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The title compound, C20H17N5, has two mol­ecules in the asymmetric unit with comparable conformations. In each mol­ecule, the isoindoline group and one methyl­pyridyl ring are coplanar, while the other methyl­pyridyl rings form angles with respect to these planes of 43.2 (2) and 37.6 (2)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807009075/bi2163sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807009075/bi2163Isup2.hkl
Contains datablock I

CCDC reference: 642915

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.050
  • wR factor = 0.142
  • Data-to-parameter ratio = 13.1

checkCIF/PLATON results

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Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ... 3399.00 Ang-3 PLAT230_ALERT_2_C Hirshfeld Test Diff for C20 - C22 .. 5.29 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

1,3-Bis(6-methyl-2-pyridylimino)-2,3-dihydro-1H-isoindoline top
Crystal data top
C20H17N5F(000) = 1376
Mr = 327.39Dx = 1.279 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1958 reflections
a = 17.148 (6) Åθ = 2.2–22.9°
b = 18.399 (6) ŵ = 0.08 mm1
c = 10.847 (4) ÅT = 298 K
β = 96.606 (5)°Block, yellow
V = 3399 (2) Å30.30 × 0.20 × 0.20 mm
Z = 8
Data collection top
Siemens SMART CCD area-detector
diffractometer
5977 independent reflections
Radiation source: fine-focus sealed tube3272 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
ω scansθmax = 25.0°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2019
Tmin = 0.977, Tmax = 0.984k = 2021
13510 measured reflectionsl = 128
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0537P)2 + 0.0985P]
where P = (Fo2 + 2Fc2)/3
5977 reflections(Δ/σ)max < 0.001
455 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.13 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
N10.37859 (12)0.50530 (11)0.33298 (19)0.0627 (6)
N20.39479 (12)0.39715 (11)0.21793 (19)0.0622 (5)
N30.25937 (11)0.41247 (10)0.26035 (17)0.0551 (5)
H30.26320.45290.30030.066*
N40.11944 (12)0.39085 (11)0.25376 (19)0.0629 (6)
N50.15077 (12)0.47215 (11)0.4213 (2)0.0652 (6)
N60.36719 (11)0.68562 (11)0.13647 (18)0.0608 (5)
N70.37685 (11)0.57661 (11)0.01994 (18)0.0617 (5)
N80.24384 (10)0.59721 (9)0.06887 (17)0.0532 (5)
H80.25070.63600.11310.064*
N90.10225 (11)0.58579 (9)0.05332 (18)0.0553 (5)
N100.14021 (12)0.66993 (11)0.2158 (2)0.0631 (6)
C10.35631 (18)0.61330 (15)0.4474 (3)0.1009 (11)
H1A0.30770.61740.39430.151*
H1B0.37930.66060.46090.151*
H1C0.34660.59270.52550.151*
C20.41107 (17)0.56563 (14)0.3876 (3)0.0695 (7)
