Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705386X/hg2333sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680705386X/hg2333Isup2.hkl |
CCDC reference: 672796
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.040
- wR factor = 0.088
- Data-to-parameter ratio = 20.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT335_ALERT_2_C Large Benzene C-C Range ....... C1 -C6 0.20 Ang. PLAT335_ALERT_2_C Large Benzene C-C Range ....... C7 -C12 0.20 Ang. PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C6 ... 1.54 Ang. PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C7 - C12 ... 1.55 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O4 .. C3 .. 2.93 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact C9 .. C11 .. 3.13 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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
Single crystals were obtained by slow evaporation from a methanol solution of chloranilic acid (63 mg) with 4,4'-bipiperidyl dihydrochloride (36 mg).
N– and O-bound H atoms were located in a difference Fourier map and refined isotropically (refined distances are given in Table 1). Other H atoms were positioned geometrically (C—H = 0.98 or 0.99 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C).
Data collection: PROCESS-AUTO (Rigaku/MSC, 2004); cell refinement: PROCESS-AUTO (Rigaku/MSC, 2004); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004) and PLATON (Spek, 2003).
C10H22N22+·2C6HCl2O4− | F(000) = 1208.00 |
Mr = 586.25 | Dx = 1.624 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: -P 2yn | Cell parameters from 27745 reflections |
a = 17.4716 (10) Å | θ = 3.2–30.1° |
b = 7.7132 (4) Å | µ = 0.55 mm−1 |
c = 19.1252 (11) Å | T = 100 K |
β = 111.5434 (19)° | Needle, purple |
V = 2397.3 (2) Å3 | 0.25 × 0.17 × 0.12 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 5848 reflections with I > 2σ(I) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.035 |
ω scans | θmax = 30.0° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −24→23 |
Tmin = 0.850, Tmax = 0.937 | k = −10→10 |
26002 measured reflections | l = −26→26 |
6982 independent reflections |
Refinement on F2 | 0 restraints |
R[F2 > 2σ(F2)] = 0.040 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.088 | w = 1/[σ2(Fo2) + (0.0399P)2 + 1.34P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max < 0.001 |
6982 reflections | Δρmax = 0.43 e Å−3 |
349 parameters | Δρmin = −0.29 e Å−3 |
