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In 2,3-di(thio­phen-2-yl)pyrido[2,3-b]pyrazine the thienyl rings are inclined to the mean plane of the pyrido­pyrazine moiety by 6.16 (7) and 86.66 (8)°, where as in the bromo derivative, 7-bromo-2,3-bis­(thio­phen-2-yl)pyrido[2,3-b] pyrazine, the corresponding dihedral angles are 33.29 (11) and 19.84 (9)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989018016882/xi2011sup1.cif
Contains datablocks 1, Global, 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989018016882/xi20111sup2.hkl
Contains datablock 1

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989018016882/xi20111sup4.cml
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989018016882/xi20112sup3.hkl
Contains datablock 2

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989018016882/xi20112sup5.cml
Supplementary material

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2056989018016882/xi2011sup6.pdf
NMRs and FTIRs of 1 and 2

CCDC references: 1881685; 1881684

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.048
  • wR factor = 0.148
  • Data-to-parameter ratio = 26.3

checkCIF/PLATON results

No syntax errors found



Datablock: 1


Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C14 --C15 . 8.4 s.u.
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C9 --C10 . 5.9 s.u. PLAT241_ALERT_2_C High 'MainMol' Ueq as Compared to Neighbors of S2 Check PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min). 8 Note PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 11 Report
Alert level G PLAT005_ALERT_5_G No Embedded Refinement Details Found in the CIF Please Do ! PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 301 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 10 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 4 ALERT level C = Check. Ensure it is not caused by an omission or oversight 5 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
Datablock: 2
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for S1 --C8 . 8.4 s.u. PLAT230_ALERT_2_B Hirshfeld Test Diff for C8 --C9 . 8.1 s.u. PLAT230_ALERT_2_B Hirshfeld Test Diff for C9 --C10 . 9.5 s.u. PLAT910_ALERT_3_B Missing # of FCF Reflection(s) Below Theta(Min). 12 Note
Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H3 ..BR1 . 3.01 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H5 ..BR1 . 3.05 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H15 ..N1 . 2.64 Ang. PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 3.170 Check PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 10 Report
Alert level G PLAT005_ALERT_5_G No Embedded Refinement Details Found in the CIF Please Do ! PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 443 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 9 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 4 ALERT level B = A potentially serious problem, consider carefully 5 ALERT level C = Check. Ensure it is not caused by an omission or oversight 5 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Computing details top

