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Pyridinium-4-carboxylic acid perchlorate (C6H6NO2·ClO4) was synthesized and separated as crystals. Differential scanning calorimetry measurement shows that this compound undergoes a reversible phase transition at about 122 K with a heat hysteresis of 1.8 K. A dielectric anomaly observed at 127 K further confirms the phase transition. The low-temperature (LT; T = 103 K) structure has space group P21/c and cell parameters a = 17.356 (6), b = 13.241 (3), c = 16.161 (7) Å, β = 138.055 (17)°. The high-temperature (HT; T = 298 K) structure has space group P21/c and cell parameters a = 5.5046 (11), b = 13.574 (3), c = 11.834 (2) Å, β = 99.35 (3)°, but can be re-described using new axes a′ = a, b′ = b, c′ = −2a + c, V′ = V to give the cell a′ = 5.5046 (11), b′ = 13.574 (3), c′ = 17.424 (3) Å, β′ = 137.92 (3)° and space group P21/c. The associated coordinate transformation is x′ = x + 2z, y′ = y, z′ = z and the associated reflection index transformation is h′ = h, k′ = k, l′ = l − 2h. The relationship between the two cells is 3a, b, c (HT) approximates a, b, c (LT). The crystal comprises one-dimensional hydrogen-bonded chains of the pyridinium-4-carboxylic acid cations and perchlorate anions. A precise analysis of the main packing and structural differences as well as the changes in the intermolecular interactions between the HT phase and the LT phase reveals that the disorder–order transition of the perchlorate anions may be the driving force of the transition, and the hydrogen-bonding effect may contribute to the transition as a secondary parameter.
Supporting information
CCDC references: 798619; 798620
For both compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).
Crystal data top
C6H6ClNO6 | Z = 4 |
Mr = 223.57 | F(000) = 456 |
Monoclinic, p21/c | Dx = 1.702 Mg m−3 |
a = 5.5046 (11) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.574 (3) Å | µ = 0.44 mm−1 |
c = 17.423 (5) Å | T = 298 K |
β = 137.919 (17)° | 0.42 × 0.30 × 0.30 mm |
V = 872.5 (3) Å3 | |
Data collection top
Radiation source: fine-focus sealed tube | 1484 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
Absorption correction: multi-scan | θmax = 27.5°, θmin = 3.0° |
Tmin = 0.877, Tmax = 1.000 | h = −7→7 |
8786 measured reflections | k = −17→17 |
1998 independent reflections | l = −22→22 |
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.170 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0796P)2 + 0.758P] where P = (Fo2 + 2Fc2)/3 |
1998 reflections | (Δ/σ)max < 0.001 |
