Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800017864/cf6005sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536800017864/cf6005Isup2.hkl |
CCDC reference: 155853
All H atoms were included in the refinement, at calculated positions, as riding models with C—H set to 0.95 (Ar—H) and 0.99 Å (CH2), except for the amine H atom, which was located on difference syntheses and both positional and thermal parameters refined.
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.
C17H16N2 | Dx = 1.262 Mg m−3 |
Mr = 248.32 | Melting point: 330-331.5 K K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.1202 (3) Å | Cell parameters from 11683 reflections |
b = 9.9645 (3) Å | θ = 2.9–38.6° |
c = 13.8592 (5) Å | µ = 0.08 mm−1 |
β = 110.7743 (11)° | T = 150 K |
V = 1306.73 (7) Å3 | Plate, colourless |
Z = 4 | 0.30 × 0.15 × 0.08 mm |
F(000) = 528 |
Enraf Nonius KappaCCD area-detector diffractometer | 2989 independent reflections |
Radiation source: Enraf Nonius FR591 rotating anode | 2065 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.084 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
ϕ and ω scans | h = −13→13 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −12→12 |
Tmin = 0.978, Tmax = 0.994 | l = −17→18 |
18654 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0736P)2] where P = (Fo2 + 2Fc2)/3 |
2989 reflections | (Δ/σ)max < 0.001 |
176 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C17H16N2 | V = 1306.73 (7) Å3 |
Mr = 248.32 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.1202 (3) Å | µ = 0.08 mm−1 |
b = 9.9645 (3) Å | T = 150 K |
c = 13.8592 (5) Å | 0.30 × 0.15 × 0.08 mm |
β = 110.7743 (11)° |
Enraf Nonius KappaCCD area-detector diffractometer | 2989 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | 2065 reflections with I > 2σ(I) |
Tmin = 0.978, Tmax = 0.994 | Rint = 0.084 |
18654 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.126 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.17 e Å−3 |
2989 reflections | Δρmin = −0.24 e Å−3 |
176 parameters |
Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. |
Geometry. Mean plane data ex SHELXL97 ########################### Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 5.2752 (0.0044) x + 7.4657 (0.0035) y + 2.7323 (0.0067) z = 1.7749 (0.0007) * 0.0012 (0.0008) N1 * 0.0030 (0.0009) C2 * -0.0029 (0.0010) C3 * -0.0011 (0.0009) C4 * 0.0051 (0.0008) C10 * -0.0053 (0.0008) C9 0.0138 (0.0020) C5 - 0.0204 (0.0023) C6 - 0.0581 (0.0022) C7 - 0.0344 (0.0018) C8 Rms deviation of fitted atoms = 0.0035 - 3.4507 (0.0048) x + 2.9921 (0.0050) y + 13.2196 (0.0022) z = 4.8858 (0.0015) Angle to previous plane (with approximate e.s.d.) = 65.72 (0.04) * 0.0025 (0.0009) C14 * -0.0071 (0.0009) C15 * 0.0039 (0.0009) C16 * 0.0039 (0.0009) C17 * -0.0084 (0.0009) C18 * 0.0052 (0.0009) C19 Rms deviation of fitted atoms = 0.0055 |
