Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010001163X/sk1414sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827010001163X/sk1414Isup2.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S010827010001163X/sk1414sup3.pdf |
CCDC reference: 153925
Data collection: CAD-4-PC Software (Enraf-Nonius, 1992); cell refinement: CAD-4-PC Software; data reduction: DATRD2 in NRCVAX96 (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: NRCVAX96 and SHELXL97; molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEX (McArdle, 1995) and PLATON; software used to prepare material for publication: NRCVAX96, SHELXL97 and PREP8 (Ferguson, 1998).
C17H15NO4 | Dx = 1.359 Mg m−3 |
Mr = 297.30 | Melting point: 503 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.7107 Å |
a = 10.7589 (9) Å | Cell parameters from 25 reflections |
b = 17.8696 (17) Å | θ = 9.6–18.6° |
c = 22.6670 (18) Å | µ = 0.10 mm−1 |
V = 4357.9 (7) Å3 | T = 294 K |
Z = 12 | Block, colourless |
F(000) = 1872 | 0.36 × 0.36 × 0.28 mm |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.009 |
Radiation source: X-ray tube | θmax = 25.0°, θmin = 2.1° |
Graphite monochromator | h = −12→12 |
ω/2θ scans | k = 0→21 |
8116 measured reflections | l = 0→26 |
4272 independent reflections | 3 standard reflections every 120 min |
2782 reflections with I > 2σ(I) | intensity decay: <1% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.116 | w = 1/[σ2(Fo2) + (0.063P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
4272 reflections | Δρmax = 0.19 e Å−3 |
602 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0013 (3) |
Experimental. [Synthetic details are in the experimental section]. In compound (I), all atoms bound to C were treated as riding, with the SHELXL97 (Sheldrick, 1997) defaults for C—H distances and with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for the remainder. The H atoms bound to O were located from a difference Fourier map and subsequently treated as a rigid rotating group with Uiso(H) = 1.5Ueq(O). [Further details in addition to the experimental section]. Molecule (I) crystallized in the orthorhombic system, space group P212121 from the systematic absences. All H atoms in (I) were treated as riding atoms with C—H 0.93 to 0.98 Å and O—H 0.82 Å. A complete quadrant of data (±h,+k,+l reflections) was collected for (I). For the SHELXL97 refinement cycles, 7798 refl's were read of which 4272 refl's are unique/independent and giving 2782 refl's > 2sigma(I). The 3526 x2 Friedel reflections were merged in the final refinement cycles. The anomalous dispersion terms for O, N and C are small and the absolute structure was not determined [Flack parameter, -0.8 (13) for the final unmerged refinement data] by our X-ray analysis, but can be inferred from the known absolute configuration of the L-tyrosine used in the synthesis and the chemistry of related structures. A weighting scheme of 0.00 in least squares refinement results in a Flack parameter of -2.3 (11), while the inverted structure gives a value of 1.8 (13), both refinements with Friedels NOT merged. The data were merged for the final refinement cycles. The following text is from the penultimate CHECKCIF/PRINTCIF run. ################################################################# Thank you for using CHECKCIF. Data-validation tests on your CIF entitled Intermolecular O—H···O hydrogen bonding in the three independent molecules of 2(S)-(1-oxoisoindolin-2-yl)-3-(4-hydroxyphenyl)propanoic acid. have shown that there are no serious problems. STRUCTURE: I ———— ADDSYM reports no extra symmetry Alert Level C: ————– STRVAL_01 From the CIF: _refine_ls_abs_structure_Flack 0.600 From the CIF: _refine_ls_abs_structure_Flack_su 1.600 Alert C Flack test results are ambiguous. General Notes ————— REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.0 From the CIF: _reflns_number_total 4272 Count of symmetry unique reflns 4290 Completeness (_total/calc) 99.58% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. 0 Alert Level A = Potentially serious problem 0 Alert Level B = Potential problem 1 Alert Level C = Please check {Addressed in the experimental section} |
Geometry. Selected Geometrical Data EX-PLATON (Spek, 1998) The following data are for the merged data in the final refinement cycles. =================================================== Molfit with Quaternion Transformation Method (see: A·L. Mackay, Acta Cryst.