Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0021889812044147/db5105sup1.cif | |
Rietveld powder data file (CIF format) https://doi.org/10.1107/S0021889812044147/db5105sup2.rtv | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0021889812044147/db5105sup3.pdf |
CCDC reference: 914668
Data collection: Bruker XRD Commander 2.6 (Bruker, 2007); cell refinement: TOPAS 4.2 (Coelho, 2003; Bruker, 2009); data reduction: TOPAS 4.2 (Coelho, 2003; Bruker, 2009); program(s) used to solve structure: FOX 1.9.7.0 (Favre-Nicolin, Cerny, 2002); program(s) used to refine structure: TOPAS 4.2 (Coelho, 2003; Bruker, 2009); molecular graphics: OLEX2 1.2 (Dolomanov, 2009); software used to prepare material for publication: PLATON (Spek, 2003).
C25H30N4O3 | F(000) = 928 |
Mr = 434.53 | Dx = 1.244 Mg m−3 |
Orthorhombic, P212121 | Cu Kα1 radiation, λ = 1.54056 Å |
Hall symbol: P 2ac 2ab | µ = 0.67 mm−1 |
a = 35.9422 (5) Å | T = 298 K |
b = 12.91819 (12) Å | Particle morphology: round |
c = 4.99532 (3) Å | white |
V = 2319.37 (4) Å3 | flat_sheet, 15 × 15 mm |
Z = 4 |
Bruker D8 Advance Vario diffractometer | Data collection mode: transmission |
Radiation source: sealed X-ray tube | Scan method: continuous |
Ge 111 monochromator | 2θmin = 6.503°, 2θmax = 99.995°, 2θstep = 0.011° |
Specimen mounting: deposied on sticky tape |
Refinement on Inet | Profile function: pseudo-Voigt |
Least-squares matrix: full with fixed elements per cycle | 197 parameters |
Rp = 0.024 | 139 restraints |
Rwp = 0.035 | H-atom parameters constrained |
Rexp = 0.009 | 1/Yi |
RBragg = 0.013 | Background function: 12th order Chebyshev polynomial |
8923 data points | Preferred orientation correction: hkl dependent symmetrized spherical harmonics series (Jarvinen, 1993). The coefficients used were: y00 1 y20 0.662(8) y22p -0.742(6) y40 0.415(9) y42p -0.028(5) y44p 0.248(4) |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles |
x | y | z | Uiso*/Ueq | ||
O14 | 0.3867 (2) | 0.3686 (4) | 0.3911 (12) | 0.0380 (19)* | |
O18 | 0.4342 (2) | 0.1536 (4) | −0.3080 (13) | 0.0380 (19)* | |
O23 | 0.51609 (18) | −0.0385 (4) | 0.2462 (12) | 0.0380 (19)* | |
N13 | 0.3984 (2) | 0.2831 (5) | −0.0025 (8) | 0.028 (2)* | |
N17 | 0.45853 (19) | 0.0624 (4) | 0.0217 (9) | 0.028 (2)* | |
N22 | 0.5433 (2) | −0.0847 (5) | −0.1381 (12) | 0.028 (2)* | |
