Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618017904/qp3016sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618017904/qp3016Promethazine_hydrochloride_succinic_acidsup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618017904/qp3016Promethazine_Hydrochloride_fumaric_acidsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618017904/qp3016Promethazine_Hydrochloride_adipic_acidsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618017904/qp3016Promethazine_hydrochloride_oxalic_acidsup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618017904/qp3016Promethazine_oxalic_acidsup6.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618017904/qp3016Promethazine_hydrochloride_succinic_acidsup7.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618017904/qp3016Promethazine_Hydrochloride_fumaric_acidsup8.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618017904/qp3016Promethazine_Hydrochloride_adipic_acidsup9.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618017904/qp3016Promethazine_hydrochloride_oxalic_acidsup10.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618017904/qp3016Promethazine_oxalic_acidsup11.cml | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229618017904/qp3016sup12.pdf |
CCDC references: 1853756; 1853755; 1853759; 1853757; 1853758
For all structures, data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for Promethazine_Hydrochloride_succinic_acid, Promethazine_hydrochloride_oxalic_acid; SHELXT (Sheldrick, 2015a) for Promethazine_Hydrochloride_fumaric_acid, Promethazine_Hydrochloride_adipic_acid, Promethazine_oxalic_acid. For all structures, program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
C17H21N2S+·Cl−·0.5C4H6O4 | F(000) = 804 |
Mr = 379.91 | Dx = 1.271 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 8.8247 (3) Å | Cell parameters from 8891 reflections |
b = 26.4201 (7) Å | θ = 5.5–71.1° |
c = 8.7393 (4) Å | µ = 2.80 mm−1 |
β = 103.070 (4)° | T = 293 K |
V = 1984.78 (12) Å3 | Needle, blue |
Z = 4 | 0.25 × 0.15 × 0.09 mm |
Agilent SuperNova Dual Source diffractometer with an Eos detector | Rint = 0.123 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | θmax = 71.1°, θmin = 5.5° |
Tmin = 0.492, Tmax = 1.000 | h = −10→10 |
11754 measured reflections | k = −32→32 |
3503 independent reflections | l = −10→8 |
3008 reflections with I > 2σ(I) |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.072 | H-atom parameters constrained |
wR(F2) = 0.214 | w = 1/[σ2(Fo2) + (0.117P)2 + 0.9442P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
3503 reflections | Δρmax = 0.63 e Å−3 |
230 parameters | Δρmin = −0.37 e Å−3 |
0 restraints |
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 | ||
Cl1 | 0.60991 (10) | 0.28893 (3) | 0.57926 (9) | 0.0550 (3) | |
S1 | 1.11147 (12) | 0.06827 (3) | 0.75956 (12) | 0.0641 (3) | |
N2 | 0.4877 (3) | 0.18028 (8) | 0.5415 (2) | 0.0343 (5) | |
H2 | 0.527041 | 0.215010 | 0.543037 | 0.041* | |
O1 | 0.6141 (4) | 0.39576 (9) | 0.4668 (3) | 0.0748 (8) | |
H1 | 0.614312 | 0.368266 | 0.510377 | 0.112* | |
N1 | 0.8953 (3) | 0.13927 (10) | 0.5586 (3) | 0.0454 (6) | |
C14 | 0.6285 (3) | 0.14657 (10) | 0.5855 (3) | 0.0354 (6) | |
H14 | 0.679744 | 0.154072 | 0.694728 | 0.042* | |
O2 | 0.5101 (5) | 0.42148 (10) | 0.6600 (3) | 0.0834 (10) | |
C11 | 0.9526 (4) | 0.21099 (12) | 0.7423 (3) | 0.0459 (7) | |
H11 | 0.879999 | 0.231054 | 0.675289 | 0.055* | |
C13 | 0.7426 (3) | 0.15987 (12) | 0.4836 (3) | 0.0414 (6) | |
H13A | 0.707373 | 0.145505 | 0.379481 | 0.050* | |
H13B | 0.749195 | 0.196317 | 0.473412 | 0.050* | |
C10 | 1.0351 (4) | 0.23054 (14) | 0.8834 (4) | 0.0530 (8) | |
H10 | 1.015404 | 0.263376 | 0.911985 | 0.064* | |
C7 | 1.0893 (3) | 0.13247 (12) | 0.8040 (3) | 0.0434 (6) | |
C12 | 0.9778 (3) | 0.16124 (11) | 0.6999 (3) | 0.0392 (6) | |
C1 | 0.9752 (4) | 0.10842 (12) | 0.4720 (4) | 0.0463 (7) | |
C6 | 1.0838 (4) | 0.07314 (12) | 0.5538 (4) | 0.0528 (8) | |
C16 | 0.3900 (4) | 0.17199 (15) | 0.3818 (4) | 0.0545 (8) | |
H16A | 0.345098 | 0.138745 | 0.375584 | 0.082* | |
H16B | 0.453034 | 0.175009 | 0.305956 | 0.082* | |
H16C | 0.308560 | 0.196833 | 0.360319 | 0.082* | |
C17 | 0.3905 (4) | 0.17832 (13) | 0.6605 (4) | 0.0523 (8) | |
H17A | 0.452784 | 0.187510 | 0.761596 | 0.078* | |
H17B | 0.351030 | 0.144629 | 0.665180 | 0.078* | |
H17C | 0.305188 | 0.201542 | 0.631448 | 0.078* | |
C9 | 1.1459 (5) | 0.20193 (15) | 0.9816 (4) | 0.0602 (9) | |
H9 | 1.202038 | 0.215610 | 1.075506 | 0.072* | |
C18 | 0.5536 (5) | 0.43033 (12) | 0.5443 (4) | 0.0522 (8) | |
C8 | 1.1740 (4) | 0.15321 (14) | 0.9416 (4) | 0.0543 (8) | |
H8 | 1.250391 | 0.134115 | 1.007428 | 0.065* | |
C2 | 0.9512 (5) | 0.11077 (15) | 0.3100 (4) | 0.0584 (9) | |
H2A | 0.882785 | 0.134550 | 0.254015 | 0.070* | |
C5 | 1.1637 (5) | 0.04138 (15) | 0.4738 (6) | 0.0706 (11) | |
H5 | 1.237117 | 0.018917 | 0.529143 | 0.085* | |
C19 | 0.5459 (5) | 0.48106 (12) | 0.4662 (4) | 0.0613 (10) | |
H19A | 0.650780 | 0.493779 | 0.476113 | 0.074* | |
H19B | 0.499512 | 0.477101 | 0.355119 | 0.074* | |
C3 | 1.0292 (6) | 0.07763 (18) | 0.2310 (5) | 0.0768 (13) | |
H3 | 1.010454 | 0.078724 | 0.122003 | 0.092* | |
C4 | 1.1348 (6) | 0.04294 (17) | 0.3135 (7) | 0.0853 (15) | |
H4 | 1.186024 | 0.020747 | 0.259685 | 0.102* | |
C15 | 0.5874 (5) | 0.09086 (13) | 0.5761 (4) | 0.0544 (8) | |
H15A | 0.543413 | 0.081833 | 0.468821 | 0.082* | |
H15B | 0.513102 | 0.084207 | 0.638641 | 0.082* | |
H15C | 0.679569 | 0.071200 | 0.614840 | 0.082* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0694 (6) | 0.0276 (4) | 0.0660 (5) | 0.0036 (3) | 0.0114 (4) | −0.0002 (3) |
S1 | 0.0647 (6) | 0.0394 (5) | 0.0856 (7) | 0.0075 (4) | 0.0111 (4) | 0.0105 (4) |
N2 | 0.0354 (12) | 0.0306 (11) | 0.0395 (11) | −0.0001 (9) | 0.0138 (8) | 0.0020 (8) |
O1 | 0.136 (3) | 0.0340 (13) | 0.0632 (15) | 0.0062 (14) | 0.0411 (15) | 0.0049 (10) |
N1 | 0.0365 (13) | 0.0562 (16) | 0.0446 (12) | 0.0085 (11) | 0.0117 (10) | −0.0086 (10) |
C14 | 0.0378 (14) | 0.0340 (14) | 0.0356 (13) | 0.0042 (10) | 0.0107 (10) | 0.0028 (9) |
O2 | 0.148 (3) | 0.0492 (15) | 0.0670 (16) | 0.0053 (17) | 0.0537 (18) | 0.0123 (12) |
C11 | 0.0453 (17) | 0.0487 (18) | 0.0464 (15) | 0.0078 (12) | 0.0159 (12) | 0.0014 (11) |
C13 | 0.0366 (15) | 0.0497 (16) | 0.0400 (14) | 0.0046 (12) | 0.0130 (10) | 0.0024 (11) |
C10 | 0.057 (2) | 0.054 (2) | 0.0517 (17) | 0.0018 (15) | 0.0196 (14) | −0.0053 (14) |
C7 | 0.0390 (15) | 0.0458 (16) | 0.0480 (15) | −0.0006 (12) | 0.0155 (11) | 0.0086 (12) |
C12 | 0.0345 (14) | 0.0478 (16) | 0.0387 (13) | 0.0030 (11) | 0.0155 (10) | 0.0007 (11) |
C1 | 0.0391 (15) | 0.0419 (17) | 0.0643 (18) | −0.0090 (12) | 0.0253 (13) | −0.0112 (13) |
C6 | 0.0448 (18) | 0.0335 (16) | 0.085 (2) | −0.0042 (13) | 0.0246 (15) | −0.0102 (14) |