(1984), A40, 165–166) =================================================== Molecules A and B :: Determinant = 0.4008E+08 THETA = 114.74 Direction Cosines with Orth. Cell: L,M,N = -0.255071 - 0.000062 - 0.966923 Components in crystal system -0.555770 - 0.000081 - 1.000000 Transf. Orthogonal Coord. Mol1 Orth. Coord. Mol2 with Resp. to C·G. Dist(A) ——————————————————————————- O(1 A) -2.097 2.243 - 2.596 O(1B) -2.226 2.005 - 2.784 0.330 O(2 A) -0.940 0.528 - 3.394 O(2B) -0.556 0.705 - 3.421 0.423 O(3 A) -1.625 - 1.798 - 0.481 O(3B) -1.772 - 1.811 - 0.862 0.409 O(4 A) -0.858 2.077 5.423 O(4B) -0.568 1.896 5.303 0.362 N(1 A) -0.058 - 0.207 - 0.952 N(1B) -0.147 - 0.197 - 0.876 0.117 C(1 A) -1.308 1.190 - 2.480 C(1B) -1.233 1.170 - 2.564 0.114 C(2 A) -0.979 0.910 - 1.024 C(2B) -1.055 0.920 - 1.081 0.096 C(3 A) -0.464 - 1.478 - 0.797 C(3B) -0.566 - 1.483 - 0.878 0.130 C(4 A) 0.675 - 2.349 - 1.049 C(4B) 0.615 - 2.326 - 0.951 0.118 C(5 A) 0.769 - 3.728 - 0.963 C(5B) 0.706 - 3.705 - 0.965 0.067 C(6 A) 1.971 - 4.295 - 1.273 C(6B) 1.951 - 4.258 - 1.161 0.120 C(7 A) 3.038 - 3.534 - 1.667 C(7B) 3.071 - 3.452 - 1.309 0.369 C(8 A) 2.960 - 2.156 - 1.739 C(8B) 2.975 - 2.092 - 1.259 0.485 C(9 A) 1.738 - 1.561 - 1.423 C(9B) 1.729 - 1.526 - 1.075 0.350 C(10 A) 1.331 - 0.120 - 1.406 C(10B) 1.302 - 0.087 - 1.030 0.378 C(21 A) -0.489 2.127 - 0.236 C(21B) -0.618 2.186 - 0.360 0.189 C(11 A) -0.537 2.006 1.262 C(11B) -0.597 2.059 1.143 0.143 C(12 A) -1.637 1.498 1.951 C(12B) -1.627 1.465 1.836 0.120 C(13 A) -1.720 1.537 3.328 C(13B) -1.632 1.396 3.207 0.206 C(14 A) -0.694 2.062 4.061 C(14B) -0.607 1.955 3.922 0.196 C(15 A) 0.427 2.533 3.417 C(15B) 0.433 2.566 3.273 0.148 C(16 A) 0.497 2.516 2.037 C(16B) 0.422 2.614 1.891 0.191 :: Weighted and Unit Weight RMS-Fit = 0.28 and 0.26 Angstroms Molecules B and C :: Determinant = 0.1567E+06 THETA = 169.68 Direction Cosines with Orth. Cell: L,M,N = -0.407060 - 0.909237 - 0.087124 Components in crystal system -0.743582 - 1.000000 - 0.075541 Transf. Orthogonal Coord. Mol1 Orth. Coord. Mol2 with Resp. to C·G. Dist(A) ——————————————————————————- O(1B) 3.220 - 0.924 2.346 O(1 C) 3.279 - 0.175 2.701 0.831 O(2B) 1.210 - 0.724 3.244 O(2 C) 1.252 - 0.306 3.472 0.478 O(3B) -0.117 - 2.660 0.269 O(3 C) 0.022 - 2.636 0.765 0.516 O(4B) 1.303 2.056 - 5.110 O(4 C) 0.923 1.356 - 5.165 0.799 N(1B) 0.029 - 0.437 0.798 N(1 C) 0.144 - 0.374 0.976 0.221 C(1B) 1.922 - 0.708 2.295 C(1 C) 1.987 - 0.256 2.558 0.527 C(2B) 1.481 - 0.403 0.879 C(2 C) 1.588 - 0.314 1.115 0.274 C(3B) -0.660 - 1.582 0.594 C(3 C) -0.528 - 1.532 0.881 0.320 C(4B) -2.059 - 1.303 0.869 C(4 C) -1.964 - 1.194 0.949 0.165 C(5B) -3.151 - 2.146 0.788 C(5 C) -3.080 - 2.019 0.904 0.186 C(6B) -4.364 - 1.659 1.221 C(6 C) -4.318 - 1.417 0.995 0.334 C(7B) -4.479 - 0.359 1.693 C(7 C) -4.440 - 0.056 1.117 0.653 C(8B) -3.401 0.475 1.737 C(8 C) -3.333 0.761 1.167 0.641 C(9B) -2.178 - 0.006 1.316 C(9 C) -2.096 0.164 1.081 0.302 C(10B) -0.823 0.642 1.295 C(10 C) -0.721 0.784 1.147 0.229 C(21B) 2.077 0.908 0.389 C(21 C) 2.193 0.863 0.310 0.147 C(11B) 1.829 1.185 - 1.074 C(11 C) 1.806 0.934 - 1.135 0.259 C(12B) 1.994 0.214 - 2.035 C(12 C) 1.864 - 0.154 - 1.980 0.394 C(13B) 1.819 0.481 - 3.370 C(13 C) 1.578 - 0.039 - 3.316 0.576 C(14B) 1.500 1.749 - 3.777 C(14 C) 1.220 1.184 - 3.839 0.634 C(15B) 1.337 2.748 - 2.854 C(15 C) 1.163 2.278 - 3.003 0.523 C(16B) 1.509 2.453 - 1.513 C(16 C) 1.461 2.148 - 1.699 0.361 :: Weighted and Unit Weight RMS-Fit = 0.56 and 0.47 Angstroms Molecules A and C :: Determinant = 0.9604E+05 THETA = 169.04 Direction Cosines with Orth. Cell: L,M,N = -0.495380 0.857675 0.137811 Components in crystal system -0.959319 1.000000 0.126673 Transf. Orthogonal Coord. Mol1 Orth. Coord. Mol2 with Resp. to C·G. Dist(A) ——————————————————————————- O(1 A) 2.908 - 0.092 2.776 O(1 C) 3.279 - 0.175 2.701 0.388 O(2 A) 0.801 - 0.107 3.468 O(2 C) 1.252 - 0.306 3.472 0.494 O(3 A) -0.512 - 2.318 0.684 O(3 C) 0.022 - 2.636 0.765 0.627 O(4 A) 2.466 0.018 - 5.327 O(4 C) 0.923 1.356 - 5.165 2.049 N(1 A) -0.183 - 0.076 0.955 N(1 C) 0.144 - 0.374 0.976 0.443 C(1 A) 1.599 - 0.097 2.590 C(1 C) 1.987 - 0.256 2.558 0.420 C(2 A) 1.257 - 0.143 1.111 C(2 C) 1.588 - 0.314 1.115 0.373 C(3 A) -0.957 - 1.170 0.865 C(3 C) -0.528 - 1.532 0.881 0.562 C(4 A) -2.346 - 0.752 1.004 C(4 C) -1.964 - 1.194 0.949 0.587 C(5 A) -3.506 - 1.503 0.930 C(5 C) -3.080 - 2.019 0.904 0.669 C(6 A) -4.689 - 0.849 1.114 C(6 C) -4.318 - 1.417 0.995 0.689 C(7 A) -4.728 0.494 1.377 C(7 C) -4.440 - 0.056 1.117 0.673 C(8 A) -3.577 1.256 1.436 C(8 C) -3.333 0.761 1.167 0.614 C(9 A) -2.359 0.602 1.247 C(9 C) -2.096 0.164 1.081 0.537 C(10 A) -0.958 1.130 1.253 C(10 C) -0.721 0.784 1.147 0.432 C(21 A) 1.988 0.894 0.255 C(21 C) 2.193 0.863 0.310 0.215 C(11 A) 1.998 0.638 - 1.226 C(11 C) 1.806 0.934 - 1.135 0.365 C(12 A) 2.277 - 0.610 - 1.782 C(12 C) 1.864 - 0.154 - 1.980 0.646 C(13 A) 2.430 - 0.788 - 3.142 C(13 C) 1.578 - 0.039 - 3.316 1.148 C(14 A) 2.285 0.272 - 3.991 C(14 C) 1.220 1.184 - 3.839 1.410 C(15 A) 1.967 1.511 - 3.482 C(15 C) 1.163 2.278 - 3.003 1.210 C(16 A) 1.839 1.691 - 2.117 C(16 C) 1.461 2.148 - 1.699 0.726 :: Weighted and Unit Weight RMS-Fit = 1.05 and 0.81 Angstroms Specific hydrogen bonds (with e.s.d.'s except fixed and riding H) ========================================================================== Interaction D—H H···A D—H···A D···A A and symmetry operator ========================================================================== O1A—H1A 0.820 1.843 168.6 2.652 O3A [x - 1/2,-y + 1/2,-z + 2] O4A—H4A 0.820 1.942 170.1 2.753 O4B O1B—H1B 0.820 1.998 145.9 2.716 O3A [x - 1/2,-y + 1/2,-z + 1] O4B—H4B 0.820 1.854 152.0 2.607 O3C O1C—H1C 0.820 1.894 158.8 2.675 O3B [-x - 1/2,-y,z + 1/2] O4C—H4C 0.820 1.995 171.2 2.809 O3B Weaker C—H···O interactions contacts. C10C H10E O1A 3.284 (5) 0.97 2.50 138 3_546 yes C15A H15A O3C 3.425 (6) 0.93 2.54 160 1_555 yes C15C H15C O2B 3.569 (7) 0.93 2.65 173 3_545 yes Mean plane data ex-SHELXL97 for molecules A, B, C in compound (I) ################################################################# Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) -7.2180(0.0136)x + 13.2449(0.0205)y - 0.5265(0.0414)z = 2.8790(0.0318) * 0.0104 (0.0028) C11A * -0.0116 (0.0029) C12A * 0.0009 (0.0030) C13A * 0.0109 (0.0030) C14A * -0.0117 (0.0030) C15A * 0.0011 (0.0030) C16A Rms deviation of fitted atoms = 0.0091 -5.2868(0.0164)x + 15.5520(0.0155)y + 0.7517(0.0428)z = 4.1262(0.0182) Angle to previous plane (with approximate e.s.d.) = 13.1 (2) * -0.0056 (0.0030) C11B * 0.0071 (0.0035) C12B * -0.0049 (0.0035) C13B * 0.0011 (0.0032) C14B * 0.0003 (0.0032) C15B * 0.0019 (0.0032) C16B Rms deviation of fitted atoms = 0.0043 -10.3482(0.0057)x - 3.4864(0.0335)y - 4.3493(0.0425)z = 0.4641(0.0196) Angle to previous plane (with approximate e.s.d.) = 72.75 (13) * -0.0054 (0.0031) C11C * 0.0001 (0.0033) C12C * 0.0036 (0.0035) C13C * -0.0021 (0.0036) C14C * -0.0033 (0.0034) C15C * 0.0071 (0.0032) C16C Rms deviation of fitted atoms = 0.0042 -7.2180(0.0136)x + 13.2449(0.0205)y - 0.5265(0.0414)z = 2.8790(0.0318) Angle to previous plane (with approximate e.s.d.) = 59.66 (13) * 0.0104 (0.0028) C11A * -0.0116 (0.0029) C12A * 0.0009 (0.0030) C13A * 0.0109 (0.0030) C14A * -0.0117 (0.0030) C15A * 0.0011 (0.0030) C16A Rms deviation of fitted atoms = 0.0091 8.6489(0.0151)x + 8.6533(0.0366)y + 7.8283(0.0491)z = 9.3268(0.0470) Angle to previous plane (with approximate e.s.d.) = 79.14 (13) * 0.0034 (0.0012) O1A * 0.0044 (0.0015) O2A * -0.0108 (0.0037) C1A * 0.0030 (0.0010) C2A -0.0841 (0.0067) N1A -1.0397 (0.0073) C21A Rms deviation of fitted atoms = 0.0063 -1.8802(0.0233)x - 0.0292(0.0412)y + 22.3182(0.0090)z = 19.9727(0.0142) Angle to previous plane (with approximate e.s.d.) = 78.53 (18) * 0.0043 (0.0036) C4A * -0.0006 (0.0040) C5A * -0.0057 (0.0047) C6A * 0.0082 (0.0050) C7A * -0.0045 (0.0045) C8A * -0.0017 (0.0038) C9A 0.0231 (0.0077) C3A 0.0776 (0.0090) O3A -0.0106 (0.0082) C10A -0.0405 (0.0082) N1A Rms deviation of fitted atoms = 0.0049 -2.0485(0.0265)x + 0.0627(0.0387)y + 22.2522(0.0110)z = 19.8906(0.0149) Angle to previous plane (with approximate e.s.d.) = 0.96 (12) * -0.0213 (0.0028) N1A * 0.0203 (0.0029) C3A * -0.0107 (0.0030) C4A * -0.0012 (0.0030) C9A * 0.0130 (0.0027) C10A 0.0671 (0.0069) O3A Rms deviation of fitted atoms = 0.0152 -7.2180(0.0136)x + 13.2449(0.0205)y - 0.5265(0.0414)z = 2.8790(0.0318) Angle to previous plane (with approximate e.s.d.) = 83.83 (17) * 0.0104 (0.0028) C11A * -0.0116 (0.0029) C12A * 0.0009 (0.0030) C13A * 0.0109 (0.0030) C14A * -0.0117 (0.0030) C15A * 0.0011 (0.0030) C16A 0.0362 (0.0066) O4A 0.1625 (0.0071) C21A Rms deviation of fitted atoms = 0.0091 8.6489(0.0151)x + 8.6533(0.0366)y + 7.8283(0.0491)z = 9.3268(0.0470) Angle to previous plane (with approximate e.s.d.) = 79.14 (13) * 0.0034 (0.0012) O1A * 0.0044 (0.0015) O2A * -0.0108 (0.0037) C1A * 0.0030 (0.0010) C2A Rms deviation of fitted atoms = 0.0063 6.7591(0.0238)x + 13.8584(0.0319)y + 1.4121(0.0603)z = 3.1825(0.0140) Angle to previous plane (with approximate e.s.d.) = 25.6 (3) * 0.0024 (0.0013) O1B * 0.0031 (0.0017) O2B * -0.0076 (0.0042) C1B * 0.0021 (0.0012) C2B -0.2810 (0.0072) N1B 1.3036 (0.0075) C21B Rms deviation of fitted atoms = 0.0044 1.4887(0.0214)x - 0.3202(0.0391)y + 22.4453(0.0067)z = 6.1190(0.0046) Angle to previous plane(with approximate e.s.d.) = 82.3 (2) * -0.0124 (0.0033) C4B * 0.0105 (0.0035) C5B * -0.0010 (0.0037) C6B * -0.0068 (0.0039) C7B * 0.0051 (0.0039) C8B * 0.0046 (0.0034) C9B -0.1190 (0.0076) C3B -0.2638 (0.0086) O3B -0.0362 (0.0083) C10B -0.0821 (0.0082) N1B Rms deviation of fitted atoms = 0.0078 0.9803(0.0275)x - 0.0431(0.0411)y + 22.5727(0.0057)z = 6.0464(0.0050) Angle to previous plane (with approximate e.s.d.) = 2.87 (8) * 0.0165 (0.0029) N1B * -0.0206 (0.0026) C3B * 0.0167 (0.0028) C4B * -0.0072 (0.0030) C9B * -0.0053 (0.0029) C10B -0.1134 (0.0070) O3B Rms deviation of fitted atoms = 0.0145 -5.2868(0.0164)x + 15.5520(0.0155)y + 0.7517(0.0428)z = 4.1262(0.0182) Angle to previous plane (with approximate e.s.d.) = 89.21 (17) * -0.0056 (0.0030) C11B * 0.0071 (0.0035) C12B * -0.0049 (0.0035) C13B * 0.0011 (0.0032) C14B * 0.0003 (0.0032) C15B * 0.0019 (0.0032) C16B -0.0228 (0.0068) O4B 0.0659 (0.0075) C21B Rms deviation of fitted atoms = 0.0043 6.7591(0.0238)x + 13.8584(0.0319)y + 1.4121(0.0603)z = 3.1825(0.0140) Angle to previous plane (with approximate e.s.d.)