


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019012751/su5507sup1.cif |
![]() | Chemdraw file https://doi.org/10.1107/S2056989019012751/su5507Isup3.cdx |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2056989019012751/su5507Isup4.hkl |
![]() | Portable Document Format (PDF) file https://doi.org/10.1107/S2056989019012751/su5507sup5.pdf |
CCDC reference: 1953481
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.035
- wR factor = 0.094
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT242_ALERT_2_C Low 'MainMol' Ueq as Compared to Neighbors of C16 Check PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage 68 %
Alert level G PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 1 Report PLAT013_ALERT_1_G N.O.K. _shelx_hkl_checksum Found in CIF ...... Please Check PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT371_ALERT_2_G Long C(sp2)-C(sp1) Bond C6 - C8 . 1.43 Ang. PLAT371_ALERT_2_G Long C(sp2)-C(sp1) Bond C9 - C10 . 1.43 Ang. PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 5 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 4 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 7 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing
Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/1 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae, et al., 2008); software used to prepare material for publication: SHELXL2018/1 (Sheldrick, 2015b), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
C19H19N3 | Dx = 1.162 Mg m−3 |
Mr = 289.37 | Cu Kα radiation, λ = 1.54178 Å |
Orthorhombic, Pca21 | Cell parameters from 9967 reflections |
a = 9.3492 (2) Å | θ = 2.7–72.4° |
b = 16.3716 (3) Å | µ = 0.54 mm−1 |
c = 10.8030 (2) Å | T = 298 K |
V = 1653.52 (6) Å3 | Plate, colourless |
Z = 4 | 0.28 × 0.18 × 0.07 mm |
F(000) = 616 |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 2789 independent reflections |
Radiation source: INCOATEC IµS micro-focus source | 2610 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.034 |
ω scans | θmax = 72.4°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −11→10 |
Tmin = 0.86, Tmax = 0.96 | k = −18→20 |
12219 measured reflections | l = −11→13 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.094 | w = 1/[σ2(Fo2) + (0.0557P)2 + 0.0961P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
2789 reflections | Δρmax = 0.12 e Å−3 |
204 parameters | Δρmin = −0.11 e Å−3 |
1 restraint | Extinction correction: (SHELXL-2018/1; Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0082 (9) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. H-atoms attached to carbon were placed in calculated positions (C—H = 0.93 - 0.96 Å) while that attached to nitrogen was placed in a location derived from a difference map and its parameters adjusted to give N—H = 0.89 Å. All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. Refined as a 2-component inversion twin. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.20226 (17) | 0.18945 (10) | 0.67968 (18) | 0.0554 (4) | |