For both structures, data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

2,3-Bis(thiophen-2-yl)pyrido[2,3-b]pyrazine (1) top
Crystal data top
C15H9N3S2Dx = 1.491 Mg m3
Mr = 295.37Melting point: 451 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 5.25147 (12) ÅCell parameters from 6256 reflections
b = 14.1093 (3) Åθ = 4.5–32.1°
c = 17.7690 (3) ŵ = 0.40 mm1
β = 92.0296 (18)°T = 293 K
V = 1315.76 (4) Å3Plate, yellow
Z = 40.43 × 0.33 × 0.21 mm
F(000) = 608
Data collection top
Rigaku Xcalibur Sapphire3
diffractometer
4763 independent reflections
Radiation source: Enhance (Mo) X-ray Source3491 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
Detector resolution: 16.1790 pixels mm-1θmax = 33.3°, θmin = 4.1°
ω scansh = 86
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2018)
k = 2121
Tmin = 0.948, Tmax = 1.000l = 2726
19251 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.048 w = 1/[σ2(Fo2) + (0.0773P)2 + 0.306P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.148(Δ/σ)max < 0.001
S = 1.01Δρmax = 0.44 e Å3
4763 reflectionsΔρmin = 0.40 e Å3
181 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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 > 2sigma(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
xyzUiso*/Ueq
S10.29005 (9)0.07264 (3)0.05184 (3)0.05601 (15)
S20.68406 (10)0.36939 (5)0.21271 (3)0.0735 (2)
N30.8135 (2)0.37660 (8)0.02149 (7)0.0390 (3)
N10.6466 (3)0.19393 (8)0.01845 (7)0.0407 (3)
C10.5489 (3)0.23948 (9)0.03890 (7)0.0358 (3)
C70.6384 (3)0.33311 (9)0.05955 (7)0.0356 (3)
C80.3498 (3)0.18831 (9)0.07804 (8)0.0371 (3)
C120.5459 (3)0.38619 (10)0.12539 (8)0.0401 (3)
C20.8310 (3)0.23713 (10)0.05676 (8)0.0387 (3)
C60.9139 (3)0.32947 (10)0.03738 (8)0.0381 (3)
N20.9315 (3)0.18788 (10)0.11470 (8)0.0531 (3)
C110.0556 (4)0.06156 (12)0.11368 (11)0.0539 (4)
H110.03800.00630.11980.065*
C90.1873 (3)0.21596 (11)0.13489 (9)0.0439 (3)
H90.18940.27530.15760.053*
C100.0188 (3)0.14123 (12)0.15320 (10)0.0523 (4)
H100.10500.14700.18910.063*
C51.1070 (3)0.37201 (11)0.07888 (10)0.0483 (3)
H51.16470.43290.06760.058*
C41.2062 (4)0.32159 (14)0.13583 (10)0.0532 (4)
H41.33480.34710.16420.064*
C31.1122 (4)0.23039 (14)0.15125 (10)0.0567 (4)
H31.18350.19730.19060.068*
C130.3588 (4)0.45253 (13)0.12665 (11)0.0561 (4)
H130.26290.47180.08440.067*
C150.4890 (4)0.45263 (18)0.25111 (12)0.0691 (6)
H150.49640.47010.30160.083*
C140.3271 (5)0.48905 (15)0.20032 (13)0.0655 (5)
H140.20470.53400.21160.079*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0634 (3)0.0423 (2)0.0634 (3)0.00914 (17)0.0164 (2)0.01125 (18)