C16 | 0.0483 (18) | 0.066 (2) | 0.0463 (16) | 0.0062 (15) | 0.0057 (12) | 0.0001 (14) |
C17 | 0.0502 (18) | 0.058 (2) | 0.0549 (17) | 0.0093 (15) | 0.0259 (14) | 0.0061 (14) |
C9 | 0.065 (2) | 0.063 (2) | 0.0485 (18) | −0.0054 (17) | 0.0051 (14) | −0.0029 (15) |
C18 | 0.080 (2) | 0.0317 (16) | 0.0448 (16) | −0.0096 (14) | 0.0153 (15) | 0.0019 (11) |
C8 | 0.0452 (18) | 0.066 (2) | 0.0495 (17) | 0.0019 (15) | 0.0057 (12) | 0.0130 (14) |
C2 | 0.062 (2) | 0.060 (2) | 0.062 (2) | −0.0149 (17) | 0.0332 (16) | −0.0151 (15) |
C5 | 0.058 (2) | 0.045 (2) | 0.117 (3) | −0.0021 (16) | 0.036 (2) | −0.024 (2) |
C19 | 0.106 (3) | 0.0325 (16) | 0.0534 (18) | −0.0099 (17) | 0.0343 (18) | 0.0024 (13) |
C3 | 0.087 (3) | 0.081 (3) | 0.078 (3) | −0.024 (2) | 0.052 (2) | −0.033 (2) |
C4 | 0.079 (3) | 0.059 (3) | 0.135 (4) | −0.011 (2) | 0.058 (3) | −0.040 (3) |
C15 | 0.068 (2) | 0.0356 (17) | 0.063 (2) | 0.0026 (14) | 0.0218 (16) | 0.0052 (13) |
S1—C7 | 1.761 (3) | C11—C12 | 1.397 (4) |
S1—C6 | 1.764 (4) | C10—C9 | 1.373 (5) |
N2—C14 | 1.506 (3) | C7—C12 | 1.403 (4) |
N2—C16 | 1.481 (4) | C7—C8 | 1.378 (5) |
N2—C17 | 1.491 (3) | C1—C6 | 1.410 (5) |
O1—C18 | 1.320 (4) | C1—C2 | 1.384 (5) |
N1—C13 | 1.463 (4) | C6—C5 | 1.383 (5) |
N1—C12 | 1.409 (4) | C9—C8 | 1.371 (5) |
N1—C1 | 1.406 (4) | C18—C19 | 1.499 (4) |
C14—C13 | 1.528 (4) | C2—C3 | 1.390 (5) |
C14—C15 | 1.514 (4) | C5—C4 | 1.366 (7) |
O2—C18 | 1.183 (4) | C19—C19i | 1.491 (7) |
C11—C10 | 1.382 (5) | C3—C4 | 1.387 (8) |
C7—S1—C6 | 99.07 (14) | C7—C12—N1 | 119.5 (3) |
C16—N2—C14 | 115.1 (2) | N1—C1—C6 | 118.5 (3) |
C16—N2—C17 | 110.4 (3) | C2—C1—N1 | 123.0 (3) |
C17—N2—C14 | 111.9 (2) | C2—C1—C6 | 118.5 (3) |
C12—N1—C13 | 118.7 (2) | C1—C6—S1 | 119.1 (2) |
C1—N1—C13 | 119.8 (2) | C5—C6—S1 | 120.2 (3) |
C1—N1—C12 | 119.2 (2) | C5—C6—C1 | 120.7 (4) |
N2—C14—C13 | 109.3 (2) | C8—C9—C10 | 120.1 (3) |
N2—C14—C15 | 112.8 (2) | O1—C18—C19 | 111.6 (3) |
C15—C14—C13 | 111.9 (2) | O2—C18—O1 | 123.3 (3) |
C10—C11—C12 | 120.3 (3) | O2—C18—C19 | 125.1 (3) |
N1—C13—C14 | 108.3 (2) | C9—C8—C7 | 120.2 (3) |
C9—C10—C11 | 120.6 (3) | C1—C2—C3 | 120.1 (4) |
C12—C7—S1 | 118.4 (2) | C4—C5—C6 | 120.1 (4) |
C8—C7—S1 | 120.7 (2) | C19i—C19—C18 | 113.1 (3) |
C8—C7—C12 | 120.9 (3) | C4—C3—C2 | 120.6 (4) |
C11—C12—N1 | 122.6 (3) | C5—C4—C3 | 120.0 (3) |
C11—C12—C7 | 117.9 (3) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
C17H21N2S+·Cl−·0.5C4H4O4 | F(000) = 800 |
Mr = 378.90 | Dx = 1.322 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 8.7741 (3) Å | Cell parameters from 3861 reflections |
b = 25.8762 (7) Å | θ = 3.4–71.0° |
c = 8.6007 (3) Å | µ = 2.92 mm−1 |
β = 102.920 (3)° | T = 103 K |
V = 1903.27 (11) Å3 | Plate, blue |
Z = 4 | 0.15 × 0.12 × 0.08 mm |
Agilent SuperNova Dual Source diffractometer with an Eos detector | 3024 reflections with I > 2σ(I) |
Radiation source: SuperNova (Cu) X-ray Source | Rint = 0.035 |
ω scans | θmax = 71.7°, θmin = 3.4° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | h = −10→9 |
Tmin = 0.650, Tmax = 1.000 | k = −31→31 |
9870 measured reflections | l = −9→10 |
3654 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.107 | w = 1/[σ2(Fo2) + (0.0498P)2 + 0.6635P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
3654 reflections | Δρmax = 0.39 e Å−3 |
230 parameters | Δρmin = −0.24 e Å−3 |
0 restraints |
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 | ||
Cl1 | 0.59657 (6) | 0.28887 (2) | 0.62952 (6) | 0.02544 (14) | |
S1 | 1.10822 (6) | 0.06567 (2) | 0.80625 (6) | 0.02669 (15) | |
O1 | 0.6268 (2) | 0.39570 (6) | 0.51261 (18) | 0.0343 (4) | |
H1 | 0.615569 | 0.366840 | 0.553321 | 0.051* | |
O2 | 0.4920 (2) | 0.42424 (6) | 0.68880 (19) | 0.0379 (4) | |
N2 | 0.47430 (19) | 0.17785 (6) | 0.58797 (19) | 0.0193 (4) | |
H2 | 0.513918 | 0.214093 | 0.588292 | 0.023* | |
N1 | 0.8853 (2) | 0.13716 (7) | 0.6029 (2) | 0.0231 (4) | |
C12 | 0.9677 (2) | 0.16021 (8) | 0.7469 (2) | 0.0205 (4) | |
C13 | 0.7316 (2) | 0.15772 (8) | 0.5268 (2) | 0.0219 (4) | |
H13A | 0.696148 | 0.142805 | 0.418699 | 0.026* | |
H13B | 0.737065 | 0.195745 | 0.516607 | 0.026* | |
C9 | 1.1380 (3) | 0.20322 (8) | 1.0312 (3) | 0.0275 (5) | |
H9 | 1.195651 | 0.217915 | 1.127780 | 0.033* | |
C1 | 0.9683 (2) | 0.10615 (8) | 0.5153 (2) | 0.0213 (4) | |
C14 | 0.6169 (2) | 0.14337 (8) | 0.6306 (2) | 0.0201 (4) | |
H14 | 0.669555 | 0.150391 | 0.744270 | 0.024* | |
C6 | 1.0802 (2) | 0.07126 (8) | 0.5965 (3) | 0.0232 (4) | |
C11 | 0.9401 (2) | 0.21104 (8) | 0.7884 (2) | 0.0235 (4) | |
H11 | 0.864079 | 0.231418 | 0.718821 | 0.028* | |
C8 | 1.1682 (2) | 0.15298 (8) | 0.9901 (2) | 0.0246 (5) | |
H8 | 1.248191 | 0.133448 | 1.057530 | 0.030* | |
C16 | 0.3733 (3) | 0.16873 (9) | 0.4259 (2) | 0.0251 (5) | |
H16A | 0.324335 | 0.134591 | 0.422720 | 0.038* | |
H16B | 0.437385 | 0.170248 | 0.346149 | 0.038* | |
H16C | 0.291975 | 0.195355 | 0.402487 | 0.038* | |
C10 | 1.0234 (3) | 0.23178 (8) | 0.9306 (3) | 0.0259 (5) | |
H10 | 1.001616 | 0.265988 | 0.959406 | 0.031* | |
C2 | 0.9432 (3) | 0.10878 (8) | 0.3493 (3) | 0.0254 (5) | |
H2A | 0.870865 | 0.133139 | 0.292073 | 0.030* | |
C15 | 0.5759 (3) | 0.08621 (8) | 0.6162 (3) | 0.0265 (5) | |
H15A | 0.530194 | 0.077813 | 0.504359 | 0.040* | |
H15B | 0.500270 | 0.078355 | 0.681202 | 0.040* | |
H15C | 0.670774 | 0.065638 | 0.653647 | 0.040* | |
C5 | 1.1637 (3) | 0.03982 (8) | 0.5144 (3) | 0.0287 (5) | |
H5 | 1.241319 | 0.017009 | 0.571243 | 0.034* | |
C7 | 1.0817 (2) | 0.13133 (8) | 0.8510 (2) | 0.0217 (4) | |
C19 | 0.5505 (3) | 0.48184 (8) | 0.4937 (3) | 0.0290 (5) | |
H19 | 0.623938 | 0.487866 | 0.429615 | 0.035* | |
C18 | 0.5526 (3) | 0.43161 (8) | 0.5773 (3) | 0.0291 (5) | |
C17 | 0.3800 (2) | 0.17549 (8) | 0.7126 (2) | 0.0249 (5) | |
H17A | 0.443790 | 0.187410 | 0.814777 | 0.037* | |
H17B | 0.346564 | 0.139798 | 0.723629 | 0.037* | |
H17C | 0.287802 | 0.197718 | 0.681202 | 0.037* | |
C4 | 1.1335 (3) | 0.04180 (8) | 0.3493 (3) | 0.0316 (5) | |
H4 | 1.188329 | 0.019686 | 0.292528 | 0.038* | |
C3 | 1.0230 (3) | 0.07614 (9) | 0.2672 (3) | 0.0300 (5) | |
H3 | 1.001784 | 0.077308 | 0.154042 | 0.036* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0274 (3) | 0.0233 (2) | 0.0248 (3) | 0.0006 (2) | 0.0040 (2) | −0.00080 (18) |
S1 | 0.0271 (3) | 0.0257 (3) | 0.0265 (3) | 0.0018 (2) | 0.0044 (2) | 0.0031 (2) |
O1 | 0.0505 (11) | 0.0277 (8) | 0.0265 (8) | −0.0010 (8) | 0.0122 (7) | 0.0027 (6) |
O2 | 0.0551 (11) | 0.0319 (8) | 0.0306 (9) | −0.0015 (8) | 0.0177 (8) | 0.0028 (7) |
N2 | 0.0163 (9) | 0.0252 (8) | 0.0170 (8) | 0.0006 (7) | 0.0050 (7) | 0.0021 (6) |
N1 | 0.0156 (9) | 0.0334 (9) | 0.0201 (8) | 0.0043 (7) | 0.0034 (7) | −0.0023 (7) |
C12 | 0.0159 (10) | 0.0290 (10) | 0.0188 (9) | −0.0011 (8) | 0.0084 (8) | 0.0011 (8) |
C13 | 0.0156 (10) | 0.0316 (10) | 0.0186 (9) | 0.0012 (8) | 0.0042 (8) | −0.0003 (8) |