C10H22N22+·2C6HCl2O4− | V = 2397.3 (2) Å3 |
Mr = 586.25 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 17.4716 (10) Å | µ = 0.55 mm−1 |
b = 7.7132 (4) Å | T = 100 K |
c = 19.1252 (11) Å | 0.25 × 0.17 × 0.12 mm |
β = 111.5434 (19)° |
Rigaku R-AXIS RAPID diffractometer | 6982 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 5848 reflections with I > 2σ(I) |
Tmin = 0.850, Tmax = 0.937 | Rint = 0.035 |
26002 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.088 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 0.43 e Å−3 |
6982 reflections | Δρmin = −0.29 e Å−3 |
349 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. 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 > σ(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 | ||
Cl1 | 0.40240 (2) | 0.05182 (5) | 0.45568 (2) | 0.01654 (8) | |
Cl2 | 0.10315 (2) | 0.00510 (6) | 0.14248 (2) | 0.01867 (9) | |
Cl3 | 0.79278 (2) | 0.95757 (6) | 0.30125 (2) | 0.02012 (9) | |
Cl4 | 1.08946 (2) | 0.66212 (5) | 0.58222 (2) | 0.01466 (8) | |
O1 | 0.40238 (7) | −0.07957 (16) | 0.31131 (7) | 0.0174 (2) | |
O2 | 0.22655 (7) | 0.13356 (15) | 0.42519 (6) | 0.0139 (2) | |
O3 | 0.10072 (7) | 0.08933 (15) | 0.29685 (6) | 0.0143 (2) | |
O4 | 0.28393 (7) | −0.05474 (16) | 0.17399 (6) | 0.0165 (2) | |
O5 | 0.78585 (7) | 0.73421 (16) | 0.42744 (6) | 0.0163 (2) | |
O6 | 0.97184 (7) | 1.01381 (15) | 0.33987 (6) | 0.0141 (2) | |
O7 | 1.09316 (7) | 0.88325 (15) | 0.45278 (6) | 0.0151 (2) | |
O8 | 0.90753 (7) | 0.66571 (16) | 0.55947 (6) | 0.0163 (2) | |
N1 | 0.48752 (8) | −0.08134 (18) | 0.21307 (7) | 0.0127 (2) | |
N2 | 0.72848 (8) | 0.49927 (18) | 0.51771 (8) | 0.0137 (3) | |
C1 | 0.33488 (9) | −0.0260 (2) | 0.30686 (8) | 0.0120 (3) | |
C2 | 0.31958 (9) | 0.0360 (2) | 0.37204 (8) | 0.0120 (3) | |
C3 | 0.24259 (9) | 0.07760 (19) | 0.36626 (8) | 0.0109 (3) | |
C4 | 0.16933 (9) | 0.05946 (19) | 0.29323 (8) | 0.0112 (3) | |
C5 | 0.18512 (9) | 0.0135 (2) | 0.22824 (8) | 0.0132 (3) | |
C6 | 0.26422 (9) | −0.0220 (2) | 0.22931 (8) | 0.0119 (3) | |
C7 | 0.85514 (9) | 0.7831 (2) | 0.43545 (8) | 0.0119 (3) | |
C8 | 0.87308 (9) | 0.8865 (2) | 0.37990 (8) | 0.0127 (3) | |
C9 | 0.95195 (9) | 0.9208 (2) | 0.38904 (8) | 0.0115 (3) | |
C10 | 1.02423 (9) | 0.84710 (19) | 0.45370 (8) | 0.0111 (3) | |
C11 | 1.00710 (9) | 0.7486 (2) | 0.50857 (8) | 0.0115 (3) | |
C12 | 0.92737 (9) | 0.72772 (19) | 0.50780 (8) | 0.0116 (3) | |
C13 | 0.48474 (10) | 0.1099 (2) | 0.19929 (9) | 0.0160 (3) | |
H5 | 0.4285 | 0.1439 | 0.1682 | 0.019* | |
