3—N1 | 1.2099 (12) | C8—H8 | 0.9500 |
O4—N1 | 1.2150 (12) | C9—C10 | 1.3699 (13) |
O5—N3 | 1.2256 (13) | C9—H9 | 0.9500 |
O6—N3 | 1.2282 (12) | C10—C11 | 1.4182 (13) |
N1—C2 | 1.4708 (12) | C10—H10 | 0.9500 |
N2—C8 | 1.3118 (13) | C11—C16 | 1.4205 (12) |
N2—C16 | 1.3768 (12) | C11—C12 | 1.4290 (13) |
N3—C12 | 1.4711 (13) | C12—C13 | 1.3621 (14) |
C1—C6 | 1.3909 (13) | C13—C14 | 1.4053 (16) |
C1—C2 | 1.3997 (13) | C13—H13 | 0.9500 |
C1—C7 | 1.5002 (13) | C14—C15 | 1.3755 (16) |
C2—C3 | 1.3909 (12) | C14—H14 | 0.9500 |
C3—C4 | 1.3857 (14) | C15—C16 | 1.4138 (13) |
C4—C5 | 1.3889 (16) | C15—H15 | 0.9500 |
C4—H4 | 0.9500 | | |
| | | |
C7—O1—H1 | 111.7 (14) | O1—C7—C1 | 113.43 (8) |
O3—N1—O4 | 125.03 (10) | N2—C8—C9 | 123.28 (9) |
O3—N1—C2 | 117.71 (9) | N2—C8—H8 | 118.4 |
O4—N1—C2 | 117.21 (9) | C9—C8—H8 | 118.4 |
C8—N2—C16 | 118.56 (8) | C10—C9—C8 | 119.51 (9) |
O5—N3—O6 | 123.97 (9) | C10—C9—H9 | 120.2 |
O5—N3—C12 | 118.67 (8) | C8—C9—H9 | 120.2 |
O6—N3—C12 | 117.33 (9) | C9—C10—C11 | 119.32 (9) |
C6—C1—C2 | 117.92 (8) | C9—C10—H10 | 120.3 |
C6—C1—C7 | 121.16 (9) | C11—C10—H10 | 120.3 |
C2—C1—C7 | 120.92 (8) | C10—C11—C16 | 117.28 (8) |
C3—C2—C1 | 121.68 (9) | C10—C11—C12 | 126.54 (8) |
C3—C2—N1 | 116.90 (8) | C16—C11—C12 | 116.12 (8) |
C1—C2—N1 | 121.41 (8) | C13—C12—C11 | 123.12 (9) |
C4—C3—C2 | 119.53 (9) | C13—C12—N3 | 115.57 (9) |
C4—C3—Cl1 | 120.28 (7) | C11—C12—N3 | 121.28 (9) |
C2—C3—Cl1 | 120.18 (8) | C12—C13—C14 | 119.48 (9) |
C3—C4—C5 | 119.50 (9) | C12—C13—H13 | 120.3 |
C3—C4—H4 | 120.3 | C14—C13—H13 | 120.3 |
C5—C4—H4 | 120.3 | C15—C14—C13 | 120.17 (10) |
C4—C5—C6 | 120.72 (10) | C15—C14—H14 | 119.9 |
C4—C5—H5 | 119.6 | C13—C14—H14 | 119.9 |
C6—C5—H5 | 119.6 | C14—C15—C16 | 120.63 (9) |
C1—C6—C5 | 120.61 (10) | C14—C15—H15 | 119.7 |
C1—C6—H6 | 119.7 | C16—C15—H15 | 119.7 |
C5—C6—H6 | 119.7 | N2—C16—C15 | 117.59 (8) |
O2—C7—O1 | 124.25 (9) | N2—C16—C11 | 121.96 (8) |
O2—C7—C1 | 122.32 (9) | C15—C16—C11 | 120.46 (9) |
| | | |
C6—C1—C2—C3 | −1.77 (14) | C8—C9—C10—C11 | 1.01 (15) |
C7—C1—C2—C3 | 178.02 (9) | C9—C10—C11—C16 | 1.49 (14) |
C6—C1—C2—N1 | 178.69 (9) | C9—C10—C11—C12 | 178.64 (9) |
C7—C1—C2—N1 | −1.53 (14) | C10—C11—C12—C13 | −175.60 (10) |
O3—N1—C2—C3 | −92.47 (11) | C16—C11—C12—C13 | 1.57 (14) |
O4—N1—C2—C3 | 85.14 (11) | C10—C11—C12—N3 | 6.67 (15) |
O3—N1—C2—C1 | 87.09 (12) | C16—C11—C12—N3 | −176.16 (8) |
O4—N1—C2—C1 | −95.29 (11) | O5—N3—C12—C13 | −148.03 (10) |
C1—C2—C3—C4 | 1.39 (15) | O6—N3—C12—C13 | 30.14 (14) |
N1—C2—C3—C4 | −179.05 (9) | O5—N3—C12—C11 | 29.86 (14) |
C1—C2—C3—Cl1 | −177.45 (7) | O6—N3—C12—C11 | −151.97 (10) |
N1—C2—C3—Cl1 | 2.11 (12) | C11—C12—C13—C14 | −1.45 (16) |
C2—C3—C4—C5 | 0.03 (16) | N3—C12—C13—C14 | 176.40 (10) |
Cl1—C3—C4—C5 | 178.87 (9) | C12—C13—C14—C15 | 0.27 (18) |
