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Novel cocrystals of promethazine hydro­chloride [PTZ-Cl; systematic name: N,N-dimethyl-1-(10H-pheno­thia­zin-10-yl)propan-2-aminium chloride] with succinic acid (PTZ-Cl-succinic, C17H21N2S+·Cl·0.5C4H6O4), fumaric acid (PTZ-Cl-fumaric, C17H21N2S+·Cl·0.5C4H4O4) and adipic acid (PTZ-Cl-adipic, C17H21N2S+·Cl·0.5C6H10O4) 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, C17H21N2S+·Cl·0.5C2H2O4) and nitro­methane (the hydrogen oxalate salt, PTZ-oxalic, C17H21N2S+·C2HO4). 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618017904/qp3016sup1.cif
Contains datablocks global, Promethazine_Hydrochloride_succinic_acid, Promethazine_Hydrochloride_fumaric_acid, Promethazine_Hydrochloride_adipic_acid, Promethazine_hydrochloride_oxalic_acid, Promethazine_oxalic_acid

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618017904/qp3016Promethazine_hydrochloride_succinic_acidsup2.hkl
Contains datablock Promethazine_hydrochloride_succinic_acid

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618017904/qp3016Promethazine_Hydrochloride_fumaric_acidsup3.hkl
Contains datablock Promethazine_Hydrochloride_fumaric_acid

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618017904/qp3016Promethazine_Hydrochloride_adipic_acidsup4.hkl
Contains datablock Promethazine_Hydrochloride_adipic_acid

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618017904/qp3016Promethazine_hydrochloride_oxalic_acidsup5.hkl
Contains datablock Promethazine_hydrochloride_oxalic_acid

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618017904/qp3016Promethazine_oxalic_acidsup6.hkl
Contains datablock Promethazine_oxalic_acid

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618017904/qp3016Promethazine_hydrochloride_succinic_acidsup7.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618017904/qp3016Promethazine_Hydrochloride_fumaric_acidsup8.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618017904/qp3016Promethazine_Hydrochloride_adipic_acidsup9.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618017904/qp3016Promethazine_hydrochloride_oxalic_acidsup10.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618017904/qp3016Promethazine_oxalic_acidsup11.cml
Supplementary material

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229618017904/qp3016sup12.pdf
Additional supporting information

CCDC references: 1853756; 1853755; 1853759; 1853757; 1853758

Computing details top

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-(10H-phenothiazin-10-yl)propan-2-aminium chloride succinic acid monosolvate (Promethazine_Hydrochloride_succinic_acid) top
Crystal data top
C17H21N2S+·Cl·0.5C4H6O4F(000) = 804
Mr = 379.91Dx = 1.271 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 8.8247 (3) ÅCell parameters from 8891 reflections
b = 26.4201 (7) Åθ = 5.5–71.1°
c = 8.7393 (4) ŵ = 2.80 mm1
β = 103.070 (4)°T = 293 K
V = 1984.78 (12) Å3Needle, blue
Z = 40.25 × 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 = 1.000h = 1010
11754 measured reflectionsk = 3232
3503 independent reflectionsl = 108
3008 reflections with I > 2σ(I)
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.072H-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 reflectionsΔρmax = 0.63 e Å3
230 parametersΔρmin = 0.37 e Å3
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
xyzUiso*/Ueq
Cl10.60991 (10)0.28893 (3)0.57926 (9)0.0550 (3)
S11.11147 (12)0.06827 (3)0.75956 (12)0.0641 (3)
N20.4877 (3)0.18028 (8)0.5415 (2)0.0343 (5)
H20.5270410.2150100.5430370.041*
O10.6141 (4)0.39576 (9)0.4668 (3)0.0748 (8)
H10.6143120.3682660.5103770.112*
N10.8953 (3)0.13927 (10)0.5586 (3)0.0454 (6)
C140.6285 (3)0.14657 (10)0.5855 (3)0.0354 (6)
H140.6797440.1540720.6947280.042*
O20.5101 (5)0.42148 (10)0.6600 (3)0.0834 (10)
C110.9526 (4)0.21099 (12)0.7423 (3)0.0459 (7)
H110.8799990.2310540.6752890.055*
C130.7426 (3)0.15987 (12)0.4836 (3)0.0414 (6)
H13A0.7073730.1455050.3794810.050*
H13B0.7491950.1963170.4734120.050*
C101.0351 (4)0.23054 (14)0.8834 (4)0.0530 (8)
H101.0154040.2633760.9119850.064*
C71.0893 (3)0.13247 (12)0.8040 (3)0.0434 (6)
C120.9778 (3)0.16124 (11)0.6999 (3)0.0392 (6)
C10.9752 (4)0.10842 (12)0.4720 (4)0.0463 (7)
C61.0838 (4)0.07314 (12)0.5538 (4)0.0528 (8)
C160.3900 (4)0.17199 (15)0.3818 (4)0.0545 (8)
H16A0.3450980.1387450.3755840.082*
H16B0.4530340.1750090.3059560.082*
H16C0.3085600.1968330.3603190.082*
C170.3905 (4)0.17832 (13)0.6605 (4)0.0523 (8)
H17A0.4527840.1875100.7615960.078*
H17B0.3510300.1446290.6651800.078*
H17C0.3051880.2015420.6314480.078*
C91.1459 (5)0.20193 (15)0.9816 (4)0.0602 (9)
H91.2020380.2156101.0755060.072*
C180.5536 (5)0.43033 (12)0.5443 (4)0.0522 (8)
C81.1740 (4)0.15321 (14)0.9416 (4)0.0543 (8)
H81.2503910.1341151.0074280.065*
C20.9512 (5)0.11077 (15)0.3100 (4)0.0584 (9)
H2A0.8827850.1345500.2540150.070*
C51.1637 (5)0.04138 (15)0.4738 (6)0.0706 (11)
H51.2371170.0189170.5291430.085*
C190.5459 (5)0.48106 (12)0.4662 (4)0.0613 (10)
H19A0.6507800.4937790.4761130.074*
H19B0.4995120.4771010.3551190.074*
C31.0292 (6)0.07763 (18)0.2310 (5)0.0768 (13)
H31.0104540.0787240.1220030.092*
C41.1348 (6)0.04294 (17)0.3135 (7)0.0853 (15)
H41.1860240.0207470.2596850.102*
C150.5874 (5)0.09086 (13)0.5761 (4)0.0544 (8)
H15A0.5434130.0818330.4688210.082*
H15B0.5131020.0842070.6386410.082*
H15C0.6795690.0712000.6148400.082*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0694 (6)0.0276 (4)0.0660 (5)0.0036 (3)0.0114 (4)0.0002 (3)
S10.0647 (6)0.0394 (5)0.0856 (7)0.0075 (4)0.0111 (4)0.0105 (4)
N20.0354 (12)0.0306 (11)0.0395 (11)0.0001 (9)0.0138 (8)0.0020 (8)