S20.0567 (3)0.1255 (5)0.0382 (2)0.0178 (3)0.00148 (19)0.0182 (3)
N30.0466 (6)0.0332 (5)0.0375 (6)0.0006 (4)0.0055 (5)0.0017 (4)
N10.0509 (6)0.0359 (6)0.0356 (6)0.0007 (5)0.0059 (5)0.0035 (4)
C10.0410 (6)0.0336 (6)0.0327 (6)0.0021 (5)0.0022 (5)0.0003 (5)
C70.0407 (6)0.0335 (6)0.0327 (6)0.0022 (5)0.0018 (5)0.0016 (5)
C80.0419 (6)0.0331 (6)0.0365 (6)0.0003 (5)0.0031 (5)0.0011 (5)
C120.0448 (7)0.0396 (7)0.0363 (6)0.0041 (5)0.0049 (5)0.0068 (5)
C20.0473 (7)0.0361 (6)0.0329 (6)0.0031 (5)0.0053 (5)0.0010 (5)
C60.0455 (7)0.0352 (6)0.0337 (6)0.0023 (5)0.0046 (5)0.0013 (5)
N20.0690 (9)0.0478 (7)0.0437 (7)0.0010 (6)0.0165 (6)0.0107 (6)
C110.0544 (9)0.0437 (8)0.0639 (11)0.0095 (7)0.0064 (8)0.0063 (7)
C90.0480 (7)0.0358 (6)0.0487 (8)0.0013 (6)0.0157 (6)0.0026 (6)
C100.0527 (9)0.0508 (9)0.0544 (9)0.0041 (7)0.0159 (7)0.0061 (7)
C50.0544 (9)0.0436 (8)0.0474 (8)0.0045 (6)0.0103 (7)0.0025 (6)
C40.0563 (9)0.0572 (10)0.0474 (8)0.0011 (7)0.0173 (7)0.0046 (7)
C30.0684 (11)0.0590 (10)0.0439 (8)0.0037 (8)0.0201 (8)0.0072 (7)
C130.0728 (11)0.0462 (8)0.0495 (9)0.0139 (8)0.0069 (8)0.0080 (7)
C150.0678 (11)0.0904 (15)0.0505 (10)0.0221 (11)0.0229 (9)0.0331 (10)
C140.0807 (13)0.0528 (10)0.0645 (12)0.0034 (9)0.0221 (10)0.0199 (9)
Geometric parameters (Å, º) top
S1—C81.7229 (14)N2—C31.314 (2)
S1—C111.686 (2)C11—H110.9300
S2—C121.7060 (15)C11—C101.343 (3)
S2—C151.716 (2)C9—H90.9300
N3—C71.3131 (18)C9—C101.422 (2)
N3—C61.3613 (18)C10—H100.9300
N1—C11.3236 (18)C5—H50.9300
N1—C21.3486 (19)C5—C41.356 (2)
C1—C71.4452 (19)C4—H40.9300
C1—C81.466 (2)C4—C31.402 (3)
C7—C121.4852 (19)C3—H30.9300
C8—C91.401 (2)C13—H130.9300
C12—C131.358 (2)C13—C141.422 (3)
C2—C61.413 (2)C15—H150.9300
C2—N21.3637 (19)C15—C141.322 (4)
C6—C51.409 (2)C14—H140.9300
C11—S1—C892.41 (8)C10—C11—H11123.7
C12—S2—C1591.49 (10)C8—C9—H9124.5
C7—N3—C6117.71 (12)C8—C9—C10111.02 (14)
C1—N1—C2118.29 (12)C10—C9—H9124.5
N1—C1—C7120.52 (12)C11—C10—C9113.49 (16)
N1—C1—C8115.38 (12)C11—C10—H10123.3
C7—C1—C8124.10 (12)C9—C10—H10123.3
N3—C7—C1121.59 (12)C6—C5—H5121.0
N3—C7—C12115.14 (12)C4—C5—C6118.02 (15)
C1—C7—C12123.26 (12)C4—C5—H5121.0
C1—C8—S1117.68 (10)C5—C4—H4120.5
C9—C8—S1110.41 (11)C5—C4—C3119.03 (15)
C9—C8—C1131.91 (13)C3—C4—H4120.5
C7—C12—S2120.39 (11)N2—C3—C4125.32 (15)
C13—C12—S2111.44 (12)N2—C3—H3117.3
C13—C12—C7128.15 (15)C4—C3—H3117.3
N1—C2—C6120.97 (12)C12—C13—H13124.0
N1—C2—N2117.05 (13)C12—C13—C14111.93 (18)
N2—C2—C6121.98 (14)C14—C13—H13124.0
N3—C6—C2120.89 (13)S2—C15—H15124.0
N3—C6—C5119.97 (13)C14—C15—S2111.93 (15)