158 parameters | Δρmax = 0.73 e Å−3 |
79 restraints | Δρmin = −0.43 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C5 | 0.2160 (10) | 0.3410 (2) | 0.7842 (3) | 0.0523 (8) | |
H5A | 0.3117 | 0.2816 | 0.7893 | 0.063* | |
C4 | 0.0989 (9) | 0.4103 (2) | 0.7055 (3) | 0.0480 (8) | |
H4A | 0.1167 | 0.3988 | 0.6572 | 0.058* | |
C3 | −0.0461 (8) | 0.4974 (2) | 0.6984 (2) | 0.0401 (7) | |
C2 | −0.0763 (9) | 0.5125 (2) | 0.7695 (3) | 0.0474 (8) | |
H2A | −0.1809 | 0.5699 | 0.7639 | 0.057* | |
C1 | 0.0498 (10) | 0.4418 (3) | 0.8481 (3) | 0.0545 (9) | |
H1A | 0.0366 | 0.4513 | 0.8978 | 0.065* | |
C6 | −0.1607 (9) | 0.5780 (2) | 0.6177 (3) | 0.0464 (8) | |
N1 | 0.1921 (8) | 0.3590 (2) | 0.8532 (2) | 0.0511 (7) | |
H1B | 0.2719 | 0.3154 | 0.9034 | 0.061* | |
O1 | −0.3160 (7) | 0.65041 (17) | 0.6028 (2) | 0.0586 (7) | |
O2 | −0.0688 (9) | 0.55910 (19) | 0.5681 (2) | 0.0689 (8) | |
H2 | −0.1127 | 0.6072 | 0.5310 | 0.103* | |
Cl1 | −0.270 (4) | 0.8025 (10) | 0.4111 (13) | 0.0433 (8) | 0.33 |
O3 | −0.501 (7) | 0.811 (2) | 0.423 (3) | 0.0679 (17) | 0.33 |
O4 | −0.074 (5) | 0.7089 (8) | 0.4593 (10) | 0.0651 (16) | 0.33 |
O5 | −0.490 (6) | 0.8058 (11) | 0.2891 (11) | 0.072 (2) | 0.33 |
O6 | −0.013 (3) | 0.8843 (11) | 0.4694 (11) | 0.083 (2) | 0.33 |
Cl1B | −0.297 (4) | 0.8018 (10) | 0.4105 (12) | 0.0433 (8) | 0.33 |
O3B | −0.535 (6) | 0.8071 (19) | 0.418 (2) | 0.0679 (17) | 0.33 |
O4B | −0.030 (4) | 0.7313 (9) | 0.4892 (9) | 0.0651 (16) | 0.33 |
O5B | −0.494 (5) | 0.7760 (10) | 0.2991 (13) | 0.072 (2) | 0.33 |
O6B | −0.130 (3) | 0.8937 (11) | 0.4410 (13) | 0.083 (2) | 0.33 |
Cl1A | −0.319 (4) | 0.7909 (9) | 0.4047 (13) | 0.0433 (8) | 0.33 |
O3A | −0.557 (7) | 0.8203 (16) | 0.410 (3) | 0.0679 (17) | 0.33 |
O4A | −0.305 (3) | 0.6847 (6) | 0.4062 (7) | 0.0651 (16) | 0.33 |
O5A | −0.464 (8) | 0.8233 (14) | 0.2987 (13) | 0.072 (2) | 0.33 |
O6A | 0.030 (3) | 0.8306 (8) | 0.4991 (9) | 0.083 (2) | 0.33 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C5 | 0.065 (2) | 0.0362 (16) | 0.063 (2) | 0.0070 (15) | 0.049 (2) | 0.0059 (15) |
C4 | 0.065 (2) | 0.0375 (16) | 0.0520 (19) | 0.0014 (15) | 0.0466 (18) | −0.0031 (14) |
C3 | 0.0437 (16) | 0.0316 (14) | 0.0384 (15) | −0.0040 (12) | 0.0285 (14) | −0.0047 (12) |
C2 | 0.0575 (19) | 0.0372 (16) | 0.0578 (19) | 0.0023 (14) | 0.0459 (18) | −0.0019 (14) |
C1 | 0.071 (2) | 0.050 (2) | 0.059 (2) | −0.0027 (17) | 0.054 (2) | −0.0015 (16) |
C6 | 0.0542 (18) | 0.0348 (16) | 0.0408 (16) | −0.0044 (14) | 0.0324 (16) | −0.0039 (12) |
