Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520622000191/um5054sup1.cif | |
Zip compressed file https://doi.org/10.1107/S2052520622000191/um5054sup2.zip | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520622000191/um5054mo_sp20030_0m_0p0000GPasup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520622000191/um5054mo_sp20038_0m_0p3568GPasup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520622000191/um5054mo_sp20040_0m_0p6591GPasup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520622000191/um5054mo_sp20034_0m_0p8792GPasup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520622000191/um5054mo_sp20041_0m_1p0994GPasup7.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520622000191/um5054sp20043_0m_1p3749GPasup8.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520622000191/um5054sp20035_0m_1p8162GPasup9.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520622000191/um5054mo_sp20037_0m_2p5349GPasup10.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520622000191/um5054mo_sp20051_0m_2p5349GPasup11.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520622000191/um5054mo_sp20039_0m_3p4218GPasup12.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520622000191/um5054sp20042_0m_4p0054GPasup13.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520622000191/um5054mo_sp20044_0m_4p7574GPasup14.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520622000191/um5054mo_sp20048_0m_5p3456GPasup15.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520622000191/um5054mo_sp20050_0m_5p5393GPasup16.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520622000191/um5054mo_sp20052_0m_5p7631GPasup17.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520622000191/um5054mo_sp20053_0m_6p0711GPasup18.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520622000191/um5054mo_sp20049_0m_2p1201GPasup19.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520622000191/um5054sup20.pdf |
CCDC references: 2132733; 2132734; 2132735; 2132736; 2132737; 2132738; 2132739; 2132740; 2132741; 2132742; 2132743; 2132744; 2132745; 2132746; 2132747; 2132748; 2132749
Cell refinement: SAINT V8.40A (Bruker, 2019) for mo_sp20030_0m_0p0000GPa, mo_sp20038_0m_0p3568GPa, mo_sp20040_0m_0p6591GPa, mo_sp20034_0m_0p8792GPa, mo_sp20041_0m_1p0994GPa, mo_sp20049_0m_2p1201GPa, mo_sp20037_0m_2p5349GPa, mo_sp20051_0m_2p5349GPa, mo_sp20039_0m_3p4218GPa, mo_sp20044_0m_4p7574GPa, mo_sp20048_0m_5p3456GPa, mo_sp20050_0m_5p5393GPa, mo_sp20052_0m_5p7631GPa, mo_sp20053_0m_6p0711GPa; SAINT V8.38A (Bruker, 2018) for sp20043_0m_1p3749GPa, sp20035_0m_1p8162GPa, sp20042_0m_4p0054GPa. Data reduction: SAINT V8.40A (Bruker, 2019) for mo_sp20030_0m_0p0000GPa, mo_sp20038_0m_0p3568GPa, mo_sp20040_0m_0p6591GPa, mo_sp20034_0m_0p8792GPa, mo_sp20041_0m_1p0994GPa, mo_sp20049_0m_2p1201GPa, mo_sp20037_0m_2p5349GPa, mo_sp20051_0m_2p5349GPa, mo_sp20039_0m_3p4218GPa, mo_sp20044_0m_4p7574GPa, mo_sp20048_0m_5p3456GPa, mo_sp20050_0m_5p5393GPa, mo_sp20052_0m_5p7631GPa, mo_sp20053_0m_6p0711GPa; SAINT V8.38A (Bruker, 2018) for sp20043_0m_1p3749GPa, sp20035_0m_1p8162GPa, sp20042_0m_4p0054GPa. For all structures, program(s) used to solve structure: SHELXT 2014/5 (Sheldrick, 2014); program(s) used to refine structure: XL (Sheldrick, 2008); molecular graphics: Olex2 1.3 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 1.3 (Dolomanov et al., 2009).
C19H14N3 | F(000) = 596 |
Mr = 284.33 | Dx = 1.319 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.4887 (4) Å | Cell parameters from 1691 reflections |
b = 6.9632 (2) Å | θ = 3.1–26.9° |
c = 19.8755 (7) Å | µ = 0.08 mm−1 |
β = 99.441 (2)° | T = 298 K |
V = 1431.94 (9) Å3 | Block, clear dark brown |
Z = 4 | 0.6 × 0.4 × 0.2 mm |
Bruker SMART APEX2 area detector diffractometer | 2511 independent reflections |
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs | 1422 reflections with I > 2σ(I) |
Mirror optics monochromator | Rint = 0.044 |
Detector resolution: 7.9 pixels mm-1 | θmax = 25.0°, θmin = 3.1° |
ω and φ scans | h = −12→12 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1139 before and 0.0475 after correction. The Ratio of minimum to maximum transmission is 0.8684. The λ/2 correction factor is Not present. | k = −7→8 |
Tmin = 0.648, Tmax = 0.746 | l = −23→23 |
8006 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.057 | w = 1/[σ2(Fo2) + (0.0809P)2 + 0.4711P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.188 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.20 e Å−3 |
2511 reflections | Δρmin = −0.17 e Å−3 |
200 parameters | Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.047 (9) |
Primary atom site location: dual |
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. PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 3 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ··· 2 Note PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ·········.. 3.2 Low PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info PLAT992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by 3 Check No action taken. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.47277 (18) | 0.7135 (3) | 0.65732 (10) | 0.0500 (6) | |
N2 | 0.44116 (18) | 0.7102 (3) | 0.72165 (10) | 0.0493 (6) | |
N3 | 0.21677 (19) | 0.7023 (3) | 0.67222 (10) | 0.0496 (6) | |
C1 | 0.3146 (2) | 0.7057 (3) | 0.72431 (12) | 0.0445 (6) | |
C2 | 0.2504 (2) | 0.6947 (4) | 0.60833 (12) | 0.0476 (6) | |
C7 | 0.1546 (2) | 0.6784 (4) | 0.55078 (13) | 0.0572 (7) | |
H7 | 0.068123 | 0.678123 | 0.556031 | 0.069* | |
C6 | 0.1861 (3) | 0.6627 (4) | 0.48665 (14) | 0.0623 (8) | |
H6 | 0.121366 | 0.650566 | 0.448864 | 0.075* | |
C5 | 0.3151 (3) | 0.6651 (4) | 0.47839 (14) | 0.0626 (8) | |
H5 | 0.336156 | 0.654068 | 0.434883 | 0.075* | |
C4 | 0.4120 (3) | 0.6835 (4) | 0.53350 (13) | 0.0572 (7) | |
H4 | 0.497965 | 0.685476 | 0.527336 | 0.069* | |
C3 | 0.3806 (2) | 0.6993 (3) | 0.59884 (12) | 0.0462 (6) | |
C14 | 0.6092 (2) | 0.7135 (4) | 0.65722 (12) | 0.0510 (7) | |
C19 | 0.6638 (3) | 0.8499 (4) | 0.62063 (14) | 0.0623 (8) | |
H19 | 0.612392 | 0.943344 | 0.596110 | 0.075* | |
C18 | 0.7956 (3) | 0.8469 (5) | 0.62065 (15) | 0.0754 (10) | |
H18 | 0.832406 | 0.937338 | 0.595260 | 0.091* | |
C17 | 0.8721 (3) | 0.7130 (6) | 0.65738 (15) | 0.0811 (11) | |
H17 | 0.960693 | 0.712723 | 0.657157 | 0.097* | |
C16 | 0.8179 (3) | 0.5772 (6) | 0.69507 (15) | 0.0787 (10) | |
H16 | 0.869993 | 0.485402 | 0.720083 | 0.094* | |
C15 | 0.6851 (2) | 0.5784 (5) | 0.69543 (13) | 0.0639 (8) | |
H15 | 0.648197 | 0.488986 | 0.721193 | 0.077* | |
C8 | 0.2822 (2) | 0.7030 (3) | 0.79431 (12) | 0.0458 (6) | |
C9 | 0.1550 (2) | 0.7185 (4) | 0.80359 (14) | 0.0551 (7) | |
H9 | 0.089992 | 0.731916 | 0.766000 | 0.066* | |
C10 | 0.1239 (3) | 0.7141 (4) | 0.86849 (15) | 0.0642 (8) | |
H10 | 0.038003 | 0.726430 | 0.874163 | 0.077* | |
C11 | 0.2180 (3) | 0.6917 (4) | 0.92472 (15) | 0.0648 (8) | |
H11 | 0.196324 | 0.687290 | 0.968234 | 0.078* | |
C12 | 0.3449 (3) | 0.6760 (4) | 0.91559 (14) | 0.0659 (8) | |
H12 | 0.409440 | 0.661195 | 0.953332 | 0.079* | |
C13 | 0.3776 (3) | 0.6821 (4) | 0.85094 (13) | 0.0577 (7) | |
H13 | 0.463724 | 0.672127 | 0.845482 | 0.069* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0398 (11) | 0.0673 (14) | 0.0437 (12) | 0.0008 (10) | 0.0098 (9) | 0.0009 (10) |
N2 | 0.0432 (11) | 0.0626 (13) | 0.0432 (12) | −0.0003 (10) | 0.0104 (9) | −0.0016 (10) |
N3 | 0.0433 (11) | 0.0584 (13) | 0.0473 (12) | 0.0024 (10) | 0.0080 (9) | −0.0011 (10) |
C1 | 0.0399 (12) | 0.0456 (13) | 0.0481 (14) | 0.0015 (10) | 0.0080 (11) | −0.0007 (11) |
C2 | 0.0457 (13) | 0.0522 (14) | 0.0453 (14) | 0.0047 (11) | 0.0086 (11) | 0.0009 (11) |
C7 | 0.0466 (14) | 0.0721 (18) | 0.0514 (15) | 0.0042 (13) | 0.0031 (12) | −0.0021 (13) |
C6 | 0.0566 (16) | 0.079 (2) | 0.0480 (16) | 0.0061 (14) | −0.0011 (12) | −0.0028 (13) |
C5 | 0.0613 (16) | 0.078 (2) | 0.0483 (16) | 0.0048 (15) | 0.0099 (13) | −0.0028 (14) |
C4 | 0.0503 (14) | 0.0748 (18) | 0.0473 (15) | 0.0026 (13) | 0.0104 (12) | −0.0008 (13) |
C3 | 0.0450 (13) | 0.0512 (14) | 0.0425 (14) | 0.0021 (11) | 0.0075 (10) | −0.0013 (11) |
C14 | 0.0390 (12) | 0.0697 (17) | 0.0449 (14) | 0.0000 (12) | 0.0090 (10) | −0.0060 (12) |
C19 | 0.0530 (15) | 0.0792 (19) | 0.0558 (16) | −0.0048 (14) | 0.0121 (12) | 0.0003 (14) |
C18 | 0.0526 (16) | 0.117 (3) | 0.0582 (18) | −0.0184 (18) | 0.0144 (14) | −0.0036 (18) |
C17 | 0.0454 (15) | 0.149 (3) | 0.0494 (17) | −0.0028 (19) | 0.0103 (13) | −0.0115 (19) |
C16 | 0.0510 (15) | 0.128 (3) | 0.0547 (17) | 0.0218 (19) | 0.0023 (13) | 0.0022 (19) |
C15 | 0.0507 (14) | 0.092 (2) | 0.0499 (16) | 0.0073 (15) | 0.0105 (12) | 0.0085 (15) |
C8 | 0.0452 (13) | 0.0479 (13) | 0.0454 (14) | −0.0038 (11) | 0.0110 (11) | −0.0030 (11) |
C9 | 0.0488 (14) | 0.0648 (16) | 0.0531 (16) | −0.0035 (13) | 0.0130 (12) | −0.0030 (13) |
C10 | 0.0584 (16) | 0.0738 (19) | 0.0659 (19) | −0.0050 (14) | 0.0267 (14) | −0.0074 (15) |
C11 | 0.0762 (19) | 0.0720 (19) | 0.0502 (16) | −0.0083 (16) | 0.0221 (14) | −0.0049 (14) |
C12 | 0.0635 (17) | 0.085 (2) | 0.0487 (16) | −0.0058 (16) | 0.0067 (13) | −0.0007 (14) |
C13 | 0.0503 (14) | 0.0743 (18) | 0.0492 (15) | −0.0007 (13) | 0.0097 (12) | −0.0018 (13) |
N1—N2 | 1.373 (3) | C19—C18 | 1.383 (4) |
N1—C3 | 1.388 (3) | C18—H18 | 0.9300 |
N1—C14 | 1.432 (3) | C18—C17 | 1.362 (5) |
N2—C1 | 1.338 (3) | C17—H17 | 0.9300 |
N3—C1 | 1.333 (3) | C17—C16 | 1.385 (5) |
N3—C2 | 1.374 (3) | C16—H16 | 0.9300 |
C1—C8 | 1.486 (3) | C16—C15 | 1.394 (4) |
C2—C7 | 1.398 (3) | C15—H15 | 0.9300 |
C2—C3 | 1.409 (3) | C8—C9 | 1.380 (3) |
C7—H7 | 0.9300 | C8—C13 | 1.386 (3) |
C7—C6 | 1.373 (4) | C9—H9 | 0.9300 |
C6—H6 | 0.9300 | C9—C10 | 1.382 (4) |
C6—C5 | 1.390 (4) | C10—H10 | 0.9300 |
C5—H5 | 0.9300 | C10—C11 | 1.373 (4) |
C5—C4 | 1.372 (4) | C11—H11 | 0.9300 |
C4—H4 | 0.9300 | C11—C12 | 1.377 (4) |
C4—C3 | 1.395 (3) | C12—H12 | 0.9300 |
C14—C19 | 1.377 (4) | C12—C13 | 1.384 (4) |
C14—C15 | 1.377 (4) | C13—H13 | 0.9300 |
C19—H19 | 0.9300 | ||
N2—N1—C3 | 122.51 (18) | C18—C19—H19 | 120.3 |
N2—N1—C14 | 113.30 (18) | C19—C18—H18 | 119.6 |
C3—N1—C14 | 123.91 (19) | C17—C18—C19 | 120.8 (3) |
C1—N2—N1 | 115.48 (19) | C17—C18—H18 | 119.6 |
C1—N3—C2 | 115.9 (2) | C18—C17—H17 | 120.0 |
N2—C1—C8 | 114.7 (2) | C18—C17—C16 | 120.0 (3) |
N3—C1—N2 | 127.8 (2) | C16—C17—H17 | 120.0 |
N3—C1—C8 | 117.5 (2) | C17—C16—H16 | 120.1 |
N3—C2—C7 | 120.0 (2) | C17—C16—C15 | 119.8 (3) |
N3—C2—C3 | 121.6 (2) | C15—C16—H16 | 120.1 |
C7—C2—C3 | 118.3 (2) | C14—C15—C16 | 119.3 (3) |
C2—C7—H7 | 119.5 | C14—C15—H15 | 120.4 |
C6—C7—C2 | 121.1 (2) | C16—C15—H15 | 120.4 |
C6—C7—H7 | 119.5 | C9—C8—C1 | 119.9 (2) |
C7—C6—H6 | 120.1 | C9—C8—C13 | 119.0 (2) |
C7—C6—C5 | 119.7 (2) | C13—C8—C1 | 121.1 (2) |
C5—C6—H6 | 120.1 | C8—C9—H9 | 119.9 |
C6—C5—H5 | 119.5 | C8—C9—C10 | 120.3 (3) |
C4—C5—C6 | 121.0 (3) | C10—C9—H9 | 119.9 |
C4—C5—H5 | 119.5 | C9—C10—H10 | 119.5 |
C5—C4—H4 | 120.2 | C11—C10—C9 | 120.9 (3) |
C5—C4—C3 | 119.6 (2) | C11—C10—H10 | 119.5 |
C3—C4—H4 | 120.2 | C10—C11—H11 | 120.6 |
N1—C3—C2 | 116.5 (2) | C10—C11—C12 | 118.9 (3) |
N1—C3—C4 | 123.2 (2) | C12—C11—H11 | 120.6 |
C4—C3—C2 | 120.3 (2) | C11—C12—H12 | 119.6 |
C19—C14—N1 | 120.2 (2) | C11—C12—C13 | 120.8 (3) |
C19—C14—C15 | 120.7 (2) | C13—C12—H12 | 119.6 |
C15—C14—N1 | 119.1 (2) | C8—C13—H13 | 120.0 |
C14—C19—H19 | 120.3 | C12—C13—C8 | 120.1 (2) |
C14—C19—C18 | 119.4 (3) | C12—C13—H13 | 120.0 |
N1—N2—C1—N3 | 0.7 (4) | C7—C6—C5—C4 | −0.2 (4) |
N1—N2—C1—C8 | −179.78 (19) | C6—C5—C4—C3 | 0.3 (4) |
N1—C14—C19—C18 | −179.5 (3) | C5—C4—C3—N1 | 178.3 (2) |
N1—C14—C15—C16 | 179.6 (3) | C5—C4—C3—C2 | 0.6 (4) |
N2—N1—C3—C2 | 4.3 (3) | C3—N1—N2—C1 | −4.4 (3) |
N2—N1—C3—C4 | −173.5 (2) | C3—N1—C14—C19 | 57.9 (3) |
N2—N1—C14—C19 | −128.1 (2) | C3—N1—C14—C15 | −123.7 (3) |
N2—N1—C14—C15 | 50.4 (3) | C3—C2—C7—C6 | 1.5 (4) |
N2—C1—C8—C9 | 173.3 (2) | C14—N1—N2—C1 | −178.6 (2) |
N2—C1—C8—C13 | −7.7 (3) | C14—N1—C3—C2 | 177.8 (2) |
N3—C1—C8—C9 | −7.1 (3) | C14—N1—C3—C4 | 0.0 (4) |
N3—C1—C8—C13 | 171.9 (2) | C14—C19—C18—C17 | −1.2 (5) |
N3—C2—C7—C6 | −177.4 (2) | C19—C14—C15—C16 | −2.0 (4) |
N3—C2—C3—N1 | −0.5 (3) | C19—C18—C17—C16 | 0.3 (5) |
N3—C2—C3—C4 | 177.4 (2) | C18—C17—C16—C15 | −0.2 (5) |
C1—N3—C2—C7 | 176.0 (2) | C17—C16—C15—C14 | 1.0 (5) |
C1—N3—C2—C3 | −2.8 (3) | C15—C14—C19—C18 | 2.1 (4) |
C1—C8—C9—C10 | 179.3 (2) | C8—C9—C10—C11 | −0.9 (4) |
C1—C8—C13—C12 | −178.7 (2) | C9—C8—C13—C12 | 0.3 (4) |
C2—N3—C1—N2 | 2.9 (4) | C9—C10—C11—C12 | 0.8 (4) |
C2—N3—C1—C8 | −176.7 (2) | C10—C11—C12—C13 | −0.2 (5) |
C2—C7—C6—C5 | −0.7 (4) | C11—C12—C13—C8 | −0.4 (4) |
C7—C2—C3—N1 | −179.3 (2) | C13—C8—C9—C10 | 0.3 (4) |
C7—C2—C3—C4 | −1.4 (4) |
C19H14N3 | F(000) = 596 |
Mr = 284.33 | Dx = 1.371 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.4160 (6) Å | Cell parameters from 2275 reflections |
b = 6.8137 (4) Å | θ = 3.2–26.2° |
c = 19.690 (2) Å | µ = 0.08 mm−1 |
β = 99.691 (6)° | T = 295 K |
V = 1377.5 (2) Å3 | Block, clear dark brown |
Z = 4 | 0.18 × 0.14 × 0.09 mm |
Bruker SMART APEX2 area detector diffractometer | 968 independent reflections |
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs | 641 reflections with I > 2σ(I) |
Mirror optics monochromator | Rint = 0.041 |
Detector resolution: 7.9 pixels mm-1 | θmax = 26.4°, θmin = 2.1° |
ω and φ scans | h = −12→12 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0501 before and 0.0399 after correction. The Ratio of minimum to maximum transmission is 0.9005. The λ/2 correction factor is Not present. | k = −8→8 |
Tmin = 0.671, Tmax = 0.745 | l = −8→8 |
8076 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.100 | w = 1/[σ2(Fo2) + (0.0512P)2 + 0.2479P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
968 reflections | Δρmax = 0.09 e Å−3 |
199 parameters | Δρmin = −0.08 e Å−3 |
231 restraints |
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. High pressure data collection in a diamond anvil cell. 0.3568 GPa. PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT152_ALERT_1_G The Supplied and Calc. Volume s.u. Differ by ··· -2 Units PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 231 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 65 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 16 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 16 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info No action taken. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.4732 (2) | 0.7121 (3) | 0.6583 (3) | 0.037 (3) | |
N2 | 0.4421 (2) | 0.7081 (3) | 0.7223 (3) | 0.037 (3) | |
N3 | 0.2164 (2) | 0.6985 (3) | 0.6727 (4) | 0.036 (3) | |
C1 | 0.3138 (3) | 0.7026 (4) | 0.7254 (4) | 0.030 (3) | |
C2 | 0.2486 (3) | 0.6921 (4) | 0.6081 (4) | 0.033 (3) | |
C7 | 0.1531 (3) | 0.6745 (4) | 0.5508 (4) | 0.037 (3) | |
H7 | 0.066117 | 0.672148 | 0.556177 | 0.045* | |
C6 | 0.1836 (3) | 0.6606 (5) | 0.4864 (4) | 0.044 (3) | |
H6 | 0.117324 | 0.648061 | 0.448622 | 0.052* | |
C5 | 0.3139 (3) | 0.6649 (3) | 0.4765 (3) | 0.045 (3) | |
H5 | 0.334213 | 0.654947 | 0.432349 | 0.053* | |
C4 | 0.4111 (3) | 0.6838 (4) | 0.5326 (4) | 0.040 (3) | |
H4 | 0.497724 | 0.687165 | 0.526484 | 0.048* | |
C3 | 0.3809 (3) | 0.6980 (4) | 0.5983 (4) | 0.034 (3) | |
C14 | 0.61121 (19) | 0.7125 (3) | 0.6573 (3) | 0.029 (3) | |
C19 | 0.6654 (2) | 0.8514 (4) | 0.6207 (3) | 0.041 (4) | |
H19 | 0.613012 | 0.946484 | 0.595963 | 0.049* | |
C18 | 0.7981 (2) | 0.8503 (4) | 0.6204 (3) | 0.054 (4) | |
H18 | 0.834896 | 0.943081 | 0.594858 | 0.065* | |
C17 | 0.8746 (3) | 0.7130 (5) | 0.6576 (4) | 0.063 (4) | |
H17 | 0.963757 | 0.712357 | 0.657345 | 0.076* | |
C16 | 0.8212 (2) | 0.5749 (5) | 0.6958 (4) | 0.054 (4) | |
H16 | 0.874270 | 0.482446 | 0.721530 | 0.065* | |
C15 | 0.6872 (2) | 0.5745 (4) | 0.6957 (3) | 0.044 (4) | |
H15 | 0.650027 | 0.482046 | 0.721232 | 0.053* | |
C8 | 0.2831 (3) | 0.6993 (4) | 0.7961 (4) | 0.033 (3) | |
C9 | 0.1536 (3) | 0.7171 (4) | 0.8052 (4) | 0.039 (4) | |
H9 | 0.088039 | 0.732819 | 0.767282 | 0.047* | |
C10 | 0.1233 (3) | 0.7112 (4) | 0.8706 (4) | 0.045 (4) | |
H10 | 0.036890 | 0.722658 | 0.876465 | 0.054* | |
C11 | 0.2178 (3) | 0.6889 (4) | 0.9268 (4) | 0.047 (4) | |
H11 | 0.196291 | 0.685255 | 0.970754 | 0.057* | |
C12 | 0.3461 (3) | 0.6718 (4) | 0.9180 (4) | 0.048 (3) | |
H12 | 0.411195 | 0.656274 | 0.956202 | 0.058* | |
C13 | 0.3782 (3) | 0.6776 (4) | 0.8533 (4) | 0.041 (3) | |
H13 | 0.464933 | 0.666695 | 0.847986 | 0.049* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0278 (13) | 0.0504 (13) | 0.034 (9) | 0.0009 (10) | 0.007 (2) | −0.001 (2) |
N2 | 0.0269 (13) | 0.0509 (13) | 0.035 (9) | −0.0010 (9) | 0.005 (3) | −0.002 (2) |
N3 | 0.0292 (14) | 0.0460 (13) | 0.031 (9) | 0.0019 (10) | 0.000 (3) | 0.001 (2) |
C1 | 0.0248 (14) | 0.0342 (13) | 0.031 (9) | −0.0001 (10) | 0.002 (3) | 0.000 (3) |
C2 | 0.0333 (18) | 0.0381 (14) | 0.027 (9) | 0.0023 (11) | 0.004 (3) | −0.003 (3) |
C7 | 0.0268 (15) | 0.0554 (16) | 0.027 (10) | 0.0035 (12) | −0.003 (3) | 0.002 (3) |
C6 | 0.0432 (18) | 0.0587 (17) | 0.028 (11) | 0.0032 (13) | 0.004 (3) | −0.005 (4) |
C5 | 0.0435 (15) | 0.0617 (16) | 0.029 (11) | 0.0030 (12) | 0.007 (3) | 0.000 (3) |
C4 | 0.0318 (16) | 0.0574 (17) | 0.032 (10) | 0.0016 (12) | 0.009 (3) | 0.000 (3) |
C3 | 0.0288 (16) | 0.0394 (14) | 0.033 (10) | 0.0015 (11) | 0.004 (3) | −0.002 (3) |
C14 | 0.0238 (11) | 0.0514 (14) | 0.010 (10) | 0.0010 (10) | 0.001 (2) | −0.002 (2) |
C19 | 0.0382 (13) | 0.0577 (16) | 0.027 (12) | −0.0039 (11) | 0.006 (3) | −0.001 (2) |
C18 | 0.0370 (14) | 0.090 (2) | 0.036 (14) | −0.0177 (13) | 0.010 (3) | 0.000 (3) |
C17 | 0.0281 (13) | 0.114 (3) | 0.047 (13) | −0.0011 (15) | 0.008 (3) | −0.002 (3) |
C16 | 0.0386 (14) | 0.100 (2) | 0.020 (14) | 0.0191 (14) | −0.005 (3) | 0.003 (3) |
C15 | 0.0375 (13) | 0.0688 (18) | 0.027 (12) | 0.0053 (11) | 0.009 (2) | 0.005 (3) |
C8 | 0.0322 (16) | 0.0365 (13) | 0.033 (9) | −0.0022 (11) | 0.013 (3) | 0.000 (3) |
C9 | 0.0309 (16) | 0.0496 (15) | 0.036 (11) | −0.0010 (10) | 0.006 (3) | 0.002 (3) |
C10 | 0.0387 (17) | 0.0591 (17) | 0.040 (12) | −0.0049 (13) | 0.016 (3) | −0.002 (3) |
C11 | 0.0562 (18) | 0.0574 (17) | 0.033 (12) | −0.0089 (13) | 0.018 (3) | −0.003 (3) |
C12 | 0.050 (2) | 0.0609 (18) | 0.034 (11) | −0.0040 (14) | 0.007 (4) | 0.001 (4) |
C13 | 0.0315 (16) | 0.0565 (16) | 0.034 (10) | −0.0011 (13) | 0.006 (3) | −0.003 (3) |
N1—N2 | 1.352 (7) | C19—C18 | 1.383 (3) |
N1—C3 | 1.397 (7) | C18—H18 | 0.9300 |
N1—C14 | 1.441 (3) | C18—C17 | 1.360 (5) |
N2—C1 | 1.349 (4) | C17—H17 | 0.9300 |
N3—C1 | 1.323 (6) | C17—C16 | 1.378 (6) |
N3—C2 | 1.371 (8) | C16—H16 | 0.9300 |
C1—C8 | 1.482 (7) | C16—C15 | 1.395 (3) |
C2—C7 | 1.378 (7) | C15—H15 | 0.9300 |
C2—C3 | 1.423 (5) | C8—C9 | 1.395 (4) |
C7—H7 | 0.9300 | C8—C13 | 1.376 (7) |
C7—C6 | 1.360 (8) | C9—H9 | 0.9300 |
C6—H6 | 0.9300 | C9—C10 | 1.377 (8) |
C6—C5 | 1.405 (4) | C10—H10 | 0.9300 |
C5—H5 | 0.9300 | C10—C11 | 1.360 (7) |
C5—C4 | 1.374 (7) | C11—H11 | 0.9300 |
C4—H4 | 0.9300 | C11—C12 | 1.381 (4) |
C4—C3 | 1.385 (8) | C12—H12 | 0.9300 |
C14—C19 | 1.368 (5) | C12—C13 | 1.371 (8) |
C14—C15 | 1.372 (5) | C13—H13 | 0.9300 |
C19—H19 | 0.9300 | ||
N2—N1—C3 | 123.3 (3) | C18—C19—H19 | 120.0 |
N2—N1—C14 | 114.2 (5) | C19—C18—H18 | 120.1 |
C3—N1—C14 | 122.3 (5) | C17—C18—C19 | 119.8 (4) |
C1—N2—N1 | 115.9 (5) | C17—C18—H18 | 120.1 |
C1—N3—C2 | 116.9 (4) | C18—C17—H17 | 119.7 |
N2—C1—C8 | 114.5 (5) | C18—C17—C16 | 120.7 (3) |
N3—C1—N2 | 126.9 (6) | C16—C17—H17 | 119.7 |
N3—C1—C8 | 118.5 (3) | C17—C16—H16 | 120.1 |
N3—C2—C7 | 120.5 (4) | C17—C16—C15 | 119.7 (3) |
N3—C2—C3 | 121.3 (5) | C15—C16—H16 | 120.1 |
C7—C2—C3 | 118.2 (6) | C14—C15—C16 | 118.9 (3) |
C2—C7—H7 | 119.4 | C14—C15—H15 | 120.5 |
C6—C7—C2 | 121.3 (4) | C16—C15—H15 | 120.5 |
C6—C7—H7 | 119.4 | C9—C8—C1 | 119.1 (5) |
C7—C6—H6 | 119.6 | C13—C8—C1 | 122.1 (3) |
C7—C6—C5 | 120.8 (5) | C13—C8—C9 | 118.8 (6) |
C5—C6—H6 | 119.6 | C8—C9—H9 | 120.1 |
C6—C5—H5 | 120.4 | C10—C9—C8 | 119.7 (5) |
C4—C5—C6 | 119.2 (6) | C10—C9—H9 | 120.1 |
C4—C5—H5 | 120.4 | C9—C10—H10 | 119.5 |
C5—C4—H4 | 119.8 | C11—C10—C9 | 121.0 (4) |
C5—C4—C3 | 120.3 (3) | C11—C10—H10 | 119.5 |
C3—C4—H4 | 119.8 | C10—C11—H11 | 120.3 |
N1—C3—C2 | 115.5 (6) | C10—C11—C12 | 119.4 (6) |
C4—C3—N1 | 124.3 (3) | C12—C11—H11 | 120.3 |
C4—C3—C2 | 120.2 (5) | C11—C12—H12 | 119.8 |
C19—C14—N1 | 120.7 (3) | C13—C12—C11 | 120.4 (6) |
C19—C14—C15 | 120.9 (2) | C13—C12—H12 | 119.8 |
C15—C14—N1 | 118.4 (3) | C8—C13—H13 | 119.7 |
C14—C19—H19 | 120.0 | C12—C13—C8 | 120.6 (4) |
C14—C19—C18 | 120.0 (3) | C12—C13—H13 | 119.7 |
N1—N2—C1—N3 | 0.8 (4) | C7—C6—C5—C4 | −0.2 (5) |
N1—N2—C1—C8 | −179.7 (2) | C6—C5—C4—C3 | 0.2 (5) |
N1—C14—C19—C18 | 179.7 (5) | C5—C4—C3—N1 | 178.1 (2) |
N1—C14—C15—C16 | −179.2 (5) | C5—C4—C3—C2 | 0.3 (5) |