O10.136 (3)0.0340 (13)0.0632 (15)0.0062 (14)0.0411 (15)0.0049 (10)
N10.0365 (13)0.0562 (16)0.0446 (12)0.0085 (11)0.0117 (10)0.0086 (10)
C140.0378 (14)0.0340 (14)0.0356 (13)0.0042 (10)0.0107 (10)0.0028 (9)
O20.148 (3)0.0492 (15)0.0670 (16)0.0053 (17)0.0537 (18)0.0123 (12)
C110.0453 (17)0.0487 (18)0.0464 (15)0.0078 (12)0.0159 (12)0.0014 (11)
C130.0366 (15)0.0497 (16)0.0400 (14)0.0046 (12)0.0130 (10)0.0024 (11)
C100.057 (2)0.054 (2)0.0517 (17)0.0018 (15)0.0196 (14)0.0053 (14)
C70.0390 (15)0.0458 (16)0.0480 (15)0.0006 (12)0.0155 (11)0.0086 (12)
C120.0345 (14)0.0478 (16)0.0387 (13)0.0030 (11)0.0155 (10)0.0007 (11)
C10.0391 (15)0.0419 (17)0.0643 (18)0.0090 (12)0.0253 (13)0.0112 (13)
C60.0448 (18)0.0335 (16)0.085 (2)0.0042 (13)0.0246 (15)0.0102 (14)
C160.0483 (18)0.066 (2)0.0463 (16)0.0062 (15)0.0057 (12)0.0001 (14)
C170.0502 (18)0.058 (2)0.0549 (17)0.0093 (15)0.0259 (14)0.0061 (14)
C90.065 (2)0.063 (2)0.0485 (18)0.0054 (17)0.0051 (14)0.0029 (15)
C180.080 (2)0.0317 (16)0.0448 (16)0.0096 (14)0.0153 (15)0.0019 (11)
C80.0452 (18)0.066 (2)0.0495 (17)0.0019 (15)0.0057 (12)0.0130 (14)
C20.062 (2)0.060 (2)0.062 (2)0.0149 (17)0.0332 (16)0.0151 (15)
C50.058 (2)0.045 (2)0.117 (3)0.0021 (16)0.036 (2)0.024 (2)
C190.106 (3)0.0325 (16)0.0534 (18)0.0099 (17)0.0343 (18)0.0024 (13)
C30.087 (3)0.081 (3)0.078 (3)0.024 (2)0.052 (2)0.033 (2)
C40.079 (3)0.059 (3)0.135 (4)0.011 (2)0.058 (3)0.040 (3)
C150.068 (2)0.0356 (17)0.063 (2)0.0026 (14)0.0218 (16)0.0052 (13)
Geometric parameters (Å, º) top
S1—C71.761 (3)C11—C121.397 (4)
S1—C61.764 (4)C10—C91.373 (5)
N2—C141.506 (3)C7—C121.403 (4)
N2—C161.481 (4)C7—C81.378 (5)
N2—C171.491 (3)C1—C61.410 (5)
O1—C181.320 (4)C1—C21.384 (5)
N1—C131.463 (4)C6—C51.383 (5)
N1—C121.409 (4)C9—C81.371 (5)
N1—C11.406 (4)C18—C191.499 (4)
C14—C131.528 (4)C2—C31.390 (5)
C14—C151.514 (4)C5—C41.366 (7)
O2—C181.183 (4)C19—C19i1.491 (7)
C11—C101.382 (5)C3—C41.387 (8)
C7—S1—C699.07 (14)C7—C12—N1119.5 (3)
C16—N2—C14115.1 (2)N1—C1—C6118.5 (3)
C16—N2—C17110.4 (3)C2—C1—N1123.0 (3)
C17—N2—C14111.9 (2)C2—C1—C6118.5 (3)
C12—N1—C13118.7 (2)C1—C6—S1119.1 (2)
C1—N1—C13119.8 (2)C5—C6—S1120.2 (3)
C1—N1—C12119.2 (2)C5—C6—C1120.7 (4)
N2—C14—C13109.3 (2)C8—C9—C10120.1 (3)
N2—C14—C15112.8 (2)O1—C18—C19111.6 (3)
C15—C14—C13111.9 (2)O2—C18—O1123.3 (3)
C10—C11—C12120.3 (3)O2—C18—C19125.1 (3)
N1—C13—C14108.3 (2)C9—C8—C7120.2 (3)
C9—C10—C11120.6 (3)C1—C2—C3120.1 (4)
C12—C7—S1118.4 (2)C4—C5—C6120.1 (4)
C8—C7—S1120.7 (2)C19i—C19—C18113.1 (3)
C8—C7—C12120.9 (3)C4—C3—C2120.6 (4)
C11—C12—N1122.6 (3)C5—C4—C3120.0 (3)
C11—C12—C7117.9 (3)
Symmetry code: (i) x+1, y+1, z+1.
N,N-Dimethyl-1-(10H-phenothiazin-10-yl)propan-2-aminium chloride fumaric acid monosolvate (Promethazine_Hydrochloride_fumaric_acid) top
Crystal data top
C17H21N2S+·Cl·0.5C4H4O4F(000) = 800
Mr = 378.90Dx = 1.322 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 8.7741 (3) ÅCell parameters from 3861 reflections
b = 25.8762 (7) Åθ = 3.4–71.0°
c = 8.6007 (3) ŵ = 2.92 mm1
β = 102.920 (3)°T = 103 K
V = 1903.27 (11) Å3Plate, blue
Z = 40.15 × 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 SourceRint = 0.035
ω scansθmax = 71.7°, θmin = 3.4°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
h = 109
Tmin = 0.650, Tmax = 1.000k = 3131
9870 measured reflectionsl = 910
3654 independent reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-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 reflectionsΔρmax = 0.39 e Å3
230 parametersΔρmin = 0.24 e Å3
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
xyzUiso*/Ueq
Cl10.59657 (6)0.28887 (2)0.62952 (6)0.02544 (14)
S11.10822 (6)0.06567 (2)0.80625 (6)0.02669 (15)
O10.6268 (2)0.39570 (6)0.51261 (18)0.0343 (4)
H10.6155690.3668400.5533210.051*
O20.4920 (2)0.42424 (6)0.68880 (19)0.0379 (4)
N20.47430 (19)0.17785 (6)0.58797 (19)0.0193 (4)
H20.5139180.2140930.5882920.023*
N10.8853 (2)0.13716 (7)0.6029 (2)0.0231 (4)
C120.9677 (2)0.16021 (8)0.7469 (2)0.0205 (4)
C130.7316 (2)0.15772 (8)0.5268 (2)0.0219 (4)
H13A0.6961480.1428050.4186990.026*
H13B0.7370650.1957450.5166070.026*
C91.1380 (3)0.20322 (8)1.0312 (3)0.0275 (5)
H91.1956510.2179151.1277800.033*
C10.9683 (2)0.10615 (8)0.5153 (2)0.0213 (4)
C140.6169 (2)0.14337 (8)0.6306 (2)0.0201 (4)
H140.6695550.1503910.7442700.024*
C61.0802 (2)0.07126 (8)0.5965 (3)0.0232 (4)
C110.9401 (2)0.21104 (8)0.7884 (2)0.0235 (4)
H110.8640790.2314180.7188210.028*
C81.1682 (2)0.15298 (8)0.9901 (2)0.0246 (5)
H81.2481910.1334481.0575300.030*
C160.3733 (3)0.16873 (9)0.4259 (2)0.0251 (5)
H16A0.3243350.1345910.4227200.038*
H16B0.4373850.1702480.3461490.038*
H16C0.2919750.1953550.4024870.038*
C101.0234 (3)0.23178 (8)0.9306 (3)0.0259 (5)
H101.0016160.2659880.9594060.031*
C20.9432 (3)0.10878 (8)0.3493 (3)0.0254 (5)
H2A0.8708650.1331390.2920730.030*
C150.5759 (3)0.08621 (8)0.6162 (3)0.0265 (5)
H15A0.5301940.0778130.5043590.040*
H15B0.5002700.0783550.6812020.040*
H15C0.6707740.0656380.6536470.040*
C51.1637 (3)0.03982 (8)0.5144 (3)0.0287 (5)
H51.2413190.0170090.5712430.034*
C71.0817 (2)0.13133 (8)0.8510 (2)0.0217 (4)
C190.5505 (3)0.48184 (8)0.4937 (3)0.0290 (5)
H190.6239380.4878660.4296150.035*
C180.5526 (3)0.43161 (8)0.5773 (3)0.0291 (5)
C170.3800 (2)0.17549 (8)0.7126 (2)0.0249 (5)
H17A0.4437900.1874100.8147770.037*
H17B0.3465640.1397980.7236290.037*
H17C0.2878020.1977180.6812020.037*
C41.1335 (3)0.04180 (8)0.3493 (3)0.0316 (5)
H41.1883290.0196860.2925280.038*
C31.0230 (3)0.07614 (9)0.2672 (3)0.0300 (5)
H31.0017840.0773080.1540420.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0274 (3)0.0233 (2)0.0248 (3)0.0006 (2)0.0040 (2)0.00080 (18)
S10.0271 (3)0.0257 (3)0.0265 (3)0.0018 (2)0.0044 (2)0.0031 (2)