H6 | 0.5205 | 0.1386 | 0.1717 | 0.019* | |
C14 | 0.51248 (10) | 0.2110 (2) | 0.27274 (8) | 0.0138 (3) | |
H7 | 0.4736 | 0.1906 | 0.2980 | 0.017* | |
H8 | 0.5119 | 0.3353 | 0.2618 | 0.017* | |
C15 | 0.59924 (9) | 0.1584 (2) | 0.32548 (8) | 0.0113 (3) | |
H9 | 0.6384 | 0.1855 | 0.3005 | 0.014* | |
C16 | 0.59974 (9) | −0.0392 (2) | 0.33798 (8) | 0.0123 (3) | |
H10 | 0.6557 | −0.0760 | 0.3689 | 0.015* | |
H11 | 0.5638 | −0.0665 | 0.3656 | 0.015* | |
C17 | 0.57093 (10) | −0.1400 (2) | 0.26450 (9) | 0.0146 (3) | |
H12 | 0.6104 | −0.1239 | 0.2396 | 0.018* | |
H13 | 0.5690 | −0.2639 | 0.2751 | 0.018* | |
C18 | 0.73772 (10) | 0.3062 (2) | 0.52769 (9) | 0.0148 (3) | |
H16 | 0.7031 | 0.2651 | 0.5547 | 0.018* | |
H17 | 0.7950 | 0.2787 | 0.5583 | 0.018* | |
C19 | 0.71351 (9) | 0.2121 (2) | 0.45278 (9) | 0.0140 (3) | |
H18 | 0.7172 | 0.0867 | 0.4616 | 0.017* | |
H19 | 0.7522 | 0.2429 | 0.4284 | 0.017* | |
C20 | 0.62581 (9) | 0.25870 (19) | 0.40037 (8) | 0.0107 (3) | |
H20 | 0.5879 | 0.2268 | 0.4260 | 0.013* | |
C21 | 0.62210 (9) | 0.4567 (2) | 0.38979 (8) | 0.0129 (3) | |
H21 | 0.6600 | 0.4914 | 0.3652 | 0.015* | |
H22 | 0.5664 | 0.4904 | 0.3571 | 0.015* | |
C22 | 0.64503 (10) | 0.5509 (2) | 0.46465 (9) | 0.0147 (3) | |
H23 | 0.6440 | 0.6763 | 0.4561 | 0.018* | |
H24 | 0.6043 | 0.5243 | 0.4872 | 0.018* | |
H1 | 0.1747 (15) | 0.161 (3) | 0.4119 (13) | 0.032 (6)* | |
H2 | 1.0218 (16) | 1.013 (3) | 0.3529 (14) | 0.034 (7)* | |
H3 | 0.4514 (13) | −0.111 (3) | 0.2344 (12) | 0.018 (5)* | |
H4 | 0.4730 (13) | −0.133 (3) | 0.1706 (12) | 0.016 (5)* | |
H14 | 0.7663 (13) | 0.542 (3) | 0.5008 (12) | 0.019 (5)* | |
H15 | 0.7399 (13) | 0.543 (3) | 0.5629 (12) | 0.016 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.01155 (15) | 0.02349 (19) | 0.01206 (16) | 0.00183 (14) | 0.00137 (13) | −0.00107 (14) |
Cl2 | 0.01405 (16) | 0.0287 (2) | 0.01102 (16) | −0.00135 (15) | 0.00191 (13) | −0.00284 (14) |
Cl3 | 0.01221 (16) | 0.0314 (2) | 0.01461 (17) | 0.00159 (15) | 0.00244 (13) | 0.00730 (15) |
Cl4 | 0.01224 (15) | 0.01595 (17) | 0.01420 (16) | 0.00208 (13) | 0.00299 (13) | 0.00227 (13) |
O1 | 0.0131 (5) | 0.0216 (6) | 0.0191 (6) | 0.0026 (5) | 0.0079 (4) | −0.0011 (5) |
O2 | 0.0126 (5) | 0.0195 (6) | 0.0107 (5) | 0.0015 (4) | 0.0055 (4) | −0.0016 (4) |
O3 | 0.0116 (5) | 0.0166 (5) | 0.0158 (5) | 0.0000 (4) | 0.0065 (4) | −0.0001 (4) |
O4 | 0.0188 (5) | 0.0202 (6) | 0.0128 (5) | 0.0025 (5) | 0.0086 (4) | −0.0007 (4) |