N2—N1—C3—C2 | 4.1 (4) | C3—N1—N2—C1 | −4.3 (4) |
N2—N1—C3—C4 | −173.8 (3) | C3—N1—C14—C19 | 58.0 (5) |
N2—N1—C14—C19 | −127.8 (4) | C3—N1—C14—C15 | −124.1 (5) |
N2—N1—C14—C15 | 50.1 (5) | C3—C2—C7—C6 | 0.8 (5) |
N2—C1—C8—C9 | 172.4 (2) | C14—N1—N2—C1 | −178.38 (19) |
N2—C1—C8—C13 | −8.1 (4) | C14—N1—C3—C2 | 177.7 (2) |
N3—C1—C8—C9 | −8.0 (4) | C14—N1—C3—C4 | −0.2 (5) |
N3—C1—C8—C13 | 171.4 (2) | C14—C19—C18—C17 | −1.2 (7) |
N3—C2—C7—C6 | −177.5 (3) | C19—C14—C15—C16 | −1.3 (7) |
N3—C2—C3—N1 | −0.5 (4) | C19—C18—C17—C16 | −0.1 (8) |
N3—C2—C3—C4 | 177.5 (3) | C18—C17—C16—C15 | 0.7 (8) |
C1—N3—C2—C7 | 175.7 (2) | C17—C16—C15—C14 | 0.0 (7) |
C1—N3—C2—C3 | −2.6 (5) | C15—C14—C19—C18 | 1.9 (7) |
C1—C8—C9—C10 | 179.0 (3) | C8—C9—C10—C11 | 0.2 (5) |
C1—C8—C13—C12 | −178.9 (3) | C9—C8—C13—C12 | 0.6 (5) |
C2—N3—C1—N2 | 2.5 (4) | C9—C10—C11—C12 | 0.0 (5) |
C2—N3—C1—C8 | −176.9 (2) | C10—C11—C12—C13 | 0.1 (5) |
C2—C7—C6—C5 | −0.4 (6) | C11—C12—C13—C8 | −0.4 (5) |
C7—C2—C3—N1 | −178.8 (2) | C13—C8—C9—C10 | −0.5 (4) |
C7—C2—C3—C4 | −0.8 (4) |
C19H14N3 | F(000) = 596 |
Mr = 284.33 | Dx = 1.396 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.3807 (7) Å | Cell parameters from 2218 reflections |
b = 6.7430 (5) Å | θ = 3.2–24.6° |
c = 19.605 (3) Å | µ = 0.09 mm−1 |
β = 99.757 (8)° | T = 295 K |
V = 1352.5 (2) Å3 | Block, clear dark brown |
Z = 4 | 0.18 × 0.14 × 0.09 mm |
Bruker SMART APEX2 area detector diffractometer | 918 independent reflections |
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs | 604 reflections with I > 2σ(I) |
Mirror optics monochromator | Rint = 0.037 |
Detector resolution: 7.9 pixels mm-1 | θmax = 26.4°, θmin = 2.1° |
φ and ω scans | h = −12→12 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0633 before and 0.0418 after correction. The Ratio of minimum to maximum transmission is 0.9156. The λ/2 correction factor is Not present. | k = −8→8 |
Tmin = 0.683, Tmax = 0.745 | l = −8→8 |
6476 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.092 | w = 1/[σ2(Fo2) + (0.0507P)2 + 0.1489P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
918 reflections | Δρmax = 0.07 e Å−3 |
199 parameters | Δρmin = −0.11 e Å−3 |
231 restraints |
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. High pressure data collection in a diamond anvil cell. 0.6591 GPa. PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 231 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 80 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ··· 1 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 16 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 16 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info No action taken. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.4737 (2) | 0.7112 (3) | 0.6584 (3) | 0.037 (3) | |
N2 | 0.4422 (2) | 0.7061 (3) | 0.7229 (3) | 0.038 (3) | |
N3 | 0.2157 (2) | 0.6958 (3) | 0.6730 (3) | 0.036 (3) | |
C1 | 0.3137 (2) | 0.7002 (4) | 0.7260 (4) | 0.031 (3) | |
C2 | 0.2483 (3) | 0.6906 (4) | 0.6080 (4) | 0.033 (3) | |
C7 | 0.1520 (3) | 0.6729 (4) | 0.5504 (4) | 0.039 (3) | |
H7 | 0.064762 | 0.670168 | 0.555874 | 0.046* | |
C6 | 0.1826 (3) | 0.6594 (5) | 0.4857 (4) | 0.043 (3) | |
H6 | 0.115919 | 0.646329 | 0.447786 | 0.051* | |
C5 | 0.3126 (2) | 0.6649 (3) | 0.4754 (3) | 0.046 (3) | |
H5 | 0.332617 | 0.655638 | 0.431009 | 0.055* | |
C4 | 0.4102 (3) | 0.6843 (4) | 0.5317 (4) | 0.040 (3) | |
H4 | 0.496902 | 0.688652 | 0.525396 | 0.048* | |
C3 | 0.3808 (3) | 0.6973 (4) | 0.5979 (4) | 0.034 (3) | |
C14 | 0.61171 (19) | 0.7114 (3) | 0.6578 (3) | 0.031 (3) | |
C19 | 0.6658 (2) | 0.8517 (3) | 0.6206 (3) | 0.047 (4) | |
H19 | 0.613001 | 0.946961 | 0.595387 | 0.056* | |
C18 | 0.7989 (2) | 0.8511 (4) | 0.6207 (3) | 0.052 (4) | |
H18 | 0.835994 | 0.945196 | 0.595243 | 0.063* | |
C17 | 0.8761 (2) | 0.7115 (5) | 0.6584 (3) | 0.053 (4) | |
H17 | 0.965797 | 0.711476 | 0.658704 | 0.063* | |
C16 | 0.8220 (2) | 0.5719 (5) | 0.6957 (3) | 0.056 (4) | |
H16 | 0.874989 | 0.476887 | 0.720971 | 0.067* | |
C15 | 0.68818 (19) | 0.5718 (4) | 0.6960 (3) | 0.042 (3) | |
H15 | 0.651147 | 0.478406 | 0.721788 | 0.051* | |
C8 | 0.2828 (3) | 0.6974 (3) | 0.7971 (4) | 0.031 (3) | |
C9 | 0.1529 (2) | 0.7152 (4) | 0.8062 (4) | 0.042 (4) | |
H9 | 0.086930 | 0.730503 | 0.768095 | 0.050* | |
C10 | 0.1226 (3) | 0.7100 (4) | 0.8720 (4) | 0.047 (4) | |
H10 | 0.035895 | 0.721982 | 0.877911 | 0.056* | |
C11 | 0.2180 (3) | 0.6874 (3) | 0.9287 (4) | 0.052 (4) | |
H11 | 0.196370 | 0.683970 | 0.972798 | 0.062* | |
C12 | 0.3467 (3) | 0.6699 (4) | 0.9202 (4) | 0.046 (3) | |
H12 | 0.412006 | 0.654425 | 0.958584 | 0.055* | |
C13 | 0.3783 (3) | 0.6752 (4) | 0.8550 (4) | 0.040 (3) | |
H13 | 0.465318 | 0.663604 | 0.849718 | 0.048* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0231 (12) | 0.0470 (13) | 0.041 (9) | 0.0008 (9) | 0.007 (2) | 0.002 (2) |
N2 | 0.0253 (13) | 0.0445 (13) | 0.045 (9) | −0.0010 (9) | 0.009 (2) | −0.001 (2) |
N3 | 0.0264 (14) | 0.0391 (13) | 0.040 (9) | 0.0015 (9) | 0.001 (3) | 0.002 (2) |
C1 | 0.0252 (14) | 0.0279 (13) | 0.038 (9) | 0.0002 (10) | 0.002 (3) | −0.001 (3) |
C2 | 0.0292 (17) | 0.0331 (15) | 0.037 (9) | 0.0014 (10) | 0.005 (3) | −0.002 (3) |
C7 | 0.0253 (14) | 0.0493 (17) | 0.039 (10) | 0.0030 (11) | −0.002 (3) | 0.001 (3) |
C6 | 0.0381 (16) | 0.0513 (17) | 0.037 (10) | 0.0023 (12) | 0.002 (3) | −0.007 (3) |
C5 | 0.0375 (14) | 0.0551 (16) | 0.043 (10) | 0.0026 (11) | 0.003 (3) | 0.004 (3) |
C4 | 0.0317 (16) | 0.0490 (17) | 0.040 (10) | 0.0023 (12) | 0.009 (3) | 0.003 (3) |
C3 | 0.0277 (15) | 0.0324 (14) | 0.041 (9) | 0.0014 (10) | 0.004 (3) | −0.002 (3) |
C14 | 0.0233 (11) | 0.0436 (14) | 0.025 (10) | 0.0003 (10) | 0.004 (2) | −0.005 (2) |
C19 | 0.0334 (12) | 0.0480 (17) | 0.058 (12) | −0.0031 (10) | 0.004 (3) | 0.003 (2) |
C18 | 0.0361 (14) | 0.079 (2) | 0.044 (13) | −0.0166 (12) | 0.012 (3) | −0.001 (3) |
C17 | 0.0260 (12) | 0.104 (3) | 0.027 (13) | −0.0001 (14) | 0.003 (3) | −0.011 (3) |
C16 | 0.0357 (13) | 0.092 (2) | 0.037 (13) | 0.0166 (13) | −0.003 (3) | 0.009 (3) |
C15 | 0.0357 (12) | 0.0572 (17) | 0.035 (11) | 0.0034 (10) | 0.010 (2) | 0.004 (2) |
C8 | 0.0295 (15) | 0.0287 (14) | 0.037 (9) | −0.0019 (10) | 0.008 (3) | −0.001 (3) |
C9 | 0.0290 (15) | 0.0419 (15) | 0.055 (11) | −0.0023 (10) | 0.006 (3) | 0.001 (3) |
C10 | 0.0364 (16) | 0.0472 (16) | 0.061 (11) | −0.0053 (12) | 0.019 (3) | −0.002 (3) |
C11 | 0.0519 (17) | 0.0476 (17) | 0.059 (12) | −0.0070 (12) | 0.018 (3) | −0.003 (3) |
C12 | 0.0464 (18) | 0.0528 (18) | 0.036 (11) | −0.0027 (13) | 0.001 (3) | −0.003 (3) |
C13 | 0.0301 (15) | 0.0483 (17) | 0.041 (10) | −0.0011 (12) | 0.003 (3) | −0.006 (3) |
N1—N2 | 1.358 (7) | C19—C18 | 1.382 (3) |
N1—C3 | 1.399 (7) | C18—H18 | 0.9300 |
N1—C14 | 1.435 (3) | C18—C17 | 1.369 (5) |
N2—C1 | 1.346 (4) | C17—H17 | 0.9300 |
N3—C1 | 1.325 (6) | C17—C16 | 1.370 (5) |
N3—C2 | 1.373 (7) | C16—H16 | 0.9300 |
C1—C8 | 1.483 (7) | C16—C15 | 1.390 (3) |
C2—C7 | 1.381 (7) | C15—H15 | 0.9300 |
C2—C3 | 1.423 (5) | C8—C9 | 1.396 (4) |
C7—H7 | 0.9300 | C8—C13 | 1.383 (7) |
C7—C6 | 1.361 (8) | C9—H9 | 0.9300 |
C6—H6 | 0.9300 | C9—C10 | 1.379 (8) |
C6—C5 | 1.399 (4) | C10—H10 | 0.9300 |
C5—H5 | 0.9300 | C10—C11 | 1.366 (7) |
C5—C4 | 1.373 (6) | C11—H11 | 0.9300 |
C4—H4 | 0.9300 | C11—C12 | 1.378 (4) |
C4—C3 | 1.385 (8) | C12—H12 | 0.9300 |
C14—C19 | 1.371 (5) | C12—C13 | 1.372 (8) |
C14—C15 | 1.370 (4) | C13—H13 | 0.9300 |
C19—H19 | 0.9300 | ||
N2—N1—C3 | 123.2 (3) | C18—C19—H19 | 120.1 |
N2—N1—C14 | 113.9 (5) | C19—C18—H18 | 120.1 |
C3—N1—C14 | 122.6 (5) | C17—C18—C19 | 119.8 (3) |
C1—N2—N1 | 116.0 (5) | C17—C18—H18 | 120.1 |
C1—N3—C2 | 116.8 (4) | C18—C17—H17 | 119.8 |
N2—C1—C8 | 114.6 (5) | C18—C17—C16 | 120.4 (3) |
N3—C1—N2 | 126.9 (6) | C16—C17—H17 | 119.8 |
N3—C1—C8 | 118.5 (3) | C17—C16—H16 | 119.9 |
N3—C2—C7 | 120.2 (4) | C17—C16—C15 | 120.2 (3) |
N3—C2—C3 | 121.6 (5) | C15—C16—H16 | 119.9 |
C7—C2—C3 | 118.2 (6) | C14—C15—C16 | 119.0 (3) |
C2—C7—H7 | 119.4 | C14—C15—H15 | 120.5 |
C6—C7—C2 | 121.1 (4) | C16—C15—H15 | 120.5 |
C6—C7—H7 | 119.4 | C9—C8—C1 | 119.2 (5) |
C7—C6—H6 | 119.5 | C13—C8—C1 | 122.3 (3) |
C7—C6—C5 | 121.1 (5) | C13—C8—C9 | 118.5 (6) |
C5—C6—H6 | 119.5 | C8—C9—H9 | 120.1 |
C6—C5—H5 | 120.5 | C10—C9—C8 | 119.8 (5) |
C4—C5—C6 | 119.0 (5) | C10—C9—H9 | 120.1 |
C4—C5—H5 | 120.5 | C9—C10—H10 | 119.5 |
C5—C4—H4 | 119.6 | C11—C10—C9 | 121.0 (3) |
C5—C4—C3 | 120.7 (3) | C11—C10—H10 | 119.5 |
C3—C4—H4 | 119.6 | C10—C11—H11 | 120.2 |
N1—C3—C2 | 115.3 (6) | C10—C11—C12 | 119.7 (6) |
C4—C3—N1 | 124.7 (3) | C12—C11—H11 | 120.2 |
C4—C3—C2 | 119.9 (5) | C11—C12—H12 | 120.0 |
C19—C14—N1 | 120.3 (3) | C13—C12—C11 | 120.0 (6) |
C15—C14—N1 | 118.8 (3) | C13—C12—H12 | 120.0 |
C15—C14—C19 | 120.9 (2) | C8—C13—H13 | 119.5 |
C14—C19—H19 | 120.1 | C12—C13—C8 | 121.1 (4) |
C14—C19—C18 | 119.8 (3) | C12—C13—H13 | 119.5 |
N1—N2—C1—N3 | 1.1 (4) | C7—C6—C5—C4 | 0.0 (5) |
N1—N2—C1—C8 | −179.2 (2) | C6—C5—C4—C3 | 0.3 (4) |
N1—C14—C19—C18 | 179.6 (5) | C5—C4—C3—N1 | 178.0 (2) |
N1—C14—C15—C16 | −179.8 (4) | C5—C4—C3—C2 | 0.0 (5) |
N2—N1—C3—C2 | 4.0 (4) | C3—N1—N2—C1 | −4.4 (4) |
N2—N1—C3—C4 | −174.0 (3) | C3—N1—C14—C19 | 57.5 (5) |
N2—N1—C14—C19 | −128.6 (4) | C3—N1—C14—C15 | −123.8 (4) |
N2—N1—C14—C15 | 50.1 (5) | C3—C2—C7—C6 | 0.9 (5) |
N2—C1—C8—C9 | 172.4 (2) | C14—N1—N2—C1 | −178.26 (18) |
N2—C1—C8—C13 | −8.4 (4) | C14—N1—C3—C2 | 177.4 (2) |
N3—C1—C8—C9 | −7.9 (4) | C14—N1—C3—C4 | −0.6 (5) |
N3—C1—C8—C13 | 171.2 (2) | C14—C19—C18—C17 | −0.6 (7) |
N3—C2—C7—C6 | −177.3 (3) | C19—C14—C15—C16 | −1.1 (7) |
N3—C2—C3—N1 | −0.5 (4) | C19—C18—C17—C16 | 0.3 (7) |
N3—C2—C3—C4 | 177.6 (3) | C18—C17—C16—C15 | −0.5 (8) |
C1—N3—C2—C7 | 175.8 (2) | C17—C16—C15—C14 | 0.9 (7) |
C1—N3—C2—C3 | −2.3 (4) | C15—C14—C19—C18 | 1.0 (7) |
C1—C8—C9—C10 | 179.1 (3) | C8—C9—C10—C11 | 0.0 (5) |
C1—C8—C13—C12 | −178.9 (3) | C9—C8—C13—C12 | 0.2 (5) |
C2—N3—C1—N2 | 2.1 (4) | C9—C10—C11—C12 | 0.1 (5) |
C2—N3—C1—C8 | −177.5 (2) | C10—C11—C12—C13 | 0.0 (5) |
C2—C7—C6—C5 | −0.6 (5) | C11—C12—C13—C8 | −0.2 (5) |
C7—C2—C3—N1 | −178.7 (2) | C13—C8—C9—C10 | −0.1 (4) |
C7—C2—C3—C4 | −0.6 (4) |
C19H14N3 | F(000) = 596 |
Mr = 284.33 | Dx = 1.437 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.3374 (18) Å | Cell parameters from 1054 reflections |
b = 6.629 (3) Å | θ = 3.5–23.9° |
c = 19.466 (4) Å | µ = 0.09 mm−1 |
β = 99.780 (8)° | T = 300 K |
V = 1314.5 (6) Å3 | Block, clear dark brown |
Z = 4 | 0.16 × 0.14 × 0.09 mm |
Bruker SMART APEX2 area detector diffractometer | 846 independent reflections |
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs | 479 reflections with I > 2σ(I) |
Mirror optics monochromator | Rint = 0.072 |
Detector resolution: 7.9 pixels mm-1 | θmax = 26.2°, θmin = 2.1° |
ω and φ scans | h = −12→12 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1200 before and 0.0476 after correction. The Ratio of minimum to maximum transmission is 0.8464. The λ/2 correction factor is Not present. | k = −2→2 |
Tmin = 0.631, Tmax = 0.745 | l = −22→23 |
4283 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.109 | w = 1/[σ2(Fo2) + (0.0553P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
846 reflections | Δρmax = 0.14 e Å−3 |
194 parameters | Δρmin = −0.14 e Å−3 |
249 restraints |
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. High pressure data collection in a diamond anvil cell. 0.8792 GPa. PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ··· 6 Report PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records 1 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 249 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 65 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ··· 9 Note PLAT951_ALERT_5_G Calculated (ThMax) and CIF-Reported Kmax Differ 6 Units PLAT957_ALERT_1_G Calculated (ThMax) and Actual (FCF) Kmax Differ 6 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info No action taken. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.4734 (2) | 0.7083 (12) | 0.65824 (14) | 0.036 (4) | |
N2 | 0.4422 (2) | 0.7033 (11) | 0.72398 (13) | 0.032 (5) | |
N3 | 0.2145 (2) | 0.6922 (13) | 0.67380 (14) | 0.055 (6) | |
C1 | 0.3139 (3) | 0.6983 (14) | 0.72633 (17) | 0.035 (6) | |
C2 | 0.2476 (3) | 0.6885 (15) | 0.60787 (17) | 0.027 (6) | |
C7 | 0.1512 (3) | 0.6700 (16) | 0.54981 (18) | 0.043 (6) | |
H7 | 0.063781 | 0.664927 | 0.555527 | 0.052* | |
C6 | 0.1808 (3) | 0.6588 (15) | 0.48406 (19) | 0.038 (6) | |
H6 | 0.114319 | 0.647931 | 0.445543 | 0.046* | |
C5 | 0.3117 (3) | 0.6640 (15) | 0.47556 (18) | 0.053 (6) | |
H5 | 0.332531 | 0.651830 | 0.431112 | 0.063* | |
C4 | 0.4102 (3) | 0.6867 (15) | 0.53150 (17) | 0.040 (6) | |
H4 | 0.496965 | 0.695513 | 0.524831 | 0.048* | |
C3 | 0.3802 (3) | 0.6967 (15) | 0.59848 (18) | 0.023 (6) | |
C14 | 0.6129 (3) | 0.7091 (12) | 0.65846 (19) | 0.037 (4) | |
C19 | 0.6664 (3) | 0.8514 (13) | 0.62066 (18) | 0.044 (4) | |
H19 | 0.613362 | 0.947603 | 0.594959 | 0.052* | |
C18 | 0.8008 (3) | 0.8502 (14) | 0.62117 (19) | 0.050 (4) | |
H18 | 0.838079 | 0.947232 | 0.596076 | 0.061* | |
C17 | 0.8783 (3) | 0.7082 (13) | 0.6581 (2) | 0.052 (4) | |
H17 | 0.968160 | 0.707166 | 0.657685 | 0.063* | |
C16 | 0.8236 (3) | 0.5653 (14) | 0.69633 (19) | 0.055 (5) | |
H16 | 0.876413 | 0.468576 | 0.721900 | 0.066* | |
C15 | 0.6887 (3) | 0.5673 (14) | 0.69628 (19) | 0.044 (4) | |
H15 | 0.651014 | 0.472242 | 0.721941 | 0.053* | |
C8 | 0.2824 (3) | 0.6925 (15) | 0.79815 (17) | 0.024 (5) | |
C9 | 0.1516 (3) | 0.7109 (16) | 0.80715 (18) | 0.0324 (10)* | |
H9 | 0.085238 | 0.724259 | 0.768663 | 0.039* | |
C10 | 0.1215 (3) | 0.7091 (18) | 0.87400 (18) | 0.040 (6) | |
H10 | 0.034833 | 0.725103 | 0.880177 | 0.047* | |
C11 | 0.2173 (3) | 0.6842 (17) | 0.9305 (2) | 0.043 (6) | |
H11 | 0.195668 | 0.679634 | 0.974985 | 0.052* | |
C12 | 0.3467 (3) | 0.6655 (18) | 0.92196 (19) | 0.042 (6) | |
H12 | 0.412280 | 0.648713 | 0.960608 | 0.050* | |
C13 | 0.3785 (3) | 0.6720 (15) | 0.85601 (18) | 0.027 (5) | |
H13 | 0.465933 | 0.662324 | 0.850567 | 0.033* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0232 (12) | 0.057 (14) | 0.0271 (19) | 0.000 (2) | 0.0039 (13) | 0.002 (3) |
N2 | 0.0290 (13) | 0.042 (15) | 0.0274 (19) | −0.002 (2) | 0.0069 (13) | 0.000 (3) |
N3 | 0.0281 (13) | 0.114 (18) | 0.0242 (19) | 0.001 (3) | 0.0032 (13) | 0.000 (3) |
C1 | 0.0271 (15) | 0.047 (19) | 0.029 (2) | 0.002 (3) | 0.0003 (16) | −0.002 (4) |
C2 | 0.0314 (17) | 0.02 (2) | 0.031 (2) | 0.002 (3) | 0.0048 (17) | 0.009 (4) |
C7 | 0.0247 (15) | 0.07 (2) | 0.035 (2) | 0.002 (3) | 0.0001 (16) | 0.005 (4) |
C6 | 0.0384 (17) | 0.041 (19) | 0.033 (2) | −0.006 (3) | 0.0007 (18) | −0.001 (4) |
C5 | 0.0425 (17) | 0.09 (2) | 0.026 (2) | 0.005 (3) | 0.0053 (17) | 0.005 (4) |
C4 | 0.0318 (16) | 0.06 (2) | 0.032 (2) | 0.004 (3) | 0.0070 (17) | 0.001 (4) |
C3 | 0.0267 (15) | 0.01 (2) | 0.035 (2) | −0.001 (3) | 0.0047 (16) | −0.001 (4) |
C14 | 0.0250 (15) | 0.063 (13) | 0.024 (2) | 0.004 (3) | 0.0052 (17) | −0.001 (4) |
C19 | 0.0337 (16) | 0.062 (14) | 0.035 (3) | 0.001 (3) | 0.0074 (18) | 0.000 (4) |
C18 | 0.0338 (17) | 0.084 (14) | 0.035 (3) | −0.013 (3) | 0.010 (2) | −0.004 (4) |
C17 | 0.0244 (15) | 0.099 (14) | 0.034 (3) | 0.002 (3) | 0.0074 (18) | −0.004 (4) |
C16 | 0.0341 (17) | 0.093 (14) | 0.037 (3) | 0.016 (3) | 0.0045 (18) | 0.009 (4) |
C15 | 0.0357 (17) | 0.070 (14) | 0.027 (3) | 0.006 (3) | 0.005 (2) | 0.006 (4) |
C8 | 0.0310 (16) | 0.008 (16) | 0.034 (2) | −0.004 (3) | 0.0084 (16) | −0.006 (4) |
C10 | 0.0366 (17) | 0.043 (19) | 0.043 (3) | −0.008 (4) | 0.0164 (18) | −0.010 (4) |
C11 | 0.0537 (19) | 0.04 (2) | 0.035 (3) | −0.008 (4) | 0.0156 (18) | −0.007 (4) |
C12 | 0.0439 (18) | 0.043 (19) | 0.037 (3) | −0.003 (4) | 0.0043 (18) | −0.002 (4) |
C13 | 0.0298 (16) | 0.015 (16) | 0.037 (2) | 0.005 (3) | 0.0045 (16) | 0.002 (4) |
N1—N2 | 1.373 (3) | C19—C18 | 1.387 (4) |
N1—C3 | 1.381 (4) | C18—H18 | 0.9300 |
N1—C14 | 1.441 (3) | C18—C17 | 1.360 (7) |
N2—C1 | 1.335 (3) | C17—H17 | 0.9300 |
N3—C1 | 1.321 (4) | C17—C16 | 1.383 (7) |
N3—C2 | 1.383 (4) | C16—H16 | 0.9300 |
C1—C8 | 1.488 (4) | C16—C15 | 1.394 (4) |
C2—C7 | 1.379 (4) | C15—H15 | 0.9300 |
C2—C3 | 1.414 (4) | C8—C9 | 1.399 (4) |
C7—H7 | 0.9300 | C8—C13 | 1.376 (4) |
C7—C6 | 1.367 (4) | C9—H9 | 0.9300 |
C6—H6 | 0.9300 | C9—C10 | 1.388 (4) |
C6—C5 | 1.391 (4) | C10—H10 | 0.9300 |
C5—H5 | 0.9300 | C10—C11 | 1.360 (5) |
C5—C4 | 1.367 (4) | C11—H11 | 0.9300 |
C4—H4 | 0.9300 | C11—C12 | 1.382 (4) |
C4—C3 | 1.392 (4) | C12—H12 | 0.9300 |
C14—C19 | 1.369 (7) | C12—C13 | 1.379 (4) |
C14—C15 | 1.358 (7) | C13—H13 | 0.9300 |
C19—H19 | 0.9300 | ||
N2—N1—C3 | 122.9 (2) | C18—C19—H19 | 120.4 |
N2—N1—C14 | 113.0 (3) | C19—C18—H18 | 119.8 |
C3—N1—C14 | 123.9 (2) | C17—C18—C19 | 120.5 (5) |
C1—N2—N1 | 115.2 (3) | C17—C18—H18 | 119.8 |
C1—N3—C2 | 115.9 (2) | C18—C17—H17 | 120.0 |
N2—C1—C8 | 114.2 (3) | C18—C17—C16 | 120.0 (3) |
N3—C1—N2 | 128.3 (3) | C16—C17—H17 | 120.0 |
N3—C1—C8 | 117.5 (2) | C17—C16—H16 | 120.2 |
N3—C2—C3 | 121.1 (3) | C17—C16—C15 | 119.6 (5) |
C7—C2—N3 | 120.3 (2) | C15—C16—H16 | 120.2 |
C7—C2—C3 | 118.6 (3) | C14—C15—C16 | 119.5 (5) |
C2—C7—H7 | 119.1 | C14—C15—H15 | 120.3 |
C6—C7—C2 | 121.8 (3) | C16—C15—H15 | 120.3 |
C6—C7—H7 | 119.1 | C9—C8—C1 | 119.0 (3) |
C7—C6—H6 | 120.4 | C13—C8—C1 | 121.9 (2) |
C7—C6—C5 | 119.1 (3) | C13—C8—C9 | 119.0 (3) |
C5—C6—H6 | 120.4 | C8—C9—H9 | 120.3 |
C6—C5—H5 | 119.5 | C10—C9—C8 | 119.5 (3) |
C4—C5—C6 | 121.0 (3) | C10—C9—H9 | 120.3 |
C4—C5—H5 | 119.5 | C9—C10—H10 | 119.6 |
C5—C4—H4 | 120.1 | C11—C10—C9 | 120.8 (3) |
C5—C4—C3 | 119.8 (3) | C11—C10—H10 | 119.6 |
C3—C4—H4 | 120.1 | C10—C11—H11 | 120.0 |
N1—C3—C2 | 116.5 (3) | C10—C11—C12 | 120.0 (3) |
N1—C3—C4 | 123.8 (2) | C12—C11—H11 | 120.0 |
C4—C3—C2 | 119.6 (3) | C11—C12—H12 | 120.0 |
C19—C14—N1 | 119.8 (5) | C13—C12—C11 | 119.9 (4) |
C15—C14—N1 | 119.0 (5) | C13—C12—H12 | 120.0 |
C15—C14—C19 | 121.3 (3) | C8—C13—C12 | 120.8 (3) |
C14—C19—H19 | 120.4 | C8—C13—H13 | 119.6 |
C14—C19—C18 | 119.2 (5) | C12—C13—H13 | 119.6 |
N1—N2—C1—N3 | 1.9 (12) | C7—C6—C5—C4 | −2.2 (13) |
N1—N2—C1—C8 | 179.8 (9) | C6—C5—C4—C3 | 2.6 (14) |
N1—C14—C19—C18 | −179.8 (5) | C5—C4—C3—N1 | 176.3 (9) |
N1—C14—C15—C16 | 179.4 (5) | C5—C4—C3—C2 | −1.6 (15) |
N2—N1—C3—C2 | 2.8 (13) | C3—N1—N2—C1 | −3.7 (11) |
N2—N1—C3—C4 | −175.2 (9) | C3—N1—C14—C19 | 56.0 (10) |
N2—N1—C14—C19 | −129.1 (6) | C3—N1—C14—C15 | −123.8 (8) |
N2—N1—C14—C15 | 51.1 (9) | C3—C2—C7—C6 | 0.2 (14) |
N2—C1—C8—C9 | 172.5 (7) | C14—N1—N2—C1 | −178.7 (6) |
N2—C1—C8—C13 | −6.7 (12) | C14—N1—C3—C2 | 177.2 (8) |
N3—C1—C8—C9 | −9.3 (15) | C14—N1—C3—C4 | −0.7 (14) |
N3—C1—C8—C13 | 171.5 (7) | C14—C19—C18—C17 | 0.7 (8) |
N3—C2—C7—C6 | −177.7 (10) | C19—C14—C15—C16 | −0.4 (9) |
N3—C2—C3—N1 | 0.1 (14) | C19—C18—C17—C16 | −0.9 (8) |
N3—C2—C3—C4 | 178.1 (10) | C18—C17—C16—C15 | 0.4 (8) |
C1—N3—C2—C7 | 176.1 (9) | C17—C16—C15—C14 | 0.3 (9) |
C1—N3—C2—C3 | −1.7 (13) | C15—C14—C19—C18 | 0.0 (8) |
C1—C8—C9—C10 | −178.9 (11) | C8—C9—C10—C11 | −1.8 (16) |
C1—C8—C13—C12 | −179.5 (11) | C9—C8—C13—C12 | 1.3 (14) |
C2—N3—C1—N2 | 0.7 (13) | C9—C10—C11—C12 | 1.7 (16) |
C2—N3—C1—C8 | −177.1 (9) | C10—C11—C12—C13 | −0.1 (16) |
C2—C7—C6—C5 | 0.7 (14) | C11—C12—C13—C8 | −1.4 (15) |
C7—C2—C3—N1 | −177.8 (8) | C13—C8—C9—C10 | 0.3 (15) |
C7—C2—C3—C4 | 0.2 (14) |
C19H14N3 | F(000) = 596 |
Mr = 284.33 | Dx = 1.456 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.3045 (6) Å | Cell parameters from 2249 reflections |
b = 6.5805 (4) Å | θ = 3.3–24.1° |
c = 19.408 (2) Å | µ = 0.09 mm−1 |
β = 99.823 (6)° | T = 271 K |
V = 1296.7 (2) Å3 | Block, clear dark brown |
Z = 4 | 0.18 × 0.14 × 0.09 mm |
Bruker SMART APEX2 area detector diffractometer | 888 independent reflections |
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs | 613 reflections with I > 2σ(I) |
Mirror optics monochromator | Rint = 0.038 |
Detector resolution: 7.9 pixels mm-1 | θmax = 26.4°, θmin = 2.1° |
ω and φ scans | h = −12→12 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0580 before and 0.0448 after correction. The Ratio of minimum to maximum transmission is 0.8904. The λ/2 correction factor is Not present. | k = −8→8 |
Tmin = 0.664, Tmax = 0.745 | l = −8→8 |
7436 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.032 | H-atom parameters constrained |
wR(F2) = 0.085 | w = 1/[σ2(Fo2) + (0.0503P)2 + 0.1084P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
888 reflections | Δρmax = 0.08 e Å−3 |
199 parameters | Δρmin = −0.07 e Å−3 |
231 restraints |
