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The compounds chlorothiazide and hydrochlorothiazide (crystalline form II) have been studied in their fully hydrogenous forms by powder neutron diffraction on the GEM diffractometer. The results of joint Rietveld refinement of the structures against multi-bank neutron and single-bank X-ray powder data are reported and show that accurate and precise structural information can be obtained from polycrystalline molecular organic materials by this route.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010876810705687X/bs5052sup1.cif
Contains datablocks global, CTZ_GEM_neutron_130K, CTZ_syn, HCT_GEM_neutron_295K, HCTZ_lab_295K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810705687X/bs5052sup2.txt
Contains datablocks CTZ_syn, CTZ_GEM_neutron_130K, HCTZ_lab_295K, HCT_GEM_neutron_295K

CCDC references: 666612; 666613; 666614; 679971; 679972

Computing details top

For both compounds, data collection: custom ISIS software; data reduction: custom ISIS software; program(s) used to solve structure: coordinates from single-crystal data; program(s) used to refine structure: Topas v3.1 (Coehlo, 2003).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
(CTZ_GEM_neutron_130K) 6-chloro-4H-1,2,4-benzathiadiazine-7-sulfonamide-1,1-dioxide top
Crystal data top
C7H6ClN3O4S2Z = 1
Mr = 295.72Cell parameters included in refinement
Triclinic, P1Dx = 1.877 Mg m3
Hall symbol: P1Neutron radiation, λ = ? Å
a = 4.8499 (3) ŵ = 0.12 mm1
b = 6.3694 (4) ÅT = 130 K
c = 8.9106 (6) ÅParticle morphology: Needle
α = 74.401 (1)°Colourless
β = 83.865 (1)°cylinder, 40 × 5 mm
γ = 80.524 (1)°Specimen preparation: Prepared at 293 K
V = 260.93 (3) Å3
Data collection top
GEM, ISIS
diffractometer
Scan method: Time of flight
Radiation source: Pulsed neutron sourceAbsorption correction: empirical (using intensity measurements)
Mu = 0.122(2) cm-1 parameter Mu refined from experimental data
Specimen mounting: 5mm vanadium cylinderical canTmin = ?, Tmax = ?
Data collection mode: transmission
Refinement top
Least-squares matrix: selected elements only149 parameters
Rp = 4.2506 restraints
Rwp = 1.104Only H-atom coordinates refined
Rexp = 0.414Weighting scheme based on measured s.u.'s w = 1/σ(Yobs)2
χ2 = 6.885(Δ/σ)max = 0.001
? data pointsBackground function: Chebyshev polynomial
Excluded region(s): excluded short and long TOF regions <1000.0/ms and >8000.0/ms excluded 9deg detector bank <1500.0/ms and >15000.0/ms excluded 18deg detector bank <1800.0/ms and >20000.0/ms excluded 35deg detector bank <2600.0/ms and >20200.0/ms excluded 64deg detector bank <3700.0/ms and >18000.0/ms excluded 90deg detector bank <5000.0/ms and >16600.0/ms excluded 153deg detector bankPreferred orientation correction: none
Profile function: Full Voigt with double exponetial
Crystal data top
C7H6ClN3O4S2γ = 80.524 (1)°
Mr = 295.72V = 260.93 (3) Å3
Triclinic, P1Z = 1
a = 4.8499 (3) ÅNeutron radiation, λ = ? Å
b = 6.3694 (4) ŵ = 0.12 mm1
c = 8.9106 (6) ÅT = 130 K
α = 74.401 (1)°cylinder, 40 × 5 mm
β = 83.865 (1)°
Data collection top
GEM, ISIS
diffractometer
Scan method: Time of flight
Specimen mounting: 5mm vanadium cylinderical canAbsorption correction: empirical (using intensity measurements)
Mu = 0.122(2) cm-1 parameter Mu refined from experimental data
Data collection mode: transmissionTmin = ?, Tmax = ?
Refinement top
Rp = 4.250? data points
Rwp = 1.104149 parameters
Rexp = 0.4146 restraints
χ2 = 6.885Only H-atom coordinates refined
Special details top