O10.0505 (11)0.0277 (8)0.0265 (8)0.0010 (8)0.0122 (7)0.0027 (6)
O20.0551 (11)0.0319 (8)0.0306 (9)0.0015 (8)0.0177 (8)0.0028 (7)
N20.0163 (9)0.0252 (8)0.0170 (8)0.0006 (7)0.0050 (7)0.0021 (6)
N10.0156 (9)0.0334 (9)0.0201 (8)0.0043 (7)0.0034 (7)0.0023 (7)
C120.0159 (10)0.0290 (10)0.0188 (9)0.0011 (8)0.0084 (8)0.0011 (8)
C130.0156 (10)0.0316 (10)0.0186 (9)0.0012 (8)0.0042 (8)0.0003 (8)
C90.0268 (12)0.0354 (11)0.0193 (10)0.0046 (9)0.0029 (9)0.0012 (9)
C10.0153 (10)0.0265 (10)0.0243 (10)0.0052 (8)0.0089 (8)0.0042 (8)
C140.0150 (10)0.0276 (10)0.0178 (9)0.0022 (8)0.0038 (8)0.0012 (8)
C60.0192 (11)0.0256 (10)0.0264 (10)0.0048 (8)0.0084 (9)0.0014 (8)
C110.0199 (11)0.0306 (11)0.0219 (10)0.0031 (9)0.0085 (9)0.0030 (8)
C80.0199 (11)0.0327 (11)0.0207 (10)0.0006 (9)0.0035 (8)0.0051 (8)
C160.0211 (11)0.0361 (11)0.0174 (10)0.0023 (9)0.0026 (8)0.0018 (8)
C100.0248 (12)0.0284 (10)0.0264 (11)0.0009 (9)0.0100 (9)0.0002 (8)
C20.0211 (11)0.0326 (11)0.0240 (10)0.0049 (9)0.0084 (9)0.0019 (9)
C150.0255 (12)0.0255 (10)0.0290 (11)0.0022 (9)0.0071 (9)0.0013 (8)
C50.0231 (12)0.0248 (10)0.0397 (13)0.0029 (9)0.0101 (10)0.0035 (9)
C70.0191 (10)0.0256 (10)0.0226 (10)0.0007 (8)0.0090 (8)0.0032 (8)
C190.0376 (14)0.0278 (10)0.0213 (10)0.0090 (9)0.0063 (9)0.0014 (8)
C180.0352 (13)0.0287 (11)0.0219 (10)0.0081 (10)0.0033 (10)0.0009 (9)
C170.0201 (11)0.0343 (11)0.0224 (10)0.0024 (9)0.0095 (9)0.0014 (8)
C40.0295 (13)0.0280 (11)0.0433 (14)0.0079 (9)0.0205 (11)0.0101 (10)
C30.0312 (13)0.0345 (11)0.0283 (11)0.0084 (10)0.0153 (10)0.0069 (9)
Geometric parameters (Å, º) top
S1—C61.771 (2)C11—H110.9500
S1—C71.769 (2)C11—C101.385 (3)
O1—H10.8400C8—H80.9500
O1—C181.326 (3)C8—C71.384 (3)
O2—C181.211 (3)C16—H16A0.9800
N2—H21.0000C16—H16B0.9800
N2—C141.514 (2)C16—H16C0.9800
N2—C161.494 (2)C10—H100.9500
N2—C171.495 (2)C2—H2A0.9500
N1—C121.418 (3)C2—C31.386 (3)
N1—C131.461 (3)C15—H15A0.9800
N1—C11.409 (3)C15—H15B0.9800
C12—C111.398 (3)C15—H15C0.9800
C12—C71.401 (3)C5—H50.9500
C13—H13A0.9900C5—C41.386 (3)
C13—H13B0.9900C19—C19i1.312 (5)
C13—C141.533 (3)C19—H190.9500
C9—H90.9500C19—C181.483 (3)
C9—C81.388 (3)C17—H17A0.9800
C9—C101.385 (3)C17—H17B0.9800
C1—C61.400 (3)C17—H17C0.9800
C1—C21.397 (3)C4—H40.9500
C14—H141.0000C4—C31.386 (3)
C14—C151.521 (3)C3—H30.9500
C6—C51.389 (3)
C7—S1—C698.52 (9)N2—C16—H16B109.5
C18—O1—H1109.5N2—C16—H16C109.5
C14—N2—H2106.5H16A—C16—H16B109.5
C16—N2—H2106.5H16A—C16—H16C109.5
C16—N2—C14114.75 (16)H16B—C16—H16C109.5
C16—N2—C17110.79 (16)C9—C10—C11120.7 (2)
C17—N2—H2106.5C9—C10—H10119.6
C17—N2—C14111.24 (15)C11—C10—H10119.6
C12—N1—C13118.49 (16)C1—C2—H2A119.7
C1—N1—C12118.86 (17)C3—C2—C1120.6 (2)
C1—N1—C13120.22 (16)C3—C2—H2A119.7
C11—C12—N1122.36 (18)C14—C15—H15A109.5
C11—C12—C7118.57 (18)C14—C15—H15B109.5
C7—C12—N1119.06 (18)C14—C15—H15C109.5
N1—C13—H13A110.1H15A—C15—H15B109.5
N1—C13—H13B110.1H15A—C15—H15C109.5
N1—C13—C14108.12 (16)H15B—C15—H15C109.5
H13A—C13—H13B108.4C6—C5—H5120.1
C14—C13—H13A110.1C4—C5—C6119.8 (2)
C14—C13—H13B110.1C4—C5—H5120.1
C8—C9—H9120.2C12—C7—S1118.90 (15)
C10—C9—H9120.2C8—C7—S1120.25 (16)
C10—C9—C8119.6 (2)C8—C7—C12120.80 (19)
C6—C1—N1119.30 (18)C19i—C19—H19119.2
C2—C1—N1122.43 (19)C19i—C19—C18121.5 (3)
C2—C1—C6118.28 (19)C18—C19—H19119.2
N2—C14—C13109.31 (15)O1—C18—C19111.4 (2)
N2—C14—H14107.8O2—C18—O1124.4 (2)
N2—C14—C15112.69 (16)O2—C18—C19124.2 (2)
C13—C14—H14107.8N2—C17—H17A109.5
C15—C14—C13111.24 (17)N2—C17—H17B109.5
C15—C14—H14107.8N2—C17—H17C109.5
C1—C6—S1118.86 (16)H17A—C17—H17B109.5
C5—C6—S1120.08 (17)H17A—C17—H17C109.5
C5—C6—C1121.0 (2)H17B—C17—H17C109.5
C12—C11—H11119.9C5—C4—H4120.1
C10—C11—C12120.20 (19)C5—C4—C3119.8 (2)
C10—C11—H11119.9C3—C4—H4120.1
C9—C8—H8120.0C2—C3—H3119.8
C7—C8—C9120.03 (19)C4—C3—C2120.4 (2)
C7—C8—H8120.0C4—C3—H3119.8
N2—C16—H16A109.5
Symmetry code: (i) x+1, y+1, z+1.
N,N-Dimethyl-1-(10H-phenothiazin-10-yl)propan-2-aminium chloride adipic acid monosolvate (Promethazine_Hydrochloride_adipic_acid) top
Crystal data top
C17H21N2S+·Cl·0.5C6H10O4F(000) = 836
Mr = 393.94Dx = 1.237 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 8.8988 (2) ÅCell parameters from 9792 reflections
b = 27.7992 (5) Åθ = 5.1–71.2°
c = 8.7933 (2) ŵ = 2.64 mm1
β = 103.484 (2)°T = 293 K
V = 2115.32 (8) Å3, blue
Z = 40.15 × 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 SourceRint = 0.040
ω scansθmax = 71.8°, θmin = 5.1°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
h = 1010
Tmin = 0.382, Tmax = 1.000k = 3434
27108 measured reflectionsl = 109
4096 independent reflections
Refinement top
Refinement on F2Primary atom site location: iterative
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-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 reflectionsΔρmax = 0.19 e Å3
239 parametersΔρmin = 0.19 e Å3
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
xyzUiso*/Ueq
Cl10.44628 (6)0.28738 (2)0.33373 (6)0.06918 (17)
S10.94831 (6)0.07489 (2)0.49504 (7)0.07698 (19)
N20.32146 (14)0.18535 (5)0.30659 (15)0.0440 (3)
H20.3624280.2181630.3105630.053*
N10.72167 (15)0.14307 (5)0.31704 (17)0.0530 (3)
O20.3352 (2)0.40657 (5)0.4321 (2)0.0848 (5)
O10.4477 (2)0.39144 (5)0.23834 (17)0.0836 (5)
H10.4416700.3635710.2669040.125*
C130.57043 (17)0.16374 (6)0.24667 (19)0.0489 (4)
H13A0.5308550.1501820.1434410.059*
H13B0.5794590.1982800.2360500.059*
C120.80875 (17)0.16283 (6)0.45869 (19)0.0500 (4)
C10.80207 (18)0.11806 (6)0.2212 (2)0.0516 (4)
C140.46027 (17)0.15243 (6)0.35155 (19)0.0457 (4)
H140.5137610.1600680.4593940.055*
C110.7851 (2)0.20913 (7)0.5076 (2)0.0576 (4)
H110.7095940.2284790.4458930.069*
C160.2258 (2)0.17847 (7)0.1453 (2)0.0601 (5)
