Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616008950/sk3628sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229616008950/sk3628Isup2.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616008950/sk3628Isup3.cml |
CCDC reference: 1483369
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).
C17H18N2O | Z = 2 |
Mr = 266.33 | F(000) = 284 |
Triclinic, P1 | Dx = 1.288 Mg m−3 |
a = 5.6051 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.6411 (3) Å | Cell parameters from 3148 reflections |
c = 14.3853 (6) Å | θ = 2.8–27.5° |
α = 86.192 (2)° | µ = 0.08 mm−1 |
β = 81.237 (3)° | T = 120 K |
γ = 87.313 (2)° | Block, colourless |
V = 686.61 (4) Å3 | 0.21 × 0.16 × 0.15 mm |
Bruker D8 Venture diffractometer | 3144 independent reflections |
Radiation source: high brilliance microfocus sealed tube | 2352 reflections with I > 2σ(I) |
Multilayer monochromator | Rint = 0.081 |
φ and ω scans | θmax = 27.5°, θmin = 3.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −7→7 |
Tmin = 0.843, Tmax = 0.988 | k = −11→11 |
19423 measured reflections | l = −18→18 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.065 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.177 | w = 1/[σ2(Fo2) + (0.0889P)2 + 0.4781P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3144 reflections | Δρmax = 0.37 e Å−3 |
191 parameters | Δρmin = −0.32 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 1.0174 (4) | 0.0074 (2) | 0.19653 (15) | 0.0229 (4) | |
H1 | 1.0714 | 0.0103 | 0.1306 | 0.028* | |
C2 | 1.1527 (4) | −0.0790 (2) | 0.25633 (15) | 0.0241 (4) | |
H2 | 1.2967 | −0.1340 | 0.2316 | 0.029* | |
C3 | 1.0741 (4) | −0.0836 (2) | 0.35252 (15) | 0.0260 (5) | |
H3 | 1.1626 | −0.1439 | 0.3942 | 0.031* | |
C4 | 0.8674 (4) | −0.0007 (2) | 0.38798 (14) | 0.0242 (4) | |
H4 | 0.8172 | −0.0037 | 0.4542 | 0.029* | |
C4A | 0.7291 (4) | 0.0882 (2) | 0.32841 (14) | 0.0210 (4) | |
N5 | 0.5221 (3) | 0.16428 (19) | 0.37210 (13) | 0.0227 (4) | |
H5 | 0.528 (4) | 0.181 (3) | 0.4302 (19) | 0.027* | |
C6 | 0.3736 (4) | 0.2837 (2) | 0.32858 (14) | 0.0205 (4) | |
H6 | 0.2725 | 0.2331 | 0.2886 | 0.025* | |
C6A | 0.5271 (3) | 0.4043 (2) | 0.26745 (14) | 0.0206 (4) | |
C7 | 0.5428 (4) | 0.5549 (2) | 0.29484 (15) | 0.0235 (4) | |
H7 | 0.4431 | 0.5884 | 0.3498 | 0.028* | |
C8 | 0.7034 (4) | 0.6562 (2) | 0.24215 (16) | 0.0267 (5) | |
H8 | 0.7122 | 0.7590 | 0.2607 | 0.032* | |