C3—C4—C5—C6 | −1.02 (18) | C13—C14—C15—C16 | 0.68 (18) |
C2—C1—C6—C5 | 0.76 (16) | C8—N2—C16—C15 | −177.79 (10) |
C7—C1—C6—C5 | −179.03 (10) | C8—N2—C16—C11 | 2.30 (14) |
C4—C5—C6—C1 | 0.62 (18) | C14—C15—C16—N2 | 179.60 (10) |
C6—C1—C7—O2 | −171.24 (11) | C14—C15—C16—C11 | −0.50 (16) |
C2—C1—C7—O2 | 8.99 (15) | C10—C11—C16—N2 | −3.23 (14) |
C6—C1—C7—O1 | 9.12 (14) | C12—C11—C16—N2 | 179.32 (8) |
C2—C1—C7—O1 | −170.66 (9) | C10—C11—C16—C15 | 176.87 (9) |
C16—N2—C8—C9 | 0.41 (16) | C12—C11—C16—C15 | −0.58 (14) |
N2—C8—C9—C10 | −2.09 (17) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2 | 0.88 (2) | 1.80 (2) | 2.6727 (12) | 178 (2) |
C8—H8···O2 | 0.95 | 2.48 | 3.1820 (13) | 131 |
C5—H5···O2i | 0.95 | 2.57 | 3.4860 (14) | 163 |
C14—H14···O5i | 0.95 | 2.56 | 3.4644 (14) | 159 |
C13—H13···O6ii | 0.95 | 2.32 | 3.1495 (14) | 146 |
Symmetry codes: (i) x, y−1, z; (ii) −x+3/2, y−1/2, −z+3/2. |
3-Chloro-2-nitrobenzoicacid–6-nitroquinoline (1/1) (II)
top
Crystal data top
C7H4ClNO4·C9H6N2O2 | Z = 2 |
Mr = 375.72 | F(000) = 384.00 |
Triclinic, P1 | Dx = 1.571 Mg m−3 |
a = 7.7282 (10) Å | Mo Kα radiation, λ = 0.71075 Å |
b = 10.2839 (14) Å | Cell parameters from 14524 reflections |
c = 11.2828 (16) Å | θ = 3.1–30.1° |
α = 71.990 (4)° | µ = 0.28 mm−1 |
β = 79.724 (4)° | T = 190 K |
γ = 69.051 (3)° | Block, colorless |
V = 794.08 (19) Å3 | 0.38 × 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-1 | Rint = 0.026 |
ω scans | θmax = 30.0°, θmin = 3.1° |
Absorption correction: numerical (NUMABS; Higashi, 1999) | h = −10→10 |
Tmin = 0.887, Tmax = 0.919 | k = −14→14 |
16549 measured reflections | l = −15→15 |
4622 independent reflections | |
Refinement top
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)] = 0.039 | Hydrogen site location: mixed |
wR(F2) = 0.113 | H 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 parameters | Δρmax = 0.50 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
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 | −0.21217 (4) | 1.44247 (3) | −0.00166 (3) | 0.04778 (11) | |
O1 | 0.17321 (12) | 0.77718 (8) | 0.24868 (9) | 0.03883 (19) | |
O2 | 0.30609 (12) | 0.94833 (9) | 0.20949 (10) | 0.0464 (2) | |
O3 | 0.23107 (11) | 1.23134 (10) | 0.01395 (9) | 0.0439 (2) | |
O4 | 0.12561 (13) | 1.25965 (10) | 0.19770 (10) | 0.0477 (2) | |
O5 | 0.83957 (13) | −0.07571 (9) | 0.45563 (10) | 0.0469 (2) | |
O6 | 0.58065 (12) | −0.04120 (8) | 0.38490 (8) | 0.03651 (18) | |
N1 | 0.12435 (12) | 1.22061 (9) | 0.10689 (9) | 0.03234 (19) | |
N2 | 0.50541 (13) | 0.60187 (9) | 0.31357 (9) | 0.03239 (19) | |
N3 | 0.69185 (13) | 0.00332 (9) | 0.41169 (8) | 0.03128 (18) | |
C1 | −0.00331 (13) | 1.01631 (10) | 0.15345 (9) | 0.02609 (18) | |