O5 | 0.0109 (5) | 0.0209 (6) | 0.0173 (5) | −0.0021 (4) | 0.0055 (4) | 0.0020 (5) |
O6 | 0.0130 (5) | 0.0166 (5) | 0.0148 (5) | −0.0004 (4) | 0.0075 (4) | 0.0030 (4) |
O7 | 0.0112 (5) | 0.0180 (6) | 0.0176 (5) | −0.0010 (4) | 0.0069 (4) | 0.0003 (4) |
O8 | 0.0148 (5) | 0.0212 (6) | 0.0145 (5) | −0.0008 (5) | 0.0074 (4) | 0.0045 (4) |
N1 | 0.0135 (6) | 0.0140 (6) | 0.0102 (6) | −0.0026 (5) | 0.0038 (5) | −0.0022 (5) |
N2 | 0.0137 (6) | 0.0147 (6) | 0.0124 (6) | −0.0038 (5) | 0.0043 (5) | −0.0030 (5) |
C1 | 0.0129 (6) | 0.0113 (7) | 0.0128 (7) | −0.0007 (5) | 0.0058 (5) | 0.0006 (5) |
C2 | 0.0109 (6) | 0.0147 (7) | 0.0094 (6) | −0.0002 (5) | 0.0025 (5) | −0.0002 (5) |
C3 | 0.0130 (6) | 0.0100 (6) | 0.0109 (6) | 0.0001 (5) | 0.0057 (5) | 0.0008 (5) |
C4 | 0.0112 (6) | 0.0105 (6) | 0.0123 (6) | −0.0012 (5) | 0.0048 (5) | 0.0005 (5) |
C5 | 0.0116 (6) | 0.0172 (7) | 0.0096 (6) | −0.0007 (6) | 0.0024 (5) | −0.0013 (5) |
C6 | 0.0133 (6) | 0.0111 (6) | 0.0120 (6) | −0.0005 (5) | 0.0054 (5) | −0.0008 (5) |
C7 | 0.0126 (6) | 0.0129 (7) | 0.0113 (6) | 0.0008 (5) | 0.0057 (5) | −0.0003 (5) |
C8 | 0.0114 (6) | 0.0161 (7) | 0.0095 (6) | 0.0009 (6) | 0.0027 (5) | 0.0011 (5) |
C9 | 0.0141 (6) | 0.0109 (6) | 0.0113 (6) | 0.0000 (5) | 0.0069 (5) | −0.0001 (5) |
C10 | 0.0122 (6) | 0.0105 (6) | 0.0111 (6) | −0.0001 (5) | 0.0047 (5) | −0.0024 (5) |
C11 | 0.0107 (6) | 0.0119 (7) | 0.0106 (6) | 0.0012 (5) | 0.0023 (5) | 0.0001 (5) |
C12 | 0.0125 (6) | 0.0101 (6) | 0.0124 (6) | −0.0006 (5) | 0.0049 (5) | −0.0010 (5) |
C13 | 0.0194 (7) | 0.0137 (7) | 0.0109 (7) | −0.0008 (6) | 0.0007 (6) | 0.0017 (6) |
C14 | 0.0160 (7) | 0.0107 (6) | 0.0109 (6) | 0.0008 (6) | 0.0004 (5) | 0.0000 (5) |
C15 | 0.0118 (6) | 0.0110 (6) | 0.0105 (6) | −0.0003 (5) | 0.0035 (5) | 0.0003 (5) |
C16 | 0.0129 (6) | 0.0108 (7) | 0.0115 (6) | 0.0009 (5) | 0.0023 (5) | −0.0007 (5) |
C17 | 0.0158 (7) | 0.0133 (7) | 0.0130 (7) | 0.0020 (6) | 0.0033 (6) | −0.0008 (5) |
C18 | 0.0141 (7) | 0.0129 (7) | 0.0138 (7) | −0.0003 (6) | 0.0011 (6) | −0.0001 (6) |
C19 | 0.0121 (6) | 0.0143 (7) | 0.0126 (7) | 0.0015 (6) | 0.0011 (5) | −0.0028 (6) |
C20 | 0.0109 (6) | 0.0107 (6) | 0.0097 (6) | −0.0004 (5) | 0.0030 (5) | 0.0003 (5) |
C21 | 0.0141 (7) | 0.0110 (6) | 0.0121 (7) | −0.0007 (5) | 0.0031 (5) | −0.0001 (5) |
C22 | 0.0153 (7) | 0.0133 (7) | 0.0144 (7) | 0.0010 (6) | 0.0039 (6) | −0.0007 (6) |
Cl1—C2 | 1.7227 (15) | C9—C10 | 1.517 (2) |
Cl2—C5 | 1.7379 (15) | C10—C11 | 1.414 (2) |