C30.48912 (18)0.58199 (15)0.3872 (3)0.0787 (8)
H3A0.51030.62320.42790.094*
C40.53552 (17)0.53704 (17)0.3263 (3)0.0830 (9)
H40.58830.54790.32420.100*
C50.50354 (16)0.47602 (15)0.2685 (3)0.0741 (8)
H50.53400.44510.22600.089*
C60.42457 (15)0.46127 (14)0.2746 (2)0.0598 (6)
C80.32227 (15)0.37816 (12)0.2152 (2)0.0553 (6)
C90.29015 (15)0.31092 (12)0.1570 (2)0.0588 (6)
C100.32674 (17)0.25569 (14)0.0975 (2)0.0698 (7)
H100.38040.25690.09130.084*
C110.2807 (2)0.19917 (15)0.0481 (2)0.0818 (9)
H110.30370.16180.00730.098*
C120.2010 (2)0.19675 (14)0.0577 (3)0.0815 (9)
H120.17130.15800.02300.098*
C130.16461 (17)0.25162 (14)0.1186 (2)0.0708 (7)
H130.11120.24990.12610.085*
C140.21032 (15)0.30855 (12)0.1674 (2)0.0579 (6)
C150.18951 (15)0.37438 (12)0.2340 (2)0.0551 (6)
C160.10259 (15)0.45381 (13)0.3196 (3)0.0607 (7)
C170.03408 (16)0.49088 (14)0.2815 (3)0.0708 (8)
H170.00130.47570.21200.085*
C180.01540 (18)0.55031 (16)0.3475 (3)0.0833 (9)
H180.02940.57730.32170.100*
C190.06319 (19)0.56985 (15)0.4521 (3)0.0807 (9)
H190.05090.60990.49830.097*
C200.13008 (17)0.52942 (15)0.4884 (3)0.0702 (8)
C220.18238 (19)0.54475 (17)0.6070 (3)0.0987 (10)
H22A0.22690.51280.61300.148*
H22B0.15350.53690.67660.148*
H22C0.20000.59430.60700.148*
C230.35228 (18)0.79534 (14)0.2556 (3)0.0949 (10)
H23A0.30040.79670.21160.142*
H23B0.37460.84320.25810.142*
H23C0.34960.77840.33870.142*
C240.40270 (16)0.74472 (14)0.1903 (2)0.0692 (7)
C250.48183 (18)0.75779 (16)0.1870 (3)0.0819 (8)
H250.50570.79790.22760.098*
C260.52462 (17)0.71116 (19)0.1234 (3)0.0877 (9)
H260.57760.72010.11880.105*
C270.48942 (15)0.65107 (17)0.0664 (3)0.0778 (8)
H270.51780.61910.02230.093*
C280.41033 (14)0.63908 (14)0.0761 (2)0.0605 (6)
C300.30400 (14)0.56040 (12)0.0195 (2)0.0527 (6)
C310.26709 (13)0.49506 (12)0.0399 (2)0.0523 (6)
C320.30040 (16)0.43834 (13)0.0992 (2)0.0651 (7)
H320.35370.43740.10800.078*
C330.25047 (17)0.38307 (14)0.1449 (2)0.0715 (8)
H330.27080.34390.18510.086*
C340.17113 (17)0.38462 (13)0.1324 (2)0.0695 (7)
H340.13930.34650.16390.083*
C350.13833 (15)0.44170 (12)0.0739 (2)0.0605 (7)
H350.08500.44280.06550.073*
C360.18777 (14)0.49700 (11)0.0285 (2)0.0495 (6)
C370.17135 (14)0.56399 (11)0.0384 (2)0.0497 (6)
C380.08932 (14)0.64982 (13)0.1186 (2)0.0551 (6)
C390.02035 (14)0.68735 (13)0.0828 (2)0.0634 (7)
H390.01450.67120.01650.076*
C400.00440 (17)0.74885 (15)0.1471 (3)0.0754 (8)
H400.04040.77610.12270.090*
C410.05539 (17)0.76955 (14)0.2476 (3)0.0738 (8)
H410.04520.81080.29270.089*
C420.12220 (15)0.72863 (14)0.2815 (3)0.0683 (7)
C440.17606 (18)0.74563 (17)0.3960 (3)0.1018 (11)
H44A0.22060.71370.40130.153*
