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4-Methylhippuric acid {systematic name: 2-[(4-methylbenzoyl)amino]ethanoic acid}, a
p-xylene excreted metabolite with a backbone containing three rotatable bonds (R-bonds), is likely to produce more than one stable molecular structure in the solid state. In this work, we prepared polymorph
I by slow solvent evaporation (plates with
Z′ = 1) and polymorph
II by mechanical grinding (plates with
Z′ = 2). Potential energy surface (PES) analysis, rotating the molecule about the C—C—N—C torsion angle, shows four conformational energy basins. The second basin, with torsion angles near −73°, agree with the conformations adopted by polymorph
I and molecules
A of polymorph
II, and the third basin at 57° matched molecules
B of polymorph
II. The energy barrier between these basins is 27.5 kJ mol
−1. Superposition of the molecules of polymorphs
I and
II rendered a maximum r.m.s. deviation of 0.398 Å. Polymorphs
I and
II are therefore true conformational polymorphs. The crystal packing of polymorph
I consists of
C(5) chains linked by N—H
O interactions along the
a axis and
C(7) chains linked by O—H
O interactions along the
b axis. In polymorph
II, two molecules (
A with
A or
B with
B) are connected by two acid–amide O—H
O interactions rendering
R22(14) centrosymmetric dimers. These dimers alternate to pile up along the
b axis linked by N—H
O interactions. A Hirshfeld surface analysis localized weaker noncovalent interactions, C—H
O and C—H
π, with contact distances close to the sum of the van der Waals radii. Electron density at a local level using the Quantum Theory of Atoms in Molecules (QTAIM) and the Electron Localization Function (ELF), or a semi-local level using noncovalent interactions, was used to rank interactions. Strong closed shell interactions in classical O—H
O and N—H
O hydrogen bonds have electron density highly localized on bond critical points. Weaker delocalized electron density is seen around the
p-methylphenyl rings associated with dispersive C—H
π and H
H interactions.
Supporting information
CCDC references: 2002525; 2038342
For both structures, data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015).
2-[(4-Methylbenzoyl)amino]ethanoic acid (4MHA-I)
top
Crystal data top
C10H11NO3 | Dx = 1.345 Mg m−3 |
Mr = 193.20 | Melting point = 436–438 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.1732 (18) Å | Cell parameters from 770 reflections |
b = 8.286 (3) Å | θ = 1.8–19.1° |
c = 22.264 (8) Å | µ = 0.10 mm−1 |
V = 954.4 (6) Å3 | T = 298 K |
Z = 4 | Needle, colourless |
F(000) = 408 | 0.41 × 0.18 × 0.01 mm |
Data collection top
Bruker SMART APEXII CCD diffractometer | 770 independent reflections |
Radiation source: sealed tube | 723 reflections with I > 2σ(I) |
Detector resolution: CCD pixels mm-1 | Rint = 0.026 |
φ and ω scans | θmax = 19.1°, θmin = 1.8° |
Absorption correction: multi-scan (Jacobson, 1998) | h = −4→4 |
Tmin = 0.958, Tmax = 0.998 | k = −6→7 |
6711 measured reflections | l = −20→20 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.027 | Hydrogen site location: mixed |
wR(F2) = 0.071 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0599P)2 + 0.0172P] where P = (Fo2 + 2Fc2)/3 |