C2 | −0.02570 (12) | 1.16317 (10) | 0.10624 (9) | 0.02667 (18) | |
C3 | −0.18851 (13) | 1.26120 (10) | 0.05510 (10) | 0.0299 (2) | |
C4 | −0.33392 (14) | 1.21363 (12) | 0.04976 (10) | 0.0325 (2) | |
H4 | −0.445873 | 1.280397 | 0.015146 | 0.039* | |
C5 | −0.31344 (14) | 1.06810 (12) | 0.09541 (10) | 0.0318 (2) | |
H5 | −0.411793 | 1.034696 | 0.091986 | 0.038* | |
C6 | −0.14952 (13) | 0.97031 (11) | 0.14634 (9) | 0.02906 (19) | |
H6 | −0.137031 | 0.870569 | 0.176756 | 0.035* | |
C7 | 0.17485 (14) | 0.91108 (10) | 0.20737 (10) | 0.0302 (2) | |
C8 | 0.62786 (17) | 0.65774 (11) | 0.32741 (12) | 0.0382 (2) | |
H8 | 0.593373 | 0.759863 | 0.309365 | 0.046* | |
C9 | 0.80676 (17) | 0.57424 (13) | 0.36745 (13) | 0.0413 (3) | |
H9 | 0.890518 | 0.619663 | 0.374699 | 0.050* | |
C10 | 0.85796 (16) | 0.42727 (12) | 0.39567 (12) | 0.0367 (2) | |
H10 | 0.977047 | 0.368770 | 0.424193 | 0.044* | |
C11 | 0.73037 (14) | 0.36326 (10) | 0.38169 (9) | 0.02805 (19) | |
C12 | 0.77423 (14) | 0.21193 (10) | 0.40730 (10) | 0.02926 (19) | |
H12 | 0.890452 | 0.148054 | 0.437393 | 0.035* | |
C13 | 0.64508 (14) | 0.16024 (10) | 0.38761 (9) | 0.02718 (19) | |
C14 | 0.47039 (14) | 0.24888 (11) | 0.34310 (10) | 0.0302 (2) | |
H14 | 0.385636 | 0.207883 | 0.329622 | 0.036* | |
C15 | 0.42557 (14) | 0.39522 (11) | 0.31976 (10) | 0.0310 (2) | |
H15 | 0.307926 | 0.457014 | 0.290674 | 0.037* | |
C16 | 0.55426 (13) | 0.45484 (10) | 0.33887 (9) | 0.02686 (18) | |
H1 | 0.285 (3) | 0.723 (3) | 0.270 (2) | 0.089 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.03623 (16) | 0.02349 (14) | 0.0773 (2) | −0.00733 (10) | −0.02054 (14) | 0.00154 (12) |
O1 | 0.0321 (4) | 0.0222 (3) | 0.0574 (5) | −0.0076 (3) | −0.0081 (3) | −0.0028 (3) |
O2 | 0.0339 (4) | 0.0274 (4) | 0.0765 (6) | −0.0091 (3) | −0.0234 (4) | −0.0020 (4) |
O3 | 0.0315 (4) | 0.0410 (4) | 0.0603 (5) | −0.0196 (3) | −0.0013 (4) | −0.0068 (4) |
O4 | 0.0429 (5) | 0.0451 (5) | 0.0664 (6) | −0.0136 (4) | −0.0170 (4) | −0.0240 (4) |
O5 | 0.0430 (4) | 0.0235 (4) | 0.0679 (6) | −0.0034 (3) | −0.0177 (4) | −0.0047 (4) |
O6 | 0.0471 (4) | 0.0304 (4) | 0.0395 (4) | −0.0196 (3) | −0.0002 (3) | −0.0132 (3) |
N1 | 0.0246 (4) | 0.0221 (4) | 0.0508 (5) | −0.0070 (3) | −0.0109 (4) | −0.0065 (3) |
N2 | 0.0329 (4) | 0.0204 (4) | 0.0417 (5) | −0.0051 (3) | −0.0079 (3) | −0.0066 (3) |
N3 | 0.0368 (4) | 0.0225 (4) | 0.0340 (4) | −0.0100 (3) | −0.0023 (3) | −0.0066 (3) |
C1 | 0.0231 (4) | 0.0236 (4) | 0.0311 (4) | −0.0078 (3) | −0.0029 (3) | −0.0060 (3) |
C2 | 0.0217 (4) | 0.0244 (4) | 0.0349 (4) | −0.0085 (3) | −0.0041 (3) | −0.0071 (3) |
C3 | 0.0250 (4) | 0.0238 (4) | 0.0389 (5) | −0.0071 (3) | −0.0065 (4) | −0.0042 (4) |
C4 | 0.0220 (4) | 0.0342 (5) | 0.0401 (5) | −0.0080 (4) | −0.0063 (4) | −0.0075 (4) |
