Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803016386/tk6119sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803016386/tk6119Isup2.hkl |
CCDC reference: 222853
Key indicators
- Single-crystal X-ray study
- T = 180 K
- Mean (C-C) = 0.004 Å
- R factor = 0.051
- wR factor = 0.138
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full too Low ............ 24.70 Deg.
Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) . 3.98 Ratio
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.753 0.989 Tmin' and Tmax expected: 0.964 0.989 RR' = 0.781 Please check that your absorption correction is appropriate. THETM01_ALERT_3_C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5880 PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6]... 24.70 Deg. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ........... 0.78 PLAT220_ALERT_2_C Large Non-Solvent N Ueq(max)/Ueq(min) . 2.62 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) . 3.58 Ratio
1 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Compound (I) was synthesized according to a published procedure (Ghiladi et al., 1997). The raw product was subjected to column chromatography with acetone as eluent. Prismatic crystals suitable for diffraction were formed by subsequent recrystallization from acetone.
All H atoms could be located from a Fourier difference map. The phenol proton was refined isotropically in the riding mode, with Uiso(H1) = 1.2Ueq(O1) and the bond length O1—H1 restrained to 0.90 (5) Å. The remaining ligand H atoms were constrained to ideal positions with Uiso = 1.2Ueq(parent atom).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).
Fig. 1. View of (I) (50% probability displacement ellipsoids). Only the phenolic H atom is included. The excluded atom numbers are consecutive to those included. |
C36H40N6O | F(000) = 1224 |
Mr = 572.74 | Dx = 1.199 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2yn | Cell parameters from 16912 reflections |
a = 9.892 (5) Å | θ = 3.7–24.7° |
b = 31.185 (5) Å | µ = 0.07 mm−1 |
c = 10.524 (5) Å | T = 180 K |
β = 102.188 (5)° | Prism, colourless |
V = 3173 (2) Å3 | 0.48 × 0.35 × 0.15 mm |
Z = 4 |
Bruker SMART CCD diffractometer | 3501 reflections with I > 2σ(I) |
Narrow–frame ϕ and ω scans | Rint = 0.052 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | θmax = 24.7°, θmin = 3.7° |
Tmin = 0.753, Tmax = 0.989 | h = −11→11 |
16542 measured reflections | k = −36→27 |
5388 independent reflections | l = −12→12 |
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0705P)2 + 0.1173P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.051 | (Δ/σ)max = 0.001 |
wR(F2) = 0.138 | Δρmax = 0.32 e Å−3 |
S = 1.02 | Δρmin = −0.18 e Å−3 |
5388 reflections | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
392 parameters | Extinction coefficient: 0.0053 (9) |
1 restraint |
C36H40N6O | V = 3173 (2) Å3 |
