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The crystal structure of the high-pressure polymorph (α′) of an antidiabetic drug, chlorpropamide [4-chloro-N-(propylaminocarbonyl)benzenesulfonamide, C10H13ClN2O3S], which is formed at ∼ 2.8 GPa from the α-polymorph (P212121) on hydrostatic compression in saturated ethanol solution, has been determined. As a result of the phase transition, the a, c and α parameters change jumpwise, whereas the changes in b parameter are continuous through the phase transition point. The high-pressure form is monoclinic (P2111) and has Z′ equal to 2, the two independent molecules differing in their conformations. The hydrogen bonds expand slightly in the high-pressure polymorph after the transition, and this expansion is interrelated with the changes in molecular conformations enabling a denser packing. The transition is reversible, but the crystal quality deteriorates as a result of multiple compression–decompression cycles, and a pseudomerohedral twinning accompanies the transformation.
Supporting information
CCDC references: 924555; 924556; 924557; 924558; 924559; 924560
For all compounds, data collection: CrysAlis CCD (Oxford Diffraction,2009); cell refinement: CrysAlis RED (Oxford Diffraction,2009); data reduction: CrysAlis RED (Oxford Diffraction,2009); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008).
(1.18GPa) 4-chloro-
N-((propylaminocarbonyl)benzenesulfonamide
top
Crystal data top
C10H13ClN2O3S | Dx = 1.615 Mg m−3 |
Mr = 276.73 | Melting point: phase transition K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 3797 reflections |
a = 26.573 (2) Å | θ = 2.3–30.9° |
b = 4.8587 (2) Å | µ = 0.52 mm−1 |
c = 8.8165 (4) Å | T = 293 K |
V = 1138.30 (11) Å3 | Plate, colorless |
Z = 4 | 0.22 × 0.11 × 0.04 mm |
F(000) = 576 | |
Data collection top
Oxford Diffraction KM4 CCD diffractometer | 896 independent reflections |
Radiation source: fine-focus sealed tube | 608 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.095 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 26.4°, θmin = 2.4° |
ω scans | h = −10→10 |
Absorption correction: numerical Absorb6.1 (Angel, 2006) | k = −6→6 |
Tmin = 0.331, Tmax = 0.468 | l = −11→11 |
9661 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.117 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0657P)2] where P = (Fo2 + 2Fc2)/3 |
896 reflections | (Δ/σ)max < 0.001 |
73 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
Crystal data top
C10H13ClN2O3S | V = 1138.30 (11) Å3 |
Mr = 276.73 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 26.573 (2) Å | µ = 0.52 mm−1 |
b = 4.8587 (2) Å | T = 293 K |
c = 8.8165 (4) Å | 0.22 × 0.11 × 0.04 mm |
Data collection top
Oxford Diffraction KM4 CCD diffractometer | 896 independent reflections |
Absorption correction: numerical Absorb6.1 (Angel, 2006) | 608 reflections with I > 2σ(I) |
Tmin = 0.331, Tmax = 0.468 | Rint = 0.095 |
9661 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.117 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.20 e Å−3 |
896 reflections | Δρmin = −0.17 e Å−3 |
73 parameters | |
Special details top
Experimental. high pressure measurement at 1.18 GPa in the DAC |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.0358 (3) | 0.7695 (7) | 0.4828 (5) | 0.0409 (17)* | |
C2 | 0.0410 (3) | 0.6043 (8) | 0.6106 (5) | 0.0439 (19)* | |
H2 | 0.0168 | 0.6095 | 0.6866 | 0.053* | |
C3 | 0.0824 (3) | 0.4315 (8) | 0.6247 (4) | 0.0392 (19)* | |
H3 | 0.0859 | 0.3210 | 0.7102 | 0.047* | |
C4 | 0.1187 (3) | 0.4238 (8) | 0.5111 (5) | 0.0348 (17)* | |
C5 | 0.1135 (3) | 0.5889 (8) | 0.3833 (4) | 0.0372 (17)* | |
H5 | 0.1377 | 0.5838 | 0.3073 | 0.045* | |
C6 | 0.0721 (3) | 0.7618 (7) | 0.3692 (4) | 0.0387 (18)* | |
H6 | 0.0686 | 0.8723 | 0.2837 | 0.046* | |
C7 | 0.2445 (7) | 0.5785 (10) | 0.5137 (7) | 0.0344 (16)* | |
C8 | 0.3046 (7) | 0.9436 (12) | 0.5339 (7) | 0.0355 (17)* | |
H81 | 0.3042 | 1.1020 | 0.6008 | 0.043* | |
H82 | 0.2907 | 1.0005 | 0.4371 | 0.043* | |
C9 | 0.3608 (8) | 0.8504 (12) | 0.5094 (8) | 0.046 (2)* | |
H91 | 0.3734 | 0.7708 | 0.6029 | 0.055* | |
H92 | 0.3618 | 0.7085 | 0.4321 | 0.055* | |
C10 | 0.3952 (7) | 1.0843 (13) | 0.4623 (9) | 0.054 (2)* | |
H101 | 0.3867 | 1.1425 | 0.3614 | 0.082* | |
H102 | 0.4295 | 1.0228 | 0.4644 | 0.082* | |
H103 | 0.3911 | 1.2358 | 0.5311 | 0.082* | |
Cl1 | −0.0150 (2) | 0.9816 (3) | 0.4631 (2) | 0.062 (3) | |
N1 | 0.2144 (5) | 0.3941 (8) | 0.5946 (5) | 0.0339 (15)* | |
H10 | 0.2206 | 0.3795 | 0.6901 | 0.041* | |
N2 | 0.2739 (5) | 0.7384 (8) | 0.5954 (5) | 0.0363 (14)* | |
H20 | 0.2743 | 0.7151 | 0.6921 | 0.044* | |
O1 | 0.1594 (4) | 0.0105 (7) | 0.6468 (4) | 0.0349 (11)* | |
O2 | 0.1836 (4) | 0.1098 (6) | 0.3801 (4) | 0.0373 (12)* | |
O3 | 0.2414 (4) | 0.5879 (6) | 0.3707 (4) | 0.046 (7) | |
S1 | 0.16927 (16) | 0.2042 (3) | 0.52859 (17) | 0.033 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.037 (11) | 0.0628 (11) | 0.0856 (14) | 0.018 (2) | −0.002 (2) | 0.0032 (11) |
O3 | 0.06 (2) | 0.038 (2) | 0.037 (2) | −0.006 (4) | 0.000 (4) | −0.0009 (18) |
S1 | 0.032 (7) | 0.0297 (7) | 0.0368 (8) | −0.0043 (15) | 0.0052 (16) | −0.0020 (7) |
Geometric parameters (Å, º) top
C1—C2 | 1.3900 | C8—N2 | 1.397 (14) |
C1—C6 | 1.3900 | C8—C9 | 1.58 (3) |
C1—Cl1 | 1.708 (8) | C8—H81 | 0.9700 |
C2—C3 | 1.3900 | C8—H82 | 0.9700 |
C2—H2 | 0.9300 | C9—C10 | 1.516 (18) |
C3—C4 | 1.3900 | C9—H91 | 0.9700 |
C3—H3 | 0.9300 | C9—H92 | 0.9700 |
C4—C5 | 1.3900 | C10—H101 | 0.9600 |
C4—S1 | 1.723 (7) | C10—H102 | 0.9600 |
C5—C6 | 1.3900 | C10—H103 | 0.9600 |
C5—H5 | 0.9300 | N1—S1 | 1.622 (12) |
C6—H6 | 0.9300 | N1—H10 | 0.8600 |
C7—O3 | 1.264 (7) | N2—H20 | 0.8600 |
C7—N2 | 1.318 (13) | O1—S1 | 1.429 (4) |
C7—N1 | 1.396 (13) | O2—S1 | 1.438 (5) |
| | | |
C2—C1—C6 | 120.0 | H81—C8—H82 | 107.7 |
C2—C1—Cl1 | 120.6 (3) | C10—C9—C8 | 113.2 (8) |
C6—C1—Cl1 | 119.4 (3) | C10—C9—H91 | 108.9 |
C3—C2—C1 | 120.0 | C8—C9—H91 | 108.9 |
C3—C2—H2 | 120.0 | C10—C9—H92 | 108.9 |
C1—C2—H2 | 120.0 | C8—C9—H92 | 108.9 |
C4—C3—C2 | 120.0 | H91—C9—H92 | 107.8 |
C4—C3—H3 | 120.0 | C9—C10—H101 | 109.5 |
C2—C3—H3 | 120.0 | C9—C10—H102 | 109.5 |
C5—C4—C3 | 120.0 | H101—C10—H102 | 109.5 |
C5—C4—S1 | 120.5 (3) | C9—C10—H103 | 109.5 |
C3—C4—S1 | 119.5 (3) | H101—C10—H103 | 109.5 |
C4—C5—C6 | 120.0 | H102—C10—H103 | 109.5 |
C4—C5—H5 | 120.0 | C7—N1—S1 | 127.2 (5) |
C6—C5—H5 | 120.0 | C7—N1—H10 | 116.4 |
C5—C6—C1 | 120.0 | S1—N1—H10 | 116.4 |
C5—C6—H6 | 120.0 | C7—N2—C8 | 123.7 (6) |
C1—C6—H6 | 120.0 | C7—N2—H20 | 118.1 |