C9 | 0.0268 (12) | 0.0354 (11) | 0.0193 (10) | −0.0046 (9) | 0.0029 (9) | −0.0012 (9) |
C1 | 0.0153 (10) | 0.0265 (10) | 0.0243 (10) | −0.0052 (8) | 0.0089 (8) | −0.0042 (8) |
C14 | 0.0150 (10) | 0.0276 (10) | 0.0178 (9) | 0.0022 (8) | 0.0038 (8) | 0.0012 (8) |
C6 | 0.0192 (11) | 0.0256 (10) | 0.0264 (10) | −0.0048 (8) | 0.0084 (9) | −0.0014 (8) |
C11 | 0.0199 (11) | 0.0306 (11) | 0.0219 (10) | 0.0031 (9) | 0.0085 (9) | 0.0030 (8) |
C8 | 0.0199 (11) | 0.0327 (11) | 0.0207 (10) | −0.0006 (9) | 0.0035 (8) | 0.0051 (8) |
C16 | 0.0211 (11) | 0.0361 (11) | 0.0174 (10) | 0.0023 (9) | 0.0026 (8) | 0.0018 (8) |
C10 | 0.0248 (12) | 0.0284 (10) | 0.0264 (11) | 0.0009 (9) | 0.0100 (9) | 0.0002 (8) |
C2 | 0.0211 (11) | 0.0326 (11) | 0.0240 (10) | −0.0049 (9) | 0.0084 (9) | −0.0019 (9) |
C15 | 0.0255 (12) | 0.0255 (10) | 0.0290 (11) | 0.0022 (9) | 0.0071 (9) | 0.0013 (8) |
C5 | 0.0231 (12) | 0.0248 (10) | 0.0397 (13) | −0.0029 (9) | 0.0101 (10) | −0.0035 (9) |
C7 | 0.0191 (10) | 0.0256 (10) | 0.0226 (10) | −0.0007 (8) | 0.0090 (8) | 0.0032 (8) |
C19 | 0.0376 (14) | 0.0278 (10) | 0.0213 (10) | −0.0090 (9) | 0.0063 (9) | −0.0014 (8) |
C18 | 0.0352 (13) | 0.0287 (11) | 0.0219 (10) | −0.0081 (10) | 0.0033 (10) | −0.0009 (9) |
C17 | 0.0201 (11) | 0.0343 (11) | 0.0224 (10) | 0.0024 (9) | 0.0095 (9) | 0.0014 (8) |
C4 | 0.0295 (13) | 0.0280 (11) | 0.0433 (14) | −0.0079 (9) | 0.0205 (11) | −0.0101 (10) |
C3 | 0.0312 (13) | 0.0345 (11) | 0.0283 (11) | −0.0084 (10) | 0.0153 (10) | −0.0069 (9) |
S1—C6 | 1.771 (2) | C11—H11 | 0.9500 |
S1—C7 | 1.769 (2) | C11—C10 | 1.385 (3) |
O1—H1 | 0.8400 | C8—H8 | 0.9500 |
O1—C18 | 1.326 (3) | C8—C7 | 1.384 (3) |
O2—C18 | 1.211 (3) | C16—H16A | 0.9800 |
N2—H2 | 1.0000 | C16—H16B | 0.9800 |
N2—C14 | 1.514 (2) | C16—H16C | 0.9800 |
N2—C16 | 1.494 (2) | C10—H10 | 0.9500 |
N2—C17 | 1.495 (2) | C2—H2A | 0.9500 |
N1—C12 | 1.418 (3) | C2—C3 | 1.386 (3) |
N1—C13 | 1.461 (3) | C15—H15A | 0.9800 |
N1—C1 | 1.409 (3) | C15—H15B | 0.9800 |
C12—C11 | 1.398 (3) | C15—H15C | 0.9800 |
C12—C7 | 1.401 (3) | C5—H5 | 0.9500 |
C13—H13A | 0.9900 | C5—C4 | 1.386 (3) |
C13—H13B | 0.9900 | C19—C19i | 1.312 (5) |
C13—C14 | 1.533 (3) | C19—H19 | 0.9500 |
C9—H9 | 0.9500 | C19—C18 | 1.483 (3) |
C9—C8 | 1.388 (3) | C17—H17A | 0.9800 |
C9—C10 | 1.385 (3) | C17—H17B | 0.9800 |
C1—C6 | 1.400 (3) | C17—H17C | 0.9800 |
C1—C2 | 1.397 (3) | C4—H4 | 0.9500 |
C14—H14 | 1.0000 | C4—C3 | 1.386 (3) |
C14—C15 | 1.521 (3) | C3—H3 | 0.9500 |
C6—C5 | 1.389 (3) | ||
C7—S1—C6 | 98.52 (9) | N2—C16—H16B | 109.5 |
C18—O1—H1 | 109.5 | N2—C16—H16C | 109.5 |
C14—N2—H2 | 106.5 | H16A—C16—H16B | 109.5 |
C16—N2—H2 | 106.5 | H16A—C16—H16C | 109.5 |
C16—N2—C14 | 114.75 (16) | H16B—C16—H16C | 109.5 |
C16—N2—C17 | 110.79 (16) | C9—C10—C11 | 120.7 (2) |
C17—N2—H2 | 106.5 | C9—C10—H10 | 119.6 |
C17—N2—C14 | 111.24 (15) | C11—C10—H10 | 119.6 |
C12—N1—C13 | 118.49 (16) | C1—C2—H2A | 119.7 |
C1—N1—C12 | 118.86 (17) | C3—C2—C1 | 120.6 (2) |
C1—N1—C13 | 120.22 (16) | C3—C2—H2A | 119.7 |
C11—C12—N1 | 122.36 (18) | C14—C15—H15A | 109.5 |
C11—C12—C7 | 118.57 (18) | C14—C15—H15B | 109.5 |
C7—C12—N1 | 119.06 (18) | C14—C15—H15C | 109.5 |
N1—C13—H13A | 110.1 | H15A—C15—H15B | 109.5 |
N1—C13—H13B | 110.1 | H15A—C15—H15C | 109.5 |
N1—C13—C14 | 108.12 (16) | H15B—C15—H15C | 109.5 |
H13A—C13—H13B | 108.4 | C6—C5—H5 | 120.1 |
C14—C13—H13A | 110.1 | C4—C5—C6 | 119.8 (2) |
C14—C13—H13B | 110.1 | C4—C5—H5 | 120.1 |
C8—C9—H9 | 120.2 | C12—C7—S1 | 118.90 (15) |
C10—C9—H9 | 120.2 | C8—C7—S1 | 120.25 (16) |
C10—C9—C8 | 119.6 (2) | C8—C7—C12 | 120.80 (19) |
C6—C1—N1 | 119.30 (18) | C19i—C19—H19 | 119.2 |
C2—C1—N1 | 122.43 (19) | C19i—C19—C18 | 121.5 (3) |
C2—C1—C6 | 118.28 (19) | C18—C19—H19 | 119.2 |
N2—C14—C13 | 109.31 (15) | O1—C18—C19 | 111.4 (2) |
N2—C14—H14 | 107.8 | O2—C18—O1 | 124.4 (2) |
N2—C14—C15 | 112.69 (16) | O2—C18—C19 | 124.2 (2) |
C13—C14—H14 | 107.8 | N2—C17—H17A | 109.5 |
C15—C14—C13 | 111.24 (17) | N2—C17—H17B | 109.5 |
C15—C14—H14 | 107.8 | N2—C17—H17C | 109.5 |
C1—C6—S1 | 118.86 (16) | H17A—C17—H17B | 109.5 |
C5—C6—S1 | 120.08 (17) | H17A—C17—H17C | 109.5 |
C5—C6—C1 | 121.0 (2) | H17B—C17—H17C | 109.5 |
C12—C11—H11 | 119.9 | C5—C4—H4 | 120.1 |
C10—C11—C12 | 120.20 (19) | C5—C4—C3 | 119.8 (2) |
C10—C11—H11 | 119.9 | C3—C4—H4 | 120.1 |
C9—C8—H8 | 120.0 | C2—C3—H3 | 119.8 |
C7—C8—C9 | 120.03 (19) | C4—C3—C2 | 120.4 (2) |
C7—C8—H8 | 120.0 | C4—C3—H3 | 119.8 |
N2—C16—H16A | 109.5 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
C17H21N2S+·Cl−·0.5C6H10O4 | F(000) = 836 |
Mr = 393.94 | Dx = 1.237 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 8.8988 (2) Å | Cell parameters from 9792 reflections |
b = 27.7992 (5) Å | θ = 5.1–71.2° |
c = 8.7933 (2) Å | µ = 2.64 mm−1 |
β = 103.484 (2)° | T = 293 K |
V = 2115.32 (8) Å3 | , blue |
Z = 4 | 0.15 × 0.12 × 0.08 mm |
Agilent SuperNova Dual Source diffractometer with an Eos detector | 3462 reflections with I > 2σ(I) |
Radiation source: SuperNova (Cu) X-ray Source | Rint = 0.040 |
ω scans | θmax = 71.8°, θmin = 5.1° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | h = −10→10 |
Tmin = 0.382, Tmax = 1.000 | k = −34→34 |
27108 measured reflections | l = −10→9 |
4096 independent reflections |
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.107 | w = 1/[σ2(Fo2) + (0.0467P)2 + 0.5031P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
4096 reflections | Δρmax = 0.19 e Å−3 |
239 parameters | Δρmin = −0.19 e Å−3 |
0 restraints |
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 | ||
Cl1 | 0.44628 (6) | 0.28738 (2) | 0.33373 (6) | 0.06918 (17) | |
S1 | 0.94831 (6) | 0.07489 (2) | 0.49504 (7) | 0.07698 (19) | |
N2 | 0.32146 (14) | 0.18535 (5) | 0.30659 (15) | 0.0440 (3) | |
H2 | 0.362428 | 0.218163 | 0.310563 | 0.053* | |
N1 | 0.72167 (15) | 0.14307 (5) | 0.31704 (17) | 0.0530 (3) | |
O2 | 0.3352 (2) | 0.40657 (5) | 0.4321 (2) | 0.0848 (5) | |
O1 | 0.4477 (2) | 0.39144 (5) | 0.23834 (17) | 0.0836 (5) | |
H1 | 0.441670 | 0.363571 | 0.266904 | 0.125* | |
C13 | 0.57043 (17) | 0.16374 (6) | 0.24667 (19) | 0.0489 (4) | |
H13A | 0.530855 | 0.150182 | 0.143441 | 0.059* | |
H13B | 0.579459 | 0.198280 | 0.236050 | 0.059* | |
C12 | 0.80875 (17) | 0.16283 (6) | 0.45869 (19) | 0.0500 (4) | |
C1 | 0.80207 (18) | 0.11806 (6) | 0.2212 (2) | 0.0516 (4) | |
C14 | 0.46027 (17) | 0.15243 (6) | 0.35155 (19) | 0.0457 (4) | |
H14 | 0.513761 | 0.160068 | 0.459394 | 0.055* | |
C11 | 0.7851 (2) | 0.20913 (7) | 0.5076 (2) | 0.0576 (4) | |
H11 | 0.709594 | 0.228479 | 0.445893 | 0.069* | |
C16 | 0.2258 (2) | 0.17847 (7) | 0.1453 (2) | 0.0601 (5) | |
H16A | 0.177478 | 0.147402 | 0.137203 | 0.090* | |
H16B | 0.290364 | 0.180590 | 0.072003 | 0.090* | |
H16C | 0.147764 | 0.202978 | 0.122503 | 0.090* | |
C7 | 0.92411 (18) | 0.13471 (7) | 0.5528 (2) | 0.0569 (4) | |
