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The pyrrolidine ring in the title compound, C35H34N4O2S, adopts an envelope conformation, with the N atom deviating by 0.586 (1) Å from the plane of the other atoms. The mol­ecule is stabilized by weak C—H...O inter­actions and the crystal packing is stabilized by N—H...N inter­molecular inter­actions, generating a dimer with an R22(16) motif.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048021/cf2064sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048021/cf2064Isup2.hkl
Contains datablock I

CCDC reference: 629466

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.041
  • wR factor = 0.107
  • Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.90 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C24 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C35 PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 32.00 A   3
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

1-N-methyl-spiro[2.3']oxindole-spiro[3.2'']-5''-phenyl- 5'',6'',7'',8'',9'',10''-hexahydrocyclohepteno[1,2-d]thiazolo[3,2-a]pyrimidin- 3''-one-4-(p-methyl)phenyl-pyrrolidine top
Crystal data top
C35H34N4O2SZ = 2
Mr = 574.72F(000) = 608
Triclinic, P1Dx = 1.262 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.3427 (8) ÅCell parameters from 2520 reflections
b = 12.0148 (9) Åθ = 1.7–25.0°
c = 13.0102 (10) ŵ = 0.15 mm1
α = 95.604 (1)°T = 293 K
β = 110.887 (1)°Block, colourless
γ = 109.567 (1)°0.24 × 0.21 × 0.20 mm
V = 1512.67 (19) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4625 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Graphite monochromatorθmax = 25.0°, θmin = 1.7°
ω scansh = 1313
14702 measured reflectionsk = 1414
5317 independent reflectionsl = 1515
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0515P)2 + 0.4411P]
where P = (Fo2 + 2Fc2)/3
5317 reflections(Δ/σ)max < 0.001
379 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.17 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.

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
xyzUiso*/Ueq
C10.22963 (16)0.11826 (14)0.19966 (13)0.0369 (4)
C20.22018 (16)0.00933 (14)0.22648 (12)0.0359 (4)
C30.06173 (17)0.01920 (15)0.16267 (13)0.0407 (4)
H30.05170.01610.09680.049*
C40.00561 (17)0.15731 (16)0.11584 (15)0.0467 (4)
H4A0.03220.19810.16970.056*
H4B0.08610.18080.04490.056*
C50.0688 (2)0.31561 (17)0.06367 (19)0.0642 (6)
H5A0.14460.32640.05390.096*
H5B0.01170.35120.00680.096*
H5C0.05170.35460.12090.096*