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. High pressure data collection in a diamond anvil cell. 1.0994 GPa. PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT152_ALERT_1_G The Supplied and Calc. Volume s.u. Differ by ··· -3 Units PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 231 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 59 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 16 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 16 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info No action taken. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.4740 (2) | 0.7069 (3) | 0.6589 (3) | 0.030 (3) | |
N2 | 0.4428 (2) | 0.7000 (3) | 0.7241 (3) | 0.030 (3) | |
N3 | 0.2143 (2) | 0.6894 (3) | 0.6739 (3) | 0.031 (3) | |
C1 | 0.3133 (3) | 0.6938 (3) | 0.7270 (4) | 0.026 (3) | |
C2 | 0.2466 (3) | 0.6863 (4) | 0.6083 (4) | 0.028 (3) | |
C7 | 0.1497 (3) | 0.6684 (4) | 0.5500 (4) | 0.032 (3) | |
H7 | 0.061914 | 0.662853 | 0.555599 | 0.038* | |
C6 | 0.1801 (3) | 0.6586 (4) | 0.4844 (4) | 0.035 (3) | |
H6 | 0.112831 | 0.646908 | 0.445993 | 0.042* | |
C5 | 0.3113 (2) | 0.6660 (3) | 0.4741 (3) | 0.036 (3) | |
H5 | 0.331602 | 0.658534 | 0.429327 | 0.043* | |
C4 | 0.4099 (3) | 0.6845 (4) | 0.5316 (4) | 0.031 (3) | |
H4 | 0.497389 | 0.689566 | 0.525467 | 0.037* | |
C3 | 0.3797 (3) | 0.6954 (4) | 0.5980 (4) | 0.028 (3) | |
C14 | 0.61292 (18) | 0.7075 (3) | 0.6582 (3) | 0.022 (3) | |
C19 | 0.66735 (19) | 0.8528 (3) | 0.6210 (3) | 0.033 (3) | |
H19 | 0.614204 | 0.950976 | 0.595791 | 0.039* | |
C18 | 0.8011 (2) | 0.8521 (4) | 0.6212 (3) | 0.041 (4) | |
H18 | 0.838283 | 0.949621 | 0.595847 | 0.049* | |
C17 | 0.8788 (2) | 0.7093 (4) | 0.6583 (3) | 0.045 (4) | |
H17 | 0.968914 | 0.709068 | 0.657914 | 0.054* | |
C16 | 0.8253 (2) | 0.5650 (4) | 0.6965 (3) | 0.045 (4) | |
H16 | 0.879261 | 0.468329 | 0.721968 | 0.054* | |
C15 | 0.69047 (18) | 0.5641 (3) | 0.6968 (3) | 0.035 (3) | |
H15 | 0.653430 | 0.467988 | 0.722729 | 0.042* | |
C8 | 0.2826 (3) | 0.6910 (3) | 0.7990 (4) | 0.027 (3) | |
C9 | 0.1512 (2) | 0.7100 (3) | 0.8079 (3) | 0.037 (3) | |
H9 | 0.084966 | 0.725356 | 0.769213 | 0.045* | |
C10 | 0.1206 (3) | 0.7060 (4) | 0.8740 (3) | 0.041 (3) | |
H10 | 0.033186 | 0.718362 | 0.879708 | 0.049* | |
C11 | 0.2169 (3) | 0.6840 (3) | 0.9319 (3) | 0.042 (3) | |
H11 | 0.194892 | 0.681407 | 0.976377 | 0.050* | |
C12 | 0.3467 (3) | 0.6657 (4) | 0.9233 (4) | 0.040 (3) | |
H12 | 0.412673 | 0.650621 | 0.962171 | 0.048* | |
C13 | 0.3782 (3) | 0.6700 (4) | 0.8573 (4) | 0.033 (3) | |
H13 | 0.465876 | 0.658484 | 0.851936 | 0.040* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0211 (13) | 0.0382 (11) | 0.034 (9) | −0.0002 (8) | 0.011 (2) | 0.001 (2) |
N2 | 0.0186 (13) | 0.0372 (10) | 0.033 (9) | −0.0017 (7) | 0.005 (2) | −0.001 (2) |
N3 | 0.0220 (14) | 0.0330 (10) | 0.036 (9) | 0.0017 (8) | −0.002 (3) | 0.001 (2) |
C1 | 0.0219 (15) | 0.0213 (11) | 0.034 (9) | −0.0003 (9) | 0.003 (3) | 0.002 (2) |
C2 | 0.0242 (17) | 0.0253 (11) | 0.035 (9) | 0.0002 (9) | 0.005 (3) | −0.001 (3) |
C7 | 0.0193 (14) | 0.0381 (13) | 0.035 (10) | 0.0005 (10) | −0.002 (3) | 0.003 (3) |
C6 | 0.0312 (16) | 0.0394 (13) | 0.034 (10) | 0.0018 (10) | 0.001 (3) | 0.000 (3) |
C5 | 0.0340 (15) | 0.0428 (13) | 0.030 (10) | 0.0028 (10) | 0.005 (3) | 0.000 (2) |
C4 | 0.0238 (15) | 0.0391 (13) | 0.030 (9) | 0.0014 (10) | 0.005 (3) | −0.001 (3) |
C3 | 0.0228 (16) | 0.0275 (11) | 0.035 (9) | 0.0012 (9) | 0.004 (3) | −0.004 (2) |
C14 | 0.0184 (10) | 0.0345 (11) | 0.013 (9) | −0.0001 (8) | 0.003 (2) | −0.0035 (17) |
C19 | 0.0283 (12) | 0.0415 (13) | 0.028 (11) | −0.0013 (9) | 0.003 (2) | −0.0020 (19) |
C18 | 0.0285 (13) | 0.0650 (16) | 0.031 (12) | −0.0139 (10) | 0.008 (2) | −0.002 (2) |
C17 | 0.0203 (12) | 0.089 (2) | 0.027 (12) | 0.0004 (12) | 0.004 (2) | −0.003 (3) |
C16 | 0.0316 (13) | 0.0745 (18) | 0.026 (12) | 0.0164 (12) | −0.004 (3) | 0.001 (3) |
C15 | 0.0305 (12) | 0.0502 (14) | 0.025 (10) | 0.0038 (9) | 0.007 (2) | 0.004 (2) |
C8 | 0.0230 (15) | 0.0243 (11) | 0.034 (9) | −0.0004 (9) | 0.005 (3) | −0.001 (2) |
C9 | 0.0248 (15) | 0.0333 (12) | 0.054 (10) | −0.0031 (9) | 0.007 (3) | 0.004 (3) |
C10 | 0.0280 (15) | 0.0390 (13) | 0.059 (11) | −0.0044 (10) | 0.015 (3) | 0.001 (2) |
C11 | 0.0446 (16) | 0.0373 (13) | 0.048 (11) | −0.0054 (10) | 0.019 (3) | −0.001 (2) |
C12 | 0.0401 (18) | 0.0399 (14) | 0.039 (10) | −0.0038 (11) | 0.004 (3) | −0.003 (3) |
C13 | 0.0228 (15) | 0.0369 (13) | 0.038 (10) | 0.0001 (10) | 0.001 (3) | −0.002 (3) |
N1—N2 | 1.358 (7) | C19—C18 | 1.377 (3) |
N1—C3 | 1.398 (7) | C18—H18 | 0.9300 |
N1—C14 | 1.434 (3) | C18—C17 | 1.359 (5) |
N2—C1 | 1.346 (3) | C17—H17 | 0.9300 |
N3—C1 | 1.321 (6) | C17—C16 | 1.375 (5) |
N3—C2 | 1.369 (7) | C16—H16 | 0.9300 |
C1—C8 | 1.486 (7) | C16—C15 | 1.391 (3) |
C2—C7 | 1.380 (7) | C15—H15 | 0.9300 |
C2—C3 | 1.421 (5) | C8—C9 | 1.399 (4) |
C7—H7 | 0.9300 | C8—C13 | 1.374 (7) |
C7—C6 | 1.364 (8) | C9—H9 | 0.9300 |
C6—H6 | 0.9300 | C9—C10 | 1.372 (7) |
C6—C5 | 1.401 (4) | C10—H10 | 0.9300 |
C5—H5 | 0.9300 | C10—C11 | 1.374 (7) |
C5—C4 | 1.380 (6) | C11—H11 | 0.9300 |
C4—H4 | 0.9300 | C11—C12 | 1.380 (4) |
C4—C3 | 1.378 (7) | C12—H12 | 0.9300 |
C14—C19 | 1.374 (4) | C12—C13 | 1.376 (8) |
C14—C15 | 1.373 (4) | C13—H13 | 0.9300 |
C19—H19 | 0.9300 | ||
N2—N1—C3 | 123.0 (3) | C18—C19—H19 | 120.2 |
N2—N1—C14 | 113.8 (5) | C19—C18—H18 | 119.9 |
C3—N1—C14 | 122.9 (5) | C17—C18—C19 | 120.2 (3) |
C1—N2—N1 | 115.7 (5) | C17—C18—H18 | 119.9 |
C1—N3—C2 | 116.6 (4) | C18—C17—H17 | 119.7 |
N2—C1—C8 | 114.3 (5) | C18—C17—C16 | 120.6 (2) |
N3—C1—N2 | 127.4 (6) | C16—C17—H17 | 119.7 |
N3—C1—C8 | 118.3 (3) | C17—C16—H16 | 120.1 |
N3—C2—C7 | 120.4 (3) | C17—C16—C15 | 119.8 (3) |
N3—C2—C3 | 121.6 (5) | C15—C16—H16 | 120.1 |
C7—C2—C3 | 117.9 (6) | C14—C15—C16 | 118.9 (3) |
C2—C7—H7 | 119.3 | C14—C15—H15 | 120.5 |
C6—C7—C2 | 121.4 (4) | C16—C15—H15 | 120.5 |
C6—C7—H7 | 119.3 | C9—C8—C1 | 118.7 (5) |
C7—C6—H6 | 119.6 | C13—C8—C1 | 122.5 (3) |
C7—C6—C5 | 120.8 (5) | C13—C8—C9 | 118.8 (6) |
C5—C6—H6 | 119.6 | C8—C9—H9 | 120.2 |
C6—C5—H5 | 120.5 | C10—C9—C8 | 119.6 (5) |
C4—C5—C6 | 118.9 (5) | C10—C9—H9 | 120.2 |
C4—C5—H5 | 120.5 | C9—C10—H10 | 119.4 |
C5—C4—H4 | 119.8 | C9—C10—C11 | 121.2 (3) |
C3—C4—C5 | 120.5 (3) | C11—C10—H10 | 119.4 |
C3—C4—H4 | 119.8 | C10—C11—H11 | 120.3 |
N1—C3—C2 | 115.5 (6) | C10—C11—C12 | 119.4 (5) |
C4—C3—N1 | 123.9 (3) | C12—C11—H11 | 120.3 |
C4—C3—C2 | 120.5 (5) | C11—C12—H12 | 120.1 |
C19—C14—N1 | 120.3 (3) | C13—C12—C11 | 119.8 (5) |
C15—C14—N1 | 118.8 (3) | C13—C12—H12 | 120.1 |
C15—C14—C19 | 120.86 (19) | C8—C13—C12 | 121.3 (4) |
C14—C19—H19 | 120.2 | C8—C13—H13 | 119.4 |
C14—C19—C18 | 119.6 (3) | C12—C13—H13 | 119.4 |
N1—N2—C1—N3 | 1.5 (4) | C7—C6—C5—C4 | −0.4 (4) |
N1—N2—C1—C8 | −178.7 (2) | C6—C5—C4—C3 | 0.0 (4) |
N1—C14—C19—C18 | 179.6 (4) | C5—C4—C3—N1 | 177.62 (18) |
N1—C14—C15—C16 | −179.7 (4) | C5—C4—C3—C2 | 0.5 (4) |
N2—N1—C3—C2 | 3.1 (3) | C3—N1—N2—C1 | −3.9 (4) |
N2—N1—C3—C4 | −174.2 (3) | C3—N1—C14—C19 | 57.1 (4) |
N2—N1—C14—C19 | −128.5 (4) | C3—N1—C14—C15 | −124.6 (4) |
N2—N1—C14—C15 | 49.8 (4) | C3—C2—C7—C6 | 0.3 (4) |
N2—C1—C8—C9 | 172.14 (18) | C14—N1—N2—C1 | −178.30 (16) |
N2—C1—C8—C13 | −8.0 (4) | C14—N1—C3—C2 | 176.96 (19) |
N3—C1—C8—C9 | −8.1 (3) | C14—N1—C3—C4 | −0.3 (4) |
N3—C1—C8—C13 | 171.82 (19) | C14—C19—C18—C17 | −0.4 (6) |
N3—C2—C7—C6 | −177.9 (3) | C19—C14—C15—C16 | −1.5 (6) |
N3—C2—C3—N1 | 0.2 (4) | C19—C18—C17—C16 | −0.5 (7) |
N3—C2—C3—C4 | 177.6 (3) | C18—C17—C16—C15 | 0.4 (7) |
C1—N3—C2—C7 | 175.79 (18) | C17—C16—C15—C14 | 0.6 (6) |
C1—N3—C2—C3 | −2.4 (4) | C15—C14—C19—C18 | 1.4 (6) |
C1—C8—C9—C10 | 179.4 (3) | C8—C9—C10—C11 | 0.2 (4) |
C1—C8—C13—C12 | −179.3 (2) | C9—C8—C13—C12 | 0.6 (4) |
C2—N3—C1—N2 | 1.6 (4) | C9—C10—C11—C12 | 0.0 (4) |
C2—N3—C1—C8 | −178.2 (2) | C10—C11—C12—C13 | 0.1 (4) |
C2—C7—C6—C5 | 0.2 (4) | C11—C12—C13—C8 | −0.4 (5) |
C7—C2—C3—N1 | −178.0 (2) | C13—C8—C9—C10 | −0.5 (4) |
C7—C2—C3—C4 | −0.7 (4) |
C19H14N3 | F(000) = 596 |
Mr = 284.33 | Dx = 1.480 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.2760 (5) Å | Cell parameters from 2348 reflections |
b = 6.5173 (3) Å | θ = 3.3–24.8° |
c = 19.3323 (19) Å | µ = 0.09 mm−1 |
β = 99.826 (5)° | T = 271 K |
V = 1275.73 (15) Å3 | Block, clear dark brown |
Z = 4 | 0.18 × 0.14 × 0.09 mm |
Bruker SMART APEX2 area detector diffractometer | 878 independent reflections |
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs | 623 reflections with I > 2σ(I) |
Mirror optics monochromator | Rint = 0.033 |
Detector resolution: 7.9 pixels mm-1 | θmax = 26.3°, θmin = 2.1° |
ω and φ scans | h = −12→12 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0528 before and 0.0392 after correction. The Ratio of minimum to maximum transmission is 0.9029. The λ/2 correction factor is Not present. | k = −8→8 |
Tmin = 0.673, Tmax = 0.745 | l = −8→8 |
7309 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.089 | w = 1/[σ2(Fo2) + (0.0532P)2 + 0.0955P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
878 reflections | Δρmax = 0.07 e Å−3 |
199 parameters | Δρmin = −0.08 e Å−3 |
231 restraints |
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. High pressure data collection in a diamond anvil cell. 1.3749 GPa. PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 231 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 62 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 16 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 16 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info No action taken. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.4740 (2) | 0.7051 (3) | 0.6592 (3) | 0.033 (3) | |
N2 | 0.4427 (2) | 0.6972 (3) | 0.7246 (3) | 0.032 (3) | |
N3 | 0.2138 (2) | 0.6872 (3) | 0.6746 (3) | 0.028 (3) | |
C1 | 0.3131 (3) | 0.6913 (3) | 0.7280 (4) | 0.024 (3) | |
C2 | 0.2464 (3) | 0.6839 (3) | 0.6087 (4) | 0.025 (3) | |
C7 | 0.1492 (3) | 0.6675 (3) | 0.5500 (4) | 0.028 (3) | |
H7 | 0.061170 | 0.662991 | 0.555672 | 0.034* | |
C6 | 0.1792 (3) | 0.6575 (4) | 0.4839 (4) | 0.033 (3) | |
H6 | 0.111843 | 0.644938 | 0.445393 | 0.040* | |
C5 | 0.3106 (2) | 0.6662 (3) | 0.4738 (3) | 0.034 (3) | |
H5 | 0.330886 | 0.659318 | 0.428820 | 0.041* | |
C4 | 0.4096 (3) | 0.6849 (4) | 0.5311 (4) | 0.032 (3) | |
H4 | 0.497156 | 0.691484 | 0.524647 | 0.038* | |
C3 | 0.3799 (3) | 0.6940 (3) | 0.5979 (4) | 0.028 (3) | |
C14 | 0.61350 (18) | 0.7055 (3) | 0.6587 (3) | 0.022 (3) | |
C19 | 0.66769 (19) | 0.8527 (3) | 0.6212 (3) | 0.030 (3) | |
H19 | 0.614148 | 0.951774 | 0.596084 | 0.036* | |
C18 | 0.8019 (2) | 0.8525 (4) | 0.6212 (3) | 0.039 (4) | |
H18 | 0.838990 | 0.951456 | 0.595903 | 0.046* | |
C17 | 0.8802 (2) | 0.7074 (4) | 0.6584 (3) | 0.044 (3) | |
H17 | 0.970549 | 0.707151 | 0.657893 | 0.053* | |
C16 | 0.8264 (2) | 0.5613 (4) | 0.6966 (3) | 0.044 (4) | |
H16 | 0.880485 | 0.463217 | 0.722020 | 0.052* | |
C15 | 0.69115 (18) | 0.5604 (3) | 0.6972 (3) | 0.032 (3) | |
H15 | 0.654071 | 0.463192 | 0.723216 | 0.038* | |
C8 | 0.2819 (2) | 0.6883 (3) | 0.7999 (3) | 0.025 (3) | |
C9 | 0.1504 (2) | 0.7069 (3) | 0.8085 (3) | 0.034 (3) | |
H9 | 0.083882 | 0.720897 | 0.769583 | 0.041* | |
C10 | 0.1201 (3) | 0.7044 (4) | 0.8752 (3) | 0.037 (3) | |
H10 | 0.032525 | 0.717800 | 0.881015 | 0.045* | |
C11 | 0.2165 (2) | 0.6826 (3) | 0.9330 (3) | 0.039 (3) | |
H11 | 0.194585 | 0.680398 | 0.977719 | 0.047* | |
C12 | 0.3469 (3) | 0.6640 (4) | 0.9244 (4) | 0.034 (3) | |
H12 | 0.413100 | 0.648774 | 0.963366 | 0.041* | |
C13 | 0.3786 (3) | 0.6679 (3) | 0.8581 (3) | 0.029 (3) | |
H13 | 0.466455 | 0.656622 | 0.852559 | 0.035* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0192 (12) | 0.0380 (11) | 0.043 (9) | −0.0002 (8) | 0.010 (2) | 0.001 (2) |
N2 | 0.0191 (12) | 0.0358 (11) | 0.043 (9) | −0.0017 (7) | 0.006 (2) | −0.001 (2) |
N3 | 0.0200 (13) | 0.0317 (11) | 0.032 (8) | 0.0014 (8) | 0.000 (2) | 0.002 (2) |
C1 | 0.0199 (13) | 0.0216 (11) | 0.030 (8) | 0.0002 (8) | 0.001 (3) | −0.001 (2) |
C2 | 0.0226 (16) | 0.0243 (12) | 0.030 (9) | 0.0013 (9) | 0.006 (3) | −0.001 (3) |
C7 | 0.0194 (14) | 0.0349 (13) | 0.029 (9) | 0.0014 (9) | 0.001 (2) | −0.001 (3) |
C6 | 0.0320 (15) | 0.0363 (13) | 0.031 (10) | 0.0017 (10) | 0.006 (3) | −0.002 (3) |
C5 | 0.0313 (13) | 0.0400 (13) | 0.030 (10) | 0.0012 (9) | 0.004 (2) | 0.000 (2) |
C4 | 0.0232 (15) | 0.0383 (14) | 0.034 (9) | 0.0006 (10) | 0.007 (3) | −0.001 (3) |
C3 | 0.0225 (15) | 0.0255 (12) | 0.038 (9) | 0.0002 (9) | 0.006 (3) | −0.003 (2) |
C14 | 0.0177 (10) | 0.0359 (12) | 0.014 (9) | 0.0007 (8) | 0.002 (2) | −0.0012 (18) |
C19 | 0.0264 (11) | 0.0379 (13) | 0.025 (10) | −0.0006 (8) | 0.003 (2) | −0.0005 (18) |
C18 | 0.0277 (12) | 0.0609 (16) | 0.029 (12) | −0.0108 (10) | 0.009 (2) | −0.003 (2) |
C17 | 0.0206 (11) | 0.082 (2) | 0.029 (11) | 0.0002 (11) | 0.005 (2) | −0.005 (3) |
C16 | 0.0308 (12) | 0.0687 (18) | 0.030 (11) | 0.0162 (11) | 0.001 (2) | 0.004 (3) |
C15 | 0.0304 (11) | 0.0481 (14) | 0.019 (10) | 0.0020 (9) | 0.011 (2) | 0.001 (2) |
C8 | 0.0213 (14) | 0.0229 (11) | 0.029 (9) | −0.0007 (8) | 0.002 (3) | 0.000 (2) |
C9 | 0.0223 (14) | 0.0323 (13) | 0.048 (10) | −0.0030 (8) | 0.005 (3) | 0.001 (2) |
C10 | 0.0272 (14) | 0.0356 (13) | 0.052 (10) | −0.0026 (10) | 0.016 (3) | 0.002 (2) |
C11 | 0.0427 (15) | 0.0365 (13) | 0.042 (10) | −0.0054 (10) | 0.018 (3) | −0.001 (2) |
C12 | 0.0370 (16) | 0.0362 (14) | 0.029 (10) | −0.0027 (10) | 0.002 (3) | −0.003 (3) |
C13 | 0.0229 (14) | 0.0354 (13) | 0.029 (9) | −0.0002 (10) | 0.002 (3) | −0.001 (2) |
N1—N2 | 1.358 (7) | C19—C18 | 1.379 (3) |
N1—C3 | 1.397 (7) | C18—H18 | 0.9300 |
N1—C14 | 1.435 (3) | C18—C17 | 1.364 (5) |
N2—C1 | 1.345 (3) | C17—H17 | 0.9300 |
N3—C1 | 1.323 (6) | C17—C16 | 1.378 (5) |
N3—C2 | 1.372 (7) | C16—H16 | 0.9300 |
C1—C8 | 1.478 (7) | C16—C15 | 1.392 (3) |
C2—C7 | 1.381 (7) | C15—H15 | 0.9300 |
C2—C3 | 1.424 (4) | C8—C9 | 1.395 (4) |
C7—H7 | 0.9300 | C8—C13 | 1.375 (7) |
C7—C6 | 1.367 (8) | C9—H9 | 0.9300 |
C6—H6 | 0.9300 | C9—C10 | 1.377 (7) |
C6—C5 | 1.398 (4) | C10—H10 | 0.9300 |
C5—H5 | 0.9300 | C10—C11 | 1.369 (7) |
C5—C4 | 1.374 (6) | C11—H11 | 0.9300 |
C4—H4 | 0.9300 | C11—C12 | 1.384 (4) |
C4—C3 | 1.379 (7) | C12—H12 | 0.9300 |
C14—C19 | 1.375 (4) | C12—C13 | 1.376 (8) |
C14—C15 | 1.372 (4) | C13—H13 | 0.9300 |
C19—H19 | 0.9300 | ||
N2—N1—C3 | 123.2 (3) | C18—C19—H19 | 120.2 |
N2—N1—C14 | 113.7 (4) | C19—C18—H18 | 120.0 |
C3—N1—C14 | 122.8 (5) | C17—C18—C19 | 120.1 (3) |
C1—N2—N1 | 116.1 (5) | C17—C18—H18 | 120.0 |
C1—N3—C2 | 116.6 (3) | C18—C17—H17 | 119.8 |
N2—C1—C8 | 114.9 (5) | C18—C17—C16 | 120.5 (2) |
N3—C1—N2 | 127.0 (6) | C16—C17—H17 | 119.8 |
N3—C1—C8 | 118.1 (3) | C17—C16—H16 | 120.0 |
N3—C2—C7 | 120.4 (3) | C17—C16—C15 | 120.0 (3) |
N3—C2—C3 | 121.9 (5) | C15—C16—H16 | 120.0 |
C7—C2—C3 | 117.6 (6) | C14—C15—C16 | 118.8 (3) |
C2—C7—H7 | 119.2 | C14—C15—H15 | 120.6 |
C6—C7—C2 | 121.6 (3) | C16—C15—H15 | 120.6 |
C6—C7—H7 | 119.2 | C9—C8—C1 | 118.7 (5) |
C7—C6—H6 | 119.8 | C13—C8—C1 | 121.9 (3) |
C7—C6—C5 | 120.4 (5) | C13—C8—C9 | 119.4 (6) |
C5—C6—H6 | 119.8 | C8—C9—H9 | 120.4 |
C6—C5—H5 | 120.3 | C10—C9—C8 | 119.3 (5) |
C4—C5—C6 | 119.4 (5) | C10—C9—H9 | 120.4 |
C4—C5—H5 | 120.3 | C9—C10—H10 | 119.4 |
C5—C4—H4 | 119.8 | C11—C10—C9 | 121.2 (3) |
C5—C4—C3 | 120.4 (3) | C11—C10—H10 | 119.4 |
C3—C4—H4 | 119.8 | C10—C11—H11 | 120.3 |
N1—C3—C2 | 115.1 (5) | C10—C11—C12 | 119.5 (5) |
C4—C3—N1 | 124.4 (3) | C12—C11—H11 | 120.3 |
C4—C3—C2 | 120.5 (5) | C11—C12—H12 | 120.1 |
C19—C14—N1 | 120.0 (3) | C13—C12—C11 | 119.9 (5) |
C15—C14—N1 | 118.9 (3) | C13—C12—H12 | 120.1 |
C15—C14—C19 | 121.07 (19) | C8—C13—C12 | 120.8 (4) |
C14—C19—H19 | 120.2 | C8—C13—H13 | 119.6 |
C14—C19—C18 | 119.6 (3) | C12—C13—H13 | 119.6 |
N1—N2—C1—N3 | 1.9 (3) | C7—C6—C5—C4 | 0.0 (3) |
N1—N2—C1—C8 | −178.5 (2) | C6—C5—C4—C3 | 0.4 (4) |
N1—C14—C19—C18 | 179.7 (4) | C5—C4—C3—N1 | 177.45 (17) |
N1—C14—C15—C16 | −180.0 (4) | C5—C4—C3—C2 | 0.0 (4) |
N2—N1—C3—C2 | 3.0 (3) | C3—N1—N2—C1 | −4.2 (3) |
N2—N1—C3—C4 | −174.5 (2) | C3—N1—C14—C19 | 57.0 (4) |
N2—N1—C14—C19 | −128.8 (4) | C3—N1—C14—C15 | −124.5 (4) |
N2—N1—C14—C15 | 49.7 (4) | C3—C2—C7—C6 | 1.1 (4) |
N2—C1—C8—C9 | 172.43 (17) | C14—N1—N2—C1 | −178.41 (16) |
N2—C1—C8—C13 | −7.5 (3) | C14—N1—C3—C2 | 176.70 (18) |
N3—C1—C8—C9 | −7.8 (3) | C14—N1—C3—C4 | −0.8 (4) |
N3—C1—C8—C13 | 172.20 (18) | C14—C19—C18—C17 | −0.2 (6) |
N3—C2—C7—C6 | −177.9 (2) | C19—C14—C15—C16 | −1.5 (6) |
N3—C2—C3—N1 | 0.6 (3) | C19—C18—C17—C16 | −0.6 (7) |
N3—C2—C3—C4 | 178.3 (3) | C18—C17—C16—C15 | 0.4 (7) |
C1—N3—C2—C7 | 176.20 (17) | C17—C16—C15—C14 | 0.7 (6) |
C1—N3—C2—C3 | −2.8 (4) | C15—C14—C19—C18 | 1.2 (6) |
C1—C8—C9—C10 | −180.0 (2) | C8—C9—C10—C11 | −0.4 (4) |
C1—C8—C13—C12 | −179.5 (2) | C9—C8—C13—C12 | 0.5 (4) |
C2—N3—C1—N2 | 1.6 (4) | C9—C10—C11—C12 | 0.4 (4) |
C2—N3—C1—C8 | −178.1 (2) | C10—C11—C12—C13 | 0.1 (4) |
C2—C7—C6—C5 | −0.7 (4) | C11—C12—C13—C8 | −0.6 (4) |
C7—C2—C3—N1 | −178.4 (2) | C13—C8—C9—C10 | 0.0 (3) |
C7—C2—C3—C4 | −0.8 (3) |
C19H14N3 | F(000) = 596 |
Mr = 284.33 | Dx = 1.508 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.2411 (11) Å | Cell parameters from 1492 reflections |
b = 6.4507 (6) Å | θ = 3.3–26.2° |
c = 19.247 (4) Å | µ = 0.09 mm−1 |
β = 99.913 (13)° | T = 295 K |
V = 1252.5 (3) Å3 | Block, clear dark brown |
Z = 4 | 0.16 × 0.14 × 0.09 mm |
Bruker SMART APEX2 area detector diffractometer | 900 independent reflections |
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs | 537 reflections with I > 2σ(I) |
Mirror optics monochromator | Rint = 0.060 |
Detector resolution: 7.9 pixels mm-1 | θmax = 26.4°, θmin = 2.1° |
ω and φ scans | h = −12→12 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0770 before and 0.0513 after correction. The Ratio of minimum to maximum transmission is 0.8345. The λ/2 correction factor is Not present. | k = −8→8 |
Tmin = 0.622, Tmax = 0.745 | l = −8→8 |
7133 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.123 | w = 1/[σ2(Fo2) + (0.0587P)2 + 0.3163P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
900 reflections | Δρmax = 0.13 e Å−3 |
199 parameters | Δρmin = −0.14 e Å−3 |
231 restraints |
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. High pressure data collection in a diamond anvil cell. 1.8162 GPa. PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 3.19 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check Correct. H H contacts can be as short as 1.7 Ang. See Wood, Peter A., et al. "Analysis of the compression of molecular crystal structures using Hirshfeld surfaces." CrystEngComm 10.4 (2008): 368-376. PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 231 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 53 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ··· 5 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 16 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 16 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info No action taken. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.4743 (4) | 0.7028 (6) | 0.6592 (5) | 0.039 (4) | |
N2 | 0.4430 (3) | 0.6929 (5) | 0.7252 (4) | 0.037 (4) | |
N3 | 0.2133 (4) | 0.6837 (5) | 0.6754 (5) | 0.036 (4) | |
C1 | 0.3134 (4) | 0.6884 (5) | 0.7286 (5) | 0.030 (4) | |
C2 | 0.2452 (4) | 0.6818 (6) | 0.6092 (5) | 0.033 (4) | |
C7 | 0.1480 (5) | 0.6652 (6) | 0.5500 (5) | 0.034 (4) | |
H7 | 0.059594 | 0.659249 | 0.555500 | 0.040* | |
C6 | 0.1782 (4) | 0.6572 (6) | 0.4830 (5) | 0.038 (4) | |
H6 | 0.110648 | 0.645143 | 0.444216 | 0.046* | |
C5 | 0.3099 (4) | 0.6672 (5) | 0.4734 (5) | 0.041 (4) | |
H5 | 0.330357 | 0.662133 | 0.428182 | 0.049* | |
C4 | 0.4093 (5) | 0.6844 (6) | 0.5309 (5) | 0.039 (4) | |
H4 | 0.497235 | 0.690418 | 0.524691 | 0.047* | |
C3 | 0.3789 (4) | 0.6928 (6) | 0.5980 (5) | 0.035 (4) | |
C14 | 0.6139 (3) | 0.7035 (5) | 0.6584 (4) | 0.038 (4) | |
C19 | 0.6683 (4) | 0.8531 (5) | 0.6214 (5) | 0.039 (5) | |
H19 | 0.614517 | 0.953465 | 0.596278 | 0.047* | |
C18 | 0.8030 (4) | 0.8540 (6) | 0.6216 (5) | 0.050 (6) | |
H18 | 0.840288 | 0.955521 | 0.596815 | 0.060* | |
C17 | 0.8814 (4) | 0.7059 (7) | 0.6582 (5) | 0.055 (6) | |
H17 | 0.971862 | 0.704926 | 0.657253 | 0.066* | |
C16 | 0.8281 (4) | 0.5581 (6) | 0.6966 (5) | 0.051 (6) | |
H16 | 0.882793 | 0.459479 | 0.722077 | 0.061* | |
C15 | 0.6923 (3) | 0.5557 (5) | 0.6972 (5) | 0.040 (5) | |
H15 | 0.655306 | 0.456940 | 0.723216 | 0.048* | |
C8 | 0.2810 (4) | 0.6841 (6) | 0.8012 (5) | 0.033 (4) | |
C9 | 0.1491 (4) | 0.7030 (6) | 0.8092 (5) | 0.039 (5) | |
H9 | 0.082238 | 0.715055 | 0.770083 | 0.047* | |
C10 | 0.1196 (5) | 0.7033 (6) | 0.8768 (5) | 0.041 (5) | |
H10 | 0.031774 | 0.718284 | 0.882605 | 0.049* | |
C11 | 0.2156 (5) | 0.6822 (5) | 0.9352 (5) | 0.047 (5) | |
H11 | 0.193420 | 0.682157 | 0.980030 | 0.056* | |
C12 | 0.3467 (4) | 0.6607 (6) | 0.9266 (6) | 0.045 (4) | |
H12 | 0.412949 | 0.642810 | 0.965766 | 0.054* | |
C13 | 0.3783 (5) | 0.6661 (6) | 0.8601 (5) | 0.040 (4) | |
H13 | 0.466644 | 0.657340 | 0.854688 | 0.048* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.023 (2) | 0.0341 (16) | 0.064 (12) | 0.0001 (16) | 0.013 (4) | 0.002 (4) |