= 68.39 (14) * 0.0024 (0.0013) O1B * 0.0031 (0.0017) O2B * -0.0076 (0.0042) C1B * 0.0021 (0.0012) C2B Rms deviation of fitted atoms = 0.0044 -0.7455(0.0359)x + 17.8250(0.0045)y + 0.3055(0.0624)z = 0.4195(0.0411) Angle to previous plane (with approximate e.s.d.) = 43.0 (2) * 0.0026 (0.0014) O1C * 0.0033 (0.0018) O2C * -0.0083 (0.0044) C1C * 0.0024 (0.0013) C2C -0.0398 (0.0083) N1C -1.1407 (0.0079) C21C Rms deviation of fitted atoms = 0.0048 -0.2788(0.0248)x + 1.6305(0.0430)y + 22.5648(0.0056)z = 13.1762(0.0069) Angle to previous plane (with approximate e.s.d.) = 83.9 (2) * -0.0019 (0.0038) C4C * -0.0005 (0.0043) C5C * 0.0031 (0.0049) C6C * -0.0034 (0.0047) C7C * 0.0010 (0.0042) C8C * 0.0016 (0.0040) C9C -0.0014 (0.0081) C3C -0.0022 (0.0095) O3C 0.0470 (0.0091) C10C 0.0046 (0.0084) N1C Rms deviation of fitted atoms = 0.0022 -0.2211(0.0251)x + 1.9304(0.0480)y + 22.5295(0.0070)z = 13.1711(0.0040) Angle to previous plane (with approximate e.s.d.) = 1.01 (7) * -0.0126 (0.0030) N1C * 0.0046 (0.0029) C3C * 0.0060 (0.0033) C4C * -0.0127 (0.0034) C9C * 0.0147 (0.0030) C10C 0.0196 (0.0074) O3C Rms deviation of fitted atoms = 0.0109 -10.3482(0.0057)x - 3.4864(0.0335)y - 4.3493(0.0425)z = 0.4641(0.0196) Angle to previous plane (with approximate e.s.d.) = 78.93 (17) * -0.0054 (0.0031) C11C * 0.0001 (0.0033) C12C * 0.0036 (0.0035) C13C * -0.0021 (0.0036) C14C * -0.0033 (0.0034) C15C * 0.0071 (0.0032) C16C 0.0006 (0.0082) O4C 0.0757 (0.0070) C21C Rms deviation of fitted atoms = 0.0042 -0.7455(0.0359)x + 17.8250(0.0045)y + 0.3055(0.0624)z = 0.4195(0.0411) Angle to previous plane(with approximate e.s.d.) = 82.5 (2) * 0.0026 (0.0014) O1C * 0.0033 (0.0018) O2C * -0.0083 (0.0044) C1C * 0.0024 (0.0013) C2C Rms deviation of fitted atoms = 0.0048 ################################################################# DL-phenylalanine, DL-meta-tyrosine, L & DL-threonine derivatives: A study of the carboxylic acid bond lengths and angles. ################################################################# Molecules A, B and C of compound (I) can be compared with the following: DL-phenylalanine - CF1250 O1—C1 1.314 (2) O2—C1 1.194 (2) O3—C3 1.239 (2) O1—C1—O2 124.00 (18) O1—C1—C2 112.05 (16) O2—C1—C2 123.95 (18) DL-meta-tyrosine - GD1055 O1—C1 1.328 (2) O2—C1 1.196 (2) O3—C3 1.236 (2) O4—C15 1.378 (2) O1—C1—O2 124.3 (2) O1—C1—C2 110.17 (18) O2—C1—C2 125.55 (19) O4—C15—C14 117.2 (2) O4—C15—C16 122.2 (2) L-threonine derivative - BM1380 O1—C1 1.322 (3) O2—C1 1.193 (3) O3—C3 1.232 (3) O4—C11 1.427 (3) O1—C1—O2 124.9 (3) O1—C1—C2 109.7 (2) O2—C1—C2 125.4 (3) O4—C11—C2 110.5 (2) O4—C11—C12 111.9 (2) DL-threonine derivative - BM1380 (geometrical differences) O1—C1 1.2961 (17) <<< O2—C1 1.2210 (18) <<< O3—C3 1.2350 (17) O4—C11 1.4187 (17) O1—C1—O2 124.05 (14) O1—C1—C2 113.29 (12) <<< O2—C1—C2 122.63 (13) <<< O4—C11—C2 105.52 (11) O4—C11—C12 112.15 (13) L-norvaline derivative - GD1085 (disordered carboxylic acid/n-propyl groups) O1A—C1A 1.288 (16) C1A—O2A 1.160 (17) O1B—C1B 1.322 (18) C1B—O2B 1.242 (17) O3—C3 1.243 (3) O1A—C1A—O2A 123.3 (13) O1A—C1A—C2 112.9 (12) O2A—C1A—C2 122.5 (14) O1B—C1B—O2B 120.8 (14) O1B—C1B—C2 113.9 (14) O2B—C1B—C2 124.7 (16) L-valine derivative - GD1085 (molecules A & B) O1A—C1A 1.317 (4) O2A—C1A 1.194 (4) O3A—C3A 1.229 (4) O1A—C1A—O2A 124.2 (3) O1A—C1A—C2A 110.7 (3) O2A—C1A—C2A 125.1 (3) O1B—C1B 1.311 (4) O2B—C1B 1.202 (4) O3B—C3B 1.235 (3) O1B—C1B—O2B 123.1 (3) O1B—C1B—C2B 111.4 (3) O2B—C1B—C2B 125.5 (3) |
x | y | z | Uiso*/Ueq | ||
O1A | −0.0896 (3) | 0.28650 (16) | 0.97414 (15) | 0.0590 (9) | |
O2A | −0.0106 (3) | 0.17910 (18) | 1.00576 (15) | 0.0627 (10) | |
O3A | 0.2947 (2) | 0.19604 (16) | 0.92347 (14) | 0.0484 (8) | |
O4A | 0.1472 (3) | 0.32560 (18) | 0.63561 (15) | 0.0631 (9) | |
N1A | 0.1021 (3) | 0.15017 (18) | 0.90189 (15) | 0.0395 (9) | |
C1A | −0.0238 (4) | 0.2245 (3) | 0.9681 (2) | 0.0455 (12) | |
C2A | 0.0365 (4) | 0.2207 (2) | 0.90756 (19) | 0.0407 (11) | |
C3A | 0.2231 (4) | 0.1424 (2) | 0.9149 (2) | 0.0372 (10) | |
C4A | 0.2515 (4) | 0.0627 (2) | 0.9164 (2) | 0.0446 (11) | |
C5A | 0.3640 (5) | 0.0270 (3) | 0.9256 (2) | 0.0632 (14) | |
C6A | 0.3638 (7) | −0.0494 (4) | 0.9252 (3) | 0.0850 (19) | |
C7A | 0.2564 (8) | −0.0892 (3) | 0.9168 (3) | 0.091 (2) | |
C8A | 0.1440 (7) | −0.0540 (3) | 0.9068 (3) | 0.0809 (18) | |
C9A | 0.1428 (5) | 0.0241 (2) | 0.9069 (2) | 0.0502 (12) | |
C10A | 0.0381 (4) | 0.0781 (2) | 0.8977 (2) | 0.0510 (13) | |
C11A | 0.0080 (4) | 0.2542 (2) | 0.7980 (2) | 0.0408 (11) | |
C12A | 0.1052 (4) | 0.3053 (2) | 0.7926 (2) | 0.0470 (11) | |
C13A | 0.1493 (4) | 0.3282 (2) | 0.7383 (2) | 0.0490 (12) | |
C14A | 0.0992 (4) | 0.2996 (2) | 0.6878 (2) | 0.0472 (11) | |
C15A | 0.0058 (4) | 0.2471 (3) | 0.6914 (2) | 0.0489 (12) | |
C16A | −0.0398 (4) | 0.2254 (2) | 0.7458 (2) | 0.0437 (11) | |