C60.23923 (18)0.17501 (15)0.30427 (14)0.0417 (4)
C70.42526 (17)0.16556 (15)0.26896 (14)0.0440 (4)
C80.5403 (2)0.18412 (18)0.27291 (18)0.0587 (5)
H80.58810.21220.33140.070*
C90.5819 (2)0.1595 (2)0.1869 (2)0.0636 (6)
H90.65920.17110.18760.076*
C100.5109 (2)0.11813 (19)0.10007 (19)0.0614 (5)
H100.54030.10290.04270.074*
C110.3957 (2)0.09897 (17)0.09741 (16)0.0498 (4)
H110.34710.07210.03830.060*
C120.35462 (17)0.12042 (14)0.18389 (14)0.0397 (4)
C130.30013 (17)0.10003 (14)0.17572 (13)0.0362 (4)
C140.50024 (16)0.29403 (14)0.22450 (13)0.0378 (4)
H140.53200.25680.17510.045*
C150.42212 (16)0.36412 (14)0.15988 (14)0.0386 (4)
C160.4012 (2)0.36248 (17)0.04880 (16)0.0518 (5)
H160.43160.31530.01200.062*
C170.3352 (2)0.4306 (2)0.00873 (19)0.0674 (6)
H170.32130.42860.08390.081*
C180.2906 (2)0.5001 (2)0.0442 (2)0.0680 (6)
H180.24780.54680.00570.082*
C190.3087 (2)0.5014 (2)0.1541 (2)0.0688 (6)
H190.27680.54790.19000.083*
C200.3746 (2)0.43357 (18)0.21218 (17)0.0562 (5)
H200.38680.43490.28690.067*
C210.62483 (17)0.37864 (15)0.33012 (15)0.0428 (4)
C220.7364 (2)0.47000 (19)0.30781 (18)0.0600 (5)
H22A0.71300.45040.22700.072*
H22B0.82160.46030.34640.072*
C230.7617 (3)0.6024 (2)0.3445 (2)0.0835 (7)
H23A0.67400.61010.31770.100*
H23B0.81530.65000.30840.100*
C240.8365 (3)0.6561 (2)0.4725 (2)0.1037 (10)
H24A0.92630.65260.49790.124*
H24B0.85100.74150.48730.124*
C250.7665 (3)0.5964 (2)0.5431 (2)0.0911 (8)
H25A0.67660.59970.51770.109*
H25B0.81920.64380.62120.109*
C260.7479 (2)0.46397 (19)0.54022 (17)0.0659 (6)
H26A0.83290.45650.54740.079*
H26B0.73090.44320.60520.079*
C270.63207 (17)0.37386 (15)0.43374 (15)0.0445 (4)
C280.43195 (16)0.20146 (14)0.36844 (13)0.0357 (4)
C290.00676 (17)0.02952 (15)0.22505 (14)0.0422 (4)
C300.0607 (2)0.11323 (17)0.18644 (16)0.0530 (5)
H300.04750.14340.12650.064*
C310.1342 (2)0.15230 (19)0.23646 (18)0.0602 (5)
H310.16930.20840.20920.072*
C320.15624 (19)0.11018 (19)0.32534 (16)0.0558 (5)
C330.10020 (19)0.02825 (19)0.36504 (16)0.0528 (5)
H330.11200.00040.42610.063*
C340.02740 (18)0.01153 (17)0.31587 (15)0.0483 (4)
H340.00850.06690.34400.058*
C350.2428 (3)0.1476 (2)0.3751 (2)0.0799 (7)
H35A0.24650.10920.43590.120*
H35B0.33420.12270.31740.120*
H35C0.20280.23450.40380.120*
N10.10197 (14)0.18586 (12)0.09858 (11)0.0428 (3)
N20.35672 (15)0.19467 (13)0.33936 (12)0.0485 (4)
H20.38570.22190.39810.058*
N30.41205 (13)0.19650 (12)0.25685 (10)0.0364 (3)
N40.53072 (14)0.28254 (12)0.45488 (11)0.0413 (3)
O10.15454 (14)0.19913 (12)0.34402 (11)0.0562 (3)
O20.26921 (13)0.08940 (10)0.07538 (9)0.0470 (3)