Experimental. The neutron data were collected on 6 detector banks and refined simultanously:

The neutron data was refined in a simultanious refinement with X-ray lab powder data. The details of the Lab X-ray powder experiment are given in a seperate data block

Geometry. Bond distances, bond angles, torsion angles and H-bond geometries were calculated using PLATON (Spek, 2003; program version 280604)

Refinement. For 9deg detector bank: _refine_ls_goodness_of_fit_all 1.184 for 18deg detector bank: _refine_ls_goodness_of_fit_all 1.856 for 35deg detector bank: _refine_ls_goodness_of_fit_all 2.410 for 64deg detector bank: _refine_ls_goodness_of_fit_all 3.684 for 90deg detector bank: _refine_ls_goodness_of_fit_all 3.551 for 153deg detector bank: _refine_ls_goodness_of_fit_all 3.401

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.353950.362061.039400.013 (1)*
S10.5940 (5)0.0210 (4)0.5986 (3)0.013 (1)*
S20.0201 (5)0.1410 (4)1.1524 (3)0.013 (1)*
O10.8439 (6)0.0796 (5)0.6790 (4)0.013 (1)*
O20.4667 (6)0.1098 (4)0.5258 (3)0.013 (1)*
O30.1480 (6)0.3449 (5)1.1439 (3)0.013 (1)*
O40.3208 (6)0.1350 (4)1.1748 (3)0.013 (1)*
N10.6614 (4)0.2386 (3)0.4653 (3)0.013 (1)*
N20.2755 (4)0.4769 (2)0.5479 (3)0.013 (1)*
N30.0764 (3)0.0590 (3)1.2877 (3)0.013 (1)*
C10.5019 (5)0.4305 (3)0.4490 (2)0.013 (1)*
C20.1991 (6)0.3302 (5)0.6833 (4)0.013 (1)*
C30.3477 (7)0.1140 (5)0.7312 (4)0.013 (1)*
C40.2710 (5)0.0258 (3)0.8744 (3)0.013 (1)*
C50.0551 (6)0.0426 (5)0.9753 (4)0.013 (1)*
C60.0870 (6)0.2599 (5)0.9263 (4)0.013 (1)*
C70.0217 (6)0.3993 (3)0.7867 (4)0.013 (1)*
H10.5506 (7)0.5573 (4)0.3475 (3)0.027 (2)*
H20.1887 (7)0.6340 (4)0.5226 (6)0.027 (2)*
H3A0.0494 (9)0.0672 (4)1.3225 (5)0.027 (2)*
H3B0.2826 (5)0.0597 (6)1.2775 (5)0.027 (2)*
H40.3846 (6)0.1853 (4)0.9189 (5)0.027 (2)*
H70.1217 (7)0.5672 (4)0.7520 (6)0.027 (2)*
Geometric parameters (Å, º) top
Cl1—C61.7064N2—H20.995 (3)
S1—O11.441 (4)N3—H3B0.994 (3)
S1—O21.429 (4)N3—H3A1.023 (4)
S1—N11.619 (3)C2—C71.429 (4)
S1—C31.737 (4)C2—C31.422 (5)
S2—O31.431 (4)C3—C41.399 (4)
S2—O41.446 (4)C4—C51.398 (4)
S2—N31.576 (3)C5—C61.417 (5)
S2—C51.737 (4)C6—C71.360 (5)
N1—C11.316 (3)C1—H11.073 (3)
N2—C11.377 (3)C4—H41.067 (4)
N2—C21.371 (4)C7—H71.076 (4)
O1—S1—O2117.8 (2)N2—C2—C3121.9 (3)
O1—S1—N1109.0 (2)N2—C2—C7119.8 (3)
O1—S1—C3107.8 (2)C3—C2—C7118.2 (3)
O2—S1—N1107.4 (2)C2—C3—C4119.8 (3)
O2—S1—C3108.4 (2)S1—C3—C4121.6 (2)
N1—S1—C3105.89 (19)S1—C3—C2118.1 (3)
O3—S2—O4118.2 (2)C3—C4—C5121.8 (2)
O3—S2—N3109.4 (2)S2—C5—C6124.2 (3)
O3—S2—C5104.8 (2)C4—C5—C6117.4 (3)
O4—S2—N3107.4 (2)S2—C5—C4118.5 (2)
O4—S2—C5108.1 (2)C5—C6—C7122.5 (3)
N3—S2—C5108.6 (2)Cl1—C6—C5121.67
S1—N1—C1122.7 (2)Cl1—C6—C7115.85
C1—N2—C2123.55 (19)C2—C7—C6120.3 (3)
C1—N2—H2114.3 (3)N1—C1—H1116.2 (3)
C2—N2—H2121.5 (4)N2—C1—H1118.5 (2)
S2—N3—H3A118.1 (3)C3—C4—H4122.6 (3)
S2—N3—H3B110.6 (3)C5—C4—H4115.4 (3)
H3A—N3—H3B118.8 (4)C2—C7—H7117.0 (4)
N1—C1—N2125.28 (19)C6—C7—H7122.6 (4)
O1—S1—N1—C1130.7 (3)C2—N2—C1—N14.6 (4)
O2—S1—N1—C1100.6 (3)C7—C2—C3—S1174.2 (3)
C3—S1—N1—C115.0 (3)N2—C2—C3—C4176.6 (3)
N1—S1—C3—C4170.4 (3)C3—C2—C7—C60.4 (4)
O2—S1—C3—C297.8 (3)C7—C2—C3—C41.6 (5)
N1—S1—C3—C217.2 (3)N2—C2—C7—C6175.6 (3)
O1—S1—C3—C2133.7 (3)N2—C2—C3—S110.8 (4)
O2—S1—C3—C474.7 (3)S1—C3—C4—C5174.1 (3)