Cl3—C8 | 1.7267 (15) | C11—C12 | 1.397 (2) |
Cl4—C11 | 1.7350 (15) | C13—C14 | 1.522 (2) |
O1—C1 | 1.2226 (18) | C13—H5 | 0.9800 |
O2—C3 | 1.3293 (18) | C13—H6 | 0.9800 |
O2—H1 | 0.87 (2) | C14—C15 | 1.535 (2) |
O3—C4 | 1.2474 (18) | C14—H7 | 0.9800 |
O4—C6 | 1.2527 (18) | C14—H8 | 0.9800 |
O5—C7 | 1.2228 (18) | C15—C20 | 1.542 (2) |
O6—C9 | 1.3264 (18) | C15—C16 | 1.543 (2) |
O6—H2 | 0.82 (3) | C15—H9 | 0.9900 |
O7—C10 | 1.2425 (18) | C16—C17 | 1.521 (2) |
O8—C12 | 1.2557 (18) | C16—H10 | 0.9800 |
N1—C13 | 1.496 (2) | C16—H11 | 0.9800 |
N1—C17 | 1.498 (2) | C17—H12 | 0.9800 |
N1—H3 | 0.90 (2) | C17—H13 | 0.9800 |
N1—H4 | 0.86 (2) | C18—C19 | 1.521 (2) |
N2—C22 | 1.493 (2) | C18—H16 | 0.9800 |
N2—C18 | 1.502 (2) | C18—H17 | 0.9800 |
N2—H14 | 0.90 (2) | C19—C20 | 1.534 (2) |
N2—H15 | 0.88 (2) | C19—H18 | 0.9800 |
C1—C2 | 1.449 (2) | C19—H19 | 0.9800 |
C1—C6 | 1.543 (2) | C20—C21 | 1.539 (2) |
C2—C3 | 1.347 (2) | C20—H20 | 0.9900 |
C3—C4 | 1.515 (2) | C21—C22 | 1.522 (2) |
C4—C5 | 1.414 (2) | C21—H21 | 0.9800 |
C5—C6 | 1.402 (2) | C21—H22 | 0.9800 |
C7—C8 | 1.452 (2) | C22—H23 | 0.9800 |
C7—C12 | 1.551 (2) | C22—H24 | 0.9800 |
C8—C9 | 1.350 (2) | ||
C3—O2—H1 | 110.6 (16) | H5—C13—H6 | 108.0 |
C9—O6—H2 | 107.9 (18) | C13—C14—C15 | 111.96 (13) |
C13—N1—C17 | 111.98 (12) | C13—C14—H7 | 109.2 |
C13—N1—H3 | 110.4 (14) | C15—C14—H7 | 109.2 |
C17—N1—H3 | 107.6 (14) | C13—C14—H8 | 109.2 |
C13—N1—H4 | 108.4 (14) | C15—C14—H8 | 109.2 |
C17—N1—H4 | 111.0 (14) | H7—C14—H8 | 107.9 |
H3—N1—H4 | 107.4 (19) | C14—C15—C20 | 111.45 (12) |
C22—N2—C18 | 112.55 (12) | C14—C15—C16 | 108.11 (12) |
C22—N2—H14 | 108.7 (14) | C20—C15—C16 | 111.67 (12) |
C18—N2—H14 | 110.6 (14) | C14—C15—H9 | 108.5 |
C22—N2—H15 | 112.2 (14) | C20—C15—H9 | 108.5 |
C18—N2—H15 | 106.2 (14) | C16—C15—H9 | 108.5 |
H14—N2—H15 | 106.3 (19) | C17—C16—C15 | 112.39 (12) |
O1—C1—C2 | 121.98 (14) | C17—C16—H10 | 109.1 |
O1—C1—C6 | 118.99 (13) | C15—C16—H10 | 109.1 |
C2—C1—C6 | 119.02 (13) | C17—C16—H11 | 109.1 |
C3—C2—C1 | 120.14 (14) | C15—C16—H11 | 109.1 |
C3—C2—Cl1 | 122.14 (12) | H10—C16—H11 | 107.9 |
C1—C2—Cl1 | 117.71 (11) | N1—C17—C16 | 111.37 (13) |
O2—C3—C2 | 121.52 (14) | N1—C17—H12 | 109.4 |
O2—C3—C4 | 116.22 (13) | C16—C17—H12 | 109.4 |
C2—C3—C4 | 122.25 (13) | N1—C17—H13 | 109.4 |
O3—C4—C5 | 126.65 (14) | C16—C17—H13 | 109.4 |
O3—C4—C3 | 115.82 (13) | H12—C17—H13 | 108.0 |
C5—C4—C3 | 117.52 (13) | N2—C18—C19 | 111.94 (13) |
C6—C5—C4 | 123.08 (14) | N2—C18—H16 | 109.2 |