N27 | 0.44546 (19) | −0.3208 (4) | 0.1978 (12) | 0.028 (2)* | |
C1 | 0.23521 (12) | 0.7751 (4) | 0.1091 (11) | 0.0627 (16)* | |
C2 | 0.24949 (12) | 0.8457 (5) | 0.2883 (14) | 0.0627 (16)* | |
C3 | 0.19754 (13) | 0.7817 (5) | 0.0384 (13) | 0.0627 (16)* | |
C4 | 0.22679 (13) | 0.9206 (4) | 0.3960 (13) | 0.0627 (16)* | |
C5 | 0.17444 (16) | 0.8516 (5) | 0.1617 (13) | 0.0627 (16)* | |
C6 | 0.18769 (12) | 0.9131 (5) | 0.3560 (13) | 0.0627 (16)* | |
C7 | 0.26074 (18) | 0.7049 (5) | −0.0405 (12) | 0.0627 (16)* | |
C8 | 0.2816 (2) | 0.6299 (5) | 0.1400 (9) | 0.0627 (16)* | |
C9 | 0.31144 (19) | 0.5718 (5) | −0.0140 (11) | 0.0627 (16)* | |
C10 | 0.3324 (2) | 0.4943 (5) | 0.1531 (11) | 0.0627 (16)* | |
C11 | 0.3594 (2) | 0.4368 (4) | −0.0057 (10) | 0.0627 (16)* | |
C12 | 0.37949 (19) | 0.3572 (4) | 0.1489 (8) | 0.0627 (16)* | |
C15 | 0.4211 (3) | 0.2054 (5) | 0.1339 (11) | 0.0627 (16)* | |
C16 | 0.43996 (18) | 0.1412 (4) | −0.0687 (7) | 0.0627 (16)* | |
C19 | 0.48213 (14) | −0.0020 (4) | −0.1440 (10) | 0.0627 (16)* | |
C20 | 0.45903 (19) | −0.0961 (5) | −0.2532 (10) | 0.0627 (16)* | |
C21 | 0.51738 (12) | −0.0333 (4) | 0.0081 (8) | 0.0627 (16)* | |
C24 | 0.44612 (14) | −0.1749 (4) | −0.0442 (11) | 0.0627 (16)* | |
C25 | 0.46544 (17) | −0.2604 (5) | 0.0219 (15) | 0.0627 (16)* | |
C26 | 0.41363 (14) | −0.1760 (3) | 0.1220 (10) | 0.0627 (16)* | |
C28 | 0.41603 (13) | −0.2668 (3) | 0.2831 (11) | 0.0627 (16)* | |
C29 | 0.3857 (2) | −0.1023 (4) | 0.1869 (13) | 0.0627 (16)* | |
C30 | 0.3901 (2) | −0.2896 (4) | 0.4766 (12) | 0.0627 (16)* | |
C31 | 0.35753 (18) | −0.1306 (4) | 0.3582 (13) | 0.0627 (16)* | |
C32 | 0.36097 (19) | −0.2138 (5) | 0.5193 (13) | 0.0627 (16)* | |
H2 | 0.27474 | 0.84684 | 0.32876 | 0.075 (2)* | |
H3 | 0.18700 | 0.73211 | −0.07317 | 0.075 (2)* | |
H4 | 0.23593 | 0.96537 | 0.52607 | 0.075 (2)* | |
H5 | 0.14906 | 0.84881 | 0.12627 | 0.075 (2)* | |
H6 | 0.17248 | 0.96527 | 0.42292 | 0.075 (2)* | |
H7A | 0.24583 | 0.66482 | −0.16469 | 0.075 (2)* | |
H7B | 0.27810 | 0.74766 | −0.13983 | 0.075 (2)* | |
H8A | 0.29360 | 0.66831 | 0.28283 | 0.075 (2)* | |
H8B | 0.26348 | 0.58268 | 0.21605 | 0.075 (2)* | |
H9A | 0.29991 | 0.53608 | −0.16332 | 0.075 (2)* | |
H9B | 0.32933 | 0.62163 | −0.08143 | 0.075 (2)* | |
H10A | 0.34504 | 0.53259 | 0.29315 | 0.075 (2)* | |