Mr = 572.74 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.892 (5) Å | µ = 0.07 mm−1 |
b = 31.185 (5) Å | T = 180 K |
c = 10.524 (5) Å | 0.48 × 0.35 × 0.15 mm |
β = 102.188 (5)° |
Bruker SMART CCD diffractometer | 5388 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3501 reflections with I > 2σ(I) |
Tmin = 0.753, Tmax = 0.989 | Rint = 0.052 |
16542 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 1 restraint |
wR(F2) = 0.138 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.32 e Å−3 |
5388 reflections | Δρmin = −0.18 e Å−3 |
392 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.5137 (2) | 0.31570 (6) | 0.57854 (19) | 0.0279 (5) | |
C2 | 0.6341 (2) | 0.30429 (6) | 0.66721 (19) | 0.0281 (5) | |
C3 | 0.7047 (2) | 0.33577 (6) | 0.7494 (2) | 0.0306 (5) | |
H3 | 0.7851 | 0.3278 | 0.8117 | 0.037* | |
C4 | 0.6621 (2) | 0.37820 (6) | 0.74369 (19) | 0.0281 (5) | |
C5 | 0.5430 (2) | 0.38842 (6) | 0.6520 (2) | 0.0297 (5) | |
H5 | 0.513 | 0.4174 | 0.6444 | 0.036* | |
C6 | 0.46649 (19) | 0.35799 (6) | 0.57161 (19) | 0.0271 (5) | |
C7 | 0.7375 (2) | 0.41262 (7) | 0.8354 (2) | 0.0351 (5) | |
C8 | 0.8608 (3) | 0.39482 (8) | 0.9322 (3) | 0.0588 (7) | |
H8A | 0.9057 | 0.418 | 0.9885 | 0.088* | |
H8B | 0.9269 | 0.3823 | 0.8852 | 0.088* | |
H8C | 0.8293 | 0.3727 | 0.9854 | 0.088* | |
C9 | 0.7857 (3) | 0.44876 (7) | 0.7585 (3) | 0.0570 (7) | |
H9A | 0.7063 | 0.4604 | 0.6963 | 0.086* | |
H9B | 0.8538 | 0.4377 | 0.7114 | 0.086* | |
H9C | 0.8279 | 0.4715 | 0.8182 | 0.086* | |
C10 | 0.6362 (3) | 0.43104 (8) | 0.9138 (3) | 0.0562 (7) | |
H10A | 0.555 | 0.4427 | 0.8541 | 0.084* | |
H10B | 0.682 | 0.4539 | 0.9711 | 0.084* | |
H10C | 0.6071 | 0.4082 | 0.9663 | 0.084* | |
C20 | 0.6933 (2) | 0.25973 (6) | 0.6688 (2) | 0.0347 (5) | |
H20A | 0.7364 | 0.2561 | 0.5927 | 0.042* | |
H20B | 0.7664 | 0.256 | 0.7483 | 0.042* | |
C60 | 0.3339 (2) | 0.36825 (6) | 0.4758 (2) | 0.0325 (5) | |
H60A | 0.3482 | 0.363 | 0.3868 | 0.039* | |
H60B | 0.2611 | 0.3483 | 0.4908 | 0.039* | |
C211 | 0.5445 (2) | 0.22486 (7) | 0.7908 (2) | 0.0440 (6) | |
H21A | 0.5342 | 0.2545 | 0.821 | 0.053* | |
H21B | 0.6187 | 0.2109 | 0.8553 | 0.053* | |
C212 | 0.4117 (3) | 0.20117 (7) | 0.7865 (3) | 0.0522 (7) | |
C213 | 0.3070 (3) | 0.19958 (8) | 0.6781 (3) | 0.0670 (8) | |
H213 | 0.3186 | 0.2123 | 0.5991 | 0.08* | |
C214 | 0.1843 (3) | 0.17943 (10) | 0.6846 (4) | 0.0917 (12) | |
H214 | 0.1106 | 0.178 | 0.6104 | 0.11* | |
C215 | 0.1712 (5) | 0.16162 (12) | 0.7997 (6) | 0.1076 (17) | |
H215 | 0.0878 | 0.1477 | 0.8073 | 0.129* | |
C216 | 0.2772 (5) | 0.16401 (10) | 0.9017 (5) | 0.0994 (15) | |
H216 | 0.2659 | 0.1514 | 0.9809 | 0.119* | |
C221 | 0.6357 (2) | 0.18476 (6) | 0.6305 (2) | 0.0371 (5) | |
H22A | 0.565 | 0.1627 | 0.6352 | 0.045* | |
H22B | 0.7214 | 0.1769 | 0.6935 | 0.045* | |
C222 | 0.6642 (2) | 0.18537 (6) | 0.4957 (2) | 0.0335 (5) | |
