Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802020445/na6180sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802020445/na6180Isup2.hkl |
CCDC reference: 202333
Key indicators
- Single-crystal X-ray study
- T = 148 K
- Mean (C-C) = 0.002 Å
- R factor = 0.049
- wR factor = 0.124
- Data-to-parameter ratio = 23.5
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
3-Phenylpyrazole was synthesized as reported by Buchner & Hachumian (1902). Single crystals suitable for data collection were obtained by recrystallization from chloroform at ambient temperature.
A difference Fourier synthesis showed all six independent molecules to be protonated at the N atom labeled N2. The H atoms were positioned geometrically and were refined with fixed individual isotropic displacement parameters [Uiso(H) = 1.2Ueq(C,N)], using a riding model with fixed distances [H—C = 0.95 Å and H—N = 0.88 Å]. The crystal was found not to be twinned, despite the observed pseudosymmetry and the almost equal values of the lattice parameters a and b and the angles α and β.
Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1996); software used to prepare material for publication: SHELXL97.
C9H8N2 | Z = 12 |
Mr = 144.17 | F(000) = 912 |
Triclinic, P1 | Dx = 1.262 Mg m−3 |
a = 12.1514 (10) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.3120 (11) Å | Cell parameters from 324 reflections |
c = 17.114 (2) Å | θ = 3–26° |
α = 88.164 (11)° | µ = 0.08 mm−1 |
β = 88.103 (12)° | T = 148 K |
γ = 62.816 (6)° | Block, colorless |
V = 2275.9 (4) Å3 | 0.50 × 0.48 × 0.40 mm |
Siemens SMART CCD diffractometer | 14026 independent reflections |
Radiation source: normal-focus sealed tube | 10303 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
ω scans | θmax = 31.0°, θmin = 1.9° |
Absorption correction: numerical (SHELXTL; Sheldrick, 1996) | h = −17→17 |
Tmin = 0.959, Tmax = 0.975 | k = −17→17 |
40438 measured reflections | l = −23→24 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.124 | w = 1/[σ2(Fo2) + (0.04P)2 + 0.9P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
14026 reflections | Δρmax = 0.34 e Å−3 |
596 parameters | Δρmin = −0.27 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0011 (3) |
C9H8N2 | γ = 62.816 (6)° |
Mr = 144.17 | V = 2275.9 (4) Å3 |
Triclinic, P1 | Z = 12 |
a = 12.1514 (10) Å | Mo Kα radiation |
b = 12.3120 (11) Å | µ = 0.08 mm−1 |
c = 17.114 (2) Å | T = 148 K |
α = 88.164 (11)° | 0.50 × 0.48 × 0.40 mm |
β = 88.103 (12)° |
Siemens SMART CCD diffractometer | 14026 independent reflections |
Absorption correction: numerical (SHELXTL; Sheldrick, 1996) | 10303 reflections with I > 2σ(I) |
Tmin = 0.959, Tmax = 0.975 | Rint = 0.038 |
40438 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.34 e Å−3 |
14026 reflections | Δρmin = −0.27 e Å−3 |
596 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 | ||
N1A | 0.26055 (10) | 0.44741 (10) | 0.47252 (6) | 0.0248 (2) | |
N2A | 0.20349 (10) | 0.56046 (10) | 0.50295 (6) | 0.0272 (2) | |
H2NA | 0.2181 | 0.6213 | 0.4868 | 0.033* | |
C1A | 0.12195 (13) | 0.56947 (13) | 0.56055 (8) | 0.0316 (3) | |
H1A | 0.0720 | 0.6401 | 0.5899 | 0.038* | |
C2A | 0.12483 (12) | 0.45679 (12) | 0.56871 (8) | 0.0296 (3) | |
H2A | 0.0776 | 0.4336 | 0.6046 | 0.036* | |
C3A | 0.21228 (11) | 0.38318 (11) | 0.51294 (7) | 0.0223 (2) | |
C4A | 0.25082 (11) | 0.25374 (11) | 0.49731 (7) | 0.0237 (2) | |
C5A | 0.35027 (15) | 0.18583 (14) | 0.44807 (10) | 0.0440 (4) | |
H5A | 0.3970 | 0.2225 | 0.4241 | 0.053* | |
C6A | 0.38200 (18) | 0.06489 (15) | 0.43349 (12) | 0.0548 (5) | |
H6A | 0.4494 | 0.0201 | 0.3988 | 0.066* | |
C7A | 0.31724 (16) | 0.00867 (14) | 0.46848 (10) | 0.0418 (4) | |
H7A | 0.3399 | −0.0744 | 0.4585 | 0.050* | |
C8A | 0.21936 (15) | 0.07459 (14) | 0.51800 (10) | 0.0407 (3) | |
H8A | 0.1746 | 0.0365 | 0.5429 | 0.049* | |