C2 | 0.7748 (2) | 0.12535 (7) | 0.0614 (2) | 0.0605 (5) | |
H2A | 0.704001 | 0.148563 | 0.013826 | 0.073* | |
C6 | 0.9139 (2) | 0.08456 (7) | 0.2912 (3) | 0.0614 (5) | |
C18 | 0.3941 (3) | 0.42064 (7) | 0.3313 (2) | 0.0652 (5) | |
C17 | 0.2246 (2) | 0.18344 (7) | 0.4233 (2) | 0.0627 (5) | |
H17A | 0.287320 | 0.190577 | 0.525255 | 0.094* | |
H17B | 0.181174 | 0.151838 | 0.423564 | 0.094* | |
H17C | 0.142894 | 0.206656 | 0.396311 | 0.094* | |
C20 | 0.4278 (2) | 0.50440 (6) | 0.4369 (3) | 0.0715 (6) | |
H20A | 0.338285 | 0.498942 | 0.479829 | 0.086* | |
H20B | 0.426005 | 0.537804 | 0.404602 | 0.086* | |
C15 | 0.4165 (2) | 0.09963 (6) | 0.3459 (2) | 0.0612 (5) | |
H15A | 0.365875 | 0.090979 | 0.240740 | 0.092* | |
H15B | 0.347968 | 0.093982 | 0.413667 | 0.092* | |
H15C | 0.508051 | 0.080498 | 0.379691 | 0.092* | |
C10 | 0.8729 (2) | 0.22666 (8) | 0.6475 (2) | 0.0680 (5) | |
H10 | 0.854116 | 0.257360 | 0.680765 | 0.082* | |
C8 | 1.0147 (2) | 0.15341 (9) | 0.6901 (2) | 0.0693 (6) | |
H8 | 1.093918 | 0.134993 | 0.750165 | 0.083* | |
C9 | 0.9878 (2) | 0.19897 (9) | 0.7375 (2) | 0.0747 (6) | |
H9 | 1.047410 | 0.211117 | 0.830742 | 0.090* | |
C5 | 0.9944 (2) | 0.05881 (8) | 0.2002 (3) | 0.0794 (7) | |
H5 | 1.070514 | 0.037054 | 0.247258 | 0.095* | |
C19 | 0.4159 (3) | 0.47275 (7) | 0.2953 (3) | 0.0842 (7) | |
H19A | 0.329326 | 0.483301 | 0.213255 | 0.101* | |
H19B | 0.509102 | 0.476140 | 0.257012 | 0.101* | |
C4 | 0.9620 (3) | 0.06538 (9) | 0.0411 (4) | 0.0881 (8) | |
H4 | 1.014376 | 0.047554 | −0.019621 | 0.106* | |
C3 | 0.8524 (3) | 0.09818 (8) | −0.0281 (3) | 0.0763 (6) | |
H3 | 0.829995 | 0.102263 | −0.136038 | 0.092* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0755 (3) | 0.0468 (2) | 0.0785 (4) | −0.00046 (19) | 0.0044 (2) | −0.0044 (2) |
S1 | 0.0645 (3) | 0.0677 (3) | 0.0961 (4) | 0.0118 (2) | 0.0134 (3) | 0.0213 (3) |
N2 | 0.0368 (6) | 0.0489 (7) | 0.0462 (8) | −0.0008 (5) | 0.0093 (5) | −0.0009 (5) |
N1 | 0.0380 (7) | 0.0696 (9) | 0.0502 (8) | 0.0073 (6) | 0.0077 (6) | −0.0045 (7) |
O2 | 0.1136 (13) | 0.0628 (8) | 0.0843 (11) | −0.0212 (8) | 0.0360 (10) | −0.0067 (8) |
O1 | 0.1309 (14) | 0.0591 (8) | 0.0632 (9) | −0.0057 (9) | 0.0277 (9) | 0.0007 (7) |
C13 | 0.0365 (7) | 0.0639 (10) | 0.0449 (9) | 0.0018 (7) | 0.0063 (6) | 0.0001 (7) |
C12 | 0.0343 (7) | 0.0686 (10) | 0.0485 (9) | −0.0002 (7) | 0.0120 (7) | 0.0038 (8) |
C1 | 0.0407 (8) | 0.0528 (9) | 0.0646 (11) | −0.0067 (7) | 0.0187 (7) | −0.0068 (8) |
C14 | 0.0374 (7) | 0.0544 (9) | 0.0434 (9) | 0.0021 (6) | 0.0055 (6) | 0.0008 (7) |
C11 | 0.0450 (9) | 0.0728 (11) | 0.0531 (10) | 0.0033 (8) | 0.0076 (8) | −0.0026 (8) |
C16 | 0.0483 (9) | 0.0759 (12) | 0.0507 (10) | 0.0073 (8) | 0.0008 (8) | 0.0002 (9) |
C7 | 0.0393 (8) | 0.0738 (11) | 0.0579 (11) | 0.0007 (7) | 0.0120 (7) | 0.0135 (9) |
C2 | 0.0587 (10) | 0.0638 (11) | 0.0645 (12) | −0.0130 (8) | 0.0255 (9) | −0.0078 (9) |
C6 | 0.0467 (9) | 0.0534 (9) | 0.0869 (14) | −0.0036 (7) | 0.0211 (9) | −0.0037 (9) |
C18 | 0.0825 (13) | 0.0546 (10) | 0.0516 (11) | −0.0104 (9) | 0.0014 (10) | −0.0027 (9) |
C17 | 0.0524 (9) | 0.0794 (12) | 0.0612 (12) | 0.0075 (9) | 0.0229 (8) | 0.0019 (9) |
C20 | 0.0741 (12) | 0.0430 (9) | 0.0906 (15) | 0.0047 (8) | 0.0055 (11) | −0.0010 (9) |
C15 | 0.0624 (11) | 0.0535 (10) | 0.0688 (12) | 0.0025 (8) | 0.0174 (9) | 0.0063 (8) |
C10 | 0.0599 (11) | 0.0827 (13) | 0.0602 (12) | −0.0055 (9) | 0.0114 (9) | −0.0077 (10) |
C8 | 0.0436 (9) | 0.0986 (16) | 0.0614 (12) | −0.0012 (9) | 0.0037 (8) | 0.0230 (11) |
C9 | 0.0629 (12) | 0.1030 (17) | 0.0514 (12) | −0.0142 (11) | −0.0006 (9) | −0.0023 (11) |
C5 | 0.0576 (11) | 0.0587 (11) | 0.128 (2) | −0.0012 (9) | 0.0349 (13) | −0.0164 (13) |
C19 | 0.1172 (19) | 0.0547 (11) | 0.0731 (14) | −0.0102 (11) | 0.0067 (13) | 0.0070 (10) |
C4 | 0.0774 (15) | 0.0794 (15) | 0.125 (2) | −0.0174 (12) | 0.0586 (16) | −0.0402 (15) |
C3 | 0.0791 (14) | 0.0814 (14) | 0.0811 (15) | −0.0243 (12) | 0.0442 (12) | −0.0229 (12) |
S1—C7 | 1.766 (2) | C2—H2A | 0.9300 |
S1—C6 | 1.767 (2) | C2—C3 | 1.386 (3) |
N2—H2 | 0.9800 | C6—C5 | 1.391 (3) |
N2—C14 | 1.5138 (19) | C18—C19 | 1.505 (3) |
N2—C16 | 1.487 (2) | C17—H17A | 0.9600 |
N2—C17 | 1.487 (2) | C17—H17B | 0.9600 |
N1—C13 | 1.4614 (19) | C17—H17C | 0.9600 |
N1—C12 | 1.415 (2) | C20—C20i | 1.509 (4) |
N1—C1 | 1.409 (2) | C20—H20A | 0.9700 |
O2—C18 | 1.196 (2) | C20—H20B | 0.9700 |
O1—H1 | 0.8200 | C20—C19 | 1.508 (3) |
O1—C18 | 1.317 (3) | C15—H15A | 0.9600 |
C13—H13A | 0.9700 | C15—H15B | 0.9600 |
C13—H13B | 0.9700 | C15—H15C | 0.9600 |
C13—C14 | 1.527 (2) | C10—H10 | 0.9300 |
C12—C11 | 1.388 (3) | C10—C9 | 1.374 (3) |
C12—C7 | 1.398 (2) | C8—H8 | 0.9300 |
C1—C2 | 1.385 (3) | C8—C9 | 1.372 (3) |
C1—C6 | 1.397 (3) | C9—H9 | 0.9300 |
C14—H14 | 0.9800 | C5—H5 | 0.9300 |
C14—C15 | 1.516 (2) | C5—C4 | 1.373 (4) |
C11—H11 | 0.9300 | C19—H19A | 0.9700 |
C11—C10 | 1.383 (3) | C19—H19B | 0.9700 |
C16—H16A | 0.9600 | C4—H4 | 0.9300 |
C16—H16B | 0.9600 | C4—C3 | 1.369 (4) |
C16—H16C | 0.9600 | C3—H3 | 0.9300 |
C7—C8 | 1.387 (3) | ||
C7—S1—C6 | 98.30 (9) | C5—C6—C1 | 119.9 (2) |
C14—N2—H2 | 106.2 | O2—C18—O1 | 122.87 (18) |
C16—N2—H2 | 106.2 | O2—C18—C19 | 124.8 (2) |
C16—N2—C14 | 114.98 (13) | O1—C18—C19 | 112.4 (2) |
C17—N2—H2 | 106.2 | N2—C17—H17A | 109.5 |
C17—N2—C14 | 111.53 (13) | N2—C17—H17B | 109.5 |
C17—N2—C16 | 111.02 (13) | N2—C17—H17C | 109.5 |
C12—N1—C13 | 118.76 (14) | H17A—C17—H17B | 109.5 |
C1—N1—C13 | 119.11 (14) | H17A—C17—H17C | 109.5 |
C1—N1—C12 | 117.87 (13) | H17B—C17—H17C | 109.5 |
C18—O1—H1 | 109.5 | C20i—C20—H20A | 108.9 |
N1—C13—H13A | 109.9 | C20i—C20—H20B | 108.9 |
N1—C13—H13B | 109.9 | H20A—C20—H20B | 107.7 |
N1—C13—C14 | 108.72 (13) | C19—C20—C20i | 113.4 (2) |
H13A—C13—H13B | 108.3 | C19—C20—H20A | 108.9 |
C14—C13—H13A | 109.9 | C19—C20—H20B | 108.9 |
C14—C13—H13B | 109.9 | C14—C15—H15A | 109.5 |
C11—C12—N1 | 122.74 (15) | C14—C15—H15B | 109.5 |
C11—C12—C7 | 118.60 (16) | C14—C15—H15C | 109.5 |
C7—C12—N1 | 118.66 (16) | H15A—C15—H15B | 109.5 |
C2—C1—N1 | 122.77 (16) | H15A—C15—H15C | 109.5 |
C2—C1—C6 | 118.91 (17) | H15B—C15—H15C | 109.5 |
C6—C1—N1 | 118.31 (17) | C11—C10—H10 | 119.8 |
N2—C14—C13 | 108.51 (12) | C9—C10—C11 | 120.4 (2) |
N2—C14—H14 | 107.7 | C9—C10—H10 | 119.8 |
N2—C14—C15 | 112.89 (13) | C7—C8—H8 | 119.9 |
C13—C14—H14 | 107.7 | C9—C8—C7 | 120.24 (18) |
C15—C14—C13 | 112.05 (15) | C9—C8—H8 | 119.9 |
C15—C14—H14 | 107.7 | C10—C9—H9 | 120.0 |
C12—C11—H11 | 119.8 | C8—C9—C10 | 120.08 (19) |
C10—C11—C12 | 120.46 (17) | C8—C9—H9 | 120.0 |
C10—C11—H11 | 119.8 | C6—C5—H5 | 119.9 |
N2—C16—H16A | 109.5 | C4—C5—C6 | 120.2 (2) |
N2—C16—H16B | 109.5 | C4—C5—H5 | 119.9 |
N2—C16—H16C | 109.5 | C18—C19—C20 | 112.10 (19) |
H16A—C16—H16B | 109.5 | C18—C19—H19A | 109.2 |
H16A—C16—H16C | 109.5 | C18—C19—H19B | 109.2 |