H10B | 0.31619 | 0.44291 | 0.23332 | 0.075 (2)* | |
H11A | 0.34598 | 0.40607 | −0.15426 | 0.075 (2)* | |
H11B | 0.37775 | 0.48513 | −0.07403 | 0.075 (2)* | |
H13 | 0.39241 | 0.27262 | −0.16708 | 0.075 (2)* | |
H15A | 0.40490 | 0.16298 | 0.24422 | 0.075 (2)* | |
H15B | 0.43990 | 0.23743 | 0.24554 | 0.075 (2)* | |
H17 | 0.45730 | 0.04936 | 0.19031 | 0.075 (2)* | |
H19 | 0.48958 | 0.04107 | −0.29628 | 0.075 (2)* | |
H20A | 0.43670 | −0.06967 | −0.33824 | 0.075 (2)* | |
H20B | 0.47445 | −0.13006 | −0.38610 | 0.075 (2)* | |
H22A | 0.55563 | −0.13363 | −0.06204 | 0.075 (2)* | |
H22B | 0.54271 | −0.08055 | −0.30988 | 0.075 (2)* | |
H25 | 0.48214 | −0.29038 | −0.09734 | 0.075 (2)* | |
H27 | 0.45458 | −0.37220 | 0.28522 | 0.075 (2)* | |
H29 | 0.38066 | −0.05122 | 0.06087 | 0.075 (2)* | |
H30 | 0.39547 | −0.34216 | 0.59768 | 0.075 (2)* | |
H31 | 0.33582 | −0.09177 | 0.37124 | 0.075 (2)* | |
H32 | 0.34663 | −0.21461 | 0.67426 | 0.075 (2)* |
O14—C12 | 1.246 (7) | C24—C26 | 1.433 (7) |
O18—C16 | 1.224 (7) | C26—C28 | 1.425 (6) |
O23—C21 | 1.192 (7) | C26—C29 | 1.421 (8) |
N13—C12 | 1.397 (8) | C28—C30 | 1.375 (8) |
N13—C15 | 1.462 (10) | C29—C31 | 1.375 (9) |
N17—C16 | 1.298 (8) | C30—C32 | 1.449 (9) |
N17—C19 | 1.448 (8) | C31—C32 | 1.348 (9) |
N22—C21 | 1.357 (8) | C2—H2 | 0.9300 |
N27—C25 | 1.377 (9) | C3—H3 | 0.9300 |
N27—C28 | 1.337 (8) | C4—H4 | 0.9300 |
N13—H13 | 0.8600 | C5—H5 | 0.9300 |
N17—H17 | 0.8600 | C6—H6 | 0.9300 |
N22—H22A | 0.8600 | C7—H7A | 0.9700 |
N22—H22B | 0.8600 | C7—H7B | 0.9700 |
N27—H27 | 0.8600 | C8—H8A | 0.9700 |
C1—C3 | 1.402 (7) | C8—H8B | 0.9700 |
C1—C2 | 1.377 (8) | C9—H9A | 0.9700 |
C1—C7 | 1.491 (8) | C9—H9B | 0.9700 |
C2—C4 | 1.375 (8) | C10—H10A | 0.9700 |
C3—C5 | 1.373 (9) | C10—H10B | 0.9700 |
C4—C6 | 1.423 (6) | C11—H11A | 0.9700 |
C5—C6 | 1.342 (9) | C11—H11B | 0.9700 |
C7—C8 | 1.521 (9) | C15—H15A | 0.9700 |
C8—C9 | 1.518 (9) | C15—H15B | 0.9700 |
C9—C10 | 1.506 (9) | C19—H19 | 0.9800 |
C10—C11 | 1.457 (9) | C20—H20A | 0.9700 |
C11—C12 | 1.475 (8) | C20—H20B | 0.9700 |
C15—C16 | 1.474 (9) | C25—H25 | 0.9300 |
C19—C20 | 1.570 (8) | C29—H29 | 0.9300 |
C19—C21 | 1.532 (7) | C30—H30 | 0.9300 |
C20—C24 | 1.530 (8) | C31—H31 | 0.9300 |
C24—C25 | 1.346 (8) | C32—H32 | 0.9300 |
C12—N13—C15 | 119.3 (4) | C5—C3—H3 | 118.00 |
C16—N17—C19 | 123.6 (4) | C2—C4—H4 | 120.00 |
