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Molecules of the title compound, C
24H
21BrN
2, are linked into chains by a single C—H
π(arene) hydrogen bond, but C—H
N hydrogen bonds and aromatic π–π stacking interactions are absent.
Supporting information
CCDC reference: 236058
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.003 Å
- R factor = 0.033
- wR factor = 0.078
- Data-to-parameter ratio = 18.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H18A .. CG1 = 2.81 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H56 .. CG2 = 3.08 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 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
0 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
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: OSCAIL (McArdle, 1995, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).
5-(4-Bromophenyl)-3-phenyl-1-(3-phenylpropyl)-1
H-pyrazole
top
Crystal data top
C24H21BrN2 | F(000) = 1712 |
Mr = 417.34 | Dx = 1.442 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 4410 reflections |
a = 5.6755 (1) Å | θ = 3.1–27.5° |
b = 25.5102 (5) Å | µ = 2.15 mm−1 |
c = 26.5536 (5) Å | T = 120 K |
V = 3844.51 (12) Å3 | Block, colourless |
Z = 8 | 0.50 × 0.20 × 0.16 mm |
Data collection top
Nonius KappaCCD diffractometer | 4410 independent reflections |
Radiation source: rotating anode | 3338 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.070 |
φ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997) | h = −7→6 |
Tmin = 0.575, Tmax = 0.712 | k = −32→33 |
28955 measured reflections | l = −34→34 |
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: inferred from neighbouring sites |
wR(F2) = 0.078 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0307P)2 + 2.0921P] where P = (Fo2 + 2Fc2)/3 |
4410 reflections | (Δ/σ)max = 0.001 |
244 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.49 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Br54 | −0.13999 (4) | 0.337207 (8) | 0.702739 (8) | 0.02660 (8) | |
N1 | 0.6629 (3) | 0.51900 (6) | 0.60374 (7) | 0.0216 (4) | |
N2 | 0.8049 (3) | 0.56145 (7) | 0.60241 (7) | 0.0225 (4) | |
C3 | 0.7623 (4) | 0.58716 (8) | 0.64529 (8) | 0.0222 (4) | |
C4 | 0.5905 (4) | 0.56114 (8) | 0.67397 (8) | 0.0228 (5) | |
C5 | 0.5298 (4) | 0.51705 (8) | 0.64649 (8) | 0.0210 (4) | |
C11 | 0.7251 (4) | 0.37003 (8) | 0.51946 (8) | 0.0247 (5) | |