H44B0.14870.73910.46760.153*
H44C0.19350.79510.39270.153*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0661 (14)0.0571 (12)0.0659 (14)0.0025 (11)0.0117 (11)0.0009 (11)
N20.0592 (14)0.0609 (13)0.0668 (14)0.0058 (11)0.0077 (11)0.0013 (11)
N30.0587 (13)0.0495 (11)0.0578 (13)0.0019 (10)0.0092 (10)0.0012 (10)
N40.0607 (14)0.0624 (13)0.0658 (14)0.0029 (11)0.0086 (11)0.0073 (11)
N50.0657 (15)0.0655 (14)0.0660 (15)0.0009 (11)0.0147 (12)0.0052 (12)
N60.0579 (13)0.0655 (13)0.0596 (13)0.0053 (11)0.0100 (10)0.0012 (11)
N70.0487 (13)0.0762 (14)0.0601 (13)0.0031 (11)0.0066 (10)0.0045 (11)
N80.0490 (12)0.0505 (11)0.0616 (13)0.0002 (9)0.0125 (9)0.0088 (10)
N90.0516 (13)0.0520 (11)0.0649 (14)0.0009 (10)0.0177 (10)0.0022 (10)
N100.0577 (14)0.0641 (13)0.0709 (15)0.0001 (10)0.0224 (12)0.0141 (12)
C10.111 (3)0.0763 (19)0.120 (3)0.0068 (18)0.034 (2)0.0250 (19)
C20.083 (2)0.0597 (16)0.0675 (18)0.0029 (15)0.0146 (15)0.0025 (15)
C30.089 (2)0.0701 (18)0.077 (2)0.0181 (17)0.0090 (17)0.0038 (16)
C40.067 (2)0.087 (2)0.095 (2)0.0103 (17)0.0098 (17)0.0101 (19)
C50.0647 (19)0.0756 (19)0.083 (2)0.0034 (15)0.0121 (15)0.0027 (16)
C60.0576 (17)0.0607 (15)0.0605 (17)0.0055 (13)0.0041 (13)0.0062 (14)
C80.0651 (17)0.0514 (14)0.0491 (15)0.0067 (13)0.0052 (12)0.0048 (12)
C90.0733 (18)0.0556 (15)0.0471 (15)0.0050 (13)0.0043 (13)0.0054 (13)
C100.084 (2)0.0656 (16)0.0604 (18)0.0096 (15)0.0085 (15)0.0031 (15)
C110.118 (3)0.0689 (19)0.0572 (18)0.0135 (18)0.0048 (18)0.0092 (15)
C120.117 (3)0.0604 (17)0.0619 (19)0.0095 (18)0.0127 (18)0.0020 (15)
C130.083 (2)0.0611 (16)0.0659 (18)0.0066 (15)0.0032 (15)0.0072 (15)
C140.0756 (18)0.0511 (15)0.0458 (15)0.0000 (13)0.0018 (13)0.0062 (12)
C150.0615 (17)0.0534 (14)0.0495 (15)0.0034 (13)0.0026 (12)0.0098 (12)
C160.0602 (17)0.0579 (16)0.0668 (19)0.0022 (14)0.0190 (14)0.0161 (15)
C170.0656 (18)0.0762 (18)0.0728 (19)0.0049 (15)0.0170 (15)0.0187 (16)
C180.081 (2)0.080 (2)0.093 (3)0.0165 (17)0.028 (2)0.0206 (19)
C190.092 (2)0.0656 (18)0.091 (2)0.0093 (17)0.0402 (19)0.0082 (18)
C200.078 (2)0.0701 (18)0.0670 (19)0.0059 (15)0.0252 (16)0.0057 (16)
C220.111 (3)0.104 (2)0.085 (2)0.009 (2)0.025 (2)0.008 (2)
C230.112 (3)0.0701 (18)0.105 (2)0.0201 (17)0.023 (2)0.0165 (18)
C240.074 (2)0.0676 (17)0.0651 (18)0.0182 (15)0.0044 (15)0.0060 (15)
C250.076 (2)0.084 (2)0.083 (2)0.0270 (17)0.0016 (17)0.0094 (18)
C260.0547 (18)0.119 (3)0.088 (2)0.0240 (19)0.0036 (16)0.016 (2)
C270.0510 (18)0.111 (2)0.0717 (19)0.0017 (16)0.0079 (14)0.0048 (18)
C280.0481 (16)0.0789 (17)0.0543 (16)0.0012 (13)0.0051 (12)0.0062 (14)