C9A | 0.18526 (13) | 0.19654 (13) | 0.53192 (9) | 0.0347 (3) | |
H9A | 0.1163 | 0.2414 | 0.5655 | 0.042* | |
N1B | 0.30697 (10) | 0.70842 (10) | 0.42865 (6) | 0.0259 (2) | |
N2B | 0.42373 (10) | 0.66906 (11) | 0.45362 (7) | 0.0290 (2) | |
H2NB | 0.4462 | 0.6470 | 0.5023 | 0.035* | |
C1B | 0.50110 (14) | 0.66756 (15) | 0.39560 (9) | 0.0374 (3) | |
H1B | 0.5869 | 0.6435 | 0.3998 | 0.045* | |
C2B | 0.43328 (13) | 0.70722 (15) | 0.32898 (8) | 0.0364 (3) | |
H2B | 0.4620 | 0.7161 | 0.2780 | 0.044* | |
C3B | 0.31204 (12) | 0.73206 (11) | 0.35213 (7) | 0.0245 (2) | |
C4B | 0.20062 (11) | 0.77751 (11) | 0.30429 (7) | 0.0238 (2) | |
C5B | 0.08326 (12) | 0.81235 (12) | 0.33827 (8) | 0.0291 (3) | |
H5B | 0.0747 | 0.8062 | 0.3934 | 0.035* | |
C6B | −0.02066 (13) | 0.85566 (14) | 0.29232 (9) | 0.0341 (3) | |
H6B | −0.0998 | 0.8791 | 0.3162 | 0.041* | |
C7B | −0.00999 (13) | 0.86495 (13) | 0.21178 (9) | 0.0337 (3) | |
H7B | −0.0813 | 0.8945 | 0.1804 | 0.040* | |
C8B | 0.10556 (14) | 0.83080 (13) | 0.17754 (8) | 0.0334 (3) | |
H8B | 0.1135 | 0.8369 | 0.1224 | 0.040* | |
C9B | 0.20978 (12) | 0.78783 (12) | 0.22310 (8) | 0.0294 (3) | |
H9B | 0.2885 | 0.7651 | 0.1988 | 0.035* | |
N1C | 0.44277 (10) | 0.65673 (10) | 0.62598 (6) | 0.0256 (2) | |
N2C | 0.55701 (10) | 0.59322 (10) | 0.65585 (7) | 0.0282 (2) | |
H2NC | 0.6259 | 0.5675 | 0.6277 | 0.034* | |
C1C | 0.55327 (13) | 0.57385 (14) | 0.73327 (8) | 0.0325 (3) | |
H1C | 0.6223 | 0.5314 | 0.7660 | 0.039* | |
C2C | 0.43054 (12) | 0.62703 (13) | 0.75635 (8) | 0.0304 (3) | |
H2C | 0.3975 | 0.6287 | 0.8076 | 0.036* | |
C3C | 0.36453 (11) | 0.67838 (11) | 0.68750 (7) | 0.0235 (2) | |
C4C | 0.22988 (11) | 0.75014 (11) | 0.67840 (7) | 0.0233 (2) | |
C5C | 0.17983 (12) | 0.81181 (12) | 0.60846 (8) | 0.0278 (3) | |
H5C | 0.2333 | 0.8092 | 0.5660 | 0.033* | |
C6C | 0.05273 (13) | 0.87690 (12) | 0.60035 (9) | 0.0317 (3) | |
H6C | 0.0199 | 0.9176 | 0.5522 | 0.038* | |
C7C | −0.02701 (13) | 0.88310 (13) | 0.66198 (9) | 0.0330 (3) | |
H7C | −0.1141 | 0.9272 | 0.6561 | 0.040* | |
C8C | 0.02178 (13) | 0.82440 (14) | 0.73198 (9) | 0.0343 (3) | |
H8C | −0.0321 | 0.8293 | 0.7747 | 0.041* | |
C9C | 0.14889 (12) | 0.75834 (13) | 0.74044 (8) | 0.0292 (3) | |
H9C | 0.1811 | 0.7183 | 0.7889 | 0.035* | |
N1D | 0.54292 (9) | 0.25111 (10) | 0.02935 (6) | 0.0245 (2) | |
N2D | 0.43726 (10) | 0.29149 (10) | −0.01128 (7) | 0.0273 (2) | |
H2ND | 0.3775 | 0.2719 | 0.0007 | 0.033* | |
C1D | 0.43390 (12) | 0.36477 (13) | −0.07198 (8) | 0.0299 (3) | |
H1D | 0.3693 | 0.4024 | −0.1084 | 0.036* | |
C2D | 0.54199 (12) | 0.37498 (12) | −0.07127 (8) | 0.0279 (3) | |
H2D | 0.5668 | 0.4214 | −0.1064 | 0.033* | |
C3D | 0.60770 (11) | 0.30204 (11) | −0.00755 (7) | 0.0224 (2) | |
C4D | 0.73465 (11) | 0.27131 (11) | 0.01532 (7) | 0.0230 (2) | |
C5D | 0.81000 (12) | 0.15966 (13) | 0.05140 (8) | 0.0303 (3) | |
H5D | 0.7772 | 0.1049 | 0.0659 | 0.036* | |
C6D | 0.93282 (13) | 0.12792 (15) | 0.06627 (9) | 0.0374 (3) | |
H6D | 0.9833 | 0.0519 | 0.0913 | 0.045* | |
C7D | 0.98223 (13) | 0.20627 (15) | 0.04491 (9) | 0.0367 (3) | |
H7D | 1.0667 | 0.1837 | 0.0542 | 0.044* | |
C8D | 0.90778 (13) | 0.31742 (14) | 0.00997 (9) | 0.0355 (3) | |
H8D | 0.9411 | 0.3718 | −0.0043 | 0.043* | |
C9D | 0.78459 (12) | 0.35070 (13) | −0.00456 (8) | 0.0297 (3) | |
H9D | 0.7341 | 0.4279 | −0.0282 | 0.036* | |
N1E | 0.30245 (9) | 0.17144 (10) | 0.05880 (6) | 0.0244 (2) | |
N2E | 0.34159 (10) | 0.05433 (10) | 0.03747 (6) | 0.0269 (2) | |
H2NE | 0.3644 | 0.0283 | −0.0105 | 0.032* | |
C1E | 0.34147 (13) | −0.01718 (13) | 0.09805 (8) | 0.0318 (3) | |
H1E | 0.3648 | −0.1020 | 0.0965 | 0.038* | |
C2E | 0.30139 (13) | 0.05464 (12) | 0.16290 (8) | 0.0293 (3) | |
H2E | 0.2917 | 0.0303 | 0.2148 | 0.035* | |
C3E | 0.27782 (11) | 0.17208 (11) | 0.13579 (7) | 0.0219 (2) | |