N1 | 0.0593 (17) | 0.0423 (15) | 0.0535 (16) | 0.0030 (13) | 0.0425 (15) | 0.0090 (12) |
O1 | 0.0688 (16) | 0.0388 (13) | 0.0634 (16) | 0.0119 (11) | 0.0476 (14) | 0.0105 (11) |
O2 | 0.111 (2) | 0.0501 (15) | 0.0719 (18) | 0.0153 (15) | 0.0760 (19) | 0.0140 (13) |
Cl1 | 0.0446 (16) | 0.0462 (13) | 0.0409 (9) | 0.0033 (11) | 0.0323 (12) | 0.0024 (9) |
O3 | 0.069 (4) | 0.081 (3) | 0.070 (4) | 0.015 (3) | 0.056 (4) | 0.007 (3) |
O4 | 0.083 (4) | 0.067 (4) | 0.064 (5) | 0.029 (4) | 0.060 (4) | 0.019 (3) |
O5 | 0.090 (3) | 0.078 (7) | 0.059 (2) | 0.012 (5) | 0.058 (2) | 0.021 (4) |
O6 | 0.069 (5) | 0.082 (4) | 0.081 (6) | −0.023 (4) | 0.051 (5) | −0.008 (4) |
Cl1B | 0.0446 (16) | 0.0462 (13) | 0.0409 (9) | 0.0033 (11) | 0.0323 (12) | 0.0024 (9) |
O3B | 0.069 (4) | 0.081 (3) | 0.070 (4) | 0.015 (3) | 0.056 (4) | 0.007 (3) |
O4B | 0.083 (4) | 0.067 (4) | 0.064 (5) | 0.029 (4) | 0.060 (4) | 0.019 (3) |
O5B | 0.090 (3) | 0.078 (7) | 0.059 (2) | 0.012 (5) | 0.058 (2) | 0.021 (4) |
O6B | 0.069 (5) | 0.082 (4) | 0.081 (6) | −0.023 (4) | 0.051 (5) | −0.008 (4) |
Cl1A | 0.0446 (16) | 0.0462 (13) | 0.0409 (9) | 0.0033 (11) | 0.0323 (12) | 0.0024 (9) |
O3A | 0.069 (4) | 0.081 (3) | 0.070 (4) | 0.015 (3) | 0.056 (4) | 0.007 (3) |
O4A | 0.083 (4) | 0.067 (4) | 0.064 (5) | 0.029 (4) | 0.060 (4) | 0.019 (3) |
O5A | 0.090 (3) | 0.078 (7) | 0.059 (2) | 0.012 (5) | 0.058 (2) | 0.021 (4) |
O6A | 0.069 (5) | 0.082 (4) | 0.081 (6) | −0.023 (4) | 0.051 (5) | −0.008 (4) |
Geometric parameters (Å, º) top
C5—N1 | 1.325 (4) | O2—H2 | 0.8200 |
C5—C4 | 1.367 (5) | Cl1—O3 | 1.442 (13) |
C5—H5A | 0.9300 | Cl1—O6 | 1.460 (13) |
C4—C3 | 1.380 (4) | Cl1—O4 | 1.462 (13) |
C4—H4A | 0.9300 | Cl1—O5 | 1.471 (13) |
C3—C2 | 1.383 (4) | Cl1B—O5B | 1.393 (15) |
C3—C6 | 1.501 (4) | Cl1B—O6B | 1.398 (14) |
C2—C1 | 1.367 (5) | Cl1B—O4B | 1.401 (14) |
C2—H2A | 0.9300 | Cl1B—O3B | 1.411 (15) |
C1—N1 | 1.335 (4) | Cl1A—O6A | 1.414 (12) |
C1—H1A | 0.9300 | Cl1A—O3A | 1.432 (12) |
C6—O1 | 1.198 (4) | Cl1A—O5A | 1.434 (12) |
C6—O2 | 1.310 (4) | Cl1A—O4A | 1.443 (12) |
N1—H1B | 0.8600 | | |
| | | |
N1—C5—C4 | 119.5 (3) | C1—N1—H1B | 118.5 |
N1—C5—H5A | 120.3 | C6—O2—H2 | 109.5 |
C4—C5—H5A | 120.3 | O3—Cl1—O6 | 110.0 (10) |
C5—C4—C3 | 119.4 (3) | O3—Cl1—O4 | 109.9 (10) |
C5—C4—H4A | 120.3 | O6—Cl1—O4 | 109.9 (9) |
C3—C4—H4A | 120.3 | O3—Cl1—O5 | 109.9 (10) |
C4—C3—C2 | 119.5 (3) | O6—Cl1—O5 | 108.4 (9) |
C4—C3—C6 | 121.5 (3) | O4—Cl1—O5 | 108.8 (9) |
C2—C3—C6 | 119.0 (3) | O5B—Cl1B—O6B | 111.5 (10) |
C1—C2—C3 | 119.0 (3) | O5B—Cl1B—O4B | 111.0 (10) |
