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Molecules of
p-bromoanilinium chloride, C
6H
7BrN
+·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
CCDC reference: 285523
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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+·Cl− | F(000) = 408 |
Mr = 208.49 | Dx = 1.727 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.710689 Å |
Hall symbol: -P 2ybc | Cell parameters from 12 reflections |
a = 8.629 (2) Å | θ = 15–20° |
b = 9.784 (2) Å | µ = 5.37 mm−1 |
c = 9.863 (9) Å | T = 298 K |
β = 105.61 (5)° | Prism, colourless |
V = 802.0 (8) Å3 | 0.18 × 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 tube | Rint = 0.011 |
Graphite monochromator | θmax = 23.5°, θmin = 2.5° |
θ/2θ scans | h = −9→9 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→10 |
Tmin = 0.396, Tmax = 0.450 | l = 0→11 |
3628 measured reflections | 3 standard reflections every 33 min |
1113 independent reflections | intensity decay: 5% |
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)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.072 | H-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 parameters | Δρmax = 0.57 e Å−3 |
0 restraints | Δρmin = −0.56 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 | |
Br1 | 0.19329 (7) | 0.03645 (7) | 0.23311 (6) | 0.0576 (2) | |
Cl1 | −0.58919 (15) | 0.10949 (14) | −0.33157 (14) | 0.0387 (3) | |
N1 | −0.4405 (5) | 0.3035 (4) | −0.0757 (4) | 0.0344 (10) | |
C1 | −0.2878 (6) | 0.2405 (5) | −0.0004 (5) | 0.0332 (12) | |
C2 | −0.1458 (7) | 0.2974 (5) | −0.0100 (6) | 0.0410 (13) | |
C3 | −0.0016 (6) | 0.2370 (6) | 0.0610 (6) | 0.0449 (14) | |
C4 | −0.0036 (6) | 0.1205 (6) | 0.1385 (5) | 0.0373 (13) | |
C5 | −0.1465 (7) | 0.0654 (5) | 0.1464 (5) | 0.0430 (14) | |
C6 | −0.2902 (6) | 0.1250 (6) | 0.0776 (5) | 0.0406 (13) | |
H2 | −0.1498 | 0.3791 | −0.0588 | 0.049* | |
H3 | 0.0876 | 0.2665 | 0.0544 | 0.055* | |
H5 | −0.1501 | −0.0052 | 0.1982 | 0.027* | |
H6 | −0.3976 | 0.0821 | 0.0791 | 0.027* | |
H11 | −0.5027 | 0.2471 | −0.1450 | 0.041* | |
H12 | −0.5017 | 0.3217 | −0.0230 | 0.041* | |
H13 | −0.4276 | 0.3826 | −0.1075 | 0.041* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0492 (4) | 0.0590 (4) | 0.0538 (4) | 0.0071 (3) | −0.0050 (3) | 0.0050 (3) |
Cl1 | 0.0385 (7) | 0.0376 (7) | 0.0420 (7) | −0.0024 (6) | 0.0145 (6) | −0.0050 (6) |
N1 | 0.037 (2) | 0.032 (2) | 0.034 (2) | −0.001 (2) | 0.0097 (19) | −0.002 (2) |
C1 | 0.043 (3) | 0.031 (3) | 0.024 (2) | 0.000 (2) | 0.007 (2) | −0.004 (2) |
C2 | 0.049 (3) | 0.036 (3) | 0.041 (3) | −0.002 (3) | 0.017 (3) | 0.007 (2) |
C3 | 0.033 (3) | 0.052 (4) | 0.050 (3) | −0.003 (3) | 0.011 (3) | 0.002 (3) |
C4 | 0.035 (3) | 0.043 (3) | 0.032 (3) | 0.004 (3) | 0.005 (2) | −0.004 (3) |
C5 | 0.058 (4) | 0.037 (3) | 0.036 (3) | 0.004 (3) | 0.014 (3) | 0.010 (2) |
C6 | 0.040 (3) | 0.043 (3) | 0.041 (3) | −0.006 (3) | 0.014 (3) | 0.004 (3) |
Geometric parameters (Å, º) top
Br1—C4 | 1.892 (5) | C2—H2 | 0.9280 |
N1—C1 | 1.463 (6) | C3—C4 | 1.376 (8) |
N1—H11 | 0.9292 | C3—H3 | 0.8407 |
N1—H12 | 0.8536 | C4—C5 | 1.367 (8) |
N1—H13 | 0.8538 | C5—C6 | 1.373 (7) |
C1—C2 | 1.372 (7) | C5—H5 | 0.8647 |
C1—C6 | 1.371 (7) | C6—H6 | 1.0211 |
C2—C3 | 1.385 (8) | | |
| | | |
C1—N1—H11 | 112.7 | C2—C3—C4 | 119.4 (5) |
C1—N1—H12 | 113.5 | C4—C3—H3 | 118.4 |
H11—N1—H12 | 104.0 | C2—C3—H3 | 122.1 |
C1—N1—H13 | 112.3 | Br1—C4—C5 | 120.3 (4) |
H11—N1—H13 | 112.1 | Br1—C4—C3 | 119.4 (4) |
H12—N1—H13 | 101.4 | C3—C4—C5 | 120.3 (5) |
N1—C1—C2 | 119.5 (5) | C4—C5—C6 | 120.9 (5) |
N1—C1—C6 | 119.0 (5) | C4—C5—H5 | 121.7 |
C2—C1—C6 | 121.5 (5) | C6—C5—H5 | 117.4 |
C1—C2—C3 | 119.3 (5) | C1—C6—C5 | 118.7 (5) |
C1—C2—H2 | 118.4 | C1—C6—H6 | 119.9 |
C3—C2—H2 | 122.2 | C5—C6—H6 | 121.4 |
| | | |
C6—C1—C2—C3 | −0.1 (8) | C3—C4—C5—C6 | −0.2 (8) |
N1—C1—C2—C3 | −179.7 (5) | Br1—C4—C5—C6 | −179.7 (4) |
C1—C2—C3—C4 | 0.6 (8) | C2—C1—C6—C5 | −0.5 (8) |
C2—C3—C4—C5 | −0.5 (8) | N1—C1—C6—C5 | 179.1 (5) |
C2—C3—C4—Br1 | 179.0 (4) | C4—C5—C6—C1 | 0.7 (8) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···Cl1 | 0.93 | 2.24 | 3.143 (5) | 164 |
N1—H12···Cl1i | 0.85 | 2.31 | 3.136 (5) | 162 |
N1—H13···Cl1ii | 0.85 | 2.31 | 3.161 (4) | 171 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x−1, y+1/2, −z−1/2. |
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