C9 | 0.8504 (4) | 0.6069 (2) | 0.16267 (16) | 0.0275 (5) | |
H9 | 0.9618 | 0.6757 | 0.1271 | 0.033* | |
C10 | 0.8361 (4) | 0.4573 (2) | 0.13449 (14) | 0.0240 (4) | |
H10 | 0.9382 | 0.4243 | 0.0799 | 0.029* | |
C10A | 0.6720 (4) | 0.3548 (2) | 0.18609 (14) | 0.0208 (4) | |
C11 | 0.6618 (4) | 0.1865 (2) | 0.16240 (14) | 0.0212 (4) | |
H11 | 0.4895 | 0.1572 | 0.1797 | 0.025* | |
C11A | 0.8053 (4) | 0.0899 (2) | 0.22988 (14) | 0.0201 (4) | |
C61 | 0.2072 (4) | 0.3597 (2) | 0.40885 (14) | 0.0230 (4) | |
O61 | 0.2624 (3) | 0.35691 (18) | 0.48850 (10) | 0.0292 (4) | |
N61 | 0.0084 (3) | 0.4307 (2) | 0.38410 (14) | 0.0289 (4) | |
H61A | −0.086 (5) | 0.496 (3) | 0.423 (2) | 0.035* | |
H61B | −0.022 (5) | 0.428 (3) | 0.322 (2) | 0.035* | |
C111 | 0.7337 (4) | 0.1573 (2) | 0.05796 (14) | 0.0248 (4) | |
H111 | 0.8993 | 0.1931 | 0.0365 | 0.030* | |
H112 | 0.7349 | 0.0444 | 0.0498 | 0.030* | |
C112 | 0.5612 (4) | 0.2409 (3) | −0.00267 (15) | 0.0309 (5) | |
H121 | 0.5733 | 0.3534 | −0.0004 | 0.046* | |
H122 | 0.3953 | 0.2116 | 0.0214 | 0.046* | |
H123 | 0.6041 | 0.2116 | −0.0679 | 0.046* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0260 (10) | 0.0173 (9) | 0.0238 (10) | −0.0051 (8) | 0.0020 (8) | 0.0005 (7) |
C2 | 0.0226 (10) | 0.0169 (9) | 0.0316 (11) | −0.0017 (7) | −0.0001 (8) | −0.0017 (8) |
C3 | 0.0303 (11) | 0.0177 (9) | 0.0304 (11) | −0.0008 (8) | −0.0081 (9) | 0.0037 (8) |
C4 | 0.0303 (11) | 0.0192 (10) | 0.0219 (10) | −0.0035 (8) | −0.0004 (8) | 0.0023 (8) |
C4A | 0.0238 (10) | 0.0132 (9) | 0.0251 (10) | −0.0053 (7) | −0.0008 (8) | 0.0018 (7) |
N5 | 0.0268 (9) | 0.0186 (8) | 0.0209 (9) | −0.0013 (7) | 0.0005 (7) | 0.0030 (7) |
C6 | 0.0220 (10) | 0.0159 (9) | 0.0223 (10) | −0.0028 (7) | 0.0002 (8) | 0.0023 (7) |
C6A | 0.0197 (10) | 0.0178 (9) | 0.0240 (10) | −0.0025 (7) | −0.0037 (8) | 0.0037 (7) |
C7 | 0.0259 (11) | 0.0169 (9) | 0.0276 (10) | −0.0021 (8) | −0.0034 (8) | −0.0004 (8) |
C8 | 0.0286 (11) | 0.0161 (9) | 0.0361 (12) | −0.0035 (8) | −0.0084 (9) | 0.0040 (8) |
C9 | 0.0303 (12) | 0.0187 (10) | 0.0322 (11) | −0.0092 (8) | −0.0027 (9) | 0.0087 (8) |
C10 | 0.0270 (11) | 0.0203 (10) | 0.0224 (10) | −0.0036 (8) | 0.0015 (8) | 0.0049 (8) |
C10A | 0.0232 (10) | 0.0161 (9) | 0.0232 (10) | −0.0029 (7) | −0.0051 (8) | 0.0042 (7) |
C11 | 0.0224 (10) | 0.0182 (9) | 0.0219 (10) | −0.0028 (7) | −0.0002 (8) | 0.0014 (7) |
C11A | 0.0242 (10) | 0.0130 (9) | 0.0224 (10) | −0.0062 (7) | −0.0011 (8) | 0.0030 (7) |