C1—C2—H2A | 120.5 | O6B—Cl1B—O4B | 108.8 (9) |
C3—C2—H2A | 120.5 | O5B—Cl1B—O3B | 109.0 (10) |
N1—C1—C2 | 119.6 (3) | O6B—Cl1B—O3B | 108.1 (10) |
N1—C1—H1A | 120.2 | O4B—Cl1B—O3B | 108.4 (10) |
C2—C1—H1A | 120.2 | O6A—Cl1A—O3A | 109.8 (10) |
O1—C6—O2 | 125.5 (3) | O6A—Cl1A—O5A | 110.9 (10) |
O1—C6—C3 | 122.5 (3) | O3A—Cl1A—O5A | 109.6 (10) |
O2—C6—C3 | 112.0 (3) | O6A—Cl1A—O4A | 110.5 (9) |
C5—N1—C1 | 123.0 (3) | O3A—Cl1A—O4A | 108.4 (10) |
C5—N1—H1B | 118.5 | O5A—Cl1A—O4A | 107.5 (9) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···O3i | 0.86 | 2.25 | 2.94 (3) | 138 |
N1—H1B···O1i | 0.86 | 2.26 | 2.880 (4) | 129 |
N1—H1B···O3Ai | 0.86 | 2.34 | 3.01 (4) | 135 |
O2—H2···O4A | 0.82 | 1.88 | 2.666 (8) | 160 |
O2—H2···O4 | 0.82 | 1.98 | 2.767 (13) | 162 |
Symmetry code: (i) −x, y−1/2, −z+3/2. |
Crystal data top
C6H6ClNO6 | Z = 12 |
Mr = 223.57 | F(000) = 1368 |
Monoclinic, P21/c | Dx = 1.795 Mg m−3 |
a = 17.356 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.241 (3) Å | µ = 0.47 mm−1 |
c = 16.161 (7) Å | T = 103 K |
β = 138.055 (17)° | 0.42 × 0.30 × 0.30 mm |
V = 2482.3 (14) Å3 | |
Data collection top
Radiation source: fine-focus sealed tube | 4449 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
Absorption correction: multi-scan | θmax = 26.7°, θmin = 2.9° |
Tmin = 0.895, Tmax = 1.000 | h = −20→20 |
21324 measured reflections | k = −15→16 |
5031 independent reflections | l = −20→20 |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0656P)2 + 0.8233P] where P = (Fo2 + 2Fc2)/3 |
4908 reflections | (Δ/σ)max = 0.001 |
382 parameters | Δρmax = 0.45 e Å−3 |
0 restraints | Δρmin = −0.60 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.03957 (15) | 0.44437 (12) | 0.86614 (15) | 0.0169 (3) | |
H1B | 0.0417 | 0.4539 | 0.9260 | 0.020* | |
C2 | −0.01100 (14) | 0.51316 (12) | 0.78012 (14) | 0.0149 (3) | |
H2A | −0.0477 | 0.5714 | 0.7727 | 0.018* | |
C3 | −0.00538 (14) | 0.49267 (11) | 0.70540 (14) | 0.0137 (3) | |
C4 | 0.04540 (15) | 0.40228 (12) | 0.71448 (14) | 0.0164 (3) | |
H4A | 0.0449 | 0.3908 | 0.6561 | 0.020* | |
C5 | 0.09246 (15) | 0.33494 (12) | 0.80044 (15) | 0.0167 (3) | |
H5A | 0.1254 | 0.2739 | 0.8070 | 0.020* | |
C6 | −0.05019 (14) | 0.57231 (12) | 0.61896 (14) | 0.0144 (3) | |
C7 | 0.35985 (15) | 0.43912 (12) | 0.87583 (14) | 0.0167 (3) | |
H7A | 0.3597 | 0.4479 | 0.9341 | 0.020* | |
C8 | 0.31124 (14) | 0.50818 (12) | 0.79119 (14) | 0.0150 (3) | |
H8A | 0.2744 | 0.5665 | 0.7834 | 0.018* | |
C9 | 0.31889 (14) | 0.48811 (12) | 0.71766 (14) | 0.0140 (3) | |