C21A | −0.0520 (4) | 0.2353 (3) | 0.85600 (19) | 0.0503 (12) | |
O1B | −0.1026 (3) | 0.2615 (2) | 0.18076 (16) | 0.0761 (11) | |
O2B | 0.0525 (4) | 0.1887 (2) | 0.15264 (18) | 0.0895 (13) | |
O3B | −0.0604 (3) | 0.04789 (15) | 0.26555 (14) | 0.0487 (8) | |
O4B | 0.0515 (4) | 0.25536 (18) | 0.53753 (15) | 0.0667 (10) | |
N1B | 0.0906 (3) | 0.13819 (17) | 0.26492 (16) | 0.0403 (9) | |
C1B | −0.0103 (5) | 0.2147 (3) | 0.1905 (2) | 0.0527 (13) | |
C2B | 0.0062 (4) | 0.2007 (2) | 0.2559 (2) | 0.0450 (11) | |
C3B | 0.0517 (4) | 0.0663 (2) | 0.26483 (18) | 0.0372 (10) | |
C4B | 0.1614 (4) | 0.0191 (2) | 0.26163 (19) | 0.0396 (10) | |
C5B | 0.1698 (5) | −0.0581 (2) | 0.2610 (2) | 0.0519 (12) | |
C6B | 0.2856 (5) | −0.0890 (3) | 0.2524 (2) | 0.0603 (14) | |
C7B | 0.3897 (5) | −0.0439 (3) | 0.2458 (2) | 0.0616 (14) | |
C8B | 0.3808 (4) | 0.0322 (3) | 0.2480 (2) | 0.0597 (14) | |
C9B | 0.2650 (4) | 0.0639 (3) | 0.2562 (2) | 0.0458 (12) | |
C10B | 0.2253 (4) | 0.1444 (2) | 0.2581 (2) | 0.0524 (13) | |
C11B | 0.0488 (4) | 0.2644 (2) | 0.3540 (2) | 0.0434 (11) | |
C12B | −0.0470 (4) | 0.2312 (3) | 0.3846 (2) | 0.0538 (13) | |
C13B | −0.0474 (5) | 0.2274 (3) | 0.4451 (2) | 0.0564 (13) | |
C14B | 0.0478 (4) | 0.2586 (2) | 0.4766 (2) | 0.0454 (11) | |
C15B | 0.1445 (5) | 0.2928 (2) | 0.4480 (2) | 0.0501 (12) | |
C16B | 0.1435 (4) | 0.2955 (2) | 0.3870 (2) | 0.0477 (12) | |
C21B | 0.0468 (5) | 0.2716 (2) | 0.2877 (2) | 0.0538 (13) | |
O1C | −0.3651 (3) | −0.0029 (3) | 0.65872 (17) | 0.0956 (15) | |
O2C | −0.1767 (3) | 0.0045 (3) | 0.69273 (17) | 0.0879 (13) | |
O3C | −0.0623 (3) | 0.13484 (15) | 0.57332 (15) | 0.0518 (8) | |
O4C | −0.1461 (5) | −0.08855 (19) | 0.31170 (18) | 0.0897 (13) | |
N1C | −0.0737 (3) | 0.00823 (17) | 0.58263 (17) | 0.0424 (8) | |
C1C | −0.2450 (4) | 0.0016 (3) | 0.6524 (2) | 0.0451 (11) | |
C2C | −0.2078 (3) | 0.0049 (2) | 0.5888 (2) | 0.0412 (10) | |
C3C | −0.0112 (4) | 0.0730 (2) | 0.5785 (2) | 0.0396 (10) | |
C4C | 0.1223 (4) | 0.0541 (2) | 0.5814 (2) | 0.0419 (10) | |
C5C | 0.2260 (4) | 0.1003 (3) | 0.5795 (3) | 0.0634 (15) | |
C6C | 0.3410 (5) | 0.0666 (4) | 0.5835 (3) | 0.0818 (18) | |
C7C | 0.3524 (4) | −0.0096 (3) | 0.5888 (3) | 0.0745 (17) | |
C8C | 0.2495 (4) | −0.0553 (3) | 0.5910 (3) | 0.0655 (16) | |
C9C | 0.1345 (4) | −0.0219 (2) | 0.5872 (2) | 0.0473 (11) | |
C10C | 0.0067 (4) | −0.0566 (2) | 0.5902 (3) | 0.0534 (13) | |
C11C | −0.2282 (4) | −0.0650 (2) | 0.4895 (2) | 0.0455 (12) | |
C12C | −0.2335 (4) | −0.0041 (3) | 0.4522 (2) | 0.0536 (13) | |
C13C | −0.2069 (5) | −0.0105 (3) | 0.3933 (2) | 0.0565 (13) | |
C14C | −0.1736 (5) | −0.0789 (3) | 0.3702 (2) | 0.0598 (14) | |
C15C | −0.1684 (4) | −0.1402 (3) | 0.4071 (3) | 0.0577 (14) | |
C16C | −0.1960 (4) | −0.1329 (2) | 0.4646 (2) | 0.0505 (12) | |
C21C | −0.2641 (4) | −0.0610 (3) | 0.5532 (2) | 0.0539 (13) | |
H1A | −0.1264 | 0.2856 | 1.0058 | 0.071* | |
H4A | 0.1213 | 0.2999 | 0.6083 | 0.076* | |
H2A | 0.0996 | 0.2602 | 0.9064 | 0.049* | |
H5A | 0.4368 | 0.0539 | 0.9317 | 0.076* | |
H6A | 0.4381 | −0.0750 | 0.9309 | 0.102* | |
H7A | 0.2592 | −0.1412 | 0.9178 | 0.109* | |
H8A | 0.0718 | −0.0813 | 0.9002 | 0.097* | |
H10A | −0.0002 | 0.0714 | 0.8594 | 0.061* | |
H10B | −0.0247 | 0.0729 | 0.9282 | 0.061* | |
H12A | 0.1414 | 0.3246 | 0.8266 | 0.056* | |
H13A | 0.2133 | 0.3631 | 0.7361 | 0.059* | |
H15A | −0.0267 | 0.2262 | 0.6572 | 0.059* | |
H16A | −0.1040 | 0.1906 | 0.7475 | 0.052* | |
H21A | −0.1033 | 0.1912 | 0.8505 | 0.060* | |
H21B | −0.1069 | 0.2762 | 0.8668 | 0.060* | |
H1B | −0.1022 | 0.2743 | 0.1460 | 0.091* | |
H4B | −0.0038 | 0.2276 | 0.5494 | 0.080* | |
H2B | −0.0749 | 0.1862 | 0.2718 | 0.054* | |
H5B | 0.0999 | −0.0880 | 0.2662 | 0.062* | |
H6B | 0.2942 | −0.1408 | 0.2509 | 0.072* | |
H7B | 0.4670 | −0.0660 | 0.2399 | 0.074* | |
H8B | 0.4511 | 0.0620 | 0.2442 | 0.072* | |
H10C | 0.2625 | 0.1703 | 0.2913 | 0.063* | |
H10D | 0.2470 | 0.1702 | 0.2219 | 0.063* | |
H12B | −0.1132 | 0.2108 | 0.3637 | 0.065* | |
H13B | −0.1124 | 0.2036 | 0.4646 | 0.068* | |
H15B | 0.2097 | 0.3139 | 0.4692 | 0.060* | |
H16B | 0.2088 | 0.3191 | 0.3676 | 0.057* | |
H21C | 0.1294 | 0.2851 | 0.2742 | 0.065* | |
H21D | −0.0091 | 0.3119 | 0.2769 | 0.065* | |
H1C | −0.3812 | −0.0272 | 0.6884 | 0.115* | |
H4C | −0.1288 | −0.0480 | 0.2969 | 0.108* | |
H2C | −0.2418 | 0.0513 | 0.5723 | 0.049* | |
H5C | 0.2182 | 0.1519 | 0.5756 | 0.076* | |
H6C | 0.4123 | 0.0961 | 0.5825 | 0.098* | |
H7C | 0.4313 | −0.0307 | 0.5910 | 0.089* | |
H8C | 0.2574 | −0.1068 | 0.5950 | 0.079* | |
H10E | −0.0054 | −0.0928 | 0.5588 | 0.064* | |
H10F | −0.0074 | −0.0807 | 0.6279 | 0.064* | |
H12C | −0.2557 | 0.0424 | 0.4674 | 0.064* | |
H13C | −0.2114 | 0.0313 | 0.3689 | 0.068* | |
H15C | −0.1457 | −0.1867 | 0.3921 | 0.069* | |
H16C | −0.1934 | −0.1751 | 0.4886 | 0.061* | |
H21E | −0.2396 | −0.1074 | 0.5721 | 0.065* | |