H16B—C16—H16C | 109.5 | C20—C19—H19A | 109.2 |
C12—C7—S1 | 118.58 (14) | C20—C19—H19B | 109.2 |
C8—C7—S1 | 121.20 (15) | H19A—C19—H19B | 107.9 |
C8—C7—C12 | 120.20 (19) | C5—C4—H4 | 120.0 |
C1—C2—H2A | 119.9 | C3—C4—C5 | 120.0 (2) |
C1—C2—C3 | 120.3 (2) | C3—C4—H4 | 120.0 |
C3—C2—H2A | 119.9 | C2—C3—H3 | 119.7 |
C1—C6—S1 | 119.05 (15) | C4—C3—C2 | 120.5 (2) |
C5—C6—S1 | 120.99 (17) | C4—C3—H3 | 119.7 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
C17H21N2S+·Cl−·0.5C2H2O4 | F(000) = 772 |
Mr = 365.88 | Dx = 1.317 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54184 Å |
a = 10.5507 (2) Å | Cell parameters from 6477 reflections |
b = 12.4382 (2) Å | θ = 4.8–71.4° |
c = 14.2966 (3) Å | µ = 2.99 mm−1 |
β = 100.445 (2)° | T = 293 K |
V = 1845.07 (6) Å3 | Needle, blue |
Z = 4 | 0.18 × 0.12 × 0.09 mm |
Agilent SuperNova Dual Source diffractometer with an Eos detector | 3553 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 3141 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.030 |
Detector resolution: 16.4335 pixels mm-1 | θmax = 71.7°, θmin = 4.8° |
ω scans | h = −12→12 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −15→13 |
Tmin = 0.509, Tmax = 1.000 | l = −17→17 |
11908 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.106 | w = 1/[σ2(Fo2) + (0.0567P)2 + 0.3606P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
3553 reflections | Δρmax = 0.20 e Å−3 |
221 parameters | Δρmin = −0.24 e Å−3 |
0 restraints |
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 | ||
S1 | 0.17289 (4) | 0.37234 (4) | 0.77764 (4) | 0.05370 (15) | |
Cl1 | 0.85455 (4) | 0.18951 (3) | 0.86263 (4) | 0.05885 (16) | |
O2 | 0.87922 (14) | 0.49022 (12) | 0.90055 (11) | 0.0714 (4) | |
O1 | 0.99405 (13) | 0.36170 (10) | 0.98464 (10) | 0.0600 (3) | |
H1 | 0.952028 | 0.321640 | 0.945182 | 0.090* | |
C23 | 0.96065 (16) | 0.46088 (14) | 0.96455 (12) | 0.0487 (4) | |
N2 | 0.73117 (12) | 0.32421 (11) | 0.69149 (10) | 0.0438 (3) | |
H2 | 0.775663 | 0.293675 | 0.751757 | 0.053* | |
C12 | 0.40787 (16) | 0.28161 (13) | 0.83942 (12) | 0.0435 (4) | |
C8 | 0.22302 (19) | 0.17228 (15) | 0.85677 (14) | 0.0534 (4) | |
H8 | 0.134426 | 0.164892 | 0.852399 | 0.064* | |
C14 | 0.59092 (15) | 0.33522 (13) | 0.70043 (13) | 0.0437 (4) | |
H14 | 0.555325 | 0.262741 | 0.703067 | 0.052* | |
N1 | 0.45497 (13) | 0.38238 (11) | 0.81514 (11) | 0.0478 (3) | |
C13 | 0.58518 (16) | 0.39083 (14) | 0.79444 (14) | 0.0493 (4) | |
H13A | 0.646074 | 0.357476 | 0.845105 | 0.059* | |
H13B | 0.608516 | 0.465939 | 0.790709 | 0.059* | |
C7 | 0.27428 (16) | 0.26792 (13) | 0.83011 (12) | 0.0438 (4) | |
C15 | 0.51231 (18) | 0.39273 (17) | 0.61643 (15) | 0.0606 (5) | |
H15A | 0.543412 | 0.464983 | 0.613683 | 0.091* | |
H15B | 0.423488 | 0.394220 | 0.623299 | 0.091* | |
H15C | 0.520057 | 0.355532 | 0.558894 | 0.091* | |
C11 | 0.48807 (18) | 0.19563 (14) | 0.87202 (14) | 0.0527 (4) | |
H11 | 0.576897 | 0.202459 | 0.877524 | 0.063* | |
C9 | 0.3044 (2) | 0.08817 (16) | 0.88983 (14) | 0.0604 (5) | |
H9 | 0.270776 | 0.023809 | 0.907705 | 0.072* | |
C6 | 0.26394 (16) | 0.48118 (14) | 0.83323 (12) | 0.0458 (4) | |
C16 | 0.79806 (18) | 0.42697 (16) | 0.67845 (15) | 0.0570 (5) | |
H16A | 0.763582 | 0.456498 | 0.617070 | 0.068* | |
H16B | 0.888595 | 0.413736 | 0.682867 | 0.068* | |
H16C | 0.785169 | 0.476978 | 0.727015 | 0.068* | |
C1 | 0.39784 (16) | 0.47542 (13) | 0.84641 (12) | 0.0441 (4) | |
C2 | 0.46968 (19) | 0.56137 (15) | 0.89011 (13) | 0.0539 (4) | |
H2A | 0.559215 | 0.557865 | 0.901962 | 0.065* | |
C5 | 0.2042 (2) | 0.57208 (16) | 0.86070 (14) | 0.0574 (5) | |
H5 | 0.114733 | 0.575236 | 0.851628 | 0.069* | |
C17 | 0.7489 (2) | 0.24600 (17) | 0.61607 (17) | 0.0683 (6) | |
H17A | 0.712318 | 0.274888 | 0.554843 | 0.082* | |
H17B | 0.706537 | 0.179698 | 0.625818 | 0.082* | |
H17C | 0.839178 | 0.232986 | 0.618913 | 0.082* | |
C4 | 0.2764 (2) | 0.65759 (16) | 0.90128 (16) | 0.0665 (6) | |
H4 | 0.235998 | 0.718961 | 0.918676 | 0.080* | |
C10 | 0.4355 (2) | 0.09994 (16) | 0.89624 (14) | 0.0596 (5) | |
H10 | 0.489707 | 0.042507 | 0.917224 | 0.072* | |
C3 | 0.4083 (2) | 0.65207 (16) | 0.91600 (15) | 0.0637 (5) | |
H3 | 0.457066 | 0.709897 | 0.943679 | 0.076* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0404 (2) | 0.0532 (3) | 0.0652 (3) | 0.00064 (17) | 0.00346 (19) | 0.0010 (2) |
Cl1 | 0.0585 (3) | 0.0352 (2) | 0.0737 (3) | 0.00148 (16) | −0.0121 (2) | 0.00359 (18) |
O2 | 0.0736 (9) | 0.0577 (8) | 0.0685 (9) | −0.0051 (7) | −0.0253 (7) | 0.0013 (7) |
O1 | 0.0616 (8) | 0.0484 (7) | 0.0622 (8) | 0.0005 (6) | −0.0094 (6) | −0.0054 (6) |
C23 | 0.0464 (9) | 0.0492 (10) | 0.0479 (9) | −0.0054 (7) | 0.0013 (7) | −0.0001 (8) |
N2 | 0.0385 (7) | 0.0428 (7) | 0.0495 (8) | 0.0038 (5) | 0.0063 (6) | 0.0052 (6) |
C12 | 0.0439 (8) | 0.0412 (8) | 0.0451 (9) | −0.0013 (6) | 0.0068 (7) | −0.0069 (7) |
C8 | 0.0585 (10) | 0.0503 (10) | 0.0538 (10) | −0.0102 (8) | 0.0166 (8) | −0.0063 (8) |
C14 | 0.0365 (7) | 0.0371 (8) | 0.0562 (10) | −0.0033 (6) | 0.0053 (7) | −0.0022 (7) |
N1 | 0.0393 (7) | 0.0411 (7) | 0.0647 (9) | −0.0039 (5) | 0.0136 (6) | −0.0081 (6) |
C13 | 0.0386 (8) | 0.0480 (9) | 0.0613 (11) | −0.0064 (7) | 0.0091 (7) | −0.0113 (8) |
C7 | 0.0455 (8) | 0.0432 (9) | 0.0432 (9) | −0.0026 (7) | 0.0094 (7) | −0.0040 (7) |
C15 | 0.0480 (10) | 0.0602 (11) | 0.0664 (12) | 0.0049 (8) | −0.0088 (9) | 0.0005 (9) |
C11 | 0.0515 (10) | 0.0497 (10) | 0.0547 (10) | 0.0048 (7) | 0.0039 (8) | −0.0066 (8) |
C9 | 0.0863 (14) | 0.0431 (10) | 0.0552 (11) | −0.0074 (9) | 0.0224 (10) | −0.0008 (8) |
C6 | 0.0510 (9) | 0.0438 (9) | 0.0448 (9) | 0.0023 (7) | 0.0141 (7) | 0.0030 (7) |
C16 | 0.0489 (9) | 0.0522 (10) | 0.0691 (12) | −0.0089 (8) | 0.0086 (9) | 0.0017 (9) |
C1 | 0.0507 (9) | 0.0395 (8) | 0.0432 (8) | −0.0011 (7) | 0.0118 (7) | −0.0006 (7) |
C2 | 0.0616 (11) | 0.0476 (10) | 0.0533 (10) | −0.0092 (8) | 0.0125 (8) | −0.0048 (8) |
C5 | 0.0635 (11) | 0.0523 (10) | 0.0617 (11) | 0.0124 (8) | 0.0256 (9) | 0.0081 (9) |
C17 | 0.0751 (13) | 0.0545 (11) | 0.0797 (14) | 0.0052 (10) | 0.0259 (11) | −0.0104 (10) |
C4 | 0.0934 (16) | 0.0454 (10) | 0.0689 (13) | 0.0117 (10) | 0.0368 (12) | −0.0002 (9) |
C10 | 0.0789 (13) | 0.0462 (10) | 0.0522 (11) | 0.0118 (9) | 0.0078 (9) | −0.0006 (8) |
C3 | 0.0928 (15) | 0.0443 (10) | 0.0576 (12) | −0.0093 (10) | 0.0233 (11) | −0.0088 (8) |
S1—C7 | 1.7615 (18) | C14—C13 | 1.522 (2) |
S1—C6 | 1.7636 (18) | C14—C15 | 1.510 (2) |
O2—C23 | 1.193 (2) | N1—C13 | 1.461 (2) |
O1—C23 | 1.301 (2) | N1—C1 | 1.414 (2) |
C23—C23i | 1.536 (3) | C11—C10 | 1.383 (3) |
N2—C14 | 1.514 (2) | C9—C10 | 1.378 (3) |
N2—C16 | 1.488 (2) | C6—C1 | 1.393 (2) |
N2—C17 | 1.489 (2) | C6—C5 | 1.386 (2) |
C12—N1 | 1.415 (2) | C1—C2 | 1.391 (2) |
C12—C7 | 1.402 (2) | C2—C3 | 1.384 (3) |
C12—C11 | 1.391 (2) | C5—C4 | 1.374 (3) |