N2 | 0.018 (2) | 0.0336 (16) | 0.058 (12) | −0.0023 (14) | 0.003 (4) | −0.002 (4) |
N3 | 0.021 (2) | 0.0299 (15) | 0.056 (12) | 0.0025 (16) | 0.003 (4) | 0.003 (4) |
C1 | 0.014 (2) | 0.0181 (15) | 0.056 (11) | −0.0008 (16) | 0.003 (4) | −0.001 (4) |
C2 | 0.020 (3) | 0.0226 (17) | 0.056 (12) | −0.0008 (17) | 0.001 (4) | −0.008 (5) |
C7 | 0.019 (2) | 0.0304 (19) | 0.050 (13) | 0.0027 (18) | 0.003 (4) | 0.004 (4) |
C6 | 0.030 (3) | 0.0321 (19) | 0.052 (13) | −0.0026 (17) | 0.008 (5) | −0.007 (4) |
C5 | 0.031 (2) | 0.0354 (19) | 0.057 (13) | 0.0003 (18) | 0.011 (4) | 0.002 (4) |
C4 | 0.020 (2) | 0.035 (2) | 0.063 (13) | 0.0013 (18) | 0.008 (4) | −0.001 (4) |
C3 | 0.022 (3) | 0.0235 (17) | 0.062 (12) | 0.0008 (17) | 0.012 (4) | −0.007 (4) |
C14 | 0.018 (2) | 0.0326 (18) | 0.064 (14) | 0.0005 (15) | 0.010 (4) | −0.003 (3) |
C19 | 0.024 (2) | 0.040 (2) | 0.054 (16) | −0.0008 (15) | 0.008 (4) | −0.003 (3) |
C18 | 0.029 (2) | 0.057 (2) | 0.066 (19) | −0.0100 (18) | 0.013 (5) | −0.004 (4) |
C17 | 0.016 (2) | 0.077 (3) | 0.072 (18) | −0.002 (2) | 0.008 (5) | −0.009 (4) |
C16 | 0.026 (2) | 0.065 (3) | 0.056 (19) | 0.0134 (19) | −0.008 (5) | −0.001 (4) |
C15 | 0.029 (2) | 0.045 (2) | 0.046 (16) | 0.0017 (17) | 0.011 (4) | 0.003 (4) |
C8 | 0.017 (2) | 0.0248 (17) | 0.060 (12) | −0.0026 (16) | 0.011 (4) | 0.004 (4) |
C9 | 0.022 (3) | 0.0313 (18) | 0.064 (14) | −0.0022 (16) | 0.009 (4) | −0.001 (4) |
C10 | 0.026 (3) | 0.0336 (19) | 0.067 (15) | −0.0025 (19) | 0.017 (5) | −0.005 (4) |
C11 | 0.038 (3) | 0.0319 (18) | 0.071 (15) | −0.0038 (19) | 0.011 (5) | 0.001 (4) |
C12 | 0.033 (3) | 0.036 (2) | 0.063 (13) | −0.0008 (18) | −0.001 (5) | 0.003 (5) |
C13 | 0.023 (3) | 0.033 (2) | 0.064 (13) | −0.0029 (19) | 0.007 (4) | 0.005 (4) |
N1—N2 | 1.362 (8) | C19—C18 | 1.378 (5) |
N1—C3 | 1.397 (8) | C18—H18 | 0.9300 |
N1—C14 | 1.433 (5) | C18—C17 | 1.364 (7) |
N2—C1 | 1.340 (5) | C17—H17 | 0.9300 |
N3—C1 | 1.319 (7) | C17—C16 | 1.375 (7) |
N3—C2 | 1.367 (8) | C16—H16 | 0.9300 |
C1—C8 | 1.491 (8) | C16—C15 | 1.393 (5) |
C2—C7 | 1.384 (8) | C15—H15 | 0.9300 |
C2—C3 | 1.424 (6) | C8—C9 | 1.391 (5) |
C7—H7 | 0.9300 | C8—C13 | 1.379 (8) |
C7—C6 | 1.376 (8) | C9—H9 | 0.9300 |
C6—H6 | 0.9300 | C9—C10 | 1.385 (8) |
C6—C5 | 1.394 (6) | C10—H10 | 0.9300 |
C5—H5 | 0.9300 | C10—C11 | 1.367 (8) |
C5—C4 | 1.374 (8) | C11—H11 | 0.9300 |
C4—H4 | 0.9300 | C11—C12 | 1.387 (5) |
C4—C3 | 1.380 (8) | C12—H12 | 0.9300 |
C14—C19 | 1.373 (6) | C12—C13 | 1.374 (9) |
C14—C15 | 1.380 (6) | C13—H13 | 0.9300 |
C19—H19 | 0.9300 | ||
N2—N1—C3 | 122.8 (4) | C18—C19—H19 | 120.1 |
N2—N1—C14 | 114.0 (6) | C19—C18—H18 | 120.1 |
C3—N1—C14 | 123.0 (6) | C17—C18—C19 | 119.9 (5) |
C1—N2—N1 | 116.1 (6) | C17—C18—H18 | 120.1 |
C1—N3—C2 | 116.4 (5) | C18—C17—H17 | 119.7 |
N2—C1—C8 | 115.4 (6) | C18—C17—C16 | 120.7 (4) |
N3—C1—N2 | 127.3 (7) | C16—C17—H17 | 119.7 |
N3—C1—C8 | 117.3 (5) | C17—C16—H16 | 119.9 |
N3—C2—C7 | 121.0 (5) | C17—C16—C15 | 120.1 (5) |
N3—C2—C3 | 122.1 (7) | C15—C16—H16 | 119.9 |
C7—C2—C3 | 116.9 (7) | C14—C15—C16 | 118.4 (5) |
C2—C7—H7 | 119.0 | C14—C15—H15 | 120.8 |
C6—C7—C2 | 121.9 (5) | C16—C15—H15 | 120.8 |
C6—C7—H7 | 119.0 | C9—C8—C1 | 118.6 (7) |
C7—C6—H6 | 120.0 | C13—C8—C1 | 121.7 (5) |
C7—C6—C5 | 120.1 (7) | C13—C8—C9 | 119.6 (7) |
C5—C6—H6 | 120.0 | C8—C9—H9 | 120.7 |
C6—C5—H5 | 120.1 | C10—C9—C8 | 118.5 (7) |
C4—C5—C6 | 119.7 (7) | C10—C9—H9 | 120.7 |
C4—C5—H5 | 120.1 | C9—C10—H10 | 119.0 |
C5—C4—H4 | 119.9 | C11—C10—C9 | 121.9 (5) |
C5—C4—C3 | 120.2 (5) | C11—C10—H10 | 119.0 |
C3—C4—H4 | 119.9 | C10—C11—H11 | 120.4 |
N1—C3—C2 | 115.1 (7) | C10—C11—C12 | 119.1 (7) |
C4—C3—N1 | 123.6 (5) | C12—C11—H11 | 120.4 |
C4—C3—C2 | 121.2 (7) | C11—C12—H12 | 120.1 |
C19—C14—N1 | 120.2 (4) | C13—C12—C11 | 119.7 (7) |
C19—C14—C15 | 121.1 (3) | C13—C12—H12 | 120.1 |
C15—C14—N1 | 118.7 (4) | C8—C13—H13 | 119.5 |
C14—C19—H19 | 120.1 | C12—C13—C8 | 121.0 (6) |
C14—C19—C18 | 119.8 (5) | C12—C13—H13 | 119.5 |
N1—N2—C1—N3 | 3.2 (7) | C7—C6—C5—C4 | 0.2 (6) |
N1—N2—C1—C8 | −178.2 (4) | C6—C5—C4—C3 | −0.3 (6) |
N1—C14—C19—C18 | 179.2 (7) | C5—C4—C3—N1 | 177.6 (3) |
N1—C14—C15—C16 | −179.6 (7) | C5—C4—C3—C2 | 0.7 (7) |
N2—N1—C3—C2 | 3.0 (7) | C3—N1—N2—C1 | −4.8 (7) |
N2—N1—C3—C4 | −174.1 (4) | C3—N1—C14—C19 | 57.2 (7) |
N2—N1—C14—C19 | −128.6 (6) | C3—N1—C14—C15 | −124.9 (6) |
N2—N1—C14—C15 | 49.3 (7) | C3—C2—C7—C6 | 0.7 (7) |
N2—C1—C8—C9 | 172.9 (3) | C14—N1—N2—C1 | −179.0 (3) |
N2—C1—C8—C13 | −5.9 (6) | C14—N1—C3—C2 | 176.6 (3) |
N3—C1—C8—C9 | −8.4 (6) | C14—N1—C3—C4 | −0.5 (7) |
N3—C1—C8—C13 | 172.9 (3) | C14—C19—C18—C17 | 0.3 (11) |
N3—C2—C7—C6 | −178.1 (4) | C19—C14—C15—C16 | −1.7 (10) |
N3—C2—C3—N1 | 0.8 (7) | C19—C18—C17—C16 | −1.6 (11) |
N3—C2—C3—C4 | 178.0 (5) | C18—C17—C16—C15 | 1.3 (11) |
C1—N3—C2—C7 | 176.4 (3) | C17—C16—C15—C14 | 0.4 (11) |
C1—N3—C2—C3 | −2.4 (7) | C15—C14—C19—C18 | 1.4 (10) |
C1—C8—C9—C10 | −178.7 (4) | C8—C9—C10—C11 | −1.1 (7) |
C1—C8—C13—C12 | −179.5 (4) | C9—C8—C13—C12 | 1.8 (7) |
C2—N3—C1—N2 | 0.4 (7) | C9—C10—C11—C12 | 0.3 (7) |
C2—N3—C1—C8 | −178.2 (3) | C10—C11—C12—C13 | 1.6 (6) |
C2—C7—C6—C5 | −0.4 (7) | C11—C12—C13—C8 | −2.6 (8) |
C7—C2—C3—N1 | −178.0 (4) | C13—C8—C9—C10 | 0.1 (6) |
C7—C2—C3—C4 | −0.8 (7) |
C19H14N3 | F(000) = 596 |
Mr = 284.33 | Dx = 1.525 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.2225 (8) Å | Cell parameters from 2001 reflections |
b = 6.4019 (5) Å | θ = 3.4–25.2° |
c = 19.203 (3) Å | µ = 0.09 mm−1 |
β = 99.864 (8)° | T = 291 K |
V = 1238.2 (2) Å3 | Block, clear dark brown |
Z = 4 | 0.18 × 0.14 × 0.09 mm |
Bruker SMART APEX2 area detector diffractometer | 851 independent reflections |
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs | 558 reflections with I > 2σ(I) |
Mirror optics monochromator | Rint = 0.042 |
Detector resolution: 7.9 pixels mm-1 | θmax = 26.3°, θmin = 2.1° |
ω and φ scans | h = −12→12 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1040 before and 0.0459 after correction. The Ratio of minimum to maximum transmission is 0.8593. The λ/2 correction factor is Not present. | k = −7→7 |
Tmin = 0.641, Tmax = 0.745 | l = −8→8 |
6022 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.102 | w = 1/[σ2(Fo2) + (0.0563P)2 + 0.2672P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
851 reflections | Δρmax = 0.13 e Å−3 |
194 parameters | Δρmin = −0.15 e Å−3 |
201 restraints |
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. High pressure data collection in a diamond anvil cell. 2.1201 GPa. PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 3.17 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check Correct. H H contacts can be as short as 1.7 Ang. See Wood, Peter A., et al. "Analysis of the compression of molecular crystal structures using Hirshfeld surfaces." CrystEngComm 10.4 (2008): 368-376. PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 201 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 52 Note PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ···. 2 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ··· 1 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 15 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 15 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 1 Info No action taken. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.4741 (3) | 0.6998 (4) | 0.6597 (4) | 0.028 (3) | |
N2 | 0.4431 (2) | 0.6907 (4) | 0.7259 (4) | 0.028 (3) | |
N3 | 0.2127 (3) | 0.6810 (4) | 0.6752 (4) | 0.025 (3) | |
C1 | 0.3125 (3) | 0.6850 (5) | 0.7291 (4) | 0.022 (3) | |
C2 | 0.2453 (3) | 0.6803 (5) | 0.6088 (4) | 0.023 (3) | |
C7 | 0.1471 (3) | 0.6640 (5) | 0.5499 (4) | 0.027 (4) | |
H7 | 0.058687 | 0.658211 | 0.555568 | 0.032* | |
C6 | 0.1775 (3) | 0.6564 (5) | 0.4835 (4) | 0.031 (4) | |
H6 | 0.109678 | 0.643674 | 0.444693 | 0.037* | |
C5 | 0.3093 (3) | 0.6673 (4) | 0.4731 (4) | 0.029 (4) | |
H5 | 0.329216 | 0.662326 | 0.427669 | 0.035* | |
C4 | 0.4092 (3) | 0.6855 (5) | 0.5305 (4) | 0.028 (3) | |
H4 | 0.497083 | 0.693883 | 0.523913 | 0.033* | |
C3 | 0.3794 (3) | 0.6914 (5) | 0.5981 (4) | 0.025 (3) | |
C14 | 0.6144 (2) | 0.7014 (4) | 0.6593 (3) | 0.0214 (7)* | |
C19 | 0.6684 (2) | 0.8530 (4) | 0.6217 (4) | 0.023 (5) | |
H19 | 0.614534 | 0.953984 | 0.596516 | 0.027* | |
C18 | 0.8035 (3) | 0.8525 (5) | 0.6222 (4) | 0.040 (4) | |
H18 | 0.840819 | 0.954470 | 0.597211 | 0.048* | |
C17 | 0.8829 (3) | 0.7043 (5) | 0.6588 (4) | 0.039 (4) | |
H17 | 0.973634 | 0.704357 | 0.658246 | 0.047* | |
C16 | 0.8283 (3) | 0.5545 (5) | 0.6967 (4) | 0.040 (4) | |
H16 | 0.882717 | 0.454183 | 0.722000 | 0.048* | |
C15 | 0.6925 (2) | 0.5524 (4) | 0.6974 (4) | 0.030 (5) | |
H15 | 0.655405 | 0.452081 | 0.723129 | 0.036* | |
C8 | 0.2815 (3) | 0.6823 (5) | 0.8018 (4) | 0.023 (3) | |
C9 | 0.1492 (3) | 0.7013 (5) | 0.8105 (4) | 0.031 (4) | |
H9 | 0.082332 | 0.713391 | 0.771264 | 0.038* | |
C10 | 0.1182 (3) | 0.7022 (5) | 0.8775 (4) | 0.035 (4) | |
H10 | 0.030219 | 0.717500 | 0.883344 | 0.042* | |
C11 | 0.2153 (3) | 0.6808 (4) | 0.9357 (4) | 0.037 (4) | |
H11 | 0.193062 | 0.679663 | 0.980636 | 0.044* | |
C12 | 0.3473 (3) | 0.6607 (5) | 0.9275 (5) | 0.033 (4) | |
H12 | 0.413763 | 0.645757 | 0.966834 | 0.039* | |
C13 | 0.3785 (3) | 0.6632 (5) | 0.8605 (4) | 0.027 (4) | |
H13 | 0.466772 | 0.651722 | 0.854983 | 0.032* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0184 (15) | 0.0363 (15) | 0.034 (11) | 0.0005 (11) | 0.014 (3) | 0.001 (3) |
N2 | 0.0172 (14) | 0.0352 (15) | 0.034 (11) | −0.0022 (10) | 0.011 (3) | −0.007 (3) |
N3 | 0.0197 (16) | 0.0276 (14) | 0.029 (10) | 0.0008 (11) | 0.005 (3) | 0.000 (3) |
C1 | 0.0202 (16) | 0.0168 (15) | 0.028 (10) | −0.0019 (11) | 0.002 (3) | −0.002 (3) |
C2 | 0.0210 (18) | 0.0211 (16) | 0.030 (10) | 0.0014 (12) | 0.009 (3) | −0.002 (3) |
C7 | 0.0187 (17) | 0.0302 (17) | 0.032 (11) | 0.0020 (12) | 0.003 (3) | 0.001 (3) |
C6 | 0.0269 (18) | 0.0316 (18) | 0.034 (11) | 0.0003 (13) | 0.005 (3) | −0.003 (4) |
C5 | 0.0295 (16) | 0.0346 (18) | 0.025 (11) | 0.0008 (12) | 0.007 (3) | −0.002 (3) |
C4 | 0.0228 (17) | 0.0311 (17) | 0.031 (11) | 0.0013 (13) | 0.009 (3) | −0.001 (4) |
C3 | 0.0217 (18) | 0.0226 (16) | 0.032 (11) | 0.0000 (12) | 0.008 (3) | −0.008 (3) |
C19 | 0.0258 (14) | 0.0327 (18) | 0.010 (15) | 0.0002 (10) | 0.005 (3) | −0.002 (2) |
C18 | 0.0256 (15) | 0.054 (2) | 0.041 (15) | −0.0115 (13) | 0.009 (3) | −0.002 (3) |
C17 | 0.0183 (14) | 0.074 (3) | 0.029 (14) | 0.0000 (14) | 0.010 (3) | −0.005 (3) |
C16 | 0.0291 (16) | 0.063 (2) | 0.028 (14) | 0.0157 (14) | 0.006 (3) | 0.005 (3) |
C15 | 0.0309 (15) | 0.041 (2) | 0.023 (15) | 0.0019 (12) | 0.017 (3) | 0.003 (3) |
C8 | 0.0217 (17) | 0.0201 (15) | 0.027 (10) | −0.0002 (12) | 0.006 (3) | 0.002 (3) |
C9 | 0.0191 (16) | 0.0266 (17) | 0.049 (12) | −0.0020 (12) | 0.008 (3) | 0.000 (3) |
C10 | 0.0253 (17) | 0.0310 (18) | 0.054 (12) | −0.0024 (13) | 0.019 (3) | 0.000 (3) |
C11 | 0.0395 (18) | 0.0299 (17) | 0.047 (12) | −0.0051 (12) | 0.022 (3) | −0.003 (3) |
C12 | 0.0351 (19) | 0.0320 (18) | 0.031 (12) | −0.0033 (13) | 0.006 (4) | −0.002 (4) |
C13 | 0.0210 (17) | 0.0312 (18) | 0.028 (11) | 0.0008 (13) | 0.004 (3) | −0.001 (3) |
N1—N2 | 1.363 (8) | C19—C18 | 1.379 (3) |
N1—C3 | 1.395 (7) | C18—H18 | 0.9300 |
N1—C14 | 1.437 (3) | C18—C17 | 1.363 (6) |
N2—C1 | 1.348 (4) | C17—H17 | 0.9300 |
N3—C1 | 1.324 (7) | C17—C16 | 1.378 (6) |
N3—C2 | 1.371 (8) | C16—H16 | 0.9300 |
C1—C8 | 1.483 (8) | C16—C15 | 1.391 (3) |
C2—C7 | 1.382 (7) | C15—H15 | 0.9300 |
C2—C3 | 1.423 (5) | C8—C9 | 1.396 (5) |
C7—H7 | 0.9300 | C8—C13 | 1.374 (7) |
C7—C6 | 1.363 (8) | C9—H9 | 0.9300 |
C6—H6 | 0.9300 | C9—C10 | 1.377 (8) |
C6—C5 | 1.397 (5) | C10—H10 | 0.9300 |
C5—H5 | 0.9300 | C10—C11 | 1.368 (7) |
C5—C4 | 1.373 (7) | C11—H11 | 0.9300 |
C4—H4 | 0.9300 | C11—C12 | 1.391 (4) |
C4—C3 | 1.384 (8) | C12—H12 | 0.9300 |
C14—C19 | 1.379 (5) | C12—C13 | 1.377 (8) |
C14—C15 | 1.372 (5) | C13—H13 | 0.9300 |
C19—H19 | 0.9300 | ||
N2—N1—C3 | 123.4 (4) | C18—C19—H19 | 120.5 |
N2—N1—C14 | 113.4 (5) | C19—C18—H18 | 119.6 |
C3—N1—C14 | 123.0 (6) | C17—C18—C19 | 120.8 (4) |
C1—N2—N1 | 115.7 (5) | C17—C18—H18 | 119.6 |
C1—N3—C2 | 116.8 (4) | C18—C17—H17 | 120.1 |
N2—C1—C8 | 114.7 (5) | C18—C17—C16 | 119.9 (3) |
N3—C1—N2 | 126.9 (7) | C16—C17—H17 | 120.1 |
N3—C1—C8 | 118.4 (4) | C17—C16—H16 | 119.8 |
N3—C2—C7 | 120.3 (4) | C17—C16—C15 | 120.4 (4) |
N3—C2—C3 | 121.8 (6) | C15—C16—H16 | 119.8 |
C7—C2—C3 | 117.9 (6) | C14—C15—C16 | 118.6 (4) |
C2—C7—H7 | 119.4 | C14—C15—H15 | 120.7 |
C6—C7—C2 | 121.3 (4) | C16—C15—H15 | 120.7 |
C6—C7—H7 | 119.4 | C9—C8—C1 | 118.7 (5) |
C7—C6—H6 | 119.6 | C13—C8—C1 | 122.2 (4) |
C7—C6—C5 | 120.7 (6) | C13—C8—C9 | 119.1 (6) |
C5—C6—H6 | 119.6 | C8—C9—H9 | 120.1 |
C6—C5—H5 | 120.2 | C10—C9—C8 | 119.7 (6) |
C4—C5—C6 | 119.5 (6) | C10—C9—H9 | 120.1 |
C4—C5—H5 | 120.2 | C9—C10—H10 | 119.6 |
C5—C4—H4 | 119.9 | C11—C10—C9 | 120.7 (4) |
C5—C4—C3 | 120.1 (4) | C11—C10—H10 | 119.6 |
C3—C4—H4 | 119.9 | C10—C11—H11 | 120.0 |
N1—C3—C2 | 115.2 (6) | C10—C11—C12 | 120.0 (7) |
C4—C3—N1 | 124.3 (4) | C12—C11—H11 | 120.0 |
C4—C3—C2 | 120.5 (5) | C11—C12—H12 | 120.4 |
C19—C14—N1 | 119.8 (3) | C13—C12—C11 | 119.2 (6) |
C15—C14—N1 | 118.9 (3) | C13—C12—H12 | 120.4 |
C15—C14—C19 | 121.3 (2) | C8—C13—C12 | 121.2 (4) |
C14—C19—H19 | 120.5 | C8—C13—H13 | 119.4 |
C14—C19—C18 | 119.0 (4) | C12—C13—H13 | 119.4 |
N1—N2—C1—N3 | 2.2 (5) | C7—C6—C5—C4 | 0.2 (5) |
N1—N2—C1—C8 | −178.1 (3) | C6—C5—C4—C3 | 0.5 (5) |
N1—C14—C19—C18 | 179.7 (5) | C5—C4—C3—N1 | 176.9 (2) |
N1—C14—C15—C16 | 179.9 (5) | C5—C4—C3—C2 | −0.5 (5) |
N2—N1—C3—C2 | 2.3 (5) | C3—N1—N2—C1 | −3.7 (5) |
N2—N1—C3—C4 | −175.2 (3) | C3—N1—C14—C19 | 56.2 (6) |
N2—N1—C14—C19 | −128.7 (5) | C3—N1—C14—C15 | −124.7 (5) |
N2—N1—C14—C15 | 50.4 (6) | C3—C2—C7—C6 | 0.8 (5) |
N2—C1—C8—C9 | 172.5 (2) | C14—N1—N2—C1 | −178.8 (2) |
N2—C1—C8—C13 | −7.0 (5) | C14—N1—C3—C2 | 176.9 (3) |
N3—C1—C8—C9 | −7.7 (5) | C14—N1—C3—C4 | −0.6 (5) |
N3—C1—C8—C13 | 172.8 (2) | C14—C19—C18—C17 | 0.3 (9) |
N3—C2—C7—C6 | −177.9 (3) | C19—C14—C15—C16 | −1.0 (8) |
N3—C2—C3—N1 | 0.9 (4) | C19—C18—C17—C16 | −0.9 (9) |
N3—C2—C3—C4 | 178.5 (4) | C18—C17—C16—C15 | 0.5 (9) |
C1—N3—C2—C7 | 176.3 (2) | C17—C16—C15—C14 | 0.4 (8) |
C1—N3—C2—C3 | −2.3 (5) | C15—C14—C19—C18 | 0.7 (8) |
C1—C8—C9—C10 | −179.1 (3) | C8—C9—C10—C11 | −1.2 (5) |
C1—C8—C13—C12 | −179.9 (3) | C9—C8—C13—C12 | 0.6 (5) |
C2—N3—C1—N2 | 0.8 (5) | C9—C10—C11—C12 | 0.9 (5) |
C2—N3—C1—C8 | −179.0 (3) | C10—C11—C12—C13 | 0.2 (5) |
C2—C7—C6—C5 | −0.8 (6) | C11—C12—C13—C8 | −0.9 (6) |
C7—C2—C3—N1 | −177.7 (3) | C13—C8—C9—C10 | 0.5 (5) |
C7—C2—C3—C4 | −0.1 (5) |
C19H14N3 | F(000) = 596 |
Mr = 284.33 | Dx = 1.554 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.1831 (9) Å | Cell parameters from 1401 reflections |
b = 6.3399 (5) Å | θ = 3.4–24.0° |
c = 19.111 (4) Å | µ = 0.09 mm−1 |
β = 99.868 (11)° | T = 295 K |
V = 1215.6 (3) Å3 | Block, clear dark brown |
Z = 4 | 0.16 × 0.14 × 0.09 mm |
Bruker SMART APEX2 area detector diffractometer | 798 independent reflections |
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs | 504 reflections with I > 2σ(I) |
Mirror optics monochromator | Rint = 0.055 |
Detector resolution: 7.9 pixels mm-1 | θmax = 25.8°, θmin = 2.1° |
φ and ω scans | h = −12→11 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1003 before and 0.0528 after correction. The Ratio of minimum to maximum transmission is 0.8006. The λ/2 correction factor is Not present. | k = −7→7 |
Tmin = 0.597, Tmax = 0.745 | l = −8→8 |
5150 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.150 | w = 1/[σ2(Fo2) + (0.1006P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
798 reflections | Δρmax = 0.16 e Å−3 |
199 parameters | Δρmin = −0.16 e Å−3 |
231 restraints |
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. High pressure data collection in a diamond anvil cell. 2.5349 GPa. PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large 0.10 Report PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 3.14 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.17 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check Correct. H H contacts can be as short as 1.7 Ang. See Wood, Peter A., et al. "Analysis of the compression of molecular crystal structures using Hirshfeld surfaces." CrystEngComm 10.4 (2008): 368-376. PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 231 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 38 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ··· 4 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 15 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 15 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info No action taken. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.4744 (4) | 0.6960 (6) | 0.6606 (5) | 0.038 (4) | |
N2 | 0.4430 (3) | 0.6863 (6) | 0.7269 (5) | 0.037 (4) | |
N3 | 0.2125 (4) | 0.6779 (5) | 0.6765 (5) | 0.037 (4) | |
C1 | 0.3132 (5) | 0.6808 (6) | 0.7302 (6) | 0.032 (4) | |
C2 | 0.2447 (5) | 0.6770 (6) | 0.6099 (6) | 0.035 (5) | |
C7 | 0.1466 (5) | 0.6618 (6) | 0.5499 (6) | 0.036 (5) | |
H7 | 0.057756 | 0.654723 | 0.555574 | 0.044* | |
C6 | 0.1766 (5) | 0.6568 (6) | 0.4823 (6) | 0.039 (5) | |
H6 | 0.109034 | 0.646253 | 0.442974 | 0.047* | |
C5 | 0.3095 (5) | 0.6679 (5) | 0.4736 (5) | 0.041 (5) | |
H5 | 0.330786 | 0.664109 | 0.428216 | 0.049* | |
C4 | 0.4092 (5) | 0.6843 (7) | 0.5316 (6) | 0.040 (5) | |
H4 | 0.497608 | 0.691289 | 0.525161 | 0.047* | |
C3 | 0.3795 (5) | 0.6904 (6) | 0.5993 (5) | 0.036 (5) | |
C14 | 0.6150 (4) | 0.6984 (5) | 0.6598 (5) | 0.031 (5) | |
C19 | 0.6692 (4) | 0.8524 (5) | 0.6226 (5) | 0.038 (6) | |
H19 | 0.615032 | 0.954491 | 0.597294 | 0.045* | |
C18 | 0.8043 (4) | 0.8529 (6) | 0.6233 (6) | 0.056 (7) | |
H18 | 0.841877 | 0.957793 | 0.599081 | 0.067* | |
C17 | 0.8837 (4) | 0.7023 (7) | 0.6591 (6) | 0.066 (6) | |
H17 | 0.974760 | 0.702552 | 0.658270 | 0.080* | |
C16 | 0.8295 (4) | 0.5495 (7) | 0.6964 (6) | 0.062 (7) | |
H16 | 0.884319 | 0.446018 | 0.720423 | 0.074* | |
C15 | 0.6939 (4) | 0.5475 (5) | 0.6986 (5) | 0.037 (5) | |
H15 | 0.657443 | 0.447753 | 0.725326 | 0.044* | |
C8 | 0.2810 (5) | 0.6785 (6) | 0.8032 (6) | 0.033 (4) | |
C9 | 0.1478 (4) | 0.6977 (6) | 0.8105 (6) | 0.042 (5) | |
H9 | 0.080806 | 0.708746 | 0.770941 | 0.051* | |
C10 | 0.1183 (6) | 0.6999 (6) | 0.8787 (5) | 0.044 (5) | |
H10 | 0.030096 | 0.715585 | 0.884635 | 0.053* | |
C11 | 0.2149 (5) | 0.6798 (5) | 0.9376 (6) | 0.047 (5) | |
H11 | 0.191802 | 0.680658 | 0.982573 | 0.056* | |
C12 | 0.3476 (5) | 0.6581 (7) | 0.9302 (6) | 0.045 (5) | |
H12 | 0.414091 | 0.642019 | 0.969749 | 0.054* | |
C13 | 0.3781 (5) | 0.6611 (7) | 0.8627 (6) | 0.039 (5) | |
H13 | 0.466891 | 0.651063 | 0.857168 | 0.047* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.020 (2) | 0.0314 (17) | 0.066 (14) | −0.0006 (17) | 0.017 (4) | −0.007 (4) |
N2 | 0.018 (2) | 0.0326 (17) | 0.063 (14) | 0.0017 (14) | 0.011 (4) | −0.003 (4) |
N3 | 0.019 (2) | 0.0265 (16) | 0.067 (14) | 0.0029 (16) | 0.010 (4) | −0.002 (4) |
C1 | 0.017 (3) | 0.0180 (17) | 0.065 (13) | 0.0002 (16) | 0.014 (4) | 0.000 (4) |
C2 | 0.018 (3) | 0.0209 (18) | 0.065 (14) | 0.0025 (18) | 0.007 (4) | −0.003 (5) |
C7 | 0.016 (3) | 0.0300 (19) | 0.063 (14) | 0.0042 (18) | 0.005 (5) | 0.007 (4) |
C6 | 0.028 (3) | 0.0291 (19) | 0.062 (15) | 0.0008 (17) | 0.011 (5) | −0.001 (5) |
C5 | 0.031 (3) | 0.0286 (19) | 0.065 (15) | −0.0002 (18) | 0.014 (5) | 0.003 (4) |
C4 | 0.024 (3) | 0.031 (2) | 0.067 (14) | −0.0027 (19) | 0.017 (5) | −0.006 (5) |
C3 | 0.023 (3) | 0.0217 (18) | 0.064 (14) | 0.0021 (19) | 0.010 (4) | −0.004 (5) |
C14 | 0.015 (2) | 0.0309 (18) | 0.050 (15) | −0.0018 (15) | 0.009 (4) | −0.007 (3) |
C19 | 0.022 (2) | 0.034 (2) | 0.056 (18) | −0.0021 (15) | 0.004 (5) | 0.002 (3) |
C18 | 0.025 (3) | 0.050 (2) | 0.10 (2) | −0.0091 (19) | 0.017 (5) | 0.000 (4) |
C17 | 0.016 (3) | 0.073 (3) | 0.11 (2) | 0.003 (2) | 0.020 (5) | 0.001 (5) |
C16 | 0.030 (3) | 0.061 (3) | 0.10 (2) | 0.014 (2) | 0.014 (6) | 0.004 (4) |
C15 | 0.025 (2) | 0.041 (2) | 0.047 (17) | 0.0045 (17) | 0.013 (5) | 0.004 (4) |
C8 | 0.015 (3) | 0.0215 (17) | 0.066 (13) | −0.0006 (17) | 0.012 (4) | 0.005 (5) |
C9 | 0.024 (3) | 0.0261 (19) | 0.080 (16) | −0.0022 (16) | 0.016 (5) | 0.004 (4) |
C10 | 0.024 (3) | 0.0276 (19) | 0.084 (17) | −0.0036 (18) | 0.021 (5) | −0.002 (4) |
C11 | 0.035 (3) | 0.0256 (19) | 0.082 (17) | −0.0057 (18) | 0.019 (5) | −0.005 (4) |
C12 | 0.037 (3) | 0.031 (2) | 0.068 (15) | −0.0010 (19) | 0.014 (5) | −0.001 (5) |
C13 | 0.020 (3) | 0.030 (2) | 0.069 (14) | 0.0000 (19) | 0.008 (5) | 0.002 (4) |
N1—N2 | 1.360 (9) | C19—C18 | 1.374 (5) |
N1—C3 | 1.386 (8) | C18—H18 | 0.9300 |
N1—C14 | 1.435 (5) | C18—C17 | 1.357 (7) |
N2—C1 | 1.334 (6) | C17—H17 | 0.9300 |