C6—C5—Cl2 | 118.23 (11) | C19—C18—H16 | 109.2 |
C4—C5—Cl2 | 118.68 (11) | N2—C18—H17 | 109.2 |
O4—C6—C5 | 127.04 (14) | C19—C18—H17 | 109.2 |
O4—C6—C1 | 115.89 (13) | H16—C18—H17 | 107.9 |
C5—C6—C1 | 117.05 (13) | C18—C19—C20 | 111.67 (13) |
O5—C7—C8 | 123.20 (14) | C18—C19—H18 | 109.3 |
O5—C7—C12 | 118.06 (13) | C20—C19—H18 | 109.3 |
C8—C7—C12 | 118.72 (13) | C18—C19—H19 | 109.3 |
C9—C8—C7 | 119.82 (14) | C20—C19—H19 | 109.3 |
C9—C8—Cl3 | 120.98 (12) | H18—C19—H19 | 107.9 |
C7—C8—Cl3 | 119.16 (11) | C19—C20—C21 | 107.58 (12) |
O6—C9—C8 | 122.33 (14) | C19—C20—C15 | 112.17 (12) |
O6—C9—C10 | 115.10 (13) | C21—C20—C15 | 113.08 (12) |
C8—C9—C10 | 122.47 (13) | C19—C20—H20 | 107.9 |
O7—C10—C11 | 126.98 (14) | C21—C20—H20 | 107.9 |
O7—C10—C9 | 115.18 (13) | C15—C20—H20 | 107.9 |
C11—C10—C9 | 117.83 (13) | C22—C21—C20 | 111.48 (12) |
C12—C11—C10 | 122.41 (13) | C22—C21—H21 | 109.3 |
C12—C11—Cl4 | 119.40 (12) | C20—C21—H21 | 109.3 |
C10—C11—Cl4 | 118.08 (11) | C22—C21—H22 | 109.3 |
O8—C12—C11 | 126.71 (14) | C20—C21—H22 | 109.3 |
O8—C12—C7 | 115.95 (13) | H21—C21—H22 | 108.0 |
C11—C12—C7 | 117.33 (13) | N2—C22—C21 | 111.48 (13) |
N1—C13—C14 | 111.34 (12) | N2—C22—H23 | 109.3 |
N1—C13—H5 | 109.4 | C21—C22—H23 | 109.3 |
C14—C13—H5 | 109.4 | N2—C22—H24 | 109.3 |
N1—C13—H6 | 109.4 | C21—C22—H24 | 109.3 |
C14—C13—H6 | 109.4 | H23—C22—H24 | 108.0 |
O1—C1—C2—C3 | −173.35 (15) | O6—C9—C10—C11 | 179.20 (13) |
C6—C1—C2—C3 | 7.5 (2) | C8—C9—C10—C11 | −4.3 (2) |
O1—C1—C2—Cl1 | 6.1 (2) | O7—C10—C11—C12 | 174.38 (15) |
C6—C1—C2—Cl1 | −173.04 (11) | C9—C10—C11—C12 | −4.5 (2) |
C1—C2—C3—O2 | 179.49 (14) | O7—C10—C11—Cl4 | −1.7 (2) |
Cl1—C2—C3—O2 | 0.1 (2) | C9—C10—C11—Cl4 | 179.40 (11) |
C1—C2—C3—C4 | 1.0 (2) | C10—C11—C12—O8 | −168.50 (15) |
Cl1—C2—C3—C4 | −178.42 (11) | Cl4—C11—C12—O8 | 7.5 (2) |
O2—C3—C4—O3 | −4.0 (2) | C10—C11—C12—C7 | 12.7 (2) |
C2—C3—C4—O3 | 174.57 (15) | Cl4—C11—C12—C7 | −171.22 (11) |
O2—C3—C4—C5 | 175.08 (14) | O5—C7—C12—O8 | −13.5 (2) |
C2—C3—C4—C5 | −6.3 (2) | C8—C7—C12—O8 | 167.88 (14) |
O3—C4—C5—C6 | −178.45 (15) | O5—C7—C12—C11 | 165.34 (15) |
C3—C4—C5—C6 | 2.6 (2) | C8—C7—C12—C11 | −13.2 (2) |
O3—C4—C5—Cl2 | 3.0 (2) | C17—N1—C13—C14 | −55.38 (17) |
C3—C4—C5—Cl2 | −175.97 (11) | N1—C13—C14—C15 | 56.83 (17) |
C4—C5—C6—O4 | −176.08 (15) | C13—C14—C15—C20 | −178.69 (13) |
Cl2—C5—C6—O4 | 2.5 (2) | C13—C14—C15—C16 | −55.60 (16) |
C4—C5—C6—C1 | 5.6 (2) | C14—C15—C16—C17 | 55.13 (16) |
Cl2—C5—C6—C1 | −175.86 (11) | C20—C15—C16—C17 | 178.08 (12) |