C12 | 0.5307 (4) | 0.36288 (9) | 0.48856 (9) | 0.0314 (5) | |
C13 | 0.3790 (4) | 0.32069 (10) | 0.49563 (10) | 0.0358 (6) | |
C14 | 0.4193 (4) | 0.28552 (9) | 0.53395 (10) | 0.0352 (6) | |
C15 | 0.6123 (4) | 0.29194 (9) | 0.56524 (9) | 0.0314 (5) | |
C16 | 0.7649 (4) | 0.33390 (9) | 0.55768 (9) | 0.0282 (5) | |
C17 | 0.6675 (4) | 0.48501 (8) | 0.55968 (8) | 0.0227 (5) | |
C18 | 0.8949 (4) | 0.45386 (8) | 0.55618 (8) | 0.0248 (5) | |
C19 | 0.8915 (4) | 0.41538 (9) | 0.51183 (9) | 0.0305 (5) | |
C31 | 0.8977 (4) | 0.63511 (8) | 0.65623 (8) | 0.0225 (5) | |
C32 | 1.0997 (4) | 0.64644 (9) | 0.62883 (9) | 0.0308 (5) | |
C33 | 1.2296 (5) | 0.69105 (9) | 0.63900 (10) | 0.0348 (6) | |
C34 | 1.1596 (4) | 0.72499 (9) | 0.67618 (10) | 0.0341 (6) | |
C35 | 0.9604 (5) | 0.71422 (9) | 0.70361 (9) | 0.0321 (5) | |
C36 | 0.8277 (4) | 0.66941 (8) | 0.69419 (9) | 0.0285 (5) | |
C51 | 0.3680 (4) | 0.47405 (8) | 0.65914 (8) | 0.0201 (4) | |
C52 | 0.4219 (4) | 0.42201 (8) | 0.64725 (8) | 0.0235 (5) | |
C53 | 0.2701 (4) | 0.38190 (8) | 0.65987 (8) | 0.0236 (5) | |
C54 | 0.0659 (4) | 0.39304 (8) | 0.68557 (8) | 0.0222 (5) | |
C55 | 0.0084 (4) | 0.44406 (9) | 0.69871 (8) | 0.0240 (5) | |
C56 | 0.1588 (4) | 0.48412 (8) | 0.68483 (8) | 0.0227 (5) | |
H4 | 0.5287 | 0.5716 | 0.7057 | 0.027* | |
H12 | 0.5007 | 0.3871 | 0.4622 | 0.038* | |
H13 | 0.2473 | 0.3161 | 0.4740 | 0.043* | |
H14 | 0.3149 | 0.2569 | 0.5389 | 0.042* | |
H15 | 0.6405 | 0.2678 | 0.5918 | 0.038* | |
H16 | 0.8982 | 0.3379 | 0.5790 | 0.034* | |
H17A | 0.6494 | 0.5066 | 0.5289 | 0.027* | |
H17B | 0.5326 | 0.4605 | 0.5613 | 0.027* | |
H18A | 0.9188 | 0.4342 | 0.5879 | 0.030* | |
H18B | 1.0290 | 0.4783 | 0.5521 | 0.030* | |
H19A | 0.8453 | 0.4345 | 0.4809 | 0.037* | |
H19B | 1.0526 | 0.4015 | 0.5066 | 0.037* | |
H32 | 1.1491 | 0.6233 | 0.6028 | 0.037* | |
H33 | 1.3681 | 0.6982 | 0.6201 | 0.042* | |
H34 | 1.2485 | 0.7558 | 0.6829 | 0.041* | |
H35 | 0.9124 | 0.7377 | 0.7294 | 0.039* | |
H36 | 0.6905 | 0.6623 | 0.7135 | 0.034* | |
H52 | 0.5649 | 0.4142 | 0.6302 | 0.028* | |
H53 | 0.3064 | 0.3468 | 0.6509 | 0.028* | |
H55 | −0.1319 | 0.4513 | 0.7169 | 0.029* | |
H56 | 0.1187 | 0.5193 | 0.6930 | 0.027* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br54 | 0.01898 (12) | 0.02974 (13) | 0.03106 (13) | −0.00272 (9) | 0.00109 (9) | 0.00623 (10) |
N1 | 0.0244 (10) | 0.0184 (8) | 0.0221 (9) | −0.0008 (7) | 0.0003 (8) | −0.0016 (7) |
