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Mol­ecules of p-bromo­anilinium chloride, C6H7BrN+·Cl or [BRANH]+·Cl, are linked via N+—H...Cl hydrogen bonds to form R42(8) supramolecular synthons parallel to the bc plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680502595X/tk6250sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680502595X/tk6250Isup2.hkl
Contains datablock I

CCDC reference: 285523

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.028
  • wR factor = 0.072
  • Data-to-parameter ratio = 9.5

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 23.50 Deg.
Author Response: Very small crystal used for data collection
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.66
Author Response: Very small crystal used for data collection

Alert level B THETM01_ALERT_3_B The value of sine(theta_max)/wavelength is less than 0.575 Calculated sin(theta_max)/wavelength = 0.5611 PLAT023_ALERT_3_B Resolution (too) Low [sin(th)/Lambda < 0.6]..... 23.50 Deg.
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 23.50 From the CIF: _diffrn_reflns_theta_full 23.50 From the CIF: _reflns_number_total 1113 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 1186 Completeness (_total/calc) 93.84% REFNR01_ALERT_3_C Ratio of reflections to parameters is < 10 for a centrosymmetric structure sine(theta)/lambda 0.5611 Proportion of unique data used 0.7017 Ratio reflections to parameters 9.5244 PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.94 PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.52 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT350_ALERT_3_C Short C-H Bond (0.96A) C3 - H3 ... 0.84 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. Cl1 .. 3.59 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 Cl
2 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 8 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 10 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XCS (Colapietro et al., 1992); cell refinement: XCS; data reduction: XCS; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

p-Bromoaniline hydrochloride top
Crystal data top
C6H7BrN+·ClF(000) = 408
Mr = 208.49Dx = 1.727 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.710689 Å
Hall symbol: -P 2ybcCell parameters from 12 reflections
a = 8.629 (2) Åθ = 15–20°
b = 9.784 (2) ŵ = 5.37 mm1
c = 9.863 (9) ÅT = 298 K
β = 105.61 (5)°Prism, colourless
V = 802.0 (8) Å30.18 × 0.18 × 0.15 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4F
diffractometer
781 reflections with I > 2σ(I)
Radiation source: X-ray tubeRint = 0.011
Graphite monochromatorθmax = 23.5°, θmin = 2.5°
θ/2θ scansh = 99
Absorption correction: ψ scan
(North et al., 1968)
k = 010
Tmin = 0.396, Tmax = 0.450l = 011
3628 measured reflections3 standard reflections every 33 min
1113 independent reflections intensity decay: 5%
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)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0331P)2 + 2.5739P]
where P = (Fo2 + 2Fc2)/3
781 reflections(Δ/σ)max = 0.001
82 parametersΔρmax = 0.57 e Å3
0 restraintsΔρmin = 0.56 e Å3
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
xyzUiso*/Ueq
Br10.19329 (7)0.03645 (7)0.23311 (6)0.0576 (2)
Cl10.58919 (15)0.10949 (14)0.33157 (14)0.0387 (3)
N10.4405 (5)0.3035 (4)0.0757 (4)0.0344 (10)
C10.2878 (6)0.2405 (5)0.0004 (5)0.0332 (12)
C20.1458 (7)0.2974 (5)0.0100 (6)0.0410 (13)
C30.0016 (6)0.2370 (6)0.0610 (6)0.0449 (14)
C40.0036 (6)0.1205 (6)0.1385 (5)0.0373 (13)
C50.1465 (7)0.0654 (5)0.1464 (5)0.0430 (14)
C60.2902 (6)0.1250 (6)0.0776 (5)0.0406 (13)
H20.14980.37910.05880.049*
H30.08760.26650.05440.055*
H50.15010.00520.19820.027*
H60.39760.08210.07910.027*
H110.50270.24710.14500.041*
H120.50170.32170.02300.041*
H130.42760.38260.10750.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0492 (4)0.0590 (4)0.0538 (4)0.0071 (3)0.0050 (3)0.0050 (3)
Cl10.0385 (7)0.0376 (7)0.0420 (7)0.0024 (6)0.0145 (6)0.0050 (6)
N10.037 (2)0.032 (2)0.034 (2)0.001 (2)0.0097 (19)0.002 (2)
C10.043 (3)0.031 (3)0.024 (2)0.000 (2)0.007 (2)0.004 (2)
C20.049 (3)0.036 (3)0.041 (3)0.002 (3)0.017 (3)0.007 (2)
C30.033 (3)0.052 (4)0.050 (3)0.003 (3)0.011 (3)0.002 (3)
C40.035 (3)0.043 (3)0.032 (3)0.004 (3)0.005 (2)0.004 (3)
C50.058 (4)0.037 (3)0.036 (3)0.004 (3)0.014 (3)0.010 (2)
C60.040 (3)0.043 (3)0.041 (3)0.006 (3)0.014 (3)0.004 (3)
Geometric parameters (Å, º) top
Br1—C41.892 (5)C2—H20.9280
N1—C11.463 (6)C3—C41.376 (8)
N1—H110.9292C3—H30.8407
N1—H120.8536C4—C51.367 (8)
N1—H130.8538C5—C61.373 (7)
C1—C21.372 (7)C5—H50.8647
C1—C61.371 (7)C6—H61.0211
C2—C31.385 (8)
C1—N1—H11112.7C2—C3—C4119.4 (5)
C1—N1—H12113.5C4—C3—H3118.4
H11—N1—H12104.0C2—C3—H3122.1
C1—N1—H13112.3Br1—C4—C5120.3 (4)
H11—N1—H13112.1Br1—C4—C3119.4 (4)
H12—N1—H13101.4C3—C4—C5120.3 (5)
N1—C1—C2119.5 (5)C4—C5—C6120.9 (5)
N1—C1—C6119.0 (5)C4—C5—H5121.7
C2—C1—C6121.5 (5)C6—C5—H5117.4
C1—C2—C3119.3 (5)C1—C6—C5118.7 (5)
C1—C2—H2118.4C1—C6—H6119.9
C3—C2—H2122.2C5—C6—H6121.4
C6—C1—C2—C30.1 (8)C3—C4—C5—C60.2 (8)
N1—C1—C2—C3179.7 (5)Br1—C4—C5—C6179.7 (4)
C1—C2—C3—C40.6 (8)C2—C1—C6—C50.5 (8)
C2—C3—C4—C50.5 (8)N1—C1—C6—C5179.1 (5)
C2—C3—C4—Br1179.0 (4)C4—C5—C6—C10.7 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H11···Cl10.932.243.143 (5)164
N1—H12···Cl1i0.852.313.136 (5)162
N1—H13···Cl1ii0.852.313.161 (4)171
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x1, y+1/2, z1/2.
 

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