H16A0.1774780.1474020.1372030.090*
H16B0.2903640.1805900.0720030.090*
H16C0.1477640.2029780.1225030.090*
C70.92411 (18)0.13471 (7)0.5528 (2)0.0569 (4)
C20.7748 (2)0.12535 (7)0.0614 (2)0.0605 (5)
H2A0.7040010.1485630.0138260.073*
C60.9139 (2)0.08456 (7)0.2912 (3)0.0614 (5)
C180.3941 (3)0.42064 (7)0.3313 (2)0.0652 (5)
C170.2246 (2)0.18344 (7)0.4233 (2)0.0627 (5)
H17A0.2873200.1905770.5252550.094*
H17B0.1811740.1518380.4235640.094*
H17C0.1428940.2066560.3963110.094*
C200.4278 (2)0.50440 (6)0.4369 (3)0.0715 (6)
H20A0.3382850.4989420.4798290.086*
H20B0.4260050.5378040.4046020.086*
C150.4165 (2)0.09963 (6)0.3459 (2)0.0612 (5)
H15A0.3658750.0909790.2407400.092*
H15B0.3479680.0939820.4136670.092*
H15C0.5080510.0804980.3796910.092*
C100.8729 (2)0.22666 (8)0.6475 (2)0.0680 (5)
H100.8541160.2573600.6807650.082*
C81.0147 (2)0.15341 (9)0.6901 (2)0.0693 (6)
H81.0939180.1349930.7501650.083*
C90.9878 (2)0.19897 (9)0.7375 (2)0.0747 (6)
H91.0474100.2111170.8307420.090*
C50.9944 (2)0.05881 (8)0.2002 (3)0.0794 (7)
H51.0705140.0370540.2472580.095*
C190.4159 (3)0.47275 (7)0.2953 (3)0.0842 (7)
H19A0.3293260.4833010.2132550.101*
H19B0.5091020.4761400.2570120.101*
C40.9620 (3)0.06538 (9)0.0411 (4)0.0881 (8)
H41.0143760.0475540.0196210.106*
C30.8524 (3)0.09818 (8)0.0281 (3)0.0763 (6)
H30.8299950.1022630.1360380.092*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0755 (3)0.0468 (2)0.0785 (4)0.00046 (19)0.0044 (2)0.0044 (2)
S10.0645 (3)0.0677 (3)0.0961 (4)0.0118 (2)0.0134 (3)0.0213 (3)
N20.0368 (6)0.0489 (7)0.0462 (8)0.0008 (5)0.0093 (5)0.0009 (5)
N10.0380 (7)0.0696 (9)0.0502 (8)0.0073 (6)0.0077 (6)0.0045 (7)
O20.1136 (13)0.0628 (8)0.0843 (11)0.0212 (8)0.0360 (10)0.0067 (8)
O10.1309 (14)0.0591 (8)0.0632 (9)0.0057 (9)0.0277 (9)0.0007 (7)
C130.0365 (7)0.0639 (10)0.0449 (9)0.0018 (7)0.0063 (6)0.0001 (7)
C120.0343 (7)0.0686 (10)0.0485 (9)0.0002 (7)0.0120 (7)0.0038 (8)
C10.0407 (8)0.0528 (9)0.0646 (11)0.0067 (7)0.0187 (7)0.0068 (8)
C140.0374 (7)0.0544 (9)0.0434 (9)0.0021 (6)0.0055 (6)0.0008 (7)
C110.0450 (9)0.0728 (11)0.0531 (10)0.0033 (8)0.0076 (8)0.0026 (8)
C160.0483 (9)0.0759 (12)0.0507 (10)0.0073 (8)0.0008 (8)0.0002 (9)
C70.0393 (8)0.0738 (11)0.0579 (11)0.0007 (7)0.0120 (7)0.0135 (9)
C20.0587 (10)0.0638 (11)0.0645 (12)0.0130 (8)0.0255 (9)0.0078 (9)
C60.0467 (9)0.0534 (9)0.0869 (14)0.0036 (7)0.0211 (9)0.0037 (9)
C180.0825 (13)0.0546 (10)0.0516 (11)0.0104 (9)0.0014 (10)0.0027 (9)
C170.0524 (9)0.0794 (12)0.0612 (12)0.0075 (9)0.0229 (8)0.0019 (9)
C200.0741 (12)0.0430 (9)0.0906 (15)0.0047 (8)0.0055 (11)0.0010 (9)
C150.0624 (11)0.0535 (10)0.0688 (12)0.0025 (8)0.0174 (9)0.0063 (8)
C100.0599 (11)0.0827 (13)0.0602 (12)0.0055 (9)0.0114 (9)0.0077 (10)
C80.0436 (9)0.0986 (16)0.0614 (12)0.0012 (9)0.0037 (8)0.0230 (11)
C90.0629 (12)0.1030 (17)0.0514 (12)0.0142 (11)0.0006 (9)0.0023 (11)
C50.0576 (11)0.0587 (11)0.128 (2)0.0012 (9)0.0349 (13)0.0164 (13)
C190.1172 (19)0.0547 (11)0.0731 (14)0.0102 (11)0.0067 (13)0.0070 (10)
C40.0774 (15)0.0794 (15)0.125 (2)0.0174 (12)0.0586 (16)0.0402 (15)
C30.0791 (14)0.0814 (14)0.0811 (15)0.0243 (12)0.0442 (12)0.0229 (12)
Geometric parameters (Å, º) top
S1—C71.766 (2)C2—H2A0.9300
S1—C61.767 (2)C2—C31.386 (3)
N2—H20.9800C6—C51.391 (3)
N2—C141.5138 (19)C18—C191.505 (3)
N2—C161.487 (2)C17—H17A0.9600
N2—C171.487 (2)C17—H17B0.9600
N1—C131.4614 (19)C17—H17C0.9600
N1—C121.415 (2)C20—C20i1.509 (4)
N1—C11.409 (2)C20—H20A0.9700
O2—C181.196 (2)C20—H20B0.9700
O1—H10.8200C20—C191.508 (3)
O1—C181.317 (3)C15—H15A0.9600
C13—H13A0.9700C15—H15B0.9600
C13—H13B0.9700C15—H15C0.9600
C13—C141.527 (2)C10—H100.9300
C12—C111.388 (3)C10—C91.374 (3)
C12—C71.398 (2)C8—H80.9300
C1—C21.385 (3)C8—C91.372 (3)
C1—C61.397 (3)C9—H90.9300
C14—H140.9800C5—H50.9300
C14—C151.516 (2)C5—C41.373 (4)
C11—H110.9300C19—H19A0.9700
C11—C101.383 (3)C19—H19B0.9700
C16—H16A0.9600C4—H40.9300
C16—H16B0.9600C4—C31.369 (4)
C16—H16C0.9600C3—H30.9300
C7—C81.387 (3)
C7—S1—C698.30 (9)C5—C6—C1119.9 (2)
C14—N2—H2106.2O2—C18—O1122.87 (18)
C16—N2—H2106.2O2—C18—C19124.8 (2)
C16—N2—C14114.98 (13)O1—C18—C19112.4 (2)
C17—N2—H2106.2N2—C17—H17A109.5
C17—N2—C14111.53 (13)N2—C17—H17B109.5
C17—N2—C16111.02 (13)N2—C17—H17C109.5
C12—N1—C13118.76 (14)H17A—C17—H17B109.5
C1—N1—C13119.11 (14)H17A—C17—H17C109.5
C1—N1—C12117.87 (13)H17B—C17—H17C109.5
C18—O1—H1109.5C20i—C20—H20A108.9
N1—C13—H13A109.9C20i—C20—H20B108.9
N1—C13—H13B109.9H20A—C20—H20B107.7
N1—C13—C14108.72 (13)C19—C20—C20i113.4 (2)
H13A—C13—H13B108.3C19—C20—H20A108.9
C14—C13—H13A109.9C19—C20—H20B108.9
C14—C13—H13B109.9C14—C15—H15A109.5
C11—C12—N1122.74 (15)C14—C15—H15B109.5
C11—C12—C7118.60 (16)C14—C15—H15C109.5
C7—C12—N1118.66 (16)H15A—C15—H15B109.5
C2—C1—N1122.77 (16)H15A—C15—H15C109.5
C2—C1—C6118.91 (17)H15B—C15—H15C109.5
C6—C1—N1118.31 (17)C11—C10—H10119.8
N2—C14—C13108.51 (12)C9—C10—C11120.4 (2)
N2—C14—H14107.7C9—C10—H10119.8
N2—C14—C15112.89 (13)C7—C8—H8119.9
C13—C14—H14107.7C9—C8—C7120.24 (18)
C15—C14—C13112.05 (15)C9—C8—H8119.9
C15—C14—H14107.7C10—C9—H9120.0
C12—C11—H11119.8C8—C9—C10120.08 (19)
C10—C11—C12120.46 (17)C8—C9—H9120.0
C10—C11—H11119.8C6—C5—H5119.9
N2—C16—H16A109.5C4—C5—C6120.2 (2)
N2—C16—H16B109.5C4—C5—H5119.9
N2—C16—H16C109.5C18—C19—C20112.10 (19)
H16A—C16—H16B109.5C18—C19—H19A109.2
H16A—C16—H16C109.5C18—C19—H19B109.2
H16B—C16—H16C109.5C20—C19—H19A109.2
C12—C7—S1118.58 (14)C20—C19—H19B109.2
C8—C7—S1121.20 (15)H19A—C19—H19B107.9
C8—C7—C12120.20 (19)C5—C4—H4120.0
C1—C2—H2A119.9C3—C4—C5120.0 (2)
C1—C2—C3120.3 (2)C3—C4—H4120.0
C3—C2—H2A119.9C2—C3—H3119.7
C1—C6—S1119.05 (15)C4—C3—C2120.5 (2)
C5—C6—S1120.99 (17)C4—C3—H3119.7
Symmetry code: (i) x+1, y+1, z+1.