S10.30170 (4)0.08071 (4)0.37902 (3)0.04215 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0382 (9)0.0352 (8)0.0331 (8)0.0135 (7)0.0105 (7)0.0106 (7)
C20.0397 (9)0.0363 (8)0.0271 (8)0.0150 (7)0.0089 (7)0.0085 (6)
C30.0401 (9)0.0443 (9)0.0332 (8)0.0185 (8)0.0084 (7)0.0108 (7)
C40.0373 (9)0.0467 (10)0.0446 (10)0.0152 (8)0.0075 (8)0.0055 (8)
C50.0554 (12)0.0448 (11)0.0706 (14)0.0158 (9)0.0113 (10)0.0054 (10)
C60.0478 (10)0.0343 (9)0.0383 (9)0.0143 (8)0.0141 (8)0.0109 (7)
C70.0412 (9)0.0391 (9)0.0417 (9)0.0151 (8)0.0080 (8)0.0064 (7)
C80.0469 (11)0.0581 (12)0.0593 (12)0.0269 (10)0.0060 (9)0.0045 (10)
C90.0455 (11)0.0625 (13)0.0746 (15)0.0203 (10)0.0221 (11)0.0027 (11)
C100.0622 (13)0.0572 (12)0.0683 (13)0.0194 (10)0.0369 (11)0.0075 (10)
C110.0572 (11)0.0475 (10)0.0469 (10)0.0208 (9)0.0237 (9)0.0127 (8)
C120.0390 (9)0.0351 (8)0.0389 (9)0.0133 (7)0.0113 (7)0.0071 (7)
C130.0432 (9)0.0341 (8)0.0302 (8)0.0181 (7)0.0110 (7)0.0097 (6)
C140.0416 (9)0.0368 (8)0.0363 (8)0.0158 (7)0.0168 (7)0.0111 (7)
C150.0390 (9)0.0328 (8)0.0393 (9)0.0105 (7)0.0140 (7)0.0107 (7)
C160.0625 (12)0.0520 (11)0.0445 (10)0.0234 (9)0.0236 (9)0.0199 (8)
C170.0744 (14)0.0720 (14)0.0553 (12)0.0286 (12)0.0214 (11)0.0375 (11)
C180.0610 (13)0.0583 (13)0.0828 (16)0.0288 (11)0.0181 (12)0.0360 (12)
C190.0693 (14)0.0632 (13)0.0812 (16)0.0406 (12)0.0258 (12)0.0175 (12)
C200.0648 (12)0.0611 (12)0.0497 (11)0.0344 (10)0.0222 (10)0.0152 (9)
C210.0409 (9)0.0388 (9)0.0439 (10)0.0149 (8)0.0127 (8)0.0131 (7)
C220.0487 (11)0.0598 (12)0.0585 (12)0.0097 (9)0.0179 (9)0.0194 (10)
C230.0853 (17)0.0525 (13)0.0822 (17)0.0012 (12)0.0248 (14)0.0207 (12)
C240.116 (2)0.0521 (14)0.0875 (19)0.0085 (14)0.0241 (17)0.0062 (13)
C250.105 (2)0.0524 (13)0.0673 (15)0.0023 (13)0.0194 (14)0.0073 (11)
C260.0595 (12)0.0579 (12)0.0457 (11)0.0039 (10)0.0045 (10)0.0044 (9)
C270.0422 (9)0.0388 (9)0.0416 (9)0.0136 (8)0.0080 (8)0.0089 (7)
C280.0411 (9)0.0365 (8)0.0304 (8)0.0194 (7)0.0114 (7)0.0107 (7)
C290.0382 (9)0.0442 (9)0.0376 (9)0.0177 (8)0.0080 (7)0.0075 (7)
C300.0608 (12)0.0509 (11)0.0461 (10)0.0288 (9)0.0146 (9)0.0132 (8)
C310.0652 (13)0.0564 (12)0.0581 (12)0.0386 (11)0.0128 (10)0.0080 (10)
C320.0474 (11)0.0614 (12)0.0473 (11)0.0256 (10)0.0081 (9)0.0045 (9)
C330.0467 (10)0.0661 (12)0.0422 (10)0.0246 (9)0.0136 (8)0.0103 (9)
C340.0427 (10)0.0549 (11)0.0475 (10)0.0254 (9)0.0126 (8)0.0154 (8)
C350.0779 (16)0.0948 (18)0.0713 (15)0.0512 (15)0.0257 (13)0.0012 (13)
N10.0396 (8)0.0391 (8)0.0388 (8)0.0151 (6)0.0067 (6)0.0031 (6)
