Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520616011094/um5004sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011094/um5004Isup2.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520616011094/um5004sup3.pdf |
CCDC reference: 1459028
Data collection: CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44); cell refinement: CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44); data reduction: CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44); program(s) used to refine structure: SHELXL (Sheldrick, 2008); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).
C13H15N2·Cl·2(H2O) | Dx = 1.345 Mg m−3 |
Mr = 270.75 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbcn | Cell parameters from 1701 reflections |
a = 17.8252 (7) Å | θ = 3.2–29.0° |
b = 7.2708 (2) Å | µ = 0.28 mm−1 |
c = 20.6396 (7) Å | T = 100 K |
V = 2674.98 (16) Å3 | Needle, colourless |
Z = 8 | 0.61 × 0.14 × 0.1 mm |
F(000) = 1152 |
SuperNova, Single source at offset, Eos diffractometer | 2367 independent reflections |
Mirror monochromator | 2026 reflections with I > 2σ(I) |
Detector resolution: 15.9631 pixels mm-1 | Rint = 0.017 |
ω scans | θmax = 25.4°, θmin = 3.0° |
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | h = −11→20 |
Tmin = 0.841, Tmax = 1.000 | k = −8→4 |
4930 measured reflections | l = −24→19 |
Refinement on F2 | 234 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.107 | w = 1/[σ2(Fo2) + (0.0473P)2 + 2.1477P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
2367 reflections | Δρmax = 0.29 e Å−3 |
221 parameters | Δρmin = −0.29 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.32651 (11) | 0.5998 (2) | 0.36954 (8) | 0.0192 (4) | |
H1 | 0.3731 (15) | 0.618 (3) | 0.3849 (11) | 0.023* | |
C2 | 0.32197 (12) | 0.5601 (2) | 0.30558 (9) | 0.0182 (5) | |
C3 | 0.25260 (13) | 0.5385 (3) | 0.27591 (9) | 0.0194 (4) | |
C4 | 0.18668 (12) | 0.5524 (3) | 0.31418 (10) | 0.0192 (5) | |
C5 | 0.19371 (12) | 0.5975 (3) | 0.38174 (10) | 0.0175 (5) | |
C6 | 0.26480 (12) | 0.6202 (3) | 0.40778 (9) | 0.0176 (4) | |
C7 | 0.39321 (14) | 0.5412 (3) | 0.27018 (10) | 0.0266 (5) | |
H7A | 0.4412 | 0.5505 | 0.2899 | 0.032* | 0.413 (9) |
H7BA | 0.4284 | 0.4700 | 0.2975 | 0.032* | 0.587 (9) |
H7BB | 0.4149 | 0.6654 | 0.2644 | 0.032* | 0.587 (9) |
