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Two new 1,2,4-triazine-containing sulfonamide derivatives, namely, 4-bromo-N-(5,6-diphenyl-2H-1,2,4-triazin-3-yl­idene)benzene­sulfonamide, C21H15BrN4O4S, 3a, and methyl 2-{[(5,6-diphenyl-1,2,4-triazin-3-yl)sulfamo­yl]meth­yl}benzoate, C24H20N4O4S, 3b, which crystallize in the different sulfonimide and sulfonamide tautomeric forms, respectively, were synthesized and characterized by spectroscopic, X-ray diffraction and theoretical calculation methods. Both mol­ecules adopt a very similar conformation of the common part of the structure and the differences occur within the substituents on the sulfonamide group. The amino groups characteristic for the existing tautomeric forms are involved in strong inter­molecular N—H...N and N—H...O hydrogen bonds in 3a and 3b, respectively. The Hirshfeld surface analysis showed that H...H contacts constitute a high percentage of the inter­molecular inter­actions. Theoretical calculations at the ab initio DFT/B3LYP/6-311++G(d,p) level showed that the two tautomeric forms observed for 3a and 3b can co-exist in chloro­form, ethanol and water solutions, with a distinct predominance of the sulfonamide form; the participation of the sulfonimide form increases with increasing solvent polarity.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229622007781/ef3031sup1.cif
Contains datablocks 3a, 3b, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229622007781/ef30313asup2.hkl
Contains datablock 3a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229622007781/ef30313bsup3.hkl
Contains datablock 3b

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229622007781/ef30313asup4.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229622007781/ef30313bsup5.cml
Supplementary material

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229622007781/ef3031sup6.pdf
NMR spectra

CCDC references: 2194382; 2194383

Computing details top

For both structures, data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and WinGX (Farrugia, 2012).

4-Bromo-N-(5,6-diphenyl-2H-1,2,4-triazin-3-ylidene)benzenesulfonamide (3a) top
Crystal data top
C21H15BrN4O2SZ = 2
Mr = 467.34F(000) = 472
Triclinic, P1Dx = 1.589 Mg m3
a = 5.781 (2) ÅCu Kα radiation, λ = 1.54184 Å
b = 12.717 (2) ÅCell parameters from 1543 reflections
c = 14.655 (3) Åθ = 3.8–74.9°
α = 67.751 (18)°µ = 4.09 mm1
β = 78.78 (3)°T = 120 K
γ = 82.94 (2)°Needle, yellow
V = 976.7 (5) Å30.25 × 0.10 × 0.05 mm
Data collection top
Agilent SuperNova Single Source
diffractometer with an Atlas detector
3828 independent reflections