C10 | 0.37074 (15) | 0.39828 (12) | 0.72766 (14) | 0.0163 (3) | |
H10A | 0.3714 | 0.3872 | 0.6701 | 0.020* | |
C11 | 0.41744 (15) | 0.33065 (12) | 0.81353 (14) | 0.0168 (3) | |
H11A | 0.4522 | 0.2703 | 0.8215 | 0.020* | |
C12 | 0.27544 (14) | 0.56836 (11) | 0.63220 (14) | 0.0147 (3) | |
C13 | 0.67983 (15) | 0.43640 (12) | 0.83007 (15) | 0.0180 (4) | |
H13A | 0.6676 | 0.4402 | 0.8784 | 0.022* | |
C14 | 0.63626 (15) | 0.50668 (12) | 0.74775 (15) | 0.0167 (3) | |
H14A | 0.5913 | 0.5615 | 0.7318 | 0.020* | |
CC15 | 0.66246 (14) | 0.49249 (11) | 0.68789 (13) | 0.0140 (3) | |
C16 | 0.72695 (14) | 0.40769 (12) | 0.70835 (14) | 0.0158 (3) | |
H16A | 0.7407 | 0.4018 | 0.6616 | 0.019* | |
C17 | 0.76679 (15) | 0.33871 (12) | 0.79037 (14) | 0.0166 (3) | |
H17A | 0.8087 | 0.2813 | 0.8055 | 0.020* | |
C18 | 0.62149 (14) | 0.57213 (12) | 0.60301 (13) | 0.0148 (3) | |
N1 | 0.09000 (12) | 0.35862 (10) | 0.87381 (12) | 0.0157 (3) | |
H1A | 0.1233 | 0.3169 | 0.9354 | 0.019* | |
N2 | 0.41173 (12) | 0.35345 (10) | 0.88470 (12) | 0.0160 (3) | |
H2B | 0.4435 | 0.3112 | 0.9454 | 0.019* | |
N3 | 0.74378 (12) | 0.35598 (10) | 0.84910 (12) | 0.0168 (3) | |
H3A | 0.7713 | 0.3124 | 0.9072 | 0.020* | |
Cl3 | 0.55612 (4) | 0.80167 (3) | 0.38250 (4) | 0.01354 (12) | |
Cl1 | −0.11025 (3) | 0.80359 (3) | 0.39994 (3) | 0.01273 (12) | |
Cl2 | 0.22941 (3) | 0.79584 (3) | 0.41991 (3) | 0.01364 (12) | |
O1 | −0.11127 (10) | 0.64368 (8) | 0.59645 (10) | 0.0174 (3) | |
O2 | −0.01290 (12) | 0.55395 (9) | 0.57319 (11) | 0.0218 (3) | |
H2 | −0.0239 | 0.6050 | 0.5345 | 0.033* | |
O3 | 0.21999 (10) | 0.64235 (8) | 0.61429 (10) | 0.0179 (3) | |
O4 | 0.30740 (12) | 0.54730 (8) | 0.58197 (11) | 0.0210 (3) | |
H4 | 0.2994 | 0.5987 | 0.5457 | 0.031* | |
O5 | 0.54958 (10) | 0.63833 (8) | 0.57009 (10) | 0.0184 (3) | |
O6 | 0.67288 (11) | 0.55969 (9) | 0.56980 (10) | 0.0204 (3) | |
H6 | 0.6591 | 0.6100 | 0.5287 | 0.031* | |
O7 | −0.19455 (11) | 0.80848 (8) | 0.40613 (11) | 0.0179 (3) | |
O8 | −0.02732 (12) | 0.71855 (9) | 0.46760 (11) | 0.0230 (3) | |
O9 | −0.17838 (11) | 0.79138 (9) | 0.28243 (11) | 0.0230 (3) | |
O10 | −0.03837 (12) | 0.89499 (9) | 0.44632 (12) | 0.0263 (3) | |
O11 | 0.14983 (11) | 0.80153 (9) | 0.43163 (11) | 0.0194 (3) | |
O12 | 0.30829 (11) | 0.70725 (8) | 0.48165 (11) | 0.0198 (3) | |
O13 | 0.15581 (12) | 0.78773 (9) | 0.30036 (11) | 0.0237 (3) | |
O14 | 0.30568 (12) | 0.88475 (9) | 0.46859 (11) | 0.0253 (3) | |
O15 | 0.47374 (11) | 0.79988 (8) | 0.39108 (11) | 0.0186 (3) | |
O16 | 0.65164 (11) | 0.72593 (9) | 0.45924 (11) | 0.0213 (3) | |