C8A | 0.3822 (6) | 0.5087 (12) | 0.2058 (3) | 0.034 (2) | 0.413 (9) |
H8A | 0.4258 | 0.5113 | 0.1794 | 0.041* | 0.413 (9) |
C9A | 0.3139 (4) | 0.4718 (13) | 0.1735 (5) | 0.042 (2) | 0.413 (9) |
H9A | 0.3138 | 0.4292 | 0.1300 | 0.050* | 0.413 (9) |
C8B | 0.3889 (4) | 0.4483 (9) | 0.2035 (2) | 0.0269 (14) | 0.587 (9) |
H8BA | 0.4355 | 0.4710 | 0.1788 | 0.032* | 0.587 (9) |
H8BB | 0.3823 | 0.3139 | 0.2085 | 0.032* | 0.587 (9) |
C9B | 0.3233 (3) | 0.5294 (9) | 0.1692 (3) | 0.0285 (14) | 0.587 (9) |
H9BA | 0.3196 | 0.4744 | 0.1254 | 0.034* | 0.587 (9) |
H9BB | 0.3315 | 0.6633 | 0.1639 | 0.034* | 0.587 (9) |
C10 | 0.24876 (13) | 0.4981 (3) | 0.20558 (10) | 0.0260 (5) | |
H10 | 0.2019 | 0.4909 | 0.1838 | 0.031* | 0.413 (9) |
H10A | 0.2096 | 0.5767 | 0.1858 | 0.031* | 0.587 (9) |
H10B | 0.2333 | 0.3684 | 0.1997 | 0.031* | 0.587 (9) |
N11 | 0.11904 (12) | 0.5245 (3) | 0.28843 (10) | 0.0265 (5) | |
H11A | 0.1116 (15) | 0.504 (3) | 0.2476 (13) | 0.032* | |
H11B | 0.0764 (15) | 0.527 (4) | 0.3115 (13) | 0.032* | |
C12 | 0.12871 (13) | 0.6192 (3) | 0.42298 (10) | 0.0246 (5) | |
H12A | 0.1077 | 0.4955 | 0.4316 | 0.029* | 0.413 (9) |
H12B | 0.0903 | 0.6890 | 0.3985 | 0.029* | 0.413 (9) |
H12 | 0.0794 | 0.6083 | 0.4060 | 0.029* | 0.587 (9) |
C13A | 0.1405 (7) | 0.7152 (13) | 0.4881 (4) | 0.023 (2) | 0.413 (9) |
H13A | 0.1461 | 0.8492 | 0.4811 | 0.028* | 0.413 (9) |
H13B | 0.0962 | 0.6950 | 0.5161 | 0.028* | 0.413 (9) |
C14A | 0.2087 (5) | 0.642 (2) | 0.5206 (6) | 0.025 (3) | 0.413 (9) |
H14A | 0.2015 | 0.5101 | 0.5312 | 0.030* | 0.413 (9) |
H14B | 0.2180 | 0.7094 | 0.5614 | 0.030* | 0.413 (9) |
C13B | 0.1403 (5) | 0.6553 (10) | 0.4863 (3) | 0.0226 (16) | 0.587 (9) |
H13C | 0.0984 | 0.6605 | 0.5147 | 0.027* | 0.587 (9) |
C14B | 0.2133 (3) | 0.6857 (15) | 0.5115 (4) | 0.0240 (18) | 0.587 (9) |
H14C | 0.2185 | 0.7227 | 0.5554 | 0.029* | 0.587 (9) |
C15 | 0.27584 (13) | 0.6638 (3) | 0.47513 (10) | 0.0246 (5) | |
H15A | 0.2931 | 0.7930 | 0.4779 | 0.030* | 0.413 (9) |
H15B | 0.3170 | 0.5855 | 0.4917 | 0.030* | 0.413 (9) |
H15 | 0.3246 | 0.6766 | 0.4932 | 0.030* | 0.587 (9) |
Cl16 | 0.04925 (3) | 0.47210 (8) | 0.14505 (2) | 0.02686 (18) | |
O17 | 0.05413 (11) | 0.8247 (3) | 0.05294 (9) | 0.0360 (4) | |
H17A | 0.0540 (16) | 0.727 (3) | 0.0736 (12) | 0.043* | |
H17B | 0.0261 (15) | 0.903 (3) | 0.0667 (13) | 0.043* | |