Radiation source: sealed X-ray tube, SuperNova (Cu) X-ray Source2377 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.061
Detector resolution: 5.2763 pixels mm-1θmax = 80.3°, θmin = 3.3°
ω scansh = 75
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
k = 1515
Tmin = 0.589, Tmax = 1.000l = 1817
6490 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.079Hydrogen site location: difference Fourier map
wR(F2) = 0.251H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0949P)2 + 2.6148P]
where P = (Fo2 + 2Fc2)/3
3828 reflections(Δ/σ)max < 0.001
275 parametersΔρmax = 0.56 e Å3
0 restraintsΔρmin = 0.65 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C30.8158 (12)0.4867 (4)0.8997 (4)0.0338 (13)
C51.0892 (11)0.3917 (5)0.8175 (4)0.0341 (13)
C60.9554 (11)0.2917 (5)0.8682 (4)0.0334 (13)
C511.3032 (12)0.3995 (5)0.7422 (5)0.0379 (13)
C521.4683 (12)0.4794 (5)0.7265 (5)0.0411 (14)
H521.44120.52600.76380.062*
C531.6713 (14)0.4895 (6)0.6561 (6)0.0546 (18)
H531.78420.53950.64870.082*
C541.7041 (14)0.4237 (7)0.5964 (6)0.061 (2)
H541.83880.43040.54850.091*
C551.5355 (14)0.3483 (6)0.6086 (6)0.0522 (18)
H551.55620.30610.56750.078*
C561.3386 (12)0.3355 (5)0.6809 (5)0.0414 (14)
H561.22830.28400.68900.062*
C611.0298 (11)0.1768 (4)0.8656 (4)0.0326 (12)
C621.2389 (12)0.1228 (5)0.8983 (4)0.0364 (13)
H621.33560.15950.91920.055*
C631.3023 (12)0.0127 (5)0.8993 (4)0.0365 (13)
H631.44130.02420.92140.055*
C641.1595 (12)0.0408 (5)0.8678 (5)0.0423 (15)
H641.20150.11450.86980.063*
C650.9543 (11)0.0134 (5)0.8332 (5)0.0368 (13)
H650.86030.02280.81040.055*
C660.8903 (12)0.1218 (5)0.8328 (5)0.0372 (13)
H660.75150.15830.81010.056*
C810.8559 (12)0.7498 (5)0.7498 (4)0.0374 (13)
C820.6485 (15)0.8025 (9)0.7173 (6)0.072 (3)
H820.51570.80870.76270.108*
C830.6411 (19)0.8462 (11)0.6155 (8)0.092 (4)
H830.50090.88000.59270.138*
C840.8372 (18)0.8401 (7)0.5487 (5)0.059 (2)
C851.0393 (18)0.7889 (6)0.5817 (6)0.067 (3)
H851.17360.78480.53620.100*
C861.0478 (15)0.7428 (6)0.6822 (6)0.062 (2)
H861.18720.70620.70430.093*
N10.7504 (10)0.2960 (4)0.9250 (3)0.0356 (12)
N20.6833 (10)0.3961 (4)0.9355 (4)0.0365 (12)
H20.587 (15)0.400 (7)0.974 (6)0.055*
N41.0171 (10)0.4866 (4)0.8345 (4)0.0364 (11)
N70.7303 (10)0.5754 (4)0.9250 (4)0.0374 (12)
O11.1136 (9)0.6745 (4)0.8896 (4)0.0514 (12)
O20.7214 (10)0.7651 (4)0.9239 (4)0.0515 (13)
S80.8673 (3)0.69186 (12)0.87965 (11)0.0406 (4)
Br1A0.879 (3)0.8881 (9)0.4094 (4)0.061 (2)0.47 (4)
Br1B0.780 (4)0.9120 (11)0.4108 (5)0.079 (3)0.53 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C30.048 (4)0.017 (2)0.037 (3)0.006 (2)0.012 (3)0.011 (2)
C50.046 (4)0.022 (3)0.035 (3)0.002 (2)0.007 (2)0.011 (2)
C60.048 (4)0.023 (3)0.032 (3)0.001 (2)0.006 (2)0.015 (2)