N2 | 0.02701 (15) | 0.12386 (9) | 0.57937 (16) | 0.0468 (4) | |
N3 | 0.04415 (16) | 0.17555 (10) | 0.37051 (16) | 0.0502 (4) | |
H3A | 0.116767 | 0.178516 | 0.317433 | 0.060* | |
C1 | −0.0790 (2) | 0.06627 (13) | 0.5650 (3) | 0.0660 (6) | |
H1 | −0.121888 | 0.057890 | 0.488345 | 0.079* | |
C2 | −0.1189 (3) | 0.02246 (16) | 0.6643 (4) | 0.0865 (9) | |
H2 | −0.188532 | −0.017726 | 0.655677 | 0.104* | |
C3 | −0.0571 (3) | 0.03642 (18) | 0.7815 (3) | 0.0880 (9) | |
H3 | −0.089464 | 0.007113 | 0.849685 | 0.106* | |
C4 | 0.0493 (3) | 0.09212 (17) | 0.7959 (3) | 0.0750 (7) | |
H4 | 0.090129 | 0.101102 | 0.873222 | 0.090* | |
C5 | 0.0964 (2) | 0.13603 (12) | 0.6914 (2) | 0.0516 (4) | |
C6 | 0.19772 (17) | 0.21348 (11) | 0.55737 (18) | 0.0451 (4) | |
C7 | 0.08982 (17) | 0.17490 (10) | 0.49231 (18) | 0.0428 (4) | |
C8 | 0.29559 (19) | 0.27114 (12) | 0.5063 (2) | 0.0519 (4) | |
C9 | 0.3769 (2) | 0.31813 (12) | 0.4592 (2) | 0.0544 (5) | |
C10 | 0.47560 (19) | 0.37266 (12) | 0.4002 (2) | 0.0523 (5) | |
C11 | 0.4920 (3) | 0.37126 (14) | 0.2731 (3) | 0.0645 (6) | |
H11 | 0.437975 | 0.335322 | 0.225549 | 0.077* | |
C12 | 0.5885 (3) | 0.42310 (16) | 0.2164 (3) | 0.0807 (8) | |
H12 | 0.599034 | 0.421939 | 0.130835 | 0.097* | |
C13 | 0.6684 (3) | 0.47609 (16) | 0.2855 (4) | 0.0835 (9) | |
H13 | 0.733481 | 0.510687 | 0.246809 | 0.100* | |
C14 | 0.6530 (3) | 0.47829 (15) | 0.4107 (4) | 0.0828 (8) | |
H14 | 0.707257 | 0.514665 | 0.457238 | 0.099* | |
C15 | 0.5569 (2) | 0.42660 (13) | 0.4694 (3) | 0.0660 (6) | |
H15 | 0.547037 | 0.428209 | 0.555024 | 0.079* | |
C16 | −0.0652 (2) | 0.23805 (15) | 0.3328 (2) | 0.0611 (5) | |
C17 | −0.1897 (3) | 0.2367 (2) | 0.4234 (3) | 0.0999 (11) | |
H17A | −0.154972 | 0.247021 | 0.505559 | 0.150* | |
H17B | −0.235099 | 0.184099 | 0.420959 | 0.150* | |
H17C | −0.257708 | 0.278058 | 0.400960 | 0.150* | |
C18 | −0.1144 (4) | 0.2142 (3) | 0.2049 (3) | 0.1049 (11) | |
H18A | −0.160262 | 0.161741 | 0.208243 | 0.157* | |
H18B | −0.033439 | 0.211409 | 0.150395 | 0.157* | |
H18C | −0.180883 | 0.254133 | 0.174553 | 0.157* | |
C19 | 0.0016 (3) | 0.32261 (16) | 0.3294 (3) | 0.0822 (8) | |
H19A | 0.032518 | 0.337470 | 0.411127 | 0.123* | |
H19B | −0.067847 | 0.361435 | 0.300697 | 0.123* | |
H19C | 0.082190 | 0.322349 | 0.274433 | 0.123* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0528 (9) | 0.0651 (10) | 0.0483 (9) | −0.0013 (7) | −0.0038 (7) | 0.0078 (8) |
N2 | 0.0442 (7) | 0.0412 (7) | 0.0549 (10) | −0.0007 (6) | 0.0074 (6) | 0.0037 (7) |
N3 | 0.0454 (8) | 0.0635 (9) | 0.0418 (9) | −0.0071 (7) | 0.0053 (6) | −0.0064 (7) |