C8—C7 | 1.388 (2) | C4—C3 | 1.371 (3) |
C8—C9 | 1.381 (3) | ||
C7—S1—C6 | 97.75 (8) | N1—C13—C14 | 109.61 (13) |
O2—C23—O1 | 126.02 (17) | C12—C7—S1 | 118.26 (13) |
O2—C23—C23i | 122.7 (2) | C8—C7—S1 | 120.79 (13) |
O1—C23—C23i | 111.27 (18) | C8—C7—C12 | 120.86 (16) |
C16—N2—C14 | 115.20 (13) | C10—C11—C12 | 119.90 (18) |
C16—N2—C17 | 110.24 (15) | C10—C9—C8 | 119.78 (18) |
C17—N2—C14 | 111.90 (14) | C1—C6—S1 | 118.54 (13) |
C7—C12—N1 | 118.44 (15) | C5—C6—S1 | 121.03 (14) |
C11—C12—N1 | 122.97 (15) | C5—C6—C1 | 120.40 (17) |
C11—C12—C7 | 118.59 (16) | C6—C1—N1 | 118.64 (15) |
C9—C8—C7 | 119.60 (18) | C2—C1—N1 | 122.81 (15) |
N2—C14—C13 | 108.15 (13) | C2—C1—C6 | 118.55 (16) |
C15—C14—N2 | 112.33 (15) | C3—C2—C1 | 120.20 (18) |
C15—C14—C13 | 112.51 (15) | C4—C5—C6 | 120.35 (19) |
C12—N1—C13 | 119.91 (14) | C3—C4—C5 | 119.72 (18) |
C1—N1—C12 | 117.30 (13) | C9—C10—C11 | 121.20 (18) |
C1—N1—C13 | 118.40 (13) | C4—C3—C2 | 120.73 (19) |
Symmetry code: (i) −x+2, −y+1, −z+2. |
2C17H21N2S+·2C2HO4− | Z = 2 |
Mr = 748.89 | F(000) = 792 |
Triclinic, P1 | Dx = 1.365 Mg m−3 Dm = Mg m−3 Dm measured by ? |
a = 8.6840 (5) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 11.3871 (5) Å | Cell parameters from 4341 reflections |
c = 20.0923 (11) Å | θ = 4.3–70.7° |
α = 104.106 (4)° | µ = 1.81 mm−1 |
β = 90.386 (4)° | T = 293 K |
γ = 108.340 (5)° | Needle, transparent |
V = 1821.53 (18) Å3 | 0.22 × 0.11 × 0.1 mm |
Agilent SuperNova Dual Source diffractometer with an Eos detector | 6793 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 5440 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.026 |
Detector resolution: 16.4335 pixels mm-1 | θmax = 71.6°, θmin = 4.3° |
ω scans | h = −9→10 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −12→13 |
Tmin = 0.895, Tmax = 1.000 | l = −24→20 |
11276 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.057 | H-atom parameters constrained |
wR(F2) = 0.185 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.23 | (Δ/σ)max = 0.001 |
6793 reflections | Δρmax = 1.00 e Å−3 |
477 parameters | Δρmin = −0.42 e Å−3 |
0 restraints |
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 | ||
S1B | 0.97430 (11) | 0.96690 (7) | 0.58855 (3) | 0.0687 (3) | |
S1A | 0.82546 (11) | 0.40289 (8) | 0.56984 (4) | 0.0703 (3) | |
O2B | 0.19593 (18) | 1.04776 (15) | 0.93869 (9) | 0.0439 (4) | |
O1B | 0.42893 (19) | 1.01721 (15) | 0.90748 (10) | 0.0471 (4) | |
H1B | 0.382914 | 0.944907 | 0.911717 | 0.071* | |
O2A | 0.3068 (2) | 0.78397 (15) | 0.91353 (10) | 0.0497 (4) | |
O3A | 0.42181 (19) | 0.51367 (15) | 0.90215 (10) | 0.0479 (4) | |
H3AA | 0.381270 | 0.444852 | 0.911507 | 0.072* | |
O4B | 0.31512 (19) | 1.28856 (15) | 0.91957 (9) | 0.0467 (4) | |
O4A | 0.1871 (2) | 0.54174 (16) | 0.93114 (10) | 0.0534 (5) | |
O3B | 0.5421 (2) | 1.24838 (16) | 0.88825 (11) | 0.0577 (5) | |
N2B | 0.7903 (2) | 1.14612 (15) | 0.88770 (8) | 0.0311 (4) | |
H2B | 0.681017 | 1.153808 | 0.887620 | 0.037* | |
O1A | 0.5328 (2) | 0.74270 (16) | 0.88098 (12) | 0.0589 (5) | |
N2A | 0.7746 (2) | 0.63505 (16) | 0.87797 (9) | 0.0355 (4) | |
H2A | 0.667376 | 0.646549 | 0.880752 | 0.043* | |
N1B | 1.0196 (2) | 1.04383 (18) | 0.73884 (9) | 0.0407 (4) | |
N1A | 0.6499 (3) | 0.4486 (3) | 0.69302 (11) | 0.0618 (6) | |
C19B | 0.4052 (2) | 1.22047 (18) | 0.90890 (11) | 0.0334 (4) | |
C18A | 0.3961 (2) | 0.71538 (18) | 0.90168 (11) | 0.0330 (4) | |
C18B | 0.3311 (2) | 1.08540 (18) | 0.92130 (10) | 0.0312 (4) | |
C19A | 0.3215 (2) | 0.57939 (18) | 0.91367 (10) | 0.0307 (4) | |
C12B | 1.0747 (3) | 1.1501 (2) | 0.70979 (11) | 0.0382 (5) | |
C16B | 0.7939 (3) | 1.0610 (2) | 0.93324 (11) | 0.0378 (5) | |
H16A | 0.719396 | 0.976596 | 0.913164 | 0.057* | |
H16B | 0.762527 | 1.094713 | 0.977715 | 0.057* | |
H16C | 0.902040 | 1.057052 | 0.938145 | 0.057* | |
C14B | 0.8162 (3) | 1.0937 (2) | 0.81341 (10) | 0.0354 (4) | |
H14B | 0.824310 | 1.160371 | 0.789393 | 0.043* | |
C13B | 0.9777 (3) | 1.0654 (2) | 0.80955 (11) | 0.0381 (5) | |
H13A | 1.063143 | 1.137152 | 0.838722 | 0.046* | |
H13B | 0.967596 | 0.990127 | 0.825911 | 0.046* | |
C11B | 1.1375 (3) | 1.2753 (2) | 0.74931 (12) | 0.0443 (5) | |
H11B | 1.143384 | 1.292908 | 0.797131 | 0.053* | |
C1B | 1.0732 (3) | 0.9385 (2) | 0.71044 (11) | 0.0392 (5) | |
C2B | 1.1428 (3) | 0.8814 (2) | 0.75070 (14) | 0.0488 (6) | |
H2BA | 1.156898 | 0.912882 | 0.798384 | 0.059* | |
C17B | 0.9061 (3) | 1.2767 (2) | 0.91853 (13) | 0.0458 (5) | |
H17A | 0.868562 | 1.314390 | 0.960638 | 0.069* | |
H17B | 0.912886 | 1.328671 | 0.886864 | 0.069* | |
H17C | 1.011840 | 1.271246 | 0.928024 | 0.069* | |
C7B | 1.0655 (3) | 1.1262 (2) | 0.63819 (12) | 0.0494 (6) | |
C6B | 1.0579 (3) | 0.8915 (2) | 0.63926 (12) | 0.0485 (6) | |
C10B | 1.1919 (3) | 1.3751 (2) | 0.71754 (14) | 0.0520 (6) | |
H10B | 1.233228 | 1.459086 | 0.744368 | 0.062* | |
C15B | 0.6729 (3) | 0.9784 (3) | 0.77851 (13) | 0.0569 (7) | |
H15A | 0.665304 | 0.909808 | 0.799526 | 0.085* | |
H15B | 0.687466 | 0.951768 | 0.730499 | 0.085* | |
H15C | 0.574683 | 1.000268 | 0.783275 | 0.085* | |
C17A | 0.7841 (3) | 0.5552 (2) | 0.92464 (14) | 0.0481 (6) | |
H17D | 0.892810 | 0.551740 | 0.928209 | 0.072* | |
H17E | 0.709068 | 0.470227 | 0.906680 | 0.072* | |
H17F | 0.756737 | 0.591771 | 0.969410 | 0.072* | |
C16A | 0.8994 (3) | 0.7649 (2) | 0.90414 (15) | 0.0525 (6) | |
H16D | 0.878137 | 0.803922 | 0.949585 | 0.079* | |
H16E | 0.894213 | 0.817364 | 0.873910 | 0.079* | |
H16F | 1.005943 | 0.756602 | 0.905699 | 0.079* | |
C12A | 0.6205 (3) | 0.3186 (3) | 0.66280 (13) | 0.0543 (6) | |
C1A | 0.6468 (3) | 0.5297 (3) | 0.64939 (15) | 0.0572 (7) | |
C3B | 1.1912 (4) | 0.7772 (3) | 0.71952 (18) | 0.0633 (7) | |
H3B | 1.237568 | 0.739398 | 0.746635 | 0.076* | |
C15A | 0.9371 (4) | 0.5376 (3) | 0.79170 (14) | 0.0612 (7) | |
H15D | 1.028501 | 0.596844 | 0.822541 | 0.092* | |
H15E | 0.964245 | 0.530884 | 0.744988 | 0.092* | |
H15F | 0.910315 | 0.455072 | 0.801004 | 0.092* | |
C7A | 0.6940 (4) | 0.2827 (3) | 0.60301 (15) | 0.0589 (7) | |
C8B | 1.1243 (4) | 1.2265 (3) | 0.60721 (15) | 0.0626 (7) | |
H8B | 1.122422 | 1.209528 | 0.559479 | 0.075* | |
C5B | 1.1074 (4) | 0.7879 (3) | 0.60905 (15) | 0.0640 (8) | |
H5B | 1.097267 | 0.757633 | 0.561321 | 0.077* | |
C6A | 0.7163 (3) | 0.5112 (3) | 0.58675 (14) | 0.0578 (7) | |
C9B | 1.1852 (4) | 1.3505 (3) | 0.64699 (16) | 0.0648 (8) | |
H9B | 1.221746 | 1.417710 | 0.626202 | 0.078* | |
C14A | 0.7934 (3) | 0.5848 (3) | 0.80198 (13) | 0.0563 (7) | |
H14A | 0.814802 | 0.657354 | 0.781357 | 0.068* | |
C4B | 1.1714 (4) | 0.7294 (3) | 0.64929 (19) | 0.0740 (10) | |
H4B | 1.201078 | 0.658011 | 0.628991 | 0.089* | |
C13A | 0.6377 (4) | 0.4887 (4) | 0.76703 (14) | 0.0736 (9) | |
H13C | 0.611911 | 0.414773 | 0.785945 | 0.088* | |
