Intermolecular O-H...O hydrogen bonding in the three independent molecules of (2S)-3-(4-hydroxyphenyl)-2-(1-oxoisoindolin-2-yl)­propanoic acid

The title compound, C₁₇H₁₅NO₄, derived from L-tyrosine, crystallizes with three independent mol­ecules which differ in the conformation of the asymmetric unit: the N-C-C-C_ipso torsion angles are -71.7 (5), -63.6 (6) and -52.5 (5)°, respectively. Deformations in the phenol ring hydroxy O-C-C angles of 116.5 (4)/123.9 (4), 121.7 (5)/118.1 (4) and 122.4 (5)/118.6 (5)°, respectively, result from their respective intermolecular hydrogen-bonding environments. Intermolecular O_acid-H...O=C_indole, O_phenol-H...O-H_phenol and O_phenol-H...O=C_indole hydrogen bonds, with O...O distances in the range 2.607 (4)-2.809 (4) Å, are present in combination with C-H...O and C-H...[pi]_arene interactions. The primary hydrogen-bonding systems assemble with graph sets R₃³(8) and R₃²(22).

Computing details

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).

(2S)-3-(4-hydroxyphenyl)-2-(1-oxoisoindolin-2-yl)propanoic acidd

Crystal data

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) Å^3	T = 294 K
Z = 12	Block, colourless
F(000) = 1872	0.36 × 0.36 × 0.28 mm

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.063P)^2] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0013 (3)

Special details

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 U_iso(H) = 1.5U_eq(C) for methyl H atoms and 1.2U_eq(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 U_iso(H) = 1.5U_eq(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)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O3A^i	0.82	1.84	2.652 (4)	169
O1B—H1B···O3A^ii	0.82	2.00	2.716 (5)	147
O1C—H1C···O3B^iii	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···O1A^iv	0.97	2.50	3.284 (5)	138
C15A—H15A···O3C	0.93	2.54	3.425 (6)	160
C12B—H12B···O4A^ii	0.93	2.66	3.473 (5)	147
C15C—H15C···O2B^v	0.93	2.65	3.569 (7)	173
C5A—H5A···Cg1^vi	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.