C510.044 (4)0.028 (3)0.040 (3)0.003 (3)0.008 (3)0.009 (2)
C520.048 (4)0.027 (3)0.046 (3)0.000 (3)0.013 (3)0.008 (2)
C530.049 (4)0.044 (4)0.060 (4)0.008 (3)0.010 (3)0.004 (3)
C540.048 (5)0.052 (4)0.062 (5)0.002 (3)0.012 (4)0.010 (4)
C550.056 (5)0.045 (4)0.052 (4)0.005 (3)0.008 (3)0.020 (3)
C560.047 (4)0.029 (3)0.048 (3)0.004 (3)0.000 (3)0.017 (3)
C610.047 (4)0.019 (2)0.033 (3)0.000 (2)0.002 (2)0.013 (2)
C620.044 (4)0.027 (3)0.039 (3)0.007 (2)0.008 (3)0.016 (2)
C630.048 (4)0.023 (3)0.038 (3)0.004 (2)0.003 (3)0.014 (2)
C640.053 (4)0.028 (3)0.043 (3)0.001 (3)0.008 (3)0.017 (2)
C650.041 (4)0.033 (3)0.040 (3)0.005 (3)0.004 (3)0.017 (2)
C660.042 (4)0.028 (3)0.044 (3)0.003 (2)0.003 (3)0.020 (2)
C810.049 (4)0.031 (3)0.033 (3)0.005 (3)0.000 (3)0.015 (2)
C820.045 (5)0.099 (7)0.048 (4)0.008 (4)0.002 (3)0.009 (4)
C830.063 (7)0.126 (10)0.062 (6)0.010 (6)0.017 (5)0.002 (6)
C840.102 (7)0.045 (4)0.030 (3)0.030 (4)0.005 (4)0.008 (3)
C850.091 (7)0.040 (4)0.051 (4)0.002 (4)0.024 (4)0.017 (3)
C860.062 (5)0.037 (4)0.063 (5)0.007 (3)0.017 (4)0.009 (3)
N10.057 (3)0.020 (2)0.031 (2)0.008 (2)0.006 (2)0.0141 (18)
N20.050 (3)0.025 (2)0.036 (3)0.001 (2)0.001 (2)0.017 (2)
N40.049 (3)0.022 (2)0.040 (3)0.002 (2)0.006 (2)0.0140 (19)
N70.053 (3)0.022 (2)0.042 (3)0.002 (2)0.002 (2)0.018 (2)
O10.061 (3)0.035 (2)0.070 (3)0.001 (2)0.032 (3)0.023 (2)
O20.082 (4)0.027 (2)0.048 (3)0.008 (2)0.011 (2)0.0251 (19)
S80.0618 (11)0.0247 (7)0.0400 (8)0.0034 (6)0.0078 (7)0.0169 (6)
Br1A0.095 (5)0.049 (2)0.0379 (11)0.004 (2)0.0069 (15)0.0163 (11)
Br1B0.127 (7)0.062 (2)0.0464 (11)0.009 (4)0.022 (2)0.0139 (13)
Geometric parameters (Å, º) top
C3—N71.328 (7)C63—H630.9300
C3—N21.340 (8)C64—C651.381 (10)
C3—N41.354 (8)C64—H640.9300
C5—N41.326 (7)C65—C661.381 (8)
C5—C61.439 (8)C65—H650.9300
C5—C511.474 (9)C66—H660.9300
C6—N11.317 (8)C81—C861.354 (9)
C6—C611.485 (7)C81—C821.377 (11)
C51—C561.397 (8)C81—S81.772 (6)
C51—C521.404 (9)C82—C831.388 (13)
C52—C531.388 (10)C82—H820.9300
C52—H520.9300C83—C841.361 (14)
C53—C541.396 (12)C83—H830.9300
C53—H530.9300C84—C851.348 (13)
C54—C551.391 (11)C84—Br1A1.870 (9)
C54—H540.9300C84—Br1B1.954 (9)
C55—C561.374 (9)C85—C861.372 (12)
C55—H550.9300C85—H850.9300
C56—H560.9300C86—H860.9300
C61—C661.384 (9)N1—N21.341 (6)
C61—C621.391 (9)N2—H20.72 (8)
C62—C631.397 (7)N7—S81.612 (5)
C62—H620.9300O1—S81.441 (5)
C63—C641.372 (9)O2—S81.432 (4)
N7—C3—N2117.0 (6)C66—C65—C64119.2 (6)
N7—C3—N4123.9 (5)C66—C65—H65120.4
N2—C3—N4118.9 (5)C64—C65—H65120.4
N4—C5—C6120.0 (6)C65—C66—C61120.9 (6)
N4—C5—C51115.4 (5)C65—C66—H66119.5
C6—C5—C51124.5 (5)C61—C66—H66119.5
N1—C6—C5120.6 (5)C86—C81—C82119.5 (7)
N1—C6—C61113.8 (5)C86—C81—S8121.0 (6)
C5—C6—C61125.6 (5)C82—C81—S8119.4 (5)