H13D | 0.550511 | 0.525249 | 0.775184 | 0.088* | |
C11A | 0.5182 (4) | 0.2165 (4) | 0.68841 (17) | 0.0734 (9) | |
H11A | 0.466184 | 0.235444 | 0.727960 | 0.088* | |
C2A | 0.5751 (4) | 0.6250 (3) | 0.6662 (2) | 0.0790 (10) | |
H2AA | 0.529043 | 0.639530 | 0.707769 | 0.095* | |
C10A | 0.4962 (4) | 0.0914 (3) | 0.6553 (2) | 0.0789 (10) | |
H10A | 0.430058 | 0.026914 | 0.673278 | 0.095* | |
C5A | 0.7074 (5) | 0.5821 (3) | 0.54073 (19) | 0.0790 (10) | |
H5A | 0.749891 | 0.566568 | 0.498346 | 0.095* | |
C8A | 0.6663 (5) | 0.1546 (3) | 0.5713 (2) | 0.0806 (10) | |
H8A | 0.715640 | 0.132744 | 0.531355 | 0.097* | |
C4A | 0.6348 (5) | 0.6761 (4) | 0.5582 (3) | 0.0947 (13) | |
H4A | 0.628280 | 0.724159 | 0.527529 | 0.114* | |
C3A | 0.5728 (5) | 0.6983 (4) | 0.6205 (3) | 0.0999 (15) | |
H3A | 0.527939 | 0.763912 | 0.632624 | 0.120* | |
C9A | 0.5680 (5) | 0.0588 (4) | 0.5973 (2) | 0.0931 (12) | |
H9A | 0.551061 | −0.026725 | 0.575371 | 0.112* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1B | 0.0967 (6) | 0.0547 (4) | 0.0380 (3) | 0.0058 (4) | −0.0094 (3) | 0.0066 (3) |
S1A | 0.0857 (6) | 0.0639 (5) | 0.0618 (4) | 0.0272 (4) | 0.0341 (4) | 0.0124 (3) |
O2B | 0.0373 (8) | 0.0398 (9) | 0.0642 (10) | 0.0158 (7) | 0.0172 (7) | 0.0266 (8) |
O1B | 0.0397 (8) | 0.0285 (8) | 0.0839 (12) | 0.0180 (7) | 0.0210 (8) | 0.0245 (8) |
O2A | 0.0461 (9) | 0.0301 (8) | 0.0832 (12) | 0.0211 (7) | 0.0220 (8) | 0.0212 (8) |
O3A | 0.0420 (9) | 0.0300 (8) | 0.0828 (12) | 0.0187 (7) | 0.0238 (8) | 0.0252 (8) |
O4B | 0.0415 (9) | 0.0303 (8) | 0.0771 (12) | 0.0185 (7) | 0.0167 (8) | 0.0205 (7) |
O4A | 0.0374 (9) | 0.0398 (9) | 0.0914 (14) | 0.0146 (7) | 0.0235 (8) | 0.0290 (9) |
O3B | 0.0388 (9) | 0.0360 (9) | 0.1123 (16) | 0.0174 (7) | 0.0270 (9) | 0.0371 (10) |
N2B | 0.0301 (8) | 0.0282 (8) | 0.0380 (9) | 0.0126 (7) | 0.0087 (6) | 0.0099 (7) |
O1A | 0.0412 (9) | 0.0359 (9) | 0.1141 (16) | 0.0190 (8) | 0.0317 (10) | 0.0367 (10) |
N2A | 0.0315 (9) | 0.0352 (9) | 0.0414 (9) | 0.0150 (7) | 0.0065 (7) | 0.0072 (7) |
N1B | 0.0532 (11) | 0.0388 (10) | 0.0356 (9) | 0.0201 (9) | 0.0152 (8) | 0.0126 (7) |
N1A | 0.0602 (14) | 0.0770 (16) | 0.0393 (11) | 0.0200 (12) | 0.0082 (9) | 0.0022 (11) |
C19B | 0.0314 (10) | 0.0231 (10) | 0.0464 (11) | 0.0096 (8) | 0.0034 (8) | 0.0091 (8) |
C18A | 0.0326 (10) | 0.0244 (10) | 0.0441 (11) | 0.0113 (8) | 0.0061 (8) | 0.0100 (8) |
C18B | 0.0305 (10) | 0.0266 (10) | 0.0396 (10) | 0.0113 (8) | 0.0040 (8) | 0.0113 (8) |
C19A | 0.0323 (10) | 0.0223 (9) | 0.0380 (10) | 0.0099 (8) | 0.0050 (8) | 0.0073 (7) |
C12B | 0.0380 (11) | 0.0402 (12) | 0.0394 (11) | 0.0138 (9) | 0.0084 (8) | 0.0140 (9) |
C16B | 0.0424 (11) | 0.0415 (12) | 0.0368 (10) | 0.0182 (10) | 0.0118 (9) | 0.0170 (9) |
C14B | 0.0377 (11) | 0.0390 (11) | 0.0349 (10) | 0.0158 (9) | 0.0076 (8) | 0.0148 (8) |
C13B | 0.0443 (12) | 0.0421 (12) | 0.0353 (10) | 0.0218 (10) | 0.0126 (8) | 0.0129 (9) |
C11B | 0.0475 (13) | 0.0432 (13) | 0.0439 (12) | 0.0190 (10) | 0.0090 (9) | 0.0087 (10) |
C1B | 0.0405 (11) | 0.0338 (11) | 0.0418 (11) | 0.0107 (9) | 0.0130 (9) | 0.0088 (9) |
C2B | 0.0516 (14) | 0.0436 (13) | 0.0532 (14) | 0.0182 (11) | 0.0108 (11) | 0.0125 (10) |
C17B | 0.0449 (12) | 0.0287 (11) | 0.0584 (14) | 0.0114 (9) | 0.0100 (10) | 0.0023 (9) |
C7B | 0.0599 (15) | 0.0471 (14) | 0.0385 (12) | 0.0105 (11) | 0.0033 (10) | 0.0151 (10) |
C6B | 0.0552 (14) | 0.0405 (13) | 0.0414 (12) | 0.0079 (11) | 0.0109 (10) | 0.0055 (10) |
C10B | 0.0498 (14) | 0.0393 (13) | 0.0685 (17) | 0.0147 (11) | 0.0086 (12) | 0.0164 (11) |
C15B | 0.0492 (14) | 0.0636 (17) | 0.0417 (13) | 0.0063 (12) | −0.0014 (10) | 0.0006 (11) |
C17A | 0.0442 (13) | 0.0422 (13) | 0.0665 (16) | 0.0173 (11) | 0.0110 (11) | 0.0253 (11) |
C16A | 0.0453 (13) | 0.0372 (13) | 0.0745 (17) | 0.0100 (10) | 0.0061 (12) | 0.0181 (11) |
C12A | 0.0472 (13) | 0.0648 (17) | 0.0455 (13) | 0.0138 (12) | 0.0003 (10) | 0.0108 (12) |
C1A | 0.0444 (13) | 0.0490 (15) | 0.0601 (16) | 0.0076 (11) | −0.0019 (11) | −0.0084 (12) |
C3B | 0.0576 (16) | 0.0453 (15) | 0.094 (2) | 0.0245 (13) | 0.0193 (15) | 0.0196 (14) |
C15A | 0.0569 (16) | 0.086 (2) | 0.0530 (15) | 0.0430 (15) | 0.0195 (12) | 0.0143 (14) |
C7A | 0.0643 (17) | 0.0546 (16) | 0.0561 (15) | 0.0188 (13) | 0.0112 (12) | 0.0116 (12) |
C8B | 0.0757 (19) | 0.0622 (18) | 0.0481 (14) | 0.0109 (15) | 0.0057 (13) | 0.0262 (13) |
C5B | 0.0748 (19) | 0.0435 (15) | 0.0575 (16) | 0.0099 (13) | 0.0227 (14) | −0.0044 (12) |
C6A | 0.0590 (16) | 0.0483 (15) | 0.0534 (15) | 0.0070 (12) | −0.0009 (12) | 0.0040 (11) |
C9B | 0.0707 (19) | 0.0611 (18) | 0.0713 (19) | 0.0182 (15) | 0.0098 (14) | 0.0374 (15) |
C14A | 0.0520 (14) | 0.0681 (17) | 0.0471 (14) | 0.0279 (13) | 0.0056 (11) | 0.0005 (12) |
C4B | 0.0698 (19) | 0.0387 (15) | 0.103 (3) | 0.0171 (14) | 0.0347 (17) | −0.0011 (15) |
C13A | 0.0524 (16) | 0.098 (2) | 0.0458 (15) | 0.0130 (16) | 0.0130 (12) | −0.0103 (15) |
C11A | 0.0480 (16) | 0.109 (3) | 0.0657 (18) | 0.0213 (17) | 0.0096 (13) | 0.0331 (18) |
C2A | 0.0544 (17) | 0.0495 (17) | 0.111 (3) | 0.0096 (14) | 0.0043 (17) | −0.0106 (17) |
C10A | 0.074 (2) | 0.0566 (19) | 0.104 (3) | 0.0119 (16) | −0.0068 (19) | 0.0296 (18) |
C5A | 0.089 (2) | 0.0557 (19) | 0.079 (2) | 0.0014 (17) | −0.0043 (18) | 0.0233 (16) |
C8A | 0.098 (3) | 0.0599 (19) | 0.081 (2) | 0.0280 (19) | 0.0175 (19) | 0.0112 (16) |
C4A | 0.082 (3) | 0.056 (2) | 0.134 (4) | −0.0001 (19) | −0.023 (3) | 0.032 (2) |
C3A | 0.060 (2) | 0.0501 (19) | 0.172 (5) | 0.0101 (16) | −0.004 (2) | 0.007 (2) |
C9A | 0.102 (3) | 0.064 (2) | 0.112 (3) | 0.030 (2) | 0.010 (2) | 0.018 (2) |
S1B—C7B | 1.765 (3) | C7B—C8B | 1.391 (3) |
S1B—C6B | 1.763 (3) | C6B—C5B | 1.386 (4) |
S1A—C7A | 1.758 (3) | C10B—H10B | 0.9300 |
S1A—C6A | 1.753 (3) | C10B—C9B | 1.374 (4) |
O2B—C18B | 1.203 (2) | C15B—H15A | 0.9600 |
O1B—H1B | 0.8200 | C15B—H15B | 0.9600 |
O1B—C18B | 1.309 (2) | C15B—H15C | 0.9600 |
O2A—C18A | 1.249 (2) | C17A—H17D | 0.9600 |
O3A—H3AA | 0.8200 | C17A—H17E | 0.9600 |
O3A—C19A | 1.304 (2) | C17A—H17F | 0.9600 |
O4B—C19B | 1.250 (2) | C16A—H16D | 0.9600 |
O4A—C19A | 1.197 (2) | C16A—H16E | 0.9600 |
O3B—C19B | 1.233 (3) | C16A—H16F | 0.9600 |
N2B—H2B | 0.9800 | C12A—C7A | 1.397 (4) |
N2B—C16B | 1.493 (2) | C12A—C11A | 1.433 (4) |
N2B—C14B | 1.513 (2) | C1A—C6A | 1.398 (4) |
N2B—C17B | 1.486 (3) | C1A—C2A | 1.388 (4) |
O1A—C18A | 1.231 (3) | C3B—H3B | 0.9300 |
N2A—H2A | 0.9800 | C3B—C4B | 1.371 (5) |
N2A—C17A | 1.474 (3) | C15A—H15D | 0.9600 |
N2A—C16A | 1.497 (3) | C15A—H15E | 0.9600 |
N2A—C14A | 1.524 (3) | C15A—H15F | 0.9600 |
N1B—C12B | 1.420 (3) | C15A—C14A | 1.503 (3) |
N1B—C13B | 1.451 (2) | C7A—C8A | 1.384 (4) |
N1B—C1B | 1.415 (3) | C8B—H8B | 0.9300 |
N1A—C12A | 1.396 (4) | C8B—C9B | 1.374 (4) |
N1A—C1A | 1.425 (4) | C5B—H5B | 0.9300 |
N1A—C13A | 1.460 (3) | C5B—C4B | 1.377 (5) |