C4E | 0.22847 (11) | 0.28677 (11) | 0.17925 (7) | 0.0223 (2) | |
C5E | 0.19739 (12) | 0.39876 (12) | 0.14094 (8) | 0.0273 (3) | |
H5E | 0.2108 | 0.4010 | 0.0860 | 0.033* | |
C6E | 0.14723 (12) | 0.50671 (13) | 0.18213 (9) | 0.0318 (3) | |
H6E | 0.1271 | 0.5820 | 0.1554 | 0.038* | |
C7E | 0.12634 (12) | 0.50495 (13) | 0.26217 (9) | 0.0329 (3) | |
H7E | 0.0914 | 0.5789 | 0.2903 | 0.040* | |
C8E | 0.15679 (13) | 0.39476 (13) | 0.30076 (8) | 0.0320 (3) | |
H8E | 0.1424 | 0.3932 | 0.3556 | 0.038* | |
C9E | 0.20830 (12) | 0.28622 (13) | 0.25977 (8) | 0.0279 (3) | |
H9E | 0.2299 | 0.2110 | 0.2870 | 0.034* | |
N1F | 0.35696 (10) | 0.02490 (10) | −0.13406 (6) | 0.0253 (2) | |
N2F | 0.41541 (10) | −0.08788 (10) | −0.16458 (6) | 0.0275 (2) | |
H2NF | 0.4435 | −0.1558 | −0.1363 | 0.033* | |
C1F | 0.42582 (13) | −0.08467 (13) | −0.24280 (8) | 0.0313 (3) | |
H1F | 0.4634 | −0.1531 | −0.2760 | 0.038* | |
C2F | 0.37204 (13) | 0.03594 (13) | −0.26583 (8) | 0.0302 (3) | |
H2F | 0.3647 | 0.0682 | −0.3176 | 0.036* | |
C3F | 0.33003 (11) | 0.10171 (12) | −0.19607 (7) | 0.0242 (2) | |
C4F | 0.26381 (11) | 0.23455 (12) | −0.18656 (7) | 0.0242 (2) | |
C5F | 0.19203 (11) | 0.28561 (12) | −0.11925 (7) | 0.0262 (3) | |
H5F | 0.1853 | 0.2338 | −0.0790 | 0.031* | |
C6F | 0.13088 (12) | 0.41101 (13) | −0.11092 (8) | 0.0300 (3) | |
H6F | 0.0834 | 0.4444 | −0.0647 | 0.036* | |
C7F | 0.13799 (12) | 0.48874 (13) | −0.16928 (8) | 0.0313 (3) | |
H7F | 0.0952 | 0.5748 | −0.1633 | 0.038* | |
C8F | 0.20818 (14) | 0.43944 (13) | −0.23626 (8) | 0.0334 (3) | |
H8F | 0.2138 | 0.4919 | −0.2764 | 0.040* | |
C9F | 0.27046 (13) | 0.31354 (13) | −0.24499 (8) | 0.0304 (3) | |
H9F | 0.3182 | 0.2807 | −0.2913 | 0.036* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0271 (5) | 0.0256 (5) | 0.0245 (5) | −0.0145 (4) | 0.0019 (4) | 0.0002 (4) |
N2A | 0.0321 (6) | 0.0249 (5) | 0.0285 (6) | −0.0167 (5) | 0.0018 (4) | 0.0004 (4) |
C1A | 0.0361 (7) | 0.0297 (7) | 0.0314 (7) | −0.0172 (6) | 0.0085 (6) | −0.0062 (5) |
C2A | 0.0326 (7) | 0.0310 (7) | 0.0291 (6) | −0.0183 (6) | 0.0094 (5) | −0.0039 (5) |
C3A | 0.0227 (5) | 0.0260 (6) | 0.0202 (5) | −0.0130 (5) | −0.0012 (4) | 0.0018 (4) |
C4A | 0.0252 (6) | 0.0248 (6) | 0.0218 (6) | −0.0121 (5) | −0.0014 (4) | 0.0018 (5) |
C5A | 0.0445 (9) | 0.0289 (7) | 0.0555 (10) | −0.0157 (7) | 0.0233 (7) | −0.0030 (7) |
C6A | 0.0592 (11) | 0.0301 (8) | 0.0651 (12) | −0.0132 (8) | 0.0305 (9) | −0.0094 (8) |
C7A | 0.0515 (9) | 0.0251 (7) | 0.0477 (9) | −0.0166 (7) | −0.0004 (7) | −0.0017 (6) |
C8A | 0.0451 (8) | 0.0326 (8) | 0.0524 (9) | −0.0250 (7) | 0.0023 (7) | 0.0006 (7) |
C9A | 0.0358 (7) | 0.0300 (7) | 0.0427 (8) | −0.0193 (6) | 0.0090 (6) | −0.0040 (6) |
N1B | 0.0298 (5) | 0.0270 (5) | 0.0239 (5) | −0.0158 (5) | 0.0018 (4) | 0.0003 (4) |
N2B | 0.0318 (6) | 0.0347 (6) | 0.0238 (5) | −0.0180 (5) | −0.0028 (4) | 0.0032 (4) |
C1B | 0.0306 (7) | 0.0550 (10) | 0.0314 (7) | −0.0238 (7) | 0.0003 (6) | 0.0030 (7) |
C2B | 0.0307 (7) | 0.0562 (9) | 0.0265 (7) | −0.0239 (7) | 0.0031 (5) | 0.0023 (6) |
C3B | 0.0285 (6) | 0.0246 (6) | 0.0238 (6) | −0.0153 (5) | 0.0046 (5) | −0.0024 (5) |
C4B | 0.0278 (6) | 0.0215 (6) | 0.0249 (6) | −0.0137 (5) | 0.0030 (5) | −0.0025 (5) |
C5B | 0.0304 (6) | 0.0314 (7) | 0.0277 (6) | −0.0164 (6) | 0.0046 (5) | −0.0006 (5) |
C6B | 0.0287 (7) | 0.0368 (8) | 0.0399 (8) | −0.0179 (6) | 0.0028 (6) | 0.0012 (6) |
C7B | 0.0331 (7) | 0.0318 (7) | 0.0378 (8) | −0.0160 (6) | −0.0069 (6) | 0.0012 (6) |
C8B | 0.0397 (8) | 0.0320 (7) | 0.0256 (7) | −0.0137 (6) | −0.0016 (6) | −0.0018 (5) |
C9B | 0.0297 (6) | 0.0302 (7) | 0.0261 (6) | −0.0118 (5) | 0.0046 (5) | −0.0030 (5) |
N1C | 0.0247 (5) | 0.0279 (5) | 0.0255 (5) | −0.0133 (4) | 0.0033 (4) | −0.0011 (4) |
N2C | 0.0229 (5) | 0.0320 (6) | 0.0295 (6) | −0.0127 (5) | 0.0042 (4) | 0.0006 (4) |