N3—C1 | 1.321 (8) | C17—C16 | 1.373 (7) |
N3—C2 | 1.367 (8) | C16—H16 | 0.9300 |
C1—C8 | 1.487 (8) | C16—C15 | 1.389 (5) |
C2—C7 | 1.389 (8) | C15—H15 | 0.9300 |
C2—C3 | 1.424 (7) | C8—C9 | 1.393 (6) |
C7—H7 | 0.9300 | C8—C13 | 1.377 (8) |
C7—C6 | 1.379 (9) | C9—H9 | 0.9300 |
C6—H6 | 0.9300 | C9—C10 | 1.387 (9) |
C6—C5 | 1.393 (6) | C10—H10 | 0.9300 |
C5—H5 | 0.9300 | C10—C11 | 1.367 (8) |
C5—C4 | 1.373 (8) | C11—H11 | 0.9300 |
C4—H4 | 0.9300 | C11—C12 | 1.389 (6) |
C4—C3 | 1.379 (9) | C12—H12 | 0.9300 |
C14—C19 | 1.377 (7) | C12—C13 | 1.377 (9) |
C14—C15 | 1.381 (7) | C13—H13 | 0.9300 |
C19—H19 | 0.9300 | ||
N2—N1—C3 | 123.1 (5) | C18—C19—H19 | 120.5 |
N2—N1—C14 | 113.9 (7) | C19—C18—H18 | 119.6 |
C3—N1—C14 | 122.9 (7) | C17—C18—C19 | 120.9 (5) |
C1—N2—N1 | 116.0 (7) | C17—C18—H18 | 119.6 |
C1—N3—C2 | 116.4 (5) | C18—C17—H17 | 120.0 |
N2—C1—C8 | 115.1 (7) | C18—C17—C16 | 120.0 (4) |
N3—C1—N2 | 127.4 (8) | C16—C17—H17 | 120.0 |
N3—C1—C8 | 117.5 (5) | C17—C16—H16 | 119.6 |
N3—C2—C7 | 121.0 (5) | C17—C16—C15 | 120.8 (5) |
N3—C2—C3 | 121.5 (7) | C15—C16—H16 | 119.6 |
C7—C2—C3 | 117.5 (7) | C14—C15—C16 | 117.9 (5) |
C2—C7—H7 | 118.9 | C14—C15—H15 | 121.1 |
C6—C7—C2 | 122.1 (5) | C16—C15—H15 | 121.1 |
C6—C7—H7 | 118.9 | C9—C8—C1 | 117.9 (7) |
C7—C6—H6 | 120.4 | C13—C8—C1 | 122.2 (5) |
C7—C6—C5 | 119.1 (8) | C13—C8—C9 | 119.9 (8) |
C5—C6—H6 | 120.4 | C8—C9—H9 | 121.1 |
C6—C5—H5 | 119.8 | C10—C9—C8 | 117.8 (8) |
C4—C5—C6 | 120.5 (8) | C10—C9—H9 | 121.1 |
C4—C5—H5 | 119.8 | C9—C10—H10 | 119.0 |
C5—C4—H4 | 119.7 | C11—C10—C9 | 122.1 (5) |
C5—C4—C3 | 120.6 (5) | C11—C10—H10 | 119.0 |
C3—C4—H4 | 119.7 | C10—C11—H11 | 120.0 |
N1—C3—C2 | 115.5 (7) | C10—C11—C12 | 120.1 (8) |
C4—C3—N1 | 124.1 (5) | C12—C11—H11 | 120.0 |
C4—C3—C2 | 120.2 (7) | C11—C12—H12 | 120.9 |
C19—C14—N1 | 120.1 (4) | C13—C12—C11 | 118.2 (8) |
C19—C14—C15 | 121.4 (3) | C13—C12—H12 | 120.9 |
C15—C14—N1 | 118.5 (5) | C8—C13—H13 | 119.0 |
C14—C19—H19 | 120.5 | C12—C13—C8 | 121.9 (6) |
C18—C19—C14 | 119.0 (5) | C12—C13—H13 | 119.0 |
N1—N2—C1—N3 | 2.0 (7) | C7—C6—C5—C4 | −0.2 (6) |
N1—N2—C1—C8 | −177.8 (4) | C6—C5—C4—C3 | −0.1 (7) |
N1—C14—C19—C18 | 179.1 (8) | C5—C4—C3—N1 | 176.6 (3) |
N1—C14—C15—C16 | 179.0 (8) | C5—C4—C3—C2 | 0.8 (7) |
N2—N1—C3—C2 | 1.0 (7) | C3—N1—N2—C1 | −3.0 (7) |
N2—N1—C3—C4 | −175.0 (4) | C3—N1—C14—C19 | 55.8 (8) |
N2—N1—C14—C19 | −128.1 (7) | C3—N1—C14—C15 | −126.1 (7) |
N2—N1—C14—C15 | 50.0 (8) | C3—C2—C7—C6 | 0.8 (7) |
N2—C1—C8—C9 | 172.6 (3) | C14—N1—N2—C1 | −179.1 (3) |
N2—C1—C8—C13 | −6.5 (7) | C14—N1—C3—C2 | 176.7 (3) |
N3—C1—C8—C9 | −7.2 (6) | C14—N1—C3—C4 | 0.7 (8) |
N3—C1—C8—C13 | 173.7 (3) | C14—C19—C18—C17 | 1.2 (12) |
N3—C2—C7—C6 | −178.8 (4) | C19—C14—C15—C16 | −2.9 (11) |
N3—C2—C3—N1 | 2.4 (6) | C19—C18—C17—C16 | −1.5 (13) |
N3—C2—C3—C4 | 178.5 (5) | C18—C17—C16—C15 | −0.5 (13) |
C1—N3—C2—C7 | 176.3 (3) | C17—C16—C15—C14 | 2.6 (12) |
C1—N3—C2—C3 | −3.3 (7) | C15—C14—C19—C18 | 1.1 (12) |
C1—C8—C9—C10 | −178.7 (4) | C8—C9—C10—C11 | −1.3 (7) |
C1—C8—C13—C12 | −179.7 (4) | C9—C8—C13—C12 | 1.2 (7) |
C2—N3—C1—N2 | 1.1 (7) | C9—C10—C11—C12 | 0.6 (7) |
C2—N3—C1—C8 | −179.1 (3) | C10—C11—C12—C13 | 1.1 (6) |
C2—C7—C6—C5 | −0.1 (7) | C11—C12—C13—C8 | −2.0 (8) |
C7—C2—C3—N1 | −177.3 (4) | C13—C8—C9—C10 | 0.4 (6) |
C7—C2—C3—C4 | −1.2 (6) |
C19H14N3 | F(000) = 596 |
Mr = 284.33 | Dx = 1.554 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.1864 (8) Å | Cell parameters from 1975 reflections |
b = 6.3323 (5) Å | θ = 3.4–25.1° |
c = 19.118 (3) Å | µ = 0.09 mm−1 |
β = 99.822 (9)° | T = 276 K |
V = 1215.1 (3) Å3 | Block, clear dark brown |
Z = 4 | 0.18 × 0.14 × 0.09 mm |
Bruker SMART APEX2 area detector diffractometer | 865 independent reflections |
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs | 558 reflections with I > 2σ(I) |
Mirror optics monochromator | Rint = 0.050 |
Detector resolution: 7.9 pixels mm-1 | θmax = 26.3°, θmin = 2.1° |
ω and φ scans | h = −12→12 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1563 before and 0.0780 after correction. The Ratio of minimum to maximum transmission is 0.8154. The λ/2 correction factor is Not present. | k = −7→7 |
Tmin = 0.608, Tmax = 0.745 | l = −8→8 |
6204 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.112 | w = 1/[σ2(Fo2) + (0.0716P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
865 reflections | Δρmax = 0.14 e Å−3 |
199 parameters | Δρmin = −0.12 e Å−3 |
231 restraints |
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. High pressure data collection in a diamond anvil cell. 2.5349 GPa. PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 3.14 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.17 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check Correct. H H contacts can be as short as 1.7 Ang. See Wood, Peter A., et al. "Analysis of the compression of molecular crystal structures using Hirshfeld surfaces." CrystEngComm 10.4 (2008): 368-376. PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 231 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 49 Note PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ···. 2 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ··· 1 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 15 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 15 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info No action taken. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.4739 (3) | 0.6963 (4) | 0.6606 (4) | 0.029 (3) | |
N2 | 0.4428 (2) | 0.6863 (4) | 0.7271 (3) | 0.029 (3) | |
N3 | 0.2118 (3) | 0.6774 (4) | 0.6756 (4) | 0.028 (3) | |
C1 | 0.3118 (3) | 0.6799 (4) | 0.7301 (4) | 0.022 (3) | |
C2 | 0.2449 (3) | 0.6772 (4) | 0.6089 (4) | 0.024 (3) | |
C7 | 0.1460 (3) | 0.6615 (4) | 0.5498 (4) | 0.027 (3) | |
H7 | 0.057247 | 0.654255 | 0.555526 | 0.032* | |
C6 | 0.1768 (3) | 0.6564 (4) | 0.4833 (4) | 0.030 (3) | |
H6 | 0.108947 | 0.645142 | 0.444219 | 0.037* | |
C5 | 0.3091 (3) | 0.6680 (4) | 0.4729 (4) | 0.032 (3) | |
H5 | 0.328948 | 0.663824 | 0.427254 | 0.039* | |
C4 | 0.4095 (3) | 0.6855 (5) | 0.5303 (4) | 0.030 (3) | |
H4 | 0.497627 | 0.694245 | 0.523577 | 0.036* | |
C3 | 0.3792 (3) | 0.6900 (4) | 0.5982 (4) | 0.027 (3) | |
C14 | 0.6150 (2) | 0.6987 (4) | 0.6599 (3) | 0.024 (3) | |
C19 | 0.6690 (2) | 0.8524 (4) | 0.6224 (4) | 0.029 (4) | |
H19 | 0.614744 | 0.954917 | 0.597465 | 0.035* | |
C18 | 0.8045 (3) | 0.8528 (4) | 0.6223 (4) | 0.041 (4) | |
H18 | 0.841845 | 0.955457 | 0.596973 | 0.049* | |
C17 | 0.8837 (3) | 0.7028 (5) | 0.6594 (4) | 0.047 (4) | |
H17 | 0.975050 | 0.704387 | 0.659427 | 0.056* | |
C16 | 0.8295 (3) | 0.5488 (5) | 0.6967 (4) | 0.040 (4) | |
H16 | 0.884073 | 0.446280 | 0.721509 | 0.048* | |
C15 | 0.6934 (2) | 0.5467 (4) | 0.6974 (3) | 0.032 (4) | |
H15 | 0.656014 | 0.444215 | 0.722859 | 0.038* | |
C8 | 0.2808 (3) | 0.6784 (4) | 0.8030 (4) | 0.024 (3) | |
C9 | 0.1484 (3) | 0.6974 (4) | 0.8119 (4) | 0.034 (3) | |
H9 | 0.081017 | 0.708815 | 0.772541 | 0.041* | |
C10 | 0.1182 (3) | 0.6992 (5) | 0.8793 (4) | 0.037 (4) | |
H10 | 0.029893 | 0.714255 | 0.885100 | 0.044* | |
C11 | 0.2158 (3) | 0.6793 (4) | 0.9384 (4) | 0.040 (4) | |
H11 | 0.193389 | 0.679826 | 0.983571 | 0.047* | |
C12 | 0.3476 (3) | 0.6585 (5) | 0.9299 (5) | 0.031 (3) | |
H12 | 0.414443 | 0.643532 | 0.969301 | 0.037* | |
C13 | 0.3787 (4) | 0.6603 (5) | 0.8626 (4) | 0.029 (3) | |
H13 | 0.467391 | 0.649057 | 0.856991 | 0.035* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0205 (15) | 0.0346 (14) | 0.036 (10) | −0.0001 (11) | 0.017 (3) | −0.006 (2) |
N2 | 0.0206 (15) | 0.0342 (14) | 0.036 (9) | −0.0007 (10) | 0.013 (3) | −0.005 (3) |
N3 | 0.0206 (16) | 0.0288 (14) | 0.034 (9) | 0.0018 (10) | 0.006 (3) | −0.001 (2) |
C1 | 0.0193 (16) | 0.0166 (15) | 0.030 (9) | 0.0003 (11) | 0.008 (3) | −0.003 (3) |
C2 | 0.0223 (19) | 0.0215 (15) | 0.030 (10) | 0.0019 (12) | 0.009 (3) | −0.003 (3) |
C7 | 0.0174 (16) | 0.0328 (17) | 0.030 (10) | 0.0017 (12) | 0.005 (3) | 0.002 (3) |
C6 | 0.031 (2) | 0.0320 (17) | 0.030 (11) | 0.0006 (12) | 0.011 (3) | −0.002 (3) |
C5 | 0.0295 (17) | 0.0342 (17) | 0.036 (11) | 0.0004 (12) | 0.012 (3) | 0.000 (2) |
C4 | 0.0244 (18) | 0.0339 (17) | 0.036 (10) | −0.0013 (13) | 0.016 (3) | 0.000 (3) |
C3 | 0.0211 (18) | 0.0227 (15) | 0.037 (10) | −0.0003 (12) | 0.007 (3) | −0.005 (3) |
C14 | 0.0147 (13) | 0.0329 (16) | 0.025 (11) | −0.0002 (10) | 0.006 (2) | −0.005 (2) |
C19 | 0.0240 (14) | 0.0346 (18) | 0.029 (12) | −0.0039 (10) | 0.004 (3) | −0.004 (2) |
C18 | 0.0238 (15) | 0.055 (2) | 0.046 (14) | −0.0110 (12) | 0.011 (3) | −0.002 (3) |
C17 | 0.0188 (15) | 0.073 (3) | 0.051 (13) | 0.0008 (14) | 0.015 (3) | 0.001 (3) |
C16 | 0.0308 (16) | 0.062 (2) | 0.025 (14) | 0.0156 (14) | 0.002 (3) | 0.006 (3) |
C15 | 0.0270 (14) | 0.0414 (19) | 0.029 (12) | 0.0005 (12) | 0.011 (3) | 0.001 (3) |
C8 | 0.0224 (18) | 0.0220 (15) | 0.031 (9) | 0.0004 (12) | 0.012 (3) | −0.004 (3) |
C9 | 0.0233 (18) | 0.0282 (16) | 0.054 (11) | −0.0031 (11) | 0.015 (3) | 0.001 (3) |
C10 | 0.0242 (17) | 0.0316 (17) | 0.059 (11) | −0.0033 (13) | 0.018 (3) | −0.003 (3) |
C11 | 0.0400 (19) | 0.0288 (17) | 0.055 (12) | −0.0047 (12) | 0.022 (3) | −0.003 (3) |
C12 | 0.0322 (19) | 0.0328 (18) | 0.028 (10) | −0.0035 (12) | 0.002 (3) | −0.006 (3) |
C13 | 0.0273 (18) | 0.0292 (17) | 0.034 (10) | 0.0008 (13) | 0.012 (3) | 0.000 (3) |
N1—N2 | 1.362 (8) | C19—C18 | 1.381 (3) |
N1—C3 | 1.401 (7) | C18—H18 | 0.9300 |
N1—C14 | 1.440 (4) | C18—C17 | 1.364 (5) |
N2—C1 | 1.347 (4) | C17—H17 | 0.9300 |
N3—C1 | 1.327 (6) | C17—C16 | 1.379 (5) |
N3—C2 | 1.375 (7) | C16—H16 | 0.9300 |
C1—C8 | 1.480 (7) | C16—C15 | 1.389 (3) |
C2—C7 | 1.383 (7) | C15—H15 | 0.9300 |
C2—C3 | 1.420 (5) | C8—C9 | 1.393 (5) |
C7—H7 | 0.9300 | C8—C13 | 1.385 (7) |
C7—C6 | 1.360 (8) | C9—H9 | 0.9300 |
C6—H6 | 0.9300 | C9—C10 | 1.375 (8) |
C6—C5 | 1.397 (5) | C10—H10 | 0.9300 |
C5—H5 | 0.9300 | C10—C11 | 1.377 (7) |
C5—C4 | 1.370 (7) | C11—H11 | 0.9300 |
C4—H4 | 0.9300 | C11—C12 | 1.387 (4) |
C4—C3 | 1.386 (8) | C12—H12 | 0.9300 |
C14—C19 | 1.377 (5) | C12—C13 | 1.377 (8) |
C14—C15 | 1.373 (5) | C13—H13 | 0.9300 |
C19—H19 | 0.9300 | ||
N2—N1—C3 | 123.9 (3) | C18—C19—H19 | 120.3 |
N2—N1—C14 | 113.6 (5) | C19—C18—H18 | 120.0 |
C3—N1—C14 | 122.3 (5) | C17—C18—C19 | 120.1 (4) |
C1—N2—N1 | 115.6 (5) | C17—C18—H18 | 120.0 |
C1—N3—C2 | 116.9 (4) | C18—C17—H17 | 119.7 |
N2—C1—C8 | 114.4 (5) | C18—C17—C16 | 120.5 (3) |
N3—C1—N2 | 126.9 (6) | C16—C17—H17 | 119.7 |
N3—C1—C8 | 118.7 (4) | C17—C16—H16 | 120.0 |
N3—C2—C7 | 119.9 (4) | C17—C16—C15 | 120.0 (3) |
N3—C2—C3 | 121.9 (6) | C15—C16—H16 | 120.0 |
C7—C2—C3 | 118.2 (6) | C14—C15—C16 | 118.7 (4) |
C2—C7—H7 | 119.6 | C14—C15—H15 | 120.6 |
C6—C7—C2 | 120.8 (4) | C16—C15—H15 | 120.6 |
C6—C7—H7 | 119.6 | C9—C8—C1 | 118.7 (5) |
C7—C6—H6 | 119.6 | C13—C8—C1 | 122.4 (4) |
C7—C6—C5 | 120.9 (6) | C13—C8—C9 | 118.9 (6) |
C5—C6—H6 | 119.6 | C8—C9—H9 | 120.3 |
C6—C5—H5 | 120.1 | C10—C9—C8 | 119.4 (6) |
C4—C5—C6 | 119.8 (6) | C10—C9—H9 | 120.3 |
C4—C5—H5 | 120.1 | C9—C10—H10 | 119.2 |
C5—C4—H4 | 120.1 | C9—C10—C11 | 121.5 (4) |
C5—C4—C3 | 119.8 (4) | C11—C10—H10 | 119.2 |
C3—C4—H4 | 120.1 | C10—C11—H11 | 120.3 |
N1—C3—C2 | 114.8 (6) | C10—C11—C12 | 119.4 (6) |
C4—C3—N1 | 124.7 (4) | C12—C11—H11 | 120.3 |
C4—C3—C2 | 120.5 (5) | C11—C12—H12 | 120.3 |
C19—C14—N1 | 120.1 (3) | C13—C12—C11 | 119.4 (6) |
C15—C14—N1 | 118.6 (3) | C13—C12—H12 | 120.3 |
C15—C14—C19 | 121.3 (2) | C8—C13—H13 | 119.3 |
C14—C19—H19 | 120.3 | C12—C13—C8 | 121.4 (4) |
C14—C19—C18 | 119.4 (3) | C12—C13—H13 | 119.3 |
N1—N2—C1—N3 | 1.7 (4) | C7—C6—C5—C4 | −0.3 (4) |
N1—N2—C1—C8 | −177.5 (2) | C6—C5—C4—C3 | 0.5 (4) |
N1—C14—C19—C18 | 179.9 (5) | C5—C4—C3—N1 | 176.5 (2) |
N1—C14—C15—C16 | 180.0 (5) | C5—C4—C3—C2 | −0.2 (5) |
N2—N1—C3—C2 | 1.5 (4) | C3—N1—N2—C1 | −3.1 (5) |
N2—N1—C3—C4 | −175.4 (3) | C3—N1—C14—C19 | 55.7 (5) |
N2—N1—C14—C19 | −128.5 (5) | C3—N1—C14—C15 | −124.8 (5) |
N2—N1—C14—C15 | 51.0 (5) | C3—C2—C7—C6 | 0.6 (5) |
N2—C1—C8—C9 | 172.4 (2) | C14—N1—N2—C1 | −178.88 (19) |
N2—C1—C8—C13 | −7.1 (5) | C14—N1—C3—C2 | 176.8 (2) |
N3—C1—C8—C9 | −6.8 (4) | C14—N1—C3—C4 | 0.0 (5) |
N3—C1—C8—C13 | 173.6 (2) | C14—C19—C18—C17 | −0.4 (8) |
N3—C2—C7—C6 | −178.6 (3) | C19—C14—C15—C16 | −0.5 (8) |
N3—C2—C3—N1 | 1.8 (4) | C19—C18—C17—C16 | 0.5 (8) |
N3—C2—C3—C4 | 178.8 (3) | C18—C17—C16—C15 | −0.6 (8) |
C1—N3—C2—C7 | 176.0 (2) | C17—C16—C15—C14 | 0.6 (8) |
C1—N3—C2—C3 | −3.2 (4) | C15—C14—C19—C18 | 0.4 (8) |
C1—C8—C9—C10 | −179.1 (3) | C8—C9—C10—C11 | −1.0 (5) |
C1—C8—C13—C12 | −179.8 (3) | C9—C8—C13—C12 | 0.7 (5) |
C2—N3—C1—N2 | 1.4 (4) | C9—C10—C11—C12 | 0.5 (4) |
C2—N3—C1—C8 | −179.5 (2) | C10—C11—C12—C13 | 0.6 (4) |
C2—C7—C6—C5 | −0.3 (5) | C11—C12—C13—C8 | −1.2 (5) |
C7—C2—C3—N1 | −177.3 (3) | C13—C8—C9—C10 | 0.5 (4) |
C7—C2—C3—C4 | −0.4 (4) |
C19H14N3 | F(000) = 596 |
Mr = 284.33 | Dx = 1.605 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.1302 (4) Å | Cell parameters from 2011 reflections |
b = 6.2215 (3) Å | θ = 3.5–25.9° |
c = 18.9550 (18) Å | µ = 0.10 mm−1 |
β = 99.899 (5)° | T = 295 K |
V = 1176.85 (13) Å3 | Block, clear dark brown |
Z = 4 | 0.16 × 0.14 × 0.09 mm |
Bruker SMART APEX2 area detector diffractometer | 805 independent reflections |
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs | 558 reflections with I > 2σ(I) |
Mirror optics monochromator | Rint = 0.035 |
Detector resolution: 7.9 pixels mm-1 | θmax = 26.3°, θmin = 2.1° |
ω and φ scans | h = −12→12 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0569 before and 0.0430 after correction. The Ratio of minimum to maximum transmission is 0.8822. The λ/2 correction factor is Not present. | k = −7→7 |
Tmin = 0.658, Tmax = 0.745 | l = −8→8 |
5411 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.097 | w = 1/[σ2(Fo2) + (0.0665P)2 + 0.0073P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
805 reflections | Δρmax = 0.10 e Å−3 |
199 parameters | Δρmin = −0.11 e Å−3 |
231 restraints |
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. High pressure data collection in a diamond anvil cell. 3.4218 GPa. PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT432_ALERT_2_G Short Inter X···Y Contact C1 ..C9 3.16 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 3.07 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 3.19 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.11 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.15 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check Correct. H H contacts can be as short as 1.7 Ang. See Wood, Peter A., et al. "Analysis of the compression of molecular crystal structures using Hirshfeld surfaces." CrystEngComm 10.4 (2008): 368-376. PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 231 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 53 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ··· 3 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 15 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 15 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info No action taken. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.4740 (3) | 0.6901 (4) | 0.6613 (4) | 0.031 (3) | |
N2 | 0.4433 (2) | 0.6776 (4) | 0.7285 (4) | 0.032 (3) | |
N3 | 0.2112 (3) | 0.6706 (4) | 0.6774 (4) | 0.031 (4) | |
C1 | 0.3113 (3) | 0.6722 (4) | 0.7312 (4) | 0.027 (4) | |
C2 | 0.2436 (3) | 0.6725 (5) | 0.6100 (4) | 0.030 (4) | |
C7 | 0.1444 (3) | 0.6591 (4) | 0.5499 (4) | 0.029 (4) | |
H7 | 0.055091 | 0.651835 | 0.555559 | 0.035* | |
C6 | 0.1750 (3) | 0.6563 (4) | 0.4826 (4) | 0.032 (4) | |
H6 | 0.106866 | 0.645671 | 0.443033 | 0.039* | |
C5 | 0.3084 (3) | 0.6694 (3) | 0.4729 (4) | 0.033 (4) | |
H5 | 0.328989 | 0.667662 | 0.426908 | 0.039* | |
C4 | 0.4093 (3) | 0.6850 (5) | 0.5312 (4) | 0.032 (4) | |
H4 | 0.498085 | 0.694484 | 0.524809 | 0.039* | |
C3 | 0.3787 (3) | 0.6865 (5) | 0.5994 (4) | 0.029 (4) | |
C14 | 0.6152 (2) | 0.6930 (3) | 0.6609 (3) | 0.018 (3) | |
C19 | 0.6694 (2) | 0.8515 (3) | 0.6239 (4) | 0.026 (4) | |
H19 | 0.614485 | 0.956137 | 0.599012 | 0.032* | |
C18 | 0.8058 (2) | 0.8540 (4) | 0.6241 (4) | 0.043 (5) | |
H18 | 0.843087 | 0.962055 | 0.599882 | 0.051* | |
C17 | 0.8857 (2) | 0.6989 (4) | 0.6595 (3) | 0.038 (4) | |
H17 | 0.977311 | 0.700278 | 0.659063 | 0.045* | |
C16 | 0.8311 (2) | 0.5402 (4) | 0.6960 (4) | 0.033 (4) | |
H16 | 0.886268 | 0.433634 | 0.719514 | 0.039* | |
C15 | 0.6952 (2) | 0.5369 (4) | 0.6982 (3) | 0.030 (4) | |
H15 | 0.658787 | 0.432187 | 0.724200 | 0.036* | |
C8 | 0.2804 (3) | 0.6710 (4) | 0.8049 (4) | 0.029 (4) | |
C9 | 0.1464 (3) | 0.6910 (4) | 0.8128 (4) | 0.033 (4) | |
H9 | 0.078925 | 0.700642 | 0.772871 | 0.040* | |
C10 | 0.1165 (3) | 0.6961 (5) | 0.8810 (4) | 0.035 (4) | |
H10 | 0.027820 | 0.712569 | 0.886891 | 0.042* | |
C11 | 0.2143 (3) | 0.6775 (3) | 0.9402 (4) | 0.039 (4) | |
H11 | 0.191310 | 0.679733 | 0.985630 | 0.046* | |
C12 | 0.3474 (3) | 0.6554 (5) | 0.9329 (5) | 0.038 (4) | |
H12 | 0.414183 | 0.641357 | 0.972897 | 0.045* | |
C13 | 0.3786 (3) | 0.6547 (5) | 0.8648 (4) | 0.033 (4) | |
H13 | 0.467699 | 0.642918 | 0.859165 | 0.040* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0175 (14) | 0.0273 (11) | 0.052 (11) | −0.0002 (9) | 0.014 (3) | −0.003 (3) |
N2 | 0.0175 (14) | 0.0259 (11) | 0.054 (11) | −0.0008 (9) | 0.010 (3) | −0.004 (3) |
N3 | 0.0159 (15) | 0.0224 (11) | 0.053 (11) | 0.0001 (10) | 0.001 (3) | −0.004 (3) |
C1 | 0.0132 (15) | 0.0163 (12) | 0.051 (11) | 0.0010 (10) | 0.005 (3) | 0.001 (3) |
C2 | 0.0206 (18) | 0.0160 (12) | 0.054 (11) | 0.0028 (11) | 0.008 (3) | 0.001 (3) |
C7 | 0.0154 (15) | 0.0230 (13) | 0.050 (12) | 0.0015 (11) | 0.004 (3) | 0.000 (3) |
C6 | 0.0247 (18) | 0.0238 (13) | 0.049 (12) | 0.0007 (11) | 0.009 (3) | 0.000 (3) |
C5 | 0.0259 (15) | 0.0259 (13) | 0.047 (12) | −0.0010 (10) | 0.008 (3) | −0.003 (2) |
C4 | 0.0198 (17) | 0.0259 (13) | 0.053 (11) | −0.0029 (12) | 0.010 (3) | −0.001 (3) |
C3 | 0.0157 (16) | 0.0194 (12) | 0.052 (11) | −0.0004 (11) | 0.003 (3) | −0.003 (3) |
C14 | 0.0156 (12) | 0.0288 (13) | 0.010 (11) | −0.0004 (9) | 0.003 (2) | −0.006 (2) |
C19 | 0.0230 (13) | 0.0291 (13) | 0.027 (13) | −0.0013 (9) | 0.005 (3) | −0.001 (2) |
C18 | 0.0216 (14) | 0.0486 (16) | 0.059 (15) | −0.0093 (11) | 0.009 (3) | 0.001 (2) |
C17 | 0.0141 (13) | 0.0668 (19) | 0.032 (14) | 0.0006 (12) | 0.001 (3) | −0.003 (3) |
C16 | 0.0271 (14) | 0.0526 (17) | 0.014 (14) | 0.0152 (12) | −0.007 (3) | −0.002 (3) |
C15 | 0.0238 (13) | 0.0361 (14) | 0.031 (12) | 0.0035 (10) | 0.008 (3) | 0.001 (2) |
C8 | 0.0194 (17) | 0.0160 (12) | 0.052 (11) | −0.0023 (11) | 0.011 (3) | −0.004 (3) |
C9 | 0.0197 (17) | 0.0210 (12) | 0.060 (12) | −0.0022 (10) | 0.008 (3) | 0.006 (3) |
C10 | 0.0227 (16) | 0.0245 (13) | 0.061 (13) | −0.0044 (12) | 0.013 (3) | 0.000 (3) |
C11 | 0.0359 (17) | 0.0200 (12) | 0.062 (13) | −0.0025 (10) | 0.014 (3) | 0.005 (2) |
C12 | 0.0293 (19) | 0.0246 (13) | 0.058 (12) | −0.0021 (11) | 0.005 (4) | −0.003 (3) |
C13 | 0.0166 (15) | 0.0246 (13) | 0.057 (12) | −0.0009 (12) | 0.002 (3) | −0.003 (3) |
N1—N2 | 1.365 (8) | C19—C18 | 1.381 (3) |
N1—C3 | 1.386 (7) | C18—H18 | 0.9300 |
N1—C14 | 1.432 (3) | C18—C17 | 1.360 (5) |
N2—C1 | 1.347 (4) | C17—H17 | 0.9300 |
N3—C1 | 1.309 (7) | C17—C16 | 1.375 (5) |
N3—C2 | 1.372 (8) | C16—H16 | 0.9300 |
C1—C8 | 1.483 (8) | C16—C15 | 1.385 (3) |
C2—C7 | 1.387 (7) | C15—H15 | 0.9300 |
C2—C3 | 1.420 (5) | C8—C9 | 1.397 (5) |
C7—H7 | 0.9300 | C8—C13 | 1.377 (7) |
C7—C6 | 1.364 (8) | C9—H9 | 0.9300 |
C6—H6 | 0.9300 | C9—C10 | 1.378 (8) |
C6—C5 | 1.398 (4) | C10—H10 | 0.9300 |
C5—H5 | 0.9300 | C10—C11 | 1.368 (7) |
C5—C4 | 1.374 (7) | C11—H11 | 0.9300 |
C4—H4 | 0.9300 | C11—C12 | 1.386 (4) |
C4—C3 | 1.379 (8) | C12—H12 | 0.9300 |
C14—C19 | 1.377 (5) | C12—C13 | 1.381 (8) |
C14—C15 | 1.380 (5) | C13—H13 | 0.9300 |
C19—H19 | 0.9300 | ||
N2—N1—C3 | 123.5 (4) | C18—C19—H19 | 120.2 |
N2—N1—C14 | 113.2 (5) | C19—C18—H18 | 119.9 |
C3—N1—C14 | 123.1 (6) | C17—C18—C19 | 120.2 (4) |
C1—N2—N1 | 115.1 (6) | C17—C18—H18 | 119.9 |
C1—N3—C2 | 116.6 (4) | C18—C17—H17 | 120.0 |
N2—C1—C8 | 114.0 (5) | C18—C17—C16 | 120.1 (2) |
N3—C1—N2 | 127.7 (7) | C16—C17—H17 | 120.0 |
N3—C1—C8 | 118.2 (4) | C17—C16—H16 | 119.5 |
N3—C2—C7 | 120.6 (4) | C17—C16—C15 | 120.9 (3) |
N3—C2—C3 | 121.5 (6) | C15—C16—H16 | 119.5 |
C7—C2—C3 | 117.8 (6) | C14—C15—C16 | 118.2 (4) |
C2—C7—H7 | 119.3 | C14—C15—H15 | 120.9 |
C6—C7—C2 | 121.4 (4) | C16—C15—H15 | 120.9 |
C6—C7—H7 | 119.3 | C9—C8—C1 | 117.8 (5) |
C7—C6—H6 | 119.9 | C13—C8—C1 | 122.5 (4) |
C7—C6—C5 | 120.2 (6) | C13—C8—C9 | 119.7 (7) |
C5—C6—H6 | 119.9 | C8—C9—H9 | 120.8 |
C6—C5—H5 | 120.0 | C10—C9—C8 | 118.4 (6) |
C4—C5—C6 | 120.0 (6) | C10—C9—H9 | 120.8 |
C4—C5—H5 | 120.0 | C9—C10—H10 | 119.2 |
C5—C4—H4 | 120.0 | C11—C10—C9 | 121.5 (4) |
C5—C4—C3 | 119.9 (3) | C11—C10—H10 | 119.2 |