O17 | 0.48804 (11) | 0.78057 (10) | 0.26604 (11) | 0.0242 (3) | |
O18 | 0.61393 (12) | 0.89945 (9) | 0.41699 (12) | 0.0275 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0246 (9) | 0.0156 (8) | 0.0139 (8) | −0.0022 (6) | 0.0154 (7) | −0.0017 (6) |
C2 | 0.0196 (9) | 0.0137 (7) | 0.0136 (7) | 0.0000 (6) | 0.0130 (7) | −0.0010 (6) |
C3 | 0.0164 (8) | 0.0131 (7) | 0.0092 (7) | −0.0029 (6) | 0.0088 (7) | −0.0020 (5) |
C4 | 0.0245 (9) | 0.0144 (8) | 0.0129 (7) | 0.0003 (6) | 0.0147 (7) | −0.0002 (6) |
C5 | 0.0240 (9) | 0.0137 (8) | 0.0150 (8) | 0.0011 (6) | 0.0153 (7) | 0.0006 (6) |
C6 | 0.0173 (9) | 0.0132 (8) | 0.0088 (7) | −0.0023 (6) | 0.0085 (7) | −0.0021 (5) |
C7 | 0.0222 (9) | 0.0172 (8) | 0.0131 (7) | −0.0035 (7) | 0.0139 (7) | −0.0025 (6) |
C8 | 0.0194 (9) | 0.0141 (8) | 0.0141 (7) | −0.0013 (6) | 0.0132 (7) | −0.0023 (6) |
C9 | 0.0159 (8) | 0.0148 (8) | 0.0094 (7) | −0.0047 (6) | 0.0088 (7) | −0.0033 (5) |
C10 | 0.0229 (9) | 0.0156 (8) | 0.0124 (7) | −0.0012 (6) | 0.0138 (7) | −0.0018 (6) |
C11 | 0.0233 (9) | 0.0138 (8) | 0.0152 (8) | −0.0003 (6) | 0.0149 (7) | −0.0010 (6) |
C12 | 0.0177 (9) | 0.0134 (7) | 0.0094 (7) | −0.0032 (6) | 0.0090 (7) | −0.0029 (5) |
C13 | 0.0275 (10) | 0.0173 (8) | 0.0156 (8) | −0.0021 (7) | 0.0180 (8) | −0.0014 (6) |
C14 | 0.0222 (9) | 0.0149 (8) | 0.0157 (8) | −0.0011 (6) | 0.0149 (7) | −0.0016 (6) |
CC15 | 0.0170 (8) | 0.0141 (7) | 0.0074 (7) | −0.0040 (6) | 0.0081 (6) | −0.0027 (5) |
C16 | 0.0229 (9) | 0.0149 (8) | 0.0115 (7) | −0.0018 (6) | 0.0134 (7) | −0.0013 (6) |
C17 | 0.0224 (9) | 0.0150 (8) | 0.0139 (7) | 0.0006 (6) | 0.0139 (7) | −0.0005 (6) |
C18 | 0.0182 (9) | 0.0136 (8) | 0.0081 (7) | −0.0037 (6) | 0.0085 (7) | −0.0029 (5) |
N1 | 0.0229 (8) | 0.0144 (7) | 0.0109 (6) | −0.0002 (5) | 0.0129 (6) | 0.0011 (5) |
N2 | 0.0221 (8) | 0.0152 (7) | 0.0102 (6) | −0.0011 (5) | 0.0119 (6) | 0.0007 (5) |
N3 | 0.0246 (8) | 0.0159 (7) | 0.0108 (6) | −0.0011 (6) | 0.0134 (6) | 0.0009 (5) |
Cl3 | 0.0180 (2) | 0.0135 (2) | 0.0098 (2) | 0.00258 (13) | 0.01048 (18) | 0.00169 (12) |
Cl1 | 0.0166 (2) | 0.0132 (2) | 0.0084 (2) | 0.00131 (13) | 0.00928 (19) | 0.00084 (11) |
Cl2 | 0.0184 (2) | 0.0139 (2) | 0.0092 (2) | 0.00182 (14) | 0.01044 (18) | 0.00091 (12) |
O1 | 0.0227 (7) | 0.0142 (6) | 0.0117 (5) | 0.0023 (5) | 0.0118 (5) | 0.0017 (4) |
O2 | 0.0401 (8) | 0.0180 (6) | 0.0162 (6) | 0.0058 (5) | 0.0236 (6) | 0.0053 (4) |
O3 | 0.0237 (7) | 0.0147 (6) | 0.0125 (5) | 0.0013 (5) | 0.0127 (5) | 0.0010 (4) |
O4 | 0.0389 (8) | 0.0158 (6) | 0.0152 (6) | 0.0023 (5) | 0.0222 (6) | 0.0019 (4) |