C300.0517 (16)0.0594 (14)0.0476 (15)0.0073 (12)0.0084 (12)0.0031 (12)
C310.0582 (16)0.0536 (14)0.0451 (14)0.0070 (12)0.0060 (11)0.0003 (12)
C320.0677 (17)0.0690 (17)0.0586 (16)0.0178 (14)0.0075 (13)0.0019 (14)
C330.092 (2)0.0619 (17)0.0600 (18)0.0171 (16)0.0072 (15)0.0110 (14)
C340.087 (2)0.0560 (15)0.0648 (18)0.0023 (14)0.0048 (15)0.0075 (14)
C350.0693 (17)0.0566 (15)0.0554 (16)0.0023 (13)0.0072 (13)0.0013 (13)
C360.0593 (16)0.0474 (13)0.0423 (13)0.0028 (12)0.0077 (11)0.0025 (11)
C370.0539 (15)0.0491 (13)0.0474 (14)0.0000 (12)0.0109 (11)0.0054 (11)
C380.0498 (15)0.0558 (15)0.0640 (17)0.0021 (12)0.0252 (13)0.0022 (13)
C390.0546 (16)0.0675 (16)0.0721 (18)0.0041 (13)0.0242 (13)0.0054 (14)
C400.069 (2)0.0733 (19)0.089 (2)0.0183 (15)0.0294 (17)0.0091 (17)
C410.078 (2)0.0606 (16)0.089 (2)0.0081 (15)0.0376 (18)0.0078 (16)
C420.0574 (17)0.0720 (17)0.080 (2)0.0023 (14)0.0288 (15)0.0166 (16)
C440.083 (2)0.117 (2)0.108 (3)0.0049 (19)0.0197 (19)0.054 (2)
Geometric parameters (Å, º) top
N1—C61.340 (3)C16—C171.380 (3)
N1—C21.348 (3)C17—C181.366 (3)
N2—C81.289 (3)C17—H170.930
N2—C61.399 (3)C18—C191.368 (4)
N3—C81.387 (3)C18—H180.930
N3—C151.389 (3)C19—C201.386 (4)
N3—H30.860C19—H190.930
N4—C151.281 (3)C20—C221.508 (4)
N4—C161.408 (3)C22—H22A0.960
N5—C161.343 (3)C22—H22B0.960
N5—C201.351 (3)C22—H22C0.960
N6—C241.346 (3)C23—C241.503 (4)
N6—C281.349 (3)C23—H23A0.960
N7—C301.284 (3)C23—H23B0.960
N7—C281.393 (3)C23—H23C0.960
N8—C371.390 (3)C24—C251.383 (4)
N8—C301.392 (3)C25—C261.366 (4)
N8—H80.860C25—H250.930
N9—C371.279 (3)C26—C271.372 (4)
N9—C381.405 (3)C26—H260.930
N10—C381.341 (3)C27—C281.390 (3)
N10—C421.349 (3)C27—H270.930
C1—C21.487 (4)C30—C311.472 (3)
C1—H1A0.960C31—C361.380 (3)
C1—H1B0.960C31—C321.383 (3)
C1—H1C0.960C32—C331.384 (3)
C2—C31.372 (4)C32—H320.930
C3—C41.369 (4)C33—C341.383 (3)
C3—H3A0.930C33—H330.930
C4—C51.370 (4)C34—C351.379 (3)
C4—H40.930C34—H340.930
C5—C61.390 (3)C35—C361.379 (3)
C5—H50.930C35—H350.930
C8—C91.467 (3)C36—C371.474 (3)
C9—C141.387 (3)C38—C391.386 (3)
C9—C101.391 (3)C39—C401.373 (3)
C10—C111.377 (4)C39—H390.930
C10—H100.930C40—C411.371 (4)
C11—C121.383 (4)C40—H400.930
C11—H110.930C41—C421.385 (4)
C12—C131.393 (4)C41—H410.930
C12—H120.930C42—C441.493 (4)
C13—C141.377 (3)C44—H44A0.960
C13—H130.930C44—H44B0.960
C14—C151.475 (3)C44—H44C0.960
C6—N1—C2118.0 (2)C19—C20—C22122.3 (3)
C8—N2—C6122.8 (2)C20—C22—H22A109.5
C8—N3—C15112.6 (2)C20—C22—H22B109.5
C8—N3—H3123.7H22A—C22—H22B109.5
C15—N3—H3123.7C20—C22—H22C109.5
C15—N4—C16122.1 (2)H22A—C22—H22C109.5
C16—N5—C20117.6 (2)H22B—C22—H22C109.5
C24—N6—C28118.5 (2)C24—C23—H23A109.5