N,N-Dimethyl-1-(10H-phenothiazin-10-yl)propan-2-aminium chloride oxalic acid hemisolvate (Promethazine_hydrochloride_oxalic_acid) top
Crystal data top
C17H21N2S+·Cl·0.5C2H2O4F(000) = 772
Mr = 365.88Dx = 1.317 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54184 Å
a = 10.5507 (2) ÅCell parameters from 6477 reflections
b = 12.4382 (2) Åθ = 4.8–71.4°
c = 14.2966 (3) ŵ = 2.99 mm1
β = 100.445 (2)°T = 293 K
V = 1845.07 (6) Å3Needle, blue
Z = 40.18 × 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 Source3141 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.030
Detector resolution: 16.4335 pixels mm-1θmax = 71.7°, θmin = 4.8°
ω scansh = 1212
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
k = 1513
Tmin = 0.509, Tmax = 1.000l = 1717
11908 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H-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 reflectionsΔρmax = 0.20 e Å3
221 parametersΔρmin = 0.24 e Å3
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
xyzUiso*/Ueq
S10.17289 (4)0.37234 (4)0.77764 (4)0.05370 (15)
Cl10.85455 (4)0.18951 (3)0.86263 (4)0.05885 (16)
O20.87922 (14)0.49022 (12)0.90055 (11)0.0714 (4)
O10.99405 (13)0.36170 (10)0.98464 (10)0.0600 (3)
H10.9520280.3216400.9451820.090*
C230.96065 (16)0.46088 (14)0.96455 (12)0.0487 (4)
N20.73117 (12)0.32421 (11)0.69149 (10)0.0438 (3)
H20.7756630.2936750.7517570.053*
C120.40787 (16)0.28161 (13)0.83942 (12)0.0435 (4)
C80.22302 (19)0.17228 (15)0.85677 (14)0.0534 (4)
H80.1344260.1648920.8523990.064*
C140.59092 (15)0.33522 (13)0.70043 (13)0.0437 (4)
H140.5553250.2627410.7030670.052*
N10.45497 (13)0.38238 (11)0.81514 (11)0.0478 (3)
C130.58518 (16)0.39083 (14)0.79444 (14)0.0493 (4)
H13A0.6460740.3574760.8451050.059*
H13B0.6085160.4659390.7907090.059*
C70.27428 (16)0.26792 (13)0.83011 (12)0.0438 (4)
C150.51231 (18)0.39273 (17)0.61643 (15)0.0606 (5)
H15A0.5434120.4649830.6136830.091*
H15B0.4234880.3942200.6232990.091*
H15C0.5200570.3555320.5588940.091*
C110.48807 (18)0.19563 (14)0.87202 (14)0.0527 (4)
H110.5768970.2024590.8775240.063*
C90.3044 (2)0.08817 (16)0.88983 (14)0.0604 (5)
H90.2707760.0238090.9077050.072*
C60.26394 (16)0.48118 (14)0.83323 (12)0.0458 (4)
C160.79806 (18)0.42697 (16)0.67845 (15)0.0570 (5)
H16A0.7635820.4564980.6170700.068*
H16B0.8885950.4137360.6828670.068*
H16C0.7851690.4769780.7270150.068*
C10.39784 (16)0.47542 (13)0.84641 (12)0.0441 (4)
C20.46968 (19)0.56137 (15)0.89011 (13)0.0539 (4)
H2A0.5592150.5578650.9019620.065*
C50.2042 (2)0.57208 (16)0.86070 (14)0.0574 (5)
H50.1147330.5752360.8516280.069*
C170.7489 (2)0.24600 (17)0.61607 (17)0.0683 (6)
H17A0.7123180.2748880.5548430.082*
H17B0.7065370.1796980.6258180.082*
H17C0.8391780.2329860.6189130.082*
C40.2764 (2)0.65759 (16)0.90128 (16)0.0665 (6)
H40.2359980.7189610.9186760.080*
C100.4355 (2)0.09994 (16)0.89624 (14)0.0596 (5)
H100.4897070.0425070.9172240.072*
C30.4083 (2)0.65207 (16)0.91600 (15)0.0637 (5)
H30.4570660.7098970.9436790.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0404 (2)0.0532 (3)0.0652 (3)0.00064 (17)0.00346 (19)0.0010 (2)
Cl10.0585 (3)0.0352 (2)0.0737 (3)0.00148 (16)0.0121 (2)0.00359 (18)
O20.0736 (9)0.0577 (8)0.0685 (9)0.0051 (7)0.0253 (7)0.0013 (7)
O10.0616 (8)0.0484 (7)0.0622 (8)0.0005 (6)0.0094 (6)0.0054 (6)
C230.0464 (9)0.0492 (10)0.0479 (9)0.0054 (7)0.0013 (7)0.0001 (8)
N20.0385 (7)0.0428 (7)0.0495 (8)0.0038 (5)0.0063 (6)0.0052 (6)
C120.0439 (8)0.0412 (8)0.0451 (9)0.0013 (6)0.0068 (7)0.0069 (7)
C80.0585 (10)0.0503 (10)0.0538 (10)0.0102 (8)0.0166 (8)0.0063 (8)
C140.0365 (7)0.0371 (8)0.0562 (10)0.0033 (6)0.0053 (7)0.0022 (7)
N10.0393 (7)0.0411 (7)0.0647 (9)0.0039 (5)0.0136 (6)0.0081 (6)
C130.0386 (8)0.0480 (9)0.0613 (11)0.0064 (7)0.0091 (7)0.0113 (8)
C70.0455 (8)0.0432 (9)0.0432 (9)0.0026 (7)0.0094 (7)0.0040 (7)
C150.0480 (10)0.0602 (11)0.0664 (12)0.0049 (8)0.0088 (9)0.0005 (9)
C110.0515 (10)0.0497 (10)0.0547 (10)0.0048 (7)0.0039 (8)0.0066 (8)
C90.0863 (14)0.0431 (10)0.0552 (11)0.0074 (9)0.0224 (10)0.0008 (8)
C60.0510 (9)0.0438 (9)0.0448 (9)0.0023 (7)0.0141 (7)0.0030 (7)
C160.0489 (9)0.0522 (10)0.0691 (12)0.0089 (8)0.0086 (9)0.0017 (9)
C10.0507 (9)0.0395 (8)0.0432 (8)0.0011 (7)0.0118 (7)0.0006 (7)
C20.0616 (11)0.0476 (10)0.0533 (10)0.0092 (8)0.0125 (8)0.0048 (8)
C50.0635 (11)0.0523 (10)0.0617 (11)0.0124 (8)0.0256 (9)0.0081 (9)
C170.0751 (13)0.0545 (11)0.0797 (14)0.0052 (10)0.0259 (11)0.0104 (10)
C40.0934 (16)0.0454 (10)0.0689 (13)0.0117 (10)0.0368 (12)0.0002 (9)
C100.0789 (13)0.0462 (10)0.0522 (11)0.0118 (9)0.0078 (9)0.0006 (8)
C30.0928 (15)0.0443 (10)0.0576 (12)0.0093 (10)0.0233 (11)0.0088 (8)
Geometric parameters (Å, º) top
S1—C71.7615 (18)C14—C131.522 (2)
S1—C61.7636 (18)C14—C151.510 (2)
O2—C231.193 (2)N1—C131.461 (2)
O1—C231.301 (2)N1—C11.414 (2)
C23—C23i1.536 (3)C11—C101.383 (3)
N2—C141.514 (2)C9—C101.378 (3)
N2—C161.488 (2)C6—C11.393 (2)
N2—C171.489 (2)C6—C51.386 (2)
C12—N11.415 (2)C1—C21.391 (2)
C12—C71.402 (2)C2—C31.384 (3)
C12—C111.391 (2)C5—C41.374 (3)
C8—C71.388 (2)C4—C31.371 (3)
C8—C91.381 (3)
C7—S1—C697.75 (8)N1—C13—C14109.61 (13)
O2—C23—O1126.02 (17)C12—C7—S1118.26 (13)
O2—C23—C23i122.7 (2)C8—C7—S1120.79 (13)
O1—C23—C23i111.27 (18)C8—C7—C12120.86 (16)
C16—N2—C14115.20 (13)C10—C11—C12119.90 (18)
C16—N2—C17110.24 (15)C10—C9—C8119.78 (18)
C17—N2—C14111.90 (14)C1—C6—S1118.54 (13)
C7—C12—N1118.44 (15)C5—C6—S1121.03 (14)
C11—C12—N1122.97 (15)C5—C6—C1120.40 (17)
C11—C12—C7118.59 (16)C6—C1—N1118.64 (15)
C9—C8—C7119.60 (18)C2—C1—N1122.81 (15)
N2—C14—C13108.15 (13)C2—C1—C6118.55 (16)
C15—C14—N2112.33 (15)C3—C2—C1120.20 (18)
C15—C14—C13112.51 (15)C4—C5—C6120.35 (19)
C12—N1—C13119.91 (14)C3—C4—C5119.72 (18)
C1—N1—C12117.30 (13)C9—C10—C11121.20 (18)
C1—N1—C13118.40 (13)C4—C3—C2120.73 (19)
Symmetry code: (i) x+2, y+1, z+2.