O3—C7—N2 | 124.2 (9) | C8—N2—H20 | 118.1 |
O3—C7—N1 | 119.7 (10) | O1—S1—O2 | 120.2 (2) |
N2—C7—N1 | 116.0 (6) | O1—S1—N1 | 104.4 (3) |
N2—C8—C9 | 113.7 (7) | O2—S1—N1 | 108.2 (6) |
N2—C8—H81 | 108.8 | O1—S1—C4 | 109.2 (4) |
C9—C8—H81 | 108.8 | O2—S1—C4 | 108.8 (4) |
N2—C8—H82 | 108.8 | N1—S1—C4 | 104.9 (4) |
C9—C8—H82 | 108.8 | | |
| | | |
C6—C1—C2—C3 | 0.0 | O3—C7—N2—C8 | 1.7 (17) |
Cl1—C1—C2—C3 | 179.6 (4) | N1—C7—N2—C8 | −176.8 (11) |
C1—C2—C3—C4 | 0.0 | C9—C8—N2—C7 | −97.3 (12) |
C2—C3—C4—C5 | 0.0 | C7—N1—S1—O1 | 166.6 (9) |
C2—C3—C4—S1 | −178.9 (3) | C7—N1—S1—O2 | 37.5 (11) |
C3—C4—C5—C6 | 0.0 | C7—N1—S1—C4 | −78.5 (10) |
S1—C4—C5—C6 | 178.9 (3) | C5—C4—S1—O1 | −165.1 (3) |
C4—C5—C6—C1 | 0.0 | C3—C4—S1—O1 | 13.8 (4) |
C2—C1—C6—C5 | 0.0 | C5—C4—S1—O2 | −32.1 (5) |
Cl1—C1—C6—C5 | −179.6 (4) | C3—C4—S1—O2 | 146.8 (4) |
N2—C8—C9—C10 | −172.5 (7) | C5—C4—S1—N1 | 83.5 (3) |
O3—C7—N1—S1 | −7.9 (16) | C3—C4—S1—N1 | −97.6 (3) |
N2—C7—N1—S1 | 170.6 (9) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H10···O3i | 0.86 | 1.89 | 2.704 (10) | 157 |
N2—H20···O2i | 0.86 | 2.17 | 2.850 (9) | 135 |
N2—H20···O3i | 0.86 | 2.20 | 2.927 (6) | 143 |
Symmetry code: (i) −x+1/2, −y+1, z+1/2. |
(acpa_2.10GPa) 4-chloro-
N-((propylaminocarbonyl)benzenesulfonamide
top
Crystal data top
C10H13ClN2O3S | Dx = 1.697 Mg m−3 |
Mr = 276.73 | Melting point: phase transition K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 3931 reflections |
a = 26.5733 (18) Å | θ = 2.4–30.8° |
b = 4.7178 (2) Å | µ = 0.54 mm−1 |
c = 8.6406 (2) Å | T = 293 K |
V = 1083.25 (9) Å3 | Plate, colorless |
Z = 4 | 0.22 × 0.11 × 0.04 mm |
F(000) = 576 | |
Data collection top
Oxford Diffraction KM4 CCD diffractometer | 1040 independent reflections |
Radiation source: fine-focus sealed tube | 657 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.097 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 30.9°, θmin = 2.5° |
ω scans | h = −9→9 |
Absorption correction: numerical Absorb6.1 (R. J. Angel, 2006) | k = −6→6 |
Tmin = 0.328, Tmax = 0.468 | l = −12→12 |
10853 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0575P)2] where P = (Fo2 + 2Fc2)/3 |
1040 reflections | (Δ/σ)max < 0.001 |
63 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
Crystal data top
C10H13ClN2O3S | V = 1083.25 (9) Å3 |
Mr = 276.73 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 26.5733 (18) Å | µ = 0.54 mm−1 |
b = 4.7178 (2) Å | T = 293 K |
c = 8.6406 (2) Å | 0.22 × 0.11 × 0.04 mm |
Data collection top
Oxford Diffraction KM4 CCD diffractometer | 1040 independent reflections |
Absorption correction: numerical Absorb6.1 (R. J. Angel, 2006) | 657 reflections with I > 2σ(I) |
Tmin = 0.328, Tmax = 0.468 | Rint = 0.097 |
10853 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 0.97 | Δρmax = 0.18 e Å−3 |
1040 reflections | Δρmin = −0.18 e Å−3 |
63 parameters | |
Special details top
Experimental. high pressure measurement at 2.10 GPa in the DAC |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.0326 (2) | 0.7733 (6) | 0.4818 (4) | 0.0334 (13)* | |
C2 | 0.0380 (2) | 0.6011 (7) | 0.6112 (3) | 0.0399 (15)* | |
H2 | 0.0138 | 0.6036 | 0.6888 | 0.048* | |
C3 | 0.0798 (3) | 0.4251 (6) | 0.6247 (3) | 0.0341 (14)* | |
H3 | 0.0834 | 0.3099 | 0.7113 | 0.041* | |
C4 | 0.1160 (2) | 0.4213 (6) | 0.5088 (3) | 0.0236 (12)* | |
C5 | 0.1105 (2) | 0.5935 (6) | 0.3793 (3) | 0.0302 (13)* | |
H5 | 0.1348 | 0.5910 | 0.3018 | 0.036* | |
C6 | 0.0688 (3) | 0.7695 (6) | 0.3658 (3) | 0.0276 (13)* | |
H6 | 0.0652 | 0.8848 | 0.2792 | 0.033* | |
C7 | 0.2430 (6) | 0.5879 (8) | 0.5094 (5) | 0.0305 (13)* | |
C8 | 0.3051 (6) | 0.9560 (10) | 0.5285 (6) | 0.0284 (12)* | |
H8A | 0.3059 | 1.1206 | 0.5957 | 0.034* | |
H8B | 0.2917 | 1.0157 | 0.4293 | 0.034* | |
C9 | 0.3583 (7) | 0.8505 (11) | 0.5054 (6) | 0.0356 (16)* | |
H9A | 0.3699 | 0.7619 | 0.6001 | 0.043* | |
H9B | 0.3585 | 0.7080 | 0.4245 | 0.043* | |
C10 | 0.3931 (6) | 1.0835 (11) | 0.4626 (7) | 0.0448 (16)* | |
H10A | 0.3825 | 1.1664 | 0.3666 | 0.067* | |
H10B | 0.4266 | 1.0094 | 0.4514 | 0.067* | |
H10C | 0.3929 | 1.2254 | 0.5423 | 0.067* | |
Cl1 | −0.01768 (17) | 0.9872 (3) | 0.46112 (18) | 0.052 (3) | |
N1 | 0.2135 (5) | 0.4004 (7) | 0.5941 (4) | 0.0292 (11)* | |
H1 | 0.2197 | 0.3874 | 0.6915 | 0.035* | |
N2 | 0.2724 (4) | 0.7508 (7) | 0.5935 (4) | 0.0294 (11)* | |
H2A | 0.2717 | 0.7318 | 0.6924 | 0.035* | |
O1 | 0.1583 (3) | 0.0005 (6) | 0.6458 (3) | 0.0309 (9)* | |
O2 | 0.1821 (4) | 0.1067 (5) | 0.3748 (3) | 0.0319 (9)* | |
O3 | 0.2403 (4) | 0.5930 (5) | 0.3655 (3) | 0.0313 (9)* | |
S1 | 0.16792 (13) | 0.2017 (2) | 0.52666 (13) | 0.0271 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.031 (9) | 0.0540 (8) | 0.0697 (10) | 0.0101 (17) | −0.0096 (18) | 0.0034 (8) |
Geometric parameters (Å, º) top
C1—C2 | 1.3900 | C8—N2 | 1.417 (12) |
C1—C6 | 1.3900 | C8—C9 | 1.51 (2) |
C1—Cl1 | 1.683 (7) | C8—H8A | 0.9700 |
C2—C3 | 1.3900 | C8—H8B | 0.9700 |
C2—H2 | 0.9300 | C9—C10 | 1.484 (16) |
C3—C4 | 1.3900 | C9—H9A | 0.9700 |
C3—H3 | 0.9300 | C9—H9B | 0.9700 |
C4—C5 | 1.3900 | C10—H10A | 0.9600 |
C4—S1 | 1.732 (6) | C10—H10B | 0.9600 |
C5—C6 | 1.3900 | C10—H10C | 0.9600 |
C5—H5 | 0.9300 | N1—S1 | 1.638 (10) |
C6—H6 | 0.9300 | N1—H1 | 0.8600 |
C7—O3 | 1.246 (6) | N2—H2A | 0.8600 |
C7—N2 | 1.315 (11) | O1—S1 | 1.423 (3) |
C7—N1 | 1.390 (11) | O2—S1 | 1.437 (4) |
| | | |
C2—C1—C6 | 120.0 | H8A—C8—H8B | 107.7 |
C2—C1—Cl1 | 121.2 (2) | C10—C9—C8 | 111.9 (7) |
C6—C1—Cl1 | 118.8 (2) | C10—C9—H9A | 109.2 |
C3—C2—C1 | 120.0 | C8—C9—H9A | 109.2 |
C3—C2—H2 | 120.0 | C10—C9—H9B | 109.2 |
C1—C2—H2 | 120.0 | C8—C9—H9B | 109.2 |
C4—C3—C2 | 120.0 | H9A—C9—H9B | 107.9 |
C4—C3—H3 | 120.0 | C9—C10—H10A | 109.5 |
C2—C3—H3 | 120.0 | C9—C10—H10B | 109.5 |
C3—C4—C5 | 120.0 | H10A—C10—H10B | 109.5 |
C3—C4—S1 | 119.7 (2) | C9—C10—H10C | 109.5 |
C5—C4—S1 | 120.3 (2) | H10A—C10—H10C | 109.5 |
C6—C5—C4 | 120.0 | H10B—C10—H10C | 109.5 |
C6—C5—H5 | 120.0 | C7—N1—S1 | 126.4 (5) |
C4—C5—H5 | 120.0 | C7—N1—H1 | 116.8 |
C5—C6—C1 | 120.0 | S1—N1—H1 | 116.8 |
C5—C6—H6 | 120.0 | C7—N2—C8 | 123.0 (5) |
C1—C6—H6 | 120.0 | C7—N2—H2A | 118.5 |
O3—C7—N2 | 125.0 (8) | C8—N2—H2A | 118.5 |
O3—C7—N1 | 120.4 (8) | O1—S1—O2 | 119.96 (19) |
N2—C7—N1 | 114.6 (4) | O1—S1—N1 | 104.9 (3) |
N2—C8—C9 | 113.6 (5) | O2—S1—N1 | 108.0 (5) |
N2—C8—H8A | 108.8 | O1—S1—C4 | 108.7 (4) |
C9—C8—H8A | 108.8 | O2—S1—C4 | 108.3 (3) |
N2—C8—H8B | 108.8 | N1—S1—C4 | 106.1 (3) |
C9—C8—H8B | 108.8 | | |
| | | |
C6—C1—C2—C3 | 0.0 | O3—C7—N2—C8 | 0.2 (15) |