C1C | 0.0280 (6) | 0.0385 (8) | 0.0297 (7) | −0.0144 (6) | −0.0013 (5) | 0.0052 (6) |
C2C | 0.0287 (6) | 0.0364 (7) | 0.0247 (6) | −0.0141 (6) | 0.0032 (5) | 0.0014 (5) |
C3C | 0.0264 (6) | 0.0233 (6) | 0.0243 (6) | −0.0146 (5) | 0.0037 (5) | −0.0021 (5) |
C4C | 0.0261 (6) | 0.0215 (6) | 0.0253 (6) | −0.0134 (5) | 0.0025 (5) | −0.0031 (5) |
C5C | 0.0314 (6) | 0.0243 (6) | 0.0287 (6) | −0.0136 (5) | 0.0041 (5) | −0.0007 (5) |
C6C | 0.0334 (7) | 0.0249 (6) | 0.0350 (7) | −0.0119 (6) | −0.0034 (6) | 0.0042 (5) |
C7C | 0.0256 (6) | 0.0288 (7) | 0.0434 (8) | −0.0115 (5) | 0.0002 (6) | −0.0013 (6) |
C8C | 0.0281 (6) | 0.0407 (8) | 0.0359 (7) | −0.0175 (6) | 0.0064 (6) | −0.0025 (6) |
C9C | 0.0274 (6) | 0.0346 (7) | 0.0275 (6) | −0.0160 (6) | 0.0027 (5) | −0.0002 (5) |
N1D | 0.0230 (5) | 0.0257 (5) | 0.0261 (5) | −0.0125 (4) | 0.0024 (4) | −0.0006 (4) |
N2D | 0.0215 (5) | 0.0316 (6) | 0.0311 (6) | −0.0142 (4) | 0.0029 (4) | −0.0008 (4) |
C1D | 0.0238 (6) | 0.0322 (7) | 0.0309 (7) | −0.0106 (5) | −0.0016 (5) | 0.0033 (5) |
C2D | 0.0258 (6) | 0.0282 (6) | 0.0292 (6) | −0.0122 (5) | 0.0020 (5) | 0.0040 (5) |
C3D | 0.0224 (5) | 0.0210 (5) | 0.0244 (6) | −0.0105 (5) | 0.0039 (4) | −0.0022 (4) |
C4D | 0.0229 (5) | 0.0258 (6) | 0.0216 (6) | −0.0123 (5) | 0.0028 (4) | −0.0030 (5) |
C5D | 0.0283 (6) | 0.0334 (7) | 0.0307 (7) | −0.0157 (6) | −0.0006 (5) | 0.0052 (5) |
C6D | 0.0281 (7) | 0.0443 (8) | 0.0348 (8) | −0.0125 (6) | −0.0053 (6) | 0.0070 (6) |
C7D | 0.0254 (6) | 0.0560 (10) | 0.0324 (7) | −0.0214 (7) | −0.0008 (5) | −0.0051 (7) |
C8D | 0.0351 (7) | 0.0430 (8) | 0.0393 (8) | −0.0272 (7) | 0.0052 (6) | −0.0083 (6) |
C9D | 0.0301 (6) | 0.0278 (6) | 0.0349 (7) | −0.0165 (5) | 0.0030 (5) | −0.0032 (5) |
N1E | 0.0251 (5) | 0.0286 (5) | 0.0228 (5) | −0.0151 (4) | 0.0011 (4) | −0.0018 (4) |
N2E | 0.0297 (5) | 0.0296 (6) | 0.0236 (5) | −0.0153 (5) | 0.0044 (4) | −0.0062 (4) |
C1E | 0.0379 (7) | 0.0261 (6) | 0.0314 (7) | −0.0147 (6) | 0.0061 (6) | −0.0034 (5) |
C2E | 0.0357 (7) | 0.0273 (6) | 0.0248 (6) | −0.0146 (6) | 0.0043 (5) | −0.0002 (5) |
C3E | 0.0192 (5) | 0.0262 (6) | 0.0221 (6) | −0.0120 (5) | −0.0005 (4) | −0.0004 (5) |
C4E | 0.0193 (5) | 0.0262 (6) | 0.0235 (6) | −0.0121 (5) | −0.0012 (4) | −0.0018 (5) |
C5E | 0.0259 (6) | 0.0291 (6) | 0.0274 (6) | −0.0131 (5) | −0.0014 (5) | 0.0011 (5) |
C6E | 0.0278 (6) | 0.0261 (6) | 0.0415 (8) | −0.0121 (5) | −0.0039 (6) | 0.0005 (6) |
C7E | 0.0276 (6) | 0.0312 (7) | 0.0402 (8) | −0.0130 (6) | 0.0007 (6) | −0.0113 (6) |
C8E | 0.0341 (7) | 0.0380 (7) | 0.0263 (6) | −0.0182 (6) | 0.0013 (5) | −0.0083 (6) |
C9E | 0.0307 (6) | 0.0304 (7) | 0.0247 (6) | −0.0156 (5) | 0.0000 (5) | −0.0023 (5) |
N1F | 0.0274 (5) | 0.0269 (5) | 0.0236 (5) | −0.0143 (4) | 0.0011 (4) | 0.0000 (4) |
N2F | 0.0299 (5) | 0.0272 (5) | 0.0272 (5) | −0.0146 (5) | 0.0013 (4) | 0.0000 (4) |
C1F | 0.0349 (7) | 0.0334 (7) | 0.0270 (7) | −0.0169 (6) | 0.0038 (5) | −0.0050 (5) |
C2F | 0.0344 (7) | 0.0351 (7) | 0.0218 (6) | −0.0165 (6) | 0.0020 (5) | −0.0001 (5) |
C3F | 0.0233 (6) | 0.0310 (6) | 0.0220 (6) | −0.0156 (5) | −0.0005 (4) | 0.0012 (5) |
C4F | 0.0220 (5) | 0.0298 (6) | 0.0230 (6) | −0.0137 (5) | −0.0032 (4) | 0.0027 (5) |
C5F | 0.0247 (6) | 0.0310 (6) | 0.0247 (6) | −0.0145 (5) | 0.0001 (5) | 0.0023 (5) |
C6F | 0.0251 (6) | 0.0324 (7) | 0.0321 (7) | −0.0127 (5) | 0.0021 (5) | −0.0023 (5) |
C7F | 0.0283 (6) | 0.0279 (7) | 0.0377 (7) | −0.0128 (5) | −0.0058 (5) | 0.0030 (5) |
C8F | 0.0397 (7) | 0.0342 (7) | 0.0297 (7) | −0.0202 (6) | −0.0060 (6) | 0.0085 (6) |
C9F | 0.0354 (7) | 0.0345 (7) | 0.0242 (6) | −0.0189 (6) | 0.0007 (5) | 0.0028 (5) |
N1A—C3A | 1.3453 (15) | N1D—C3D | 1.3432 (15) |
N1A—N2A | 1.3528 (15) | N1D—N2D | 1.3538 (15) |
N2A—C1A | 1.3444 (17) | N2D—C1D | 1.3431 (18) |
N2A—H2NA | 0.8800 | N2D—H2ND | 0.8800 |
C1A—C2A | 1.3744 (19) | C1D—C2D | 1.3759 (18) |