N20.0538 (9)0.0518 (9)0.0404 (8)0.0262 (7)0.0129 (7)0.0213 (7)
N30.0414 (7)0.0339 (7)0.0293 (7)0.0131 (6)0.0111 (6)0.0092 (5)
N40.0445 (8)0.0391 (8)0.0314 (7)0.0140 (7)0.0087 (6)0.0075 (6)
O10.0625 (8)0.0599 (8)0.0565 (8)0.0240 (7)0.0329 (7)0.0278 (7)
O20.0610 (8)0.0412 (7)0.0287 (6)0.0151 (6)0.0121 (5)0.0106 (5)
S10.0461 (3)0.0432 (2)0.0284 (2)0.01068 (19)0.01238 (18)0.00934 (17)
Geometric parameters (Å, º) top
C1—N11.460 (2)C18—C191.369 (3)
C1—C121.511 (2)C18—H180.930
C1—C61.567 (2)C19—C201.385 (3)
C1—C21.586 (2)C19—H190.930
C2—C131.533 (2)C20—H200.930
C2—C31.583 (2)C21—C271.329 (2)
C2—S11.832 (2)C21—C221.512 (2)
C3—C291.505 (2)C22—C231.513 (3)
C3—C41.526 (2)C22—H22A0.970
C3—H30.980C22—H22B0.970
C4—N11.455 (2)C23—C241.524 (4)
C4—H4A0.970C23—H23A0.970
C4—H4B0.970C23—H23B0.970
C5—N11.458 (2)C24—C251.502 (4)
C5—H5A0.960C24—H24A0.970
C5—H5B0.960C24—H24B0.970
C5—H5C0.960C25—C261.529 (3)
C6—O11.213 (2)C25—H25A0.970
C6—N21.356 (2)C25—H25B0.970
C7—C81.380 (3)C26—C271.508 (2)
C7—C121.392 (2)C26—H26A0.970
C7—N21.398 (2)C26—H26B0.970
C8—C91.382 (3)C27—N41.428 (2)
C8—H80.930C28—N41.275 (2)
C9—C101.379 (3)C28—N31.379 (2)
C9—H90.930C28—S11.748 (2)
C10—C111.390 (3)C29—C341.389 (2)
C10—H100.930C29—C301.389 (2)
C11—C121.378 (2)C30—C311.388 (3)
C11—H110.930C30—H300.930
C13—O21.206 (2)C31—C321.375 (3)
C13—N31.374 (2)C31—H310.930
C14—N31.471 (2)C32—C331.387 (3)
C14—C211.516 (2)C32—C351.509 (3)
C14—C151.519 (2)C33—C341.379 (3)
C14—H140.980C33—H330.930
C15—C161.375 (2)C34—H340.930
C15—C201.379 (3)C35—H35A0.960
C16—C171.386 (3)C35—H35B0.960
C16—H160.930C35—H35C0.960
C17—C181.359 (3)N2—H20.860
C17—H170.930
N1—C1—C12112.65 (13)C15—C20—H20119.8
N1—C1—C6113.74 (13)C19—C20—H20119.8
C12—C1—C6101.52 (13)C27—C21—C22123.27 (16)
N1—C1—C2101.97 (12)C27—C21—C14121.86 (15)
C12—C1—C2118.53 (13)C22—C21—C14114.84 (15)
C6—C1—C2108.89 (12)C21—C22—C23115.90 (19)
C13—C2—C3108.84 (12)C21—C22—H22A108.3
C13—C2—C1110.21 (12)C23—C22—H22A108.3
C3—C2—C1104.20 (12)C21—C22—H22B108.3
C13—C2—S1104.75 (10)C23—C22—H22B108.3
C3—C2—S1116.63 (11)H22A—C22—H22B107.4
C1—C2—S1112.21 (10)C22—C23—C24114.3 (2)
C29—C3—C4114.03 (14)C22—C23—H23A108.7
C29—C3—C2118.85 (13)C24—C23—H23A108.7
C4—C3—C2104.13 (13)C22—C23—H23B108.7
C29—C3—H3106.3C24—C23—H23B108.7
C4—C3—H3106.3H23A—C23—H23B107.6
C2—C3—H3106.3C25—C24—C23116.5 (2)
N1—C4—C3103.31 (13)C25—C24—H24A108.2
N1—C4—H4A111.1C23—C24—H24A108.2
C3—C4—H4A111.1C25—C24—H24B108.2
N1—C4—H4B111.1C23—C24—H24B108.2
C3—C4—H4B111.1H24A—C24—H24B107.3
H4A—C4—H4B109.1C24—C25—C26115.8 (2)