C19B—C18B | 1.552 (3) | C6A—C5A | 1.383 (4) |
C18A—C19A | 1.558 (3) | C9B—H9B | 0.9300 |
C12B—C11B | 1.383 (3) | C14A—H14A | 0.9800 |
C12B—C7B | 1.394 (3) | C14A—C13A | 1.483 (4) |
C16B—H16A | 0.9600 | C4B—H4B | 0.9300 |
C16B—H16B | 0.9600 | C13A—H13C | 0.9700 |
C16B—H16C | 0.9600 | C13A—H13D | 0.9700 |
C14B—H14B | 0.9800 | C11A—H11A | 0.9300 |
C14B—C13B | 1.533 (3) | C11A—C10A | 1.369 (5) |
C14B—C15B | 1.508 (3) | C2A—H2AA | 0.9300 |
C13B—H13A | 0.9700 | C2A—C3A | 1.387 (6) |
C13B—H13B | 0.9700 | C10A—H10A | 0.9300 |
C11B—H11B | 0.9300 | C10A—C9A | 1.353 (6) |
C11B—C10B | 1.393 (3) | C5A—H5A | 0.9300 |
C1B—C2B | 1.393 (3) | C5A—C4A | 1.382 (5) |
C1B—C6B | 1.389 (3) | C8A—H8A | 0.9300 |
C2B—H2BA | 0.9300 | C8A—C9A | 1.374 (5) |
C2B—C3B | 1.389 (3) | C4A—H4A | 0.9300 |
C17B—H17A | 0.9600 | C4A—C3A | 1.365 (6) |
C17B—H17B | 0.9600 | C3A—H3A | 0.9300 |
C17B—H17C | 0.9600 | C9A—H9A | 0.9300 |
C6B—S1B—C7B | 97.74 (12) | H15A—C15B—H15C | 109.5 |
C6A—S1A—C7A | 97.92 (14) | H15B—C15B—H15C | 109.5 |
C18B—O1B—H1B | 109.5 | N2A—C17A—H17D | 109.5 |
C19A—O3A—H3AA | 109.5 | N2A—C17A—H17E | 109.5 |
C16B—N2B—H2B | 106.7 | N2A—C17A—H17F | 109.5 |
C16B—N2B—C14B | 114.20 (15) | H17D—C17A—H17E | 109.5 |
C14B—N2B—H2B | 106.7 | H17D—C17A—H17F | 109.5 |
C17B—N2B—H2B | 106.7 | H17E—C17A—H17F | 109.5 |
C17B—N2B—C16B | 109.53 (18) | N2A—C16A—H16D | 109.5 |
C17B—N2B—C14B | 112.56 (16) | N2A—C16A—H16E | 109.5 |
C17A—N2A—H2A | 107.1 | N2A—C16A—H16F | 109.5 |
C17A—N2A—C16A | 108.97 (19) | H16D—C16A—H16E | 109.5 |
C17A—N2A—C14A | 117.68 (19) | H16D—C16A—H16F | 109.5 |
C16A—N2A—H2A | 107.1 | H16E—C16A—H16F | 109.5 |
C16A—N2A—C14A | 108.36 (19) | N1A—C12A—C7A | 118.9 (3) |
C14A—N2A—H2A | 107.1 | N1A—C12A—C11A | 124.7 (3) |
C12B—N1B—C13B | 118.86 (18) | C7A—C12A—C11A | 116.4 (3) |
C1B—N1B—C12B | 116.34 (17) | C6A—C1A—N1A | 118.7 (2) |
C1B—N1B—C13B | 119.29 (17) | C2A—C1A—N1A | 122.6 (3) |
C12A—N1A—C1A | 118.4 (2) | C2A—C1A—C6A | 118.7 (3) |
C12A—N1A—C13A | 118.0 (3) | C2B—C3B—H3B | 119.6 |
C1A—N1A—C13A | 121.3 (3) | C4B—C3B—C2B | 120.9 (3) |
O4B—C19B—C18B | 115.09 (17) | C4B—C3B—H3B | 119.6 |
O3B—C19B—O4B | 126.97 (19) | H15D—C15A—H15E | 109.5 |
O3B—C19B—C18B | 117.92 (17) | H15D—C15A—H15F | 109.5 |
O2A—C18A—C19A | 114.99 (17) | H15E—C15A—H15F | 109.5 |
O1A—C18A—O2A | 127.43 (19) | C14A—C15A—H15D | 109.5 |
O1A—C18A—C19A | 117.57 (16) | C14A—C15A—H15E | 109.5 |
O2B—C18B—O1B | 124.89 (18) | C14A—C15A—H15F | 109.5 |
O2B—C18B—C19B | 122.65 (17) | C12A—C7A—S1A | 118.9 (2) |
O1B—C18B—C19B | 112.37 (16) | C8A—C7A—S1A | 120.6 (2) |
O3A—C19A—C18A | 112.11 (16) | C8A—C7A—C12A | 120.4 (3) |
O4A—C19A—O3A | 125.13 (18) | C7B—C8B—H8B | 119.9 |
O4A—C19A—C18A | 122.76 (17) | C9B—C8B—C7B | 120.1 (3) |
C11B—C12B—N1B | 122.9 (2) | C9B—C8B—H8B | 119.9 |
C11B—C12B—C7B | 118.9 (2) | C6B—C5B—H5B | 119.8 |
C7B—C12B—N1B | 118.1 (2) | C4B—C5B—C6B | 120.4 (3) |
N2B—C16B—H16A | 109.5 | C4B—C5B—H5B | 119.8 |
N2B—C16B—H16B | 109.5 | C1A—C6A—S1A | 118.5 (2) |
N2B—C16B—H16C | 109.5 | C5A—C6A—S1A | 120.5 (3) |
H16A—C16B—H16B | 109.5 | C5A—C6A—C1A | 120.9 (3) |
H16A—C16B—H16C | 109.5 | C10B—C9B—C8B | 119.8 (3) |
H16B—C16B—H16C | 109.5 | C10B—C9B—H9B | 120.1 |
N2B—C14B—H14B | 107.6 | C8B—C9B—H9B | 120.1 |
N2B—C14B—C13B | 110.07 (16) | N2A—C14A—H14A | 106.9 |
C13B—C14B—H14B | 107.6 | C15A—C14A—N2A | 112.1 (2) |
C15B—C14B—N2B | 111.02 (17) | C15A—C14A—H14A | 106.9 |
C15B—C14B—H14B | 107.6 | C13A—C14A—N2A | 110.0 (2) |
C15B—C14B—C13B | 112.62 (19) | C13A—C14A—C15A | 113.7 (3) |
N1B—C13B—C14B | 109.52 (17) | C13A—C14A—H14A | 106.9 |
N1B—C13B—H13A | 109.8 | C3B—C4B—C5B | 119.5 (2) |
N1B—C13B—H13B | 109.8 | C3B—C4B—H4B | 120.2 |
C14B—C13B—H13A | 109.8 | C5B—C4B—H4B | 120.2 |
C14B—C13B—H13B | 109.8 | N1A—C13A—C14A | 110.4 (2) |
H13A—C13B—H13B | 108.2 | N1A—C13A—H13C | 109.6 |
C12B—C11B—H11B | 120.0 | N1A—C13A—H13D | 109.6 |
C12B—C11B—C10B | 120.0 (2) | C14A—C13A—H13C | 109.6 |
C10B—C11B—H11B | 120.0 | C14A—C13A—H13D | 109.6 |
C2B—C1B—N1B | 122.9 (2) | H13C—C13A—H13D | 108.1 |
C6B—C1B—N1B | 118.4 (2) | C12A—C11A—H11A | 119.6 |
C6B—C1B—C2B | 118.7 (2) | C10A—C11A—C12A | 120.8 (3) |
C1B—C2B—H2BA | 120.0 | C10A—C11A—H11A | 119.6 |
C3B—C2B—C1B | 119.9 (3) | C1A—C2A—H2AA | 120.2 |
C3B—C2B—H2BA | 120.0 | C3A—C2A—C1A | 119.6 (4) |
N2B—C17B—H17A | 109.5 | C3A—C2A—H2AA | 120.2 |
N2B—C17B—H17B | 109.5 | C11A—C10A—H10A | 119.1 |
N2B—C17B—H17C | 109.5 | C9A—C10A—C11A | 121.8 (3) |
H17A—C17B—H17B | 109.5 | C9A—C10A—H10A | 119.1 |
H17A—C17B—H17C | 109.5 | C6A—C5A—H5A | 120.2 |
H17B—C17B—H17C | 109.5 | C4A—C5A—C6A | 119.5 (4) |
C12B—C7B—S1B | 118.32 (18) | C4A—C5A—H5A | 120.2 |
C8B—C7B—S1B | 121.3 (2) | C7A—C8A—H8A | 119.1 |
C8B—C7B—C12B | 120.4 (2) | C9A—C8A—C7A | 121.8 (4) |
C1B—C6B—S1B | 118.48 (18) | C9A—C8A—H8A | 119.1 |
C5B—C6B—S1B | 121.0 (2) | C5A—C4A—H4A | 120.1 |
C5B—C6B—C1B | 120.5 (3) | C3A—C4A—C5A | 119.8 (4) |
C11B—C10B—H10B | 119.7 | C3A—C4A—H4A | 120.1 |
C9B—C10B—C11B | 120.7 (3) | C2A—C3A—H3A | 119.3 |
C9B—C10B—H10B | 119.7 | C4A—C3A—C2A | 121.4 (4) |
C14B—C15B—H15A | 109.5 | C4A—C3A—H3A | 119.3 |
C14B—C15B—H15B | 109.5 | C10A—C9A—C8A | 118.8 (4) |
C14B—C15B—H15C | 109.5 | C10A—C9A—H9A | 120.6 |
H15A—C15B—H15B | 109.5 | C8A—C9A—H9A | 120.6 |
Compound | R index (%) | Space group | C6—S1—C7 (°) | Distances from S1 to plane (Å) | C1—N1—C12 (°) | C1—N1/C12—N1 (Å) | Dihedral angle (°) |
PTZ-Cl-succinic | 6.82 | P21/c | 98.68 | 0.090, 0.152 | 118.73 | 1.406, 1.418 | 142.37 |
PTZ-Cl-fumaric | 4.08 | P21/c | 98.60 | -0.101, -0.138 | 118.87 | 1.406, 1.418 | 141.12 |
PTZ-Cl-adipic | 4.03 | P21/c | 98.32 | 0.051, 0.100 | 118.07 | 1.412 (2), 1.408 (2) | 137.87 |
PTZ-Cl-oxalic | 3.74 | P21/n | 97.76 | -0.030, -0.170 | 117.30 | 1.414, 1.415 | 136.94 |
PTZ-oxalic | 5.66 | P1 | 97.92, 97.73 | 0.192, 0.051/0.022, -0.108 | 118.4, 116.31 | 1.425, 1.396/1.415, 1.420 | 137.78, 133.44 |
Structure | D—H···A | D···H | H···A | D···A | D—H···A |
PTZ-Cl-oxalic | N2—H2···Cl1 | 0.98 | 2.10 | 3.0550 (15) | 165 |
O1—H1···Cl1 | 0.82 | 2.17 | 2.9774 (14) | 168 | |
PTZ-Cl-succinic | N2—H2···Cl1 | 0.98 | 2.08 | 3.058 (2) | 172 |
O1—H1···Cl1 | 0.82 | 2.18 | 2.992 (3) | 169 | |
PTZ-Cl-fumaric (103 K) | N2—H2···Cl1 | 1.00 | 2.07 | 3.0594 (17) | 170 |
O1—H1···Cl1 | 0.84 | 2.14 | 2.9736 (16) | 172 | |
PTZ-Cl-fumaric (293 K) | N2—H2···Cl1 | 0.98 | 2.08 | 3.0588 (19) | 174 |
O1—H1···Cl1 | 0.82 | 2.15 | 2.9675 (4) | 170 | |
PTZ-Cl-adipic | N2—H2···Cl1 | 0.98 | 2.06 | 3.0351 (15) | 176 |
O1—H1···Cl1 | 0.82 | 2.20 | 3.0128 (15) | 174 | |
PTZ-oxalic | N2A—H2A···O3A | 0.98 | 2.31 | 3.036 (3) | 130 |
N2A—H2A···O1A | 0.98 | 1.84 | 2.739 (3) | 152 | |
N2B—H2B···O3B | 0.98 | 1.85 | 2.752 (3) | 151 | |
N2B—H2B···O1B | 0.98 | 2.35 | 3.092 (2) | 132 | |
O1B···H1B···O2A | 0.82 | 1.75 | 2.565 (2) | 171 | |
O3A···H3AA···O4B | 0.82 | 1.74 | 2.549 (2) | 170 |