C223 | 0.7856 (2) | 0.16950 (7) | 0.4706 (3) | 0.0458 (6) | |
H223 | 0.852 | 0.1565 | 0.538 | 0.055* | |
C224 | 0.8099 (3) | 0.17258 (8) | 0.3469 (3) | 0.0586 (8) | |
H224 | 0.8933 | 0.1619 | 0.3277 | 0.07* | |
C225 | 0.7122 (3) | 0.19128 (8) | 0.2525 (3) | 0.0595 (7) | |
H225 | 0.7267 | 0.1944 | 0.1666 | 0.071* | |
C226 | 0.5929 (3) | 0.20538 (8) | 0.2846 (3) | 0.0581 (7) | |
H226 | 0.5241 | 0.2176 | 0.2176 | 0.07* | |
C611 | 0.2245 (2) | 0.41865 (6) | 0.5967 (2) | 0.0335 (5) | |
H61A | 0.2825 | 0.4038 | 0.672 | 0.04* | |
H61B | 0.1313 | 0.4055 | 0.5805 | 0.04* | |
C612 | 0.2127 (2) | 0.46535 (7) | 0.6302 (2) | 0.0314 (5) | |
C613 | 0.2735 (2) | 0.49812 (7) | 0.5739 (2) | 0.0377 (5) | |
H613 | 0.3275 | 0.4918 | 0.5115 | 0.045* | |
C614 | 0.2554 (2) | 0.53993 (7) | 0.6087 (2) | 0.0430 (6) | |
H614 | 0.2948 | 0.5628 | 0.5694 | 0.052* | |
C615 | 0.1790 (2) | 0.54801 (7) | 0.7015 (2) | 0.0440 (6) | |
H615 | 0.1652 | 0.5765 | 0.7284 | 0.053* | |
C616 | 0.1236 (2) | 0.51353 (7) | 0.7540 (2) | 0.0434 (6) | |
H616 | 0.0722 | 0.5191 | 0.819 | 0.052* | |
C621 | 0.1816 (2) | 0.42173 (7) | 0.36475 (19) | 0.0312 (5) | |
H62A | 0.1275 | 0.4471 | 0.381 | 0.037* | |
H62B | 0.117 | 0.3972 | 0.345 | 0.037* | |
C622 | 0.2430 (2) | 0.43048 (6) | 0.2480 (2) | 0.0296 (5) | |
C623 | 0.3810 (2) | 0.44006 (7) | 0.2575 (2) | 0.0375 (5) | |
H623 | 0.4435 | 0.44 | 0.3395 | 0.045* | |
C624 | 0.4266 (2) | 0.44976 (7) | 0.1458 (2) | 0.0459 (6) | |
H624 | 0.5211 | 0.4564 | 0.1495 | 0.055* | |
C625 | 0.3331 (2) | 0.44972 (7) | 0.0291 (2) | 0.0441 (6) | |
H625 | 0.3613 | 0.4567 | −0.0492 | 0.053* | |
C626 | 0.1985 (2) | 0.43950 (7) | 0.0279 (2) | 0.0405 (6) | |
H626 | 0.1348 | 0.4392 | −0.0534 | 0.049* | |
N2 | 0.58677 (18) | 0.22663 (5) | 0.66572 (17) | 0.0328 (4) | |
N6 | 0.28431 (16) | 0.41209 (5) | 0.48279 (16) | 0.0292 (4) | |
N211 | 0.3999 (3) | 0.18311 (7) | 0.9004 (2) | 0.0767 (8) | |
N221 | 0.5666 (2) | 0.20307 (6) | 0.4039 (2) | 0.0473 (5) | |
N611 | 0.13705 (18) | 0.47286 (6) | 0.71994 (17) | 0.0390 (5) | |
N621 | 0.15145 (18) | 0.42993 (5) | 0.13452 (17) | 0.0354 (4) | |
O1 | 0.43944 (14) | 0.28727 (4) | 0.49318 (14) | 0.0369 (4) | |
H1 | 0.470 (2) | 0.2615 (6) | 0.509 (2) | 0.044* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0305 (11) | 0.0295 (11) | 0.0233 (12) | −0.0045 (9) | 0.0050 (9) | −0.0032 (9) |
C2 | 0.0292 (11) | 0.0296 (11) | 0.0253 (12) | 0.0000 (9) | 0.0052 (9) | 0.0008 (9) |
C3 | 0.0282 (11) | 0.0363 (12) | 0.0256 (12) | 0.0012 (9) | 0.0019 (9) | 0.0030 (9) |
C4 | 0.0286 (11) | 0.0321 (11) | 0.0243 (12) | −0.0011 (9) | 0.0071 (9) | 0.0004 (9) |
C5 | 0.0334 (12) | 0.0273 (11) | 0.0284 (12) | 0.0024 (9) | 0.0066 (10) | 0.0002 (9) |
C6 | 0.0281 (11) | 0.0303 (11) | 0.0218 (12) | 0.0014 (9) | 0.0029 (9) | 0.0018 (8) |
C7 | 0.0346 (12) | 0.0359 (12) | 0.0327 (13) | −0.0032 (9) | 0.0024 (10) | −0.0046 (9) |