N2 | 0.0257 (10) | 0.0203 (9) | 0.0215 (9) | −0.0034 (7) | −0.0002 (8) | −0.0008 (7) |
C3 | 0.0242 (11) | 0.0193 (10) | 0.0232 (11) | 0.0038 (9) | −0.0016 (10) | −0.0013 (9) |
C4 | 0.0245 (12) | 0.0223 (11) | 0.0214 (11) | 0.0039 (9) | 0.0018 (9) | −0.0020 (9) |
C5 | 0.0179 (11) | 0.0227 (10) | 0.0224 (11) | 0.0037 (8) | −0.0001 (9) | 0.0012 (9) |
C11 | 0.0280 (12) | 0.0218 (11) | 0.0244 (11) | 0.0010 (9) | 0.0090 (10) | −0.0073 (9) |
C12 | 0.0370 (14) | 0.0255 (12) | 0.0318 (13) | 0.0045 (10) | 0.0033 (11) | −0.0027 (10) |
C13 | 0.0281 (13) | 0.0326 (13) | 0.0469 (16) | 0.0025 (11) | −0.0043 (12) | −0.0112 (12) |
C14 | 0.0331 (14) | 0.0244 (12) | 0.0480 (16) | −0.0032 (10) | 0.0097 (12) | −0.0060 (11) |
C15 | 0.0406 (15) | 0.0232 (11) | 0.0304 (12) | −0.0007 (10) | 0.0080 (11) | −0.0005 (10) |
C16 | 0.0294 (12) | 0.0287 (12) | 0.0265 (12) | 0.0003 (10) | 0.0037 (10) | −0.0064 (10) |
C17 | 0.0266 (12) | 0.0234 (10) | 0.0179 (10) | −0.0032 (9) | −0.0005 (9) | −0.0024 (9) |
C18 | 0.0251 (12) | 0.0240 (11) | 0.0251 (11) | −0.0029 (9) | 0.0048 (10) | −0.0027 (9) |
C19 | 0.0366 (14) | 0.0267 (12) | 0.0280 (12) | −0.0029 (10) | 0.0127 (11) | −0.0061 (10) |
C31 | 0.0255 (12) | 0.0191 (10) | 0.0227 (11) | 0.0015 (9) | −0.0034 (9) | 0.0019 (9) |
C32 | 0.0324 (13) | 0.0283 (12) | 0.0316 (13) | −0.0023 (10) | 0.0017 (11) | −0.0018 (10) |
C33 | 0.0343 (14) | 0.0303 (13) | 0.0398 (15) | −0.0061 (11) | −0.0063 (12) | 0.0049 (11) |
C34 | 0.0437 (15) | 0.0213 (11) | 0.0373 (14) | −0.0075 (10) | −0.0154 (12) | 0.0065 (10) |
C35 | 0.0428 (15) | 0.0224 (11) | 0.0311 (13) | 0.0011 (10) | −0.0078 (12) | −0.0040 (10) |
C36 | 0.0330 (13) | 0.0231 (11) | 0.0293 (13) | 0.0019 (9) | −0.0019 (10) | −0.0021 (9) |
C51 | 0.0184 (10) | 0.0217 (10) | 0.0203 (10) | 0.0015 (8) | −0.0029 (9) | 0.0023 (8) |
C52 | 0.0169 (11) | 0.0260 (11) | 0.0276 (11) | 0.0046 (8) | 0.0033 (9) | 0.0005 (9) |
C53 | 0.0198 (11) | 0.0223 (11) | 0.0287 (12) | 0.0021 (9) | 0.0019 (9) | 0.0011 (9) |
C54 | 0.0181 (10) | 0.0247 (11) | 0.0237 (11) | −0.0008 (8) | −0.0021 (9) | 0.0040 (9) |
C55 | 0.0178 (11) | 0.0338 (12) | 0.0204 (11) | 0.0043 (9) | 0.0016 (9) | 0.0000 (10) |
C56 | 0.0226 (11) | 0.0246 (11) | 0.0210 (10) | 0.0054 (9) | −0.0019 (9) | −0.0026 (9) |
Geometric parameters (Å, º) top
N1—N2 | 1.350 (2) | C3—C31 | 1.473 (3) |
N2—C3 | 1.336 (3) | C31—C32 | 1.388 (3) |