O18 | 0.47049 (9) | 0.6413 (2) | 0.42146 (7) | 0.0250 (4) | |
H18A | 0.4955 (14) | 0.723 (3) | 0.4030 (11) | 0.030* | |
H18B | 0.4611 (14) | 0.672 (3) | 0.4588 (9) | 0.030* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0165 (10) | 0.0224 (9) | 0.0186 (9) | −0.0014 (8) | −0.0010 (7) | −0.0019 (7) |
C2 | 0.0235 (12) | 0.0149 (10) | 0.0163 (9) | 0.0012 (9) | 0.0015 (8) | 0.0007 (8) |
C3 | 0.0226 (11) | 0.0175 (10) | 0.0179 (9) | 0.0027 (9) | −0.0014 (8) | −0.0006 (8) |
C4 | 0.0226 (12) | 0.0141 (10) | 0.0210 (10) | 0.0028 (9) | −0.0044 (8) | 0.0015 (8) |
C5 | 0.0187 (11) | 0.0161 (10) | 0.0176 (9) | −0.0004 (9) | −0.0009 (8) | 0.0002 (8) |
C6 | 0.0193 (11) | 0.0147 (10) | 0.0189 (9) | −0.0004 (9) | 0.0017 (8) | −0.0001 (8) |
C7 | 0.0306 (13) | 0.0290 (12) | 0.0203 (10) | −0.0010 (10) | 0.0019 (9) | −0.0020 (9) |
C8A | 0.024 (4) | 0.049 (5) | 0.028 (3) | −0.006 (3) | 0.010 (3) | −0.016 (3) |
C9A | 0.034 (3) | 0.061 (6) | 0.031 (4) | −0.003 (3) | −0.006 (3) | −0.019 (4) |
C8B | 0.029 (3) | 0.034 (3) | 0.018 (2) | 0.001 (2) | 0.0036 (18) | −0.0063 (18) |
C9B | 0.035 (3) | 0.028 (3) | 0.023 (2) | 0.011 (2) | −0.004 (2) | −0.010 (2) |
C10 | 0.0240 (12) | 0.0307 (12) | 0.0234 (10) | 0.0032 (10) | −0.0037 (9) | −0.0032 (9) |
N11 | 0.0213 (11) | 0.0353 (11) | 0.0228 (10) | 0.0010 (9) | −0.0065 (8) | −0.0036 (9) |
C12 | 0.0225 (12) | 0.0282 (12) | 0.0229 (10) | −0.0011 (10) | −0.0035 (9) | 0.0001 (9) |
C13A | 0.024 (4) | 0.023 (5) | 0.023 (3) | −0.005 (3) | 0.005 (2) | 0.009 (3) |
C14A | 0.026 (4) | 0.023 (6) | 0.027 (4) | 0.000 (3) | 0.003 (3) | −0.001 (3) |
C13B | 0.021 (2) | 0.025 (4) | 0.022 (2) | −0.001 (3) | 0.0032 (17) | 0.004 (2) |
C14B | 0.027 (3) | 0.026 (5) | 0.019 (3) | −0.001 (2) | −0.0002 (18) | −0.009 (2) |
C15 | 0.0224 (13) | 0.0289 (12) | 0.0227 (10) | −0.0008 (10) | −0.0010 (9) | −0.0034 (9) |
Cl16 | 0.0224 (3) | 0.0364 (3) | 0.0218 (3) | −0.0012 (2) | −0.0052 (2) | −0.0039 (2) |
O17 | 0.0288 (11) | 0.0426 (11) | 0.0367 (10) | 0.0010 (9) | 0.0008 (8) | 0.0119 (8) |
O18 | 0.0231 (9) | 0.0353 (9) | 0.0167 (7) | −0.0065 (7) | −0.0001 (6) | 0.0001 (7) |
N1—H1 | 0.90 (3) | C10—H10 | 0.9500 |
N1—C2 | 1.354 (3) | C10—H10A | 0.9900 |
N1—C6 | 1.362 (3) | C10—H10B | 0.9900 |
C2—C3 | 1.389 (3) | N11—H11A | 0.87 (3) |