O1—S1—C3—C453.8 (4)C2—C3—C4—C51.7 (5)
O4—S2—C5—C646.2 (4)C3—C4—C5—C60.7 (4)
O3—S2—C5—C6173.2 (3)C3—C4—C5—S2178.7 (3)
N3—S2—C5—C670.0 (3)S2—C5—C6—Cl10.63
O3—S2—C5—C47.5 (3)C4—C5—C6—C70.5 (5)
O4—S2—C5—C4134.4 (3)C4—C5—C6—Cl1179.98
N3—S2—C5—C4109.3 (3)S2—C5—C6—C7179.8 (3)
S1—N1—C1—N25.7 (4)C5—C6—C7—C20.6 (5)
C1—N2—C2—C7173.8 (2)Cl1—C6—C7—C2179.84
C1—N2—C2—C31.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.995 (3)2.289 (4)2.884 (3)117.3 (3)
N2—H2···N3ii0.995 (3)2.489 (5)3.301 (3)138.6 (4)
N3—H3A···N1iii1.023 (4)2.154 (4)3.134 (3)159.9 (4)
N3—H3B···O2iv0.994 (3)2.396 (5)2.912 (3)111.5 (3)
N3—H3B···O4v0.994 (3)2.079 (4)2.993 (3)152.0 (4)
C1—H1···O4vi1.073 (3)2.275 (4)3.327 (3)166.4 (2)
C4—H4···O31.067 (4)2.273 (5)2.779 (4)107.0 (3)
C7—H7···O1vii1.076 (4)2.151 (5)3.173 (4)157.9 (3)
Symmetry codes: (i) x, y+1, z; (ii) x, y+1, z1; (iii) x1, y, z+1; (iv) x, y, z+1; (v) x+1, y, z; (vi) x+1, y+1, z1; (vii) x1, y+1, z.
(HCT_GEM_neutron_295K) 6-chloro-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide-1,1-dioxide top
Crystal data top
C7H8ClN3O4S2Cell parameters included in refinement
Mr = 297.74Dx = 1.801 Mg m3
Monoclinic, P21/cNeutron radiation, λ = ? Å
Hall symbol: -P 2ybcµ = 0.04 mm1
a = 9.4855 (3) ÅT = 295 K
b = 8.3325 (2) ÅParticle morphology: Needle
c = 15.1201 (4) ÅColourless
β = 113.240 (3)°cylinder, 40 × 5 mm
V = 1098.08 (6) Å3Specimen preparation: Prepared at 295 K
Z = 4
Data collection top
GEM, ISIS
diffractometer
Scan method: Time of flight
Radiation source: Pulsed neutron sourceAbsorption correction: empirical (using intensity measurements)
Mu = 0.043(2) cm-1 parameter Mu refined from experimental data
Specimen mounting: 5mm vanadium cylinderical canTmin = ?, Tmax = ?
Data collection mode: transmission
Refinement top
Least-squares matrix: selected elements only149 parameters
Rp = 1.66024 restraints
Rwp = 0.722Only H-atom coordinates refined
Rexp = 0.259Weighting scheme based on measured s.u.'s w = 1/σ(Yobs)2
χ2 = 7.896(Δ/σ)max = 0.001
? data pointsBackground function: Chebyshev polynomial
Excluded region(s): excluded short and long TOF regions <2000.0/ms and >8000.0/ms excluded 9deg detector bank <1900.0/ms and >15000.0/ms excluded 18deg detector bank <2800.0/ms and >20000.0/ms excluded 35deg detector bank <5000.0/ms and >20000.0/ms excluded 64deg detector bank <9000.0/ms and >18000.0/ms excluded 90deg detector bank <9000.0/ms and >16600.0/ms excluded 153deg detector bankPreferred orientation correction: none
Profile function: Full Voigt with double exponetial
Crystal data top
C7H8ClN3O4S2V = 1098.08 (6) Å3
Mr = 297.74Z = 4
Monoclinic, P21/cNeutron radiation, λ = ? Å
a = 9.4855 (3) ŵ = 0.04 mm1
b = 8.3325 (2) ÅT = 295 K
c = 15.1201 (4) Åcylinder, 40 × 5 mm
β = 113.240 (3)°
Data collection top
GEM, ISIS
diffractometer
Scan method: Time of flight
Specimen mounting: 5mm vanadium cylinderical canAbsorption correction: empirical (using intensity measurements)
Mu = 0.043(2) cm-1 parameter Mu refined from experimental data
Data collection mode: transmissionTmin = ?, Tmax = ?
Refinement top
Rp = 1.660? data points
Rwp = 0.722149 parameters
Rexp = 0.25924 restraints
χ2 = 7.896Only H-atom coordinates refined
Special details top