O5 | 0.0229 (7) | 0.0159 (6) | 0.0124 (5) | 0.0013 (5) | 0.0119 (5) | 0.0017 (4) |
O6 | 0.0357 (7) | 0.0173 (6) | 0.0147 (6) | 0.0040 (5) | 0.0207 (6) | 0.0042 (4) |
O7 | 0.0240 (7) | 0.0219 (6) | 0.0124 (6) | 0.0014 (5) | 0.0149 (6) | −0.0002 (4) |
O8 | 0.0324 (8) | 0.0233 (6) | 0.0179 (6) | 0.0124 (5) | 0.0201 (6) | 0.0107 (5) |
O9 | 0.0275 (7) | 0.0311 (7) | 0.0070 (6) | 0.0045 (5) | 0.0118 (6) | 0.0009 (4) |
O10 | 0.0401 (8) | 0.0224 (7) | 0.0235 (7) | −0.0121 (6) | 0.0258 (7) | −0.0081 (5) |
O11 | 0.0262 (7) | 0.0241 (6) | 0.0134 (6) | 0.0035 (5) | 0.0164 (6) | 0.0012 (4) |
O12 | 0.0278 (7) | 0.0189 (6) | 0.0135 (6) | 0.0083 (5) | 0.0156 (6) | 0.0060 (4) |
O13 | 0.0294 (8) | 0.0303 (7) | 0.0077 (6) | 0.0071 (5) | 0.0127 (6) | 0.0026 (4) |
O14 | 0.0367 (8) | 0.0197 (6) | 0.0214 (6) | −0.0073 (5) | 0.0222 (6) | −0.0036 (5) |
O15 | 0.0247 (7) | 0.0236 (6) | 0.0116 (6) | 0.0033 (5) | 0.0147 (6) | 0.0021 (4) |
O16 | 0.0254 (7) | 0.0230 (6) | 0.0153 (6) | 0.0093 (5) | 0.0151 (6) | 0.0090 (5) |
O17 | 0.0270 (7) | 0.0356 (7) | 0.0067 (6) | 0.0048 (5) | 0.0115 (6) | 0.0003 (5) |
O18 | 0.0471 (9) | 0.0172 (6) | 0.0288 (7) | −0.0063 (6) | 0.0314 (7) | −0.0034 (5) |
Geometric parameters (Å, º) top
C1—C2 | 1.310 (2) | C14—CC15 | 1.354 (2) |
C1—N1 | 1.382 (2) | C14—H14A | 0.9500 |
C1—H1B | 0.9500 | CC15—C18 | 1.431 (2) |
C2—C3 | 1.310 (2) | CC15—C16 | 1.439 (2) |
C2—H2A | 0.9500 | C16—C17 | 1.306 (2) |
C3—C4 | 1.428 (2) | C16—H16A | 0.9500 |
C3—C6 | 1.433 (2) | C17—N3 | 1.295 (2) |
C4—C5 | 1.305 (2) | C17—H17A | 0.9500 |
C4—H4A | 0.9500 | C18—O5 | 1.273 (2) |
C5—N1 | 1.257 (2) | C18—O6 | 1.350 (2) |
C5—H5A | 0.9500 | N1—H1A | 0.8800 |
C6—O1 | 1.255 (2) | N2—H2B | 0.8800 |
C6—O2 | 1.318 (2) | N3—H3A | 0.8800 |
C7—C8 | 1.305 (2) | Cl3—O17 | 1.3070 (13) |
C7—N2 | 1.388 (2) | Cl3—O18 | 1.4702 (13) |
C7—H7A | 0.9500 | Cl3—O16 | 1.4946 (13) |
C8—C9 | 1.317 (2) | Cl3—O15 | 1.5358 (13) |
C8—H8A | 0.9500 | Cl1—O9 | 1.3001 (14) |
C9—C10 | 1.426 (2) | Cl1—O10 | 1.4805 (13) |
C9—C12 | 1.434 (2) | Cl1—O8 | 1.4812 (13) |
C10—C11 | 1.308 (2) | Cl1—O7 | 1.5403 (13) |
C10—H10A | 0.9500 | Cl2—O13 | 1.3056 (14) |
C11—N2 | 1.262 (2) | Cl2—O14 | 1.4859 (13) |
C11—H11A | 0.9500 | Cl2—O12 | 1.4878 (12) |
C12—O3 | 1.247 (2) | Cl2—O11 | 1.5293 (13) |
C12—O4 | 1.309 (2) | O2—H2 | 0.8400 |
C13—C14 | 1.308 (2) | O4—H4 | 0.8400 |
C13—N3 | 1.397 (2) | O6—H6 | 0.8400 |
C13—H13A | 0.9500 | | |
| | | |
C2—C1—N1 | 123.09 (14) | C14—CC15—C18 | 113.03 (15) |
C2—C1—H1B | 118.5 | C14—CC15—C16 | 124.14 (14) |