H21F | −0.3540 | −0.0577 | 0.5556 | 0.065* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.078 (2) | 0.0446 (17) | 0.055 (2) | 0.0079 (17) | 0.0261 (19) | −0.0007 (16) |
O2A | 0.082 (2) | 0.058 (2) | 0.048 (2) | 0.0111 (18) | 0.0092 (19) | 0.0074 (18) |
O3A | 0.0398 (16) | 0.0569 (18) | 0.048 (2) | −0.0093 (15) | −0.0046 (15) | −0.0004 (16) |
O4A | 0.067 (2) | 0.071 (2) | 0.051 (2) | −0.0084 (19) | 0.007 (2) | −0.0014 (18) |
N1A | 0.0364 (18) | 0.0381 (19) | 0.044 (2) | −0.0041 (16) | 0.0001 (16) | −0.0048 (16) |
C1A | 0.047 (3) | 0.039 (3) | 0.050 (3) | −0.002 (2) | 0.000 (2) | −0.009 (2) |
C2A | 0.039 (2) | 0.039 (2) | 0.044 (3) | −0.0004 (18) | 0.005 (2) | −0.006 (2) |
C3A | 0.037 (2) | 0.042 (2) | 0.032 (3) | −0.002 (2) | −0.004 (2) | 0.000 (2) |
C4A | 0.051 (3) | 0.051 (3) | 0.032 (3) | 0.008 (2) | 0.006 (2) | −0.005 (2) |
C5A | 0.067 (3) | 0.071 (3) | 0.051 (3) | 0.026 (3) | −0.004 (3) | 0.001 (3) |
C6A | 0.112 (5) | 0.082 (4) | 0.061 (4) | 0.044 (4) | −0.010 (4) | −0.006 (3) |
C7A | 0.152 (7) | 0.042 (3) | 0.078 (5) | 0.025 (4) | −0.012 (5) | −0.007 (3) |
C8A | 0.113 (5) | 0.043 (3) | 0.087 (5) | −0.005 (3) | 0.003 (4) | −0.008 (3) |
C9A | 0.068 (3) | 0.042 (3) | 0.040 (3) | 0.000 (2) | 0.007 (2) | −0.008 (2) |
C10A | 0.045 (3) | 0.046 (2) | 0.062 (3) | −0.008 (2) | 0.004 (2) | −0.010 (2) |
C11A | 0.033 (2) | 0.044 (2) | 0.045 (3) | 0.013 (2) | −0.001 (2) | 0.000 (2) |
C12A | 0.048 (3) | 0.047 (3) | 0.046 (3) | 0.004 (2) | −0.003 (2) | −0.008 (2) |
C13A | 0.044 (2) | 0.049 (3) | 0.054 (3) | −0.004 (2) | 0.004 (2) | −0.011 (2) |
C14A | 0.043 (3) | 0.047 (2) | 0.051 (3) | 0.003 (2) | 0.004 (2) | −0.004 (2) |
C15A | 0.046 (3) | 0.056 (3) | 0.045 (3) | 0.005 (2) | −0.004 (2) | −0.012 (2) |
C16A | 0.036 (2) | 0.044 (2) | 0.051 (3) | 0.0007 (19) | 0.000 (2) | 0.002 (2) |
C21A | 0.041 (2) | 0.059 (3) | 0.051 (3) | 0.010 (2) | −0.001 (2) | −0.005 (2) |
O1B | 0.075 (2) | 0.096 (3) | 0.057 (2) | 0.027 (2) | −0.005 (2) | 0.018 (2) |
O2B | 0.120 (3) | 0.090 (3) | 0.059 (3) | 0.050 (3) | −0.003 (3) | 0.000 (2) |
O3B | 0.0361 (16) | 0.0498 (17) | 0.060 (2) | −0.0088 (14) | −0.0008 (15) | 0.0030 (16) |
O4B | 0.093 (3) | 0.056 (2) | 0.051 (2) | −0.024 (2) | −0.005 (2) | 0.0077 (17) |
N1B | 0.0370 (18) | 0.0356 (19) | 0.048 (2) | −0.0037 (16) | −0.0065 (17) | 0.0085 (17) |
C1B | 0.057 (3) | 0.044 (3) | 0.057 (4) | 0.013 (2) | −0.004 (3) | 0.008 (2) |
C2B | 0.049 (2) | 0.040 (2) | 0.046 (3) | 0.005 (2) | −0.002 (2) | 0.006 (2) |
C3B | 0.039 (2) | 0.035 (2) | 0.037 (3) | −0.005 (2) | −0.004 (2) | 0.004 (2) |
C4B | 0.041 (2) | 0.042 (2) | 0.036 (3) | −0.001 (2) | −0.001 (2) | 0.003 (2) |
C5B | 0.056 (3) | 0.038 (2) | 0.062 (3) | −0.003 (2) | −0.001 (3) | −0.005 (2) |
C6B | 0.066 (3) | 0.048 (3) | 0.067 (4) | 0.010 (3) | 0.011 (3) | 0.000 (3) |
C7B | 0.051 (3) | 0.072 (3) | 0.061 (4) | 0.018 (3) | 0.009 (3) | 0.001 (3) |
C8B | 0.039 (3) | 0.070 (3) | 0.070 (4) | −0.004 (2) | 0.008 (3) | 0.013 (3) |
C9B | 0.041 (2) | 0.048 (3) | 0.049 (3) | −0.004 (2) | 0.000 (2) | 0.009 (2) |
C10B | 0.045 (3) | 0.046 (3) | 0.066 (4) | −0.012 (2) | −0.004 (2) | 0.010 (3) |
C11B | 0.049 (3) | 0.034 (2) | 0.047 (3) | 0.002 (2) | 0.002 (2) | 0.009 (2) |
C12B | 0.046 (3) | 0.058 (3) | 0.057 (3) | −0.009 (2) | −0.007 (3) | −0.007 (3) |
C13B | 0.047 (3) | 0.066 (3) | 0.056 (4) | −0.010 (3) | 0.002 (3) | 0.003 (3) |
C14B | 0.056 (3) | 0.039 (2) | 0.041 (3) | −0.001 (2) | −0.004 (2) | 0.004 (2) |
C15B | 0.054 (3) | 0.041 (2) | 0.055 (3) | −0.012 (2) | −0.014 (3) | 0.006 (2) |
C16B | 0.044 (3) | 0.038 (2) | 0.061 (3) | −0.004 (2) | 0.003 (2) | 0.009 (2) |
C21B | 0.069 (3) | 0.040 (3) | 0.052 (3) | 0.002 (2) | 0.002 (3) | 0.008 (2) |
O1C | 0.0411 (19) | 0.186 (5) | 0.059 (3) | −0.029 (3) | 0.0045 (17) | 0.002 (3) |
O2C | 0.051 (2) | 0.153 (4) | 0.060 (3) | −0.021 (3) | −0.011 (2) | −0.002 (3) |
O3C | 0.0435 (16) | 0.0371 (16) | 0.075 (2) | 0.0001 (14) | 0.0012 (17) | 0.0066 (16) |
O4C | 0.137 (4) | 0.063 (2) | 0.069 (3) | −0.005 (3) | 0.041 (3) | −0.001 (2) |
N1C | 0.0299 (17) | 0.0351 (18) | 0.062 (2) | −0.0006 (15) | −0.0020 (18) | −0.0008 (19) |
C1C | 0.033 (2) | 0.049 (3) | 0.053 (3) | −0.009 (2) | −0.003 (2) | −0.002 (2) |
C2C | 0.0257 (19) | 0.050 (2) | 0.048 (3) | −0.0048 (18) | −0.002 (2) | 0.008 (2) |
C3C | 0.040 (2) | 0.041 (2) | 0.037 (3) | −0.005 (2) | −0.003 (2) | 0.003 (2) |
C4C | 0.034 (2) | 0.055 (3) | 0.036 (3) | −0.007 (2) | 0.000 (2) | 0.002 (2) |
C5C | 0.038 (3) | 0.065 (3) | 0.087 (4) | −0.013 (2) | 0.003 (3) | −0.001 (3) |
C6C | 0.036 (3) | 0.097 (4) | 0.112 (5) | −0.020 (3) | −0.007 (3) | 0.010 (4) |
C7C | 0.027 (2) | 0.102 (4) | 0.095 (5) | 0.007 (3) | −0.003 (3) | 0.016 (4) |
C8C | 0.042 (3) | 0.071 (3) | 0.083 (4) | 0.014 (3) | 0.000 (3) | 0.015 (3) |
C9C | 0.039 (2) | 0.049 (3) | 0.054 (3) | −0.002 (2) | 0.002 (2) | 0.003 (2) |
C10C | 0.038 (2) | 0.045 (2) | 0.078 (4) | 0.000 (2) | −0.001 (3) | 0.005 (3) |
C11C | 0.033 (2) | 0.047 (3) | 0.057 (3) | −0.005 (2) | 0.003 (2) | 0.004 (2) |
