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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
CCDC reference: 177220
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (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
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?)
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
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
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.
Crystal data top
C6H5Cl2N | Dx = 1.634 Mg m−3 |
Mr = 162.01 | Melting point: 50 K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 13.1141 (6) Å | Cell parameters from 1724 reflections |
b = 3.8137 (1) Å | θ = 2.9–26.0° |
c = 13.1699 (7) Å | µ = 0.88 mm−1 |
β = 90.033 (2)° | T = 120 K |
V = 658.67 (11) Å3 | Lozenge, colourless |
Z = 4 | 0.20 × 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-anode | 1026 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
Detector resolution: 9.091 pixels mm-1 | θmax = 26.0°, θmin = 3.1° |
φ and ω scans to fill Ewald sphere | h = −16→16 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −4→4 |
Tmin = 0.844, Tmax = 0.917 | l = −16→11 |
2663 measured reflections | |
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)] = 0.026 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.074 | All 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 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.36 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 | |
Cl1 | 0.62141 (3) | 0.39302 (10) | 0.41633 (3) | 0.02093 (18) | |
Cl2 | 0.32357 (3) | 0.00778 (11) | 0.06569 (3) | 0.02322 (18) | |
N1 | 0.66639 (11) | 0.4760 (4) | 0.19545 (13) | 0.0182 (3) | |
H1A | 0.6739 (17) | 0.562 (5) | 0.1361 (17) | 0.027 (5)* | |
H1B | 0.6932 (17) | 0.610 (5) | 0.2417 (17) | 0.024 (5)* | |
C1 | 0.56937 (12) | 0.3472 (4) | 0.21737 (12) | 0.0136 (4) | |
C2 | 0.53915 (12) | 0.2817 (4) | 0.31821 (11) | 0.0136 (4) | |
C3 | 0.44446 (13) | 0.1366 (4) | 0.34038 (12) | 0.0161 (4) | |
H3 | 0.4255 (15) | 0.089 (5) | 0.4100 (14) | 0.017 (4)* | |
C4 | 0.37773 (12) | 0.0490 (4) | 0.26381 (13) | 0.0159 (4) | |
H4 | 0.3141 (17) | −0.052 (5) | 0.2761 (16) | 0.025 (5)* | |
C5 | 0.40697 (12) | 0.1140 (4) | 0.16412 (12) | 0.0148 (4) | |
C6 | 0.50159 (12) | 0.2583 (4) | 0.14094 (12) | 0.0152 (4) | |
H6 | 0.5210 (16) | 0.296 (5) | 0.0716 (15) | 0.027 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0206 (3) | 0.0268 (3) | 0.0154 (3) | −0.00097 (15) | −0.0042 (2) | −0.00346 (15) |
Cl2 | 0.0198 (3) | 0.0307 (3) | 0.0192 (3) | −0.00138 (16) | −0.0065 (2) | −0.00330 (16) |
N1 | 0.0143 (7) | 0.0217 (7) | 0.0186 (8) | −0.0027 (6) | 0.0016 (7) | 0.0017 (6) |
C1 | 0.0140 (8) | 0.0104 (7) | 0.0163 (8) | 0.0019 (5) | 0.0013 (8) | 0.0008 (6) |
C2 | 0.0151 (7) | 0.0129 (7) | 0.0129 (8) | 0.0026 (6) | −0.0040 (7) | −0.0017 (6) |
C3 | 0.0189 (8) | 0.0157 (8) | 0.0137 (8) | 0.0013 (6) | 0.0025 (8) | 0.0008 (6) |
C4 | 0.0130 (8) | 0.0152 (7) | 0.0195 (9) | −0.0006 (6) | 0.0021 (8) | 0.0000 (6) |
C5 | 0.0153 (8) | 0.0142 (8) | 0.0150 (8) | 0.0019 (6) | −0.0048 (7) | −0.0029 (6) |
C6 | 0.0167 (8) | 0.0167 (8) | 0.0122 (8) | 0.0023 (6) | 0.0017 (7) | 0.0020 (6) |
Geometric parameters (Å, º) top
Cl1—C2 | 1.7356 (17) | C2—C3 | 1.390 (2) |
Cl2—C5 | 1.7432 (18) | C3—C4 | 1.376 (3) |
N1—C1 | 1.394 (2) | C3—H3 | 0.966 (18) |
N1—H1A | 0.85 (2) | C4—C5 | 1.390 (2) |
N1—H1B | 0.87 (2) | C4—H4 | 0.93 (2) |
C1—C6 | 1.385 (3) | C5—C6 | 1.392 (2) |
C1—C2 | 1.409 (2) | C6—H6 | 0.959 (18) |
| | | |
C1—N1—H1A | 115.5 (16) | C2—C3—H3 | 120.2 (12) |
C1—N1—H1B | 115.5 (12) | C3—C4—C5 | 118.24 (14) |
H1A—N1—H1B | 111.7 (19) | C3—C4—H4 | 122.8 (14) |
C6—C1—N1 | 121.42 (14) | C5—C4—H4 | 119.0 (14) |
C6—C1—C2 | 117.46 (13) | C4—C5—C6 | 121.61 (16) |
N1—C1—C2 | 121.01 (16) | C4—C5—Cl2 | 119.19 (12) |
C3—C2—C1 | 121.36 (15) | C6—C5—Cl2 | 119.20 (12) |
C3—C2—Cl1 | 119.72 (12) | C1—C6—C5 | 120.63 (13) |
C1—C2—Cl1 | 118.91 (12) | C1—C6—H6 | 119.0 (13) |
C4—C3—C2 | 120.69 (14) | C5—C6—H6 | 120.3 (13) |
C4—C3—H3 | 119.1 (12) | | |
| | | |
C6—C1—C2—C3 | −0.7 (2) | C3—C4—C5—C6 | 1.0 (2) |
N1—C1—C2—C3 | −176.70 (13) | C3—C4—C5—Cl2 | −179.64 (11) |
C6—C1—C2—Cl1 | −179.41 (10) | N1—C1—C6—C5 | 176.81 (14) |
N1—C1—C2—Cl1 | 4.6 (2) | C2—C1—C6—C5 | 0.8 (2) |
C1—C2—C3—C4 | 0.7 (2) | C4—C5—C6—C1 | −1.0 (2) |
Cl1—C2—C3—C4 | 179.48 (11) | Cl2—C5—C6—C1 | 179.67 (11) |
C2—C3—C4—C5 | −0.9 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···N1i | 0.87 (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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