Experimental. The neutron data were collected on 6 detector banks and refined simultanously:

The neutron data was refined in a simultanious refinement with X-ray lab powder data. The details of the Lab X-ray powder experiment are given in a seperate data block

Geometry. Bond distances, bond angles, torsion angles and H-bond geometries were calculated using PLATON (Spek, 2003; program version 280604)

Refinement. For 9deg detector bank: _refine_ls_goodness_of_fit_all 1.141 for 18deg detector bank: _refine_ls_goodness_of_fit_all 2.085 for 35deg detector bank: _refine_ls_goodness_of_fit_all 2.627 for 64deg detector bank: _refine_ls_goodness_of_fit_all 4.380 for 90deg detector bank: _refine_ls_goodness_of_fit_all 3.125 for 153deg detector bank: _refine_ls_goodness_of_fit_all 4.381

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.75038 (16)0.3442 (3)0.62501 (15)0.019*
S10.03927 (16)0.24694 (17)0.44712 (9)0.019*
S20.54301 (14)0.50558 (17)0.72842 (10)0.019*
O10.0122 (3)0.2025 (5)0.52140 (12)0.019*
O20.0291 (5)0.3814 (2)0.3869 (2)0.019*
O30.41524 (18)0.5393 (4)0.75369 (18)0.019*
O40.6265 (3)0.6383 (3)0.7136 (2)0.019*
N10.01778 (18)0.09117 (1)0.37695 (10)0.019*
N20.27510 (14)0.0985 (2)0.37870 (10)0.019*
N30.65916 (15)0.39576 (17)0.81178 (11)0.019*
C10.11034 (15)0.10513 (17)0.31977 (10)0.019*
C20.33301 (15)0.2004 (2)0.45957 (11)0.019*
C30.23925 (15)0.2748 (3)0.49878 (11)0.019*
C40.30642 (14)0.3675 (3)0.58054 (11)0.019*
C50.46443 (14)0.3875 (3)0.62381 (11)0.019*
C60.55348 (15)0.3192 (2)0.57983 (11)0.019*
C70.49119 (14)0.2217 (3)0.49984 (11)0.019*
H1A0.0766 (7)0.2120 (2)0.27492 (18)0.023*
H1B0.0847 (6)0.0040 (2)0.27023 (16)0.023*
H20.3445 (2)0.0615 (7)0.34684 (14)0.023*
H3A0.76209 (18)0.3974 (7)0.8070 (3)0.023*
H3B0.6316 (8)0.2808 (2)0.8171 (4)0.023*
H40.2314 (2)0.4136 (8)0.61311 (18)0.023*
H50.0248 (5)0.0057 (2)0.41790 (16)0.023*
H70.5666 (2)0.1785 (8)0.46711 (14)0.023*
Geometric parameters (Å, º) top
Cl1—C61.730 (2)N2—H21.005 (3)
S1—O11.439 (3)N3—H3A1.007 (3)
S1—O21.428 (3)N3—H3B1.005 (3)
S1—N11.6375 (16)C2—C31.394 (2)
S1—C31.759 (2)C2—C71.390 (2)
S2—O31.435 (3)C3—C41.382 (3)
S2—O41.428 (3)C4—C51.389 (2)
S2—N31.595 (2)C5—C61.387 (2)
S2—C51.759 (2)C6—C71.381 (2)
N1—C11.460 (2)C1—H1A1.088 (2)
N2—C11.463 (2)C1—H1B1.089 (2)
