Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
Molecules of the title compound, C24H21BrN2, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804001874/lh6163sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804001874/lh6163Isup2.hkl
Contains datablock I

CCDC reference: 236058

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](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

Computing details top

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)-1H-pyrazole top
Crystal data top
C24H21BrN2F(000) = 1712
Mr = 417.34Dx = 1.442 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 4410 reflections
a = 5.6755 (1) Åθ = 3.1–27.5°
b = 25.5102 (5) ŵ = 2.15 mm1
c = 26.5536 (5) ÅT = 120 K
V = 3844.51 (12) Å3Block, colourless
Z = 80.50 × 0.20 × 0.16 mm
Data collection top
Nonius KappaCCD
diffractometer
4410 independent reflections
Radiation source: rotating anode3338 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.070
φ scans, and ω scans with κ offsetsθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
(SORTAV; Blessing, 1995, 1997)
h = 76
Tmin = 0.575, Tmax = 0.712k = 3233
28955 measured reflectionsl = 3434
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078H-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 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = 0.49 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br540.13999 (4)0.337207 (8)0.702739 (8)0.02660 (8)
N10.6629 (3)0.51900 (6)0.60374 (7)0.0216 (4)
N20.8049 (3)0.56145 (7)0.60241 (7)0.0225 (4)
C30.7623 (4)0.58716 (8)0.64529 (8)0.0222 (4)
C40.5905 (4)0.56114 (8)0.67397 (8)0.0228 (5)
C50.5298 (4)0.51705 (8)0.64649 (8)0.0210 (4)
C110.7251 (4)0.37003 (8)0.51946 (8)0.0247 (5)
C120.5307 (4)0.36288 (9)0.48856 (9)0.0314 (5)
C130.3790 (4)0.32069 (10)0.49563 (10)0.0358 (6)
C140.4193 (4)0.28552 (9)0.53395 (10)0.0352 (6)
C150.6123 (4)0.29194 (9)0.56524 (9)0.0314 (5)
C160.7649 (4)0.33390 (9)0.55768 (9)0.0282 (5)
C170.6675 (4)0.48501 (8)0.55968 (8)0.0227 (5)
C180.8949 (4)0.45386 (8)0.55618 (8)0.0248 (5)
C190.8915 (4)0.41538 (9)0.51183 (9)0.0305 (5)
C310.8977 (4)0.63511 (8)0.65623 (8)0.0225 (5)
C321.0997 (4)0.64644 (9)0.62883 (9)0.0308 (5)
C331.2296 (5)0.69105 (9)0.63900 (10)0.0348 (6)
C341.1596 (4)0.72499 (9)0.67618 (10)0.0341 (6)
C350.9604 (5)0.71422 (9)0.70361 (9)0.0321 (5)
C360.8277 (4)0.66941 (8)0.69419 (9)0.0285 (5)
C510.3680 (4)0.47405 (8)0.65914 (8)0.0201 (4)
C520.4219 (4)0.42201 (8)0.64725 (8)0.0235 (5)
C530.2701 (4)0.38190 (8)0.65987 (8)0.0236 (5)
C540.0659 (4)0.39304 (8)0.68557 (8)0.0222 (5)
C550.0084 (4)0.44406 (9)0.69871 (8)0.0240 (5)
C560.1588 (4)0.48412 (8)0.68483 (8)0.0227 (5)
H40.52870.57160.70570.027*
H120.50070.38710.46220.038*
H130.24730.31610.47400.043*
H140.31490.25690.53890.042*
H150.64050.26780.59180.038*
H160.89820.33790.57900.034*
H17A0.64940.50660.52890.027*
H17B0.53260.46050.56130.027*
H18A0.91880.43420.58790.030*
H18B1.02900.47830.55210.030*
H19A0.84530.43450.48090.037*