C56—C51—C52118.8 (6)C81—C82—C83118.9 (8)
C56—C51—C5121.9 (6)C81—C82—H82120.6
C52—C51—C5119.1 (6)C83—C82—H82120.6
C53—C52—C51120.8 (6)C84—C83—C82120.6 (10)
C53—C52—H52119.6C84—C83—H83119.7
C51—C52—H52119.6C82—C83—H83119.7
C52—C53—C54119.3 (7)C85—C84—C83119.7 (8)
C52—C53—H53120.4C85—C84—Br1A110.0 (9)
C54—C53—H53120.4C83—C84—Br1A130.2 (10)
C55—C54—C53120.0 (7)C85—C84—Br1B128.1 (10)
C55—C54—H54120.0C83—C84—Br1B112.1 (11)
C53—C54—H54120.0C84—C85—C86120.3 (7)
C56—C55—C54120.5 (7)C84—C85—H85119.9
C56—C55—H55119.7C86—C85—H85119.9
C54—C55—H55119.7C81—C86—C85120.9 (8)
C55—C56—C51120.4 (6)C81—C86—H86119.6
C55—C56—H56119.8C85—C86—H86119.6
C51—C56—H56119.8C6—N1—N2116.0 (5)
C66—C61—C62119.6 (5)C3—N2—N1125.0 (6)
C66—C61—C6120.5 (6)C3—N2—H2112 (7)
C62—C61—C6119.8 (5)N1—N2—H2120 (7)
C61—C62—C63119.3 (6)C5—N4—C3118.4 (5)
C61—C62—H62120.3C3—N7—S8120.8 (5)
C63—C62—H62120.3O2—S8—O1118.1 (3)
C64—C63—C62120.0 (6)O2—S8—N7103.9 (3)
C64—C63—H63120.0O1—S8—N7113.2 (3)
C62—C63—H63120.0O2—S8—C81107.5 (3)
C63—C64—C65120.9 (6)O1—S8—C81106.7 (3)
C63—C64—H64119.5N7—S8—C81106.8 (3)
C65—C64—H64119.5
N4—C5—C6—N16.0 (9)C81—C82—C83—C841.9 (18)
C51—C5—C6—N1171.4 (6)C82—C83—C84—C851.4 (17)
N4—C5—C6—C61172.3 (6)C82—C83—C84—Br1A178.6 (9)
C51—C5—C6—C6110.3 (10)C82—C83—C84—Br1B178.2 (10)
N4—C5—C51—C56148.0 (6)C83—C84—C85—C860.2 (14)
C6—C5—C51—C5629.5 (10)Br1A—C84—C85—C86177.5 (7)
N4—C5—C51—C5227.3 (9)Br1B—C84—C85—C86179.8 (7)
C6—C5—C51—C52155.2 (6)C82—C81—C86—C851.0 (12)
C56—C51—C52—C534.3 (10)S8—C81—C86—C85179.2 (6)
C5—C51—C52—C53179.8 (6)C84—C85—C86—C811.4 (13)
C51—C52—C53—C543.6 (11)C5—C6—N1—N23.0 (8)
C52—C53—C54—C550.6 (12)C61—C6—N1—N2175.5 (5)
C53—C54—C55—C561.7 (13)N7—C3—N2—N1173.8 (6)
C54—C55—C56—C511.0 (12)N4—C3—N2—N111.3 (9)
C52—C51—C56—C552.0 (10)C6—N1—N2—C35.6 (9)
C5—C51—C56—C55177.3 (7)C6—C5—N4—C30.4 (9)
N1—C6—C61—C6659.1 (8)C51—C5—N4—C3177.2 (5)
C5—C6—C61—C66122.5 (7)N7—C3—N4—C5177.9 (6)
N1—C6—C61—C62119.5 (6)N2—C3—N4—C57.6 (9)
C5—C6—C61—C6258.9 (8)N2—C3—N7—S8175.7 (5)
C66—C61—C62—C631.3 (9)N4—C3—N7—S81.0 (9)
C6—C61—C62—C63177.4 (5)C3—N7—S8—O2179.8 (5)
C61—C62—C63—C640.4 (9)C3—N7—S8—O150.7 (6)
C62—C63—C64—C651.1 (9)C3—N7—S8—C8166.4 (6)
C63—C64—C65—C661.6 (9)C86—C81—S8—O2144.6 (6)
C64—C65—C66—C610.6 (9)C82—C81—S8—O235.5 (7)
C62—C61—C66—C650.8 (9)C86—C81—S8—O117.0 (6)
C6—C61—C66—C65177.8 (6)C82—C81—S8—O1163.1 (7)
C86—C81—C82—C830.6 (15)C86—C81—S8—N7104.3 (6)
S8—C81—C82—C83179.2 (9)C82—C81—S8—N775.5 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C86—H86···O10.932.552.917 (10)104
N2—H2···N7i0.72 (8)2.19 (9)2.911 (8)173 (9)
C83—H83···Br1Bii0.932.923.63 (2)134
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+1, y+2, z+1.