C25—N27—C28 | 108.7 (5) | C6—C4—H4 | 119.00 |
C12—N13—H13 | 120.00 | C3—C5—H5 | 119.00 |
C15—N13—H13 | 118.00 | C6—C5—H5 | 121.00 |
C16—N17—H17 | 118.00 | C4—C6—H6 | 119.00 |
C19—N17—H17 | 119.00 | C5—C6—H6 | 119.00 |
H22A—N22—H22B | 120.00 | C1—C7—H7A | 108.00 |
C21—N22—H22B | 119.00 | C1—C7—H7B | 108.00 |
C21—N22—H22A | 118.00 | C8—C7—H7A | 108.00 |
C25—N27—H27 | 124.00 | C8—C7—H7B | 110.00 |
C28—N27—H27 | 123.00 | H7A—C7—H7B | 109.00 |
C2—C1—C3 | 118.9 (5) | C7—C8—H8A | 109.00 |
C2—C1—C7 | 120.0 (4) | C7—C8—H8B | 108.00 |
C3—C1—C7 | 120.3 (5) | C9—C8—H8A | 108.00 |
C1—C2—C4 | 119.9 (4) | C9—C8—H8B | 111.00 |
C1—C3—C5 | 120.7 (6) | H8A—C8—H8B | 109.00 |
C2—C4—C6 | 118.9 (5) | C8—C9—H9A | 109.00 |
C3—C5—C6 | 120.0 (5) | C8—C9—H9B | 108.00 |
C4—C6—C5 | 119.5 (5) | C10—C9—H9A | 109.00 |
C1—C7—C8 | 113.2 (5) | C10—C9—H9B | 108.00 |
C7—C8—C9 | 111.3 (4) | H9A—C9—H9B | 109.00 |
C8—C9—C10 | 113.7 (5) | C9—C10—H10A | 107.00 |
C9—C10—C11 | 111.7 (5) | C9—C10—H10B | 113.00 |
C10—C11—C12 | 113.4 (4) | C11—C10—H10A | 110.00 |
O14—C12—N13 | 120.4 (6) | C11—C10—H10B | 106.00 |
O14—C12—C11 | 121.9 (5) | H10A—C10—H10B | 109.00 |
N13—C12—C11 | 115.6 (4) | C10—C11—H11A | 107.00 |
N13—C15—C16 | 108.9 (4) | C10—C11—H11B | 108.00 |
N17—C16—C15 | 116.0 (4) | C12—C11—H11A | 111.00 |
O18—C16—C15 | 121.3 (6) | C12—C11—H11B | 107.00 |
O18—C16—N17 | 122.0 (5) | H11A—C11—H11B | 109.00 |
N17—C19—C21 | 110.7 (4) | N13—C15—H15A | 108.00 |
C20—C19—C21 | 113.9 (4) | N13—C15—H15B | 111.00 |
N17—C19—C20 | 109.5 (5) | C16—C15—H15A | 110.00 |
C19—C20—C24 | 116.0 (4) | C16—C15—H15B | 108.00 |
O23—C21—C19 | 118.5 (5) | H15A—C15—H15B | 109.00 |
O23—C21—N22 | 122.4 (5) | N17—C19—H19 | 106.00 |
N22—C21—C19 | 115.5 (4) | C20—C19—H19 | 108.00 |
C20—C24—C26 | 130.5 (5) | C21—C19—H19 | 108.00 |
C25—C24—C26 | 105.7 (5) | C19—C20—H20A | 108.00 |
C20—C24—C25 | 123.8 (5) | C19—C20—H20B | 107.00 |
N27—C25—C24 | 110.6 (6) | C24—C20—H20A | 106.00 |
C24—C26—C28 | 106.6 (4) | C24—C20—H20B | 110.00 |
C24—C26—C29 | 134.5 (4) | H20A—C20—H20B | 109.00 |
C28—C26—C29 | 117.7 (5) | N27—C25—H25 | 121.00 |
C26—C28—C30 | 122.2 (4) | C24—C25—H25 | 121.00 |
N27—C28—C30 | 130.5 (5) | C26—C29—H29 | 117.00 |
N27—C28—C26 | 107.3 (5) | C31—C29—H29 | 118.00 |
C26—C29—C31 | 119.0 (5) | C28—C30—H30 | 118.00 |
