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Novel cocrystals of promethazine hydrochloride [PTZ-Cl; systematic name:
N,
N-dimethyl-1-(10
H-phenothiazin-10-yl)propan-2-aminium chloride] with succinic acid (PTZ-Cl-succinic, C
17H
21N
2S
+·Cl
−·0.5C
4H
6O
4), fumaric acid (PTZ-Cl-fumaric, C
17H
21N
2S
+·Cl
−·0.5C
4H
4O
4) and adipic acid (PTZ-Cl-adipic, C
17H
21N
2S
+·Cl
−·0.5C
6H
10O
4) were prepared by solvent drop grinding and slow evaporation from acetonitrile solution, along with two oxalic acid cocrystals which were prepared in tetrahydrofuran (the oxalic acid hemisolvate, PTZ-Cl-oxalic, C
17H
21N
2S
+·Cl
−·0.5C
2H
2O
4) and nitromethane (the hydrogen oxalate salt, PTZ-oxalic, C
17H
21N
2S
+·C
2HO
4−). The crystal structures obtained by crystallization from tetrahydrofuran and acetonitrile include the Cl
− ion in the lattice structures, while the Cl
− ion is missing from the crystal structure obtained by crystallization from nitromethane (PTZ-oxalic). In order to explain the formation of the two types of supramolecular configurations with oxalic acid, the intermolecular interaction energies were calculated in the presence of the two solvents and the equilibrium configurations were determined using density functional theory (DFT). The cocrystals were studied by X-ray diffraction, IR spectroscopy and differential scanning calorimetry. Additionally, a stability test under special conditions and water solubility were also investigated. PTZ-Cl-succinic, PTZ-Cl-fumaric and PTZ-Cl-adipic crystallized having similar lattice parameter values, and showed a 2:1 PTZ-Cl to dicarboxylic acid stoichiometry. PTZ-Cl-oxalic crystallized in a 2:1 stoichiometric ratio, while the structure lacking the Cl atom belongs has a 1:1 stoichiometry. All the obtained crystals exhibit hydrogen bonds of the type PTZ
Cl
(dicarboxylic acid)
Cl
PTZ, except for PTZ-oxalic, which forms bifurcated bonds between the hydrogen oxalate and promethazinium ions, along with an infinite hydrogen-bonded chain between the hydrogen oxalate anions.
Supporting information
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).
N,
N-Dimethyl-1-(10
H-phenothiazin-10-yl)propan-2-aminium
chloride succinic acid monosolvate (Promethazine_Hydrochloride_succinic_acid)
top
Crystal data top
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 |
Data collection top
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 top
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 | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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. |
N,
N-Dimethyl-1-(10
H-phenothiazin-10-yl)propan-2-aminium
chloride fumaric acid monosolvate (Promethazine_Hydrochloride_fumaric_acid)
top
Crystal data top
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 |
Data collection top
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 top
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 | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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. |
N,
N-Dimethyl-1-(10
H-phenothiazin-10-yl)propan-2-aminium
chloride adipic acid monosolvate (Promethazine_Hydrochloride_adipic_acid)
top
Crystal data top
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 |
Data collection top
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 top
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 | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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. |
N,
N-Dimethyl-1-(10
H-phenothiazin-10-yl)propan-2-aminium
chloride oxalic acid hemisolvate (Promethazine_hydrochloride_oxalic_acid)
top
Crystal data top
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 |
Data collection top
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 top
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 | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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. |
N,
N-Dimethyl-1-(10
H-phenothiazin-10-yl)propan-2-aminium
hydrogen oxalate (Promethazine_oxalic_acid)
top
Crystal data top
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 |
Data collection top
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 top
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 | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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 |
A few geometrical representative characteristics of the cocrystals topCompound | 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 |
Hydrogen-bond geometry (Å, °) topStructure | 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 |
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