O1—C1—C6—O4 | −8.5 (2) | C13—N1—C17—C16 | 54.67 (17) |
C2—C1—C6—O4 | 170.67 (14) | C15—C16—C17—N1 | −55.48 (17) |
O1—C1—C6—C5 | 170.03 (15) | C22—N2—C18—C19 | 52.57 (17) |
C2—C1—C6—C5 | −10.8 (2) | N2—C18—C19—C20 | −55.52 (17) |
O5—C7—C8—C9 | −173.27 (15) | C18—C19—C20—C21 | 57.38 (16) |
C12—C7—C8—C9 | 5.2 (2) | C18—C19—C20—C15 | −177.66 (13) |
O5—C7—C8—Cl3 | 4.5 (2) | C14—C15—C20—C19 | −178.13 (12) |
C12—C7—C8—Cl3 | −176.98 (11) | C16—C15—C20—C19 | 60.84 (16) |
C7—C8—C9—O6 | 179.66 (14) | C14—C15—C20—C21 | −56.25 (16) |
Cl3—C8—C9—O6 | 1.9 (2) | C16—C15—C20—C21 | −177.29 (12) |
C7—C8—C9—C10 | 3.4 (2) | C19—C20—C21—C22 | −58.14 (16) |
Cl3—C8—C9—C10 | −174.37 (11) | C15—C20—C21—C22 | 177.44 (12) |
O6—C9—C10—O7 | 0.2 (2) | C18—N2—C22—C21 | −53.18 (17) |
C8—C9—C10—O7 | 176.71 (15) | C20—C21—C22—N2 | 56.98 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H1···O3 | 0.87 (3) | 2.18 (2) | 2.6479 (16) | 113.6 (19) |
O2—H1···O8i | 0.87 (3) | 2.17 (3) | 2.9113 (18) | 142 (2) |
O6—H2···O3ii | 0.82 (3) | 2.12 (3) | 2.7290 (18) | 132 (2) |
O6—H2···O7 | 0.82 (3) | 2.11 (2) | 2.6093 (16) | 119 (2) |
N1—H3···O1 | 0.90 (2) | 1.97 (2) | 2.7921 (19) | 152 (2) |
N1—H3···O3iii | 0.90 (2) | 2.48 (2) | 2.9412 (19) | 112.7 (17) |
N1—H4···O8iv | 0.86 (2) | 2.03 (2) | 2.8269 (17) | 156 (2) |
N2—H14···O5 | 0.90 (2) | 2.15 (2) | 2.9223 (19) | 143 (2) |
N2—H14···O8 | 0.90 (2) | 2.50 (2) | 3.200 (2) | 135.7 (18) |
N2—H15···O2i | 0.88 (2) | 2.55 (2) | 3.0332 (18) | 115.1 (17) |
N2—H15···O4v | 0.88 (2) | 1.98 (2) | 2.8158 (18) | 159 (2) |
C14—H7···O1 | 0.98 | 2.49 | 3.211 (2) | 130 |
C14—H8···O6vi | 0.98 | 2.48 | 3.2561 (19) | 136 |
C16—H10···O5vii | 0.98 | 2.59 | 3.531 (2) | 161 |
C18—H17···O7viii | 0.98 | 2.39 | 3.193 (2) | 138 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y+1, z; (iii) −x+1/2, y−1/2, −z+1/2; (iv) x−1/2, −y+1/2, z−1/2; (v) x+1/2, −y+1/2, z+1/2; (vi) −x+3/2, y−1/2, −z+1/2; (vii) x, y−1, z; (viii) −x+2, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C10H22N22+·2C6HCl2O4− |
Mr | 586.25 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 100 |
a, b, c (Å) | 17.4716 (10), 7.7132 (4), 19.1252 (11) |
β (°) | 111.5434 (19) |
V (Å3) | 2397.3 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.55 |
Crystal size (mm) | 0.25 × 0.17 × 0.12 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.850, 0.937 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 26002, 6982, 5848 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.704 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.088, 1.11 |