N2—C21.410 (2)C4—H41.083 (4)
N1—H51.003 (2)C7—H71.080 (3)
O1—S1—O2119.4 (3)N2—C2—C3122.76 (15)
O1—S1—N1107.94 (18)C3—C2—C7121.09 (16)
O1—S1—C3109.03 (13)C2—C3—C4118.87 (14)
O2—S1—N1107.44 (13)S1—C3—C2120.65 (15)
O2—S1—C3108.6 (2)S1—C3—C4120.46 (14)
N1—S1—C3103.24 (13)C3—C4—C5121.30 (16)
O3—S2—O4118.0 (2)S2—C5—C4119.10 (14)
O3—S2—N3107.13 (15)S2—C5—C6122.58 (13)
O3—S2—C5104.25 (14)C4—C5—C6118.25 (16)
O4—S2—N3108.38 (15)Cl1—C6—C5121.89 (14)
O4—S2—C5110.88 (15)Cl1—C6—C7116.03 (14)
N3—S2—C5107.77 (12)C5—C6—C7122.02 (15)
S1—N1—C1111.74 (10)C2—C7—C6118.26 (15)
C1—N2—C2117.55 (13)N1—C1—H1A109.7 (3)
S1—N1—H5106.07 (17)N1—C1—H1B108.8 (3)
C1—N1—H5121.4 (3)N2—C1—H1A113.0 (3)
C1—N2—H2117.63 (18)N2—C1—H1B106.5 (3)
C2—N2—H2119.7 (2)H1A—C1—H1B105.9 (2)
S2—N3—H3A108.8 (3)C3—C4—H4116.8 (2)
S2—N3—H3B119.3 (4)C5—C4—H4121.6 (2)
H3A—N3—H3B108.0 (6)C2—C7—H7123.5 (2)
N1—C1—N2112.57 (12)C6—C7—H7117.8 (2)
N2—C2—C7116.14 (15)
O1—S1—N1—C1161.39 (16)C1—N2—C2—C7164.54 (16)
O2—S1—N1—C168.6 (2)C3—C2—C7—C60.2 (3)
C3—S1—N1—C146.03 (14)N2—C2—C3—C4177.35 (18)
O1—S1—C3—C2129.9 (2)C7—C2—C3—S1179.97 (16)
O1—S1—C3—C448.4 (3)N2—C2—C3—S10.9 (3)
O2—S1—C3—C298.5 (2)N2—C2—C7—C6179.34 (17)
O2—S1—C3—C483.2 (2)C7—C2—C3—C41.7 (3)
N1—S1—C3—C215.3 (2)S1—C3—C4—C5178.31 (18)
N1—S1—C3—C4162.96 (18)C2—C3—C4—C50.0 (3)
O3—S2—C5—C48.0 (3)C3—C4—C5—S2179.43 (18)
O3—S2—C5—C6175.2 (2)C3—C4—C5—C63.6 (3)
O4—S2—C5—C4120.0 (2)S2—C5—C6—C7177.48 (17)
O4—S2—C5—C656.9 (2)S2—C5—C6—Cl10.3 (3)
N3—S2—C5—C4121.57 (19)C4—C5—C6—Cl1177.20 (18)
N3—S2—C5—C661.5 (2)C4—C5—C6—C75.6 (3)
S1—N1—C1—N266.88 (15)C5—C6—C7—C24.0 (3)
C2—N2—C1—N150.24 (18)Cl1—C6—C7—C2178.70 (17)
C1—N2—C2—C316.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O3i1.005 (3)1.971 (4)2.940 (3)160.9 (3)
N3—H3A···Cl11.007 (3)2.746 (5)3.292 (3)114.4 (3)
N3—H3A···N1ii1.007 (3)2.233 (3)3.148 (2)150.4 (3)
N3—H3B···O3iii1.005 (3)2.240 (4)3.122 (4)145.8 (5)
N3—H3B···O4iii1.005 (3)2.593 (8)3.357 (3)132.8 (5)
N1—H5···O1iv1.003 (2)1.906 (4)2.901 (4)171.1 (3)
C1—H1B···O2v1.089 (2)2.445 (4)3.455 (3)153.6 (2)
C4—H4···O31.083 (4)2.394 (4)2.799 (3)100.36 (19)
C4—H4···O2vi1.083 (4)2.569 (6)3.544 (4)149.4 (4)
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x+1, y+1/2, z+1/2; (iii) x+1, y1/2, z+3/2; (iv) x, y, z+1; (v) x, y1/2, z+1/2; (vi) x, y+1, z+1.