x | y | z | Uiso*/Ueq | ||
N1 | 0.02455 (10) | 0.19291 (10) | 0.07554 (8) | 0.0333 (3) | |
C2 | −0.03832 (15) | 0.26763 (14) | −0.00655 (10) | 0.0402 (4) | |
H2 | −0.1150 | 0.3226 | −0.0065 | 0.050* | |
C3 | 0.00107 (15) | 0.27090 (15) | −0.09371 (11) | 0.0434 (4) | |
H3 | −0.0484 | 0.3262 | −0.1510 | 0.054* | |
C4 | 0.11133 (14) | 0.19373 (14) | −0.09507 (10) | 0.0395 (4) | |
H4 | 0.1396 | 0.1947 | −0.1535 | 0.049* | |
C5 | 0.29936 (15) | 0.02972 (13) | −0.00452 (11) | 0.0366 (3) | |
H5 | 0.3344 | 0.0291 | −0.0597 | 0.046* | |
C6 | 0.36030 (14) | −0.04891 (14) | 0.08017 (11) | 0.0388 (4) | |
H6 | 0.4378 | −0.1045 | 0.0830 | 0.048* | |
C7 | 0.31163 (13) | −0.04997 (13) | 0.16325 (11) | 0.0356 (3) | |
H7 | 0.3552 | −0.1074 | 0.2205 | 0.045* | |
C8 | 0.20115 (13) | 0.03150 (12) | 0.16259 (10) | 0.0298 (3) | |
C9 | 0.13443 (12) | 0.11497 (12) | 0.07400 (10) | 0.0287 (3) | |
C10 | 0.18326 (13) | 0.11239 (12) | −0.00945 (9) | 0.0313 (3) | |
N11 | 0.15190 (12) | 0.03852 (11) | 0.24255 (8) | 0.0351 (3) | |
H11 | 0.0637 (17) | 0.0787 (14) | 0.2254 (11) | 0.050 (4)* | |
C12 | 0.20238 (14) | −0.04938 (14) | 0.33069 (10) | 0.0362 (3) | |
H121 | 0.3063 | −0.0411 | 0.3630 | 0.045* | |
H122 | 0.1800 | −0.1435 | 0.3079 | 0.045* | |
C13 | 0.13455 (13) | −0.01480 (15) | 0.40963 (10) | 0.0379 (3) | |
H131 | 0.1855 | −0.0632 | 0.4746 | 0.047* | |
H132 | 0.1461 | 0.0825 | 0.4245 | 0.047* | |
C14 | −0.02005 (13) | −0.04922 (12) | 0.37568 (9) | 0.0297 (3) | |
C15 | −0.06201 (14) | −0.17757 (13) | 0.39305 (10) | 0.0339 (3) | |
H15 | 0.0076 | −0.2435 | 0.4250 | 0.042* | |
C16 | −0.20329 (14) | −0.20992 (13) | 0.36433 (10) | 0.0354 (3) | |
H16 | −0.2301 | −0.2973 | 0.3777 | 0.044* | |
C17 | −0.30593 (14) | −0.11632 (13) | 0.31635 (10) | 0.0349 (3) | |
H17 | −0.4031 | −0.1389 | 0.2967 | 0.044* | |
C18 | −0.26632 (14) | 0.01069 (13) | 0.29701 (10) | 0.0336 (3) | |
H18 | −0.3363 | 0.0752 | 0.2628 | 0.042* | |
C19 | −0.12446 (13) | 0.04375 (12) | 0.32759 (10) | 0.0319 (3) | |
H19 | −0.0982 | 0.1319 | 0.3153 | 0.040* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0295 (6) | 0.0370 (6) | 0.0349 (6) | 0.0009 (5) | 0.0132 (5) | −0.0003 (5) |
C2 | 0.0374 (7) | 0.0439 (8) | 0.0392 (8) | 0.0036 (6) | 0.0134 (6) | 0.0034 (7) |
C3 | 0.0487 (9) | 0.0460 (8) | 0.0344 (8) | −0.0007 (7) | 0.0132 (7) | 0.0068 (6) |
C4 | 0.0484 (8) | 0.0421 (8) | 0.0334 (8) | −0.0125 (7) | 0.0210 (7) | −0.0039 (6) |
C5 | 0.0383 (7) | 0.0393 (7) | 0.0413 (8) | −0.0096 (6) | 0.0253 (7) | −0.0109 (6) |