C3—C4 | 1.404 (3) | C31—C36 | 1.393 (3) |
C4—C5 | 1.384 (3) | C32—C33 | 1.383 (3) |
C5—N1 | 1.365 (3) | C32—H32 | 0.95 |
N1—C17 | 1.457 (3) | C33—C34 | 1.372 (4) |
C17—C18 | 1.519 (3) | C33—H33 | 0.95 |
C17—H17A | 0.99 | C34—C35 | 1.373 (4) |
C17—H17B | 0.99 | C34—H34 | 0.95 |
C18—C19 | 1.533 (3) | C35—C36 | 1.392 (3) |
C18—H18A | 0.99 | C35—H35 | 0.95 |
C18—H18B | 0.99 | C36—H36 | 0.95 |
C19—C11 | 1.507 (3) | C4—H4 | 0.95 |
C19—H19A | 0.99 | C5—C51 | 1.469 (3) |
C19—H19B | 0.99 | C51—C56 | 1.393 (3) |
C11—C12 | 1.387 (3) | C51—C52 | 1.398 (3) |
C11—C16 | 1.389 (3) | C52—C53 | 1.379 (3) |
C12—C13 | 1.391 (3) | C52—H52 | 0.95 |
C12—H12 | 0.95 | C53—C54 | 1.375 (3) |
C13—C14 | 1.376 (4) | C53—H53 | 0.95 |
C13—H13 | 0.95 | C54—C55 | 1.386 (3) |
C14—C15 | 1.385 (3) | C54—Br54 | 1.898 (2) |
C14—H14 | 0.95 | C55—C56 | 1.382 (3) |
C15—C16 | 1.391 (3) | C55—H55 | 0.95 |
C15—H15 | 0.95 | C56—H56 | 0.95 |
C16—H16 | 0.95 | | |
| | | |
C5—N1—N2 | 112.43 (17) | C32—C31—C3 | 120.0 (2) |
N2—N1—C17 | 116.49 (17) | C36—C31—C3 | 121.0 (2) |
C5—N1—C17 | 131.01 (18) | C33—C32—C31 | 120.6 (2) |
N1—C17—C18 | 112.06 (17) | C33—C32—H32 | 119.7 |
N1—C17—H17A | 109.2 | C31—C32—H32 | 119.7 |
C18—C17—H17A | 109.2 | C34—C33—C32 | 120.4 (2) |
N1—C17—H17B | 109.2 | C34—C33—H33 | 119.8 |
C18—C17—H17B | 109.2 | C32—C33—H33 | 119.8 |
H17A—C17—H17B | 107.9 | C33—C34—C35 | 119.6 (2) |
C17—C18—C19 | 111.79 (19) | C33—C34—H34 | 120.2 |
C17—C18—H18A | 109.3 | C35—C34—H34 | 120.2 |
C19—C18—H18A | 109.3 | C34—C35—C36 | 121.0 (2) |
C17—C18—H18B | 109.3 | C34—C35—H35 | 119.5 |
C19—C18—H18B | 109.3 | C36—C35—H35 | 119.5 |
H18A—C18—H18B | 107.9 | C35—C36—C31 | 119.5 (2) |
C11—C19—C18 | 113.34 (18) | C35—C36—H36 | 120.3 |
C11—C19—H19A | 108.9 | C31—C36—H36 | 120.3 |
C18—C19—H19A | 108.9 | C5—C4—H4 | 127.1 |
C11—C19—H19B | 108.9 | C3—C4—H4 | 127.1 |
C18—C19—H19B | 108.9 | C4—C5—N1 | 105.72 (18) |
H19A—C19—H19B | 107.7 | N1—C5—C51 | 124.28 (18) |
C12—C11—C16 | 118.3 (2) | C4—C5—C51 | 129.9 (2) |
C12—C11—C19 | 121.3 (2) | N1—N2—C3 | 105.28 (17) |
C16—C11—C19 | 120.4 (2) | C3—C4—C5 | 105.73 (19) |
C11—C12—C13 | 120.9 (2) | C56—C51—C52 | 118.17 (19) |
C11—C12—H12 | 119.5 | C56—C51—C5 | 120.43 (18) |
C13—C12—H12 | 119.5 | C52—C51—C5 | 121.37 (19) |
C14—C13—C12 | 120.1 (2) | C53—C52—C51 | 120.9 (2) |
C14—C13—H13 | 119.9 | C53—C52—H52 | 119.6 |