C30—N7—C28123.0 (2)C24—C23—H23B109.5
C37—N8—C30112.13 (19)H23A—C23—H23B109.5
C37—N8—H8123.9C24—C23—H23C109.5
C30—N8—H8123.9H23A—C23—H23C109.5
C37—N9—C38121.9 (2)H23B—C23—H23C109.5
C38—N10—C42117.9 (2)N6—C24—C25121.7 (3)
C2—C1—H1A109.5N6—C24—C23116.7 (2)
C2—C1—H1B109.5C25—C24—C23121.6 (3)
H1A—C1—H1B109.5C26—C25—C24119.3 (3)
C2—C1—H1C109.5C26—C25—H25120.4
H1A—C1—H1C109.5C24—C25—H25120.4
H1B—C1—H1C109.5C25—C26—C27120.0 (3)
N1—C2—C3122.2 (2)C25—C26—H26120.0
N1—C2—C1115.3 (3)C27—C26—H26120.0
C3—C2—C1122.5 (3)C26—C27—C28118.4 (3)
C4—C3—C2119.4 (3)C26—C27—H27120.8
C4—C3—H3A120.3C28—C27—H27120.8
C2—C3—H3A120.3N6—C28—C27122.0 (3)
C5—C4—C3119.5 (3)N6—C28—N7121.0 (2)
C5—C4—H4120.3C27—C28—N7117.0 (2)
C3—C4—H4120.3N7—C30—N8130.5 (2)
C4—C5—C6118.6 (3)N7—C30—C31124.1 (2)
C4—C5—H5120.7N8—C30—C31105.39 (19)
C6—C5—H5120.7C36—C31—C32121.7 (2)
N1—C6—C5122.3 (2)C36—C31—C30108.54 (19)
N1—C6—N2120.8 (2)C32—C31—C30129.8 (2)
C5—C6—N2116.9 (2)C31—C32—C33116.7 (2)
N2—C8—N3131.0 (2)C31—C32—H32121.7
N2—C8—C9123.5 (2)C33—C32—H32121.7
N3—C8—C9105.5 (2)C34—C33—C32121.6 (2)
C14—C9—C10121.1 (2)C34—C33—H33119.2
C14—C9—C8108.5 (2)C32—C33—H33119.2
C10—C9—C8130.4 (2)C35—C34—C33121.2 (2)
C11—C10—C9117.6 (3)C35—C34—H34119.4
C11—C10—H10121.2C33—C34—H34119.4
C9—C10—H10121.2C34—C35—C36117.4 (2)
C10—C11—C12121.5 (3)C34—C35—H35121.3
C10—C11—H11119.2C36—C35—H35121.3
C12—C11—H11119.2C35—C36—C31121.4 (2)
C11—C12—C13120.8 (3)C35—C36—C37130.5 (2)
C11—C12—H12119.6C31—C36—C37108.2 (2)
C13—C12—H12119.6N9—C37—N8130.4 (2)
C14—C13—C12117.9 (3)N9—C37—C36123.8 (2)
C14—C13—H13121.1N8—C37—C36105.58 (18)
C12—C13—H13121.1N10—C38—C39122.7 (2)
C13—C14—C9121.1 (2)N10—C38—N9120.1 (2)
C13—C14—C15130.8 (3)C39—C38—N9117.1 (2)
C9—C14—C15108.1 (2)C40—C39—C38118.8 (3)
N4—C15—N3130.5 (2)C40—C39—H39120.6
N4—C15—C14124.1 (2)C38—C39—H39120.6
N3—C15—C14105.3 (2)C39—C40—C41119.1 (3)
N5—C16—C17123.0 (3)C39—C40—H40120.4
N5—C16—N4118.7 (2)C41—C40—H40120.4
C17—C16—N4118.1 (3)C40—C41—C42119.5 (3)
C18—C17—C16118.8 (3)C40—C41—H41120.2
C18—C17—H17120.6C42—C41—H41120.2
C16—C17—H17120.6N10—C42—C41121.8 (3)
C17—C18—C19119.4 (3)N10—C42—C44116.7 (3)
C17—C18—H18120.3C41—C42—C44121.4 (3)
C19—C18—H18120.3C42—C44—H44A109.5
C18—C19—C20119.5 (3)C42—C44—H44B109.5
C18—C19—H19120.3H44A—C44—H44B109.5
C20—C19—H19120.3C42—C44—H44C109.5
N5—C20—C19121.7 (3)H44A—C44—H44C109.5
N5—C20—C22116.0 (3)H44B—C44—H44C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···N10.862.192.710 (3)119
N3—H3···N50.862.482.910 (3)112
N8—H8···N60.862.182.702 (3)118
N8—H8···N100.862.392.853 (3)114
 

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