C8 | 0.0576 (16) | 0.0527 (15) | 0.0534 (18) | −0.0077 (13) | −0.0169 (14) | −0.0122 (12) |
C9 | 0.0638 (17) | 0.0492 (15) | 0.0575 (19) | −0.0184 (13) | 0.0116 (14) | −0.0031 (13) |
C10 | 0.0575 (16) | 0.0631 (17) | 0.0480 (17) | −0.0062 (13) | 0.0108 (14) | −0.0213 (13) |
C20 | 0.0332 (12) | 0.0322 (12) | 0.0364 (14) | 0.0015 (9) | 0.0024 (10) | −0.0010 (9) |
C60 | 0.0347 (12) | 0.0333 (12) | 0.0265 (12) | 0.0026 (9) | −0.0003 (10) | −0.0007 (9) |
C211 | 0.0613 (16) | 0.0387 (13) | 0.0351 (15) | 0.0027 (11) | 0.0172 (12) | 0.0003 (10) |
C212 | 0.0758 (19) | 0.0337 (13) | 0.0601 (19) | 0.0023 (12) | 0.0436 (17) | −0.0019 (12) |
C213 | 0.0631 (19) | 0.0626 (18) | 0.082 (2) | −0.0084 (15) | 0.0300 (18) | 0.0016 (16) |
C214 | 0.065 (2) | 0.084 (2) | 0.139 (4) | −0.0145 (17) | 0.050 (2) | −0.011 (2) |
C215 | 0.113 (3) | 0.074 (2) | 0.169 (5) | −0.025 (2) | 0.105 (4) | −0.030 (3) |
C216 | 0.154 (4) | 0.059 (2) | 0.122 (4) | −0.023 (3) | 0.114 (3) | −0.011 (2) |
C221 | 0.0429 (13) | 0.0276 (12) | 0.0419 (14) | 0.0032 (10) | 0.0111 (11) | 0.0036 (10) |
C222 | 0.0380 (12) | 0.0231 (11) | 0.0404 (14) | −0.0017 (9) | 0.0102 (11) | −0.0050 (9) |
C223 | 0.0415 (14) | 0.0460 (14) | 0.0514 (17) | 0.0059 (11) | 0.0129 (13) | −0.0057 (11) |
C224 | 0.0571 (17) | 0.0565 (17) | 0.070 (2) | 0.0039 (13) | 0.0307 (17) | −0.0135 (14) |
C225 | 0.083 (2) | 0.0545 (16) | 0.0502 (18) | 0.0003 (15) | 0.0345 (17) | −0.0077 (13) |
C226 | 0.0695 (18) | 0.0668 (18) | 0.0403 (17) | 0.0095 (14) | 0.0169 (15) | 0.0072 (13) |
C611 | 0.0332 (12) | 0.0412 (13) | 0.0258 (13) | 0.0029 (10) | 0.0060 (10) | 0.0028 (9) |
C612 | 0.0283 (11) | 0.0408 (13) | 0.0231 (12) | 0.0056 (9) | 0.0006 (10) | 0.0002 (9) |
C613 | 0.0370 (12) | 0.0404 (13) | 0.0368 (14) | 0.0014 (10) | 0.0104 (11) | −0.0023 (10) |
C614 | 0.0407 (13) | 0.0427 (14) | 0.0446 (16) | −0.0010 (11) | 0.0068 (12) | −0.0007 (11) |
C615 | 0.0405 (13) | 0.0419 (14) | 0.0449 (16) | 0.0074 (11) | −0.0014 (12) | −0.0103 (11) |
C616 | 0.0405 (13) | 0.0561 (16) | 0.0338 (14) | 0.0134 (12) | 0.0081 (11) | −0.0055 (11) |
C621 | 0.0277 (11) | 0.0374 (12) | 0.0263 (13) | 0.0037 (9) | 0.0006 (10) | 0.0016 (9) |
C622 | 0.0348 (12) | 0.0280 (11) | 0.0242 (12) | 0.0037 (9) | 0.0018 (10) | −0.0001 (9) |
C623 | 0.0327 (12) | 0.0492 (14) | 0.0289 (13) | 0.0016 (10) | 0.0024 (10) | 0.0017 (10) |
C624 | 0.0368 (13) | 0.0610 (16) | 0.0407 (16) | 0.0001 (11) | 0.0099 (12) | 0.0008 (12) |
C625 | 0.0478 (14) | 0.0559 (15) | 0.0302 (14) | 0.0015 (12) | 0.0119 (12) | 0.0037 (11) |
C626 | 0.0453 (14) | 0.0487 (14) | 0.0244 (14) | 0.0007 (11) | 0.0003 (11) | 0.0012 (10) |
N2 | 0.0400 (10) | 0.0272 (9) | 0.0328 (11) | 0.0006 (8) | 0.0115 (9) | 0.0002 (7) |
N6 | 0.0312 (9) | 0.0349 (10) | 0.0194 (10) | 0.0058 (7) | 0.0007 (8) | −0.0003 (7) |
N211 | 0.127 (2) | 0.0517 (14) | 0.0702 (18) | −0.0082 (14) | 0.0647 (17) | −0.0038 (12) |