Cl1—C1—C2—C3 | 179.5 (3) | N1—C7—N2—C8 | −179.8 (9) |
C1—C2—C3—C4 | 0.0 | C9—C8—N2—C7 | −95.4 (11) |
C2—C3—C4—C5 | 0.0 | C7—N1—S1—O1 | 165.7 (8) |
C2—C3—C4—S1 | 179.9 (3) | C7—N1—S1—O2 | 36.7 (9) |
C3—C4—C5—C6 | 0.0 | C7—N1—S1—C4 | −79.3 (8) |
S1—C4—C5—C6 | −179.9 (3) | C3—C4—S1—O1 | 14.7 (3) |
C4—C5—C6—C1 | 0.0 | C5—C4—S1—O1 | −165.4 (2) |
C2—C1—C6—C5 | 0.0 | C3—C4—S1—O2 | 146.6 (3) |
Cl1—C1—C6—C5 | −179.6 (3) | C5—C4—S1—O2 | −33.5 (4) |
N2—C8—C9—C10 | −170.3 (5) | C3—C4—S1—N1 | −97.6 (3) |
O3—C7—N1—S1 | −8.8 (14) | C5—C4—S1—N1 | 82.3 (3) |
N2—C7—N1—S1 | 171.2 (7) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.86 | 1.84 | 2.648 (8) | 155 |
N2—H2A···O2i | 0.86 | 2.14 | 2.797 (7) | 133 |
N2—H2A···O3i | 0.86 | 2.16 | 2.875 (5) | 140 |
Symmetry code: (i) −x+1/2, −y+1, z+1/2. |
(acpa_2.50GPa) 4-chloro-
N-((propylaminocarbonyl)benzenesulfonamide
top
Crystal data top
C10H13ClN2O3S | Dx = 1.727 Mg m−3 |
Mr = 276.73 | Melting point: phase transition K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 4024 reflections |
a = 26.605 (2) Å | θ = 2.4–31.0° |
b = 4.6688 (2) Å | µ = 0.55 mm−1 |
c = 8.5711 (3) Å | T = 293 K |
V = 1064.65 (10) Å3 | Plate, colorless |
Z = 4 | 0.22 × 0.11 × 0.04 mm |
F(000) = 576 | |
Data collection top
Oxford Diffraction KM4 CCD diffractometer | 1030 independent reflections |
Radiation source: fine-focus sealed tube | 647 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.096 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 31.1°, θmin = 2.5° |
ω scans | h = −9→9 |
Absorption correction: numerical Absorb6.1 (R. J. Angel, 2006) | k = −6→6 |
Tmin = 0.323, Tmax = 0.468 | l = −12→12 |
10571 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.125 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0733P)2] where P = (Fo2 + 2Fc2)/3 |
1030 reflections | (Δ/σ)max < 0.001 |
58 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
Crystal data top
C10H13ClN2O3S | V = 1064.65 (10) Å3 |
Mr = 276.73 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 26.605 (2) Å | µ = 0.55 mm−1 |
b = 4.6688 (2) Å | T = 293 K |
c = 8.5711 (3) Å | 0.22 × 0.11 × 0.04 mm |
Data collection top
Oxford Diffraction KM4 CCD diffractometer | 1030 independent reflections |
Absorption correction: numerical Absorb6.1 (R. J. Angel, 2006) | 647 reflections with I > 2σ(I) |
Tmin = 0.323, Tmax = 0.468 | Rint = 0.096 |
10571 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.125 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.22 e Å−3 |
1030 reflections | Δρmin = −0.28 e Å−3 |
58 parameters | |
Special details top
Experimental. high pressure measurement at 2.50 GPa in the DAC |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.0319 (3) | 0.7754 (7) | 0.4811 (4) | 0.0289 (14)* | |
C2 | 0.0374 (3) | 0.6012 (8) | 0.6115 (4) | 0.0323 (15)* | |
H2 | 0.0131 | 0.6030 | 0.6896 | 0.039* | |
C3 | 0.0792 (3) | 0.4244 (7) | 0.6252 (3) | 0.0336 (16)* | |
H3 | 0.0829 | 0.3079 | 0.7124 | 0.040* | |
C4 | 0.1155 (3) | 0.4218 (7) | 0.5084 (4) | 0.0252 (14)* | |
C5 | 0.1099 (3) | 0.5959 (8) | 0.3780 (4) | 0.0276 (15)* | |
H5 | 0.1342 | 0.5941 | 0.2999 | 0.033* | |
C6 | 0.0681 (3) | 0.7727 (7) | 0.3643 (3) | 0.0256 (14)* | |
H6 | 0.0644 | 0.8892 | 0.2771 | 0.031* | |
C7 | 0.2412 (6) | 0.5920 (9) | 0.5072 (6) | 0.0253 (14)* | |
C8 | 0.3050 (7) | 0.9616 (11) | 0.5272 (7) | 0.0293 (14)* | |
H8A | 0.3065 | 1.1271 | 0.5955 | 0.035* | |
H8B | 0.2917 | 1.0248 | 0.4276 | 0.035* | |
C9 | 0.3581 (8) | 0.8474 (13) | 0.5028 (7) | 0.0367 (18)* | |
H9A | 0.3696 | 0.7540 | 0.5974 | 0.044* | |
H9B | 0.3580 | 0.7064 | 0.4197 | 0.044* | |
C10 | 0.3932 (7) | 1.0844 (13) | 0.4618 (8) | 0.0391 (17)* | |
H10A | 0.3822 | 1.1749 | 0.3673 | 0.059* | |
H10B | 0.4264 | 1.0084 | 0.4470 | 0.059* | |
H10C | 0.3937 | 1.2226 | 0.5447 | 0.059* | |
Cl1 | −0.01844 (19) | 0.9890 (3) | 0.46014 (19) | 0.0543 (6)* | |
N1 | 0.2127 (5) | 0.4020 (8) | 0.5924 (5) | 0.0277 (12)* | |
H1 | 0.2195 | 0.3874 | 0.6902 | 0.033* | |
N2 | 0.2717 (5) | 0.7590 (8) | 0.5920 (5) | 0.0260 (13)* | |
H2A | 0.2709 | 0.7415 | 0.6919 | 0.031* | |
O1 | 0.1581 (3) | −0.0027 (7) | 0.6449 (4) | 0.0287 (10)* | |
O2 | 0.1820 (4) | 0.1069 (7) | 0.3724 (4) | 0.0274 (10)* | |
O3 | 0.2381 (4) | 0.5973 (7) | 0.3631 (4) | 0.0305 (10)* | |
S1 | 0.16734 (16) | 0.2019 (3) | 0.52579 (15) | 0.0252 (4)* | |
Geometric parameters (Å, º) top
C1—C2 | 1.3900 | C8—N2 | 1.410 (15) |
C1—C6 | 1.3900 | C8—C9 | 1.53 (3) |
C1—Cl1 | 1.679 (7) | C8—H8A | 0.9700 |
C2—C3 | 1.3900 | C8—H8B | 0.9700 |
C2—H2 | 0.9300 | C9—C10 | 1.490 (18) |
C3—C4 | 1.3900 | C9—H9A | 0.9700 |
C3—H3 | 0.9300 | C9—H9B | 0.9700 |
C4—C5 | 1.3900 | C10—H10A | 0.9600 |
C4—S1 | 1.726 (7) | C10—H10B | 0.9600 |
C5—C6 | 1.3900 | C10—H10C | 0.9600 |
C5—H5 | 0.9300 | N1—S1 | 1.630 (12) |
C6—H6 | 0.9300 | N1—H1 | 0.8600 |
C7—O3 | 1.238 (7) | N2—H2A | 0.8600 |
C7—N2 | 1.340 (12) | O1—S1 | 1.419 (4) |
C7—N1 | 1.376 (13) | O2—S1 | 1.441 (5) |
| | | |
C2—C1—C6 | 120.0 | H8A—C8—H8B | 107.7 |
C2—C1—Cl1 | 121.2 (3) | C10—C9—C8 | 110.7 (8) |
C6—C1—Cl1 | 118.8 (3) | C10—C9—H9A | 109.5 |
C1—C2—C3 | 120.0 | C8—C9—H9A | 109.5 |
C1—C2—H2 | 120.0 | C10—C9—H9B | 109.5 |
C3—C2—H2 | 120.0 | C8—C9—H9B | 109.5 |
C2—C3—C4 | 120.0 | H9A—C9—H9B | 108.1 |
C2—C3—H3 | 120.0 | C9—C10—H10A | 109.5 |
C4—C3—H3 | 120.0 | C9—C10—H10B | 109.5 |
C5—C4—C3 | 120.0 | H10A—C10—H10B | 109.5 |
C5—C4—S1 | 120.1 (2) | C9—C10—H10C | 109.5 |
C3—C4—S1 | 119.9 (2) | H10A—C10—H10C | 109.5 |
C4—C5—C6 | 120.0 | H10B—C10—H10C | 109.5 |
C4—C5—H5 | 120.0 | C7—N1—S1 | 126.3 (5) |
C6—C5—H5 | 120.0 | C7—N1—H1 | 116.9 |
C5—C6—C1 | 120.0 | S1—N1—H1 | 116.9 |
C5—C6—H6 | 120.0 | C7—N2—C8 | 123.8 (5) |
C1—C6—H6 | 120.0 | C7—N2—H2A | 118.1 |
O3—C7—N2 | 124.7 (9) | C8—N2—H2A | 118.1 |
O3—C7—N1 | 120.4 (10) | O1—S1—O2 | 119.7 (2) |
N2—C7—N1 | 114.9 (5) | O1—S1—N1 | 105.2 (3) |
N2—C8—C9 | 113.7 (6) | O2—S1—N1 | 107.2 (6) |
N2—C8—H8A | 108.8 | O1—S1—C4 | 108.9 (4) |
C9—C8—H8A | 108.8 | O2—S1—C4 | 108.7 (4) |
N2—C8—H8B | 108.8 | N1—S1—C4 | 106.4 (4) |
C9—C8—H8B | 108.8 | | |
| | | |
C6—C1—C2—C3 | 0.0 | O3—C7—N2—C8 | −0.8 (17) |
Cl1—C1—C2—C3 | 179.4 (3) | N1—C7—N2—C8 | 178.1 (10) |
C1—C2—C3—C4 | 0.0 | C9—C8—N2—C7 | −94.5 (12) |
C2—C3—C4—C5 | 0.0 | C7—N1—S1—O1 | 166.1 (9) |
C2—C3—C4—S1 | 180.0 (3) | C7—N1—S1—O2 | 37.7 (10) |
C3—C4—C5—C6 | 0.0 | C7—N1—S1—C4 | −78.4 (9) |
S1—C4—C5—C6 | 180.0 (3) | C5—C4—S1—O1 | −165.2 (3) |
C4—C5—C6—C1 | 0.0 | C3—C4—S1—O1 | 14.8 (4) |
C2—C1—C6—C5 | 0.0 | C5—C4—S1—O2 | −33.2 (4) |
Cl1—C1—C6—C5 | −179.4 (3) | C3—C4—S1—O2 | 146.8 (4) |