C6 | 0.0294 (7) | 0.0446 (8) | 0.0480 (9) | −0.0011 (6) | 0.0208 (6) | −0.0098 (6) |
C7 | 0.0296 (7) | 0.0416 (8) | 0.0372 (8) | 0.0015 (6) | 0.0136 (6) | −0.0018 (6) |
C8 | 0.0256 (6) | 0.0357 (7) | 0.0298 (7) | −0.0037 (5) | 0.0119 (5) | −0.0061 (5) |
C9 | 0.0255 (6) | 0.0310 (6) | 0.0314 (7) | −0.0065 (5) | 0.0125 (5) | −0.0057 (5) |
C10 | 0.0331 (7) | 0.0318 (7) | 0.0321 (7) | −0.0116 (5) | 0.0155 (6) | −0.0086 (5) |
N11 | 0.0330 (6) | 0.0458 (7) | 0.0308 (6) | 0.0095 (5) | 0.0163 (5) | 0.0049 (5) |
C12 | 0.0304 (7) | 0.0479 (8) | 0.0303 (7) | 0.0044 (6) | 0.0106 (6) | 0.0031 (6) |
C13 | 0.0319 (7) | 0.0560 (9) | 0.0250 (7) | −0.0022 (6) | 0.0090 (6) | −0.0007 (6) |
C14 | 0.0327 (7) | 0.0388 (7) | 0.0189 (6) | 0.0015 (6) | 0.0108 (5) | −0.0020 (5) |
C15 | 0.0413 (8) | 0.0333 (7) | 0.0266 (7) | 0.0068 (6) | 0.0114 (6) | 0.0026 (5) |
C16 | 0.0462 (8) | 0.0306 (7) | 0.0295 (7) | −0.0045 (6) | 0.0135 (6) | −0.0006 (5) |
C17 | 0.0332 (7) | 0.0420 (7) | 0.0299 (7) | −0.0032 (6) | 0.0118 (6) | −0.0030 (6) |
C18 | 0.0352 (7) | 0.0366 (7) | 0.0301 (7) | 0.0070 (6) | 0.0129 (6) | 0.0016 (6) |
C19 | 0.0399 (7) | 0.0299 (6) | 0.0283 (7) | 0.0000 (5) | 0.0152 (6) | 0.0013 (5) |
N1—C2 | 1.3192 (16) | N11—H11 | 0.929 (15) |
N1—C9 | 1.3626 (16) | C12—C13 | 1.5231 (18) |
C2—C3 | 1.400 (2) | C12—H121 | 0.9900 |
C2—H2 | 0.9500 | C12—H122 | 0.9900 |
C3—C4 | 1.361 (2) | C13—C14 | 1.5048 (17) |
C3—H3 | 0.9500 | C13—H131 | 0.9900 |
C4—C10 | 1.4079 (18) | C13—H132 | 0.9900 |
C4—H4 | 0.9500 | C14—C19 | 1.3854 (18) |
C5—C6 | 1.363 (2) | C14—C15 | 1.3952 (18) |
C5—C10 | 1.4166 (19) | C15—C16 | 1.3795 (19) |
C5—H5 | 0.9500 | C15—H15 | 0.9500 |
C6—C7 | 1.4038 (19) | C16—C17 | 1.3788 (18) |
C6—H6 | 0.9500 | C16—H16 | 0.9500 |
C7—C8 | 1.3791 (17) | C17—C18 | 1.3822 (18) |
C7—H7 | 0.9500 | C17—H17 | 0.9500 |
C8—N11 | 1.3686 (17) | C18—C19 | 1.3848 (18) |
C8—C9 | 1.4378 (18) | C18—H18 | 0.9500 |
C9—C10 | 1.4099 (17) | C19—H19 | 0.9500 |
N11—C12 | 1.4413 (16) | ||
C2—N1—C9 | 117.05 (12) | N11—C12—C13 | 110.90 (11) |
N1—C2—C3 | 124.01 (13) | N11—C12—H121 | 109.5 |
N1—C2—H2 | 118.0 | C13—C12—H121 | 109.5 |
C3—C2—H2 | 118.0 | N11—C12—H122 | 109.5 |
C4—C3—C2 | 118.98 (13) | C13—C12—H122 | 109.5 |
C4—C3—H3 | 120.5 | H121—C12—H122 | 108.0 |
C2—C3—H3 | 120.5 | C14—C13—C12 | 114.04 (11) |
C3—C4—C10 | 119.68 (13) | C14—C13—H131 | 108.7 |
C3—C4—H4 | 120.2 | C12—C13—H131 | 108.7 |
C10—C4—H4 | 120.2 | C14—C13—H132 | 108.7 |
C6—C5—C10 | 119.33 (12) | C12—C13—H132 | 108.7 |
C6—C5—H5 | 120.3 | H131—C13—H132 | 107.6 |
C10—C5—H5 | 120.3 | C19—C14—C15 | 117.97 (12) |
C5—C6—C7 | 121.83 (12) | C19—C14—C13 | 121.94 (12) |
C5—C6—H6 | 119.1 | C15—C14—C13 | 120.09 (12) |
C7—C6—H6 | 119.1 | C16—C15—C14 | 120.81 (12) |