C5 | 0.0255 (4) | 0.0365 (5) | 0.0374 (5) | −0.0152 (4) | −0.0011 (4) | −0.0099 (4) |
C6 | 0.0273 (4) | 0.0282 (4) | 0.0335 (4) | −0.0132 (4) | 0.0008 (3) | −0.0075 (4) |
C7 | 0.0287 (4) | 0.0229 (4) | 0.0370 (5) | −0.0068 (3) | −0.0050 (4) | −0.0054 (3) |
C8 | 0.0433 (6) | 0.0228 (4) | 0.0506 (6) | −0.0102 (4) | −0.0097 (5) | −0.0097 (4) |
C9 | 0.0420 (6) | 0.0310 (5) | 0.0588 (7) | −0.0157 (4) | −0.0144 (5) | −0.0122 (5) |
C10 | 0.0328 (5) | 0.0294 (5) | 0.0518 (6) | −0.0100 (4) | −0.0144 (4) | −0.0099 (4) |
C11 | 0.0282 (4) | 0.0229 (4) | 0.0343 (5) | −0.0078 (3) | −0.0074 (3) | −0.0071 (3) |
C12 | 0.0269 (4) | 0.0218 (4) | 0.0373 (5) | −0.0048 (3) | −0.0091 (4) | −0.0054 (3) |
C13 | 0.0303 (4) | 0.0204 (4) | 0.0307 (4) | −0.0082 (3) | −0.0044 (3) | −0.0055 (3) |
C14 | 0.0298 (4) | 0.0270 (4) | 0.0359 (5) | −0.0115 (4) | −0.0083 (4) | −0.0055 (4) |
C15 | 0.0270 (4) | 0.0258 (4) | 0.0385 (5) | −0.0068 (3) | −0.0103 (4) | −0.0041 (4) |
C16 | 0.0275 (4) | 0.0210 (4) | 0.0309 (4) | −0.0064 (3) | −0.0054 (3) | −0.0053 (3) |
Geometric parameters (Å, º) top
Cl1—C3 | 1.7257 (10) | C5—C6 | 1.3921 (14) |
O1—C7 | 1.3142 (12) | C5—H5 | 0.9500 |
O1—H1 | 0.87 (3) | C6—H6 | 0.9500 |
O2—C7 | 1.2117 (13) | C8—C9 | 1.4096 (16) |
O3—N1 | 1.2153 (13) | C8—H8 | 0.9500 |
O4—N1 | 1.2132 (13) | C9—C10 | 1.3646 (15) |
O5—N3 | 1.2243 (12) | C9—H9 | 0.9500 |
O6—N3 | 1.2244 (12) | C10—C11 | 1.4193 (14) |
N1—C2 | 1.4796 (12) | C10—H10 | 0.9500 |
N2—C8 | 1.3218 (14) | C11—C12 | 1.4142 (13) |
N2—C16 | 1.3688 (12) | C11—C16 | 1.4175 (13) |
N3—C13 | 1.4682 (12) | C12—C13 | 1.3637 (14) |
C1—C2 | 1.3940 (13) | C12—H12 | 0.9500 |
C1—C6 | 1.3947 (13) | C13—C14 | 1.4088 (13) |
C1—C7 | 1.5044 (13) | C14—C15 | 1.3671 (14) |
C2—C3 | 1.3873 (13) | C14—H14 | 0.9500 |
C3—C4 | 1.3934 (13) | C15—C16 | 1.4163 (14) |
C4—C5 | 1.3832 (15) | C15—H15 | 0.9500 |
C4—H4 | 0.9500 | | |
| | | |
C7—O1—H1 | 107.0 (16) | O1—C7—C1 | 113.28 (9) |
O4—N1—O3 | 125.19 (9) | N2—C8—C9 | 123.66 (10) |
O4—N1—C2 | 117.34 (9) | N2—C8—H8 | 118.2 |
O3—N1—C2 | 117.37 (9) | C9—C8—H8 | 118.2 |
C8—N2—C16 | 118.54 (9) | C10—C9—C8 | 119.08 (10) |
O5—N3—O6 | 123.52 (9) | C10—C9—H9 | 120.5 |
O5—N3—C13 | 118.83 (9) | C8—C9—H9 | 120.5 |
O6—N3—C13 | 117.64 (9) | C9—C10—C11 | 118.90 (10) |
C2—C1—C6 | 117.80 (9) | C9—C10—H10 | 120.5 |
C2—C1—C7 | 120.79 (8) | C11—C10—H10 | 120.5 |
C6—C1—C7 | 121.39 (8) | C12—C11—C16 | 119.20 (9) |
C3—C2—C1 | 121.41 (9) | C12—C11—C10 | 122.22 (9) |
C3—C2—N1 | 117.24 (8) | C16—C11—C10 | 118.57 (9) |
C1—C2—N1 | 121.35 (8) | C13—C12—C11 | 118.16 (9) |
C2—C3—C4 | 120.06 (9) | C13—C12—H12 | 120.9 |
C2—C3—Cl1 | 120.21 (7) | C11—C12—H12 | 120.9 |
C4—C3—Cl1 | 119.73 (8) | C12—C13—C14 | 123.80 (9) |
C5—C4—C3 | 119.26 (9) | C12—C13—N3 | 118.24 (9) |
C5—C4—H4 | 120.4 | C14—C13—N3 | 117.95 (8) |