Methyl 2-{[(5,6-diphenyl-1,2,4-triazin-3-yl)sulfamoyl]methyl}benzoate (3b) top
Crystal data top
C24H20N4O4SF(000) = 960
Mr = 460.50Dx = 1.402 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54178 Å
a = 10.919 (2) ÅCell parameters from 3956 reflections
b = 8.0871 (16) Åθ = 4.6–75.6°
c = 24.875 (5) ŵ = 1.66 mm1
β = 96.65 (3)°T = 120 K
V = 2181.9 (8) Å3Plate, yellow
Z = 40.30 × 0.10 × 0.10 mm
Data collection top
Agilent SuperNova Single Source
diffractometer with an Atlas detector
4438 independent reflections
Radiation source: sealed X-ray tube, SuperNova (Cu) X-ray Source3507 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.049
Detector resolution: 5.2763 pixels mm-1θmax = 76.5°, θmin = 3.6°
ω scansh = 1313
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
k = 810
Tmin = 0.782, Tmax = 1.000l = 3131
8470 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.070H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.253 w = 1/[σ2(Fo2) + (0.128P)2 + 2.0409P]
where P = (Fo2 + 2Fc2)/3
S = 1.18(Δ/σ)max < 0.001
4438 reflectionsΔρmax = 0.64 e Å3
302 parametersΔρmin = 1.16 e Å3
18 restraintsExtinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0015 (4)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C30.5856 (3)0.3397 (4)0.63161 (13)0.0288 (5)
C50.5785 (3)0.3612 (4)0.72213 (13)0.0277 (5)
C60.7094 (3)0.3482 (4)0.72907 (14)0.0270 (7)
C90.3271 (3)0.5231 (5)0.59242 (14)0.0313 (7)
H9A0.34910.51770.63130.047*
H9B0.36990.61670.57890.047*
C100.2111 (3)0.7638 (4)0.50776 (13)0.0317 (7)
C120.2140 (4)0.9891 (5)0.44913 (17)0.0437 (10)
H12A0.15991.07190.43190.066*
H12B0.28001.04170.47170.066*
H12C0.24730.92390.42200.066*
C510.4987 (3)0.3849 (4)0.76596 (13)0.0275 (7)
C520.3845 (4)0.3033 (5)0.76124 (15)0.0357 (8)
H520.36230.23280.73220.054*
C530.3049 (4)0.3280 (6)0.80003 (17)0.0434 (10)
H530.23060.27080.79770.065*
C540.3355 (4)0.4375 (6)0.84228 (16)0.0437 (10)
H540.28100.45540.86780.066*
C550.4468 (4)0.5200 (5)0.84652 (15)0.0409 (9)
H550.46720.59290.87500.061*
C560.5284 (4)0.4948 (5)0.80845 (15)0.0347 (8)
H560.60300.55150.81140.052*
C610.7902 (3)0.3471 (4)0.78100 (14)0.0269 (7)
C620.7635 (3)0.2545 (4)0.82579 (13)0.0294 (7)
H620.69180.19160.82370.044*
C630.8441 (4)0.2566 (5)0.87351 (14)0.0358 (8)
H630.82660.19330.90290.054*
C640.9502 (4)0.3522 (5)0.87750 (16)0.0366 (8)
H641.00250.35540.90980.055*
C650.9778 (3)0.4429 (5)0.83323 (16)0.0361 (8)
H651.04870.50740.83580.054*
C660.9003 (3)0.4378 (4)0.78517 (15)0.0328 (7)
H660.92140.49540.75520.049*
C910.1909 (3)0.5496 (4)0.58061 (13)0.0292 (7)
C920.1358 (3)0.6610 (4)0.54204 (14)0.0311 (7)
C930.0076 (4)0.6795 (5)0.53476 (17)0.0387 (9)
H930.02890.75370.50920.058*
C940.0648 (4)0.5872 (5)0.56568 (18)0.0435 (9)
H940.15010.59890.56050.065*
C950.0117 (4)0.4778 (5)0.60419 (17)0.0393 (9)
H950.06080.41620.62490.059*