N1—C1—H1B | 118.5 | C18—CC15—C16 | 122.82 (14) |
C3—C2—C1 | 112.56 (16) | C17—C16—CC15 | 120.86 (15) |
C3—C2—H2A | 123.7 | C17—C16—H16A | 119.6 |
C1—C2—H2A | 123.7 | CC15—C16—H16A | 119.6 |
C2—C3—C4 | 122.84 (15) | N3—C17—C16 | 113.66 (16) |
C2—C3—C6 | 112.82 (15) | N3—C17—H17A | 123.2 |
C4—C3—C6 | 124.27 (14) | C16—C17—H17A | 123.2 |
C5—C4—C3 | 122.12 (15) | O5—C18—O6 | 130.54 (14) |
C5—C4—H4A | 118.9 | O5—C18—CC15 | 122.79 (14) |
C3—C4—H4A | 118.9 | O6—C18—CC15 | 106.67 (14) |
N1—C5—C4 | 113.58 (16) | C5—N1—C1 | 125.72 (14) |
N1—C5—H5A | 123.2 | C5—N1—H1A | 117.1 |
C4—C5—H5A | 123.2 | C1—N1—H1A | 117.1 |
O1—C6—O2 | 129.62 (14) | C11—N2—C7 | 125.87 (14) |
O1—C6—C3 | 124.44 (14) | C11—N2—H2B | 117.1 |
O2—C6—C3 | 105.94 (14) | C7—N2—H2B | 117.1 |
C8—C7—N2 | 123.03 (14) | C17—N3—C13 | 126.93 (14) |
C8—C7—H7A | 118.5 | C17—N3—H3A | 116.5 |
N2—C7—H7A | 118.5 | C13—N3—H3A | 116.5 |
C7—C8—C9 | 112.58 (16) | O17—Cl3—O18 | 111.42 (8) |
C7—C8—H8A | 123.7 | O17—Cl3—O16 | 107.95 (8) |
C9—C8—H8A | 123.7 | O18—Cl3—O16 | 104.67 (8) |
C8—C9—C10 | 122.99 (15) | O17—Cl3—O15 | 102.80 (8) |
C8—C9—C12 | 112.70 (15) | O18—Cl3—O15 | 113.45 (7) |
C10—C9—C12 | 124.23 (14) | O16—Cl3—O15 | 116.57 (7) |
C11—C10—C9 | 122.12 (15) | O9—Cl1—O10 | 110.46 (8) |
C11—C10—H10A | 118.9 | O9—Cl1—O8 | 108.20 (8) |
C9—C10—H10A | 118.9 | O10—Cl1—O8 | 104.92 (8) |
N2—C11—C10 | 113.35 (16) | O9—Cl1—O7 | 102.96 (9) |
N2—C11—H11A | 123.3 | O10—Cl1—O7 | 114.60 (7) |
C10—C11—H11A | 123.3 | O8—Cl1—O7 | 115.62 (7) |
O3—C12—O4 | 129.27 (14) | O13—Cl2—O14 | 110.76 (8) |
O3—C12—C9 | 124.60 (14) | O13—Cl2—O12 | 109.09 (7) |
O4—C12—C9 | 106.12 (14) | O14—Cl2—O12 | 104.86 (8) |
C14—C13—N3 | 121.98 (14) | O13—Cl2—O11 | 101.99 (9) |
C14—C13—H13A | 119.0 | O14—Cl2—O11 | 115.24 (7) |
N3—C13—H13A | 119.0 | O12—Cl2—O11 | 114.90 (7) |
C13—C14—CC15 | 112.38 (16) | C6—O2—H2 | 109.5 |
C13—C14—H14A | 123.8 | C12—O4—H4 | 109.5 |
CC15—C14—H14A | 123.8 | C18—O6—H6 | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O7i | 0.88 | 1.84 | 2.604 (2) | 144 |
N1—H1A···O1i | 0.88 | 2.33 | 2.8641 (18) | 120 |
N2—H2B···O15ii | 0.88 | 1.85 | 2.621 (2) | 145 |
N2—H2B···O5ii | 0.88 | 2.32 | 2.8928 (18) | 123 |
N3—H3A···O11ii | 0.88 | 1.84 | 2.599 (2) | 144 |
N3—H3A···O3ii | 0.88 | 2.30 | 2.8624 (18) | 122 |
O2—H2···O8 | 0.84 | 1.83 | 2.6625 (17) | 172 |
O4—H4···O12 | 0.84 | 1.84 | 2.6742 (17) | 170 |
O6—H6···O16 | 0.84 | 1.85 | 2.6821 (17) | 171 |
Symmetry codes: (i) −x, y−1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2. |
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