N221 | 0.0487 (12) | 0.0536 (12) | 0.0416 (13) | 0.0098 (10) | 0.0141 (10) | 0.0081 (10) |
N611 | 0.0401 (11) | 0.0484 (12) | 0.0286 (11) | 0.0086 (9) | 0.0075 (9) | 0.0012 (9) |
N621 | 0.0373 (10) | 0.0425 (11) | 0.0238 (11) | −0.0004 (8) | 0.0006 (9) | 0.0018 (8) |
O1 | 0.0410 (9) | 0.0290 (8) | 0.0350 (9) | 0.0016 (7) | −0.0048 (7) | −0.0061 (7) |
C1—O1 | 1.362 (2) | C221—N2 | 1.467 (2) |
C1—C2 | 1.395 (3) | C221—C222 | 1.503 (3) |
C1—C6 | 1.396 (3) | C221—H22A | 0.99 |
C2—C3 | 1.395 (3) | C221—H22B | 0.99 |
C2—C20 | 1.507 (3) | C222—N221 | 1.332 (3) |
C3—C4 | 1.386 (3) | C222—C223 | 1.375 (3) |
C3—H3 | 0.95 | C223—C224 | 1.376 (3) |
C4—C5 | 1.393 (3) | C223—H223 | 0.95 |
C4—C7 | 1.528 (3) | C224—C225 | 1.362 (4) |
C5—C6 | 1.386 (3) | C224—H224 | 0.95 |
C5—H5 | 0.95 | C225—C226 | 1.367 (4) |
C6—C60 | 1.511 (3) | C225—H225 | 0.95 |
C7—C8 | 1.520 (3) | C226—N221 | 1.338 (3) |
C7—C9 | 1.522 (3) | C226—H226 | 0.95 |
C7—C10 | 1.537 (3) | C611—N6 | 1.459 (3) |
C8—H8A | 0.98 | C611—C612 | 1.509 (3) |
C8—H8B | 0.98 | C611—H61A | 0.99 |
C8—H8C | 0.98 | C611—H61B | 0.99 |
C9—H9A | 0.98 | C612—N611 | 1.343 (3) |
C9—H9B | 0.98 | C612—C613 | 1.381 (3) |
C9—H9C | 0.98 | C613—C614 | 1.376 (3) |
C10—H10A | 0.98 | C613—H613 | 0.95 |
C10—H10B | 0.98 | C614—C615 | 1.378 (3) |
C10—H10C | 0.98 | C614—H614 | 0.95 |
C20—N2 | 1.471 (2) | C615—C616 | 1.375 (3) |
C20—H20A | 0.99 | C615—H615 | 0.95 |
C20—H20B | 0.99 | C616—N611 | 1.332 (3) |
C60—N6 | 1.459 (2) | C616—H616 | 0.95 |
C60—H60A | 0.99 | C621—N6 | 1.460 (2) |
C60—H60B | 0.99 | C621—C622 | 1.506 (3) |
C211—N2 | 1.464 (3) | C621—H62A | 0.99 |
C211—C212 | 1.499 (3) | C621—H62B | 0.99 |
C211—H21A | 0.99 | C622—N621 | 1.338 (3) |
C211—H21B | 0.99 | C622—C623 | 1.380 (3) |
C212—N211 | 1.352 (3) | C623—C624 | 1.379 (3) |
C212—C213 | 1.370 (4) | C623—H623 | 0.95 |
C213—C214 | 1.381 (4) | C624—C625 | 1.372 (3) |
C213—H213 | 0.95 | C624—H624 | 0.95 |
C214—C215 | 1.364 (5) | C625—C626 | 1.366 (3) |
C214—H214 | 0.95 | C625—H625 | 0.95 |
C215—C216 | 1.335 (6) | C626—N621 | 1.336 (3) |
C215—H215 | 0.95 | C626—H626 | 0.95 |
C216—N211 | 1.354 (4) | O1—H1 | 0.863 (19) |
C216—H216 | 0.95 | ||
O1—C1—C2 | 122.73 (17) | N2—C221—C222 | 111.41 (16) |
O1—C1—C6 | 116.91 (17) | N2—C221—H22A | 109.3 |
C2—C1—C6 | 120.33 (17) | C222—C221—H22A | 109.3 |
C3—C2—C1 | 118.73 (18) | N2—C221—H22B | 109.3 |
C3—C2—C20 | 119.93 (18) | C222—C221—H22B | 109.3 |
C1—C2—C20 | 121.20 (17) | H22A—C221—H22B | 108 |
C4—C3—C2 | 122.48 (19) | N221—C222—C223 | 122.6 (2) |
C4—C3—H3 | 118.8 | N221—C222—C221 | 115.96 (19) |
C2—C3—H3 | 118.8 | C223—C222—C221 | 121.4 (2) |
C3—C4—C5 | 116.96 (18) | C222—C223—C224 | 119.4 (2) |
C3—C4—C7 | 122.68 (18) | C222—C223—H223 | 120.3 |
C5—C4—C7 | 120.33 (17) | C224—C223—H223 | 120.3 |
C6—C5—C4 | 122.64 (18) | C225—C224—C223 | 118.8 (2) |
C6—C5—H5 | 118.7 | C225—C224—H224 | 120.6 |
C4—C5—H5 | 118.7 | C223—C224—H224 | 120.6 |