C5—C6—C2119.13 (13)C14—C15—H15124.0
C3—N2—C2116.51 (14)C13—C14—H14123.4
S1—C11—H11123.7C15—C14—C13113.20 (18)
C10—C11—S1112.65 (13)C15—C14—H14123.4
S1—C8—C9—C100.99 (18)C7—C12—C13—C14178.93 (16)
S1—C11—C10—C90.9 (2)C8—S1—C11—C100.26 (16)
S2—C12—C13—C140.7 (2)C8—C1—C7—N3178.50 (13)
S2—C15—C14—C131.6 (3)C8—C1—C7—C122.9 (2)
N3—C7—C12—S292.59 (15)C8—C9—C10—C111.2 (2)
N3—C7—C12—C1385.5 (2)C12—S2—C15—C141.07 (18)
N3—C6—C5—C4178.33 (15)C12—C13—C14—C151.5 (3)
N1—C1—C7—N31.6 (2)C2—N1—C1—C70.0 (2)
N1—C1—C7—C12176.99 (13)C2—N1—C1—C8179.89 (12)
N1—C1—C8—S16.41 (17)C2—C6—C5—C40.4 (2)
N1—C1—C8—C9172.69 (15)C2—N2—C3—C40.6 (3)
N1—C2—C6—N31.3 (2)C6—N3—C7—C11.7 (2)
N1—C2—C6—C5179.99 (14)C6—N3—C7—C12177.03 (12)
N1—C2—N2—C3179.52 (16)C6—C2—N2—C30.7 (2)
C1—N1—C2—C61.4 (2)C6—C5—C4—C30.5 (3)
C1—N1—C2—N2178.84 (14)N2—C2—C6—N3178.93 (14)
C1—C7—C12—S286.08 (16)N2—C2—C6—C50.3 (2)
C1—C7—C12—C1395.8 (2)C11—S1—C8—C1178.84 (12)
C1—C8—C9—C10178.15 (15)C11—S1—C8—C90.44 (13)
C7—N3—C6—C20.3 (2)C5—C4—C3—N20.0 (3)
C7—N3—C6—C5178.40 (13)C15—S2—C12—C7178.22 (13)
C7—C1—C8—S1173.50 (11)C15—S2—C12—C130.19 (15)
C7—C1—C8—C97.4 (2)
7-Bromo-2,3-bis(thiophen-2-yl)pyrido[2,3-b]pyrazine (2) top
Crystal data top
C15H8BrN3S2Dx = 1.747 Mg m3
Mr = 374.27Melting point: 445 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 5.8336 (2) ÅCell parameters from 9441 reflections
b = 29.4731 (10) Åθ = 4.5–32.2°
c = 8.3160 (3) ŵ = 3.18 mm1
β = 95.466 (3)°T = 293 K
V = 1423.30 (9) Å3Plate, yellow
Z = 40.33 × 0.24 × 0.22 mm
F(000) = 744
Data collection top
Rigaku Xcalibur Sapphire3
diffractometer
5255 independent reflections
Radiation source: Enhance (Mo) X-ray Source4166 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
Detector resolution: 16.1790 pixels mm-1θmax = 33.9°, θmin = 4.2°
ω scansh = 88
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2018)
k = 4545
Tmin = 0.455, Tmax = 1.000l = 1212
34519 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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0474P)2 + 0.940P]
where P = (Fo2 + 2Fc2)/3
5255 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.63 e Å3
0 restraintsΔρmin = 0.67 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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 > 2sigma(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
xyzUiso*/Ueq
Br10.69446 (4)0.018840 (9)0.30276 (3)0.04319 (9)
S20.62946 (10)0.11087 (2)0.49251 (7)0.04132 (14)
S11.54351 (12)0.19256 (2)0.09942 (10)0.05248 (18)
N30.8311 (3)0.08963 (6)0.1758 (2)0.0312 (3)
C120.8921 (3)0.13124 (7)0.4089 (3)0.0294 (4)