C12C | 0.052 (3) | 0.043 (3) | 0.066 (4) | −0.005 (2) | 0.008 (2) | −0.003 (3) |
C13C | 0.074 (3) | 0.044 (3) | 0.051 (3) | 0.000 (3) | 0.017 (3) | 0.008 (2) |
C14C | 0.056 (3) | 0.056 (3) | 0.067 (4) | −0.007 (3) | 0.019 (3) | −0.007 (3) |
C15C | 0.051 (3) | 0.041 (3) | 0.081 (5) | −0.004 (2) | 0.012 (3) | −0.002 (3) |
C16C | 0.046 (3) | 0.044 (3) | 0.062 (4) | −0.006 (2) | 0.002 (2) | 0.004 (2) |
C21C | 0.038 (2) | 0.059 (3) | 0.065 (4) | −0.016 (2) | −0.002 (2) | 0.010 (3) |
O1A—C1A | 1.321 (5) | C5B—C6B | 1.377 (7) |
O2A—C1A | 1.187 (5) | C6B—C7B | 1.388 (7) |
O3A—C3A | 1.245 (5) | C7B—C8B | 1.364 (7) |
O4A—C14A | 1.372 (5) | C8B—C9B | 1.381 (6) |
N1A—C2A | 1.450 (5) | C9B—C10B | 1.501 (6) |
N1A—C3A | 1.343 (5) | C11B—C12B | 1.377 (6) |
N1A—C10A | 1.464 (5) | C11B—C16B | 1.380 (6) |
C1A—C2A | 1.519 (6) | C11B—C21B | 1.509 (6) |
C2A—C21A | 1.530 (6) | C12B—C13B | 1.373 (6) |
C3A—C4A | 1.457 (6) | C13B—C14B | 1.369 (7) |
C4A—C5A | 1.384 (6) | C14B—C15B | 1.370 (6) |
C4A—C9A | 1.375 (6) | C15B—C16B | 1.383 (6) |
C5A—C6A | 1.365 (8) | O1C—C1C | 1.303 (5) |
C6A—C7A | 1.369 (9) | O2C—C1C | 1.174 (5) |
C7A—C8A | 1.382 (9) | O3C—C3C | 1.239 (5) |
C8A—C9A | 1.395 (7) | O4C—C14C | 1.370 (6) |
C9A—C10A | 1.497 (7) | N1C—C2C | 1.451 (5) |
C11A—C12A | 1.394 (6) | N1C—C3C | 1.342 (5) |
C11A—C16A | 1.388 (6) | N1C—C10C | 1.456 (5) |
C11A—C21A | 1.503 (6) | C1C—C2C | 1.498 (6) |
C12A—C13A | 1.381 (6) | C2C—C21C | 1.549 (6) |
C13A—C14A | 1.366 (6) | C3C—C4C | 1.477 (6) |
C14A—C15A | 1.376 (6) | C4C—C5C | 1.389 (6) |
C15A—C16A | 1.383 (6) | C4C—C9C | 1.371 (6) |
O1B—C1B | 1.316 (5) | C5C—C6C | 1.379 (7) |
O2B—C1B | 1.187 (6) | C6C—C7C | 1.372 (8) |
O3B—C3B | 1.250 (5) | C7C—C8C | 1.377 (7) |
O4B—C14B | 1.382 (5) | C8C—C9C | 1.376 (6) |
N1B—C2B | 1.454 (5) | C9C—C10C | 1.510 (6) |
N1B—C3B | 1.352 (5) | C11C—C12C | 1.379 (6) |
N1B—C10B | 1.462 (5) | C11C—C16C | 1.382 (6) |
C1B—C2B | 1.514 (7) | C11C—C21C | 1.498 (7) |
C2B—C21B | 1.521 (6) | C12C—C13C | 1.370 (7) |
C3B—C4B | 1.453 (6) | C13C—C14C | 1.377 (7) |
C4B—C5B | 1.382 (6) | C14C—C15C | 1.378 (7) |
C4B—C9B | 1.377 (6) | C15C—C16C | 1.344 (7) |
C2A—N1A—C3A | 122.9 (3) | C6B—C7B—C8B | 121.2 (5) |
C2A—N1A—C10A | 122.8 (3) | C7B—C8B—C9B | 118.5 (5) |
C3A—N1A—C10A | 112.3 (3) | C4B—C9B—C8B | 120.2 (4) |
O1A—C1A—O2A | 124.2 (5) | C4B—C9B—C10B | 108.9 (4) |
O1A—C1A—C2A | 111.1 (4) | C8B—C9B—C10B | 130.8 (4) |
O2A—C1A—C2A | 124.6 (4) | N1B—C10B—C9B | 102.3 (3) |
N1A—C2A—C1A | 109.1 (4) | O4B—C14B—C13B | 121.7 (5) |
N1A—C2A—C21A | 112.6 (3) | O4B—C14B—C15B | 118.1 (4) |
C1A—C2A—C21A | 114.6 (3) | C13B—C14B—C15B | 120.2 (5) |
O3A—C3A—N1A | 123.7 (4) | C12B—C11B—C16B | 117.0 (4) |
O3A—C3A—C4A | 128.3 (4) | C12B—C11B—C21B | 121.8 (4) |
N1A—C3A—C4A | 108.0 (4) | C16B—C11B—C21B | 121.1 (4) |
C3A—C4A—C5A | 129.6 (4) | C11B—C12B—C13B | 121.8 (5) |
C3A—C4A—C9A | 108.0 (4) | C12B—C13B—C14B | 119.9 (5) |
C5A—C4A—C9A | 122.4 (4) | C14B—C15B—C16B | 118.9 (5) |
C4A—C5A—C6A | 117.3 (6) | C11B—C16B—C15B | 122.2 (5) |
C5A—C6A—C7A | 121.4 (6) | C11B—C21B—C2B | 114.0 (4) |
C6A—C7A—C8A | 121.7 (5) | C2C—N1C—C3C | 122.7 (3) |
C7A—C8A—C9A | 117.6 (6) | C3C—N1C—C10C | 113.4 (3) |
C4A—C9A—C8A | 119.6 (5) | C2C—N1C—C10C | 123.1 (3) |
C4A—C9A—C10A | 109.8 (4) | O1C—C1C—O2C | 122.6 (5) |
C8A—C9A—C10A | 130.6 (5) | O1C—C1C—C2C | 111.9 (4) |
N1A—C10A—C9A | 101.8 (3) | O2C—C1C—C2C | 125.6 (4) |
O4A—C14A—C13A | 116.5 (4) | N1C—C2C—C1C | 111.0 (4) |
O4A—C14A—C15A | 123.9 (4) | N1C—C2C—C21C | 111.7 (4) |
C13A—C14A—C15A | 119.6 (5) | C1C—C2C—C21C | 111.5 (4) |
C12A—C11A—C16A | 116.5 (4) | O3C—C3C—N1C | 123.6 (4) |
C12A—C11A—C21A | 123.1 (4) | O3C—C3C—C4C | 129.8 (4) |
C16A—C11A—C21A | 120.2 (4) | N1C—C3C—C4C | 106.6 (3) |
C11A—C12A—C13A | 122.0 (4) | C3C—C4C—C5C | 130.1 (4) |
C12A—C13A—C14A | 120.1 (4) | C3C—C4C—C9C | 108.9 (4) |
C14A—C15A—C16A | 120.3 (4) | C5C—C4C—C9C | 121.0 (4) |
C11A—C16A—C15A | 121.6 (4) | C4C—C5C—C6C | 117.4 (5) |
C2A—C21A—C11A | 116.0 (4) | C5C—C6C—C7C | 121.3 (5) |
C2B—N1B—C3B | 122.5 (3) | C6C—C7C—C8C | 121.3 (5) |
C2B—N1B—C10B | 123.1 (3) | C7C—C8C—C9C | 117.6 (5) |
C3B—N1B—C10B | 112.2 (3) | C4C—C9C—C8C | 121.4 (4) |
O1B—C1B—O2B | 123.9 (5) | C4C—C9C—C10C | 108.9 (4) |
O1B—C1B—C2B | 110.9 (5) | C8C—C9C—C10C | 129.6 (4) |
O2B—C1B—C2B | 125.1 (5) | N1C—C10C—C9C | 102.1 (3) |
N1B—C2B—C1B | 109.8 (4) | O4C—C14C—C13C | 122.4 (5) |
N1B—C2B—C21B | 113.2 (4) | O4C—C14C—C15C | 118.6 (5) |
C1B—C2B—C21B | 111.1 (4) | C13C—C14C—C15C | 119.0 (5) |
O3B—C3B—N1B | 123.2 (4) | C12C—C11C—C16C | 117.0 (5) |
O3B—C3B—C4B | 129.3 (4) | C12C—C11C—C21C | 122.9 (4) |
N1B—C3B—C4B | 107.5 (3) | C16C—C11C—C21C | 120.0 (4) |
C3B—C4B—C5B | 129.2 (4) | C11C—C12C—C13C | 121.5 (5) |
C3B—C4B—C9B | 109.0 (3) | C12C—C13C—C14C | 120.0 (5) |
C5B—C4B—C9B | 121.7 (4) | C14C—C15C—C16C | 120.2 (5) |
C4B—C5B—C6B | 117.5 (5) | C15C—C16C—C11C | 122.4 (5) |
C5B—C6B—C7B | 120.8 (4) | C11C—C21C—C2C | 115.9 (4) |
C3A—N1A—C2A—C1A | −93.0 (5) | C5B—C4B—C9B—C10B | 179.7 (4) |