C1A—H1A | 0.9500 | C1D—H1D | 0.9500 |
C2A—C3A | 1.4036 (17) | C2D—C3D | 1.4046 (19) |
C2A—H2A | 0.9500 | C2D—H2D | 0.9500 |
C3A—C4A | 1.4724 (17) | C3D—C4D | 1.4742 (17) |
C4A—C5A | 1.3871 (19) | C4D—C5D | 1.3937 (19) |
C4A—C9A | 1.3915 (18) | C4D—C9D | 1.3951 (17) |
C5A—C6A | 1.386 (2) | C5D—C6D | 1.3896 (19) |
C5A—H5A | 0.9500 | C5D—H5D | 0.9500 |
C6A—C7A | 1.377 (2) | C6D—C7D | 1.384 (2) |
C6A—H6A | 0.9500 | C6D—H6D | 0.9500 |
C7A—C8A | 1.374 (2) | C7D—C8D | 1.379 (2) |
C7A—H7A | 0.9500 | C7D—H7D | 0.9500 |
C8A—C9A | 1.390 (2) | C8D—C9D | 1.3887 (19) |
C8A—H8A | 0.9500 | C8D—H8D | 0.9500 |
C9A—H9A | 0.9500 | C9D—H9D | 0.9500 |
N1B—C3B | 1.3380 (16) | N1E—C3E | 1.3409 (16) |
N1B—N2B | 1.3525 (16) | N1E—N2E | 1.3542 (15) |
N2B—C1B | 1.3393 (17) | N2E—C1E | 1.3390 (18) |
N2B—H2NB | 0.8800 | N2E—H2NE | 0.8800 |
C1B—C2B | 1.370 (2) | C1E—C2E | 1.3727 (18) |
C1B—H1B | 0.9500 | C1E—H1E | 0.9500 |
C2B—C3B | 1.4066 (18) | C2E—C3E | 1.4055 (18) |
C2B—H2B | 0.9500 | C2E—H2E | 0.9500 |
C3B—C4B | 1.4724 (18) | C3E—C4E | 1.4734 (17) |
C4B—C9B | 1.3967 (18) | C4E—C9E | 1.3921 (17) |
C4B—C5B | 1.3992 (17) | C4E—C5E | 1.3987 (18) |
C5B—C6B | 1.386 (2) | C5E—C6E | 1.3879 (19) |
C5B—H5B | 0.9500 | C5E—H5E | 0.9500 |
C6B—C7B | 1.386 (2) | C6E—C7E | 1.386 (2) |
C6B—H6B | 0.9500 | C6E—H6E | 0.9500 |
C7B—C8B | 1.383 (2) | C7E—C8E | 1.383 (2) |
C7B—H7B | 0.9500 | C7E—H7E | 0.9500 |
C8B—C9B | 1.385 (2) | C8E—C9E | 1.3916 (18) |
C8B—H8B | 0.9500 | C8E—H8E | 0.9500 |
C9B—H9B | 0.9500 | C9E—H9E | 0.9500 |
N1C—C3C | 1.3429 (15) | N1F—C3F | 1.3429 (16) |
N1C—N2C | 1.3526 (16) | N1F—N2F | 1.3514 (15) |
N2C—C1C | 1.3417 (18) | N2F—C1F | 1.3414 (17) |
N2C—H2NC | 0.8800 | N2F—H2NF | 0.8800 |
C1C—C2C | 1.3762 (18) | C1F—C2F | 1.371 (2) |
C1C—H1C | 0.9500 | C1F—H1F | 0.9500 |
C2C—C3C | 1.4082 (19) | C2F—C3F | 1.4091 (18) |
C2C—H2C | 0.9500 | C2F—H2F | 0.9500 |
C3C—C4C | 1.4727 (17) | C3F—C4F | 1.4680 (18) |
C4C—C5C | 1.3953 (19) | C4F—C9F | 1.3987 (18) |
C4C—C9C | 1.3975 (17) | C4F—C5F | 1.4007 (17) |
C5C—C6C | 1.3867 (19) | C5F—C6F | 1.3838 (19) |
C5C—H5C | 0.9500 | C5F—H5F | 0.9500 |
C6C—C7C | 1.388 (2) | C6F—C7F | 1.389 (2) |
C6C—H6C | 0.9500 | C6F—H6F | 0.9500 |
C7C—C8C | 1.382 (2) | C7F—C8F | 1.384 (2) |
C7C—H7C | 0.9500 | C7F—H7F | 0.9500 |
C8C—C9C | 1.3884 (19) | C8F—C9F | 1.390 (2) |
C8C—H8C | 0.9500 | C8F—H8F | 0.9500 |
C9C—H9C | 0.9500 | C9F—H9F | 0.9500 |
C3A—N1A—N2A | 104.79 (10) | C3D—N1D—N2D | 104.79 (10) |
C1A—N2A—N1A | 112.49 (11) | C1D—N2D—N1D | 112.41 (10) |
C1A—N2A—H2NA | 123.8 | C1D—N2D—H2ND | 123.8 |
N1A—N2A—H2NA | 123.8 | N1D—N2D—H2ND | 123.8 |
N2A—C1A—C2A | 106.74 (12) | N2D—C1D—C2D | 106.90 (12) |
N2A—C1A—H1A | 126.6 | N2D—C1D—H1D | 126.6 |
C2A—C1A—H1A | 126.6 | C2D—C1D—H1D | 126.6 |
C1A—C2A—C3A | 105.49 (11) | C1D—C2D—C3D | 105.24 (11) |
C1A—C2A—H2A | 127.3 | C1D—C2D—H2D | 127.4 |
C3A—C2A—H2A | 127.3 | C3D—C2D—H2D | 127.4 |
N1A—C3A—C2A | 110.49 (11) | N1D—C3D—C2D | 110.66 (11) |
N1A—C3A—C4A | 121.87 (11) | N1D—C3D—C4D | 121.32 (11) |
C2A—C3A—C4A | 127.64 (11) | C2D—C3D—C4D | 127.79 (11) |
C5A—C4A—C9A | 118.08 (12) | C5D—C4D—C9D | 118.71 (12) |
C5A—C4A—C3A | 122.31 (12) | C5D—C4D—C3D | 121.25 (11) |
C9A—C4A—C3A | 119.60 (11) | C9D—C4D—C3D | 119.86 (12) |
C6A—C5A—C4A | 120.57 (14) | C6D—C5D—C4D | 120.38 (13) |
C6A—C5A—H5A | 119.7 | C6D—C5D—H5D | 119.8 |
C4A—C5A—H5A | 119.7 | C4D—C5D—H5D | 119.8 |
C7A—C6A—C5A | 120.97 (15) | C7D—C6D—C5D | 120.49 (14) |
C7A—C6A—H6A | 119.5 | C7D—C6D—H6D | 119.8 |
C5A—C6A—H6A | 119.5 | C5D—C6D—H6D | 119.8 |
C8A—C7A—C6A | 119.00 (14) | C8D—C7D—C6D | 119.40 (13) |
C8A—C7A—H7A | 120.5 | C8D—C7D—H7D | 120.3 |
C6A—C7A—H7A | 120.5 | C6D—C7D—H7D | 120.3 |
C7A—C8A—C9A | 120.54 (14) | C7D—C8D—C9D | 120.67 (13) |
C7A—C8A—H8A | 119.7 | C7D—C8D—H8D | 119.7 |
C9A—C8A—H8A | 119.7 | C9D—C8D—H8D | 119.7 |
C8A—C9A—C4A | 120.82 (13) | C8D—C9D—C4D | 120.34 (13) |