C1 | 0.0603 (11) | 0.0552 (11) | 0.0826 (18) | −0.0148 (9) | 0.0118 (11) | −0.0021 (11) |
C2 | 0.0792 (16) | 0.0627 (14) | 0.118 (3) | −0.0184 (12) | 0.0232 (16) | 0.0196 (16) |
C3 | 0.0804 (16) | 0.0857 (18) | 0.098 (2) | 0.0008 (13) | 0.0196 (16) | 0.0453 (17) |
C4 | 0.0718 (14) | 0.0842 (16) | 0.0690 (17) | 0.0079 (12) | 0.0108 (12) | 0.0342 (13) |
C5 | 0.0512 (9) | 0.0544 (10) | 0.0493 (11) | 0.0076 (8) | 0.0024 (8) | 0.0110 (9) |
C6 | 0.0438 (8) | 0.0480 (8) | 0.0435 (10) | −0.0012 (7) | −0.0002 (7) | 0.0028 (8) |
C7 | 0.0409 (8) | 0.0443 (8) | 0.0433 (10) | −0.0013 (7) | 0.0053 (7) | 0.0016 (7) |
C8 | 0.0472 (9) | 0.0575 (10) | 0.0509 (11) | −0.0078 (8) | −0.0058 (8) | 0.0028 (9) |
C9 | 0.0471 (9) | 0.0565 (10) | 0.0596 (12) | −0.0067 (8) | −0.0050 (9) | 0.0053 (9) |
C10 | 0.0427 (9) | 0.0475 (9) | 0.0668 (14) | −0.0015 (7) | −0.0020 (8) | 0.0078 (9) |
C11 | 0.0659 (12) | 0.0624 (12) | 0.0653 (15) | −0.0104 (10) | −0.0010 (11) | 0.0067 (11) |
C12 | 0.0838 (16) | 0.0754 (15) | 0.083 (2) | −0.0081 (14) | 0.0188 (14) | 0.0157 (14) |
C13 | 0.0701 (14) | 0.0645 (14) | 0.116 (3) | −0.0156 (11) | 0.0163 (15) | 0.0214 (15) |
C14 | 0.0692 (15) | 0.0616 (13) | 0.118 (3) | −0.0214 (11) | −0.0035 (16) | 0.0017 (15) |
C15 | 0.0618 (12) | 0.0595 (11) | 0.0767 (16) | −0.0109 (10) | −0.0044 (11) | 0.0020 (12) |
C16 | 0.0461 (9) | 0.0900 (14) | 0.0471 (11) | −0.0011 (10) | −0.0041 (8) | 0.0094 (11) |
C17 | 0.0589 (13) | 0.153 (3) | 0.088 (2) | 0.0322 (16) | 0.0195 (12) | 0.039 (2) |
C18 | 0.0932 (19) | 0.163 (3) | 0.0583 (16) | −0.032 (2) | −0.0257 (15) | 0.013 (2) |
C19 | 0.0817 (15) | 0.0769 (15) | 0.088 (2) | 0.0111 (13) | −0.0097 (15) | 0.0147 (16) |
N1—C5 | 1.327 (3) | C11—C12 | 1.381 (3) |
N1—C6 | 1.379 (3) | C11—H11 | 0.9300 |
N2—C1 | 1.377 (2) | C12—C13 | 1.367 (4) |
N2—C5 | 1.388 (3) | C12—H12 | 0.9300 |
N2—C7 | 1.388 (2) | C13—C14 | 1.361 (5) |
N3—C7 | 1.383 (3) | C13—H13 | 0.9300 |
N3—C16 | 1.503 (3) | C14—C15 | 1.388 (3) |
N3—H3A | 0.8900 | C14—H14 | 0.9300 |
C1—C2 | 1.344 (4) | C15—H15 | 0.9300 |
C1—H1 | 0.9300 | C16—C18 | 1.508 (4) |
C2—C3 | 1.410 (5) | C16—C19 | 1.519 (4) |
C2—H2 | 0.9300 | C16—C17 | 1.522 (3) |
C3—C4 | 1.358 (4) | C17—H17A | 0.9600 |
C3—H3 | 0.9300 | C17—H17B | 0.9600 |
C4—C5 | 1.409 (3) | C17—H17C | 0.9600 |
C4—H4 | 0.9300 | C18—H18A | 0.9600 |
C6—C7 | 1.382 (2) | C18—H18B | 0.9600 |
C6—C8 | 1.426 (2) | C18—H18C | 0.9600 |
C8—C9 | 1.195 (3) | C19—H19A | 0.9600 |
C9—C10 | 1.434 (3) | C19—H19B | 0.9600 |
C10—C11 | 1.382 (3) | C19—H19C | 0.9600 |
C10—C15 | 1.384 (3) | ||
C5—N1—C6 | 104.87 (17) | C13—C12—C11 | 120.4 (3) |
C1—N2—C5 | 122.23 (19) | C13—C12—H12 | 119.8 |
C1—N2—C7 | 129.8 (2) | C11—C12—H12 | 119.8 |
C5—N2—C7 | 107.87 (15) | C14—C13—C12 | 120.1 (2) |