N2—C8—C9—C10 | −169.7 (6) | C5—C4—S1—N1 | 81.9 (3) |
O3—C7—N1—S1 | −9.5 (16) | C3—C4—S1—N1 | −98.1 (3) |
N2—C7—N1—S1 | 171.5 (8) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.86 | 1.86 | 2.664 (11) | 154 |
N2—H2A···O2i | 0.86 | 2.11 | 2.772 (9) | 133 |
N2—H2A···O3i | 0.86 | 2.17 | 2.869 (5) | 138 |
Symmetry code: (i) −x+1/2, −y+1, z+1/2. |
(acpa_2.63GPa) 4-chloro-
N-((propylaminocarbonyl)benzenesulfonamide
top
Crystal data top
C10H13ClN2O3S | Dx = 1.734 Mg m−3 |
Mr = 276.73 | Melting point: phase transition K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 3821 reflections |
a = 26.6068 (19) Å | θ = 4.4–31.0° |
b = 4.6576 (2) Å | µ = 0.56 mm−1 |
c = 8.5556 (2) Å | T = 293 K |
V = 1060.24 (9) Å3 | Plate, colorless |
Z = 4 | 0.22 × 0.11 × 0.04 mm |
F(000) = 576 | |
Data collection top
Oxford Diffraction KM4 CCD diffractometer | 1025 independent reflections |
Radiation source: fine-focus sealed tube | 656 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.095 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 31.1°, θmin = 2.5° |
ω scans | h = −9→9 |
Absorption correction: numerical Absorb6.1 (R. J. Angel, 2006) | k = −6→6 |
Tmin = 0.323, Tmax = 0.468 | l = −12→12 |
10572 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.057P)2] where P = (Fo2 + 2Fc2)/3 |
1025 reflections | (Δ/σ)max < 0.001 |
63 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
Crystal data top
C10H13ClN2O3S | V = 1060.24 (9) Å3 |
Mr = 276.73 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 26.6068 (19) Å | µ = 0.56 mm−1 |
b = 4.6576 (2) Å | T = 293 K |
c = 8.5556 (2) Å | 0.22 × 0.11 × 0.04 mm |
Data collection top
Oxford Diffraction KM4 CCD diffractometer | 1025 independent reflections |
Absorption correction: numerical Absorb6.1 (R. J. Angel, 2006) | 656 reflections with I > 2σ(I) |
Tmin = 0.323, Tmax = 0.468 | Rint = 0.095 |
10572 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.21 e Å−3 |
1025 reflections | Δρmin = −0.26 e Å−3 |
63 parameters | |
Special details top
Experimental. high pressure measurement at 2.63 GPa in the DAC |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.0315 (2) | 0.7770 (6) | 0.4812 (4) | 0.0297 (13)* | |
C2 | 0.0371 (3) | 0.6020 (7) | 0.6117 (3) | 0.0330 (14)* | |
H2 | 0.0128 | 0.6034 | 0.6899 | 0.040* | |
C3 | 0.0789 (3) | 0.4249 (6) | 0.6252 (3) | 0.0322 (14)* | |
H3 | 0.0826 | 0.3078 | 0.7125 | 0.039* | |
C4 | 0.1152 (2) | 0.4228 (7) | 0.5083 (3) | 0.0260 (13)* | |
C5 | 0.1096 (3) | 0.5978 (7) | 0.3778 (3) | 0.0267 (13)* | |
H5 | 0.1339 | 0.5965 | 0.2996 | 0.032* | |
C6 | 0.0678 (3) | 0.7750 (6) | 0.3643 (3) | 0.0247 (12)* | |
H6 | 0.0641 | 0.8921 | 0.2770 | 0.030* | |
C7 | 0.2417 (6) | 0.5921 (8) | 0.5066 (5) | 0.0262 (13)* | |
C8 | 0.3056 (6) | 0.9646 (10) | 0.5257 (6) | 0.0273 (12)* | |
H8A | 0.3073 | 1.1307 | 0.5939 | 0.033* | |
H8B | 0.2924 | 1.0279 | 0.4257 | 0.033* | |
C9 | 0.3568 (7) | 0.8494 (11) | 0.5027 (6) | 0.0325 (15)* | |
H9A | 0.3562 | 0.7081 | 0.4195 | 0.039* | |
H9B | 0.3676 | 0.7533 | 0.5976 | 0.039* | |
C10 | 0.3949 (6) | 1.0834 (11) | 0.4616 (6) | 0.0371 (15)* | |
H10A | 0.3848 | 1.1769 | 0.3666 | 0.056* | |
H10B | 0.4274 | 0.9987 | 0.4476 | 0.056* | |
H10C | 0.3962 | 1.2217 | 0.5447 | 0.056* | |
Cl1 | −0.01897 (17) | 0.9897 (3) | 0.45995 (17) | 0.053 (3) | |
N1 | 0.2118 (5) | 0.4010 (7) | 0.5922 (4) | 0.0261 (11)* | |
H1 | 0.2178 | 0.3889 | 0.6908 | 0.031* | |
N2 | 0.2716 (4) | 0.7597 (7) | 0.5918 (4) | 0.0260 (11)* | |
H2A | 0.2705 | 0.7439 | 0.6919 | 0.031* | |
O1 | 0.1579 (3) | −0.0025 (6) | 0.6454 (3) | 0.0286 (9)* | |
O2 | 0.1807 (4) | 0.1067 (6) | 0.3720 (3) | 0.0279 (9)* | |
O3 | 0.2390 (4) | 0.5970 (6) | 0.3625 (4) | 0.0293 (9)* | |
S1 | 0.16730 (14) | 0.2019 (2) | 0.52509 (13) | 0.0245 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.052 (9) | 0.0489 (8) | 0.0595 (9) | 0.0100 (17) | −0.0105 (17) | 0.0042 (7) |
Geometric parameters (Å, º) top
C1—C2 | 1.3900 | C8—N2 | 1.430 (13) |
C1—C6 | 1.3900 | C8—C9 | 1.48 (2) |
C1—Cl1 | 1.679 (6) | C8—H8A | 0.9700 |
C2—C3 | 1.3900 | C8—H8B | 0.9700 |
C2—H2 | 0.9300 | C9—C10 | 1.528 (16) |
C3—C4 | 1.3900 | C9—H9A | 0.9700 |
C3—H3 | 0.9300 | C9—H9B | 0.9700 |
C4—C5 | 1.3900 | C10—H10A | 0.9600 |
C4—S1 | 1.733 (6) | C10—H10B | 0.9600 |
C5—C6 | 1.3900 | C10—H10C | 0.9600 |
C5—H5 | 0.9300 | N1—S1 | 1.609 (10) |
C6—H6 | 0.9300 | N1—H1 | 0.8600 |
C7—O3 | 1.235 (6) | N2—H2A | 0.8600 |
C7—N2 | 1.333 (11) | O1—S1 | 1.425 (4) |
C7—N1 | 1.401 (11) | O2—S1 | 1.428 (4) |
| | | |
C2—C1—C6 | 120.0 | H8A—C8—H8B | 107.8 |
C2—C1—Cl1 | 121.2 (2) | C8—C9—C10 | 112.5 (7) |
C6—C1—Cl1 | 118.8 (2) | C8—C9—H9A | 109.1 |
C3—C2—C1 | 120.0 | C10—C9—H9A | 109.1 |
C3—C2—H2 | 120.0 | C8—C9—H9B | 109.1 |
C1—C2—H2 | 120.0 | C10—C9—H9B | 109.1 |
C4—C3—C2 | 120.0 | H9A—C9—H9B | 107.8 |
C4—C3—H3 | 120.0 | C9—C10—H10A | 109.5 |
C2—C3—H3 | 120.0 | C9—C10—H10B | 109.5 |
C3—C4—C5 | 120.0 | H10A—C10—H10B | 109.5 |
C3—C4—S1 | 120.0 (2) | C9—C10—H10C | 109.5 |
C5—C4—S1 | 120.0 (2) | H10A—C10—H10C | 109.5 |
C4—C5—C6 | 120.0 | H10B—C10—H10C | 109.5 |
C4—C5—H5 | 120.0 | C7—N1—S1 | 126.7 (5) |
C6—C5—H5 | 120.0 | C7—N1—H1 | 116.7 |
C5—C6—C1 | 120.0 | S1—N1—H1 | 116.7 |
C5—C6—H6 | 120.0 | C7—N2—C8 | 123.5 (5) |
C1—C6—H6 | 120.0 | C7—N2—H2A | 118.3 |
O3—C7—N2 | 124.7 (8) | C8—N2—H2A | 118.3 |
O3—C7—N1 | 120.1 (8) | O1—S1—O2 | 119.9 (2) |
N2—C7—N1 | 115.2 (4) | O1—S1—N1 | 104.8 (3) |
N2—C8—C9 | 113.1 (5) | O2—S1—N1 | 108.9 (5) |
N2—C8—H8A | 108.9 | O1—S1—C4 | 108.5 (4) |
C9—C8—H8A | 108.9 | O2—S1—C4 | 107.9 (3) |
N2—C8—H8B | 108.9 | N1—S1—C4 | 106.0 (3) |
C9—C8—H8B | 108.9 | | |
| | | |
C6—C1—C2—C3 | 0.0 | O3—C7—N2—C8 | −1.4 (15) |
Cl1—C1—C2—C3 | 179.1 (3) | N1—C7—N2—C8 | 178.9 (9) |
C1—C2—C3—C4 | 0.0 | C9—C8—N2—C7 | −93.7 (11) |
C2—C3—C4—C5 | 0.0 | C7—N1—S1—O1 | 165.1 (8) |
C2—C3—C4—S1 | −180.0 (3) | C7—N1—S1—O2 | 35.6 (9) |
C3—C4—C5—C6 | 0.0 | C7—N1—S1—C4 | −80.3 (8) |
S1—C4—C5—C6 | 180.0 (3) | C3—C4—S1—O1 | 14.4 (3) |
C4—C5—C6—C1 | 0.0 | C5—C4—S1—O1 | −165.5 (3) |
C2—C1—C6—C5 | 0.0 | C3—C4—S1—O2 | 145.8 (3) |
Cl1—C1—C6—C5 | −179.1 (3) | C5—C4—S1—O2 | −34.2 (4) |
N2—C8—C9—C10 | −169.2 (5) | C3—C4—S1—N1 | −97.7 (3) |
O3—C7—N1—S1 | −8.1 (14) | C5—C4—S1—N1 | 82.3 (3) |
N2—C7—N1—S1 | 171.7 (7) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.86 | 1.87 | 2.657 (9) | 152 |
N2—H2A···O2i | 0.86 | 2.13 | 2.782 (8) | 132 |
N2—H2A···O3i | 0.86 | 2.17 | 2.864 (5) | 137 |
Symmetry code: (i) −x+1/2, −y+1, z+1/2. |
(acpa_2.91GPa) 4-chloro-
N-((propylaminocarbonyl)benzenesulfonamide
top
Crystal data top