Experimental details

(CTZ_GEM_neutron_130K)(HCT_GEM_neutron_295K)
Crystal data
Chemical formulaC7H6ClN3O4S2C7H8ClN3O4S2
Mr295.72297.74
Crystal system, space groupTriclinic, P1Monoclinic, P21/c
Temperature (K)130295
a, b, c (Å)4.8499 (3), 6.3694 (4), 8.9106 (6)9.4855 (3), 8.3325 (2), 15.1201 (4)
α, β, γ (°)74.401 (1), 83.865 (1), 80.524 (1)90, 113.240 (3), 90
V3)260.93 (3)1098.08 (6)
Z14
Radiation typeNeutron, λ = ? ÅNeutron, λ = ? Å
µ (mm1)0.120.04
Specimen shape, size (mm)Cylinder, 40 × 5Cylinder, 40 × 5
Data collection
DiffractometerGEM, ISIS
diffractometer
GEM, ISIS
diffractometer
Specimen mounting5mm vanadium cylinderical can5mm vanadium cylinderical can
Data collection modeTransmissionTransmission
Scan methodTime of flightTime of flight
Absorption correctionEmpirical (using intensity measurements)
Mu = 0.122(2) cm-1 parameter Mu refined from experimental data
2θ values (°)2θmin = ? 2θmax = ? 2θstep = ?2θmin = ? 2θmax = ? 2θstep = ?
Refinement
R factors and goodness of fitRp = 4.250, Rwp = 1.104, Rexp = 0.414, χ2 = 6.885Rp = 1.660, Rwp = 0.722, Rexp = 0.259, χ2 = 7.896
No. of data points??
No. of parameters149149
No. of restraints624
H-atom treatmentOnly H-atom coordinates refinedOnly H-atom coordinates refined