C3—C4—H4 | 120.0 | C10—C11—H11 | 119.8 |
N1—C3—C2 | 115.4 (6) | C10—C11—C12 | 120.4 (6) |
C4—C3—N1 | 123.8 (4) | C12—C11—H11 | 119.8 |
C4—C3—C2 | 120.7 (5) | C11—C12—H12 | 120.8 |
C19—C14—N1 | 119.8 (3) | C13—C12—C11 | 118.5 (6) |
C19—C14—C15 | 121.0 (2) | C13—C12—H12 | 120.8 |
C15—C14—N1 | 119.1 (3) | C8—C13—C12 | 121.4 (4) |
C14—C19—H19 | 120.2 | C8—C13—H13 | 119.3 |
C14—C19—C18 | 119.5 (3) | C12—C13—H13 | 119.3 |
N1—N2—C1—N3 | 2.3 (4) | C7—C6—C5—C4 | 0.1 (4) |
N1—N2—C1—C8 | −176.8 (3) | C6—C5—C4—C3 | 0.3 (5) |
N1—C14—C19—C18 | 179.6 (5) | C5—C4—C3—N1 | 176.4 (2) |
N1—C14—C15—C16 | 178.8 (5) | C5—C4—C3—C2 | −0.1 (6) |
N2—N1—C3—C2 | 1.1 (4) | C3—N1—N2—C1 | −3.2 (5) |
N2—N1—C3—C4 | −175.6 (3) | C3—N1—C14—C19 | 55.6 (5) |
N2—N1—C14—C19 | −128.3 (5) | C3—N1—C14—C15 | −125.0 (5) |
N2—N1—C14—C15 | 51.2 (5) | C3—C2—C7—C6 | 0.9 (5) |
N2—C1—C8—C9 | 172.6 (2) | C14—N1—N2—C1 | −179.31 (18) |
N2—C1—C8—C13 | −6.3 (5) | C14—N1—C3—C2 | 176.8 (2) |
N3—C1—C8—C9 | −6.6 (4) | C14—N1—C3—C4 | 0.1 (5) |
N3—C1—C8—C13 | 174.5 (2) | C14—C19—C18—C17 | 1.1 (8) |
N3—C2—C7—C6 | −178.6 (3) | C19—C14—C15—C16 | −1.7 (8) |
N3—C2—C3—N1 | 2.2 (5) | C19—C18—C17—C16 | −0.7 (8) |
N3—C2—C3—C4 | 179.0 (3) | C18—C17—C16—C15 | −0.9 (8) |
C1—N3—C2—C7 | 176.4 (2) | C17—C16—C15—C14 | 2.1 (8) |
C1—N3—C2—C3 | −3.0 (5) | C15—C14—C19—C18 | 0.2 (8) |
C1—C8—C9—C10 | −178.2 (3) | C8—C9—C10—C11 | −1.4 (5) |
C1—C8—C13—C12 | 179.6 (3) | C9—C8—C13—C12 | 0.7 (5) |
C2—N3—C1—N2 | 0.7 (5) | C9—C10—C11—C12 | 0.8 (4) |
C2—N3—C1—C8 | 179.8 (3) | C10—C11—C12—C13 | 0.6 (4) |
C2—C7—C6—C5 | −0.7 (5) | C11—C12—C13—C8 | −1.3 (5) |
C7—C2—C3—N1 | −177.3 (2) | C13—C8—C9—C10 | 0.7 (4) |
C7—C2—C3—C4 | −0.5 (5) |
C19H14N3 | F(000) = 596 |
Mr = 284.33 | Dx = 1.638 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.0953 (4) Å | Cell parameters from 1769 reflections |
b = 6.1527 (3) Å | θ = 3.5–25.5° |
c = 18.8502 (18) Å | µ = 0.10 mm−1 |
β = 99.934 (5)° | T = 271 K |
V = 1153.29 (13) Å3 | Block, clear dark brown |
Z = 4 | 0.16 × 0.14 × 0.09 mm |
Bruker SMART APEX2 area detector diffractometer | 772 independent reflections |
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs | 518 reflections with I > 2σ(I) |
Mirror optics monochromator | Rint = 0.043 |
Detector resolution: 7.9 pixels mm-1 | θmax = 26.4°, θmin = 2.2° |
ω and φ scans | h = −11→11 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0612 before and 0.0433 after correction. The Ratio of minimum to maximum transmission is 0.9141. The λ/2 correction factor is Not present. | k = −7→7 |
Tmin = 0.681, Tmax = 0.745 | l = −8→8 |
6509 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.096 | w = 1/[σ2(Fo2) + (0.0535P)2 + 0.2042P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
772 reflections | Δρmax = 0.11 e Å−3 |
199 parameters | Δρmin = −0.11 e Å−3 |
231 restraints |
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. High pressure data collection in a diamond anvil cell. 4.0054 GPa. PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT432_ALERT_2_G Short Inter X···Y Contact C1 ..C9 3.13 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C2 ..C12 3.19 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 3.02 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 3.16 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.07 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.11 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check Correct. H H contacts can be as short as 1.7 Ang. See Wood, Peter A., et al. "Analysis of the compression of molecular crystal structures using Hirshfeld surfaces." CrystEngComm 10.4 (2008): 368-376. PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 231 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 52 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ··· 3 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 15 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 15 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info No action taken. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.4745 (3) | 0.6858 (4) | 0.6626 (4) | 0.030 (4) | |
N2 | 0.4435 (3) | 0.6713 (4) | 0.7299 (4) | 0.030 (4) | |
N3 | 0.2099 (3) | 0.6652 (4) | 0.6780 (5) | 0.028 (4) | |
C1 | 0.3116 (3) | 0.6656 (4) | 0.7323 (5) | 0.024 (4) | |
C2 | 0.2427 (4) | 0.6687 (5) | 0.6107 (5) | 0.025 (4) | |
C7 | 0.1437 (4) | 0.6565 (5) | 0.5498 (5) | 0.029 (4) | |
H7 | 0.054182 | 0.648274 | 0.555454 | 0.035* | |
C6 | 0.1735 (3) | 0.6563 (5) | 0.4819 (5) | 0.030 (4) | |
H6 | 0.104906 | 0.646806 | 0.442158 | 0.036* | |
C5 | 0.3082 (3) | 0.6705 (4) | 0.4721 (4) | 0.032 (4) | |
H5 | 0.329117 | 0.669836 | 0.425899 | 0.038* | |
C4 | 0.4092 (4) | 0.6854 (5) | 0.5314 (5) | 0.030 (4) | |
H4 | 0.498270 | 0.696908 | 0.525152 | 0.036* | |
C3 | 0.3785 (3) | 0.6833 (5) | 0.6002 (4) | 0.027 (4) | |
C14 | 0.6159 (2) | 0.6893 (4) | 0.6619 (3) | 0.018 (4) | |
C19 | 0.6696 (3) | 0.8518 (4) | 0.6259 (4) | 0.021 (4) | |
H19 | 0.614260 | 0.959046 | 0.601853 | 0.025* | |
C18 | 0.8058 (3) | 0.8553 (5) | 0.6254 (4) | 0.043 (5) | |
H18 | 0.842627 | 0.965103 | 0.601032 | 0.052* | |
C17 | 0.8869 (3) | 0.6982 (5) | 0.6607 (4) | 0.033 (4) | |
H17 | 0.979069 | 0.701891 | 0.660819 | 0.040* | |
C16 | 0.8326 (3) | 0.5343 (5) | 0.6962 (4) | 0.039 (5) | |
H16 | 0.887926 | 0.425940 | 0.719492 | 0.046* | |
C15 | 0.6958 (2) | 0.5299 (5) | 0.6973 (4) | 0.032 (4) | |
H15 | 0.658899 | 0.420348 | 0.721777 | 0.038* | |
C8 | 0.2798 (3) | 0.6664 (4) | 0.8061 (5) | 0.023 (4) | |
C9 | 0.1453 (3) | 0.6855 (5) | 0.8142 (4) | 0.033 (4) | |
H9 | 0.077025 | 0.692110 | 0.774257 | 0.040* | |
C10 | 0.1162 (4) | 0.6943 (5) | 0.8834 (4) | 0.035 (4) | |
H10 | 0.027378 | 0.713032 | 0.889449 | 0.042* | |
C11 | 0.2141 (3) | 0.6761 (4) | 0.9430 (5) | 0.036 (4) | |
H11 | 0.191675 | 0.679110 | 0.988778 | 0.044* | |
C12 | 0.3469 (3) | 0.6533 (5) | 0.9346 (5) | 0.029 (4) | |
H12 | 0.414330 | 0.640203 | 0.974729 | 0.035* | |
C13 | 0.3783 (4) | 0.6503 (5) | 0.8668 (5) | 0.027 (4) | |
H13 | 0.467811 | 0.637045 | 0.861388 | 0.032* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0183 (16) | 0.0282 (13) | 0.045 (11) | −0.0003 (11) | 0.013 (3) | −0.001 (3) |
N2 | 0.0157 (16) | 0.0280 (13) | 0.047 (11) | −0.0022 (10) | 0.005 (3) | −0.005 (3) |
N3 | 0.0180 (17) | 0.0233 (13) | 0.043 (11) | 0.0000 (12) | 0.005 (3) | −0.004 (3) |
C1 | 0.0153 (17) | 0.0152 (14) | 0.041 (11) | 0.0004 (12) | 0.007 (3) | −0.001 (3) |
C2 | 0.0172 (19) | 0.0151 (14) | 0.041 (12) | 0.0032 (12) | 0.003 (3) | 0.005 (4) |
C7 | 0.0179 (18) | 0.0227 (16) | 0.044 (12) | 0.0011 (13) | −0.001 (3) | 0.003 (4) |
C6 | 0.026 (2) | 0.0233 (16) | 0.037 (13) | −0.0002 (13) | −0.002 (4) | 0.001 (4) |
C5 | 0.0239 (17) | 0.0260 (15) | 0.044 (12) | −0.0014 (11) | 0.004 (3) | 0.000 (3) |
C4 | 0.0182 (18) | 0.0255 (15) | 0.048 (12) | −0.0011 (13) | 0.008 (3) | −0.004 (4) |
C3 | 0.0156 (18) | 0.0165 (14) | 0.047 (11) | −0.0002 (12) | 0.003 (3) | −0.006 (4) |
C14 | 0.0116 (13) | 0.0293 (15) | 0.012 (12) | 0.0000 (11) | 0.000 (3) | −0.005 (2) |
C19 | 0.0195 (15) | 0.0313 (16) | 0.011 (14) | −0.0018 (10) | 0.000 (3) | −0.004 (2) |
C18 | 0.0213 (16) | 0.0467 (19) | 0.062 (17) | −0.0085 (12) | 0.006 (4) | 0.008 (3) |
C17 | 0.0162 (14) | 0.062 (2) | 0.022 (14) | −0.0004 (14) | 0.006 (3) | −0.008 (3) |
C16 | 0.0250 (16) | 0.053 (2) | 0.034 (15) | 0.0151 (14) | −0.005 (4) | 0.003 (3) |
C15 | 0.0243 (15) | 0.0370 (17) | 0.035 (14) | 0.0033 (11) | 0.006 (3) | 0.009 (3) |
C8 | 0.0142 (18) | 0.0164 (14) | 0.039 (11) | 0.0013 (12) | 0.006 (3) | −0.003 (4) |
C9 | 0.0206 (19) | 0.0213 (15) | 0.057 (13) | −0.0022 (12) | 0.005 (3) | 0.002 (4) |
C10 | 0.0205 (18) | 0.0235 (16) | 0.062 (13) | −0.0040 (13) | 0.008 (4) | −0.003 (3) |
C11 | 0.0301 (18) | 0.0202 (15) | 0.060 (14) | −0.0032 (12) | 0.012 (3) | −0.001 (3) |
C12 | 0.027 (2) | 0.0242 (16) | 0.035 (13) | −0.0015 (13) | −0.002 (4) | −0.004 (4) |
C13 | 0.0174 (18) | 0.0229 (16) | 0.041 (12) | 0.0037 (13) | 0.006 (3) | −0.006 (3) |
N1—N2 | 1.359 (8) | C19—C18 | 1.377 (3) |
N1—C3 | 1.390 (7) | C18—H18 | 0.9300 |
N1—C14 | 1.430 (4) | C18—C17 | 1.364 (6) |
N2—C1 | 1.341 (4) | C17—H17 | 0.9300 |
N3—C1 | 1.318 (7) | C17—C16 | 1.375 (6) |
N3—C2 | 1.367 (8) | C16—H16 | 0.9300 |
C1—C8 | 1.481 (8) | C16—C15 | 1.385 (3) |
C2—C7 | 1.388 (8) | C15—H15 | 0.9300 |
C2—C3 | 1.421 (5) | C8—C9 | 1.398 (5) |
C7—H7 | 0.9300 | C8—C13 | 1.384 (8) |
C7—C6 | 1.365 (9) | C9—H9 | 0.9300 |
C6—H6 | 0.9300 | C9—C10 | 1.386 (8) |
C6—C5 | 1.406 (5) | C10—H10 | 0.9300 |
C5—H5 | 0.9300 | C10—C11 | 1.367 (8) |
C5—C4 | 1.380 (7) | C11—H11 | 0.9300 |
C4—H4 | 0.9300 | C11—C12 | 1.384 (4) |
C4—C3 | 1.383 (8) | C12—H12 | 0.9300 |
C14—C19 | 1.372 (5) | C12—C13 | 1.369 (8) |
C14—C15 | 1.369 (5) | C13—H13 | 0.9300 |
C19—H19 | 0.9300 | ||
N2—N1—C3 | 123.4 (4) | C18—C19—H19 | 120.2 |
N2—N1—C14 | 113.6 (5) | C19—C18—H18 | 119.9 |
C3—N1—C14 | 122.9 (6) | C17—C18—C19 | 120.2 (4) |
C1—N2—N1 | 115.0 (6) | C17—C18—H18 | 119.9 |
C1—N3—C2 | 116.0 (4) | C18—C17—H17 | 120.0 |
N2—C1—C8 | 114.1 (6) | C18—C17—C16 | 120.0 (3) |
N3—C1—N2 | 128.3 (7) | C16—C17—H17 | 120.0 |
N3—C1—C8 | 117.6 (4) | C17—C16—H16 | 119.9 |
N3—C2—C7 | 120.8 (4) | C17—C16—C15 | 120.3 (3) |
N3—C2—C3 | 121.7 (6) | C15—C16—H16 | 119.9 |
C7—C2—C3 | 117.5 (6) | C14—C15—C16 | 119.0 (4) |
C2—C7—H7 | 118.9 | C14—C15—H15 | 120.5 |
C6—C7—C2 | 122.2 (4) | C16—C15—H15 | 120.5 |
C6—C7—H7 | 118.9 | C9—C8—C1 | 118.4 (6) |
C7—C6—H6 | 120.1 | C13—C8—C1 | 122.4 (4) |
C7—C6—C5 | 119.9 (6) | C13—C8—C9 | 119.2 (7) |
C5—C6—H6 | 120.1 | C8—C9—H9 | 120.8 |
C6—C5—H5 | 120.2 | C10—C9—C8 | 118.3 (6) |
C4—C5—C6 | 119.5 (6) | C10—C9—H9 | 120.8 |
C4—C5—H5 | 120.2 | C9—C10—H10 | 119.0 |
C5—C4—H4 | 119.8 | C11—C10—C9 | 121.9 (4) |
C5—C4—C3 | 120.4 (4) | C11—C10—H10 | 119.0 |
C3—C4—H4 | 119.8 | C10—C11—H11 | 120.3 |
N1—C3—C2 | 115.5 (6) | C10—C11—C12 | 119.5 (7) |
C4—C3—N1 | 123.9 (4) | C12—C11—H11 | 120.3 |
C4—C3—C2 | 120.5 (6) | C11—C12—H12 | 120.2 |
C19—C14—N1 | 119.8 (3) | C13—C12—C11 | 119.5 (6) |
C15—C14—N1 | 119.4 (3) | C13—C12—H12 | 120.2 |
C15—C14—C19 | 120.9 (2) | C8—C13—H13 | 119.3 |
C14—C19—H19 | 120.2 | C12—C13—C8 | 121.4 (4) |
C14—C19—C18 | 119.7 (4) | C12—C13—H13 | 119.3 |
N1—N2—C1—N3 | 2.4 (5) | C7—C6—C5—C4 | −0.3 (4) |
N1—N2—C1—C8 | −175.7 (3) | C6—C5—C4—C3 | 0.9 (5) |
N1—C14—C19—C18 | 179.7 (6) | C5—C4—C3—N1 | 176.4 (2) |
N1—C14—C15—C16 | 179.9 (5) | C5—C4—C3—C2 | −0.8 (6) |
N2—N1—C3—C2 | 1.2 (5) | C3—N1—N2—C1 | −3.3 (5) |
N2—N1—C3—C4 | −176.1 (3) | C3—N1—C14—C19 | 56.4 (6) |
N2—N1—C14—C19 | −127.5 (5) | C3—N1—C14—C15 | −123.7 (5) |
N2—N1—C14—C15 | 52.4 (6) | C3—C2—C7—C6 | 0.6 (5) |
N2—C1—C8—C9 | 172.9 (2) | C14—N1—N2—C1 | −179.4 (2) |
N2—C1—C8—C13 | −6.7 (4) | C14—N1—C3—C2 | 176.9 (2) |
N3—C1—C8—C9 | −5.4 (4) | C14—N1—C3—C4 | −0.5 (5) |
N3—C1—C8—C13 | 175.0 (2) | C14—C19—C18—C17 | −0.1 (9) |
N3—C2—C7—C6 | −179.0 (3) | C19—C14—C15—C16 | −0.2 (9) |
N3—C2—C3—N1 | 2.2 (5) | C19—C18—C17—C16 | 0.7 (9) |
N3—C2—C3—C4 | 179.7 (4) | C18—C17—C16—C15 | −1.1 (9) |
C1—N3—C2—C7 | 176.4 (2) | C17—C16—C15—C14 | 0.8 (8) |
C1—N3—C2—C3 | −3.2 (5) | C15—C14—C19—C18 | −0.2 (9) |
C1—C8—C9—C10 | −177.7 (3) | C8—C9—C10—C11 | −2.6 (5) |
C1—C8—C13—C12 | 179.4 (3) | C9—C8—C13—C12 | −0.2 (5) |
C2—N3—C1—N2 | 0.8 (5) | C9—C10—C11—C12 | 1.5 (5) |
C2—N3—C1—C8 | 178.8 (3) | C10—C11—C12—C13 | 0.3 (5) |
C2—C7—C6—C5 | −0.5 (5) | C11—C12—C13—C8 | −0.9 (5) |
C7—C2—C3—N1 | −177.4 (3) | C13—C8—C9—C10 | 2.0 (4) |
C7—C2—C3—C4 | 0.1 (5) |
C19H14N3 | F(000) = 596 |
Mr = 284.33 | Dx = 1.670 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.0607 (6) Å | Cell parameters from 2047 reflections |
b = 6.0918 (4) Å | θ = 3.5–25.7° |
c = 18.733 (3) Å | µ = 0.10 mm−1 |
β = 99.951 (7)° | T = 271 K |
V = 1130.84 (19) Å3 | Block, clear dark brown |
Z = 4 | 0.16 × 0.14 × 0.09 mm |
Bruker SMART APEX2 area detector diffractometer | 758 independent reflections |
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs | 553 reflections with I > 2σ(I) |
Mirror optics monochromator | Rint = 0.037 |
Detector resolution: 7.9 pixels mm-1 | θmax = 26.4°, θmin = 2.2° |
ω and φ scans | h = −12→12 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0643 before and 0.0459 after correction. The Ratio of minimum to maximum transmission is 0.8964. The λ/2 correction factor is Not present. | k = −7→7 |
Tmin = 0.668, Tmax = 0.745 | l = −7→7 |
6290 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.107 | w = 1/[σ2(Fo2) + (0.062P)2 + 0.2883P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max < 0.001 |
758 reflections | Δρmax = 0.12 e Å−3 |
199 parameters | Δρmin = −0.15 e Å−3 |
231 restraints |
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. High pressure data collection in a diamond anvil cell. 4.7574 GPa. PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT432_ALERT_2_G Short Inter X···Y Contact C1 ..C9 3.13 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C2 ..C12 3.17 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 2.99 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 3.13 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.02 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.09 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check Correct. H H contacts can be as short as 1.7 Ang. See Wood, Peter A., et al. "Analysis of the compression of molecular crystal structures using Hirshfeld surfaces." CrystEngComm 10.4 (2008): 368-376. PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 231 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 49 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ··· 4 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 16 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 16 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info No action taken. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.4738 (3) | 0.6808 (4) | 0.6636 (4) | 0.023 (4) | |
N2 | 0.4433 (3) | 0.6638 (4) | 0.7314 (4) | 0.023 (4) | |
N3 | 0.2093 (3) | 0.6601 (4) | 0.6793 (4) | 0.024 (4) | |
C1 | 0.3106 (3) | 0.6602 (5) | 0.7339 (5) | 0.017 (4) | |
C2 | 0.2422 (4) | 0.6650 (5) | 0.6111 (5) | 0.019 (4) | |
C7 | 0.1424 (3) | 0.6543 (5) | 0.5501 (5) | 0.020 (4) | |
H7 | 0.052484 | 0.646924 | 0.555707 | 0.024* | |
C6 | 0.1737 (3) | 0.6543 (5) | 0.4817 (5) | 0.021 (4) | |
H6 | 0.105376 | 0.643102 | 0.441526 | 0.025* | |
C5 | 0.3081 (3) | 0.6712 (4) | 0.4722 (4) | 0.025 (4) | |
H5 | 0.328635 | 0.673012 | 0.425630 | 0.030* | |
C4 | 0.4101 (3) | 0.6852 (5) | 0.5312 (5) | 0.023 (4) | |
H4 | 0.499515 | 0.697153 | 0.524910 | 0.027* | |
C3 | 0.3781 (3) | 0.6812 (5) | 0.6000 (4) | 0.020 (4) | |
C14 | 0.6163 (2) | 0.6855 (4) | 0.6625 (4) | 0.019 (4) | |
C19 | 0.6693 (3) | 0.8531 (4) | 0.6274 (4) | 0.024 (5) | |
H19 | 0.613093 | 0.962185 | 0.604185 | 0.029* | |
C18 | 0.8060 (3) | 0.8595 (5) | 0.6266 (5) | 0.030 (5) | |
H18 | 0.842481 | 0.973355 | 0.603131 | 0.036* | |
C17 | 0.8873 (3) | 0.6987 (5) | 0.6603 (4) | 0.040 (5) | |
H17 | 0.979573 | 0.703050 | 0.659777 | 0.047* | |
C16 | 0.8343 (3) | 0.5295 (5) | 0.6952 (5) | 0.035 (5) | |
H16 | 0.890765 | 0.419456 | 0.717513 | 0.042* | |
C15 | 0.6975 (3) | 0.5221 (4) | 0.6972 (4) | 0.030 (5) | |
H15 | 0.661297 | 0.409560 | 0.721399 | 0.036* | |
C8 | 0.2788 (3) | 0.6595 (5) | 0.8078 (5) | 0.020 (4) | |
C9 | 0.1442 (3) | 0.6804 (5) | 0.8168 (5) | 0.023 (4) | |
H9 | 0.075347 | 0.686190 | 0.776712 | 0.028* | |
C10 | 0.1154 (4) | 0.6924 (5) | 0.8861 (4) | 0.024 (4) | |
H10 | 0.026559 | 0.713327 | 0.892338 | 0.029* | |
C11 | 0.2143 (3) | 0.6743 (4) | 0.9456 (5) | 0.029 (4) | |
H11 | 0.192330 | 0.679025 | 0.991789 | 0.035* | |
C12 | 0.3472 (3) | 0.6488 (5) | 0.9372 (5) | 0.027 (4) | |
H12 | 0.414887 | 0.633049 | 0.977502 | 0.032* | |
C13 | 0.3783 (4) | 0.6471 (5) | 0.8684 (5) | 0.023 (4) | |
H13 | 0.468157 | 0.637459 | 0.862687 | 0.028* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0179 (15) | 0.0244 (12) | 0.030 (11) | 0.0000 (11) | 0.010 (3) | 0.002 (3) |
N2 | 0.0180 (16) | 0.0249 (12) | 0.027 (11) | −0.0027 (10) | 0.007 (3) | −0.002 (3) |
N3 | 0.0190 (16) | 0.0220 (12) | 0.029 (12) | 0.0006 (11) | −0.002 (3) | 0.003 (3) |
C1 | 0.0145 (16) | 0.0135 (12) | 0.021 (12) | 0.0002 (11) | 0.001 (3) | 0.000 (3) |
C2 | 0.0191 (19) | 0.0119 (12) | 0.026 (12) | 0.0023 (12) | 0.001 (3) | −0.001 (3) |
C7 | 0.0157 (17) | 0.0230 (14) | 0.023 (13) | 0.0030 (12) | 0.008 (3) | 0.001 (3) |
C6 | 0.0205 (18) | 0.0218 (14) | 0.020 (13) | −0.0007 (12) | 0.001 (4) | −0.007 (3) |
C5 | 0.0266 (17) | 0.0222 (13) | 0.028 (12) | 0.0002 (11) | 0.007 (3) | 0.004 (2) |
C4 | 0.0183 (17) | 0.0243 (13) | 0.029 (12) | −0.0012 (13) | 0.011 (3) | −0.004 (3) |
C3 | 0.0130 (17) | 0.0151 (12) | 0.030 (12) | 0.0005 (12) | 0.001 (3) | −0.002 (3) |
C14 | 0.0139 (13) | 0.0273 (13) | 0.015 (12) | −0.0008 (10) | 0.002 (3) | −0.004 (2) |
C19 | 0.0229 (15) | 0.0286 (15) | 0.021 (16) | −0.0007 (11) | 0.004 (4) | −0.001 (2) |
C18 | 0.0208 (15) | 0.0463 (18) | 0.025 (17) | −0.0096 (12) | 0.009 (4) | 0.001 (3) |
C17 | 0.0133 (14) | 0.064 (2) | 0.040 (17) | 0.0003 (14) | −0.001 (3) | −0.002 (3) |
C16 | 0.0263 (16) | 0.0485 (19) | 0.026 (17) | 0.0160 (14) | −0.004 (4) | 0.003 (3) |
C15 | 0.0242 (15) | 0.0332 (16) | 0.034 (15) | 0.0040 (11) | 0.007 (3) | 0.000 (3) |
C8 | 0.0197 (18) | 0.0159 (13) | 0.026 (12) | −0.0012 (12) | 0.011 (3) | 0.007 (3) |
C9 | 0.0187 (18) | 0.0186 (13) | 0.034 (13) | −0.0008 (11) | 0.007 (3) | 0.002 (3) |
C10 | 0.0207 (17) | 0.0199 (13) | 0.032 (13) | −0.0021 (13) | 0.005 (3) | −0.003 (3) |
C11 | 0.0320 (18) | 0.0196 (13) | 0.036 (14) | −0.0023 (12) | 0.006 (4) | 0.003 (3) |
C12 | 0.0266 (19) | 0.0223 (14) | 0.031 (13) | 0.0004 (12) | 0.003 (4) | 0.008 (3) |
C13 | 0.0183 (17) | 0.0219 (14) | 0.030 (13) | −0.0008 (13) | 0.005 (3) | 0.003 (3) |
N1—N2 | 1.362 (8) | C19—C18 | 1.379 (4) |
N1—C3 | 1.396 (8) | C18—H18 | 0.9300 |
N1—C14 | 1.438 (4) | C18—C17 | 1.360 (6) |
N2—C1 | 1.344 (4) | C17—H17 | 0.9300 |
N3—C1 | 1.313 (7) | C17—C16 | 1.376 (6) |
N3—C2 | 1.376 (8) | C16—H16 | 0.9300 |
C1—C8 | 1.473 (8) | C16—C15 | 1.384 (4) |
C2—C7 | 1.385 (8) | C15—H15 | 0.9300 |
C2—C3 | 1.421 (5) | C8—C9 | 1.399 (5) |
C7—H7 | 0.9300 | C8—C13 | 1.380 (8) |
C7—C6 | 1.372 (8) | C9—H9 | 0.9300 |
C6—H6 | 0.9300 | C9—C10 | 1.380 (8) |
C6—C5 | 1.397 (5) | C10—H10 | 0.9300 |
C5—H5 | 0.9300 | C10—C11 | 1.365 (8) |
C5—C4 | 1.376 (7) | C11—H11 | 0.9300 |
C4—H4 | 0.9300 | C11—C12 | 1.382 (5) |
C4—C3 | 1.382 (8) | C12—H12 | 0.9300 |
C14—C19 | 1.371 (5) | C12—C13 | 1.378 (9) |
C14—C15 | 1.377 (5) | C13—H13 | 0.9300 |
C19—H19 | 0.9300 | ||
N2—N1—C3 | 124.2 (4) | C18—C19—H19 | 120.1 |
N2—N1—C14 | 113.6 (5) | C19—C18—H18 | 120.1 |
C3—N1—C14 | 122.1 (6) | C17—C18—C19 | 119.7 (4) |
C1—N2—N1 | 114.8 (6) | C17—C18—H18 | 120.1 |
C1—N3—C2 | 116.4 (4) | C18—C17—H17 | 119.7 |
N2—C1—C8 | 114.3 (6) | C18—C17—C16 | 120.6 (3) |
N3—C1—N2 | 128.0 (7) | C16—C17—H17 | 119.7 |
N3—C1—C8 | 117.8 (4) | C17—C16—H16 | 119.8 |
N3—C2—C7 | 120.6 (4) | C17—C16—C15 | 120.4 (4) |
N3—C2—C3 | 121.9 (6) | C15—C16—H16 | 119.8 |
C7—C2—C3 | 117.5 (6) | C14—C15—C16 | 118.3 (4) |
C2—C7—H7 | 119.4 | C14—C15—H15 | 120.8 |
C6—C7—C2 | 121.3 (4) | C16—C15—H15 | 120.8 |
C6—C7—H7 | 119.4 | C9—C8—C1 | 119.0 (6) |
C7—C6—H6 | 119.9 | C13—C8—C1 | 121.9 (4) |
C7—C6—C5 | 120.2 (6) | C13—C8—C9 | 119.0 (7) |
C5—C6—H6 | 119.9 | C8—C9—H9 | 120.5 |
C6—C5—H5 | 119.8 | C10—C9—C8 | 118.9 (6) |
C4—C5—C6 | 120.4 (6) | C10—C9—H9 | 120.5 |
C4—C5—H5 | 119.8 | C9—C10—H10 | 119.3 |
C5—C4—H4 | 120.4 | C11—C10—C9 | 121.5 (4) |
C5—C4—C3 | 119.2 (4) | C11—C10—H10 | 119.3 |
C3—C4—H4 | 120.4 | C10—C11—H11 | 120.0 |
N1—C3—C2 | 114.5 (6) | C10—C11—C12 | 120.0 (7) |
C4—C3—N1 | 123.9 (4) | C12—C11—H11 | 120.0 |
C4—C3—C2 | 121.5 (6) | C11—C12—H12 | 120.4 |
C19—C14—N1 | 119.5 (3) | C13—C12—C11 | 119.2 (6) |
C19—C14—C15 | 121.1 (2) | C13—C12—H12 | 120.4 |
C15—C14—N1 | 119.4 (3) | C8—C13—H13 | 119.3 |
C14—C19—H19 | 120.1 | C12—C13—C8 | 121.3 (4) |
C14—C19—C18 | 119.8 (4) | C12—C13—H13 | 119.3 |
N1—N2—C1—N3 | 3.7 (5) | C7—C6—C5—C4 | 0.8 (4) |
N1—N2—C1—C8 | −175.4 (3) | C6—C5—C4—C3 | 0.3 (5) |
N1—C14—C19—C18 | 179.5 (6) | C5—C4—C3—N1 | 175.9 (2) |
N1—C14—C15—C16 | 179.7 (6) | C5—C4—C3—C2 | −0.6 (6) |
N2—N1—C3—C2 | 0.8 (5) | C3—N1—N2—C1 | −3.9 (5) |
N2—N1—C3—C4 | −175.9 (3) | C3—N1—C14—C19 | 56.8 (6) |
N2—N1—C14—C19 | −126.6 (5) | C3—N1—C14—C15 | −123.6 (6) |
N2—N1—C14—C15 | 53.0 (6) | C3—C2—C7—C6 | 1.4 (5) |
N2—C1—C8—C9 | 173.0 (2) | C14—N1—N2—C1 | 179.6 (2) |
N2—C1—C8—C13 | −4.5 (5) | C14—N1—C3—C2 | 177.0 (2) |
N3—C1—C8—C9 | −6.2 (4) | C14—N1—C3—C4 | 0.3 (5) |
N3—C1—C8—C13 | 176.3 (2) | C14—C19—C18—C17 | 0.4 (10) |
N3—C2—C7—C6 | −178.6 (3) | C19—C14—C15—C16 | −0.7 (9) |
N3—C2—C3—N1 | 3.0 (5) | C19—C18—C17—C16 | 0.0 (10) |
N3—C2—C3—C4 | 179.8 (3) | C18—C17—C16—C15 | −0.8 (10) |
C1—N3—C2—C7 | 176.8 (2) | C17—C16—C15—C14 | 1.1 (10) |