C3—C4—H4 | 120.4 | C15—C14—C13 | 118.50 (9) |
C4—C5—C6 | 120.36 (9) | C15—C14—H14 | 120.8 |
C4—C5—H5 | 119.8 | C13—C14—H14 | 120.8 |
C6—C5—H5 | 119.8 | C14—C15—C16 | 120.10 (9) |
C5—C6—C1 | 121.10 (9) | C14—C15—H15 | 120.0 |
C5—C6—H6 | 119.4 | C16—C15—H15 | 119.9 |
C1—C6—H6 | 119.4 | N2—C16—C15 | 118.54 (9) |
O2—C7—O1 | 124.46 (9) | N2—C16—C11 | 121.22 (9) |
O2—C7—C1 | 122.25 (9) | C15—C16—C11 | 120.23 (9) |
| | | |
C6—C1—C2—C3 | 0.76 (15) | N2—C8—C9—C10 | −1.0 (2) |
C7—C1—C2—C3 | 179.34 (9) | C8—C9—C10—C11 | 1.07 (19) |
C6—C1—C2—N1 | −178.31 (9) | C9—C10—C11—C12 | 179.07 (11) |
C7—C1—C2—N1 | 0.27 (15) | C9—C10—C11—C16 | −0.01 (17) |
O4—N1—C2—C3 | 90.22 (12) | C16—C11—C12—C13 | 1.04 (15) |
O3—N1—C2—C3 | −86.34 (12) | C10—C11—C12—C13 | −178.04 (10) |
O4—N1—C2—C1 | −90.67 (12) | C11—C12—C13—C14 | 0.05 (16) |
O3—N1—C2—C1 | 92.76 (12) | C11—C12—C13—N3 | 178.77 (9) |
C1—C2—C3—C4 | −0.19 (16) | O5—N3—C13—C12 | 4.41 (15) |
N1—C2—C3—C4 | 178.92 (9) | O6—N3—C13—C12 | −174.69 (9) |
C1—C2—C3—Cl1 | 179.61 (8) | O5—N3—C13—C14 | −176.79 (10) |
N1—C2—C3—Cl1 | −1.28 (14) | O6—N3—C13—C14 | 4.11 (14) |
C2—C3—C4—C5 | −0.26 (16) | C12—C13—C14—C15 | −0.97 (16) |
Cl1—C3—C4—C5 | 179.94 (8) | N3—C13—C14—C15 | −179.70 (9) |
C3—C4—C5—C6 | 0.12 (16) | C13—C14—C15—C16 | 0.76 (15) |
C4—C5—C6—C1 | 0.48 (15) | C8—N2—C16—C15 | −177.77 (10) |
C2—C1—C6—C5 | −0.90 (14) | C8—N2—C16—C11 | 1.38 (15) |
C7—C1—C6—C5 | −179.48 (9) | C14—C15—C16—N2 | 179.46 (9) |
C2—C1—C7—O2 | −1.69 (16) | C14—C15—C16—C11 | 0.30 (15) |
C6—C1—C7—O2 | 176.84 (11) | C12—C11—C16—N2 | 179.64 (9) |
C2—C1—C7—O1 | 179.50 (9) | C10—C11—C16—N2 | −1.25 (15) |
C6—C1—C7—O1 | −1.96 (14) | C12—C11—C16—C15 | −1.22 (15) |
C16—N2—C8—C9 | −0.26 (18) | C10—C11—C16—C15 | 177.89 (10) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2 | 0.87 (3) | 1.76 (3) | 2.6310 (14) | 176 (3) |
C8—H8···O2 | 0.95 | 2.53 | 3.2082 (16) | 128 |
C8—H8···O6i | 0.95 | 2.41 | 3.2387 (15) | 145 |
C14—H14···O4ii | 0.95 | 2.52 | 3.3226 (16) | 142 |
C12—H12···O5iii | 0.95 | 2.37 | 3.2526 (16) | 155 |
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z; (iii) −x+2, −y, −z+1. |
8-Hydroxyquinoliniumb 3-chloro-2-nitrobenzoate (III)
top
Crystal data top
C7H3ClNO4·C9H8NO | F(000) = 712.00 |
Mr = 346.73 | Dx = 1.561 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71075 Å |
a = 7.3409 (5) Å | Cell parameters from 25520 reflections |
b = 7.4689 (4) Å | θ = 3.0–30.0° |
c = 27.0427 (14) Å | µ = 0.29 mm−1 |
β = 95.7158 (19)° | T = 190 K |
V = 1475.33 (15) Å3 | Block, pale yellow |
Z = 4 | 0.45 × 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-1 | Rint = 0.019 |
ω scans | θmax = 30.0°, θmin = 3.0° |
Absorption correction: numerical (NUMABS; Higashi, 1999) | h = −10→10 |
Tmin = 0.844, Tmax = 0.927 | k = −10→10 |