Computer programs: custom ISIS software, coordinates from single-crystal data, Topas v3.1 (Coehlo, 2003).

Selected bond lengths (Å) for (CTZ_GEM_neutron_130K) top
Cl1—C61.7064N2—H20.995 (3)
S1—O11.441 (4)N3—H3B0.994 (3)
S1—O21.429 (4)N3—H3A1.023 (4)
S1—N11.619 (3)C2—C71.429 (4)
S1—C31.737 (4)C2—C31.422 (5)
S2—O31.431 (4)C3—C41.399 (4)
S2—O41.446 (4)C4—C51.398 (4)
S2—N31.576 (3)C5—C61.417 (5)
S2—C51.737 (4)C6—C71.360 (5)
N1—C11.316 (3)C1—H11.073 (3)
N2—C11.377 (3)C4—H41.067 (4)
N2—C21.371 (4)C7—H71.076 (4)
Hydrogen-bond geometry (Å, º) for (CTZ_GEM_neutron_130K) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.995 (3)2.289 (4)2.884 (3)117.3 (3)
N2—H2···N3ii0.995 (3)2.489 (5)3.301 (3)138.6 (4)
N3—H3A···N1iii1.023 (4)2.154 (4)3.134 (3)159.9 (4)
N3—H3B···O2iv0.994 (3)2.396 (5)2.912 (3)111.5 (3)
N3—H3B···O4v0.994 (3)2.079 (4)2.993 (3)152.0 (4)
Symmetry codes: (i) x, y+1, z; (ii) x, y+1, z1; (iii) x1, y, z+1; (iv) x, y, z+1; (v) x+1, y, z.
Selected bond lengths (Å) for (HCT_GEM_neutron_295K) top
Cl1—C61.730 (2)N2—H21.005 (3)
S1—O11.439 (3)N3—H3A1.007 (3)
S1—O21.428 (3)N3—H3B1.005 (3)
S1—N11.6375 (16)C2—C31.394 (2)
S1—C31.759 (2)C2—C71.390 (2)
S2—O31.435 (3)C3—C41.382 (3)
S2—O41.428 (3)C4—C51.389 (2)
S2—N31.595 (2)C5—C61.387 (2)
S2—C51.759 (2)C6—C71.381 (2)
N1—C11.460 (2)C1—H1A1.088 (2)
N2—C11.463 (2)C1—H1B1.089 (2)
N2—C21.410 (2)C4—H41.083 (4)
N1—H51.003 (2)C7—H71.080 (3)
Hydrogen-bond geometry (Å, º) for (HCT_GEM_neutron_295K) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O3i1.005 (3)1.971 (4)2.940 (3)160.9 (3)
N3—H3A···Cl11.007 (3)2.746 (5)3.292 (3)114.4 (3)
N3—H3A···N1ii1.007 (3)2.233 (3)3.148 (2)150.4 (3)
N3—H3B···O3iii1.005 (3)2.240 (4)3.122 (4)145.8 (5)
N3—H3B···O4iii1.005 (3)2.593 (8)3.357 (3)132.8 (5)
N1—H5···O1iv1.003 (2)1.906 (4)2.901 (4)171.1 (3)
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x+1, y+1/2, z+1/2; (iii) x+1, y1/2, z+3/2; (iv) x, y, z+1.
 

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