N,N-Dimethyl-1-(10H-phenothiazin-10-yl)propan-2-aminium hydrogen oxalate (Promethazine_oxalic_acid) top
Crystal data top
2C17H21N2S+·2C2HO4Z = 2
Mr = 748.89F(000) = 792
Triclinic, P1Dx = 1.365 Mg m3
Dm = Mg m3
Dm measured by ?
a = 8.6840 (5) ÅCu Kα radiation, λ = 1.54184 Å
b = 11.3871 (5) ÅCell parameters from 4341 reflections
c = 20.0923 (11) Åθ = 4.3–70.7°
α = 104.106 (4)°µ = 1.81 mm1
β = 90.386 (4)°T = 293 K
γ = 108.340 (5)°Needle, transparent
V = 1821.53 (18) Å30.22 × 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 Source5440 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.026
Detector resolution: 16.4335 pixels mm-1θmax = 71.6°, θmin = 4.3°
ω scansh = 910
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
k = 1213
Tmin = 0.895, Tmax = 1.000l = 2420
11276 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-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 reflectionsΔρmax = 1.00 e Å3
477 parametersΔρmin = 0.42 e Å3
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
xyzUiso*/Ueq
S1B0.97430 (11)0.96690 (7)0.58855 (3)0.0687 (3)
S1A0.82546 (11)0.40289 (8)0.56984 (4)0.0703 (3)
O2B0.19593 (18)1.04776 (15)0.93869 (9)0.0439 (4)
O1B0.42893 (19)1.01721 (15)0.90748 (10)0.0471 (4)
H1B0.3829140.9449070.9117170.071*
O2A0.3068 (2)0.78397 (15)0.91353 (10)0.0497 (4)
O3A0.42181 (19)0.51367 (15)0.90215 (10)0.0479 (4)
H3AA0.3812700.4448520.9115070.072*
O4B0.31512 (19)1.28856 (15)0.91957 (9)0.0467 (4)
O4A0.1871 (2)0.54174 (16)0.93114 (10)0.0534 (5)
O3B0.5421 (2)1.24838 (16)0.88825 (11)0.0577 (5)
N2B0.7903 (2)1.14612 (15)0.88770 (8)0.0311 (4)
H2B0.6810171.1538080.8876200.037*
O1A0.5328 (2)0.74270 (16)0.88098 (12)0.0589 (5)
N2A0.7746 (2)0.63505 (16)0.87797 (9)0.0355 (4)
H2A0.6673760.6465490.8807520.043*
N1B1.0196 (2)1.04383 (18)0.73884 (9)0.0407 (4)
N1A0.6499 (3)0.4486 (3)0.69302 (11)0.0618 (6)
C19B0.4052 (2)1.22047 (18)0.90890 (11)0.0334 (4)
C18A0.3961 (2)0.71538 (18)0.90168 (11)0.0330 (4)
C18B0.3311 (2)1.08540 (18)0.92130 (10)0.0312 (4)
C19A0.3215 (2)0.57939 (18)0.91367 (10)0.0307 (4)
C12B1.0747 (3)1.1501 (2)0.70979 (11)0.0382 (5)
C16B0.7939 (3)1.0610 (2)0.93324 (11)0.0378 (5)
H16A0.7193960.9765960.9131640.057*
H16B0.7625271.0947130.9777150.057*
H16C0.9020401.0570520.9381450.057*
C14B0.8162 (3)1.0937 (2)0.81341 (10)0.0354 (4)
H14B0.8243101.1603710.7893930.043*
C13B0.9777 (3)1.0654 (2)0.80955 (11)0.0381 (5)
H13A1.0631431.1371520.8387220.046*
H13B0.9675960.9901270.8259110.046*
C11B1.1375 (3)1.2753 (2)0.74931 (12)0.0443 (5)
H11B1.1433841.2929080.7971310.053*
C1B1.0732 (3)0.9385 (2)0.71044 (11)0.0392 (5)
C2B1.1428 (3)0.8814 (2)0.75070 (14)0.0488 (6)
H2BA1.1568980.9128820.7983840.059*
C17B0.9061 (3)1.2767 (2)0.91853 (13)0.0458 (5)
H17A0.8685621.3143900.9606380.069*
H17B0.9128861.3286710.8868640.069*
H17C1.0118401.2712460.9280240.069*
C7B1.0655 (3)1.1262 (2)0.63819 (12)0.0494 (6)
C6B1.0579 (3)0.8915 (2)0.63926 (12)0.0485 (6)
C10B1.1919 (3)1.3751 (2)0.71754 (14)0.0520 (6)
H10B1.2332281.4590860.7443680.062*
C15B0.6729 (3)0.9784 (3)0.77851 (13)0.0569 (7)
H15A0.6653040.9098080.7995260.085*
H15B0.6874660.9517680.7304990.085*
H15C0.5746831.0002680.7832750.085*
C17A0.7841 (3)0.5552 (2)0.92464 (14)0.0481 (6)
H17D0.8928100.5517400.9282090.072*
H17E0.7090680.4702270.9066800.072*
H17F0.7567370.5917710.9694100.072*
C16A0.8994 (3)0.7649 (2)0.90414 (15)0.0525 (6)
H16D0.8781370.8039220.9495850.079*
H16E0.8942130.8173640.8739100.079*
H16F1.0059430.7566020.9056990.079*
C12A0.6205 (3)0.3186 (3)0.66280 (13)0.0543 (6)
C1A0.6468 (3)0.5297 (3)0.64939 (15)0.0572 (7)
C3B1.1912 (4)0.7772 (3)0.71952 (18)0.0633 (7)
H3B1.2375680.7393980.7466350.076*
C15A0.9371 (4)0.5376 (3)0.79170 (14)0.0612 (7)
H15D1.0285010.5968440.8225410.092*
H15E0.9642450.5308840.7449880.092*
H15F0.9103150.4550720.8010040.092*
C7A0.6940 (4)0.2827 (3)0.60301 (15)0.0589 (7)
C8B1.1243 (4)1.2265 (3)0.60721 (15)0.0626 (7)
H8B1.1224221.2095280.5594790.075*
C5B1.1074 (4)0.7879 (3)0.60905 (15)0.0640 (8)
H5B1.0972670.7576330.5613210.077*
C6A0.7163 (3)0.5112 (3)0.58675 (14)0.0578 (7)
C9B1.1852 (4)1.3505 (3)0.64699 (16)0.0648 (8)
H9B1.2217461.4177100.6262020.078*
C14A0.7934 (3)0.5848 (3)0.80198 (13)0.0563 (7)
H14A0.8148020.6573540.7813570.068*
C4B1.1714 (4)0.7294 (3)0.64929 (19)0.0740 (10)
H4B1.2010780.6580110.6289910.089*
C13A0.6377 (4)0.4887 (4)0.76703 (14)0.0736 (9)
H13C0.6119110.4147730.7859450.088*
H13D0.5505110.5252490.7751840.088*
C11A0.5182 (4)0.2165 (4)0.68841 (17)0.0734 (9)
H11A0.4661840.2354440.7279600.088*
C2A0.5751 (4)0.6250 (3)0.6662 (2)0.0790 (10)
H2AA0.5290430.6395300.7077690.095*
C10A0.4962 (4)0.0914 (3)0.6553 (2)0.0789 (10)
H10A0.4300580.0269140.6732780.095*
C5A0.7074 (5)0.5821 (3)0.54073 (19)0.0790 (10)
H5A0.7498910.5665680.4983460.095*
C8A0.6663 (5)0.1546 (3)0.5713 (2)0.0806 (10)
H8A0.7156400.1327440.5313550.097*
C4A0.6348 (5)0.6761 (4)0.5582 (3)0.0947 (13)
H4A0.6282800.7241590.5275290.114*
C3A0.5728 (5)0.6983 (4)0.6205 (3)0.0999 (15)
H3A0.5279390.7639120.6326240.120*
C9A0.5680 (5)0.0588 (4)0.5973 (2)0.0931 (12)