C8—C7—C6 | 120.64 (13) | C16—C15—H15 | 119.6 |
C8—C7—H7 | 119.7 | C14—C15—H15 | 119.6 |
C6—C7—H7 | 119.7 | C17—C16—C15 | 120.50 (12) |
N11—C8—C7 | 123.50 (12) | C17—C16—H16 | 119.7 |
N11—C8—C9 | 117.79 (11) | C15—C16—H16 | 119.7 |
C7—C8—C9 | 118.70 (12) | C16—C17—C18 | 119.49 (12) |
N1—C9—C10 | 123.28 (11) | C16—C17—H17 | 120.3 |
N1—C9—C8 | 117.06 (11) | C18—C17—H17 | 120.3 |
C10—C9—C8 | 119.66 (11) | C17—C18—C19 | 119.93 (12) |
C4—C10—C9 | 117.00 (12) | C17—C18—H18 | 120.0 |
C4—C10—C5 | 123.19 (12) | C19—C18—H18 | 120.0 |
C9—C10—C5 | 119.81 (12) | C18—C19—C14 | 121.28 (12) |
C8—N11—C12 | 122.26 (11) | C18—C19—H19 | 119.4 |
C8—N11—H11 | 114.1 (10) | C14—C19—H19 | 119.4 |
C12—N11—H11 | 119.9 (10) | ||
C9—N1—C2—C3 | 0.08 (19) | C8—C9—C10—C5 | −1.26 (17) |
N1—C2—C3—C4 | −0.5 (2) | C6—C5—C10—C4 | −178.09 (12) |
C2—C3—C4—C10 | 0.1 (2) | C6—C5—C10—C9 | 1.56 (18) |
C10—C5—C6—C7 | −0.29 (19) | C7—C8—N11—C12 | −6.45 (19) |
C5—C6—C7—C8 | −1.3 (2) | C9—C8—N11—C12 | 174.23 (11) |
C6—C7—C8—N11 | −177.72 (12) | C8—N11—C12—C13 | 177.33 (11) |
C6—C7—C8—C9 | 1.58 (18) | N11—C12—C13—C14 | 70.24 (15) |
C2—N1—C9—C10 | 0.73 (17) | C12—C13—C14—C19 | −93.80 (15) |
C2—N1—C9—C8 | −178.79 (11) | C12—C13—C14—C15 | 86.71 (14) |
N11—C8—C9—N1 | −1.42 (16) | C19—C14—C15—C16 | −0.86 (18) |
C7—C8—C9—N1 | 179.23 (11) | C13—C14—C15—C16 | 178.66 (12) |
N11—C8—C9—C10 | 179.04 (11) | C14—C15—C16—C17 | 1.01 (19) |
C7—C8—C9—C10 | −0.31 (17) | C15—C16—C17—C18 | 0.05 (19) |
C3—C4—C10—C9 | 0.65 (18) | C16—C17—C18—C19 | −1.22 (19) |
C3—C4—C10—C5 | −179.69 (12) | C17—C18—C19—C14 | 1.38 (19) |
N1—C9—C10—C4 | −1.10 (17) | C15—C14—C19—C18 | −0.33 (19) |
C8—C9—C10—C4 | 178.41 (10) | C13—C14—C19—C18 | −179.84 (11) |
N1—C9—C10—C5 | 179.23 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···N1 | 0.929 (15) | 2.277 (15) | 2.6961 (15) | 106.8 (12) |
Experimental details
Crystal data | |
Chemical formula | C17H16N2 |
Mr | 248.32 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 150 |
a, b, c (Å) | 10.1202 (3), 9.9645 (3), 13.8592 (5) |
β (°) | 110.7743 (11) |
V (Å3) | 1306.73 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.30 × 0.15 × 0.08 |
Data collection | |
Diffractometer | Enraf Nonius KappaCCD area-detector diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1995) |
Tmin, Tmax | 0.978, 0.994 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18654, 2989, 2065 |
Rint | 0.084 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.126, 1.03 |
No. of reflections | 2989 |
No. of parameters | 176 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.17, −0.24 |
Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···N1 | 0.929 (15) | 2.277 (15) | 2.6961 (15) | 106.8 (12) |
NO COMMENT