C1—N3—C2—C3 | −3.3 (5) | C15—C14—C19—C18 | −0.1 (10) |
C1—C8—C9—C10 | −176.3 (3) | C8—C9—C10—C11 | −3.0 (5) |
C1—C8—C13—C12 | 179.3 (3) | C9—C8—C13—C12 | 1.8 (5) |
C2—N3—C1—N2 | −0.3 (5) | C9—C10—C11—C12 | 1.7 (5) |
C2—N3—C1—C8 | 178.8 (3) | C10—C11—C12—C13 | 1.5 (5) |
C2—C7—C6—C5 | −1.7 (5) | C11—C12—C13—C8 | −3.2 (6) |
C7—C2—C3—N1 | −177.1 (3) | C13—C8—C9—C10 | 1.3 (5) |
C7—C2—C3—C4 | −0.3 (5) |
C19H14N3 | F(000) = 596 |
Mr = 284.33 | Dx = 1.700 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.0326 (6) Å | Cell parameters from 2046 reflections |
b = 6.0553 (4) Å | θ = 3.6–25.8° |
c = 18.571 (3) Å | µ = 0.10 mm−1 |
β = 100.029 (7)° | T = 291 K |
V = 1110.93 (19) Å3 | Block, clear dark brown |
Z = 4 | 0.16 × 0.14 × 0.09 mm |
Bruker SMART APEX2 area detector diffractometer | 748 independent reflections |
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs | 537 reflections with I > 2σ(I) |
Mirror optics monochromator | Rint = 0.043 |
Detector resolution: 7.9 pixels mm-1 | θmax = 26.3°, θmin = 2.2° |
ω and φ scans | h = −12→12 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0995 before and 0.0536 after correction. The Ratio of minimum to maximum transmission is 0.8569. The λ/2 correction factor is Not present. | k = −7→7 |
Tmin = 0.639, Tmax = 0.745 | l = −7→7 |
6150 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.102 | w = 1/[σ2(Fo2) + (0.0612P)2 + 0.1943P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
748 reflections | Δρmax = 0.12 e Å−3 |
199 parameters | Δρmin = −0.15 e Å−3 |
231 restraints |
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. High pressure data collection in a diamond anvil cell. 5.3436 GPa. PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT432_ALERT_2_G Short Inter X···Y Contact N3 ..C8 3.02 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact N3 ..C8 3.04 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C1 ..C9 3.13 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C2 ..C10 3.17 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C2 ..C13 3.18 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C2 ..C12 3.19 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 2.94 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 3.12 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.01 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.05 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check Correct. H H contacts can be as short as 1.7 Ang. See Wood, Peter A., et al. "Analysis of the compression of molecular crystal structures using Hirshfeld surfaces." CrystEngComm 10.4 (2008): 368-376. PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 231 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 49 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ··· 1 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 16 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 16 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info No action taken. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.4747 (3) | 0.6730 (4) | 0.6663 (4) | 0.032 (4) | |
N2 | 0.4441 (3) | 0.6560 (4) | 0.7347 (4) | 0.032 (4) | |
N3 | 0.2092 (3) | 0.6513 (4) | 0.6816 (5) | 0.031 (4) | |
C1 | 0.3109 (4) | 0.6515 (5) | 0.7367 (5) | 0.025 (4) | |
C2 | 0.2421 (4) | 0.6592 (5) | 0.6129 (5) | 0.028 (4) | |
C7 | 0.1426 (4) | 0.6475 (5) | 0.5516 (5) | 0.029 (4) | |
H7 | 0.052453 | 0.636705 | 0.557170 | 0.035* | |
C6 | 0.1740 (3) | 0.6514 (5) | 0.4827 (5) | 0.032 (4) | |
H6 | 0.105486 | 0.640807 | 0.442052 | 0.038* | |
C5 | 0.3091 (3) | 0.6713 (4) | 0.4731 (5) | 0.032 (4) | |
H5 | 0.330092 | 0.675794 | 0.426325 | 0.038* | |
C4 | 0.4101 (4) | 0.6841 (6) | 0.5330 (5) | 0.032 (4) | |
H4 | 0.499771 | 0.697537 | 0.526873 | 0.038* | |
C3 | 0.3790 (4) | 0.6771 (5) | 0.6023 (5) | 0.030 (4) | |
C14 | 0.6173 (2) | 0.6826 (4) | 0.6646 (4) | 0.025 (4) | |
C19 | 0.6680 (3) | 0.8598 (4) | 0.6325 (4) | 0.032 (5) | |
H19 | 0.610407 | 0.971326 | 0.611430 | 0.038* | |
C18 | 0.8045 (3) | 0.8720 (5) | 0.6317 (5) | 0.035 (6) | |
H18 | 0.839571 | 0.993269 | 0.610581 | 0.042* | |
C17 | 0.8883 (3) | 0.7078 (5) | 0.6617 (4) | 0.038 (5) | |
H17 | 0.980488 | 0.716673 | 0.660689 | 0.046* | |
C16 | 0.8376 (3) | 0.5281 (5) | 0.6935 (5) | 0.033 (5) | |
H16 | 0.895436 | 0.415210 | 0.713329 | 0.040* | |
C15 | 0.7007 (3) | 0.5152 (4) | 0.6959 (4) | 0.033 (5) | |
H15 | 0.665785 | 0.396088 | 0.718228 | 0.039* | |
C8 | 0.2786 (4) | 0.6527 (5) | 0.8111 (5) | 0.026 (4) | |
C9 | 0.1434 (3) | 0.6759 (5) | 0.8198 (5) | 0.030 (4) | |
H9 | 0.074086 | 0.680775 | 0.779456 | 0.036* | |
C10 | 0.1159 (4) | 0.6914 (5) | 0.8899 (4) | 0.031 (4) | |
H10 | 0.027105 | 0.715499 | 0.896116 | 0.037* | |
C11 | 0.2146 (3) | 0.6725 (4) | 0.9506 (5) | 0.035 (4) | |
H11 | 0.192095 | 0.678390 | 0.997075 | 0.042* | |
C12 | 0.3482 (4) | 0.6446 (5) | 0.9423 (5) | 0.033 (4) | |
H12 | 0.416358 | 0.629481 | 0.982931 | 0.039* | |
C13 | 0.3781 (4) | 0.6397 (5) | 0.8725 (5) | 0.030 (4) | |
H13 | 0.468026 | 0.627187 | 0.866690 | 0.036* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0164 (16) | 0.0254 (12) | 0.057 (12) | 0.0001 (11) | 0.016 (3) | −0.001 (3) |
N2 | 0.0184 (16) | 0.0249 (12) | 0.056 (12) | −0.0014 (10) | 0.016 (3) | −0.002 (3) |
N3 | 0.0169 (18) | 0.0198 (12) | 0.054 (12) | 0.0006 (11) | 0.001 (3) | −0.003 (3) |
C1 | 0.0144 (17) | 0.0143 (12) | 0.046 (12) | 0.0005 (12) | 0.008 (3) | −0.002 (3) |
C2 | 0.018 (2) | 0.0146 (13) | 0.052 (13) | 0.0019 (13) | 0.005 (4) | 0.000 (4) |
C7 | 0.0147 (18) | 0.0219 (14) | 0.049 (13) | 0.0020 (12) | 0.004 (3) | 0.001 (3) |
C6 | 0.023 (2) | 0.0222 (14) | 0.050 (13) | −0.0011 (13) | 0.005 (4) | −0.003 (4) |
C5 | 0.0248 (17) | 0.0224 (14) | 0.049 (13) | 0.0004 (11) | 0.009 (3) | 0.000 (3) |
C4 | 0.0202 (19) | 0.0236 (13) | 0.054 (12) | −0.0013 (13) | 0.012 (4) | −0.003 (4) |
C3 | 0.0181 (19) | 0.0152 (13) | 0.056 (12) | 0.0017 (13) | 0.007 (4) | 0.001 (4) |
C14 | 0.0142 (13) | 0.0266 (13) | 0.037 (13) | −0.0011 (10) | 0.008 (3) | 0.000 (2) |
C19 | 0.0215 (16) | 0.0313 (15) | 0.041 (17) | −0.0013 (11) | 0.003 (4) | 0.003 (2) |
C18 | 0.0231 (16) | 0.0474 (18) | 0.036 (19) | −0.0082 (12) | 0.011 (4) | 0.005 (3) |
C17 | 0.0152 (15) | 0.057 (2) | 0.043 (17) | 0.0011 (13) | 0.005 (4) | −0.001 (3) |
C16 | 0.0259 (16) | 0.0452 (18) | 0.027 (17) | 0.0151 (13) | −0.003 (4) | 0.001 (3) |
C15 | 0.0252 (15) | 0.0319 (16) | 0.041 (16) | 0.0035 (11) | 0.007 (3) | 0.000 (3) |
C8 | 0.0164 (19) | 0.0153 (12) | 0.050 (12) | −0.0016 (12) | 0.012 (4) | −0.004 (3) |
C9 | 0.0195 (19) | 0.0176 (13) | 0.054 (14) | −0.0012 (12) | 0.010 (4) | −0.003 (4) |
C10 | 0.0209 (18) | 0.0184 (14) | 0.057 (14) | −0.0026 (13) | 0.014 (4) | −0.004 (3) |
C11 | 0.0292 (18) | 0.0197 (13) | 0.058 (14) | −0.0027 (12) | 0.012 (4) | 0.002 (3) |
C12 | 0.028 (2) | 0.0212 (14) | 0.050 (13) | −0.0005 (13) | 0.008 (4) | −0.002 (4) |
C13 | 0.0184 (18) | 0.0197 (13) | 0.052 (13) | 0.0014 (13) | 0.009 (3) | −0.003 (3) |
N1—N2 | 1.361 (8) | C19—C18 | 1.374 (4) |
N1—C3 | 1.392 (8) | C18—H18 | 0.9300 |
N1—C14 | 1.438 (4) | C18—C17 | 1.357 (5) |
N2—C1 | 1.344 (4) | C17—H17 | 0.9300 |
N3—C1 | 1.313 (7) | C17—C16 | 1.377 (5) |
N3—C2 | 1.374 (8) | C16—H16 | 0.9300 |
C1—C8 | 1.473 (8) | C16—C15 | 1.385 (4) |
C2—C7 | 1.379 (8) | C15—H15 | 0.9300 |
C2—C3 | 1.425 (5) | C8—C9 | 1.401 (5) |
C7—H7 | 0.9300 | C8—C13 | 1.381 (8) |
C7—C6 | 1.372 (9) | C9—H9 | 0.9300 |
C6—H6 | 0.9300 | C9—C10 | 1.379 (8) |
C6—C5 | 1.402 (5) | C10—H10 | 0.9300 |
C5—H5 | 0.9300 | C10—C11 | 1.370 (8) |
C5—C4 | 1.370 (7) | C11—H11 | 0.9300 |
C4—H4 | 0.9300 | C11—C12 | 1.386 (5) |
C4—C3 | 1.376 (8) | C12—H12 | 0.9300 |
C14—C19 | 1.367 (5) | C12—C13 | 1.381 (9) |
C14—C15 | 1.377 (5) | C13—H13 | 0.9300 |
C19—H19 | 0.9300 | ||
N2—N1—C3 | 124.3 (4) | C18—C19—H19 | 120.2 |
N2—N1—C14 | 114.3 (6) | C19—C18—H18 | 119.9 |
C3—N1—C14 | 121.4 (6) | C17—C18—C19 | 120.2 (4) |
C1—N2—N1 | 114.5 (6) | C17—C18—H18 | 119.9 |
C1—N3—C2 | 116.3 (4) | C18—C17—H17 | 119.8 |
N2—C1—C8 | 114.1 (6) | C18—C17—C16 | 120.4 (3) |
N3—C1—N2 | 128.4 (7) | C16—C17—H17 | 119.8 |
N3—C1—C8 | 117.5 (4) | C17—C16—H16 | 120.0 |
N3—C2—C7 | 120.5 (4) | C17—C16—C15 | 120.1 (3) |
N3—C2—C3 | 121.6 (6) | C15—C16—H16 | 120.0 |
C7—C2—C3 | 117.9 (7) | C14—C15—C16 | 118.5 (4) |
C2—C7—H7 | 119.4 | C14—C15—H15 | 120.7 |
C6—C7—C2 | 121.2 (4) | C16—C15—H15 | 120.7 |
C6—C7—H7 | 119.4 | C9—C8—C1 | 119.0 (6) |
C7—C6—H6 | 119.9 | C13—C8—C1 | 121.9 (4) |
C7—C6—C5 | 120.2 (6) | C13—C8—C9 | 119.1 (7) |
C5—C6—H6 | 119.9 | C8—C9—H9 | 120.9 |
C6—C5—H5 | 120.1 | C10—C9—C8 | 118.2 (6) |
C4—C5—C6 | 119.8 (7) | C10—C9—H9 | 120.9 |
C4—C5—H5 | 120.1 | C9—C10—H10 | 118.8 |
C5—C4—H4 | 120.0 | C11—C10—C9 | 122.4 (4) |
C5—C4—C3 | 120.1 (4) | C11—C10—H10 | 118.8 |
C3—C4—H4 | 120.0 | C10—C11—H11 | 120.2 |
N1—C3—C2 | 114.8 (6) | C10—C11—C12 | 119.5 (7) |
C4—C3—N1 | 124.3 (4) | C12—C11—H11 | 120.2 |
C4—C3—C2 | 120.8 (6) | C11—C12—H12 | 120.7 |
C19—C14—N1 | 119.2 (3) | C13—C12—C11 | 118.6 (6) |
C19—C14—C15 | 121.2 (2) | C13—C12—H12 | 120.7 |
C15—C14—N1 | 119.6 (3) | C8—C13—H13 | 119.0 |
C14—C19—H19 | 120.2 | C12—C13—C8 | 122.0 (4) |
C14—C19—C18 | 119.6 (3) | C12—C13—H13 | 119.0 |
N1—N2—C1—N3 | 3.4 (5) | C7—C6—C5—C4 | 0.8 (5) |
N1—N2—C1—C8 | −174.9 (3) | C6—C5—C4—C3 | 0.1 (5) |
N1—C14—C19—C18 | 178.9 (6) | C5—C4—C3—N1 | 175.2 (2) |
N1—C14—C15—C16 | 180.0 (6) | C5—C4—C3—C2 | −0.8 (6) |
N2—N1—C3—C2 | −0.7 (5) | C3—N1—N2—C1 | −2.5 (5) |
N2—N1—C3—C4 | −176.9 (3) | C3—N1—C14—C19 | 58.8 (6) |
N2—N1—C14—C19 | −122.4 (6) | C3—N1—C14—C15 | −122.1 (6) |
N2—N1—C14—C15 | 56.8 (6) | C3—C2—C7—C6 | 0.4 (5) |
N2—C1—C8—C9 | 172.2 (2) | C14—N1—N2—C1 | 178.75 (19) |
N2—C1—C8—C13 | −5.5 (5) | C14—N1—C3—C2 | 178.1 (3) |
N3—C1—C8—C9 | −6.3 (4) | C14—N1—C3—C4 | 1.8 (6) |
N3—C1—C8—C13 | 176.1 (2) | C14—C19—C18—C17 | 0.9 (10) |
N3—C2—C7—C6 | −178.9 (3) | C19—C14—C15—C16 | −0.9 (10) |
N3—C2—C3—N1 | 3.4 (5) | C19—C18—C17—C16 | −0.4 (10) |
N3—C2—C3—C4 | 179.8 (4) | C18—C17—C16—C15 | −0.8 (10) |
C1—N3—C2—C7 | 176.4 (2) | C17—C16—C15—C14 | 1.4 (10) |
C1—N3—C2—C3 | −2.8 (5) | C15—C14—C19—C18 | −0.2 (10) |
C1—C8—C9—C10 | −175.8 (3) | C8—C9—C10—C11 | −3.7 (6) |
C1—C8—C13—C12 | 178.9 (3) | C9—C8—C13—C12 | 1.3 (5) |
C2—N3—C1—N2 | −0.8 (5) | C9—C10—C11—C12 | 2.3 (5) |
C2—N3—C1—C8 | 177.4 (3) | C10—C11—C12—C13 | 0.9 (5) |
C2—C7—C6—C5 | −1.1 (6) | C11—C12—C13—C8 | −2.7 (6) |
C7—C2—C3—N1 | −175.8 (3) | C13—C8—C9—C10 | 1.9 (5) |
C7—C2—C3—C4 | 0.5 (5) |
C19H14N3 | F(000) = 596 |
Mr = 284.33 | Dx = 1.718 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.0002 (5) Å | Cell parameters from 2189 reflections |
b = 6.0842 (3) Å | θ = 3.5–25.8° |
c = 18.352 (2) Å | µ = 0.10 mm−1 |
β = 100.026 (6)° | T = 276 K |
V = 1099.55 (15) Å3 | Block, clear dark brown |
Z = 4 | 0.16 × 0.14 × 0.09 mm |
Bruker SMART APEX2 area detector diffractometer | 734 independent reflections |
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs | 545 reflections with I > 2σ(I) |
Mirror optics monochromator | Rint = 0.032 |
Detector resolution: 7.9 pixels mm-1 | θmax = 26.3°, θmin = 2.2° |
ω and φ scans | h = −11→12 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0585 before and 0.0406 after correction. The Ratio of minimum to maximum transmission is 0.8887. The λ/2 correction factor is Not present. | k = −7→7 |
Tmin = 0.662, Tmax = 0.745 | l = −7→7 |
4978 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.086 | w = 1/[σ2(Fo2) + (0.0375P)2 + 0.580P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
734 reflections | Δρmax = 0.10 e Å−3 |
199 parameters | Δρmin = −0.11 e Å−3 |
231 restraints |
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. High pressure data collection in a diamond anvil cell. 5.5393 GPa. PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT432_ALERT_2_G Short Inter X···Y Contact N3 ..C8 3.02 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C1 ..C9 3.19 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C2 ..C10 3.16 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C2 ..C13 3.17 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 2.93 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 3.16 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C6 ..C11 3.20 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.04 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.05 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C15 ..C18 3.16 Ang. 3/2-x,-1/2+y,3/2-z = 2_646 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C15 ..C19 3.18 Ang. 3/2-x,-1/2+y,3/2-z = 2_646 Check Correct. H H contacts can be as short as 1.7 Ang. See Wood, Peter A., et al. "Analysis of the compression of molecular crystal structures using Hirshfeld surfaces." CrystEngComm 10.4 (2008): 368-376. PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 231 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 61 Note PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ···. 3 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ··· 3 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 15 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 15 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info No action taken. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.4764 (3) | 0.6682 (5) | 0.6709 (4) | 0.031 (4) | |
N2 | 0.4457 (3) | 0.6527 (4) | 0.7402 (4) | 0.032 (4) | |
N3 | 0.2097 (3) | 0.6447 (5) | 0.6863 (4) | 0.028 (4) | |
C1 | 0.3121 (3) | 0.6477 (5) | 0.7422 (5) | 0.024 (4) | |
C2 | 0.2436 (3) | 0.6532 (5) | 0.6169 (5) | 0.026 (4) | |
C7 | 0.1443 (3) | 0.6404 (5) | 0.5541 (5) | 0.026 (4) | |
H7 | 0.053804 | 0.626691 | 0.559300 | 0.031* | |
C6 | 0.1763 (3) | 0.6476 (6) | 0.4847 (5) | 0.029 (4) | |
H6 | 0.107954 | 0.636499 | 0.443467 | 0.035* | |
C5 | 0.3117 (3) | 0.6717 (4) | 0.4755 (5) | 0.031 (4) | |
H5 | 0.333197 | 0.678639 | 0.428240 | 0.037* | |
C4 | 0.4124 (4) | 0.6849 (6) | 0.5364 (5) | 0.031 (4) | |
H4 | 0.502336 | 0.701681 | 0.530563 | 0.037* | |
C3 | 0.3801 (3) | 0.6734 (6) | 0.6062 (5) | 0.030 (4) | |
C14 | 0.6191 (2) | 0.6869 (4) | 0.6685 (4) | 0.023 (4) | |
C19 | 0.6656 (3) | 0.8792 (5) | 0.6438 (4) | 0.024 (5) | |
H19 | 0.605321 | 0.993302 | 0.628581 | 0.029* | |
C18 | 0.8015 (3) | 0.9047 (5) | 0.6412 (5) | 0.035 (6) | |
H18 | 0.833242 | 1.035458 | 0.624246 | 0.042* | |
C17 | 0.8896 (3) | 0.7356 (5) | 0.6639 (4) | 0.032 (5) | |
H17 | 0.981733 | 0.752205 | 0.662873 | 0.038* | |
C16 | 0.8423 (3) | 0.5423 (5) | 0.6882 (4) | 0.026 (5) | |
H16 | 0.902543 | 0.427547 | 0.702695 | 0.031* | |
C15 | 0.7057 (3) | 0.5156 (5) | 0.6914 (4) | 0.033 (5) | |
H15 | 0.673685 | 0.385385 | 0.708504 | 0.039* | |
C8 | 0.2795 (3) | 0.6487 (5) | 0.8176 (5) | 0.025 (4) | |
C9 | 0.1447 (3) | 0.6759 (5) | 0.8266 (5) | 0.032 (4) | |
H9 | 0.075078 | 0.682922 | 0.785780 | 0.039* | |
C10 | 0.1174 (4) | 0.6921 (6) | 0.8977 (4) | 0.034 (4) | |
H10 | 0.028533 | 0.718222 | 0.904052 | 0.041* | |
C11 | 0.2162 (3) | 0.6710 (4) | 0.9591 (5) | 0.036 (4) | |
H11 | 0.194278 | 0.677592 | 1.006230 | 0.043* | |
C12 | 0.3499 (3) | 0.6398 (5) | 0.9497 (5) | 0.030 (4) | |
H12 | 0.418599 | 0.623347 | 0.990544 | 0.036* | |
C13 | 0.3792 (4) | 0.6334 (5) | 0.8792 (5) | 0.027 (4) | |
H13 | 0.469175 | 0.618191 | 0.873140 | 0.033* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0153 (15) | 0.0239 (13) | 0.055 (11) | −0.0002 (11) | 0.011 (3) | 0.003 (3) |
N2 | 0.0182 (16) | 0.0244 (13) | 0.056 (11) | −0.0024 (10) | 0.014 (3) | −0.001 (3) |
N3 | 0.0159 (16) | 0.0196 (12) | 0.048 (12) | 0.0014 (11) | 0.000 (3) | 0.001 (3) |
C1 | 0.0146 (17) | 0.0130 (13) | 0.044 (11) | 0.0026 (12) | 0.001 (3) | 0.003 (3) |
C2 | 0.0149 (18) | 0.0147 (14) | 0.048 (12) | −0.0007 (13) | 0.001 (3) | −0.001 (4) |
C7 | 0.0150 (17) | 0.0185 (14) | 0.045 (12) | −0.0007 (13) | 0.005 (3) | −0.005 (4) |
C6 | 0.0212 (18) | 0.0222 (15) | 0.043 (13) | 0.0010 (13) | 0.004 (4) | −0.002 (4) |
C5 | 0.0236 (16) | 0.0211 (14) | 0.047 (12) | 0.0001 (12) | 0.004 (3) | 0.002 (3) |
C4 | 0.0177 (18) | 0.0228 (14) | 0.052 (12) | −0.0015 (14) | 0.002 (4) | 0.002 (4) |
C3 | 0.0182 (18) | 0.0147 (14) | 0.055 (11) | −0.0002 (14) | 0.004 (3) | 0.003 (4) |
C14 | 0.0144 (13) | 0.0270 (14) | 0.029 (13) | −0.0019 (11) | 0.005 (3) | −0.003 (2) |
C19 | 0.0189 (14) | 0.0304 (16) | 0.021 (17) | −0.0002 (11) | −0.002 (3) | 0.004 (3) |
C18 | 0.0223 (15) | 0.0396 (18) | 0.044 (19) | −0.0029 (12) | 0.006 (4) | 0.011 (3) |
C17 | 0.0159 (14) | 0.0454 (19) | 0.034 (18) | 0.0000 (12) | 0.002 (3) | −0.003 (3) |
C16 | 0.0237 (15) | 0.0363 (18) | 0.016 (17) | 0.0117 (13) | −0.002 (3) | −0.003 (3) |
C15 | 0.0257 (15) | 0.0254 (16) | 0.047 (17) | −0.0001 (11) | 0.006 (3) | 0.000 (3) |
C8 | 0.0149 (18) | 0.0142 (13) | 0.045 (12) | −0.0015 (12) | 0.004 (4) | −0.002 (3) |
C9 | 0.0160 (18) | 0.0197 (15) | 0.061 (13) | −0.0025 (13) | 0.005 (3) | 0.002 (4) |
C10 | 0.0193 (17) | 0.0192 (14) | 0.066 (13) | −0.0026 (13) | 0.014 (3) | 0.002 (4) |
C11 | 0.0264 (17) | 0.0185 (14) | 0.065 (14) | −0.0022 (12) | 0.013 (3) | 0.001 (3) |
C12 | 0.0238 (19) | 0.0213 (15) | 0.045 (13) | 0.0020 (13) | 0.005 (4) | −0.004 (4) |
C13 | 0.0178 (17) | 0.0192 (14) | 0.045 (12) | 0.0027 (13) | 0.007 (3) | −0.002 (3) |
N1—N2 | 1.361 (8) | C19—C18 | 1.376 (4) |
N1—C3 | 1.393 (8) | C18—H18 | 0.9300 |
N1—C14 | 1.440 (4) | C18—C17 | 1.372 (5) |
N2—C1 | 1.343 (4) | C17—H17 | 0.9300 |
N3—C1 | 1.317 (7) | C17—C16 | 1.371 (5) |
N3—C2 | 1.375 (8) | C16—H16 | 0.9300 |
C1—C8 | 1.475 (8) | C16—C15 | 1.387 (4) |
C2—C7 | 1.386 (8) | C15—H15 | 0.9300 |
C2—C3 | 1.418 (5) | C8—C9 | 1.397 (5) |
C7—H7 | 0.9300 | C8—C13 | 1.375 (8) |
C7—C6 | 1.367 (9) | C9—H9 | 0.9300 |
C6—H6 | 0.9300 | C9—C10 | 1.383 (8) |
C6—C5 | 1.402 (5) | C10—H10 | 0.9300 |
C5—H5 | 0.9300 | C10—C11 | 1.369 (8) |
C5—C4 | 1.370 (7) | C11—H11 | 0.9300 |
C4—H4 | 0.9300 | C11—C12 | 1.390 (5) |
C4—C3 | 1.377 (8) | C12—H12 | 0.9300 |
C14—C19 | 1.365 (5) | C12—C13 | 1.375 (9) |
C14—C15 | 1.374 (4) | C13—H13 | 0.9300 |
C19—H19 | 0.9300 | ||
N2—N1—C3 | 124.2 (4) | C18—C19—H19 | 119.9 |
N2—N1—C14 | 114.8 (6) | C19—C18—H18 | 120.3 |
C3—N1—C14 | 120.9 (6) | C17—C18—C19 | 119.4 (3) |
C1—N2—N1 | 114.5 (6) | C17—C18—H18 | 120.3 |
C1—N3—C2 | 115.9 (4) | C18—C17—H17 | 119.9 |
N2—C1—C8 | 114.2 (6) | C16—C17—C18 | 120.2 (2) |
N3—C1—N2 | 128.4 (7) | C16—C17—H17 | 119.9 |
N3—C1—C8 | 117.5 (4) | C17—C16—H16 | 119.6 |
N3—C2—C7 | 120.8 (4) | C17—C16—C15 | 120.8 (3) |
N3—C2—C3 | 122.0 (6) | C15—C16—H16 | 119.6 |
C7—C2—C3 | 117.2 (7) | C14—C15—C16 | 118.2 (3) |
C2—C7—H7 | 119.2 | C14—C15—H15 | 120.9 |
C6—C7—C2 | 121.5 (4) | C16—C15—H15 | 120.9 |
C6—C7—H7 | 119.2 | C9—C8—C1 | 119.1 (6) |
C7—C6—H6 | 119.9 | C13—C8—C1 | 121.6 (4) |
C7—C6—C5 | 120.3 (6) | C13—C8—C9 | 119.2 (7) |
C5—C6—H6 | 119.9 | C8—C9—H9 | 120.9 |
C6—C5—H5 | 120.1 | C10—C9—C8 | 118.3 (6) |
C4—C5—C6 | 119.7 (7) | C10—C9—H9 | 120.9 |
C4—C5—H5 | 120.1 | C9—C10—H10 | 118.7 |
C5—C4—H4 | 120.1 | C11—C10—C9 | 122.5 (4) |
C5—C4—C3 | 119.9 (4) | C11—C10—H10 | 118.7 |
C3—C4—H4 | 120.1 | C10—C11—H11 | 120.6 |
N1—C3—C2 | 114.8 (6) | C10—C11—C12 | 118.9 (7) |
C4—C3—N1 | 123.7 (4) | C12—C11—H11 | 120.6 |
C4—C3—C2 | 121.4 (6) | C11—C12—H12 | 120.4 |
C19—C14—N1 | 118.4 (3) | C13—C12—C11 | 119.2 (6) |
C19—C14—C15 | 121.2 (2) | C13—C12—H12 | 120.4 |
C15—C14—N1 | 120.4 (3) | C8—C13—H13 | 119.0 |
C14—C19—H19 | 119.9 | C12—C13—C8 | 121.9 (4) |
C14—C19—C18 | 120.2 (3) | C12—C13—H13 | 119.0 |
N1—N2—C1—N3 | 3.7 (5) | C7—C6—C5—C4 | 0.9 (5) |
N1—N2—C1—C8 | −175.4 (3) | C6—C5—C4—C3 | 0.3 (5) |
N1—C14—C19—C18 | 179.4 (7) | C5—C4—C3—N1 | 174.8 (2) |
N1—C14—C15—C16 | −179.7 (7) | C5—C4—C3—C2 | −1.5 (6) |
N2—N1—C3—C2 | −2.2 (5) | C3—N1—N2—C1 | −1.5 (5) |
N2—N1—C3—C4 | −178.7 (4) | C3—N1—C14—C19 | 64.8 (7) |
N2—N1—C14—C19 | −113.2 (6) | C3—N1—C14—C15 | −115.9 (6) |
N2—N1—C14—C15 | 66.0 (7) | C3—C2—C7—C6 | −0.2 (5) |
N2—C1—C8—C9 | 170.8 (3) | C14—N1—N2—C1 | 176.5 (2) |
N2—C1—C8—C13 | −6.3 (5) | C14—N1—C3—C2 | 180.0 (3) |
N3—C1—C8—C9 | −8.4 (5) | C14—N1—C3—C4 | 3.4 (6) |
N3—C1—C8—C13 | 174.5 (2) | C14—C19—C18—C17 | −0.2 (11) |
N3—C2—C7—C6 | −179.7 (4) | C19—C14—C15—C16 | −0.5 (10) |
N3—C2—C3—N1 | 4.3 (5) | C19—C18—C17—C16 | 0.7 (11) |
N3—C2—C3—C4 | −179.0 (4) | C18—C17—C16—C15 | −1.1 (11) |
C1—N3—C2—C7 | 176.9 (2) | C17—C16—C15—C14 | 1.0 (10) |
C1—N3—C2—C3 | −2.6 (5) | C15—C14—C19—C18 | 0.1 (11) |
C1—C8—C9—C10 | −175.5 (4) | C8—C9—C10—C11 | −3.5 (6) |
C1—C8—C13—C12 | 178.4 (3) | C9—C8—C13—C12 | 1.3 (6) |
C2—N3—C1—N2 | −1.7 (5) | C9—C10—C11—C12 | 2.3 (6) |
C2—N3—C1—C8 | 177.4 (3) | C10—C11—C12—C13 | 0.7 (5) |
C2—C7—C6—C5 | −1.0 (6) | C11—C12—C13—C8 | −2.5 (6) |
C7—C2—C3—N1 | −175.2 (3) | C13—C8—C9—C10 | 1.7 (5) |
C7—C2—C3—C4 | 1.5 (6) |
C19H14N3 | F(000) = 596 |
Mr = 284.33 | Dx = 1.729 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.9832 (7) Å | Cell parameters from 2090 reflections |
b = 6.0752 (4) Å | θ = 3.5–25.8° |