C10H13ClN2O3S | F(000) = 576 |
Mr = 276.73 | Dx = 1.773 Mg m−3 |
Monoclinic, P2111 | Melting point: phase transition K |
Hall symbol: P 2xa | Mo Kα radiation, λ = 0.71073 Å |
a = 25.602 (3) Å | Cell parameters from 3109 reflections |
b = 4.6340 (2) Å | θ = 2.3–31.2° |
c = 8.8525 (4) Å | µ = 0.57 mm−1 |
β = 90° | T = 293 K |
V = 1037.01 (14) Å3 | Plate, colorless |
Z = 4 | 0.22 × 0.11 × 0.04 mm |
Data collection top
Oxford Diffraction KM4 CCD diffractometer | 1745 independent reflections |
Radiation source: fine-focus sealed tube | 1083 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.113 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 31.3°, θmin = 2.3° |
ω scans | h = −8→8 |
Absorption correction: numerical Absorb6.1 (R. J. Angel, 2006) | k = −6→6 |
Tmin = 0.331, Tmax = 0.468 | l = −12→12 |
10171 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.144 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0756P)2] where P = (Fo2 + 2Fc2)/3 |
1745 reflections | (Δ/σ)max < 0.001 |
115 parameters | Δρmax = 0.28 e Å−3 |
3 restraints | Δρmin = −0.30 e Å−3 |
Crystal data top
C10H13ClN2O3S | V = 1037.01 (14) Å3 |
Mr = 276.73 | Z = 4 |
Monoclinic, P2111 | Mo Kα radiation |
a = 25.602 (3) Å | µ = 0.57 mm−1 |
b = 4.6340 (2) Å | T = 293 K |
c = 8.8525 (4) Å | 0.22 × 0.11 × 0.04 mm |
β = 90° | |
Data collection top
Oxford Diffraction KM4 CCD diffractometer | 1745 independent reflections |
Absorption correction: numerical Absorb6.1 (R. J. Angel, 2006) | 1083 reflections with I > 2σ(I) |
Tmin = 0.331, Tmax = 0.468 | Rint = 0.113 |
10171 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.068 | 3 restraints |
wR(F2) = 0.144 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.28 e Å−3 |
1745 reflections | Δρmin = −0.30 e Å−3 |
115 parameters | |
Special details top
Experimental. high pressure measurement at 2.91 GPa in the DAC |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.8869 (5) | 1.0502 (11) | 0.4560 (6) | 0.025 (2)* | |
C2 | 0.8761 (5) | 0.8810 (12) | 0.3153 (5) | 0.024 (2)* | |
H2 | 0.8957 | 0.9048 | 0.2298 | 0.028* | |
C3 | 0.8360 (6) | 0.6763 (12) | 0.3026 (5) | 0.026 (2)* | |
H3 | 0.8288 | 0.5631 | 0.2085 | 0.031* | |
C4 | 0.8067 (5) | 0.6408 (11) | 0.4305 (6) | 0.021 (2)* | |
C5 | 0.8175 (5) | 0.8100 (12) | 0.5712 (5) | 0.022 (2)* | |
H5 | 0.7979 | 0.7862 | 0.6568 | 0.027* | |
C6 | 0.8576 (5) | 1.0147 (11) | 0.5839 (5) | 0.018 (2)* | |
H6 | 0.8648 | 1.1279 | 0.6780 | 0.022* | |
C7 | 0.6768 (11) | 0.7946 (16) | 0.4617 (8) | 0.018 (2)* | |
C8 | 0.6123 (11) | 1.1696 (17) | 0.4766 (9) | 0.024 (2)* | |
H8A | 0.6022 | 1.3149 | 0.4143 | 0.029* | |
H8B | 0.6306 | 1.2702 | 0.5655 | 0.029* | |
C9 | 0.5623 (12) | 1.0296 (19) | 0.5309 (10) | 0.025 (2)* | |
H9A | 0.5503 | 0.8761 | 0.4509 | 0.030* | |
H9B | 0.5704 | 0.9414 | 0.6204 | 0.030* | |
C10 | 0.5184 (12) | 1.2560 (19) | 0.5703 (11) | 0.036 (3)* | |
H10A | 0.5016 | 1.2905 | 0.4779 | 0.054* | |
H10B | 0.5330 | 1.4356 | 0.6222 | 0.054* | |
H10C | 0.4933 | 1.1832 | 0.6355 | 0.054* | |
Cl1 | 0.9333 (3) | 1.3165 (5) | 0.4713 (3) | 0.0375 (7)* | |
N1 | 0.7079 (8) | 0.5973 (13) | 0.3636 (7) | 0.0177 (18)* | |
H1N | 0.7011 | 0.5794 | 0.2674 | 0.021* | |
N2 | 0.6471 (8) | 0.9693 (13) | 0.3911 (8) | 0.024 (2)* | |
H2N | 0.6491 | 0.9601 | 0.2935 | 0.028* | |
O1 | 0.7633 (7) | 0.1880 (11) | 0.2819 (6) | 0.0250 (16)* | |
O2 | 0.7451 (7) | 0.3207 (12) | 0.5580 (6) | 0.0251 (15)* | |
O3 | 0.6755 (7) | 0.8032 (10) | 0.6031 (5) | 0.0201 (15)* | |
S1 | 0.7539 (3) | 0.4055 (5) | 0.4116 (2) | 0.0210 (6)* | |
C21 | 0.4621 (5) | 0.5225 (11) | 1.0684 (6) | 0.015 (2)* | |
C22 | 0.4626 (5) | 0.6415 (11) | 0.9338 (6) | 0.028 (2)* | |
H22 | 0.4358 | 0.5991 | 0.8630 | 0.034* | |
C23 | 0.5033 (5) | 0.8237 (11) | 0.9049 (5) | 0.026 (2)* | |
H23 | 0.5037 | 0.9033 | 0.8148 | 0.032* | |
C24 | 0.5435 (5) | 0.8870 (11) | 1.0106 (6) | 0.018 (2)* | |
C25 | 0.5429 (4) | 0.7681 (11) | 1.1452 (6) | 0.026 (2)* | |
H25 | 0.5698 | 0.8104 | 1.2160 | 0.031* | |
C26 | 0.5023 (5) | 0.5858 (11) | 1.1741 (5) | 0.025 (2)* | |
H26 | 0.5019 | 0.5063 | 1.2642 | 0.030* | |
C27 | 0.6720 (10) | 0.7031 (16) | 0.9529 (8) | 0.020 (2)* | |
C28 | 0.7343 (9) | 0.301 (2) | 0.9021 (9) | 0.025 (2)* | |
H28A | 0.7337 | 0.1263 | 0.8256 | 0.030* | |
H28B | 0.7223 | 0.2467 | 0.9976 | 0.030* | |
C29 | 0.7893 (8) | 0.4030 (18) | 0.9228 (9) | 0.015 (2)* | |
H29A | 0.7904 | 0.5747 | 1.0013 | 0.018* | |
H29B | 0.8016 | 0.4599 | 0.8281 | 0.018* | |
C30 | 0.8261 (9) | 0.1709 (16) | 0.9680 (9) | 0.024 (2)* | |
H30A | 0.8250 | −0.0005 | 0.8913 | 0.035* | |
H30B | 0.8154 | 0.1214 | 1.0646 | 0.035* | |
H30C | 0.8611 | 0.2462 | 0.9764 | 0.035* | |
Cl2 | 0.4137 (3) | 0.2990 (5) | 1.1067 (3) | 0.0404 (8)* | |
N21 | 0.6377 (8) | 0.8833 (13) | 0.8871 (7) | 0.0212 (18)* | |
H21N | 0.6392 | 0.8757 | 0.7895 | 0.025* | |
N22 | 0.6971 (8) | 0.5124 (13) | 0.8556 (7) | 0.0171 (18)* | |
H22N | 0.6916 | 0.5097 | 0.7595 | 0.020* | |
O21 | 0.5801 (7) | 1.2851 (11) | 0.8728 (6) | 0.0246 (16)* | |
O22 | 0.6166 (7) | 1.2309 (11) | 1.1248 (6) | 0.0228 (15)* | |
O23 | 0.6761 (8) | 0.7281 (12) | 1.0906 (6) | 0.0297 (17)* | |
S2 | 0.5957 (3) | 1.1040 (4) | 0.9792 (2) | 0.0186 (6)* | |
Geometric parameters (Å, º) top
C1—C2 | 1.3900 | C21—C22 | 1.3900 |
C1—C6 | 1.3900 | C21—C26 | 1.3900 |
C1—Cl1 | 1.703 (11) | C21—Cl2 | 1.684 (11) |
C2—C3 | 1.3900 | C22—C23 | 1.3900 |
C2—H2 | 0.9300 | C22—H22 | 0.9300 |
C3—C4 | 1.3900 | C23—C24 | 1.3900 |
C3—H3 | 0.9300 | C23—H23 | 0.9300 |
C4—C5 | 1.3900 | C24—C25 | 1.3900 |
C4—S1 | 1.728 (11) | C24—S2 | 1.722 (11) |
C5—C6 | 1.3900 | C25—C26 | 1.3900 |
C5—H5 | 0.9300 | C25—H25 | 0.9300 |
C6—H6 | 0.9300 | C26—H26 | 0.9300 |
C7—O3 | 1.246 (9) | C27—O23 | 1.210 (9) |
C7—N2 | 1.34 (2) | C27—N22 | 1.301 (18) |
C7—N1 | 1.41 (2) | C27—N21 | 1.40 (2) |
C8—N2 | 1.42 (2) | C28—N22 | 1.47 (2) |
C8—C9 | 1.55 (4) | C28—C29 | 1.487 (18) |
C8—H8A | 0.9700 | C28—H28A | 0.9700 |
C8—H8B | 0.9700 | C28—H28B | 0.9700 |
C9—C10 | 1.54 (3) | C29—C30 | 1.530 (16) |
C9—H9A | 0.9700 | C29—H29A | 0.9700 |
C9—H9B | 0.9700 | C29—H29B | 0.9700 |
C10—H10A | 0.9600 | C30—H30A | 0.9600 |
C10—H10B | 0.9600 | C30—H30B | 0.9600 |
C10—H10C | 0.9600 | C30—H30C | 0.9600 |
N1—S1 | 1.574 (17) | N21—S2 | 1.614 (15) |
N1—H1N | 0.8600 | N21—H21N | 0.8600 |
N2—H2N | 0.8600 | N22—H22N | 0.8600 |
O1—S1 | 1.423 (7) | O21—S2 | 1.415 (7) |
O2—S1 | 1.431 (6) | O22—S2 | 1.433 (9) |
| | | |
C2—C1—C6 | 120.0 | C22—C21—C26 | 120.0 |
C2—C1—Cl1 | 120.6 (3) | C22—C21—Cl2 | 121.3 (4) |
C6—C1—Cl1 | 119.3 (3) | C26—C21—Cl2 | 118.7 (4) |