29560 measured reflections | l = −37→37 |
4311 independent reflections | |
Refinement top
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)] = 0.033 | Hydrogen site location: mixed |
wR(F2) = 0.092 | H 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 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
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 | 0.86076 (4) | 0.71237 (3) | 0.49827 (2) | 0.03111 (8) | |
O1 | 0.49893 (14) | 0.57049 (11) | 0.27915 (3) | 0.0388 (2) | |
O2 | 0.50879 (12) | 0.37292 (10) | 0.34157 (3) | 0.03253 (18) | |
O3 | 0.81650 (12) | 0.34758 (10) | 0.42238 (3) | 0.03453 (19) | |
O4 | 0.56116 (14) | 0.41075 (12) | 0.45203 (3) | 0.0406 (2) | |
O5 | 0.25608 (11) | 0.64218 (10) | 0.18109 (3) | 0.03011 (17) | |
N1 | 0.68835 (12) | 0.44696 (11) | 0.42827 (3) | 0.02456 (17) | |
N2 | 0.41002 (11) | 0.32651 (12) | 0.21056 (3) | 0.02279 (16) | |
C1 | 0.63355 (12) | 0.66248 (12) | 0.35750 (3) | 0.02025 (17) | |
C2 | 0.69708 (12) | 0.62802 (12) | 0.40684 (3) | 0.01940 (16) | |
C3 | 0.77981 (12) | 0.76019 (13) | 0.43755 (3) | 0.02089 (17) | |
C4 | 0.80144 (13) | 0.93180 (13) | 0.41926 (4) | 0.02407 (18) | |
H4 | 0.857461 | 1.022784 | 0.440109 | 0.029* | |
C5 | 0.74011 (14) | 0.96853 (13) | 0.37014 (4) | 0.02617 (19) | |
H5 | 0.754706 | 1.085267 | 0.357150 | 0.031* | |
C6 | 0.65741 (13) | 0.83530 (13) | 0.33982 (4) | 0.02399 (18) | |
H6 | 0.616164 | 0.862693 | 0.306263 | 0.029* | |
C7 | 0.53938 (13) | 0.52246 (13) | 0.32319 (4) | 0.02389 (18) | |
C8 | 0.47845 (15) | 0.17222 (14) | 0.22785 (4) | 0.0276 (2) | |
H8 | 0.530731 | 0.164820 | 0.261364 | 0.033* | |
C9 | 0.47520 (16) | 0.02008 (14) | 0.19773 (4) | 0.0314 (2) | |
H9 | 0.520396 | −0.091226 | 0.210789 | 0.038* | |
C10 | 0.40556 (15) | 0.03461 (14) | 0.14900 (4) | 0.0292 (2) | |
H10 | 0.404556 | −0.067323 | 0.127964 | 0.035* | |
C11 | 0.33516 (13) | 0.19899 (13) | 0.12955 (4) | 0.02402 (19) | |
C12 | 0.26151 (15) | 0.22187 (16) | 0.07953 (4) | 0.0303 (2) | |
H12 | 0.260234 | 0.124767 | 0.056813 | 0.036* | |
C13 | 0.19225 (15) | 0.38479 (17) | 0.06420 (4) | 0.0317 (2) | |
H13 | 0.145274 | 0.400180 | 0.030447 | 0.038* | |
C14 | 0.18881 (14) | 0.53056 (16) | 0.09724 (4) | 0.0287 (2) | |
H14 | 0.138468 | 0.641773 | 0.085598 | 0.034* | |
C15 | 0.25798 (13) | 0.51294 (13) | 0.14634 (4) | 0.02325 (18) | |
C16 | 0.33572 (12) | 0.34640 (13) | 0.16246 (3) | 0.02087 (17) | |
H2 | 0.421 (2) | 0.417 (2) | 0.2315 (6) | 0.044 (4)* | |
H5O | 0.173 (3) | 0.722 (2) | 0.1717 (7) | 0.049 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.04386 (16) | 0.02719 (13) | 0.02051 (12) | −0.00200 (9) | −0.00565 (9) | −0.00222 (8) |
O1 | 0.0621 (6) | 0.0278 (4) | 0.0233 (4) | −0.0053 (4) | −0.0116 (3) | −0.0018 (3) |