C10A—N1A—C2A—C1A | 69.4 (5) | C3B—C4B—C9B—C10B | 2.3 (5) |
C3A—N1A—C2A—C21A | 138.5 (4) | C7B—C8B—C9B—C4B | −0.2 (8) |
C10A—N1A—C2A—C21A | −59.0 (5) | C7B—C8B—C9B—C10B | −177.4 (5) |
O2A—C1A—C2A—N1A | 5.1 (6) | C3B—N1B—C10B—C9B | −2.2 (5) |
O1A—C1A—C2A—N1A | −177.0 (3) | C2B—N1B—C10B—C9B | −165.8 (4) |
O1A—C1A—C2A—C21A | −49.8 (5) | C4B—C9B—C10B—N1B | −0.2 (5) |
O2A—C1A—C2A—C21A | 132.3 (5) | C8B—C9B—C10B—N1B | 177.2 (5) |
C2A—N1A—C3A—O3A | −12.3 (7) | C16B—C11B—C12B—C13B | −1.5 (7) |
C10A—N1A—C3A—O3A | −176.4 (4) | C21B—C11B—C12B—C13B | −177.4 (4) |
C2A—N1A—C3A—C4A | 168.1 (4) | C11B—C12B—C13B—C14B | 1.5 (8) |
C10A—N1A—C3A—C4A | 4.0 (5) | C12B—C13B—C14B—C15B | −0.9 (7) |
O3A—C3A—C4A—C9A | 177.4 (5) | C12B—C13B—C14B—O4B | −179.4 (4) |
N1A—C3A—C4A—C9A | −3.1 (6) | C13B—C14B—C15B—C16B | 0.4 (7) |
O3A—C3A—C4A—C5A | −2.3 (9) | O4B—C14B—C15B—C16B | 179.0 (4) |
N1A—C3A—C4A—C5A | 177.3 (5) | C12B—C11B—C16B—C15B | 1.0 (7) |
C9A—C4A—C5A—C6A | −0.3 (8) | C21B—C11B—C16B—C15B | 176.9 (4) |
C3A—C4A—C5A—C6A | 179.3 (5) | C14B—C15B—C16B—C11B | −0.5 (7) |
C4A—C5A—C6A—C7A | −0.7 (10) | C12B—C11B—C21B—C2B | −44.9 (6) |
C5A—C6A—C7A—C8A | 1.6 (11) | C16B—C11B—C21B—C2B | 139.4 (4) |
C6A—C7A—C8A—C9A | −1.4 (11) | N1B—C2B—C21B—C11B | −63.6 (6) |
C5A—C4A—C9A—C8A | 0.4 (8) | C1B—C2B—C21B—C11B | 172.4 (4) |
C3A—C4A—C9A—C8A | −179.3 (4) | C3C—N1C—C2C—C1C | −93.0 (5) |
C5A—C4A—C9A—C10A | −179.3 (5) | C10C—N1C—C2C—C1C | 76.5 (5) |
C3A—C4A—C9A—C10A | 1.0 (5) | C3C—N1C—C2C—C21C | 141.8 (4) |
C7A—C8A—C9A—C4A | 0.4 (9) | C10C—N1C—C2C—C21C | −48.6 (6) |
C7A—C8A—C9A—C10A | −179.9 (6) | O2C—C1C—C2C—N1C | 2.9 (7) |
C3A—N1A—C10A—C9A | −3.3 (5) | O1C—C1C—C2C—N1C | −178.7 (4) |
C2A—N1A—C10A—C9A | −167.4 (4) | O1C—C1C—C2C—C21C | −53.4 (6) |
C4A—C9A—C10A—N1A | 1.3 (5) | O2C—C1C—C2C—C21C | 128.3 (6) |
C8A—C9A—C10A—N1A | −178.4 (5) | C2C—N1C—C3C—O3C | −7.7 (7) |
C16A—C11A—C12A—C13A | 2.1 (6) | C10C—N1C—C3C—O3C | −178.2 (5) |
C21A—C11A—C12A—C13A | −172.5 (4) | C2C—N1C—C3C—C4C | 172.1 (4) |
C11A—C12A—C13A—C14A | −1.2 (6) | C10C—N1C—C3C—C4C | 1.7 (5) |
C12A—C13A—C14A—O4A | 179.4 (4) | O3C—C3C—C4C—C9C | 179.9 (5) |
C12A—C13A—C14A—C15A | −1.0 (6) | N1C—C3C—C4C—C9C | 0.1 (6) |
C13A—C14A—C15A—C16A | 2.2 (6) | O3C—C3C—C4C—C5C | 0.2 (9) |
O4A—C14A—C15A—C16A | −178.2 (4) | N1C—C3C—C4C—C5C | −179.6 (5) |
C14A—C15A—C16A—C11A | −1.3 (6) | C9C—C4C—C5C—C6C | 0.1 (9) |
C12A—C11A—C16A—C15A | −0.8 (6) | C3C—C4C—C5C—C6C | 179.8 (6) |
C21A—C11A—C16A—C15A | 173.9 (4) | C4C—C5C—C6C—C7C | 0.4 (10) |
C16A—C11A—C21A—C2A | 140.2 (4) | C5C—C6C—C7C—C8C | −0.7 (11) |
C12A—C11A—C21A—C2A | −45.4 (6) | C6C—C7C—C8C—C9C | 0.5 (10) |
N1A—C2A—C21A—C11A | −71.7 (5) | C5C—C4C—C9C—C8C | −0.3 (9) |
C1A—C2A—C21A—C11A | 162.8 (4) | C3C—C4C—C9C—C8C | 179.9 (5) |
C3B—N1B—C2B—C1B | −85.5 (5) | C5C—C4C—C9C—C10C | 178.1 (5) |
C10B—N1B—C2B—C1B | 76.5 (5) | C3C—C4C—C9C—C10C | −1.7 (6) |
C3B—N1B—C2B—C21B | 149.7 (4) | C7C—C8C—C9C—C4C | 0.0 (9) |
C10B—N1B—C2B—C21B | −48.3 (6) | C7C—C8C—C9C—C10C | −178.0 (6) |
O2B—C1B—C2B—N1B | −13.0 (7) | C3C—N1C—C10C—C9C | −2.6 (5) |
O1B—C1B—C2B—N1B | 168.5 (4) | C2C—N1C—C10C—C9C | −173.0 (4) |
O1B—C1B—C2B—C21B | −65.5 (5) | C4C—C9C—C10C—N1C | 2.5 (6) |
O2B—C1B—C2B—C21B | 113.0 (6) | C8C—C9C—C10C—N1C | −179.3 (6) |
C2B—N1B—C3B—O3B | −10.6 (7) | C16C—C11C—C12C—C13C | −0.7 (7) |
C10B—N1B—C3B—O3B | −174.4 (4) | C21C—C11C—C12C—C13C | −176.1 (4) |
C2B—N1B—C3B—C4B | 167.3 (4) | C11C—C12C—C13C—C14C | −0.2 (8) |
C10B—N1B—C3B—C4B | 3.6 (5) | C12C—C13C—C14C—O4C | −180.0 (5) |
O3B—C3B—C4B—C9B | 174.1 (5) | C12C—C13C—C14C—C15C | 0.4 (8) |
N1B—C3B—C4B—C9B | −3.7 (5) | O4C—C14C—C15C—C16C | −179.4 (5) |
O3B—C3B—C4B—C5B | −2.9 (8) | C13C—C14C—C15C—C16C | 0.3 (8) |
N1B—C3B—C4B—C5B | 179.2 (5) | C14C—C15C—C16C—C11C | −1.2 (7) |
C9B—C4B—C5B—C6B | −2.5 (7) | C12C—C11C—C16C—C15C | 1.4 (7) |
C3B—C4B—C5B—C6B | 174.3 (5) | C21C—C11C—C16C—C15C | 177.0 (4) |
C4B—C5B—C6B—C7B | 1.3 (8) | C12C—C11C—C21C—C2C | −48.4 (6) |
C5B—C6B—C7B—C8B | 0.3 (9) | C16C—C11C—C21C—C2C | 136.3 (4) |
C6B—C7B—C8B—C9B | −0.9 (9) | N1C—C2C—C21C—C11C | −52.5 (5) |
C5B—C4B—C9B—C8B | 1.9 (7) | C1C—C2C—C21C—C11C | −177.4 (4) |
C3B—C4B—C9B—C8B | −175.4 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···O3Ai | 0.82 | 1.84 | 2.652 (4) | 169 |
O1B—H1B···O3Aii | 0.82 | 2.00 | 2.716 (5) | 147 |
O1C—H1C···O3Biii | 0.82 | 1.89 | 2.675 (5) | 159 |
O4A—H4A···O4B | 0.82 | 1.94 | 2.753 (5) | 170 |
O4B—H4B···O3C | 0.82 | 1.85 | 2.607 (4) | 152 |
O4C—H4C···O3B | 0.82 | 2.00 | 2.809 (4) | 171 |
C10C—H10E···O1Aiv | 0.97 | 2.50 | 3.284 (5) | 138 |
C15A—H15A···O3C | 0.93 | 2.54 | 3.425 (6) | 160 |
C12B—H12B···O4Aii | 0.93 | 2.66 | 3.473 (5) | 147 |
C15C—H15C···O2Bv | 0.93 | 2.65 | 3.569 (7) | 173 |
C5A—H5A···Cg1vi | 0.93 | 2.86 | 3.716 (5) | 153 |
Symmetry codes: (i) x−1/2, −y+1/2, −z+2; (ii) x−1/2, −y+1/2, −z+1; (iii) −x−1/2, −y, z+1/2; (iv) −x, y−1/2, −z+3/2; (v) −x, y−1/2, −z+1/2; (vi) −x+1/2, −y, z+1/2. |