C70.9600 (3)0.12031 (7)0.2402 (2)0.0290 (4)
C21.1218 (4)0.08478 (7)0.0484 (3)0.0314 (4)
C60.9043 (3)0.07298 (7)0.0283 (2)0.0290 (4)
C131.0082 (4)0.15121 (8)0.5255 (3)0.0354 (4)
H131.15490.16350.50560.042*
N11.2404 (3)0.11997 (7)0.0083 (2)0.0342 (4)
N21.2152 (4)0.06423 (8)0.1847 (3)0.0428 (5)
C11.1566 (4)0.13963 (7)0.1436 (3)0.0298 (4)
C50.7682 (4)0.04198 (8)0.0495 (3)0.0327 (4)
H50.61980.03460.00660.039*
C40.8620 (4)0.02319 (7)0.1898 (3)0.0330 (4)
C81.2653 (4)0.18271 (7)0.1791 (3)0.0331 (4)
C140.8825 (4)0.15116 (8)0.6789 (3)0.0386 (5)
H140.93660.16370.77070.046*
C150.6754 (4)0.13092 (8)0.6780 (3)0.0395 (5)
H150.56990.12830.76860.047*
C31.0885 (4)0.03388 (9)0.2503 (3)0.0413 (5)
H31.15210.01860.34190.050*
C91.1615 (5)0.22302 (8)0.2534 (3)0.0445 (6)
H91.01130.22550.30130.053*
C101.3303 (6)0.25845 (9)0.2402 (4)0.0575 (8)
H101.30040.28740.28170.069*
C111.5344 (6)0.24684 (10)0.1638 (4)0.0589 (8)
H111.65840.26670.14790.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.04705 (15)0.04449 (14)0.03805 (13)0.00908 (10)0.00417 (10)0.01197 (10)
S20.0361 (3)0.0475 (3)0.0388 (3)0.0120 (2)0.0047 (2)0.0046 (2)
S10.0458 (3)0.0422 (3)0.0694 (5)0.0123 (3)0.0051 (3)0.0048 (3)
N30.0301 (8)0.0319 (9)0.0308 (8)0.0037 (7)0.0023 (6)0.0041 (7)
C120.0274 (9)0.0279 (9)0.0320 (9)0.0004 (7)0.0016 (7)0.0012 (7)
C70.0294 (9)0.0272 (9)0.0301 (9)0.0005 (7)0.0007 (7)0.0005 (7)
C20.0304 (9)0.0329 (10)0.0299 (9)0.0045 (8)0.0019 (7)0.0015 (8)
C60.0291 (9)0.0282 (9)0.0291 (9)0.0034 (7)0.0003 (7)0.0006 (7)
C130.0326 (10)0.0393 (11)0.0337 (10)0.0016 (9)0.0010 (8)0.0031 (9)
N10.0333 (9)0.0353 (9)0.0327 (9)0.0084 (7)0.0031 (7)0.0012 (7)
N20.0382 (10)0.0502 (12)0.0376 (10)0.0112 (9)0.0093 (8)0.0104 (9)
C10.0306 (9)0.0267 (9)0.0323 (10)0.0038 (7)0.0037 (7)0.0003 (7)
C50.0306 (9)0.0343 (10)0.0323 (10)0.0057 (8)0.0012 (8)0.0021 (8)
C40.0370 (10)0.0316 (10)0.0306 (10)0.0021 (8)0.0041 (8)0.0027 (8)
C80.0367 (10)0.0285 (9)0.0345 (10)0.0057 (8)0.0058 (8)0.0030 (8)
C140.0479 (13)0.0365 (11)0.0313 (10)0.0003 (9)0.0031 (9)0.0030 (8)
C150.0481 (13)0.0368 (11)0.0314 (11)0.0015 (10)0.0085 (9)0.0011 (8)
C30.0432 (12)0.0451 (13)0.0334 (11)0.0070 (10)0.0076 (9)0.0106 (9)
C90.0523 (14)0.0343 (12)0.0476 (13)0.0153 (10)0.0085 (11)0.0000 (10)
C100.075 (2)0.0290 (12)0.072 (2)0.0045 (12)0.0257 (16)0.0035 (12)
C110.0594 (18)0.0402 (14)0.080 (2)0.0221 (13)0.0240 (16)0.0075 (14)
Geometric parameters (Å, º) top
Br1—C41.884 (2)N1—C11.318 (3)
S2—C121.729 (2)N2—C31.312 (3)
S2—C151.697 (2)C1—C81.462 (3)
S1—C81.718 (2)C5—H50.9300
S1—C111.686 (3)C5—C41.358 (3)