C61 | 0.0242 (10) | 0.0167 (9) | 0.0264 (10) | −0.0048 (8) | 0.0014 (8) | 0.0016 (7) |
O61 | 0.0348 (9) | 0.0292 (8) | 0.0217 (8) | 0.0044 (6) | −0.0005 (6) | −0.0004 (6) |
N61 | 0.0267 (10) | 0.0337 (10) | 0.0260 (10) | 0.0046 (8) | −0.0020 (8) | −0.0065 (8) |
C111 | 0.0277 (11) | 0.0228 (10) | 0.0227 (10) | −0.0027 (8) | 0.0003 (8) | 0.0003 (8) |
C112 | 0.0351 (12) | 0.0328 (12) | 0.0242 (11) | −0.0013 (9) | −0.0030 (9) | 0.0005 (9) |
C1—C2 | 1.390 (3) | C8—C9 | 1.383 (3) |
C1—C11A | 1.394 (3) | C8—H8 | 0.9500 |
C1—H1 | 0.9500 | C9—C10 | 1.390 (3) |
C2—C3 | 1.385 (3) | C9—H9 | 0.9500 |
C2—H2 | 0.9500 | C10—C10A | 1.401 (3) |
C3—C4 | 1.380 (3) | C10—H10 | 0.9500 |
C3—H3 | 0.9500 | C10A—C11 | 1.521 (3) |
C4—C4A | 1.409 (3) | C11—C111 | 1.530 (3) |
C4—H4 | 0.9500 | C11—C11A | 1.534 (3) |
C4A—N5 | 1.391 (3) | C11—H11 | 1.0000 |
C4A—C11A | 1.416 (3) | C61—O61 | 1.230 (3) |
N5—C6 | 1.463 (3) | C61—N61 | 1.332 (3) |
N5—H5 | 0.86 (3) | N61—H61A | 0.92 (3) |
C6—C6A | 1.527 (3) | N61—H61B | 0.93 (3) |
C6—C61 | 1.533 (3) | C111—C112 | 1.525 (3) |
C6—H6 | 1.0000 | C111—H111 | 0.9900 |
C6A—C7 | 1.395 (3) | C111—H112 | 0.9900 |
C6A—C10A | 1.399 (3) | C112—H121 | 0.9800 |
C7—C8 | 1.389 (3) | C112—H122 | 0.9800 |
C7—H7 | 0.9500 | C112—H123 | 0.9800 |
C2—C1—C11A | 122.37 (19) | C10—C9—H9 | 119.8 |
C2—C1—H1 | 118.8 | C9—C10—C10A | 120.38 (19) |
C11A—C1—H1 | 118.8 | C9—C10—H10 | 119.8 |
C3—C2—C1 | 118.89 (19) | C10A—C10—H10 | 119.8 |
C3—C2—H2 | 120.6 | C6A—C10A—C10 | 118.96 (18) |
C1—C2—H2 | 120.6 | C6A—C10A—C11 | 118.37 (17) |
C4—C3—C2 | 120.19 (19) | C10—C10A—C11 | 122.41 (18) |
C4—C3—H3 | 119.9 | C10A—C11—C111 | 114.70 (16) |
C2—C3—H3 | 119.9 | C10A—C11—C11A | 106.41 (16) |
C3—C4—C4A | 121.63 (19) | C111—C11—C11A | 115.37 (17) |
C3—C4—H4 | 119.2 | C10A—C11—H11 | 106.6 |
C4A—C4—H4 | 119.2 | C111—C11—H11 | 106.6 |
N5—C4A—C4 | 116.43 (18) | C11A—C11—H11 | 106.6 |
N5—C4A—C11A | 125.18 (18) | C1—C11A—C4A | 118.54 (18) |
C4—C4A—C11A | 118.35 (18) | C1—C11A—C11 | 121.27 (18) |
C4A—N5—C6 | 126.66 (17) | C4A—C11A—C11 | 120.14 (17) |
C4A—N5—H5 | 113.1 (17) | O61—C61—N61 | 124.2 (2) |
C6—N5—H5 | 111.7 (17) | O61—C61—C6 | 120.92 (18) |
N5—C6—C6A | 112.01 (16) | N61—C61—C6 | 114.81 (18) |
N5—C6—C61 | 106.97 (16) | C61—N61—H61A | 121.2 (17) |
C6A—C6—C61 | 110.88 (16) | C61—N61—H61B | 119.5 (17) |
N5—C6—H6 | 109.0 | H61A—N61—H61B | 119 (2) |