C8A—C9A—H9A | 119.6 | C8D—C9D—H9D | 119.8 |
C4A—C9A—H9A | 119.6 | C4D—C9D—H9D | 119.8 |
C3B—N1B—N2B | 105.21 (10) | C3E—N1E—N2E | 105.08 (10) |
C1B—N2B—N1B | 112.05 (11) | C1E—N2E—N1E | 111.98 (10) |
C1B—N2B—H2NB | 124.0 | C1E—N2E—H2NE | 124.0 |
N1B—N2B—H2NB | 124.0 | N1E—N2E—H2NE | 124.0 |
N2B—C1B—C2B | 107.18 (12) | N2E—C1E—C2E | 107.39 (12) |
N2B—C1B—H1B | 126.4 | N2E—C1E—H1E | 126.3 |
C2B—C1B—H1B | 126.4 | C2E—C1E—H1E | 126.3 |
C1B—C2B—C3B | 105.29 (12) | C1E—C2E—C3E | 105.05 (12) |
C1B—C2B—H2B | 127.4 | C1E—C2E—H2E | 127.5 |
C3B—C2B—H2B | 127.4 | C3E—C2E—H2E | 127.5 |
N1B—C3B—C2B | 110.27 (12) | N1E—C3E—C2E | 110.50 (11) |
N1B—C3B—C4B | 120.95 (11) | N1E—C3E—C4E | 120.46 (11) |
C2B—C3B—C4B | 128.77 (12) | C2E—C3E—C4E | 129.00 (11) |
C9B—C4B—C5B | 118.16 (12) | C9E—C4E—C5E | 118.34 (12) |
C9B—C4B—C3B | 120.34 (11) | C9E—C4E—C3E | 120.31 (12) |
C5B—C4B—C3B | 121.50 (11) | C5E—C4E—C3E | 121.33 (11) |
C6B—C5B—C4B | 120.67 (13) | C6E—C5E—C4E | 120.83 (12) |
C6B—C5B—H5B | 119.7 | C6E—C5E—H5E | 119.6 |
C4B—C5B—H5B | 119.7 | C4E—C5E—H5E | 119.6 |
C5B—C6B—C7B | 120.48 (13) | C7E—C6E—C5E | 120.20 (13) |
C5B—C6B—H6B | 119.8 | C7E—C6E—H6E | 119.9 |
C7B—C6B—H6B | 119.8 | C5E—C6E—H6E | 119.9 |
C8B—C7B—C6B | 119.35 (13) | C8E—C7E—C6E | 119.53 (13) |
C8B—C7B—H7B | 120.3 | C8E—C7E—H7E | 120.2 |
C6B—C7B—H7B | 120.3 | C6E—C7E—H7E | 120.2 |
C7B—C8B—C9B | 120.49 (13) | C7E—C8E—C9E | 120.42 (13) |
C7B—C8B—H8B | 119.8 | C7E—C8E—H8E | 119.8 |
C9B—C8B—H8B | 119.8 | C9E—C8E—H8E | 119.8 |
C8B—C9B—C4B | 120.84 (12) | C8E—C9E—C4E | 120.67 (13) |
C8B—C9B—H9B | 119.6 | C8E—C9E—H9E | 119.7 |
C4B—C9B—H9B | 119.6 | C4E—C9E—H9E | 119.7 |
C3C—N1C—N2C | 105.03 (10) | C3F—N1F—N2F | 104.84 (10) |
C1C—N2C—N1C | 112.30 (10) | C1F—N2F—N1F | 112.44 (11) |
C1C—N2C—H2NC | 123.9 | C1F—N2F—H2NF | 123.8 |
N1C—N2C—H2NC | 123.9 | N1F—N2F—H2NF | 123.8 |
N2C—C1C—C2C | 107.09 (12) | N2F—C1F—C2F | 107.10 (12) |
N2C—C1C—H1C | 126.5 | N2F—C1F—H1F | 126.5 |
C2C—C1C—H1C | 126.5 | C2F—C1F—H1F | 126.5 |
C1C—C2C—C3C | 105.11 (12) | C1F—C2F—C3F | 105.14 (12) |
C1C—C2C—H2C | 127.4 | C1F—C2F—H2F | 127.4 |
C3C—C2C—H2C | 127.4 | C3F—C2F—H2F | 127.4 |
N1C—C3C—C2C | 110.46 (11) | N1F—C3F—C2F | 110.48 (12) |
N1C—C3C—C4C | 121.06 (11) | N1F—C3F—C4F | 121.19 (11) |
C2C—C3C—C4C | 128.45 (11) | C2F—C3F—C4F | 128.32 (12) |
C5C—C4C—C9C | 118.33 (12) | C9F—C4F—C5F | 118.26 (12) |
C5C—C4C—C3C | 121.37 (11) | C9F—C4F—C3F | 120.61 (11) |
C9C—C4C—C3C | 120.30 (12) | C5F—C4F—C3F | 121.12 (11) |
C6C—C5C—C4C | 120.62 (12) | C6F—C5F—C4F | 120.42 (12) |
C6C—C5C—H5C | 119.7 | C6F—C5F—H5F | 119.8 |
C4C—C5C—H5C | 119.7 | C4F—C5F—H5F | 119.8 |
C5C—C6C—C7C | 120.59 (13) | C5F—C6F—C7F | 120.90 (13) |
C5C—C6C—H6C | 119.7 | C5F—C6F—H6F | 119.5 |
C7C—C6C—H6C | 119.7 | C7F—C6F—H6F | 119.5 |
C8C—C7C—C6C | 119.19 (13) | C8F—C7F—C6F | 119.24 (13) |
C8C—C7C—H7C | 120.4 | C8F—C7F—H7F | 120.4 |
C6C—C7C—H7C | 120.4 | C6F—C7F—H7F | 120.4 |
C7C—C8C—C9C | 120.59 (13) | C7F—C8F—C9F | 120.28 (13) |
C7C—C8C—H8C | 119.7 | C7F—C8F—H8F | 119.9 |
C9C—C8C—H8C | 119.7 | C9F—C8F—H8F | 119.9 |
C8C—C9C—C4C | 120.65 (13) | C8F—C9F—C4F | 120.89 (13) |
C8C—C9C—H9C | 119.7 | C8F—C9F—H9F | 119.6 |
C4C—C9C—H9C | 119.7 | C4F—C9F—H9F | 119.6 |
C3A—N1A—N2A—C1A | 0.06 (14) | C3D—N1D—N2D—C1D | 0.29 (14) |
N1A—N2A—C1A—C2A | −0.11 (16) | N1D—N2D—C1D—C2D | −0.75 (15) |
N2A—C1A—C2A—C3A | 0.10 (16) | N2D—C1D—C2D—C3D | 0.86 (15) |
N2A—N1A—C3A—C2A | 0.01 (14) | N2D—N1D—C3D—C2D | 0.28 (13) |
N2A—N1A—C3A—C4A | −179.98 (11) | N2D—N1D—C3D—C4D | −174.61 (10) |
C1A—C2A—C3A—N1A | −0.07 (16) | C1D—C2D—C3D—N1D | −0.72 (15) |
C1A—C2A—C3A—C4A | 179.92 (12) | C1D—C2D—C3D—C4D | 173.76 (12) |
N1A—C3A—C4A—C5A | 9.0 (2) | N1D—C3D—C4D—C5D | 25.81 (18) |
C2A—C3A—C4A—C5A | −170.94 (15) | C2D—C3D—C4D—C5D | −148.14 (13) |
N1A—C3A—C4A—C9A | −170.16 (13) | N1D—C3D—C4D—C9D | −159.16 (12) |