H9A0.5510610.0267250.5753710.112*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1B0.0967 (6)0.0547 (4)0.0380 (3)0.0058 (4)0.0094 (3)0.0066 (3)
S1A0.0857 (6)0.0639 (5)0.0618 (4)0.0272 (4)0.0341 (4)0.0124 (3)
O2B0.0373 (8)0.0398 (9)0.0642 (10)0.0158 (7)0.0172 (7)0.0266 (8)
O1B0.0397 (8)0.0285 (8)0.0839 (12)0.0180 (7)0.0210 (8)0.0245 (8)
O2A0.0461 (9)0.0301 (8)0.0832 (12)0.0211 (7)0.0220 (8)0.0212 (8)
O3A0.0420 (9)0.0300 (8)0.0828 (12)0.0187 (7)0.0238 (8)0.0252 (8)
O4B0.0415 (9)0.0303 (8)0.0771 (12)0.0185 (7)0.0167 (8)0.0205 (7)
O4A0.0374 (9)0.0398 (9)0.0914 (14)0.0146 (7)0.0235 (8)0.0290 (9)
O3B0.0388 (9)0.0360 (9)0.1123 (16)0.0174 (7)0.0270 (9)0.0371 (10)
N2B0.0301 (8)0.0282 (8)0.0380 (9)0.0126 (7)0.0087 (6)0.0099 (7)
O1A0.0412 (9)0.0359 (9)0.1141 (16)0.0190 (8)0.0317 (10)0.0367 (10)
N2A0.0315 (9)0.0352 (9)0.0414 (9)0.0150 (7)0.0065 (7)0.0072 (7)
N1B0.0532 (11)0.0388 (10)0.0356 (9)0.0201 (9)0.0152 (8)0.0126 (7)
N1A0.0602 (14)0.0770 (16)0.0393 (11)0.0200 (12)0.0082 (9)0.0022 (11)
C19B0.0314 (10)0.0231 (10)0.0464 (11)0.0096 (8)0.0034 (8)0.0091 (8)
C18A0.0326 (10)0.0244 (10)0.0441 (11)0.0113 (8)0.0061 (8)0.0100 (8)
C18B0.0305 (10)0.0266 (10)0.0396 (10)0.0113 (8)0.0040 (8)0.0113 (8)
C19A0.0323 (10)0.0223 (9)0.0380 (10)0.0099 (8)0.0050 (8)0.0073 (7)
C12B0.0380 (11)0.0402 (12)0.0394 (11)0.0138 (9)0.0084 (8)0.0140 (9)
C16B0.0424 (11)0.0415 (12)0.0368 (10)0.0182 (10)0.0118 (9)0.0170 (9)
C14B0.0377 (11)0.0390 (11)0.0349 (10)0.0158 (9)0.0076 (8)0.0148 (8)
C13B0.0443 (12)0.0421 (12)0.0353 (10)0.0218 (10)0.0126 (8)0.0129 (9)
C11B0.0475 (13)0.0432 (13)0.0439 (12)0.0190 (10)0.0090 (9)0.0087 (10)
C1B0.0405 (11)0.0338 (11)0.0418 (11)0.0107 (9)0.0130 (9)0.0088 (9)
C2B0.0516 (14)0.0436 (13)0.0532 (14)0.0182 (11)0.0108 (11)0.0125 (10)
C17B0.0449 (12)0.0287 (11)0.0584 (14)0.0114 (9)0.0100 (10)0.0023 (9)
C7B0.0599 (15)0.0471 (14)0.0385 (12)0.0105 (11)0.0033 (10)0.0151 (10)
C6B0.0552 (14)0.0405 (13)0.0414 (12)0.0079 (11)0.0109 (10)0.0055 (10)
C10B0.0498 (14)0.0393 (13)0.0685 (17)0.0147 (11)0.0086 (12)0.0164 (11)
C15B0.0492 (14)0.0636 (17)0.0417 (13)0.0063 (12)0.0014 (10)0.0006 (11)
C17A0.0442 (13)0.0422 (13)0.0665 (16)0.0173 (11)0.0110 (11)0.0253 (11)
C16A0.0453 (13)0.0372 (13)0.0745 (17)0.0100 (10)0.0061 (12)0.0181 (11)
C12A0.0472 (13)0.0648 (17)0.0455 (13)0.0138 (12)0.0003 (10)0.0108 (12)
C1A0.0444 (13)0.0490 (15)0.0601 (16)0.0076 (11)0.0019 (11)0.0084 (12)
C3B0.0576 (16)0.0453 (15)0.094 (2)0.0245 (13)0.0193 (15)0.0196 (14)
C15A0.0569 (16)0.086 (2)0.0530 (15)0.0430 (15)0.0195 (12)0.0143 (14)
C7A0.0643 (17)0.0546 (16)0.0561 (15)0.0188 (13)0.0112 (12)0.0116 (12)
C8B0.0757 (19)0.0622 (18)0.0481 (14)0.0109 (15)0.0057 (13)0.0262 (13)
C5B0.0748 (19)0.0435 (15)0.0575 (16)0.0099 (13)0.0227 (14)0.0044 (12)
C6A0.0590 (16)0.0483 (15)0.0534 (15)0.0070 (12)0.0009 (12)0.0040 (11)
C9B0.0707 (19)0.0611 (18)0.0713 (19)0.0182 (15)0.0098 (14)0.0374 (15)
C14A0.0520 (14)0.0681 (17)0.0471 (14)0.0279 (13)0.0056 (11)0.0005 (12)
C4B0.0698 (19)0.0387 (15)0.103 (3)0.0171 (14)0.0347 (17)0.0011 (15)
C13A0.0524 (16)0.098 (2)0.0458 (15)0.0130 (16)0.0130 (12)0.0103 (15)
C11A0.0480 (16)0.109 (3)0.0657 (18)0.0213 (17)0.0096 (13)0.0331 (18)
C2A0.0544 (17)0.0495 (17)0.111 (3)0.0096 (14)0.0043 (17)0.0106 (17)
C10A0.074 (2)0.0566 (19)0.104 (3)0.0119 (16)0.0068 (19)0.0296 (18)
C5A0.089 (2)0.0557 (19)0.079 (2)0.0014 (17)0.0043 (18)0.0233 (16)
C8A0.098 (3)0.0599 (19)0.081 (2)0.0280 (19)0.0175 (19)0.0112 (16)
C4A0.082 (3)0.056 (2)0.134 (4)0.0001 (19)0.023 (3)0.032 (2)
C3A0.060 (2)0.0501 (19)0.172 (5)0.0101 (16)0.004 (2)0.007 (2)
C9A0.102 (3)0.064 (2)0.112 (3)0.030 (2)0.010 (2)0.018 (2)
Geometric parameters (Å, º) top
S1B—C7B1.765 (3)C7B—C8B1.391 (3)
S1B—C6B1.763 (3)C6B—C5B1.386 (4)
S1A—C7A1.758 (3)C10B—H10B0.9300
S1A—C6A1.753 (3)C10B—C9B1.374 (4)
O2B—C18B1.203 (2)C15B—H15A0.9600
O1B—H1B0.8200C15B—H15B0.9600
O1B—C18B1.309 (2)C15B—H15C0.9600
O2A—C18A1.249 (2)C17A—H17D0.9600
O3A—H3AA0.8200C17A—H17E0.9600
O3A—C19A1.304 (2)C17A—H17F0.9600
O4B—C19B1.250 (2)C16A—H16D0.9600
O4A—C19A1.197 (2)C16A—H16E0.9600
O3B—C19B1.233 (3)C16A—H16F0.9600
N2B—H2B0.9800C12A—C7A1.397 (4)
N2B—C16B1.493 (2)C12A—C11A1.433 (4)
N2B—C14B1.513 (2)C1A—C6A1.398 (4)
N2B—C17B1.486 (3)C1A—C2A1.388 (4)
O1A—C18A1.231 (3)C3B—H3B0.9300
N2A—H2A0.9800C3B—C4B1.371 (5)
N2A—C17A1.474 (3)C15A—H15D0.9600
N2A—C16A1.497 (3)C15A—H15E0.9600
N2A—C14A1.524 (3)C15A—H15F0.9600
N1B—C12B1.420 (3)C15A—C14A1.503 (3)
N1B—C13B1.451 (2)C7A—C8A1.384 (4)
N1B—C1B1.415 (3)C8B—H8B0.9300
N1A—C12A1.396 (4)C8B—C9B1.374 (4)
N1A—C1A1.425 (4)C5B—H5B0.9300
N1A—C13A1.460 (3)C5B—C4B1.377 (5)
C19B—C18B1.552 (3)C6A—C5A1.383 (4)
C18A—C19A1.558 (3)C9B—H9B0.9300
C12B—C11B1.383 (3)C14A—H14A0.9800
C12B—C7B1.394 (3)C14A—C13A1.483 (4)
C16B—H16A0.9600C4B—H4B0.9300
C16B—H16B0.9600C13A—H13C0.9700
C16B—H16C0.9600C13A—H13D0.9700
C14B—H14B0.9800C11A—H11A0.9300
C14B—C13B1.533 (3)C11A—C10A1.369 (5)
C14B—C15B1.508 (3)C2A—H2AA0.9300
C13B—H13A0.9700C2A—C3A1.387 (6)
C13B—H13B0.9700C10A—H10A0.9300