O2 | 0.0403 (4) | 0.0219 (3) | 0.0328 (4) | −0.0084 (3) | −0.0092 (3) | 0.0002 (3) |
O3 | 0.0389 (4) | 0.0186 (3) | 0.0436 (5) | 0.0042 (3) | −0.0082 (3) | 0.0010 (3) |
O4 | 0.0546 (5) | 0.0327 (4) | 0.0368 (4) | −0.0104 (4) | 0.0154 (4) | 0.0047 (3) |
O5 | 0.0389 (4) | 0.0219 (3) | 0.0282 (4) | 0.0071 (3) | −0.0033 (3) | −0.0022 (3) |
N1 | 0.0342 (4) | 0.0172 (3) | 0.0211 (4) | −0.0033 (3) | −0.0036 (3) | 0.0004 (3) |
N2 | 0.0267 (4) | 0.0202 (4) | 0.0214 (4) | 0.0002 (3) | 0.0019 (3) | −0.0013 (3) |
C1 | 0.0217 (4) | 0.0178 (4) | 0.0206 (4) | 0.0009 (3) | −0.0011 (3) | −0.0016 (3) |
C2 | 0.0219 (4) | 0.0152 (4) | 0.0208 (4) | 0.0006 (3) | 0.0008 (3) | 0.0002 (3) |
C3 | 0.0228 (4) | 0.0187 (4) | 0.0206 (4) | 0.0012 (3) | −0.0007 (3) | −0.0023 (3) |
C4 | 0.0256 (4) | 0.0165 (4) | 0.0292 (5) | −0.0006 (3) | −0.0022 (3) | −0.0030 (3) |
C5 | 0.0300 (5) | 0.0161 (4) | 0.0315 (5) | 0.0002 (3) | −0.0013 (4) | 0.0023 (3) |
C6 | 0.0277 (4) | 0.0194 (4) | 0.0240 (4) | 0.0016 (3) | −0.0016 (3) | 0.0025 (3) |
C7 | 0.0263 (4) | 0.0205 (4) | 0.0236 (4) | 0.0007 (3) | −0.0040 (3) | −0.0032 (3) |
C8 | 0.0318 (5) | 0.0250 (5) | 0.0259 (4) | 0.0026 (4) | 0.0025 (4) | 0.0029 (4) |
C9 | 0.0361 (5) | 0.0219 (5) | 0.0368 (5) | 0.0044 (4) | 0.0066 (4) | 0.0014 (4) |
C10 | 0.0321 (5) | 0.0219 (4) | 0.0348 (5) | −0.0013 (4) | 0.0090 (4) | −0.0065 (4) |
C11 | 0.0228 (4) | 0.0249 (4) | 0.0249 (4) | −0.0035 (3) | 0.0053 (3) | −0.0040 (3) |
C12 | 0.0300 (5) | 0.0367 (6) | 0.0246 (5) | −0.0062 (4) | 0.0042 (4) | −0.0083 (4) |
C13 | 0.0289 (5) | 0.0450 (6) | 0.0207 (4) | −0.0029 (4) | 0.0002 (3) | −0.0003 (4) |
C14 | 0.0272 (4) | 0.0335 (5) | 0.0251 (5) | 0.0015 (4) | 0.0012 (4) | 0.0054 (4) |
C15 | 0.0232 (4) | 0.0229 (4) | 0.0237 (4) | −0.0004 (3) | 0.0024 (3) | 0.0006 (3) |
C16 | 0.0202 (4) | 0.0212 (4) | 0.0214 (4) | −0.0019 (3) | 0.0030 (3) | −0.0010 (3) |
Geometric parameters (Å, º) top
Cl1—C3 | 1.7268 (10) | C5—C6 | 1.3898 (14) |
O1—C7 | 1.2511 (12) | C5—H5 | 0.9500 |
O2—C7 | 1.2519 (13) | C6—H6 | 0.9500 |
O3—N1 | 1.2211 (12) | C8—C9 | 1.3969 (15) |
O4—N1 | 1.2154 (12) | C8—H8 | 0.9500 |
O5—C15 | 1.3483 (12) | C9—C10 | 1.3695 (16) |
O5—H5O | 0.872 (19) | C9—H9 | 0.9500 |
N1—C2 | 1.4751 (12) | C10—C11 | 1.4132 (15) |
N2—C8 | 1.3236 (13) | C10—H10 | 0.9500 |
N2—C16 | 1.3676 (12) | C11—C16 | 1.4154 (13) |
N2—H2 | 0.880 (16) | C11—C12 | 1.4161 (14) |
C1—C2 | 1.3930 (12) | C12—C13 | 1.3671 (17) |
C1—C6 | 1.3935 (13) | C12—H12 | 0.9500 |
C1—C7 | 1.5180 (13) | C13—C14 | 1.4103 (16) |
C2—C3 | 1.3902 (12) | C13—H13 | 0.9500 |
C3—C4 | 1.3887 (13) | C14—C15 | 1.3798 (14) |
C4—C5 | 1.3870 (14) | C14—H14 | 0.9500 |
C4—H4 | 0.9500 | C15—C16 | 1.4189 (13) |
| | | |
C15—O5—H5O | 109.9 (12) | N2—C8—C9 | 121.23 (10) |
O4—N1—O3 | 125.17 (9) | N2—C8—H8 | 119.4 |