C5—C6—C1 | 118.79 (18) | C224—C225—C226 | 118.3 (3) |
C5—C6—C60 | 123.23 (17) | C224—C225—H225 | 120.8 |
C1—C6—C60 | 117.98 (17) | C226—C225—H225 | 120.8 |
C8—C7—C9 | 109.27 (19) | N221—C226—C225 | 124.3 (3) |
C8—C7—C4 | 112.48 (17) | N221—C226—H226 | 117.9 |
C9—C7—C4 | 110.49 (19) | C225—C226—H226 | 117.9 |
C8—C7—C10 | 107.3 (2) | N6—C611—C612 | 113.09 (16) |
C9—C7—C10 | 108.77 (19) | N6—C611—H61A | 109 |
C4—C7—C10 | 108.39 (17) | C612—C611—H61A | 109 |
C7—C8—H8A | 109.5 | N6—C611—H61B | 109 |
C7—C8—H8B | 109.5 | C612—C611—H61B | 109 |
H8A—C8—H8B | 109.5 | H61A—C611—H61B | 107.8 |
C7—C8—H8C | 109.5 | N611—C612—C613 | 122.02 (19) |
H8A—C8—H8C | 109.5 | N611—C612—C611 | 114.49 (18) |
H8B—C8—H8C | 109.5 | C613—C612—C611 | 123.49 (19) |
C7—C9—H9A | 109.5 | C614—C613—C612 | 119.6 (2) |
C7—C9—H9B | 109.5 | C614—C613—H613 | 120.2 |
H9A—C9—H9B | 109.5 | C612—C613—H613 | 120.2 |
C7—C9—H9C | 109.5 | C613—C614—C615 | 118.9 (2) |
H9A—C9—H9C | 109.5 | C613—C614—H614 | 120.5 |
H9B—C9—H9C | 109.5 | C615—C614—H614 | 120.5 |
C7—C10—H10A | 109.5 | C616—C615—C614 | 117.8 (2) |
C7—C10—H10B | 109.5 | C616—C615—H615 | 121.1 |
H10A—C10—H10B | 109.5 | C614—C615—H615 | 121.1 |
C7—C10—H10C | 109.5 | N611—C616—C615 | 124.4 (2) |
H10A—C10—H10C | 109.5 | N611—C616—H616 | 117.8 |
H10B—C10—H10C | 109.5 | C615—C616—H616 | 117.8 |
N2—C20—C2 | 111.81 (16) | N6—C621—C622 | 113.81 (16) |
N2—C20—H20A | 109.3 | N6—C621—H62A | 108.8 |
C2—C20—H20A | 109.3 | C622—C621—H62A | 108.8 |
N2—C20—H20B | 109.3 | N6—C621—H62B | 108.8 |
C2—C20—H20B | 109.3 | C622—C621—H62B | 108.8 |
H20A—C20—H20B | 107.9 | H62A—C621—H62B | 107.7 |
N6—C60—C6 | 114.74 (16) | N621—C622—C623 | 122.7 (2) |
N6—C60—H60A | 108.6 | N621—C622—C621 | 114.36 (18) |
C6—C60—H60A | 108.6 | C623—C622—C621 | 122.90 (19) |
N6—C60—H60B | 108.6 | C624—C623—C622 | 118.9 (2) |
C6—C60—H60B | 108.6 | C624—C623—H623 | 120.6 |
H60A—C60—H60B | 107.6 | C622—C623—H623 | 120.6 |
N2—C211—C212 | 114.0 (2) | C625—C624—C623 | 118.8 (2) |
N2—C211—H21A | 108.8 | C625—C624—H624 | 120.6 |
C212—C211—H21A | 108.8 | C623—C624—H624 | 120.6 |
N2—C211—H21B | 108.8 | C626—C625—C624 | 118.7 (2) |
C212—C211—H21B | 108.8 | C626—C625—H625 | 120.7 |
H21A—C211—H21B | 107.7 | C624—C625—H625 | 120.7 |
N211—C212—C213 | 122.1 (3) | N621—C626—C625 | 123.8 (2) |
N211—C212—C211 | 114.7 (3) | N621—C626—H626 | 118.1 |
C213—C212—C211 | 123.2 (2) | C625—C626—H626 | 118.1 |
C212—C213—C214 | 119.6 (3) | C211—N2—C221 | 111.48 (16) |
C212—C213—H213 | 120.2 | C211—N2—C20 | 110.24 (17) |
C214—C213—H213 | 120.2 | C221—N2—C20 | 110.91 (16) |
C215—C214—C213 | 118.6 (4) | C611—N6—C60 | 111.80 (16) |
C215—C214—H214 | 120.7 | C611—N6—C621 | 109.89 (16) |
C213—C214—H214 | 120.7 | C60—N6—C621 | 109.32 (15) |
C216—C215—C214 | 119.0 (4) | C212—N211—C216 | 116.0 (3) |
C216—C215—H215 | 120.5 | C222—N221—C226 | 116.7 (2) |