C2—C7 | 1.471 (3) | N11—H11B | 0.90 (3) |
C3—C4 | 1.419 (3) | C12—H12A | 0.9900 |
C3—C10 | 1.483 (3) | C12—H12B | 0.9900 |
C4—C5 | 1.438 (3) | C12—H12 | 0.9500 |
C4—N11 | 1.333 (3) | C12—C13A | 1.529 (6) |
C5—C6 | 1.386 (3) | C12—C13B | 1.349 (5) |
C5—C12 | 1.446 (3) | C13A—H13A | 0.9900 |
C6—C15 | 1.439 (3) | C13A—H13B | 0.9900 |
C7—H7A | 0.9500 | C13A—C14A | 1.488 (7) |
C7—H7BA | 0.9900 | C14A—H14A | 0.9900 |
C7—H7BB | 0.9900 | C14A—H14B | 0.9900 |
C7—C8A | 1.363 (6) | C14A—C15 | 1.528 (6) |
C7—C8B | 1.534 (5) | C13B—H13C | 0.9500 |
C8A—H8A | 0.9500 | C13B—C14B | 1.420 (7) |
C8A—C9A | 1.415 (7) | C14B—H14C | 0.9500 |
C9A—H9A | 0.9500 | C14B—C15 | 1.353 (5) |
C9A—C10 | 1.350 (6) | C15—H15A | 0.9900 |
C8B—H8BA | 0.9900 | C15—H15B | 0.9900 |
C8B—H8BB | 0.9900 | C15—H15 | 0.9500 |
C8B—C9B | 1.488 (6) | O17—H17A | 0.830 (17) |
C9B—H9BA | 0.9900 | O17—H17B | 0.810 (17) |
C9B—H9BB | 0.9900 | O18—H18A | 0.834 (17) |
C9B—C10 | 1.544 (5) | O18—H18B | 0.818 (16) |
C2—N1—H1 | 115.4 (15) | C3—C10—H10B | 108.7 |
C2—N1—C6 | 122.70 (19) | C9A—C10—C3 | 118.0 (5) |
C6—N1—H1 | 121.8 (15) | C9A—C10—H10 | 121.0 |
N1—C2—C3 | 120.48 (19) | C9B—C10—H10A | 108.7 |
N1—C2—C7 | 116.91 (19) | C9B—C10—H10B | 108.7 |
C3—C2—C7 | 122.61 (18) | H10A—C10—H10B | 107.6 |
C2—C3—C4 | 118.93 (18) | C4—N11—H11A | 123.5 (18) |
C2—C3—C10 | 119.68 (19) | C4—N11—H11B | 123.5 (17) |
C4—C3—C10 | 121.4 (2) | H11A—N11—H11B | 113 (2) |
C3—C4—C5 | 118.93 (19) | C5—C12—H12A | 108.0 |
N11—C4—C3 | 121.07 (19) | C5—C12—H12B | 108.0 |
N11—C4—C5 | 120.0 (2) | C5—C12—H12 | 121.0 |
C4—C5—C12 | 121.72 (19) | C5—C12—C13A | 117.2 (5) |
C6—C5—C4 | 118.86 (19) | H12A—C12—H12B | 107.2 |
C6—C5—C12 | 119.41 (18) | C13A—C12—H12A | 108.0 |
N1—C6—C5 | 120.04 (18) | C13A—C12—H12B | 108.0 |
N1—C6—C15 | 118.25 (19) | C13B—C12—C5 | 118.0 (4) |
C5—C6—C15 | 121.71 (19) | C13B—C12—H12 | 121.0 |
C2—C7—H7A | 124.0 | C12—C13A—H13A | 109.6 |
C2—C7—H7BA | 108.2 | C12—C13A—H13B | 109.6 |
C2—C7—H7BB | 108.2 | H13A—C13A—H13B | 108.1 |
C2—C7—C8B | 116.3 (3) | C14A—C13A—C12 | 110.1 (9) |
H7BA—C7—H7BB | 107.4 | C14A—C13A—H13A | 109.6 |
C8A—C7—C2 | 112.1 (5) | C14A—C13A—H13B | 109.6 |
C8A—C7—H7A | 124.0 | C13A—C14A—H14A | 109.9 |
C8B—C7—H7BA | 108.2 | C13A—C14A—H14B | 109.9 |
C8B—C7—H7BB | 108.2 | C13A—C14A—C15 | 109.0 (8) |
C7—C8A—H8A | 116.0 | H14A—C14A—H14B | 108.3 |