N1—C5—H5A109.5C24—C25—H25A108.3
N1—C5—H5B109.5C26—C25—H25A108.3
H5A—C5—H5B109.5C24—C25—H25B108.3
N1—C5—H5C109.5C26—C25—H25B108.3
H5A—C5—H5C109.5H25A—C25—H25B107.4
H5B—C5—H5C109.5C27—C26—C25113.89 (18)
O1—C6—N2126.88 (16)C27—C26—H26A108.8
O1—C6—C1125.63 (15)C25—C26—H26A108.8
N2—C6—C1107.48 (14)C27—C26—H26B108.8
C8—C7—C12121.99 (18)C25—C26—H26B108.8
C8—C7—N2127.89 (17)H26A—C26—H26B107.7
C12—C7—N2109.97 (15)C21—C27—N4123.14 (15)
C7—C8—C9117.61 (19)C21—C27—C26123.34 (17)
C7—C8—H8121.2N4—C27—C26113.52 (16)
C9—C8—H8121.2N4—C28—N3125.96 (15)
C10—C9—C8121.24 (19)N4—C28—S1122.70 (12)
C10—C9—H9119.4N3—C28—S1111.35 (11)
C8—C9—H9119.4C34—C29—C30117.57 (16)
C9—C10—C11120.6 (2)C34—C29—C3122.93 (15)
C9—C10—H10119.7C30—C29—C3119.35 (16)
C11—C10—H10119.7C31—C30—C29120.68 (19)
C12—C11—C10118.89 (18)C31—C30—H30119.7
C12—C11—H11120.6C29—C30—H30119.7
C10—C11—H11120.6C32—C31—C30121.68 (18)
C11—C12—C7119.57 (16)C32—C31—H31119.2
C11—C12—C1131.17 (15)C30—C31—H31119.2
C7—C12—C1108.82 (14)C31—C32—C33117.54 (18)
O2—C13—N3122.76 (15)C31—C32—C35121.46 (19)
O2—C13—C2124.29 (14)C33—C32—C35121.0 (2)
N3—C13—C2112.95 (13)C34—C33—C32121.33 (19)
N3—C14—C21109.32 (13)C34—C33—H33119.3
N3—C14—C15111.46 (13)C32—C33—H33119.3
C21—C14—C15110.86 (13)C33—C34—C29121.19 (17)
N3—C14—H14108.4C33—C34—H34119.4
C21—C14—H14108.4C29—C34—H34119.4
C15—C14—H14108.4C32—C35—H35A109.5
C16—C15—C20118.67 (16)C32—C35—H35B109.5
C16—C15—C14120.46 (15)H35A—C35—H35B109.5
C20—C15—C14120.84 (15)C32—C35—H35C109.5
C15—C16—C17120.52 (19)H35A—C35—H35C109.5
C15—C16—H16119.7H35B—C35—H35C109.5
C17—C16—H16119.7C4—N1—C5114.8 (2)
C18—C17—C16120.3 (2)C4—N1—C1107.3 (1)
C18—C17—H17119.8C5—N1—C1115.1 (1)
C16—C17—H17119.8C6—N2—C7112.1 (1)
C17—C18—C19119.90 (19)C6—N2—H2124.0
C17—C18—H18120.1C7—N2—H2124.0
C19—C18—H18120.1C13—N3—C28117.1 (1)
C18—C19—C20120.1 (2)C13—N3—C14120.9 (1)
C18—C19—H19119.9C28—N3—C14121.9 (1)
C20—C19—H19119.9C28—N4—C27116.6 (1)
C15—C20—C19120.46 (19)C28—S1—C293.47 (7)
N1—C1—C2—C1396.21 (14)C15—C14—C21—C2267.00 (19)
C12—C1—C2—C1328.07 (18)C27—C21—C22—C2364.1 (3)
C6—C1—C2—C13143.30 (13)C14—C21—C22—C23114.1 (2)
N1—C1—C2—C320.41 (15)C21—C22—C23—C2473.9 (3)
C12—C1—C2—C3144.69 (14)C22—C23—C24—C2560.2 (4)
C6—C1—C2—C3100.08 (14)C23—C24—C25—C2664.0 (4)
N1—C1—C2—S1147.47 (11)C24—C25—C26—C2777.1 (3)
C12—C1—C2—S188.25 (15)C22—C21—C27—N4175.82 (16)
C6—C1—C2—S126.98 (16)C14—C21—C27—N46.1 (3)
C13—C2—C3—C29109.25 (16)C22—C21—C27—C264.1 (3)
C1—C2—C3—C29133.18 (15)C14—C21—C27—C26174.01 (17)
S1—C2—C3—C298.91 (19)C25—C26—C27—C2157.8 (3)