C6A—C6—H6 | 109.0 | C112—C111—C11 | 111.97 (17) |
C61—C6—H6 | 109.0 | C112—C111—H111 | 109.2 |
C7—C6A—C10A | 120.08 (18) | C11—C111—H111 | 109.2 |
C7—C6A—C6 | 122.16 (18) | C112—C111—H112 | 109.2 |
C10A—C6A—C6 | 117.49 (17) | C11—C111—H112 | 109.2 |
C8—C7—C6A | 120.4 (2) | H111—C111—H112 | 107.9 |
C8—C7—H7 | 119.8 | C111—C112—H121 | 109.5 |
C6A—C7—H7 | 119.8 | C111—C112—H122 | 109.5 |
C9—C8—C7 | 119.81 (19) | H121—C112—H122 | 109.5 |
C9—C8—H8 | 120.1 | C111—C112—H123 | 109.5 |
C7—C8—H8 | 120.1 | H121—C112—H123 | 109.5 |
C8—C9—C10 | 120.39 (19) | H122—C112—H123 | 109.5 |
C8—C9—H9 | 119.8 | ||
C11A—C1—C2—C3 | 0.1 (3) | C9—C10—C10A—C6A | −1.5 (3) |
C1—C2—C3—C4 | −1.4 (3) | C9—C10—C10A—C11 | −175.49 (19) |
C2—C3—C4—C4A | 1.0 (3) | C6A—C10A—C11—C111 | 155.46 (18) |
C3—C4—C4A—N5 | 178.80 (18) | C10—C10A—C11—C111 | −30.5 (3) |
C3—C4—C4A—C11A | 0.7 (3) | C6A—C10A—C11—C11A | −75.7 (2) |
C4—C4A—N5—C6 | 168.43 (18) | C10—C10A—C11—C11A | 98.4 (2) |
C11A—C4A—N5—C6 | −13.6 (3) | C2—C1—C11A—C4A | 1.6 (3) |
C4A—N5—C6—C6A | −44.4 (3) | C2—C1—C11A—C11 | 178.97 (17) |
C4A—N5—C6—C61 | −166.12 (18) | N5—C4A—C11A—C1 | −179.84 (18) |
N5—C6—C6A—C7 | −107.6 (2) | C4—C4A—C11A—C1 | −1.9 (3) |
C61—C6—C6A—C7 | 11.8 (3) | N5—C4A—C11A—C11 | 2.7 (3) |
N5—C6—C6A—C10A | 66.4 (2) | C4—C4A—C11A—C11 | −179.35 (17) |
C61—C6—C6A—C10A | −174.19 (17) | C10A—C11—C11A—C1 | −115.44 (19) |
C10A—C6A—C7—C8 | −0.5 (3) | C111—C11—C11A—C1 | 13.0 (3) |
C6—C6A—C7—C8 | 173.28 (18) | C10A—C11—C11A—C4A | 61.9 (2) |
C6A—C7—C8—C9 | −0.7 (3) | C111—C11—C11A—C4A | −169.61 (17) |
C7—C8—C9—C10 | 0.9 (3) | N5—C6—C61—O61 | 24.0 (2) |
C8—C9—C10—C10A | 0.2 (3) | C6A—C6—C61—O61 | −98.4 (2) |
C7—C6A—C10A—C10 | 1.6 (3) | N5—C6—C61—N61 | −158.00 (17) |
C6—C6A—C10A—C10 | −172.48 (18) | C6A—C6—C61—N61 | 79.6 (2) |
C7—C6A—C10A—C11 | 175.88 (18) | C10A—C11—C111—C112 | −63.5 (2) |
C6—C6A—C10A—C11 | 1.8 (3) | C11A—C11—C111—C112 | 172.27 (17) |
Cg1 and Cg2 represent the centroids of the C1–C4/C4A/C11A and C6A/C7–C10/C10A rings, respectively |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5···O61 | 0.86 (3) | 2.19 (3) | 2.663 (2) | 114 (2) |
N61—H61A···O61i | 0.92 (3) | 1.98 (3) | 2.893 (2) | 175 (2) |
N61—H61B···Cg2ii | 0.93 (3) | 2.45 (3) | 3.254 (2) | 144 (2) |
C6—H6···Cg1ii | 1.00 | 2.77 | 3.622 (2) | 143 |
C8—H8···Cg1iii | 0.95 | 2.62 | 3.501 (2) | 154 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1, y, z; (iii) x, y+1, z. |