No. of reflections | 6982 |
No. of parameters | 349 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.43, −0.29 |
Computer programs: PROCESS-AUTO (Rigaku/MSC, 2004), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), CrystalStructure (Rigaku/MSC, 2004) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H1···O3 | 0.87 (3) | 2.18 (2) | 2.6479 (16) | 113.6 (19) |
O2—H1···O8i | 0.87 (3) | 2.17 (3) | 2.9113 (18) | 142 (2) |
O6—H2···O3ii | 0.82 (3) | 2.12 (3) | 2.7290 (18) | 132 (2) |
O6—H2···O7 | 0.82 (3) | 2.11 (2) | 2.6093 (16) | 119 (2) |
N1—H3···O1 | 0.90 (2) | 1.97 (2) | 2.7921 (19) | 152 (2) |
N1—H3···O3iii | 0.90 (2) | 2.48 (2) | 2.9412 (19) | 112.7 (17) |
N1—H4···O8iv | 0.86 (2) | 2.03 (2) | 2.8269 (17) | 156 (2) |
N2—H14···O5 | 0.90 (2) | 2.15 (2) | 2.9223 (19) | 143 (2) |
N2—H14···O8 | 0.90 (2) | 2.50 (2) | 3.200 (2) | 135.7 (18) |
N2—H15···O2i | 0.88 (2) | 2.55 (2) | 3.0332 (18) | 115.1 (17) |
N2—H15···O4v | 0.88 (2) | 1.98 (2) | 2.8158 (18) | 159 (2) |
C14—H7···O1 | 0.98 | 2.49 | 3.211 (2) | 130 |
C14—H8···O6vi | 0.98 | 2.48 | 3.2561 (19) | 136 |
C16—H10···O5vii | 0.98 | 2.59 | 3.531 (2) | 161 |
C18—H17···O7viii | 0.98 | 2.39 | 3.193 (2) | 138 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y+1, z; (iii) −x+1/2, y−1/2, −z+1/2; (iv) x−1/2, −y+1/2, z−1/2; (v) x+1/2, −y+1/2, z+1/2; (vi) −x+3/2, y−1/2, −z+1/2; (vii) x, y−1, z; (viii) −x+2, −y+1, −z+1. |
The title compound, (I), was prepared in order to extend our study on D—H···A hydrogen bonding (D = N, O, or C; A = N, O or Cl) in amine – chloranilic acid (1/1) and (2/1) systems (Ishida, 2004; Refat et al., 2006). To our knowledge, this is the first crystallographic report of the amine – chloranilic acid (1/2) system; no structural data of compounds of the (1/2) system are recorded in the Cambridge Structural Database, version 5.28 (2007 Release; Allen, 2002).
The asymmetric unit in the title compound contains one 4,4'-bipiperidinium dication and two hydrogen chloranilate anions, which are connected by N—H···O, bifurcated N—H···O and C—H···O hydrogen bonds (Table 1) to form a 1:2 unit (Fig. 1). The two units related by an inversion center are held together through O—H···O hydrogen bonds, forming a macro molecular ring (Fig. 2). The rings are further connected by O—H···O, N—H···O and C—H···O hydrogen bonds, leading to a three-dimensional hydrogen-bonding network.