C28—C30—C32 | 116.7 (5) | C32—C30—H30 | 123.00 |
C29—C31—C32 | 121.1 (6) | C29—C31—H31 | 121.00 |
C30—C32—C31 | 121.1 (6) | C32—C31—H31 | 118.00 |
C1—C2—H2 | 121.00 | C30—C32—H32 | 121.00 |
C4—C2—H2 | 119.00 | C31—C32—H32 | 117.00 |
C1—C3—H3 | 120.00 | ||
C12—N13—C15—C16 | −176.3 (6) | N13—C15—C16—O18 | −3.4 (10) |
C15—N13—C12—O14 | 12.2 (10) | N17—C19—C21—O23 | 27.5 (7) |
C15—N13—C12—C11 | 175.9 (7) | C21—C19—C20—C24 | 57.5 (6) |
C19—N17—C16—C15 | −172.8 (6) | C20—C19—C21—N22 | 62.8 (6) |
C16—N17—C19—C20 | −92.2 (7) | N17—C19—C21—N22 | −173.3 (5) |
C19—N17—C16—O18 | 16.8 (10) | C20—C19—C21—O23 | −96.4 (6) |
C16—N17—C19—C21 | 141.5 (6) | N17—C19—C20—C24 | −67.0 (6) |
C25—N27—C28—C26 | 10.1 (7) | C19—C20—C24—C25 | −92.6 (7) |
C25—N27—C28—C30 | −173.2 (6) | C19—C20—C24—C26 | 86.0 (7) |
C28—N27—C25—C24 | −10.7 (8) | C20—C24—C26—C28 | −178.9 (5) |
C3—C1—C7—C8 | −125.9 (6) | C26—C24—C25—N27 | 6.3 (7) |
C7—C1—C3—C5 | −175.2 (6) | C25—C24—C26—C29 | 167.1 (6) |
C3—C1—C2—C4 | 0.5 (9) | C20—C24—C26—C29 | −11.7 (10) |
C2—C1—C7—C8 | 64.4 (7) | C25—C24—C26—C28 | −0.1 (6) |
C7—C1—C2—C4 | 170.3 (6) | C20—C24—C25—N27 | −174.8 (5) |
C2—C1—C3—C5 | −5.4 (9) | C24—C26—C28—C30 | 176.7 (5) |
C1—C2—C4—C6 | 10.6 (9) | C29—C26—C28—N27 | −175.9 (5) |
C1—C3—C5—C6 | −1.4 (10) | C24—C26—C29—C31 | 179.8 (6) |
C2—C4—C6—C5 | −17.4 (9) | C28—C26—C29—C31 | −14.2 (8) |
C3—C5—C6—C4 | 12.7 (10) | C29—C26—C28—C30 | 7.1 (8) |
C1—C7—C8—C9 | −171.2 (5) | C24—C26—C28—N27 | −6.3 (6) |
C7—C8—C9—C10 | −178.5 (5) | N27—C28—C30—C32 | −179.4 (6) |
C8—C9—C10—C11 | 177.1 (5) | C26—C28—C30—C32 | −3.1 (8) |
C9—C10—C11—C12 | −177.8 (5) | C26—C29—C31—C32 | 18.2 (9) |
C10—C11—C12—O14 | −32.2 (9) | C28—C30—C32—C31 | 6.5 (9) |
C10—C11—C12—N13 | 164.3 (6) | C29—C31—C32—C30 | −14.4 (10) |
N13—C15—C16—N17 | −173.9 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N13—H13···O14i | 0.8600 | 2.5400 | 3.252 (7) | 141.00 |
N13—H13···O18 | 0.8600 | 2.2600 | 2.605 (9) | 104.00 |
N22—H22A···O14ii | 0.8600 | 2.2400 | 2.866 (10) | 129.00 |
N22—H22B···O23i | 0.8600 | 2.4800 | 3.282 (9) | 156.00 |
N27—H27···O23ii | 0.8600 | 2.4000 | 3.146 (8) | 146.00 |
C15—H15A···O18iii | 0.9700 | 2.4800 | 2.906 (9) | 107.00 |
C15—H15B···O18iii | 0.9700 | 2.4900 | 2.906 (9) | 106.00 |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, y−1/2, −z+1/2; (iii) x, y, z+1. |