C1—C2—C3 | 120.0 | C23—C22—C21 | 120.0 |
C1—C2—H2 | 120.0 | C23—C22—H22 | 120.0 |
C3—C2—H2 | 120.0 | C21—C22—H22 | 120.0 |
C4—C3—C2 | 120.0 | C24—C23—C22 | 120.0 |
C4—C3—H3 | 120.0 | C24—C23—H23 | 120.0 |
C2—C3—H3 | 120.0 | C22—C23—H23 | 120.0 |
C5—C4—C3 | 120.0 | C23—C24—C25 | 120.0 |
C5—C4—S1 | 120.0 (4) | C23—C24—S2 | 122.1 (4) |
C3—C4—S1 | 119.8 (4) | C25—C24—S2 | 117.8 (4) |
C4—C5—C6 | 120.0 | C26—C25—C24 | 120.0 |
C4—C5—H5 | 120.0 | C26—C25—H25 | 120.0 |
C6—C5—H5 | 120.0 | C24—C25—H25 | 120.0 |
C5—C6—C1 | 120.0 | C25—C26—C21 | 120.0 |
C5—C6—H6 | 120.0 | C25—C26—H26 | 120.0 |
C1—C6—H6 | 120.0 | C21—C26—H26 | 120.0 |
O3—C7—N2 | 122.0 (15) | O23—C27—N22 | 124.8 (16) |
O3—C7—N1 | 123.4 (14) | O23—C27—N21 | 120.3 (14) |
N2—C7—N1 | 114.6 (7) | N22—C27—N21 | 114.9 (8) |
N2—C8—C9 | 114.5 (10) | N22—C28—C29 | 115.8 (11) |
N2—C8—H8A | 108.6 | N22—C28—H28A | 108.3 |
C9—C8—H8A | 108.6 | C29—C28—H28A | 108.3 |
N2—C8—H8B | 108.6 | N22—C28—H28B | 108.3 |
C9—C8—H8B | 108.6 | C29—C28—H28B | 108.3 |
H8A—C8—H8B | 107.6 | H28A—C28—H28B | 107.4 |
C10—C9—C8 | 111.7 (11) | C28—C29—C30 | 113.1 (11) |
C10—C9—H9A | 109.3 | C28—C29—H29A | 109.0 |
C8—C9—H9A | 109.3 | C30—C29—H29A | 109.0 |
C10—C9—H9B | 109.3 | C28—C29—H29B | 109.0 |
C8—C9—H9B | 109.3 | C30—C29—H29B | 109.0 |
H9A—C9—H9B | 107.9 | H29A—C29—H29B | 107.8 |
C9—C10—H10A | 109.5 | C29—C30—H30A | 109.5 |
C9—C10—H10B | 109.5 | C29—C30—H30B | 109.5 |
H10A—C10—H10B | 109.5 | H30A—C30—H30B | 109.5 |
C9—C10—H10C | 109.5 | C29—C30—H30C | 109.5 |
H10A—C10—H10C | 109.5 | H30A—C30—H30C | 109.5 |
H10B—C10—H10C | 109.5 | H30B—C30—H30C | 109.5 |
C7—N1—S1 | 126.7 (8) | C27—N21—S2 | 125.4 (6) |
C7—N1—H1N | 116.7 | C27—N21—H21N | 117.3 |
S1—N1—H1N | 116.7 | S2—N21—H21N | 117.3 |
C7—N2—C8 | 120.2 (9) | C27—N22—C28 | 123.1 (8) |
C7—N2—H2N | 119.9 | C27—N22—H22N | 118.4 |
C8—N2—H2N | 119.9 | C28—N22—H22N | 118.4 |
O1—S1—O2 | 119.8 (3) | O21—S2—O22 | 120.1 (4) |
O1—S1—N1 | 105.4 (7) | O21—S2—N21 | 104.3 (5) |
O2—S1—N1 | 111.9 (8) | O22—S2—N21 | 110.0 (9) |
O1—S1—C4 | 107.6 (8) | O21—S2—C24 | 108.2 (8) |
O2—S1—C4 | 107.2 (6) | O22—S2—C24 | 108.2 (6) |
N1—S1—C4 | 103.7 (6) | N21—S2—C24 | 105.0 (5) |
| | | |
C6—C1—C2—C3 | 0.0 | C26—C21—C22—C23 | 0.0 |
Cl1—C1—C2—C3 | −176.2 (6) | Cl2—C21—C22—C23 | −179.6 (5) |
C1—C2—C3—C4 | 0.0 | C21—C22—C23—C24 | 0.0 |
C2—C3—C4—C5 | 0.0 | C22—C23—C24—C25 | 0.0 |
C2—C3—C4—S1 | 175.3 (5) | C22—C23—C24—S2 | 178.4 (5) |
C3—C4—C5—C6 | 0.0 | C23—C24—C25—C26 | 0.0 |
S1—C4—C5—C6 | −175.3 (5) | S2—C24—C25—C26 | −178.5 (5) |
C4—C5—C6—C1 | 0.0 | C24—C25—C26—C21 | 0.0 |
C2—C1—C6—C5 | 0.0 | C22—C21—C26—C25 | 0.0 |
Cl1—C1—C6—C5 | 176.2 (6) | Cl2—C21—C26—C25 | 179.6 (5) |
N2—C8—C9—C10 | −159.7 (12) | N22—C28—C29—C30 | −178.9 (7) |
O3—C7—N1—S1 | −14 (3) | O23—C27—N21—S2 | −9 (3) |
N2—C7—N1—S1 | 168.1 (14) | N22—C27—N21—S2 | 170.4 (14) |
O3—C7—N2—C8 | −1 (3) | O23—C27—N22—C28 | 0 (3) |
N1—C7—N2—C8 | 177.4 (16) | N21—C27—N22—C28 | −179.2 (16) |
C9—C8—N2—C7 | −75 (2) | C29—C28—N22—C27 | −88.3 (19) |
C7—N1—S1—O1 | 164.2 (13) | C27—N21—S2—O21 | 166.0 (14) |
C7—N1—S1—O2 | 32.4 (16) | C27—N21—S2—O22 | 35.9 (16) |
C7—N1—S1—C4 | −82.9 (14) | C27—N21—S2—C24 | −80.3 (15) |
C5—C4—S1—O1 | −158.0 (5) | C23—C24—S2—O21 | 23.3 (5) |
C3—C4—S1—O1 | 26.7 (6) | C25—C24—S2—O21 | −158.2 (4) |
C5—C4—S1—O2 | −27.9 (7) | C23—C24—S2—O22 | 154.9 (6) |
C3—C4—S1—O2 | 156.8 (6) | C25—C24—S2—O22 | −26.6 (7) |
C5—C4—S1—N1 | 90.7 (5) | C23—C24—S2—N21 | −87.6 (5) |
C3—C4—S1—N1 | −84.6 (5) | C25—C24—S2—N21 | 90.9 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21N···O3 | 0.86 | 1.88 | 2.665 (12) | 151 |
N22—H22N···O2 | 0.86 | 2.31 | 2.915 (14) | 128 |
N22—H22N···O3 | 0.86 | 2.13 | 2.842 (9) | 140 |
N1—H1N···O23i | 0.86 | 1.92 | 2.708 (11) | 152 |
N2—H2N···O22i | 0.86 | 2.26 | 2.922 (10) | 134 |
N2—H2N···O23i | 0.86 | 2.06 | 2.817 (11) | 146 |
Symmetry code: (i) x, y, z−1. |
(acpa_3.33GPa) 4-chloro-
N-((propylaminocarbonyl)benzenesulfonamide
top
Crystal data top
C10H13ClN2O3S | F(000) = 576 |
Mr = 276.73 | Dx = 1.797 Mg m−3 |
Monoclinic, P2111 | Melting point: phase transition K |
Hall symbol: P 2xa | Mo Kα radiation, λ = 0.71073 Å |
a = 25.522 (6) Å | Cell parameters from 3305 reflections |
b = 4.6023 (7) Å | θ = 2.3–30.8° |
c = 8.8298 (15) Å | µ = 0.58 mm−1 |
β = 90° | T = 293 K |
V = 1023.0 (3) Å3 | Plate, colorless |
Z = 4 | 0.22 × 0.11 × 0.04 mm |
Data collection top
Oxford Diffraction KM4 CCD diffractometer | 1786 independent reflections |
Radiation source: fine-focus sealed tube | 1068 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.114 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 30.7°, θmin = 2.3° |
ω scans | h = −8→8 |
Absorption correction: numerical Absorb6.1 (R. J. Angel, 2006) | k = −6→6 |
Tmin = 0.331, Tmax = 0.468 | l = −12→12 |
10207 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0734P)2] where P = (Fo2 + 2Fc2)/3 |
1786 reflections | (Δ/σ)max < 0.001 |
115 parameters | Δρmax = 0.26 e Å−3 |
3 restraints | Δρmin = −0.27 e Å−3 |
Crystal data top
C10H13ClN2O3S | V = 1023.0 (3) Å3 |
Mr = 276.73 | Z = 4 |
Monoclinic, P2111 | Mo Kα radiation |
a = 25.522 (6) Å | µ = 0.58 mm−1 |
b = 4.6023 (7) Å | T = 293 K |
c = 8.8298 (15) Å | 0.22 × 0.11 × 0.04 mm |
β = 90° | |
Data collection top
Oxford Diffraction KM4 CCD diffractometer | 1786 independent reflections |
Absorption correction: numerical Absorb6.1 (R. J. Angel, 2006) | 1068 reflections with I > 2σ(I) |
Tmin = 0.331, Tmax = 0.468 | Rint = 0.114 |
10207 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.060 | 3 restraints |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.26 e Å−3 |
1786 reflections | Δρmin = −0.27 e Å−3 |
115 parameters | |
Special details top
Experimental. high pressure measurement at 3.33 GPa in the DAC |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.8877 (5) | 1.0545 (11) | 0.4534 (6) | 0.024 (2)* | |
C2 | 0.8764 (5) | 0.8855 (12) | 0.3118 (5) | 0.020 (2)* | |
H2 | 0.8958 | 0.9101 | 0.2256 | 0.025* | |
C3 | 0.8361 (5) | 0.6798 (11) | 0.2988 (5) | 0.024 (2)* | |
H3 | 0.8286 | 0.5667 | 0.2041 | 0.029* | |
C4 | 0.8071 (5) | 0.6430 (11) | 0.4276 (6) | 0.015 (2)* | |
C5 | 0.8184 (5) | 0.8120 (12) | 0.5692 (5) | 0.025 (2)* | |
H5 | 0.7990 | 0.7875 | 0.6553 | 0.030* | |
C6 | 0.8587 (5) | 1.0178 (11) | 0.5821 (4) | 0.015 (2)* | |
H6 | 0.8663 | 1.1308 | 0.6769 | 0.018* | |
C7 | 0.6755 (11) | 0.8000 (17) | 0.4599 (8) | 0.021 (2)* | |
C8 | 0.6098 (11) | 1.1752 (17) | 0.4775 (9) | 0.023 (2)* | |
H8A | 0.5976 | 1.3131 | 0.4132 | 0.028* | |