O4—N1—C2 | 118.51 (9) | C9—C8—H8 | 119.4 |
O3—N1—C2 | 116.22 (9) | C10—C9—C8 | 118.66 (10) |
C8—N2—C16 | 122.14 (9) | C10—C9—H9 | 120.7 |
C8—N2—H2 | 115.9 (11) | C8—C9—H9 | 120.7 |
C16—N2—H2 | 121.9 (11) | C9—C10—C11 | 120.97 (9) |
C2—C1—C6 | 117.27 (8) | C9—C10—H10 | 119.5 |
C2—C1—C7 | 123.14 (8) | C11—C10—H10 | 119.5 |
C6—C1—C7 | 119.58 (8) | C10—C11—C16 | 117.63 (9) |
C3—C2—C1 | 121.72 (8) | C10—C11—C12 | 123.44 (9) |
C3—C2—N1 | 116.73 (8) | C16—C11—C12 | 118.92 (9) |
C1—C2—N1 | 121.48 (8) | C13—C12—C11 | 119.49 (10) |
C4—C3—C2 | 120.08 (9) | C13—C12—H12 | 120.3 |
C4—C3—Cl1 | 119.26 (7) | C11—C12—H12 | 120.3 |
C2—C3—Cl1 | 120.64 (7) | C12—C13—C14 | 121.63 (10) |
C5—C4—C3 | 119.08 (9) | C12—C13—H13 | 119.2 |
C5—C4—H4 | 120.5 | C14—C13—H13 | 119.2 |
C3—C4—H4 | 120.5 | C15—C14—C13 | 120.53 (10) |
C4—C5—C6 | 120.29 (9) | C15—C14—H14 | 119.7 |
C4—C5—H5 | 119.9 | C13—C14—H14 | 119.7 |
C6—C5—H5 | 119.9 | O5—C15—C14 | 125.04 (9) |
C5—C6—C1 | 121.56 (9) | O5—C15—C16 | 116.43 (8) |
C5—C6—H6 | 119.2 | C14—C15—C16 | 118.52 (9) |
C1—C6—H6 | 119.2 | N2—C16—C11 | 119.30 (9) |
O1—C7—O2 | 126.78 (9) | N2—C16—C15 | 119.84 (8) |
O1—C7—C1 | 115.77 (9) | C11—C16—C15 | 120.85 (9) |
O2—C7—C1 | 117.44 (8) | | |
| | | |
C6—C1—C2—C3 | 0.47 (14) | C16—N2—C8—C9 | −1.11 (16) |
C7—C1—C2—C3 | −178.81 (9) | N2—C8—C9—C10 | 2.40 (16) |
C6—C1—C2—N1 | −176.32 (8) | C8—C9—C10—C11 | −1.12 (16) |
C7—C1—C2—N1 | 4.41 (14) | C9—C10—C11—C16 | −1.33 (15) |
O4—N1—C2—C3 | 85.64 (11) | C9—C10—C11—C12 | −179.99 (10) |
O3—N1—C2—C3 | −91.03 (11) | C10—C11—C12—C13 | 178.41 (10) |
O4—N1—C2—C1 | −97.42 (11) | C16—C11—C12—C13 | −0.23 (14) |
O3—N1—C2—C1 | 85.91 (11) | C11—C12—C13—C14 | −1.28 (16) |
C1—C2—C3—C4 | −0.17 (14) | C12—C13—C14—C15 | 0.76 (16) |
N1—C2—C3—C4 | 176.76 (8) | C13—C14—C15—O5 | −177.90 (10) |
C1—C2—C3—Cl1 | −178.87 (7) | C13—C14—C15—C16 | 1.27 (15) |
N1—C2—C3—Cl1 | −1.94 (12) | C8—N2—C16—C11 | −1.46 (14) |
C2—C3—C4—C5 | −0.23 (14) | C8—N2—C16—C15 | 177.62 (9) |
Cl1—C3—C4—C5 | 178.49 (8) | C10—C11—C16—N2 | 2.62 (13) |
C3—C4—C5—C6 | 0.32 (15) | C12—C11—C16—N2 | −178.66 (9) |
C4—C5—C6—C1 | −0.01 (15) | C10—C11—C16—C15 | −176.45 (9) |
C2—C1—C6—C5 | −0.38 (14) | C12—C11—C16—C15 | 2.27 (14) |
C7—C1—C6—C5 | 178.92 (9) | O5—C15—C16—N2 | −2.60 (13) |
C2—C1—C7—O1 | −176.23 (9) | C14—C15—C16—N2 | 178.16 (9) |
C6—C1—C7—O1 | 4.51 (14) | O5—C15—C16—C11 | 176.47 (8) |
C2—C1—C7—O2 | 4.37 (14) | C14—C15—C16—C11 | −2.77 (14) |
C6—C1—C7—O2 | −174.89 (9) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1 | 0.880 (16) | 1.776 (16) | 2.6355 (12) | 164.7 (14) |
O5—H5O···O2i | 0.872 (19) | 1.756 (19) | 2.6247 (12) | 173.2 (19) |
C4—H4···O3ii | 0.95 | 2.49 | 3.1082 (12) | 123 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) x, y+1, z. |