C2A—C3A—C4A—C9A | 9.9 (2) | C2D—C3D—C4D—C9D | 26.89 (19) |
C9A—C4A—C5A—C6A | 0.6 (3) | C9D—C4D—C5D—C6D | −0.8 (2) |
C3A—C4A—C5A—C6A | −178.58 (16) | C3D—C4D—C5D—C6D | 174.30 (12) |
C4A—C5A—C6A—C7A | −1.2 (3) | C4D—C5D—C6D—C7D | −0.5 (2) |
C5A—C6A—C7A—C8A | 0.5 (3) | C5D—C6D—C7D—C8D | 1.2 (2) |
C6A—C7A—C8A—C9A | 0.7 (3) | C6D—C7D—C8D—C9D | −0.6 (2) |
C7A—C8A—C9A—C4A | −1.3 (3) | C7D—C8D—C9D—C4D | −0.7 (2) |
C5A—C4A—C9A—C8A | 0.6 (2) | C5D—C4D—C9D—C8D | 1.37 (19) |
C3A—C4A—C9A—C8A | 179.80 (14) | C3D—C4D—C9D—C8D | −173.78 (12) |
C3B—N1B—N2B—C1B | 0.12 (15) | C3E—N1E—N2E—C1E | 0.34 (14) |
N1B—N2B—C1B—C2B | −0.19 (18) | N1E—N2E—C1E—C2E | −0.41 (16) |
N2B—C1B—C2B—C3B | 0.18 (18) | N2E—C1E—C2E—C3E | 0.30 (15) |
N2B—N1B—C3B—C2B | 0.00 (14) | N2E—N1E—C3E—C2E | −0.14 (13) |
N2B—N1B—C3B—C4B | −179.97 (11) | N2E—N1E—C3E—C4E | −177.97 (10) |
C1B—C2B—C3B—N1B | −0.11 (17) | C1E—C2E—C3E—N1E | −0.10 (15) |
C1B—C2B—C3B—C4B | 179.86 (13) | C1E—C2E—C3E—C4E | 177.49 (12) |
N1B—C3B—C4B—C9B | −172.27 (12) | N1E—C3E—C4E—C9E | −177.07 (11) |
C2B—C3B—C4B—C9B | 7.8 (2) | C2E—C3E—C4E—C9E | 5.55 (19) |
N1B—C3B—C4B—C5B | 8.26 (18) | N1E—C3E—C4E—C5E | 4.80 (17) |
C2B—C3B—C4B—C5B | −171.70 (14) | C2E—C3E—C4E—C5E | −172.58 (12) |
C9B—C4B—C5B—C6B | 0.10 (19) | C9E—C4E—C5E—C6E | −0.26 (18) |
C3B—C4B—C5B—C6B | 179.58 (12) | C3E—C4E—C5E—C6E | 177.90 (11) |
C4B—C5B—C6B—C7B | 0.1 (2) | C4E—C5E—C6E—C7E | −0.47 (19) |
C5B—C6B—C7B—C8B | −0.1 (2) | C5E—C6E—C7E—C8E | 0.5 (2) |
C6B—C7B—C8B—C9B | −0.1 (2) | C6E—C7E—C8E—C9E | 0.1 (2) |
C7B—C8B—C9B—C4B | 0.3 (2) | C7E—C8E—C9E—C4E | −0.9 (2) |
C5B—C4B—C9B—C8B | −0.32 (19) | C5E—C4E—C9E—C8E | 0.94 (18) |
C3B—C4B—C9B—C8B | −179.81 (12) | C3E—C4E—C9E—C8E | −177.24 (11) |
C3C—N1C—N2C—C1C | 0.32 (14) | C3F—N1F—N2F—C1F | −0.12 (14) |
N1C—N2C—C1C—C2C | −0.03 (16) | N1F—N2F—C1F—C2F | 0.12 (15) |
N2C—C1C—C2C—C3C | −0.26 (16) | N2F—C1F—C2F—C3F | −0.06 (15) |
N2C—N1C—C3C—C2C | −0.48 (14) | N2F—N1F—C3F—C2F | 0.08 (13) |
N2C—N1C—C3C—C4C | 177.87 (11) | N2F—N1F—C3F—C4F | 179.18 (10) |
C1C—C2C—C3C—N1C | 0.47 (15) | C1F—C2F—C3F—N1F | −0.01 (15) |
C1C—C2C—C3C—C4C | −177.72 (12) | C1F—C2F—C3F—C4F | −179.03 (12) |
N1C—C3C—C4C—C5C | −8.77 (18) | N1F—C3F—C4F—C9F | 159.25 (12) |
C2C—C3C—C4C—C5C | 169.26 (13) | C2F—C3F—C4F—C9F | −21.82 (19) |
N1C—C3C—C4C—C9C | 171.53 (12) | N1F—C3F—C4F—C5F | −21.07 (17) |
C2C—C3C—C4C—C9C | −10.4 (2) | C2F—C3F—C4F—C5F | 157.85 (13) |
C9C—C4C—C5C—C6C | −1.63 (19) | C9F—C4F—C5F—C6F | −0.78 (18) |
C3C—C4C—C5C—C6C | 178.67 (12) | C3F—C4F—C5F—C6F | 179.54 (11) |
C4C—C5C—C6C—C7C | 0.8 (2) | C4F—C5F—C6F—C7F | 0.81 (19) |
C5C—C6C—C7C—C8C | 0.6 (2) | C5F—C6F—C7F—C8F | −0.5 (2) |
C6C—C7C—C8C—C9C | −1.0 (2) | C6F—C7F—C8F—C9F | 0.2 (2) |
C7C—C8C—C9C—C4C | 0.1 (2) | C7F—C8F—C9F—C4F | −0.2 (2) |
C5C—C4C—C9C—C8C | 1.19 (19) | C5F—C4F—C9F—C8F | 0.46 (19) |
C3C—C4C—C9C—C8C | −179.10 (12) | C3F—C4F—C9F—C8F | −179.85 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2NA···N1B | 0.88 | 2.06 | 2.8905 (17) | 158 |
N2B—H2NB···N1C | 0.88 | 2.12 | 2.9601 (16) | 159 |
N2C—H2NC···N1Ai | 0.88 | 2.12 | 2.9540 (18) | 157 |
N2D—H2ND···N1E | 0.88 | 2.06 | 2.8767 (18) | 154 |
N2E—H2NE···N1F | 0.88 | 2.12 | 2.9587 (15) | 159 |
N2F—H2NF···N1Dii | 0.88 | 2.11 | 2.9157 (15) | 152 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C9H8N2 |
Mr | 144.17 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 148 |
a, b, c (Å) | 12.1514 (10), 12.3120 (11), 17.114 (2) |
α, β, γ (°) | 88.164 (11), 88.103 (12), 62.816 (6) |
V (Å3) | 2275.9 (4) |
Z | 12 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.50 × 0.48 × 0.40 |
Data collection | |
Diffractometer | Siemens SMART CCD diffractometer |
Absorption correction | Numerical (SHELXTL; Sheldrick, 1996) |
Tmin, Tmax | 0.959, 0.975 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 40438, 14026, 10303 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.725 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.124, 1.05 |