C214—C215—H215 | 120.5 | C616—N611—C612 | 117.20 (19) |
C215—C216—N211 | 124.7 (4) | C626—N621—C622 | 117.15 (19) |
C215—C216—H216 | 117.6 | C1—O1—H1 | 111.1 (15) |
N211—C216—H216 | 117.6 | ||
O1—C1—C2—C3 | 178.88 (18) | C224—C225—C226—N221 | 1.8 (4) |
C6—C1—C2—C3 | 0.8 (3) | N6—C611—C612—N611 | 169.15 (17) |
O1—C1—C2—C20 | 3.2 (3) | N6—C611—C612—C613 | −10.6 (3) |
C6—C1—C2—C20 | −174.90 (18) | N611—C612—C613—C614 | −0.9 (3) |
C1—C2—C3—C4 | −1.9 (3) | C611—C612—C613—C614 | 178.9 (2) |
C20—C2—C3—C4 | 173.80 (18) | C612—C613—C614—C615 | 1.4 (3) |
C2—C3—C4—C5 | 0.7 (3) | C613—C614—C615—C616 | −0.6 (3) |
C2—C3—C4—C7 | 178.71 (19) | C614—C615—C616—N611 | −1.0 (3) |
C3—C4—C5—C6 | 1.8 (3) | N6—C621—C622—N621 | 165.90 (16) |
C7—C4—C5—C6 | −176.29 (19) | N6—C621—C622—C623 | −16.7 (3) |
C4—C5—C6—C1 | −2.9 (3) | N621—C622—C623—C624 | 0.4 (3) |
C4—C5—C6—C60 | 177.30 (19) | C621—C622—C623—C624 | −176.72 (19) |
O1—C1—C6—C5 | −176.67 (18) | C622—C623—C624—C625 | 0.3 (3) |
C2—C1—C6—C5 | 1.5 (3) | C623—C624—C625—C626 | −0.9 (3) |
O1—C1—C6—C60 | 3.2 (3) | C624—C625—C626—N621 | 0.8 (3) |
C2—C1—C6—C60 | −178.65 (18) | C212—C211—N2—C221 | −72.1 (2) |
C3—C4—C7—C8 | −0.7 (3) | C212—C211—N2—C20 | 164.25 (17) |
C5—C4—C7—C8 | 177.3 (2) | C222—C221—N2—C211 | 173.69 (18) |
C3—C4—C7—C9 | 121.7 (2) | C222—C221—N2—C20 | −63.1 (2) |
C5—C4—C7—C9 | −60.3 (3) | C2—C20—N2—C211 | −72.1 (2) |
C3—C4—C7—C10 | −119.2 (2) | C2—C20—N2—C221 | 163.96 (17) |
C5—C4—C7—C10 | 58.8 (3) | C612—C611—N6—C60 | 162.33 (16) |
C3—C2—C20—N2 | 136.68 (19) | C612—C611—N6—C621 | −76.1 (2) |
C1—C2—C20—N2 | −47.7 (3) | C6—C60—N6—C611 | −74.3 (2) |
C5—C6—C60—N6 | −5.7 (3) | C6—C60—N6—C621 | 163.80 (16) |
C1—C6—C60—N6 | 174.48 (17) | C622—C621—N6—C611 | 160.51 (16) |
N2—C211—C212—N211 | 152.76 (19) | C622—C621—N6—C60 | −76.4 (2) |
N2—C211—C212—C213 | −30.5 (3) | C213—C212—N211—C216 | −1.1 (4) |
N211—C212—C213—C214 | 0.8 (4) | C211—C212—N211—C216 | 175.7 (2) |
C211—C212—C213—C214 | −175.8 (2) | C215—C216—N211—C212 | 0.8 (5) |
C212—C213—C214—C215 | 0.1 (4) | C223—C222—N221—C226 | −1.0 (3) |
C213—C214—C215—C216 | −0.4 (5) | C221—C222—N221—C226 | 177.4 (2) |
C214—C215—C216—N211 | 0.0 (6) | C225—C226—N221—C222 | −0.6 (4) |
N2—C221—C222—N221 | −46.8 (2) | C615—C616—N611—C612 | 1.5 (3) |
N2—C221—C222—C223 | 131.5 (2) | C613—C612—N611—C616 | −0.6 (3) |
N221—C222—C223—C224 | 1.4 (3) | C611—C612—N611—C616 | 179.63 (18) |
C221—C222—C223—C224 | −176.9 (2) | C625—C626—N621—C622 | −0.1 (3) |
C222—C223—C224—C225 | −0.2 (4) | C623—C622—N621—C626 | −0.5 (3) |
C223—C224—C225—C226 | −1.3 (4) | C621—C622—N621—C626 | 176.88 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2 | 0.86 (2) | 2.11 (2) | 2.807 (2) | 138 (2) |
O1—H1···N221 | 0.86 (2) | 2.43 (2) | 3.140 (2) | 140 (2) |
Experimental details
Crystal data | |
Chemical formula | C36H40N6O |
Mr | 572.74 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 180 |