N3—C71.321 (3)C4—C31.404 (3)
N3—C61.352 (3)C8—C91.446 (4)
C12—C71.457 (3)C14—H140.9300
C12—C131.368 (3)C14—C151.348 (3)
C7—C11.452 (3)C15—H150.9300
C2—C61.408 (3)C3—H30.9300
C2—N11.356 (3)C9—H90.9300
C2—N21.353 (3)C9—C101.432 (4)
C6—C51.408 (3)C10—H100.9300
C13—H130.9300C10—C111.339 (5)
C13—C141.410 (3)C11—H110.9300
C15—S2—C1291.95 (11)C4—C5—H5121.3
C11—S1—C892.17 (14)C5—C4—Br1120.71 (17)
C7—N3—C6118.26 (18)C5—C4—C3120.3 (2)
C7—C12—S2117.37 (15)C3—C4—Br1118.93 (17)
C13—C12—S2110.13 (16)C1—C8—S1118.76 (17)
C13—C12—C7132.08 (19)C9—C8—S1111.58 (17)
N3—C7—C12115.37 (18)C9—C8—C1128.9 (2)
N3—C7—C1119.60 (18)C13—C14—H14123.7
C1—C7—C12125.02 (18)C15—C14—C13112.6 (2)
N1—C2—C6119.96 (19)C15—C14—H14123.7
N2—C2—C6122.8 (2)S2—C15—H15123.9
N2—C2—N1117.08 (19)C14—C15—S2112.24 (17)
N3—C6—C2120.93 (19)C14—C15—H15123.9
N3—C6—C5120.64 (18)N2—C3—C4123.5 (2)
C5—C6—C2118.38 (19)N2—C3—H3118.3
C12—C13—H13123.5C4—C3—H3118.3
C12—C13—C14113.0 (2)C8—C9—H9126.0
C14—C13—H13123.5C10—C9—C8108.0 (3)
C1—N1—C2118.22 (18)C10—C9—H9126.0
C3—N2—C2117.1 (2)C9—C10—H10122.5
C7—C1—C8124.32 (19)C11—C10—C9115.1 (3)
N1—C1—C7120.60 (18)C11—C10—H10122.5
N1—C1—C8114.94 (19)S1—C11—H11123.4
C6—C5—H5121.3C10—C11—S1113.1 (2)
C4—C5—C6117.4 (2)C10—C11—H11123.4
Br1—C4—C3—N2176.7 (2)C6—C2—N2—C33.8 (4)
S2—C12—C7—N310.8 (3)C6—C5—C4—Br1179.77 (16)
S2—C12—C7—C1170.70 (17)C6—C5—C4—C31.6 (3)
S2—C12—C13—C141.8 (3)C13—C12—C7—N3161.0 (2)
S1—C8—C9—C101.7 (3)C13—C12—C7—C117.6 (4)
N3—C7—C1—N116.0 (3)C13—C14—C15—S20.8 (3)
N3—C7—C1—C8159.4 (2)N1—C2—C6—N313.7 (3)
N3—C6—C5—C4173.5 (2)N1—C2—C6—C5168.7 (2)
C12—S2—C15—C141.6 (2)N1—C2—N2—C3172.1 (2)
C12—C7—C1—N1162.4 (2)N1—C1—C8—S125.5 (3)
C12—C7—C1—C822.2 (3)N1—C1—C8—C9143.6 (2)
C12—C13—C14—C150.7 (3)N2—C2—C6—N3170.5 (2)
C7—N3—C6—C25.8 (3)N2—C2—C6—C57.0 (4)
C7—N3—C6—C5176.7 (2)N2—C2—N1—C1177.9 (2)
C7—C12—C13—C14174.0 (2)C1—C8—C9—C10171.4 (2)
C7—C1—C8—S1158.88 (17)C5—C4—C3—N25.1 (4)
C7—C1—C8—C932.0 (4)C8—S1—C11—C101.2 (3)
C2—C6—C5—C44.0 (3)C8—C9—C10—C110.9 (4)
C2—N1—C1—C78.1 (3)C15—S2—C12—C7175.40 (18)
C2—N1—C1—C8167.7 (2)C15—S2—C12—C131.91 (19)
C2—N2—C3—C42.3 (4)C9—C10—C11—S10.3 (4)
C6—N3—C7—C12170.23 (19)C11—S1—C8—C1172.6 (2)
C6—N3—C7—C18.4 (3)C11—S1—C8—C91.7 (2)
C6—C2—N1—C16.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···Br1i0.933.013.836 (1)150
C5—H5···Br1ii0.933.053.851 (1)145
C15—H15···N1iii0.932.653.572 (1)175
C11—H11···C14iv0.932.783.637 (1)155
Symmetry codes: (i) x+2, y, z+1; (ii) x+1, y, z; (iii) x1, y, z1; (iv) x+1, y1/2, z+1/2.
 

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