H8B | 0.6273 | 1.2869 | 0.5658 | 0.028* | |
C9 | 0.5638 (11) | 1.0190 (19) | 0.5308 (9) | 0.023 (2)* | |
H9A | 0.5733 | 0.9339 | 0.6205 | 0.027* | |
H9B | 0.5526 | 0.8614 | 0.4506 | 0.027* | |
C10 | 0.5194 (11) | 1.2431 (18) | 0.5707 (11) | 0.031 (3)* | |
H10A | 0.5001 | 1.2611 | 0.4793 | 0.046* | |
H10B | 0.5339 | 1.4310 | 0.6137 | 0.046* | |
H10C | 0.4963 | 1.1772 | 0.6439 | 0.046* | |
Cl1 | 0.9329 (3) | 1.3284 (5) | 0.4696 (2) | 0.0338 (7)* | |
N1 | 0.7061 (8) | 0.5946 (13) | 0.3608 (7) | 0.0203 (18)* | |
H1N | 0.6980 | 0.5694 | 0.2649 | 0.024* | |
N2 | 0.6470 (8) | 0.9726 (13) | 0.3914 (7) | 0.0181 (17)* | |
H2N | 0.6501 | 0.9670 | 0.2940 | 0.022* | |
O1 | 0.7639 (7) | 0.1832 (10) | 0.2786 (5) | 0.0219 (15)* | |
O2 | 0.7432 (7) | 0.3227 (11) | 0.5549 (5) | 0.0225 (14)* | |
O3 | 0.6740 (7) | 0.8051 (10) | 0.6010 (5) | 0.0172 (14)* | |
S1 | 0.7546 (3) | 0.4013 (4) | 0.4083 (2) | 0.0196 (6)* | |
C21 | 0.4618 (4) | 0.5285 (11) | 1.0707 (6) | 0.019 (2)* | |
C22 | 0.4630 (4) | 0.6398 (11) | 0.9336 (5) | 0.027 (2)* | |
H22 | 0.4366 | 0.5913 | 0.8614 | 0.033* | |
C23 | 0.5037 (5) | 0.8235 (11) | 0.9045 (5) | 0.023 (2)* | |
H23 | 0.5045 | 0.8979 | 0.8128 | 0.027* | |
C24 | 0.5432 (4) | 0.8959 (11) | 1.0125 (6) | 0.017 (2)* | |
C25 | 0.5420 (4) | 0.7846 (12) | 1.1496 (6) | 0.025 (2)* | |
H25 | 0.5685 | 0.8331 | 1.2218 | 0.030* | |
C26 | 0.5013 (4) | 0.6009 (12) | 1.1787 (5) | 0.026 (2)* | |
H26 | 0.5005 | 0.5265 | 1.2704 | 0.032* | |
C27 | 0.6722 (10) | 0.7097 (15) | 0.9523 (8) | 0.015 (2)* | |
C28 | 0.7335 (8) | 0.3035 (19) | 0.8991 (9) | 0.023 (2)* | |
H28A | 0.7329 | 0.1278 | 0.8215 | 0.028* | |
H28B | 0.7217 | 0.2479 | 0.9948 | 0.028* | |
C29 | 0.7887 (8) | 0.4107 (18) | 0.9191 (9) | 0.018 (2)* | |
H29A | 0.7899 | 0.5844 | 0.9979 | 0.022* | |
H29B | 0.8010 | 0.4661 | 0.8239 | 0.022* | |
C30 | 0.8248 (9) | 0.1752 (17) | 0.9643 (10) | 0.030 (2)* | |
H30A | 0.8224 | −0.0004 | 0.8891 | 0.045* | |
H30B | 0.8145 | 0.1321 | 1.0628 | 0.045* | |
H30C | 0.8603 | 0.2457 | 0.9696 | 0.045* | |
Cl2 | 0.4144 (3) | 0.2969 (5) | 1.1103 (3) | 0.0388 (7)* | |
N21 | 0.6381 (8) | 0.8872 (13) | 0.8846 (7) | 0.0209 (18)* | |
H21N | 0.6393 | 0.8759 | 0.7864 | 0.025* | |
N22 | 0.6961 (8) | 0.5186 (13) | 0.8542 (7) | 0.0219 (19)* | |
H22N | 0.6900 | 0.5157 | 0.7581 | 0.026* | |
O21 | 0.5805 (6) | 1.2909 (11) | 0.8702 (5) | 0.0211 (14)* | |
O22 | 0.6175 (6) | 1.2417 (11) | 1.1239 (6) | 0.0212 (14)* | |
O23 | 0.6791 (8) | 0.7323 (11) | 1.0882 (6) | 0.0274 (16)* | |
S2 | 0.5964 (3) | 1.1128 (4) | 0.9782 (2) | 0.0182 (5)* | |
Geometric parameters (Å, º) top
C1—C2 | 1.3900 | C21—C22 | 1.3900 |
C1—C6 | 1.3900 | C21—C26 | 1.3900 |
C1—Cl1 | 1.697 (10) | C21—Cl2 | 1.688 (10) |
C2—C3 | 1.3900 | C22—C23 | 1.3900 |
C2—H2 | 0.9300 | C22—H22 | 0.9300 |
C3—C4 | 1.3900 | C23—C24 | 1.3900 |
C3—H3 | 0.9300 | C23—H23 | 0.9300 |
C4—C5 | 1.3900 | C24—C25 | 1.3900 |
C4—S1 | 1.732 (10) | C24—S2 | 1.741 (10) |
C5—C6 | 1.3900 | C25—C26 | 1.3900 |
C5—H5 | 0.9300 | C25—H25 | 0.9300 |
C6—H6 | 0.9300 | C26—H26 | 0.9300 |
C7—O3 | 1.243 (9) | C27—O23 | 1.200 (9) |
C7—N2 | 1.299 (19) | C27—N22 | 1.282 (17) |
C7—N1 | 1.41 (2) | C27—N21 | 1.39 (2) |
C8—N2 | 1.45 (2) | C28—N22 | 1.48 (2) |
C8—C9 | 1.49 (3) | C28—C29 | 1.494 (18) |
C8—H8A | 0.9700 | C28—H28A | 0.9700 |
C8—H8B | 0.9700 | C28—H28B | 0.9700 |
C9—C10 | 1.53 (3) | C29—C30 | 1.525 (16) |
C9—H9A | 0.9700 | C29—H29A | 0.9700 |
C9—H9B | 0.9700 | C29—H29B | 0.9700 |
C10—H10A | 0.9600 | C30—H30A | 0.9600 |
C10—H10B | 0.9600 | C30—H30B | 0.9600 |
C10—H10C | 0.9600 | C30—H30C | 0.9600 |
N1—S1 | 1.620 (17) | N21—S2 | 1.615 (14) |
N1—H1N | 0.8600 | N21—H21N | 0.8600 |
N2—H2N | 0.8600 | N22—H22N | 0.8600 |
O1—S1 | 1.413 (6) | O21—S2 | 1.416 (7) |
O2—S1 | 1.430 (6) | O22—S2 | 1.430 (8) |
| | | |
C2—C1—C6 | 120.0 | C22—C21—C26 | 120.0 |
C2—C1—Cl1 | 121.0 (3) | C22—C21—Cl2 | 122.2 (4) |
C6—C1—Cl1 | 118.8 (3) | C26—C21—Cl2 | 117.8 (4) |
C3—C2—C1 | 120.0 | C21—C22—C23 | 120.0 |
C3—C2—H2 | 120.0 | C21—C22—H22 | 120.0 |
C1—C2—H2 | 120.0 | C23—C22—H22 | 120.0 |
C2—C3—C4 | 120.0 | C22—C23—C24 | 120.0 |
C2—C3—H3 | 120.0 | C22—C23—H23 | 120.0 |
C4—C3—H3 | 120.0 | C24—C23—H23 | 120.0 |
C5—C4—C3 | 120.0 | C25—C24—C23 | 120.0 |
C5—C4—S1 | 120.3 (3) | C25—C24—S2 | 118.2 (4) |
C3—C4—S1 | 119.6 (3) | C23—C24—S2 | 121.7 (3) |
C4—C5—C6 | 120.0 | C24—C25—C26 | 120.0 |
C4—C5—H5 | 120.0 | C24—C25—H25 | 120.0 |
C6—C5—H5 | 120.0 | C26—C25—H25 | 120.0 |
C5—C6—C1 | 120.0 | C25—C26—C21 | 120.0 |
C5—C6—H6 | 120.0 | C25—C26—H26 | 120.0 |
C1—C6—H6 | 120.0 | C21—C26—H26 | 120.0 |
O3—C7—N2 | 122.4 (16) | O23—C27—N22 | 122.9 (16) |
O3—C7—N1 | 122.7 (14) | O23—C27—N21 | 124.0 (13) |
N2—C7—N1 | 114.8 (7) | N22—C27—N21 | 113.1 (8) |
N2—C8—C9 | 112.2 (9) | N22—C28—C29 | 114.8 (10) |
N2—C8—H8A | 109.2 | N22—C28—H28A | 108.6 |
C9—C8—H8A | 109.2 | C29—C28—H28A | 108.6 |
N2—C8—H8B | 109.2 | N22—C28—H28B | 108.6 |
C9—C8—H8B | 109.2 | C29—C28—H28B | 108.6 |
H8A—C8—H8B | 107.9 | H28A—C28—H28B | 107.5 |
C8—C9—C10 | 108.2 (10) | C28—C29—C30 | 111.5 (11) |
C8—C9—H9A | 110.0 | C28—C29—H29A | 109.3 |
C10—C9—H9A | 110.0 | C30—C29—H29A | 109.3 |
C8—C9—H9B | 110.0 | C28—C29—H29B | 109.3 |
C10—C9—H9B | 110.0 | C30—C29—H29B | 109.3 |
H9A—C9—H9B | 108.4 | H29A—C29—H29B | 108.0 |
C9—C10—H10A | 109.5 | C29—C30—H30A | 109.5 |
C9—C10—H10B | 109.5 | C29—C30—H30B | 109.5 |
H10A—C10—H10B | 109.5 | H30A—C30—H30B | 109.5 |
C9—C10—H10C | 109.5 | C29—C30—H30C | 109.5 |
H10A—C10—H10C | 109.5 | H30A—C30—H30C | 109.5 |
H10B—C10—H10C | 109.5 | H30B—C30—H30C | 109.5 |
C7—N1—S1 | 127.0 (8) | C27—N21—S2 | 124.3 (6) |
C7—N1—H1N | 116.5 | C27—N21—H21N | 117.8 |
S1—N1—H1N | 116.5 | S2—N21—H21N | 117.8 |
C7—N2—C8 | 120.8 (9) | C27—N22—C28 | 122.8 (8) |
C7—N2—H2N | 119.6 | C27—N22—H22N | 118.6 |
C8—N2—H2N | 119.6 | C28—N22—H22N | 118.6 |
O1—S1—O2 | 121.1 (3) | O21—S2—O22 | 120.9 (4) |
O1—S1—N1 | 105.4 (6) | O21—S2—N21 | 103.8 (5) |
O2—S1—N1 | 108.1 (8) | O22—S2—N21 | 110.5 (8) |
O1—S1—C4 | 108.0 (7) | O21—S2—C24 | 107.8 (8) |
O2—S1—C4 | 108.8 (6) | O22—S2—C24 | 107.5 (5) |
N1—S1—C4 | 104.2 (5) | N21—S2—C24 | 105.3 (5) |
| | | |
C6—C1—C2—C3 | 0.0 | C26—C21—C22—C23 | 0.0 |
Cl1—C1—C2—C3 | −174.4 (6) | Cl2—C21—C22—C23 | −178.2 (5) |
C1—C2—C3—C4 | 0.0 | C21—C22—C23—C24 | 0.0 |
C2—C3—C4—C5 | 0.0 | C22—C23—C24—C25 | 0.0 |
C2—C3—C4—S1 | 176.3 (5) | C22—C23—C24—S2 | 177.3 (5) |
C3—C4—C5—C6 | 0.0 | C23—C24—C25—C26 | 0.0 |
S1—C4—C5—C6 | −176.3 (5) | S2—C24—C25—C26 | −177.4 (5) |
C4—C5—C6—C1 | 0.0 | C24—C25—C26—C21 | 0.0 |