C13—C2—C3—C4122.57 (14)C25—C26—C27—N4122.3 (2)
C1—C2—C3—C45.00 (16)C4—C3—C29—C3455.4 (2)
S1—C2—C3—C4119.27 (13)C2—C3—C29—C3468.1 (2)
C29—C3—C4—N1159.97 (13)C4—C3—C29—C30120.08 (18)
C2—C3—C4—N128.89 (16)C2—C3—C29—C30116.50 (18)
N1—C1—C6—O153.7 (2)C34—C29—C30—C310.9 (3)
C12—C1—C6—O1174.96 (16)C3—C29—C30—C31174.76 (17)
C2—C1—C6—O159.2 (2)C29—C30—C31—C320.0 (3)
N1—C1—C6—N2124.73 (15)C30—C31—C32—C331.1 (3)
C12—C1—C6—N23.47 (16)C30—C31—C32—C35176.54 (19)
C2—C1—C6—N2122.33 (14)C31—C32—C33—C341.3 (3)
C12—C7—C8—C91.8 (3)C35—C32—C33—C34176.37 (19)
N2—C7—C8—C9173.39 (18)C32—C33—C34—C290.4 (3)
C7—C8—C9—C100.1 (3)C30—C29—C34—C330.8 (3)
C8—C9—C10—C110.6 (3)C3—C29—C34—C33174.77 (16)
C9—C10—C11—C120.9 (3)C3—C4—N1—C5174.42 (15)
C10—C11—C12—C72.8 (3)C3—C4—N1—C145.10 (16)
C10—C11—C12—C1174.23 (17)C12—C1—N1—C4168.94 (13)
C8—C7—C12—C113.3 (3)C6—C1—N1—C476.24 (16)
N2—C7—C12—C11172.67 (15)C2—C1—N1—C440.81 (16)
C8—C7—C12—C1176.53 (16)C12—C1—N1—C561.92 (19)
N2—C7—C12—C10.56 (19)C6—C1—N1—C552.9 (2)
N1—C1—C12—C1147.8 (2)C2—C1—N1—C5169.95 (15)
C6—C1—C12—C11169.79 (18)O1—C6—N2—C7174.97 (17)
C2—C1—C12—C1171.1 (2)C1—C6—N2—C73.43 (19)
N1—C1—C12—C7124.39 (15)C8—C7—N2—C6173.75 (17)
C6—C1—C12—C72.38 (17)C12—C7—N2—C61.9 (2)
C2—C1—C12—C7116.76 (15)O2—C13—N3—C28176.57 (15)
C3—C2—C13—O248.3 (2)C2—C13—N3—C283.22 (19)
C1—C2—C13—O265.42 (19)O2—C13—N3—C140.7 (2)
S1—C2—C13—O2173.69 (14)C2—C13—N3—C14179.05 (13)
C3—C2—C13—N3131.51 (14)N4—C28—N3—C13178.81 (15)
C1—C2—C13—N3114.80 (14)S1—C28—N3—C131.61 (17)
S1—C2—C13—N36.09 (15)N4—C28—N3—C145.4 (2)
N3—C14—C15—C16116.21 (17)S1—C28—N3—C14174.17 (11)
C21—C14—C15—C16121.76 (18)C21—C14—N3—C13172.69 (13)
N3—C14—C15—C2065.8 (2)C15—C14—N3—C1364.40 (18)
C21—C14—C15—C2056.2 (2)C21—C14—N3—C2811.7 (2)
C20—C15—C16—C170.8 (3)C15—C14—N3—C28111.23 (16)
C14—C15—C16—C17177.20 (17)N3—C28—N4—C272.3 (2)
C15—C16—C17—C180.2 (3)S1—C28—N4—C27178.19 (11)
C16—C17—C18—C191.2 (3)C21—C27—N4—C281.8 (2)
C17—C18—C19—C201.1 (3)C26—C27—N4—C28178.07 (16)
C16—C15—C20—C190.8 (3)N4—C28—S1—C2175.81 (14)
C14—C15—C20—C19177.16 (18)N3—C28—S1—C24.60 (12)
C18—C19—C20—C150.1 (3)C13—C2—S1—C285.85 (11)
N3—C14—C21—C2712.0 (2)C3—C2—S1—C28126.22 (12)
C15—C14—C21—C27111.22 (18)C1—C2—S1—C28113.71 (12)
N3—C14—C21—C22169.73 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O20.982.452.944 (2)111
C4—H4A···O10.972.503.070 (2)118
C11—H11···O20.932.463.045 (3)121
N2—H2···N4i0.862.132.988 (2)177
Symmetry code: (i) x+1, y, z+1.
 

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