C960.1151 (4)0.4607 (5)0.61166 (15)0.0373 (8)
H960.15070.38830.63800.056*
N10.7690 (3)0.3342 (4)0.68541 (12)0.0294 (6)
N20.7092 (3)0.3326 (4)0.63565 (12)0.0312 (7)
N40.5187 (3)0.3534 (4)0.67275 (11)0.0280 (5)
N70.5258 (3)0.3388 (4)0.57955 (11)0.0300 (5)
H70.574 (4)0.320 (6)0.553 (2)0.045*
O10.3236 (2)0.1997 (3)0.58655 (11)0.0370 (6)
O20.3626 (3)0.3521 (4)0.50456 (10)0.0386 (7)
O100.3196 (2)0.7421 (4)0.50363 (11)0.0386 (6)
O110.1456 (3)0.8832 (3)0.48194 (12)0.0413 (7)
S80.37658 (8)0.33808 (11)0.56239 (3)0.0303 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C30.0326 (10)0.0314 (10)0.0231 (10)0.0025 (8)0.0067 (9)0.0005 (8)
C50.0343 (11)0.0256 (11)0.0237 (11)0.0008 (9)0.0061 (10)0.0001 (9)
C60.0354 (17)0.0196 (14)0.0279 (16)0.0004 (12)0.0117 (13)0.0002 (11)
C90.0347 (17)0.0321 (17)0.0268 (15)0.0030 (14)0.0022 (13)0.0003 (13)
C100.0399 (18)0.0305 (17)0.0257 (15)0.0045 (15)0.0079 (13)0.0025 (13)
C120.065 (3)0.0289 (18)0.039 (2)0.0013 (18)0.0127 (18)0.0037 (16)
C510.0317 (16)0.0265 (15)0.0254 (15)0.0038 (13)0.0084 (12)0.0011 (12)
C520.0380 (19)0.0368 (18)0.0333 (17)0.0025 (16)0.0080 (15)0.0022 (15)
C530.041 (2)0.050 (2)0.043 (2)0.0018 (18)0.0226 (18)0.0023 (17)
C540.045 (2)0.053 (2)0.0350 (19)0.0118 (19)0.0165 (16)0.0044 (17)
C550.051 (2)0.040 (2)0.0324 (18)0.0123 (18)0.0098 (16)0.0068 (15)
C560.0414 (19)0.0305 (17)0.0330 (17)0.0014 (15)0.0079 (15)0.0030 (14)
C610.0316 (17)0.0214 (15)0.0285 (16)0.0025 (12)0.0068 (13)0.0023 (12)
C620.0341 (17)0.0272 (16)0.0269 (15)0.0023 (14)0.0036 (13)0.0002 (12)
C630.049 (2)0.0330 (18)0.0258 (16)0.0070 (16)0.0042 (15)0.0000 (13)
C640.0399 (19)0.0347 (19)0.0334 (18)0.0083 (16)0.0041 (15)0.0067 (14)
C650.0339 (18)0.0318 (18)0.0405 (19)0.0019 (15)0.0042 (15)0.0021 (15)
C660.0357 (18)0.0272 (16)0.0359 (17)0.0033 (14)0.0058 (14)0.0015 (14)
C910.0319 (16)0.0303 (16)0.0270 (15)0.0016 (14)0.0101 (13)0.0046 (13)
C920.0344 (18)0.0293 (17)0.0320 (17)0.0018 (14)0.0135 (14)0.0048 (13)
C930.039 (2)0.0352 (19)0.043 (2)0.0082 (16)0.0110 (16)0.0042 (16)
C940.0368 (19)0.042 (2)0.055 (2)0.0007 (17)0.0168 (17)0.0087 (18)
C950.0359 (19)0.0380 (19)0.048 (2)0.0018 (16)0.0204 (16)0.0038 (17)
C960.046 (2)0.0319 (18)0.0366 (18)0.0013 (16)0.0165 (16)0.0013 (15)
N10.0338 (15)0.0297 (14)0.0246 (13)0.0019 (11)0.0028 (11)0.0006 (11)
N20.0337 (15)0.0329 (15)0.0279 (14)0.0024 (12)0.0077 (12)0.0017 (11)
N40.0333 (10)0.0285 (10)0.0228 (9)0.0018 (8)0.0051 (8)0.0004 (7)
N70.0327 (11)0.0357 (11)0.0219 (10)0.0033 (9)0.0045 (9)0.0007 (9)
O10.0402 (14)0.0316 (13)0.0391 (14)0.0023 (11)0.0042 (11)0.0011 (11)
O20.0453 (15)0.0470 (16)0.0231 (12)0.0057 (12)0.0027 (11)0.0033 (10)
O100.0352 (13)0.0476 (16)0.0354 (13)0.0066 (12)0.0144 (11)0.0093 (12)
O110.0489 (16)0.0319 (13)0.0445 (15)0.0081 (12)0.0109 (12)0.0083 (12)
S80.0347 (5)0.0320 (5)0.0248 (4)0.0016 (3)0.0063 (3)0.0021 (3)