H19B1.05260.40150.50660.037*
H321.14910.62330.60280.037*
H331.36810.69820.62010.042*
H341.24850.75580.68290.041*
H350.91240.73770.72940.039*
H360.69050.66230.71350.034*
H520.56490.41420.63020.028*
H530.30640.34680.65090.028*
H550.13190.45130.71690.029*
H560.11870.51930.69300.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br540.01898 (12)0.02974 (13)0.03106 (13)0.00272 (9)0.00109 (9)0.00623 (10)
N10.0244 (10)0.0184 (8)0.0221 (9)0.0008 (7)0.0003 (8)0.0016 (7)
N20.0257 (10)0.0203 (9)0.0215 (9)0.0034 (7)0.0002 (8)0.0008 (7)
C30.0242 (11)0.0193 (10)0.0232 (11)0.0038 (9)0.0016 (10)0.0013 (9)
C40.0245 (12)0.0223 (11)0.0214 (11)0.0039 (9)0.0018 (9)0.0020 (9)
C50.0179 (11)0.0227 (10)0.0224 (11)0.0037 (8)0.0001 (9)0.0012 (9)
C110.0280 (12)0.0218 (11)0.0244 (11)0.0010 (9)0.0090 (10)0.0073 (9)
C120.0370 (14)0.0255 (12)0.0318 (13)0.0045 (10)0.0033 (11)0.0027 (10)
C130.0281 (13)0.0326 (13)0.0469 (16)0.0025 (11)0.0043 (12)0.0112 (12)
C140.0331 (14)0.0244 (12)0.0480 (16)0.0032 (10)0.0097 (12)0.0060 (11)
C150.0406 (15)0.0232 (11)0.0304 (12)0.0007 (10)0.0080 (11)0.0005 (10)
C160.0294 (12)0.0287 (12)0.0265 (12)0.0003 (10)0.0037 (10)0.0064 (10)
C170.0266 (12)0.0234 (10)0.0179 (10)0.0032 (9)0.0005 (9)0.0024 (9)
C180.0251 (12)0.0240 (11)0.0251 (11)0.0029 (9)0.0048 (10)0.0027 (9)
C190.0366 (14)0.0267 (12)0.0280 (12)0.0029 (10)0.0127 (11)0.0061 (10)
C310.0255 (12)0.0191 (10)0.0227 (11)0.0015 (9)0.0034 (9)0.0019 (9)
C320.0324 (13)0.0283 (12)0.0316 (13)0.0023 (10)0.0017 (11)0.0018 (10)
C330.0343 (14)0.0303 (13)0.0398 (15)0.0061 (11)0.0063 (12)0.0049 (11)
C340.0437 (15)0.0213 (11)0.0373 (14)0.0075 (10)0.0154 (12)0.0065 (10)
C350.0428 (15)0.0224 (11)0.0311 (13)0.0011 (10)0.0078 (12)0.0040 (10)
C360.0330 (13)0.0231 (11)0.0293 (13)0.0019 (9)0.0019 (10)0.0021 (9)
C510.0184 (10)0.0217 (10)0.0203 (10)0.0015 (8)0.0029 (9)0.0023 (8)
C520.0169 (11)0.0260 (11)0.0276 (11)0.0046 (8)0.0033 (9)0.0005 (9)
C530.0198 (11)0.0223 (11)0.0287 (12)0.0021 (9)0.0019 (9)0.0011 (9)
C540.0181 (10)0.0247 (11)0.0237 (11)0.0008 (8)0.0021 (9)0.0040 (9)
C550.0178 (11)0.0338 (12)0.0204 (11)0.0043 (9)0.0016 (9)0.0000 (10)
C560.0226 (11)0.0246 (11)0.0210 (10)0.0054 (9)0.0019 (9)0.0026 (9)
Geometric parameters (Å, º) top
N1—N21.350 (2)C3—C311.473 (3)
N2—C31.336 (3)C31—C321.388 (3)
C3—C41.404 (3)C31—C361.393 (3)
C4—C51.384 (3)C32—C331.383 (3)
C5—N11.365 (3)C32—H320.95
N1—C171.457 (3)C33—C341.372 (4)
C17—C181.519 (3)C33—H330.95
C17—H17A0.99C34—C351.373 (4)
C17—H17B0.99C34—H340.95
C18—C191.533 (3)C35—C361.392 (3)
C18—H18A0.99C35—H350.95
C18—H18B0.99C36—H360.95
C19—C111.507 (3)C4—H40.95
C19—H19A0.99C5—C511.469 (3)
C19—H19B0.99C51—C561.393 (3)
C11—C121.387 (3)C51—C521.398 (3)
C11—C161.389 (3)C52—C531.379 (3)
C12—C131.391 (3)C52—H520.95
C12—H120.95C53—C541.375 (3)
C13—C141.376 (4)C53—H530.95
C13—H130.95C54—C551.386 (3)
C14—C151.385 (3)C54—Br541.898 (2)
C14—H140.95C55—C561.382 (3)
C15—C161.391 (3)C55—H550.95
C15—H150.95C56—H560.95