No. of reflections | 14026 |
No. of parameters | 596 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.27 |
Computer programs: SMART (Siemens, 1995), SMART, SAINT (Siemens, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP in SHELXTL (Sheldrick, 1996), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2NA···N1B | 0.88 | 2.06 | 2.8905 (17) | 158 |
N2B—H2NB···N1C | 0.88 | 2.12 | 2.9601 (16) | 159 |
N2C—H2NC···N1Ai | 0.88 | 2.12 | 2.9540 (18) | 157 |
N2D—H2ND···N1E | 0.88 | 2.06 | 2.8767 (18) | 154 |
N2E—H2NE···N1F | 0.88 | 2.12 | 2.9587 (15) | 159 |
N2F—H2NF···N1Dii | 0.88 | 2.11 | 2.9157 (15) | 152 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z. |
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Tris(1-pyrazolyl)borates (scorpionates) were invented more than 30 years ago and are today well established as ligands in coordination chemistry (Trofimenko, 1993). Scorpionates now find wide-ranging applications in chemistry, from modelling the active site of metal enzymes, through analytical chemistry and organic chemistry to catalysis and material science (Edelmann, 2001). Given this background, we became interested in the synthesis of transition metal complexes of hydrotri(3-phenylpyrazol-1-yl)borate. Therefore, we prepared 3-phenylpyrazole, (I). The synthesis of (I) was confirmed by a crystal structure determination.
The structure of (I) contains six independent molecules, labeled A to F (Fig. 1). The dimensions of the six molecules are very similar. The pyrazole and phenyl groups of each molecule are approximately planar. The angles between the planes of the pyrazole and phenyl groups are 9.21 (11), 8.10 (5), 9.38 (6), 27.62 (7), 6.21 (4) and 21.33 (4)° for molecules A–F, respectively. The crystal structure contains two independent clusters of six molecules connected by N—H.·N hydrogen bonds (Table 1). The six-membered clusters are centrosymmetric. One hexamer contains molecules A, B and C, while the other contains molecules D, E and F. Both hexamers have rather similar conformations (Fig. 2). Each is additionally stabilized by two symmetry-related Cpyrazole—H···πpyrazole and Cpyrazole—H···πphenyl interactions, with H···π distances between 2.64 and 2.83 Å, and C—H···π angles between 138 and 152° (π represents the centroid of the corresponding pyrazole or phenyl ring). Different hexamers are connected by seven additional intermolecular C—-H···πpyrazole or C–H···πphenyl interactions, with H···π distances between 2.76 and 3.14 Å, and C—H···π angles between 123 and 170°. One interaction is found between each of the symmetry-related hexamers, while five interactions connect symmetry-independent hexamers. The hexamer containing molecules A, B and C mainly occupies the section of the unit cell defined by 1/4 < z < 3/4 (Fig. 3). The hexamer containing molecules D, E and F is mainly confined to the section of the unit cell defined by −1/4 < z < 1/4. The crystal packing in both sections of the unit cell is very similar. The arrangement of the molecules in the latter section can approximately be obtained from the structure of the first section by interchanging the a and b axes. This shows the crystal structure of the title compound to be pseudosymmetric. The coordinates of the atoms in the two independent hexamers are related by the pseudosymmetry relations: xABC ~0.5 − yDEF, yABC ~1 − xDEF, zABC ~0.5 − zDEF and xABC ~0.5 + yDiEiFi, yABC ~xDiEiFi, zABC ~0.5 + zDiEiFi [symmetry code: (i) 1 − x, −y, −z]. The latter pseudosymmetry relation corresponds to an approximate c-glide plane perpendicular to the a,¯b diagonal. A crystal structure with similar pseudosymmetric domains connected by C—H···π interactions has been reported by Bats et al. (1999).