Geometric parameters (Å, º) top
C3—N41.329 (4)C55—H550.9300
C3—N21.342 (5)C56—H560.9300
C3—N71.381 (4)C61—C621.401 (5)
C5—N41.324 (4)C61—C661.401 (5)
C5—C61.424 (5)C62—C631.394 (5)
C5—C511.484 (4)C62—H620.9300
C6—N11.334 (4)C63—C641.387 (6)
C6—C611.478 (5)C63—H630.9300
C9—C911.498 (5)C64—C651.385 (6)
C9—S81.784 (4)C64—H640.9300
C9—H9A0.9700C65—C661.383 (5)
C9—H9B0.9700C65—H650.9300
C10—O101.213 (4)C66—H660.9300
C10—O111.323 (5)C91—C961.395 (5)
C10—C921.502 (5)C91—C921.400 (5)
C12—O111.448 (5)C92—C931.398 (5)
C12—H12A0.9600C93—C941.384 (6)
C12—H12B0.9600C93—H930.9300
C12—H12C0.9600C94—C951.381 (6)
C51—C561.390 (5)C94—H940.9300
C51—C521.404 (5)C95—C961.382 (6)
C52—C531.386 (5)C95—H950.9300
C52—H520.9300C96—H960.9300
C53—C541.385 (6)N1—N21.331 (4)
C53—H530.9300N7—S81.636 (3)
C54—C551.379 (6)N7—H70.90 (5)
C54—H540.9300O1—S81.425 (3)
C55—C561.389 (5)O2—S81.434 (3)
N4—C3—N2125.7 (3)C63—C62—H62119.9
N4—C3—N7118.7 (3)C61—C62—H62119.9
N2—C3—N7115.6 (3)C64—C63—C62120.5 (3)
N4—C5—C6119.3 (3)C64—C63—H63119.7
N4—C5—C51114.8 (3)C62—C63—H63119.7
C6—C5—C51125.9 (3)C65—C64—C63119.7 (4)
N1—C6—C5119.0 (3)C65—C64—H64120.2
N1—C6—C61114.4 (3)C63—C64—H64120.2
C5—C6—C61126.6 (3)C66—C65—C64120.3 (4)
C91—C9—S8112.3 (2)C66—C65—H65119.9
C91—C9—H9A109.1C64—C65—H65119.9
S8—C9—H9A109.1C65—C66—C61120.9 (3)
C91—C9—H9B109.1C65—C66—H66119.6
S8—C9—H9B109.1C61—C66—H66119.6
H9A—C9—H9B107.9C96—C91—C92118.3 (3)
O10—C10—O11122.9 (3)C96—C91—C9117.2 (3)
O10—C10—C92124.9 (3)C92—C91—C9124.4 (3)
O11—C10—C92112.2 (3)C93—C92—C91120.1 (3)
O11—C12—H12A109.5C93—C92—C10118.2 (3)
O11—C12—H12B109.5C91—C92—C10121.6 (3)
H12A—C12—H12B109.5C94—C93—C92119.9 (4)
O11—C12—H12C109.5C94—C93—H93120.1
H12A—C12—H12C109.5C92—C93—H93120.1
H12B—C12—H12C109.5C95—C94—C93120.6 (4)
C56—C51—C52119.4 (3)C95—C94—H94119.7
C56—C51—C5122.4 (3)C93—C94—H94119.7
C52—C51—C5118.0 (3)C94—C95—C96119.4 (4)
C53—C52—C51119.8 (4)C94—C95—H95120.3
C53—C52—H52120.1C96—C95—H95120.3
C51—C52—H52120.1C95—C96—C91121.6 (4)
C54—C53—C52120.3 (4)C95—C96—H96119.2
C54—C53—H53119.8C91—C96—H96119.2
C52—C53—H53119.8N2—N1—C6121.7 (3)
C55—C54—C53120.0 (3)N1—N2—C3116.7 (3)
C55—C54—H54120.0C5—N4—C3117.5 (3)
C53—C54—H54120.0C3—N7—S8126.4 (3)
C54—C55—C56120.4 (4)C3—N7—H7116 (3)
C54—C55—H55119.8S8—N7—H7117 (3)
C56—C55—H55119.8C10—O11—C12114.8 (3)
C55—C56—C51120.0 (4)O1—S8—O2118.97 (18)
C55—C56—H56120.0O1—S8—N7109.51 (16)
C51—C56—H56120.0O2—S8—N7104.40 (16)
C62—C61—C66118.5 (3)O1—S8—C9108.95 (17)
C62—C61—C6122.7 (3)O2—S8—C9110.58 (17)
C66—C61—C6118.8 (3)N7—S8—C9103.20 (16)
C63—C62—C61120.1 (3)
N4—C5—C6—N12.4 (5)C96—C91—C92—C10178.8 (3)
C51—C5—C6—N1177.1 (3)C9—C91—C92—C101.1 (5)
N4—C5—C6—C61177.2 (3)O10—C10—C92—C93167.7 (4)
C51—C5—C6—C613.3 (5)O11—C10—C92—C9312.3 (5)
N4—C5—C51—C56136.7 (4)O10—C10—C92—C9112.6 (6)