C11B—H11B0.9300C10A—C9A1.353 (6)
C11B—C10B1.393 (3)C5A—H5A0.9300
C1B—C2B1.393 (3)C5A—C4A1.382 (5)
C1B—C6B1.389 (3)C8A—H8A0.9300
C2B—H2BA0.9300C8A—C9A1.374 (5)
C2B—C3B1.389 (3)C4A—H4A0.9300
C17B—H17A0.9600C4A—C3A1.365 (6)
C17B—H17B0.9600C3A—H3A0.9300
C17B—H17C0.9600C9A—H9A0.9300
C6B—S1B—C7B97.74 (12)H15A—C15B—H15C109.5
C6A—S1A—C7A97.92 (14)H15B—C15B—H15C109.5
C18B—O1B—H1B109.5N2A—C17A—H17D109.5
C19A—O3A—H3AA109.5N2A—C17A—H17E109.5
C16B—N2B—H2B106.7N2A—C17A—H17F109.5
C16B—N2B—C14B114.20 (15)H17D—C17A—H17E109.5
C14B—N2B—H2B106.7H17D—C17A—H17F109.5
C17B—N2B—H2B106.7H17E—C17A—H17F109.5
C17B—N2B—C16B109.53 (18)N2A—C16A—H16D109.5
C17B—N2B—C14B112.56 (16)N2A—C16A—H16E109.5
C17A—N2A—H2A107.1N2A—C16A—H16F109.5
C17A—N2A—C16A108.97 (19)H16D—C16A—H16E109.5
C17A—N2A—C14A117.68 (19)H16D—C16A—H16F109.5
C16A—N2A—H2A107.1H16E—C16A—H16F109.5
C16A—N2A—C14A108.36 (19)N1A—C12A—C7A118.9 (3)
C14A—N2A—H2A107.1N1A—C12A—C11A124.7 (3)
C12B—N1B—C13B118.86 (18)C7A—C12A—C11A116.4 (3)
C1B—N1B—C12B116.34 (17)C6A—C1A—N1A118.7 (2)
C1B—N1B—C13B119.29 (17)C2A—C1A—N1A122.6 (3)
C12A—N1A—C1A118.4 (2)C2A—C1A—C6A118.7 (3)
C12A—N1A—C13A118.0 (3)C2B—C3B—H3B119.6
C1A—N1A—C13A121.3 (3)C4B—C3B—C2B120.9 (3)
O4B—C19B—C18B115.09 (17)C4B—C3B—H3B119.6
O3B—C19B—O4B126.97 (19)H15D—C15A—H15E109.5
O3B—C19B—C18B117.92 (17)H15D—C15A—H15F109.5
O2A—C18A—C19A114.99 (17)H15E—C15A—H15F109.5
O1A—C18A—O2A127.43 (19)C14A—C15A—H15D109.5
O1A—C18A—C19A117.57 (16)C14A—C15A—H15E109.5
O2B—C18B—O1B124.89 (18)C14A—C15A—H15F109.5
O2B—C18B—C19B122.65 (17)C12A—C7A—S1A118.9 (2)
O1B—C18B—C19B112.37 (16)C8A—C7A—S1A120.6 (2)
O3A—C19A—C18A112.11 (16)C8A—C7A—C12A120.4 (3)
O4A—C19A—O3A125.13 (18)C7B—C8B—H8B119.9
O4A—C19A—C18A122.76 (17)C9B—C8B—C7B120.1 (3)
C11B—C12B—N1B122.9 (2)C9B—C8B—H8B119.9
C11B—C12B—C7B118.9 (2)C6B—C5B—H5B119.8
C7B—C12B—N1B118.1 (2)C4B—C5B—C6B120.4 (3)
N2B—C16B—H16A109.5C4B—C5B—H5B119.8
N2B—C16B—H16B109.5C1A—C6A—S1A118.5 (2)
N2B—C16B—H16C109.5C5A—C6A—S1A120.5 (3)
H16A—C16B—H16B109.5C5A—C6A—C1A120.9 (3)
H16A—C16B—H16C109.5C10B—C9B—C8B119.8 (3)
H16B—C16B—H16C109.5C10B—C9B—H9B120.1
N2B—C14B—H14B107.6C8B—C9B—H9B120.1
N2B—C14B—C13B110.07 (16)N2A—C14A—H14A106.9
C13B—C14B—H14B107.6C15A—C14A—N2A112.1 (2)
C15B—C14B—N2B111.02 (17)C15A—C14A—H14A106.9
C15B—C14B—H14B107.6C13A—C14A—N2A110.0 (2)
C15B—C14B—C13B112.62 (19)C13A—C14A—C15A113.7 (3)
N1B—C13B—C14B109.52 (17)C13A—C14A—H14A106.9
N1B—C13B—H13A109.8C3B—C4B—C5B119.5 (2)
N1B—C13B—H13B109.8C3B—C4B—H4B120.2
C14B—C13B—H13A109.8C5B—C4B—H4B120.2
C14B—C13B—H13B109.8N1A—C13A—C14A110.4 (2)
H13A—C13B—H13B108.2N1A—C13A—H13C109.6
C12B—C11B—H11B120.0N1A—C13A—H13D109.6
C12B—C11B—C10B120.0 (2)C14A—C13A—H13C109.6
C10B—C11B—H11B120.0C14A—C13A—H13D109.6
C2B—C1B—N1B122.9 (2)H13C—C13A—H13D108.1
C6B—C1B—N1B118.4 (2)C12A—C11A—H11A119.6
C6B—C1B—C2B118.7 (2)C10A—C11A—C12A120.8 (3)
C1B—C2B—H2BA120.0C10A—C11A—H11A119.6
C3B—C2B—C1B119.9 (3)C1A—C2A—H2AA120.2
C3B—C2B—H2BA120.0C3A—C2A—C1A119.6 (4)
N2B—C17B—H17A109.5C3A—C2A—H2AA120.2
N2B—C17B—H17B109.5C11A—C10A—H10A119.1
N2B—C17B—H17C109.5C9A—C10A—C11A121.8 (3)
H17A—C17B—H17B109.5C9A—C10A—H10A119.1
H17A—C17B—H17C109.5C6A—C5A—H5A120.2
H17B—C17B—H17C109.5C4A—C5A—C6A119.5 (4)
C12B—C7B—S1B118.32 (18)C4A—C5A—H5A120.2
C8B—C7B—S1B121.3 (2)C7A—C8A—H8A119.1
C8B—C7B—C12B120.4 (2)C9A—C8A—C7A121.8 (4)
C1B—C6B—S1B118.48 (18)C9A—C8A—H8A119.1
C5B—C6B—S1B121.0 (2)C5A—C4A—H4A120.1
C5B—C6B—C1B120.5 (3)C3A—C4A—C5A119.8 (4)
C11B—C10B—H10B119.7C3A—C4A—H4A120.1
C9B—C10B—C11B120.7 (3)C2A—C3A—H3A119.3
C9B—C10B—H10B119.7C4A—C3A—C2A121.4 (4)
C14B—C15B—H15A109.5C4A—C3A—H3A119.3
C14B—C15B—H15B109.5C10A—C9A—C8A118.8 (4)
C14B—C15B—H15C109.5C10A—C9A—H9A120.6
H15A—C15B—H15B109.5C8A—C9A—H9A120.6
A few geometrical representative characteristics of the cocrystals top
CompoundR index (%)Space groupC6—S1—C7 (°)Distances from S1 to plane (Å)C1—N1—C12 (°)C1—N1/C12—N1 (Å)Dihedral angle (°)
PTZ-Cl-succinic6.82P21/c98.680.090, 0.152118.731.406, 1.418142.37
PTZ-Cl-fumaric4.08P21/c98.60-0.101, -0.138118.871.406, 1.418141.12
PTZ-Cl-adipic4.03P21/c98.320.051, 0.100118.071.412 (2), 1.408 (2)137.87
PTZ-Cl-oxalic3.74P21/n97.76-0.030, -0.170117.301.414, 1.415136.94
PTZ-oxalic5.66P197.92, 97.730.192, 0.051/0.022, -0.108118.4, 116.311.425, 1.396/1.415, 1.420137.78, 133.44
Hydrogen-bond geometry (Å, °) top
StructureD—H···AD···HH···AD···AD—H···A
PTZ-Cl-oxalicN2—H2···Cl10.982.103.0550 (15)165
O1—H1···Cl10.822.172.9774 (14)168
PTZ-Cl-succinicN2—H2···Cl10.982.083.058 (2)172
O1—H1···Cl10.822.182.992 (3)169
PTZ-Cl-fumaric (103 K)N2—H2···Cl11.002.073.0594 (17)170
O1—H1···Cl10.842.142.9736 (16)172
PTZ-Cl-fumaric (293 K)N2—H2···Cl10.982.083.0588 (19)174
O1—H1···Cl10.822.152.9675 (4)170
PTZ-Cl-adipicN2—H2···Cl10.982.063.0351 (15)176
O1—H1···Cl10.822.203.0128 (15)174
PTZ-oxalicN2A—H2A···O3A0.982.313.036 (3)130
N2A—H2A···O1A0.981.842.739 (3)152
N2B—H2B···O3B0.981.852.752 (3)151
N2B—H2B···O1B0.982.353.092 (2)132
O1B···H1B···O2A0.821.752.565 (2)171
O3A···H3AA···O4B0.821.742.549 (2)170
 

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