C12—C13—H13 | 119.9 | C51—C52—H52 | 119.6 |
C13—C14—C15 | 119.9 (2) | C54—C53—C52 | 119.6 (2) |
C13—C14—H14 | 120.1 | C54—C53—H53 | 120.2 |
C15—C14—H14 | 120.1 | C52—C53—H53 | 120.2 |
C14—C15—C16 | 119.8 (2) | C53—C54—C55 | 121.2 (2) |
C14—C15—H15 | 120.1 | C53—C54—Br54 | 118.89 (16) |
C16—C15—H15 | 120.1 | C55—C54—Br54 | 119.94 (16) |
C11—C16—C15 | 121.0 (2) | C56—C55—C54 | 118.8 (2) |
C11—C16—H16 | 119.5 | C56—C55—H55 | 120.6 |
C15—C16—H16 | 119.5 | C54—C55—H55 | 120.6 |
N2—C3—C4 | 110.84 (18) | C55—C56—C51 | 121.4 (2) |
N2—C3—C31 | 118.76 (19) | C55—C56—H56 | 119.3 |
C4—C3—C31 | 130.38 (19) | C51—C56—H56 | 119.3 |
C32—C31—C36 | 119.0 (2) | | |
| | | |
N2—N1—C17—C18 | 72.0 (2) | C33—C34—C35—C36 | −0.2 (4) |
C5—N1—C17—C18 | −111.5 (2) | C34—C35—C36—C31 | −0.3 (3) |
N1—C17—C18—C19 | 176.02 (17) | C32—C31—C36—C35 | 0.4 (3) |
C17—C18—C19—C11 | −70.4 (3) | C3—C31—C36—C35 | 179.7 (2) |
C18—C19—C11—C12 | 115.9 (2) | N2—C3—C4—C5 | 0.6 (2) |
C18—C19—C11—C16 | −64.7 (3) | C31—C3—C4—C5 | −177.5 (2) |
C16—C11—C12—C13 | 0.1 (3) | N2—N1—C5—C4 | 0.2 (2) |
C19—C11—C12—C13 | 179.5 (2) | C17—N1—C5—C4 | −176.5 (2) |
C11—C12—C13—C14 | 0.6 (4) | N2—N1—C5—C51 | −176.99 (18) |
C12—C13—C14—C15 | −0.5 (4) | C17—N1—C5—C51 | 6.4 (3) |
C13—C14—C15—C16 | −0.1 (3) | C3—C4—C5—N1 | −0.5 (2) |
C12—C11—C16—C15 | −0.8 (3) | C3—C4—C5—C51 | 176.5 (2) |
C19—C11—C16—C15 | 179.8 (2) | N1—C5—C51—C56 | −145.5 (2) |
C14—C15—C16—C11 | 0.8 (3) | C4—C5—C51—C56 | 38.0 (3) |
C5—N1—N2—C3 | 0.2 (2) | N1—C5—C51—C52 | 36.4 (3) |
C17—N1—N2—C3 | 177.37 (17) | C4—C5—C51—C52 | −140.0 (2) |
N1—N2—C3—C4 | −0.5 (2) | C56—C51—C52—C53 | 1.1 (3) |
N1—N2—C3—C31 | 177.88 (18) | C5—C51—C52—C53 | 179.2 (2) |
N2—C3—C31—C32 | −14.6 (3) | C51—C52—C53—C54 | −1.6 (3) |
C4—C3—C31—C32 | 163.4 (2) | C52—C53—C54—C55 | 0.6 (3) |
N2—C3—C31—C36 | 166.0 (2) | C52—C53—C54—Br54 | −179.81 (16) |
C4—C3—C31—C36 | −16.0 (3) | C53—C54—C55—C56 | 1.0 (3) |
C36—C31—C32—C33 | 0.0 (3) | Br54—C54—C55—C56 | −178.64 (16) |
C3—C31—C32—C33 | −179.4 (2) | C54—C55—C56—C51 | −1.5 (3) |
C31—C32—C33—C34 | −0.4 (4) | C52—C51—C56—C55 | 0.5 (3) |
C32—C33—C34—C35 | 0.5 (4) | C5—C51—C56—C55 | −177.60 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18A···Cg1i | 0.99 | 2.81 | 3.625 (2) | 140 |
C56—H56···Cg2ii | 0.95 | 3.08 | 3.499 (2) | 108 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z. |
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