C16—H160.95
C5—N1—N2112.43 (17)C32—C31—C3120.0 (2)
N2—N1—C17116.49 (17)C36—C31—C3121.0 (2)
C5—N1—C17131.01 (18)C33—C32—C31120.6 (2)
N1—C17—C18112.06 (17)C33—C32—H32119.7
N1—C17—H17A109.2C31—C32—H32119.7
C18—C17—H17A109.2C34—C33—C32120.4 (2)
N1—C17—H17B109.2C34—C33—H33119.8
C18—C17—H17B109.2C32—C33—H33119.8
H17A—C17—H17B107.9C33—C34—C35119.6 (2)
C17—C18—C19111.79 (19)C33—C34—H34120.2
C17—C18—H18A109.3C35—C34—H34120.2
C19—C18—H18A109.3C34—C35—C36121.0 (2)
C17—C18—H18B109.3C34—C35—H35119.5
C19—C18—H18B109.3C36—C35—H35119.5
H18A—C18—H18B107.9C35—C36—C31119.5 (2)
C11—C19—C18113.34 (18)C35—C36—H36120.3
C11—C19—H19A108.9C31—C36—H36120.3
C18—C19—H19A108.9C5—C4—H4127.1
C11—C19—H19B108.9C3—C4—H4127.1
C18—C19—H19B108.9C4—C5—N1105.72 (18)
H19A—C19—H19B107.7N1—C5—C51124.28 (18)
C12—C11—C16118.3 (2)C4—C5—C51129.9 (2)
C12—C11—C19121.3 (2)N1—N2—C3105.28 (17)
C16—C11—C19120.4 (2)C3—C4—C5105.73 (19)
C11—C12—C13120.9 (2)C56—C51—C52118.17 (19)
C11—C12—H12119.5C56—C51—C5120.43 (18)
C13—C12—H12119.5C52—C51—C5121.37 (19)
C14—C13—C12120.1 (2)C53—C52—C51120.9 (2)
C14—C13—H13119.9C53—C52—H52119.6
C12—C13—H13119.9C51—C52—H52119.6
C13—C14—C15119.9 (2)C54—C53—C52119.6 (2)
C13—C14—H14120.1C54—C53—H53120.2
C15—C14—H14120.1C52—C53—H53120.2
C14—C15—C16119.8 (2)C53—C54—C55121.2 (2)
C14—C15—H15120.1C53—C54—Br54118.89 (16)
C16—C15—H15120.1C55—C54—Br54119.94 (16)
C11—C16—C15121.0 (2)C56—C55—C54118.8 (2)
C11—C16—H16119.5C56—C55—H55120.6
C15—C16—H16119.5C54—C55—H55120.6
N2—C3—C4110.84 (18)C55—C56—C51121.4 (2)
N2—C3—C31118.76 (19)C55—C56—H56119.3
C4—C3—C31130.38 (19)C51—C56—H56119.3
C32—C31—C36119.0 (2)
N2—N1—C17—C1872.0 (2)C33—C34—C35—C360.2 (4)
C5—N1—C17—C18111.5 (2)C34—C35—C36—C310.3 (3)
N1—C17—C18—C19176.02 (17)C32—C31—C36—C350.4 (3)
C17—C18—C19—C1170.4 (3)C3—C31—C36—C35179.7 (2)
C18—C19—C11—C12115.9 (2)N2—C3—C4—C50.6 (2)
C18—C19—C11—C1664.7 (3)C31—C3—C4—C5177.5 (2)
C16—C11—C12—C130.1 (3)N2—N1—C5—C40.2 (2)
C19—C11—C12—C13179.5 (2)C17—N1—C5—C4176.5 (2)
C11—C12—C13—C140.6 (4)N2—N1—C5—C51176.99 (18)
C12—C13—C14—C150.5 (4)C17—N1—C5—C516.4 (3)
C13—C14—C15—C160.1 (3)C3—C4—C5—N10.5 (2)
C12—C11—C16—C150.8 (3)C3—C4—C5—C51176.5 (2)
C19—C11—C16—C15179.8 (2)N1—C5—C51—C56145.5 (2)
C14—C15—C16—C110.8 (3)C4—C5—C51—C5638.0 (3)
C5—N1—N2—C30.2 (2)N1—C5—C51—C5236.4 (3)
C17—N1—N2—C3177.37 (17)C4—C5—C51—C52140.0 (2)
N1—N2—C3—C40.5 (2)C56—C51—C52—C531.1 (3)
N1—N2—C3—C31177.88 (18)C5—C51—C52—C53179.2 (2)
N2—C3—C31—C3214.6 (3)C51—C52—C53—C541.6 (3)
C4—C3—C31—C32163.4 (2)C52—C53—C54—C550.6 (3)
N2—C3—C31—C36166.0 (2)C52—C53—C54—Br54179.81 (16)
C4—C3—C31—C3616.0 (3)C53—C54—C55—C561.0 (3)
C36—C31—C32—C330.0 (3)Br54—C54—C55—C56178.64 (16)
C3—C31—C32—C33179.4 (2)C54—C55—C56—C511.5 (3)
C31—C32—C33—C340.4 (4)C52—C51—C56—C550.5 (3)
C32—C33—C34—C350.5 (4)C5—C51—C56—C55177.60 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C18—H18A···Cg1i0.992.813.625 (2)140
C56—H56···Cg2ii0.953.083.499 (2)108
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds