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The pseudo-tetragonal cell of the title compound, C6H5Cl2N, is correctly described as monoclinic with β = 90.033 (2)°. Amine groups are linked by intermolecular hydrogen bonding involving only one H atom of each group.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801019511/cf6126sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801019511/cf6126Isup2.hkl
Contains datablock I

CCDC reference: 177220

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.026
  • wR factor = 0.074
  • Data-to-parameter ratio = 10.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Red Alert Alert Level A:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 26.00 From the CIF: _reflns_number_total 1088 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 1302 Completeness (_total/calc) 83.56% Alert A: < 85% complete (theta max?)
Amber Alert Alert Level B:
CELLV_02 Alert B The supplied cell volume s.u. differs from that calculated from the cell parameter s.u.'s by > 4 Calculated cell volume su = 4.93 Cell volume su given = 11.00
Yellow Alert Alert Level C:
PLAT_420 Alert C D-H Without Acceptor N(1) - H(1A) ?
1 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; 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) and PLATON (Spek, 2001); software used to prepare material for publication: SHELXL97 and PLATON.

2,5-Dichloroaniline top
Crystal data top
C6H5Cl2NDx = 1.634 Mg m3
Mr = 162.01Melting point: 50 K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 13.1141 (6) ÅCell parameters from 1724 reflections
b = 3.8137 (1) Åθ = 2.9–26.0°
c = 13.1699 (7) ŵ = 0.88 mm1
β = 90.033 (2)°T = 120 K
V = 658.67 (11) Å3Lozenge, colourless
Z = 40.20 × 0.15 × 0.10 mm
F(000) = 328
Data collection top
Enraf-Nonius KappaCCD area-detector
diffractometer
1088 independent reflections
Radiation source: Enraf-Nonius FR591 rotating-anode1026 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
Detector resolution: 9.091 pixels mm-1θmax = 26.0°, θmin = 3.1°
φ and ω scans to fill Ewald sphereh = 1616
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
k = 44
Tmin = 0.844, Tmax = 0.917l = 1611
2663 measured reflections
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)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074All H-atom parameters refined
S = 1.03 w = 1/[σ2(Fo2) + (0.0449P)2 + 0.1577P]
where P = (Fo2 + 2Fc2)/3
1088 reflections(Δ/σ)max = 0.001
102 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.36 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
Cl10.62141 (3)0.39302 (10)0.41633 (3)0.02093 (18)
Cl20.32357 (3)0.00778 (11)0.06569 (3)0.02322 (18)
N10.66639 (11)0.4760 (4)0.19545 (13)0.0182 (3)
H1A0.6739 (17)0.562 (5)0.1361 (17)0.027 (5)*
H1B0.6932 (17)0.610 (5)0.2417 (17)0.024 (5)*
C10.56937 (12)0.3472 (4)0.21737 (12)0.0136 (4)
C20.53915 (12)0.2817 (4)0.31821 (11)0.0136 (4)
C30.44446 (13)0.1366 (4)0.34038 (12)0.0161 (4)
H30.4255 (15)0.089 (5)0.4100 (14)0.017 (4)*
C40.37773 (12)0.0490 (4)0.26381 (13)0.0159 (4)
H40.3141 (17)0.052 (5)0.2761 (16)0.025 (5)*
C50.40697 (12)0.1140 (4)0.16412 (12)0.0148 (4)
C60.50159 (12)0.2583 (4)0.14094 (12)0.0152 (4)
H60.5210 (16)0.296 (5)0.0716 (15)0.027 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0206 (3)0.0268 (3)0.0154 (3)0.00097 (15)0.0042 (2)0.00346 (15)
Cl20.0198 (3)0.0307 (3)0.0192 (3)0.00138 (16)0.0065 (2)0.00330 (16)
N10.0143 (7)0.0217 (7)0.0186 (8)0.0027 (6)0.0016 (7)0.0017 (6)
C10.0140 (8)0.0104 (7)0.0163 (8)0.0019 (5)0.0013 (8)0.0008 (6)
C20.0151 (7)0.0129 (7)0.0129 (8)0.0026 (6)0.0040 (7)0.0017 (6)
C30.0189 (8)0.0157 (8)0.0137 (8)0.0013 (6)0.0025 (8)0.0008 (6)
C40.0130 (8)0.0152 (7)0.0195 (9)0.0006 (6)0.0021 (8)0.0000 (6)
C50.0153 (8)0.0142 (8)0.0150 (8)0.0019 (6)0.0048 (7)0.0029 (6)
C60.0167 (8)0.0167 (8)0.0122 (8)0.0023 (6)0.0017 (7)0.0020 (6)
Geometric parameters (Å, º) top
Cl1—C21.7356 (17)C2—C31.390 (2)
Cl2—C51.7432 (18)C3—C41.376 (3)
N1—C11.394 (2)C3—H30.966 (18)
N1—H1A0.85 (2)C4—C51.390 (2)
N1—H1B0.87 (2)C4—H40.93 (2)
C1—C61.385 (3)C5—C61.392 (2)
C1—C21.409 (2)C6—H60.959 (18)
C1—N1—H1A115.5 (16)C2—C3—H3120.2 (12)
C1—N1—H1B115.5 (12)C3—C4—C5118.24 (14)
H1A—N1—H1B111.7 (19)C3—C4—H4122.8 (14)
C6—C1—N1121.42 (14)C5—C4—H4119.0 (14)
C6—C1—C2117.46 (13)C4—C5—C6121.61 (16)
N1—C1—C2121.01 (16)C4—C5—Cl2119.19 (12)
C3—C2—C1121.36 (15)C6—C5—Cl2119.20 (12)
C3—C2—Cl1119.72 (12)C1—C6—C5120.63 (13)
C1—C2—Cl1118.91 (12)C1—C6—H6119.0 (13)
C4—C3—C2120.69 (14)C5—C6—H6120.3 (13)
C4—C3—H3119.1 (12)
C6—C1—C2—C30.7 (2)C3—C4—C5—C61.0 (2)
N1—C1—C2—C3176.70 (13)C3—C4—C5—Cl2179.64 (11)
C6—C1—C2—Cl1179.41 (10)N1—C1—C6—C5176.81 (14)
N1—C1—C2—Cl14.6 (2)C2—C1—C6—C50.8 (2)
C1—C2—C3—C40.7 (2)C4—C5—C6—C11.0 (2)
Cl1—C2—C3—C4179.48 (11)Cl2—C5—C6—C1179.67 (11)
C2—C3—C4—C50.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···N1i0.87 (2)2.45 (2)3.241 (2)151 (2)
Symmetry code: (i) x+3/2, y+1/2, z+1/2.
 

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