a, b, c (Å) | 9.892 (5), 31.185 (5), 10.524 (5) |
β (°) | 102.188 (5) |
V (Å3) | 3173 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.48 × 0.35 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.753, 0.989 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16542, 5388, 3501 |
Rint | 0.052 |
(sin θ/λ)max (Å−1) | 0.588 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.138, 1.02 |
No. of reflections | 5388 |
No. of parameters | 392 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.32, −0.18 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2000), SAINT, SIR97 (Altomare, 1999), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), WinGX (Farrugia, 1999).
O1—C1—C2 | 122.73 (17) | C222—N221—C226 | 116.7 (2) |
O1—C1—C6 | 116.91 (17) | C616—N611—C612 | 117.20 (19) |
C212—N211—C216 | 116.0 (3) | C626—N621—C622 | 117.15 (19) |
C1—C2—C20—N2 | −47.7 (3) | C1—C6—C60—N6 | 174.48 (17) |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
We have used the phenolate-hinged dinucleating ligand bpbp− for the synthesis of dimetallic coordination compounds and have succeeded in crystallizing the parent phenol, Hbpbp, (I). This together with the dichloride diperchlorate tetraprotonated double salt of H5bpbp4+ (Gomez et al., 2000) has given us further insight in the mechanism of the ligand coordination.
The conformation of (I) (Fig. 1) is dominated by an intramolecular bifurcated hydrogen bond from the phenol O1—H1 group to N2 [2.11 (2) Å] of one arm and N221 [2.43 (2) Å] of one pyridine of that same arm. The angles around H1 sum to 255 (3)°. This hydrogen bond gives a C1—C2—C20—N2 torsion angle of −47.7 (3)° (syn). The C1—C6—C60—N6 torsion angle on the other hand is 174.48 (17)° (anti). This can be explained by a 2.53 Å hydrogen bond from C5—H5 of the phenol ring to N6 of the other ligand arm. In addition, atoms H613 and H623 of the attached pyridine rings form similar hydrogen bonds to N6 (2.53 and 2.55 Å, respectively). In the previously investigated H5bpbp4+ cation, these C—H donors have been displaced by N—H donors from the protonated pyridines. As a result, both amines are oriented syn to the O—H group.
The molecular packing is dominated by C—H···N [shortest contacts 2.61 Å for H8a···N621i and H626···N611ii; symmetry codes: (i): 1 + x, y, 1 + z; (ii) x, y, −1 + z] and C—H···π bonding [shortest contacts are to the central phenol ring (centroid = PC): H216···PCiii = 2.85 Å and H224···PCiv; symmetry codes: (iii) −1/2 + x, 1/2 − y, 1/2 + z; (iv) 1/2 + x, 1/2 − y, −1/2 + z].
We propose that the asymmetry between the bis(pyridin-2-ylmethyl)aminomethyl arms, one hydrogen-bonded, one dangling, can account for the observed asymmetric coordination chemistry of the bpbp− ligand (Ghiladi et al., 1997, 1999). A stepwise insertion of two metal ions seems likely because the dangling arm is more available for coordination.