C7—C8A—C9A | 128.1 (9) | C15—C14A—H14A | 109.9 |
C9A—C8A—H8A | 116.0 | C15—C14A—H14B | 109.9 |
C8A—C9A—H9A | 120.6 | C12—C13B—H13C | 119.1 |
C10—C9A—C8A | 118.8 (9) | C12—C13B—C14B | 121.7 (7) |
C10—C9A—H9A | 120.6 | C14B—C13B—H13C | 119.1 |
C7—C8B—H8BA | 110.3 | C13B—C14B—H14C | 118.9 |
C7—C8B—H8BB | 110.3 | C15—C14B—C13B | 122.2 (7) |
H8BA—C8B—H8BB | 108.6 | C15—C14B—H14C | 118.9 |
C9B—C8B—C7 | 107.0 (5) | C6—C15—C14A | 117.5 (6) |
C9B—C8B—H8BA | 110.3 | C6—C15—H15A | 107.9 |
C9B—C8B—H8BB | 110.3 | C6—C15—H15B | 107.9 |
C8B—C9B—H9BA | 109.1 | C6—C15—H15 | 121.7 |
C8B—C9B—H9BB | 109.1 | C14A—C15—H15A | 107.9 |
C8B—C9B—C10 | 112.7 (5) | C14A—C15—H15B | 107.9 |
H9BA—C9B—H9BB | 107.8 | C14B—C15—C6 | 116.7 (4) |
C10—C9B—H9BA | 109.1 | C14B—C15—H15 | 121.7 |
C10—C9B—H9BB | 109.1 | H15A—C15—H15B | 107.2 |
C3—C10—C9B | 114.0 (3) | H17A—O17—H17B | 115 (3) |
C3—C10—H10 | 121.0 | H18A—O18—H18B | 110 (2) |
C3—C10—H10A | 108.7 | ||
N1—C2—C3—C4 | −2.1 (3) | C5—C6—C15—C14A | 13.7 (7) |
N1—C2—C3—C10 | 179.00 (19) | C5—C6—C15—C14B | −1.4 (6) |
N1—C2—C7—C8A | −177.5 (4) | C5—C12—C13A—C14A | −45.4 (9) |
N1—C2—C7—C8B | 164.6 (3) | C5—C12—C13B—C14B | 4.8 (10) |
N1—C6—C15—C14A | −165.8 (6) | C6—N1—C2—C3 | 0.1 (3) |
N1—C6—C15—C14B | 179.1 (5) | C6—N1—C2—C7 | −179.78 (18) |
C2—N1—C6—C5 | 1.0 (3) | C6—C5—C12—C13A | 15.9 (5) |
C2—N1—C6—C15 | −179.49 (19) | C6—C5—C12—C13B | −2.1 (5) |
C2—C3—C4—C5 | 3.0 (3) | C7—C2—C3—C4 | 177.72 (19) |
C2—C3—C4—N11 | −176.97 (18) | C7—C2—C3—C10 | −1.2 (2) |
C2—C3—C10—C9A | 4.3 (6) | C7—C8A—C9A—C10 | 11.6 (14) |
C2—C3—C10—C9B | −13.8 (3) | C7—C8B—C9B—C10 | −60.1 (7) |
C2—C7—C8A—C9A | −8.0 (11) | C8A—C9A—C10—C3 | −8.7 (10) |
C2—C7—C8B—C9B | 44.9 (6) | C8B—C9B—C10—C3 | 46.4 (6) |
C3—C2—C7—C8A | 2.7 (4) | C10—C3—C4—C5 | −178.08 (19) |
C3—C2—C7—C8B | −15.3 (4) | C10—C3—C4—N11 | 1.9 (3) |
C3—C4—C5—C6 | −2.0 (3) | N11—C4—C5—C6 | 178.0 (2) |
C3—C4—C5—C12 | 178.16 (19) | N11—C4—C5—C12 | −1.8 (3) |
C4—C3—C10—C9A | −174.6 (5) | C12—C5—C6—N1 | 179.84 (19) |
C4—C3—C10—C9B | 167.4 (3) | C12—C5—C6—C15 | 0.4 (3) |
C4—C5—C6—N1 | 0.0 (3) | C12—C13A—C14A—C15 | 56.1 (12) |
C4—C5—C6—C15 | −179.5 (2) | C12—C13B—C14B—C15 | −6.2 (14) |
C4—C5—C12—C13A | −164.3 (4) | C13A—C14A—C15—C6 | −42.5 (12) |
C4—C5—C12—C13B | 177.8 (4) | C13B—C14B—C15—C6 | 4.2 (12) |