C6—C5—C51—C5642.8 (5)O11—C10—C92—C91167.4 (3)
N4—C5—C51—C5237.7 (5)C91—C92—C93—C940.2 (6)
C6—C5—C51—C52142.8 (4)C10—C92—C93—C94179.9 (3)
C56—C51—C52—C532.5 (6)C92—C93—C94—C950.7 (6)
C5—C51—C52—C53177.1 (4)C93—C94—C95—C960.1 (6)
C51—C52—C53—C542.4 (7)C94—C95—C96—C911.0 (6)
C52—C53—C54—C551.3 (7)C92—C91—C96—C951.5 (6)
C53—C54—C55—C560.4 (6)C9—C91—C96—C95179.4 (3)
C54—C55—C56—C510.5 (6)C5—C6—N1—N20.1 (5)
C52—C51—C56—C551.6 (6)C61—C6—N1—N2179.7 (3)
C5—C51—C56—C55175.9 (3)C6—N1—N2—C32.3 (5)
N1—C6—C61—C62135.4 (3)N4—C3—N2—N12.2 (5)
C5—C6—C61—C6244.2 (5)N7—C3—N2—N1179.6 (3)
N1—C6—C61—C6642.4 (4)C6—C5—N4—C32.5 (5)
C5—C6—C61—C66138.0 (3)C51—C5—N4—C3177.1 (3)
C66—C61—C62—C631.3 (5)N2—C3—N4—C50.2 (5)
C6—C61—C62—C63179.1 (3)N7—C3—N4—C5177.1 (3)
C61—C62—C63—C641.2 (5)N4—C3—N7—S85.3 (5)
C62—C63—C64—C651.7 (6)N2—C3—N7—S8177.1 (3)
C63—C64—C65—C660.2 (6)O10—C10—O11—C121.3 (5)
C64—C65—C66—C612.7 (6)C92—C10—O11—C12178.6 (3)
C62—C61—C66—C653.2 (5)C3—N7—S8—O156.5 (3)
C6—C61—C66—C65178.9 (3)C3—N7—S8—O2175.0 (3)
S8—C9—C91—C9679.8 (3)C3—N7—S8—C959.4 (3)
S8—C9—C91—C92102.5 (4)C91—C9—S8—O164.9 (3)
C96—C91—C92—C930.9 (5)C91—C9—S8—O267.6 (3)
C9—C91—C92—C93178.6 (3)C91—C9—S8—N7178.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···N40.972.413.047 (4)123
C9—H9B···O100.972.142.825 (5)126
C93—H93···O110.932.342.678 (5)101
N7—H7···O10i0.90 (5)1.99 (5)2.893 (4)175 (4)
C12—H12···N2i0.962.603.512 (5)159
C63—H63···O2ii0.932.543.360 (4)147
C95—H95···N1iii0.932.613.505 (5)162
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1/2, y+1/2, z+1/2; (iii) x1, y, z.
Selected bond lengths (Å) and torsion angles (°) top
Bond3a3b
N1—N21.341 (6)1.340 (8)
N2—C31.331 (4)1.342 (5)
N4—C31.354 (8)1.329 (4)
N4—C51.326 (7)1.439 (8)
C5—C61.317 (8)1.328 (7)
N1—C61.324 (4)1.424 (5)
N7—C31.334 (4)1.381 (4)
Torsion angle
N2—C3—N7—S8-175.7 (5)177.1 (3)
C3—N7—S8—C8166.4 (6)
N7—S8—C81—C8275.5 (7)
C3—N7—S8—C959.4 (3)
N7—S8—C9—C91178.8 (2)
S8—C9—C91—C92-102.5 (4)
O1—S8—N7—C3-50.7 (6)-56.5 (3)
O2—S8—C7—N3179.8 (5)175.0 (3)
N4—C5—C511—C5227.3 (9)37.7 (5)
N1—C6—C61—C62-119.5 (6)-135.4 (3)
C91—C92—C10—O11-167.4 (3)
C92—C10—O11—C12178.6 (3)
C91—C92—C10—O1012.6 (6)
Relative energies ΔEZPE (kcal mol-1) and tautomeric forms populations Pi (%) for 3a and 3b top
Compound 3aΔEZPE (Pi)
Tautomeric formN2—HN4—HN7—H
Gas phase4.83 (0.02)9.91 (0.00)0.00 (99.98)
Chloroform, ε = 4.41131.45 (7.64)7.41 (0.00)0.00 (92.36)
Ethanol, ε = 24.85200.25 (39.39)6.46 (0.00)0.00 (60.61)
Water, ε = 78.35530.06 (47.31)6.27 (0.00)0.00 (52.69)
Compound 3bΔEZPE (Pi)
Tautomeric formN2—HN4—HN7—H
Gas phase6.09 (0.00)10.54 (0.00)0.00 (100.00)
Chloroform, ε = 4.41132.07 (2.77)7.84 (0.00)0.00 (97.23)
Ethanol, ε = 24.85200.63 (25.39)6.71 (0.00)0.00 (74.61)
Water, ε = 78.35530.37 (34.37)6.53 (0.00)0.00 (65.63)
 

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