C7—N3—C16 | 118.26 (16) | C14—C13—H13 | 120.0 |
C7—N3—H3A | 112.2 | C12—C13—H13 | 120.0 |
C16—N3—H3A | 107.9 | C13—C14—C15 | 120.4 (3) |
C2—C1—N2 | 118.4 (3) | C13—C14—H14 | 119.8 |
C2—C1—H1 | 120.8 | C15—C14—H14 | 119.8 |
N2—C1—H1 | 120.8 | C10—C15—C14 | 119.8 (3) |
C1—C2—C3 | 121.1 (2) | C10—C15—H15 | 120.1 |
C1—C2—H2 | 119.5 | C14—C15—H15 | 120.1 |
C3—C2—H2 | 119.5 | N3—C16—C18 | 106.2 (2) |
C4—C3—C2 | 120.8 (2) | N3—C16—C19 | 110.32 (16) |
C4—C3—H3 | 119.6 | C18—C16—C19 | 109.9 (2) |
C2—C3—H3 | 119.6 | N3—C16—C17 | 109.6 (2) |
C3—C4—C5 | 118.6 (3) | C18—C16—C17 | 110.6 (2) |
C3—C4—H4 | 120.7 | C19—C16—C17 | 110.1 (3) |
C5—C4—H4 | 120.7 | C16—C17—H17A | 109.5 |
N1—C5—N2 | 111.09 (18) | C16—C17—H17B | 109.5 |
N1—C5—C4 | 130.3 (2) | H17A—C17—H17B | 109.5 |
N2—C5—C4 | 118.65 (19) | C16—C17—H17C | 109.5 |
N1—C6—C7 | 112.28 (16) | H17A—C17—H17C | 109.5 |
N1—C6—C8 | 122.66 (17) | H17B—C17—H17C | 109.5 |
C7—C6—C8 | 125.06 (17) | C16—C18—H18A | 109.5 |
C6—C7—N3 | 134.86 (17) | C16—C18—H18B | 109.5 |
C6—C7—N2 | 103.85 (16) | H18A—C18—H18B | 109.5 |
N3—C7—N2 | 121.22 (16) | C16—C18—H18C | 109.5 |
C9—C8—C6 | 177.5 (2) | H18A—C18—H18C | 109.5 |
C8—C9—C10 | 178.3 (2) | H18B—C18—H18C | 109.5 |
C11—C10—C15 | 119.1 (2) | C16—C19—H19A | 109.5 |
C11—C10—C9 | 120.2 (2) | C16—C19—H19B | 109.5 |
C15—C10—C9 | 120.7 (2) | H19A—C19—H19B | 109.5 |
C12—C11—C10 | 120.2 (3) | C16—C19—H19C | 109.5 |
C12—C11—H11 | 119.9 | H19A—C19—H19C | 109.5 |
C10—C11—H11 | 119.9 | H19B—C19—H19C | 109.5 |
C5—N2—C1—C2 | 2.1 (3) | C8—C6—C7—N2 | 178.52 (17) |
C7—N2—C1—C2 | 178.0 (2) | C16—N3—C7—C6 | −89.0 (2) |
N2—C1—C2—C3 | 1.8 (4) | C16—N3—C7—N2 | 94.6 (2) |
C1—C2—C3—C4 | −2.9 (5) | C1—N2—C7—C6 | −174.58 (19) |
C2—C3—C4—C5 | 0.2 (4) | C5—N2—C7—C6 | 1.78 (19) |
C6—N1—C5—N2 | 1.5 (2) | C1—N2—C7—N3 | 2.8 (3) |
C6—N1—C5—C4 | −179.3 (2) | C5—N2—C7—N3 | 179.13 (16) |
C1—N2—C5—N1 | 174.53 (18) | C15—C10—C11—C12 | 0.1 (4) |
C7—N2—C5—N1 | −2.2 (2) | C9—C10—C11—C12 | −179.2 (2) |
C1—N2—C5—C4 | −4.8 (3) | C10—C11—C12—C13 | 0.0 (4) |
C7—N2—C5—C4 | 178.52 (18) | C11—C12—C13—C14 | −0.3 (4) |
C3—C4—C5—N1 | −175.7 (2) | C12—C13—C14—C15 | 0.4 (4) |
C3—C4—C5—N2 | 3.5 (3) | C11—C10—C15—C14 | 0.1 (3) |
C5—N1—C6—C7 | −0.4 (2) | C9—C10—C15—C14 | 179.3 (2) |
C5—N1—C6—C8 | −179.81 (17) | C13—C14—C15—C10 | −0.3 (4) |
N1—C6—C7—N3 | −177.7 (2) | C7—N3—C16—C18 | −169.4 (2) |
C8—C6—C7—N3 | 1.7 (3) | C7—N3—C16—C19 | 71.5 (2) |
N1—C6—C7—N2 | −0.9 (2) | C7—N3—C16—C17 | −49.8 (3) |
Cg3 and Cg4 are the centroids of the C10–C15 and N1/N2/C1–C7 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···N1i | 0.89 | 2.26 | 3.150 (2) | 178 |
C2—H2···Cg4ii | 0.93 | 2.98 | 3.890 (3) | 167 |
C17—H17C···Cg3iii | 0.96 | 2.95 | 3.896 (3) | 170 |
Symmetry codes: (i) −x+1/2, y, z−1/2; (ii) x−1/2, −y, z; (iii) x−1, y, z. |