c = 18.290 (3) Å | µ = 0.11 mm−1 |
β = 100.005 (9)° | T = 276 K |
V = 1092.4 (2) Å3 | Block, clear dark brown |
Z = 4 | 0.16 × 0.14 × 0.09 mm |
Bruker SMART APEX2 area detector diffractometer | 736 independent reflections |
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs | 535 reflections with I > 2σ(I) |
Mirror optics monochromator | Rint = 0.037 |
Detector resolution: 7.9 pixels mm-1 | θmax = 26.3°, θmin = 2.2° |
ω and φ scans | h = −11→12 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1389 before and 0.0678 after correction. The Ratio of minimum to maximum transmission is 0.9054. The λ/2 correction factor is Not present. | k = −7→7 |
Tmin = 0.675, Tmax = 0.745 | l = −7→7 |
5042 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.116 | w = 1/[σ2(Fo2) + (0.0737P)2 + 0.2439P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
736 reflections | Δρmax = 0.13 e Å−3 |
199 parameters | Δρmin = −0.15 e Å−3 |
231 restraints |
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. High pressure data collection in a diamond anvil cell. 5.7631 GPa. PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT432_ALERT_2_G Short Inter X···Y Contact N3 ..C8 3.01 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C2 ..C10 3.16 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C2 ..C13 3.17 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C2 ..C9 3.19 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 2.93 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 3.15 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C6 ..C11 3.18 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.03 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.05 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C15 ..C18 3.11 Ang. 3/2-x,-1/2+y,3/2-z = 2_646 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C15 ..C19 3.13 Ang. 3/2-x,-1/2+y,3/2-z = 2_646 Check Correct. H H contacts can be as short as 1.7 Ang. See Wood, Peter A., et al. "Analysis of the compression of molecular crystal structures using Hirshfeld surfaces." CrystEngComm 10.4 (2008): 368-376. PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 231 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 55 Note PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ···. 1 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 15 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 15 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info No action taken. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.4768 (4) | 0.6672 (5) | 0.6719 (5) | 0.040 (4) | |
N2 | 0.4460 (3) | 0.6539 (5) | 0.7411 (5) | 0.041 (4) | |
N3 | 0.2098 (4) | 0.6435 (5) | 0.6870 (5) | 0.038 (4) | |
C1 | 0.3127 (4) | 0.6474 (5) | 0.7427 (5) | 0.032 (4) | |
C2 | 0.2430 (4) | 0.6520 (6) | 0.6172 (5) | 0.037 (4) | |
C7 | 0.1440 (4) | 0.6398 (6) | 0.5546 (5) | 0.035 (5) | |
H7 | 0.053241 | 0.627084 | 0.559680 | 0.042* | |
C6 | 0.1768 (4) | 0.6462 (6) | 0.4851 (6) | 0.040 (4) | |
H6 | 0.108379 | 0.633530 | 0.443690 | 0.047* | |
C5 | 0.3115 (4) | 0.6715 (4) | 0.4754 (5) | 0.040 (4) | |
H5 | 0.332754 | 0.679270 | 0.427932 | 0.048* | |
C4 | 0.4125 (4) | 0.6847 (6) | 0.5367 (5) | 0.039 (4) | |
H4 | 0.502668 | 0.701223 | 0.530793 | 0.047* | |
C3 | 0.3803 (4) | 0.6736 (6) | 0.6070 (5) | 0.038 (4) | |
C14 | 0.6197 (3) | 0.6883 (5) | 0.6701 (5) | 0.032 (5) | |
C19 | 0.6655 (3) | 0.8844 (5) | 0.6463 (5) | 0.035 (6) | |
H19 | 0.604648 | 0.998757 | 0.632087 | 0.043* | |
C18 | 0.8014 (3) | 0.9119 (6) | 0.6434 (5) | 0.051 (7) | |
H18 | 0.832834 | 1.044851 | 0.627696 | 0.061* | |
C17 | 0.8901 (3) | 0.7413 (5) | 0.6640 (5) | 0.044 (6) | |
H17 | 0.982039 | 0.758666 | 0.662151 | 0.052* | |
C16 | 0.8436 (3) | 0.5447 (5) | 0.6872 (5) | 0.042 (6) | |
H16 | 0.904203 | 0.429409 | 0.700510 | 0.050* | |
C15 | 0.7074 (3) | 0.5168 (5) | 0.6910 (5) | 0.044 (6) | |
H15 | 0.675996 | 0.384653 | 0.707379 | 0.052* | |
C8 | 0.2791 (4) | 0.6481 (5) | 0.8185 (5) | 0.033 (4) | |
C9 | 0.1450 (4) | 0.6762 (6) | 0.8284 (5) | 0.037 (5) | |
H9 | 0.075015 | 0.684127 | 0.787609 | 0.045* | |
C10 | 0.1176 (4) | 0.6921 (6) | 0.8994 (5) | 0.039 (5) | |
H10 | 0.028634 | 0.718576 | 0.905829 | 0.047* | |
C11 | 0.2164 (4) | 0.6704 (5) | 0.9607 (5) | 0.039 (5) | |
H11 | 0.194379 | 0.677076 | 1.008055 | 0.047* | |
C12 | 0.3506 (4) | 0.6382 (6) | 0.9514 (6) | 0.037 (5) | |
H12 | 0.419409 | 0.620323 | 0.992314 | 0.045* | |
C13 | 0.3792 (4) | 0.6333 (6) | 0.8806 (5) | 0.034 (4) | |
H13 | 0.469279 | 0.619505 | 0.874386 | 0.041* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0185 (18) | 0.0239 (15) | 0.079 (13) | 0.0001 (13) | 0.017 (3) | −0.001 (3) |
N2 | 0.0194 (19) | 0.0248 (14) | 0.081 (13) | −0.0006 (12) | 0.016 (3) | −0.003 (3) |
N3 | 0.021 (2) | 0.0186 (14) | 0.074 (13) | 0.0005 (13) | 0.005 (4) | 0.002 (3) |
C1 | 0.015 (2) | 0.0125 (15) | 0.068 (13) | 0.0001 (14) | 0.008 (4) | 0.000 (4) |
C2 | 0.019 (2) | 0.0172 (16) | 0.076 (13) | 0.0010 (16) | 0.010 (4) | −0.002 (4) |
C7 | 0.0144 (19) | 0.0196 (16) | 0.073 (14) | 0.0029 (14) | 0.011 (4) | −0.003 (4) |
C6 | 0.024 (2) | 0.0211 (16) | 0.074 (14) | −0.0002 (15) | 0.012 (4) | −0.006 (4) |
C5 | 0.023 (2) | 0.0220 (16) | 0.073 (14) | 0.0002 (13) | 0.005 (4) | 0.000 (3) |
C4 | 0.020 (2) | 0.0229 (16) | 0.075 (13) | −0.0032 (15) | 0.009 (4) | −0.002 (4) |
C3 | 0.020 (2) | 0.0167 (16) | 0.078 (13) | 0.0016 (16) | 0.009 (4) | 0.004 (4) |
C14 | 0.0156 (16) | 0.0272 (16) | 0.055 (15) | −0.0008 (12) | 0.012 (3) | −0.005 (3) |
C19 | 0.0204 (18) | 0.0288 (19) | 0.06 (2) | −0.0011 (12) | 0.004 (4) | 0.002 (3) |
C18 | 0.0230 (18) | 0.036 (2) | 0.10 (2) | −0.0029 (14) | 0.014 (4) | 0.010 (3) |
C17 | 0.0181 (17) | 0.042 (2) | 0.07 (2) | −0.0003 (14) | 0.010 (4) | −0.006 (3) |
C16 | 0.0257 (17) | 0.034 (2) | 0.063 (19) | 0.0101 (14) | 0.004 (4) | −0.008 (3) |
C15 | 0.0228 (17) | 0.0248 (18) | 0.083 (19) | 0.0008 (12) | 0.008 (4) | 0.001 (3) |
C8 | 0.013 (2) | 0.0158 (15) | 0.071 (13) | 0.0001 (13) | 0.008 (4) | 0.003 (4) |
C9 | 0.021 (2) | 0.0183 (16) | 0.073 (15) | −0.0043 (14) | 0.008 (4) | 0.004 (4) |
C10 | 0.019 (2) | 0.0208 (16) | 0.080 (15) | −0.0005 (15) | 0.017 (4) | 0.006 (4) |
C11 | 0.029 (2) | 0.0191 (16) | 0.073 (16) | −0.0003 (13) | 0.022 (4) | 0.005 (3) |
C12 | 0.026 (2) | 0.0227 (17) | 0.064 (14) | 0.0025 (14) | 0.014 (4) | −0.003 (4) |
C13 | 0.020 (2) | 0.0179 (16) | 0.066 (14) | 0.0020 (15) | 0.013 (4) | −0.002 (4) |
N1—N2 | 1.356 (9) | C19—C18 | 1.377 (4) |
N1—C3 | 1.392 (8) | C18—H18 | 0.9300 |
N1—C14 | 1.438 (4) | C18—C17 | 1.372 (5) |
N2—C1 | 1.337 (5) | C17—H17 | 0.9300 |
N3—C1 | 1.316 (7) | C17—C16 | 1.375 (5) |
N3—C2 | 1.374 (8) | C16—H16 | 0.9300 |
C1—C8 | 1.481 (8) | C16—C15 | 1.384 (4) |
C2—C7 | 1.380 (8) | C15—H15 | 0.9300 |
C2—C3 | 1.420 (6) | C8—C9 | 1.392 (6) |
C7—H7 | 0.9300 | C8—C13 | 1.380 (8) |
C7—C6 | 1.367 (9) | C9—H9 | 0.9300 |
C6—H6 | 0.9300 | C9—C10 | 1.377 (9) |
C6—C5 | 1.396 (6) | C10—H10 | 0.9300 |
C5—H5 | 0.9300 | C10—C11 | 1.365 (8) |
C5—C4 | 1.373 (8) | C11—H11 | 0.9300 |
C4—H4 | 0.9300 | C11—C12 | 1.394 (5) |
C4—C3 | 1.381 (9) | C12—H12 | 0.9300 |
C14—C19 | 1.374 (5) | C12—C13 | 1.373 (9) |
C14—C15 | 1.372 (4) | C13—H13 | 0.9300 |
C19—H19 | 0.9300 | ||
N2—N1—C3 | 124.1 (4) | C18—C19—H19 | 119.9 |
N2—N1—C14 | 114.4 (6) | C19—C18—H18 | 120.3 |
C3—N1—C14 | 121.4 (7) | C17—C18—C19 | 119.4 (4) |
C1—N2—N1 | 114.2 (7) | C17—C18—H18 | 120.3 |
C1—N3—C2 | 115.9 (5) | C18—C17—H17 | 119.9 |
N2—C1—C8 | 114.1 (7) | C18—C17—C16 | 120.3 (3) |
N3—C1—N2 | 129.0 (8) | C16—C17—H17 | 119.9 |
N3—C1—C8 | 116.9 (5) | C17—C16—H16 | 119.7 |
N3—C2—C7 | 121.0 (4) | C17—C16—C15 | 120.6 (3) |
N3—C2—C3 | 121.3 (7) | C15—C16—H16 | 119.7 |
C7—C2—C3 | 117.7 (7) | C14—C15—C16 | 118.6 (4) |
C2—C7—H7 | 119.4 | C14—C15—H15 | 120.7 |
C6—C7—C2 | 121.2 (5) | C16—C15—H15 | 120.7 |
C6—C7—H7 | 119.4 | C9—C8—C1 | 120.0 (7) |
C7—C6—H6 | 119.6 | C13—C8—C1 | 121.4 (4) |
C7—C6—C5 | 120.8 (7) | C13—C8—C9 | 118.4 (7) |
C5—C6—H6 | 119.6 | C8—C9—H9 | 120.5 |
C6—C5—H5 | 120.3 | C10—C9—C8 | 119.0 (7) |
C4—C5—C6 | 119.4 (7) | C10—C9—H9 | 120.5 |
C4—C5—H5 | 120.3 | C9—C10—H10 | 118.8 |
C5—C4—H4 | 120.0 | C11—C10—C9 | 122.4 (4) |
C5—C4—C3 | 120.0 (4) | C11—C10—H10 | 118.8 |
C3—C4—H4 | 120.0 | C10—C11—H11 | 120.5 |
N1—C3—C2 | 115.2 (7) | C10—C11—C12 | 119.1 (7) |
C4—C3—N1 | 123.8 (5) | C12—C11—H11 | 120.5 |
C4—C3—C2 | 120.9 (7) | C11—C12—H12 | 120.7 |
C19—C14—N1 | 118.1 (3) | C13—C12—C11 | 118.7 (7) |
C15—C14—N1 | 120.9 (3) | C13—C12—H12 | 120.7 |
C15—C14—C19 | 121.0 (3) | C8—C13—H13 | 118.8 |
C14—C19—H19 | 119.9 | C12—C13—C8 | 122.4 (5) |
C14—C19—C18 | 120.1 (3) | C12—C13—H13 | 118.8 |
N1—N2—C1—N3 | 3.0 (5) | C7—C6—C5—C4 | 1.6 (5) |
N1—N2—C1—C8 | −176.1 (3) | C6—C5—C4—C3 | −0.2 (6) |
N1—C14—C19—C18 | −179.8 (8) | C5—C4—C3—N1 | 174.5 (3) |
N1—C14—C15—C16 | 179.1 (8) | C5—C4—C3—C2 | −1.0 (7) |
N2—N1—C3—C2 | −3.6 (6) | C3—N1—N2—C1 | −0.1 (6) |
N2—N1—C3—C4 | −179.3 (4) | C3—N1—C14—C19 | 64.9 (8) |
N2—N1—C14—C19 | −111.5 (7) | C3—N1—C14—C15 | −114.6 (7) |
N2—N1—C14—C15 | 69.0 (8) | C3—C2—C7—C6 | 0.6 (6) |
N2—C1—C8—C9 | 170.0 (3) | C14—N1—N2—C1 | 176.3 (2) |
N2—C1—C8—C13 | −6.4 (5) | C14—N1—C3—C2 | −179.7 (3) |
N3—C1—C8—C9 | −9.2 (5) | C14—N1—C3—C4 | 4.6 (6) |
N3—C1—C8—C13 | 174.4 (3) | C14—C19—C18—C17 | 0.5 (12) |
N3—C2—C7—C6 | −179.4 (4) | C19—C14—C15—C16 | −0.4 (12) |
N3—C2—C3—N1 | 5.0 (6) | C19—C18—C17—C16 | 0.0 (12) |
N3—C2—C3—C4 | −179.2 (4) | C18—C17—C16—C15 | −0.7 (12) |
C1—N3—C2—C7 | 177.3 (3) | C17—C16—C15—C14 | 0.9 (12) |
C1—N3—C2—C3 | −2.7 (6) | C15—C14—C19—C18 | −0.3 (12) |
C1—C8—C9—C10 | −175.4 (4) | C8—C9—C10—C11 | −3.3 (7) |
C1—C8—C13—C12 | 178.6 (3) | C9—C8—C13—C12 | 2.2 (6) |
C2—N3—C1—N2 | −1.6 (6) | C9—C10—C11—C12 | 2.1 (6) |
C2—N3—C1—C8 | 177.5 (3) | C10—C11—C12—C13 | 1.2 (5) |
C2—C7—C6—C5 | −1.8 (6) | C11—C12—C13—C8 | −3.3 (6) |
C7—C2—C3—N1 | −175.0 (3) | C13—C8—C9—C10 | 1.1 (6) |
C7—C2—C3—C4 | 0.8 (6) |
C19H14N3 | F(000) = 596 |
Mr = 284.33 | Dx = 1.739 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.9663 (7) Å | Cell parameters from 1909 reflections |
b = 6.0642 (4) Å | θ = 3.6–25.9° |
c = 18.252 (3) Å | µ = 0.11 mm−1 |
β = 100.025 (9)° | T = 273 K |
V = 1086.3 (2) Å3 | Block, clear dark brown |
Z = 4 | 0.16 × 0.14 × 0.09 mm |
Bruker SMART APEX2 area detector diffractometer | 727 independent reflections |
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs | 481 reflections with I > 2σ(I) |
Mirror optics monochromator | Rint = 0.057 |
Detector resolution: 7.9 pixels mm-1 | θmax = 26.4°, θmin = 3.6° |
ω and φ scans | h = −11→12 |
Absorption correction: multi-scan SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1695 before and 0.0802 after correction. The Ratio of minimum to maximum transmission is 0.7794. The λ/2 correction factor is Not present. | k = −7→7 |
Tmin = 0.581, Tmax = 0.745 | l = −7→8 |
5236 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.050 | H-atom parameters constrained |
wR(F2) = 0.140 | w = 1/[σ2(Fo2) + (0.1083P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
727 reflections | Δρmax = 0.16 e Å−3 |
199 parameters | Δρmin = −0.14 e Å−3 |
231 restraints |
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. High pressure data collection in a diamond anvil cell. 6.0711 GPa. PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 22 Note PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large 0.11 Report PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 54 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT199_ALERT_1_G Reported _cell_measurement_temperature ···.. (K) 273 Check PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ···.. (K) 273 Check PLAT432_ALERT_2_G Short Inter X···Y Contact N3 ..C8 3.01 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C2 ..C10 3.15 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C2 ..C13 3.16 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C2 ..C9 3.19 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 2.92 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C3 ..C10 3.15 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C6 ..C11 3.16 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.03 Ang. 1/2-x,1/2+y,3/2-z = 2_556 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C12 3.04 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C7 ..C11 3.19 Ang. 1/2-x,-1/2+y,3/2-z = 2_546 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C15 ..C18 3.11 Ang. 3/2-x,-1/2+y,3/2-z = 2_646 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C15 ..C19 3.12 Ang. 3/2-x,-1/2+y,3/2-z = 2_646 Check PLAT432_ALERT_2_G Short Inter X···Y Contact C16 ..C19 3.18 Ang. 3/2-x,-1/2+y,3/2-z = 2_646 Check Correct. H H contacts can be as short as 1.7 Ang. See Wood, Peter A., et al. "Analysis of the compression of molecular crystal structures using Hirshfeld surfaces." CrystEngComm 10.4 (2008): 368-376. PLAT860_ALERT_3_G Number of Least-Squares Restraints ············. 231 Note PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 3 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 72 Note PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ···. 3 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ··· 12 Note PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ 14 Units PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ 14 Units PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info No action taken. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.4773 (4) | 0.6675 (6) | 0.6728 (5) | 0.034 (5) | |
N2 | 0.4457 (3) | 0.6538 (5) | 0.7417 (5) | 0.036 (4) | |
N3 | 0.2093 (4) | 0.6430 (6) | 0.6877 (5) | 0.035 (5) | |
C1 | 0.3125 (5) | 0.6471 (6) | 0.7441 (6) | 0.032 (4) | |
C2 | 0.2440 (5) | 0.6521 (7) | 0.6182 (6) | 0.035 (5) | |
C7 | 0.1447 (5) | 0.6387 (6) | 0.5548 (6) | 0.033 (5) | |
H7 | 0.053919 | 0.624329 | 0.560047 | 0.040* | |
C6 | 0.1763 (4) | 0.6461 (7) | 0.4845 (6) | 0.040 (5) | |
H6 | 0.108403 | 0.634418 | 0.442755 | 0.047* | |
C5 | 0.3125 (4) | 0.6717 (5) | 0.4772 (6) | 0.034 (5) | |
H5 | 0.334595 | 0.680610 | 0.429833 | 0.041* | |
C4 | 0.4138 (5) | 0.6837 (7) | 0.5376 (6) | 0.034 (5) | |
H4 | 0.504045 | 0.698581 | 0.531440 | 0.041* | |
C3 | 0.3813 (4) | 0.6738 (7) | 0.6078 (6) | 0.032 (5) | |
C14 | 0.6200 (3) | 0.6885 (5) | 0.6695 (5) | 0.032 (5) | |
C19 | 0.6653 (3) | 0.8872 (6) | 0.6474 (5) | 0.033 (7) | |
H19 | 0.604207 | 1.002508 | 0.634468 | 0.040* | |
C18 | 0.8018 (3) | 0.9157 (6) | 0.6445 (6) | 0.037 (7) | |
H18 | 0.833477 | 1.050135 | 0.629798 | 0.044* | |
C17 | 0.8899 (3) | 0.7437 (6) | 0.6634 (5) | 0.026 (6) | |
H17 | 0.981369 | 0.760391 | 0.659964 | 0.031* | |
C16 | 0.8451 (3) | 0.5468 (6) | 0.6875 (5) | 0.033 (6) | |
H16 | 0.906872 | 0.433666 | 0.702341 | 0.040* | |
C15 | 0.7079 (3) | 0.5162 (5) | 0.6896 (5) | 0.037 (7) | |
H15 | 0.676244 | 0.381940 | 0.704339 | 0.045* | |
C8 | 0.2796 (4) | 0.6484 (6) | 0.8201 (5) | 0.033 (5) | |
C9 | 0.1446 (4) | 0.6749 (6) | 0.8285 (6) | 0.040 (5) | |
H9 | 0.074622 | 0.680410 | 0.787562 | 0.048* | |
C10 | 0.1183 (5) | 0.6926 (7) | 0.9001 (5) | 0.040 (6) | |
H10 | 0.029304 | 0.720682 | 0.906480 | 0.047* | |
C11 | 0.2166 (4) | 0.6711 (5) | 0.9623 (6) | 0.045 (6) | |
H11 | 0.194385 | 0.678202 | 1.009615 | 0.054* | |
C12 | 0.3506 (4) | 0.6382 (7) | 0.9527 (7) | 0.040 (5) | |
H12 | 0.419574 | 0.620678 | 0.993659 | 0.049* | |
C13 | 0.3797 (5) | 0.6319 (7) | 0.8816 (6) | 0.036 (5) | |
H13 | 0.469800 | 0.616092 | 0.875292 | 0.044* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0169 (19) | 0.0304 (17) | 0.055 (14) | 0.0003 (14) | 0.007 (3) | 0.000 (3) |
N2 | 0.021 (2) | 0.0313 (17) | 0.057 (14) | −0.0035 (13) | 0.010 (4) | −0.003 (4) |
N3 | 0.022 (2) | 0.0222 (16) | 0.060 (14) | −0.0006 (14) | 0.002 (4) | −0.001 (4) |
C1 | 0.019 (2) | 0.0172 (17) | 0.059 (14) | −0.0002 (16) | 0.006 (4) | −0.002 (4) |
C2 | 0.019 (2) | 0.0212 (18) | 0.063 (14) | 0.0004 (17) | 0.005 (4) | 0.002 (5) |
C7 | 0.019 (2) | 0.0224 (18) | 0.060 (15) | −0.0009 (17) | 0.010 (4) | −0.005 (4) |
C6 | 0.027 (3) | 0.029 (2) | 0.065 (15) | 0.0021 (17) | 0.015 (5) | 0.004 (5) |
C5 | 0.029 (2) | 0.0284 (19) | 0.045 (15) | −0.0030 (16) | 0.006 (4) | 0.000 (3) |
C4 | 0.023 (2) | 0.0291 (19) | 0.052 (14) | −0.0031 (17) | 0.009 (4) | −0.009 (4) |
C3 | 0.020 (2) | 0.0218 (18) | 0.054 (14) | 0.0016 (17) | 0.004 (4) | −0.004 (4) |
C14 | 0.0180 (18) | 0.0309 (19) | 0.046 (17) | −0.0030 (13) | 0.007 (4) | −0.006 (3) |
C19 | 0.026 (2) | 0.034 (2) | 0.04 (2) | 0.0015 (15) | 0.001 (5) | 0.010 (3) |
C18 | 0.024 (2) | 0.037 (2) | 0.05 (2) | −0.0032 (15) | 0.001 (4) | 0.006 (3) |
C17 | 0.0212 (19) | 0.047 (2) | 0.01 (2) | −0.0008 (15) | −0.002 (4) | −0.008 (3) |
C16 | 0.0273 (19) | 0.041 (2) | 0.03 (2) | 0.0130 (16) | 0.001 (4) | −0.003 (3) |
C15 | 0.027 (2) | 0.028 (2) | 0.06 (2) | −0.0010 (14) | 0.009 (4) | −0.003 (3) |
C8 | 0.017 (2) | 0.0207 (18) | 0.060 (14) | −0.0008 (16) | 0.005 (4) | −0.004 (4) |
C9 | 0.022 (3) | 0.0245 (19) | 0.077 (17) | −0.0032 (16) | 0.014 (4) | −0.006 (4) |
C10 | 0.024 (2) | 0.0205 (18) | 0.076 (18) | −0.0012 (17) | 0.015 (4) | −0.001 (4) |
C11 | 0.028 (2) | 0.0223 (18) | 0.083 (18) | −0.0003 (15) | 0.004 (5) | 0.000 (3) |
C12 | 0.031 (3) | 0.0258 (19) | 0.064 (15) | 0.0030 (17) | 0.009 (5) | −0.005 (5) |
C13 | 0.023 (2) | 0.0236 (18) | 0.062 (15) | 0.0024 (18) | 0.007 (4) | −0.005 (4) |
N1—N2 | 1.350 (9) | C19—C18 | 1.383 (5) |
N1—C3 | 1.389 (8) | C18—H18 | 0.9300 |
N1—C14 | 1.439 (5) | C18—C17 | 1.368 (5) |
N2—C1 | 1.336 (6) | C17—H17 | 0.9300 |
N3—C1 | 1.323 (8) | C17—C16 | 1.374 (6) |
N3—C2 | 1.374 (8) | C16—H16 | 0.9300 |
C1—C8 | 1.481 (8) | C16—C15 | 1.387 (5) |
C2—C7 | 1.388 (8) | C15—H15 | 0.9300 |
C2—C3 | 1.420 (7) | C8—C9 | 1.390 (6) |
C7—H7 | 0.9300 | C8—C13 | 1.370 (8) |
C7—C6 | 1.373 (9) | C9—H9 | 0.9300 |
C6—H6 | 0.9300 | C9—C10 | 1.381 (9) |
C6—C5 | 1.396 (6) | C10—H10 | 0.9300 |
C5—H5 | 0.9300 | C10—C11 | 1.370 (8) |
C5—C4 | 1.360 (8) | C11—H11 | 0.9300 |
C4—H4 | 0.9300 | C11—C12 | 1.391 (6) |
C4—C3 | 1.377 (9) | C12—H12 | 0.9300 |
C14—C19 | 1.372 (5) | C12—C13 | 1.377 (9) |
C14—C15 | 1.372 (5) | C13—H13 | 0.9300 |
C19—H19 | 0.9300 | ||
N2—N1—C3 | 124.0 (5) | C18—C19—H19 | 120.1 |
N2—N1—C14 | 115.9 (7) | C19—C18—H18 | 120.4 |
C3—N1—C14 | 120.0 (7) | C17—C18—C19 | 119.2 (4) |
C1—N2—N1 | 115.2 (7) | C17—C18—H18 | 120.4 |
C1—N3—C2 | 115.5 (5) | C18—C17—H17 | 119.5 |
N2—C1—C8 | 114.5 (7) | C18—C17—C16 | 120.9 (3) |
N3—C1—N2 | 128.2 (8) | C16—C17—H17 | 119.5 |
N3—C1—C8 | 117.3 (5) | C17—C16—H16 | 119.9 |
N3—C2—C7 | 120.6 (5) | C17—C16—C15 | 120.1 (4) |
N3—C2—C3 | 122.0 (7) | C15—C16—H16 | 119.9 |
C7—C2—C3 | 117.3 (7) | C14—C15—C16 | 118.5 (4) |
C2—C7—H7 | 119.0 | C14—C15—H15 | 120.7 |
C6—C7—C2 | 122.0 (5) | C16—C15—H15 | 120.7 |
C6—C7—H7 | 119.0 | C9—C8—C1 | 118.8 (7) |
C7—C6—H6 | 120.7 | C13—C8—C1 | 121.3 (5) |
C7—C6—C5 | 118.6 (8) | C13—C8—C9 | 119.9 (8) |
C5—C6—H6 | 120.7 | C8—C9—H9 | 121.3 |
C6—C5—H5 | 119.2 | C10—C9—C8 | 117.4 (7) |
C4—C5—C6 | 121.7 (8) | C10—C9—H9 | 121.3 |
C4—C5—H5 | 119.2 | C9—C10—H10 | 118.3 |
C5—C4—H4 | 120.3 | C11—C10—C9 | 123.4 (5) |
C5—C4—C3 | 119.4 (5) | C11—C10—H10 | 118.3 |
C3—C4—H4 | 120.3 | C10—C11—H11 | 120.9 |
N1—C3—C2 | 114.9 (7) | C10—C11—C12 | 118.3 (8) |
C4—C3—N1 | 123.9 (5) | C12—C11—H11 | 120.9 |
C4—C3—C2 | 121.1 (7) | C11—C12—H12 | 120.4 |
C19—C14—N1 | 117.9 (3) | C13—C12—C11 | 119.1 (8) |
C19—C14—C15 | 121.3 (3) | C13—C12—H12 | 120.4 |
C15—C14—N1 | 120.7 (4) | C8—C13—C12 | 121.8 (6) |
C14—C19—H19 | 120.1 | C8—C13—H13 | 119.1 |
C14—C19—C18 | 119.9 (3) | C12—C13—H13 | 119.1 |
N1—N2—C1—N3 | 3.1 (6) | C7—C6—C5—C4 | 1.6 (6) |
N1—N2—C1—C8 | −175.8 (4) | C6—C5—C4—C3 | −0.9 (6) |
N1—C14—C19—C18 | 179.0 (8) | C5—C4—C3—N1 | 174.8 (3) |
N1—C14—C15—C16 | −178.1 (8) | C5—C4—C3—C2 | −0.3 (7) |
N2—N1—C3—C2 | −3.4 (6) | C3—N1—N2—C1 | −0.2 (6) |
N2—N1—C3—C4 | −178.8 (4) | C3—N1—C14—C19 | 67.3 (8) |
N2—N1—C14—C19 | −109.4 (8) | C3—N1—C14—C15 | −114.4 (8) |
N2—N1—C14—C15 | 68.9 (9) | C3—C2—C7—C6 | −0.1 (7) |
N2—C1—C8—C9 | 170.5 (3) | C14—N1—N2—C1 | 176.4 (3) |
N2—C1—C8—C13 | −7.2 (6) | C14—N1—C3—C2 | −179.8 (3) |
N3—C1—C8—C9 | −8.4 (6) | C14—N1—C3—C4 | 4.8 (7) |
N3—C1—C8—C13 | 173.9 (3) | C14—C19—C18—C17 | 0.3 (13) |
N3—C2—C7—C6 | −179.6 (4) | C19—C14—C15—C16 | 0.2 (14) |
N3—C2—C3—N1 | 4.8 (6) | C19—C18—C17—C16 | −2.1 (13) |
N3—C2—C3—C4 | −179.7 (5) | C18—C17—C16—C15 | 3.0 (13) |
C1—N3—C2—C7 | 177.0 (3) | C17—C16—C15—C14 | −2.0 (13) |
C1—N3—C2—C3 | −2.5 (6) | C15—C14—C19—C18 | 0.7 (14) |
C1—C8—C9—C10 | −175.1 (4) | C8—C9—C10—C11 | −4.4 (7) |
C1—C8—C13—C12 | 178.5 (4) | C9—C8—C13—C12 | 0.8 (7) |
C2—N3—C1—N2 | −1.7 (6) | C9—C10—C11—C12 | 2.6 (6) |
C2—N3—C1—C8 | 177.1 (4) | C10—C11—C12—C13 | 1.0 (6) |
C2—C7—C6—C5 | −1.1 (7) | C11—C12—C13—C8 | −2.6 (7) |
C7—C2—C3—N1 | −174.8 (4) | C13—C8—C9—C10 | 2.6 (6) |
C7—C2—C3—C4 | 0.8 (6) |
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