C2—C1—C6—C5 | 0.0 | C22—C21—C26—C25 | 0.0 |
Cl1—C1—C6—C5 | 174.5 (5) | Cl2—C21—C26—C25 | 178.3 (5) |
N2—C8—C9—C10 | −161.3 (11) | N22—C28—C29—C30 | −179.6 (7) |
O3—C7—N1—S1 | −18 (3) | O23—C27—N21—S2 | −10 (3) |
N2—C7—N1—S1 | 165.4 (14) | N22—C27—N21—S2 | 170.3 (13) |
O3—C7—N2—C8 | −2 (3) | O23—C27—N22—C28 | 1 (3) |
N1—C7—N2—C8 | 174.0 (15) | N21—C27—N22—C28 | −179.0 (16) |
C9—C8—N2—C7 | −71 (2) | C29—C28—N22—C27 | −87.3 (19) |
C7—N1—S1—O1 | 166.5 (13) | C27—N21—S2—O21 | 166.2 (13) |
C7—N1—S1—O2 | 35.7 (15) | C27—N21—S2—O22 | 35.2 (15) |
C7—N1—S1—C4 | −79.9 (14) | C27—N21—S2—C24 | −80.7 (14) |
C5—C4—S1—O1 | −157.0 (5) | C25—C24—S2—O21 | −157.1 (4) |
C3—C4—S1—O1 | 26.6 (6) | C23—C24—S2—O21 | 25.5 (5) |
C5—C4—S1—O2 | −23.9 (7) | C25—C24—S2—O22 | −25.3 (6) |
C3—C4—S1—O2 | 159.7 (6) | C23—C24—S2—O22 | 157.3 (6) |
C5—C4—S1—N1 | 91.2 (4) | C25—C24—S2—N21 | 92.6 (5) |
C3—C4—S1—N1 | −85.1 (5) | C23—C24—S2—N21 | −84.8 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21N···O3 | 0.86 | 1.84 | 2.634 (11) | 152 |
N22—H22N···O2 | 0.86 | 2.31 | 2.908 (13) | 127 |
N22—H22N···O3 | 0.86 | 2.12 | 2.833 (9) | 141 |
N1—H1N···O23i | 0.86 | 1.90 | 2.678 (10) | 149 |
N2—H2N···O22i | 0.86 | 2.27 | 2.939 (10) | 134 |
N2—H2N···O23i | 0.86 | 2.09 | 2.844 (11) | 146 |
Symmetry code: (i) x, y, z−1. |
Experimental details
| (1.18GPa) | (acpa_2.10GPa) | (acpa_2.50GPa) | (acpa_2.63GPa) |
Crystal data |
Chemical formula | C10H13ClN2O3S | C10H13ClN2O3S | C10H13ClN2O3S | C10H13ClN2O3S |
Mr | 276.73 | 276.73 | 276.73 | 276.73 |
Crystal system, space group | Orthorhombic, P212121 | Orthorhombic, P212121 | Orthorhombic, P212121 | Orthorhombic, P212121 |
Temperature (K) | 293 | 293 | 293 | 293 |
a, b, c (Å) | 26.573 (2), 4.8587 (2), 8.8165 (4) | 26.5733 (18), 4.7178 (2), 8.6406 (2) | 26.605 (2), 4.6688 (2), 8.5711 (3) | 26.6068 (19), 4.6576 (2), 8.5556 (2) |
α, β, γ (°) | 90, 90, 90 | 90, 90, 90 | 90, 90, 90 | 90, 90, 90 |
V (Å3) | 1138.30 (11) | 1083.25 (9) | 1064.65 (10) | 1060.24 (9) |
Z | 4 | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.52 | 0.54 | 0.55 | 0.56 |
Crystal size (mm) | 0.22 × 0.11 × 0.04 | 0.22 × 0.11 × 0.04 | 0.22 × 0.11 × 0.04 | 0.22 × 0.11 × 0.04 |
|
Data collection |
Diffractometer | Oxford Diffraction KM4 CCD diffractometer | Oxford Diffraction KM4 CCD diffractometer | Oxford Diffraction KM4 CCD diffractometer | Oxford Diffraction KM4 CCD diffractometer |
Absorption correction | Numerical Absorb6.1 (Angel, 2006) | Numerical Absorb6.1 (R. J. Angel, 2006) | Numerical Absorb6.1 (R. J. Angel, 2006) | Numerical Absorb6.1 (R. J. Angel, 2006) |
Tmin, Tmax | 0.331, 0.468 | 0.328, 0.468 | 0.323, 0.468 | 0.323, 0.468 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9661, 896, 608 | 10853, 1040, 657 | 10571, 1030, 647 | 10572, 1025, 656 |
Rint | 0.095 | 0.097 | 0.096 | 0.095 |
(sin θ/λ)max (Å−1) | 0.625 | 0.723 | 0.726 | 0.726 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.117, 1.08 | 0.045, 0.103, 0.97 | 0.050, 0.125, 0.99 | 0.046, 0.104, 0.99 |
No. of reflections | 896 | 1040 | 1030 | 1025 |
No. of parameters | 73 | 63 | 58 | 63 |
No. of restraints | 0 | 0 | 0 | 0 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.17 | 0.18, −0.18 | 0.22, −0.28 | 0.21, −0.26 |
| (acpa_2.91GPa) | (acpa_3.33GPa) |
Crystal data |
Chemical formula | C10H13ClN2O3S | C10H13ClN2O3S |
Mr | 276.73 | 276.73 |
Crystal system, space group | Monoclinic, P2111 | Monoclinic, P2111 |
Temperature (K) | 293 | 293 |
a, b, c (Å) | 25.602 (3), 4.6340 (2), 8.8525 (4) | 25.522 (6), 4.6023 (7), 8.8298 (15) |
α, β, γ (°) | 99.109 (4), 90, 90 | 99.477 (14), 90, 90 |
V (Å3) | 1037.01 (14) | 1023.0 (3) |
Z | 4 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.57 | 0.58 |
Crystal size (mm) | 0.22 × 0.11 × 0.04 | 0.22 × 0.11 × 0.04 |
|
Data collection |
Diffractometer | Oxford Diffraction KM4 CCD diffractometer | Oxford Diffraction KM4 CCD diffractometer |
Absorption correction | Numerical Absorb6.1 (R. J. Angel, 2006) | Numerical Absorb6.1 (R. J. Angel, 2006) |
Tmin, Tmax | 0.331, 0.468 | 0.331, 0.468 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10171, 1745, 1083 | 10207, 1786, 1068 |
Rint | 0.113 | 0.114 |
(sin θ/λ)max (Å−1) | 0.730 | 0.718 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.068, 0.144, 1.00 | 0.060, 0.142, 1.00 |
No. of reflections | 1745 | 1786 |
No. of parameters | 115 | 115 |
No. of restraints | 3 | 3 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.28, −0.30 | 0.26, −0.27 |
Hydrogen-bond geometry (Å, º) for (1.18GPa) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H10···O3i | 0.86 | 1.89 | 2.704 (10) | 156.6 |
N2—H20···O2i | 0.86 | 2.17 | 2.850 (9) | 135.3 |
N2—H20···O3i | 0.86 | 2.20 | 2.927 (6) | 142.8 |
Symmetry code: (i) −x+1/2, −y+1, z+1/2. |
Hydrogen-bond geometry (Å, º) for (acpa_2.10GPa) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.86 | 1.84 | 2.648 (8) | 155.0 |
N2—H2A···O2i | 0.86 | 2.14 | 2.797 (7) | 133.2 |
N2—H2A···O3i | 0.86 | 2.16 | 2.875 (5) | 139.7 |
Symmetry code: (i) −x+1/2, −y+1, z+1/2. |
Hydrogen-bond geometry (Å, º) for (acpa_2.50GPa) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.86 | 1.86 | 2.664 (11) | 154.1 |
N2—H2A···O2i | 0.86 | 2.11 | 2.772 (9) | 133.1 |
N2—H2A···O3i | 0.86 | 2.17 | 2.869 (5) | 138.1 |
Symmetry code: (i) −x+1/2, −y+1, z+1/2. |
Hydrogen-bond geometry (Å, º) for (acpa_2.63GPa) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.86 | 1.87 | 2.657 (9) | 152.1 |
N2—H2A···O2i | 0.86 | 2.13 | 2.782 (8) | 132.0 |
N2—H2A···O3i | 0.86 | 2.17 | 2.864 (5) | 137.4 |
Symmetry code: (i) −x+1/2, −y+1, z+1/2. |
Hydrogen-bond geometry (Å, º) for (acpa_2.91GPa) top
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21N···O3 | 0.86 | 1.88 | 2.665 (12) | 151.4 |
N22—H22N···O2 | 0.86 | 2.31 | 2.915 (14) | 127.7 |
N22—H22N···O3 | 0.86 | 2.13 | 2.842 (9) | 139.8 |
N1—H1N···O23i | 0.86 | 1.92 | 2.708 (11) | 152.2 |
N2—H2N···O22i | 0.86 | 2.26 | 2.922 (10) | 134.3 |
N2—H2N···O23i | 0.86 | 2.06 | 2.817 (11) | 146.3 |
Symmetry code: (i) x, y, z−1. |
Hydrogen-bond geometry (Å, º) for (acpa_3.33GPa) top
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21N···O3 | 0.86 | 1.84 | 2.634 (11) | 152.3 |
N22—H22N···O2 | 0.86 | 2.31 | 2.908 (13) | 127.0 |
N22—H22N···O3 | 0.86 | 2.12 | 2.833 (9) | 140.5 |
N1—H1N···O23i | 0.86 | 1.90 | 2.678 (10) | 149.4 |
N2—H2N···O22i | 0.86 | 2.27 | 2.939 (10) | 134.3 |
N2—H2N···O23i | 0.86 | 2.09 | 2.844 (11) | 145.9 |
Symmetry code: (i) x, y, z−1. |
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