770 reflections | (Δ/σ)max < 0.001 |
136 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.10 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | −0.3753 (6) | 0.8008 (3) | 0.31657 (13) | 0.0613 (9) | |
H1 | −0.504 (8) | 0.739 (5) | 0.3196 (16) | 0.070 (15)* | |
O2 | −0.4221 (5) | 0.7580 (3) | 0.21876 (12) | 0.0645 (9) | |
O3 | −0.2270 (6) | 1.1150 (4) | 0.16192 (11) | 0.0699 (9) | |
N1 | 0.0379 (7) | 0.9240 (5) | 0.19607 (13) | 0.0491 (10) | |
H4 | 0.162 (8) | 0.868 (4) | 0.1870 (17) | 0.050 (14)* | |
C1 | −0.3075 (7) | 0.8176 (4) | 0.25990 (19) | 0.0454 (10) | |
C2 | −0.0731 (7) | 0.9227 (5) | 0.25493 (16) | 0.0534 (11) | |
H2 | −0.119709 | 1.032135 | 0.265935 | 0.064* | |
H3 | 0.055862 | 0.885348 | 0.283345 | 0.064* | |
C3 | −0.0495 (8) | 1.0202 (5) | 0.15193 (17) | 0.0441 (10) | |
C4 | 0.0671 (7) | 1.0057 (4) | 0.09194 (15) | 0.0378 (9) | |
C5 | −0.0509 (7) | 1.0859 (4) | 0.04457 (17) | 0.0500 (10) | |
H5 | −0.195290 | 1.149695 | 0.052026 | 0.060* | |
C6 | 0.0414 (8) | 1.0730 (4) | −0.01318 (15) | 0.0532 (10) | |
H6 | −0.043247 | 1.126613 | −0.044163 | 0.064* | |
C7 | 0.2582 (8) | 0.9816 (4) | −0.02586 (14) | 0.0473 (10) | |
C8 | 0.3785 (7) | 0.9043 (4) | 0.02107 (17) | 0.0517 (10) | |
H7 | 0.524717 | 0.842303 | 0.013471 | 0.062* | |
C9 | 0.2877 (7) | 0.9164 (4) | 0.07919 (16) | 0.0481 (10) | |
H8 | 0.375048 | 0.864338 | 0.110127 | 0.058* | |
C10 | 0.3603 (9) | 0.9662 (5) | −0.08925 (17) | 0.0755 (13) | |
H9 | 0.304594 | 0.865340 | −0.106100 | 0.113* | |
H10 | 0.545739 | 0.969891 | −0.088657 | 0.113* | |
H11 | 0.295311 | 1.053460 | −0.113246 | 0.113* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0575 (18) | 0.080 (2) | 0.047 (2) | −0.0214 (18) | 0.0104 (15) | 0.0041 (14) |
O2 | 0.0666 (19) | 0.0796 (19) | 0.0473 (16) | −0.0193 (19) | −0.0006 (14) | −0.0041 (13) |
O3 | 0.0661 (18) | 0.0717 (17) | 0.0717 (19) | 0.0264 (19) | 0.0213 (16) | 0.0001 (14) |
N1 | 0.045 (2) | 0.061 (2) | 0.042 (3) | −0.001 (2) | 0.0108 (18) | 0.0076 (18) |
C1 | 0.050 (3) | 0.052 (2) | 0.034 (3) | 0.005 (2) | 0.006 (2) | 0.005 (2) |
C2 | 0.050 (3) | 0.061 (2) | 0.049 (3) | −0.013 (2) | 0.009 (2) | 0.0043 (17) |
C3 | 0.040 (2) | 0.043 (2) | 0.050 (3) | −0.006 (2) | 0.004 (2) | −0.002 (2) |
C4 | 0.033 (2) | 0.036 (2) | 0.044 (3) | −0.003 (2) | 0.0019 (19) | 0.0026 (18) |
C5 | 0.044 (2) | 0.045 (2) | 0.061 (3) | 0.004 (2) | 0.005 (2) | 0.006 (2) |
C6 | 0.058 (3) | 0.053 (2) | 0.048 (3) | −0.006 (2) | −0.003 (2) | 0.0122 (17) |
C7 | 0.060 (3) | 0.040 (2) | 0.042 (3) | −0.009 (2) | 0.006 (2) | 0.0003 (18) |
C8 | 0.051 (2) | 0.055 (2) | 0.049 (3) | 0.006 (2) | 0.009 (2) | −0.0004 (19) |
C9 | 0.047 (2) | 0.055 (2) | 0.042 (3) | 0.007 (2) | 0.0004 (18) | 0.0073 (17) |
C10 | 0.104 (3) | 0.075 (3) | 0.047 (3) | −0.003 (3) | 0.013 (2) | −0.0019 (19) |
Geometric parameters (Å, º) top
O1—C1 | 1.317 (4) | C8—C9 | 1.380 (4) |
O2—C1 | 1.198 (4) | O1—H1 | 0.840 (4) |
O3—C3 | 1.229 (4) | N1—H4 | 0.820 (4) |
N1—C3 | 1.344 (5) | C2—H2 | 0.970 |
N1—C2 | 1.431 (5) | C2—H3 | 0.970 |
C1—C2 | 1.497 (5) | C5—H5 | 0.930 |
C3—C4 | 1.470 (5) | C6—H6 | 0.930 |
C4—C5 | 1.388 (4) | C8—H7 | 0.930 |
C4—C9 | 1.389 (4) | C9—H8 | 0.930 |
C5—C6 | 1.376 (4) | C10—H9 | 0.960 |
C6—C7 | 1.382 (5) | C10—H10 | 0.960 |
C7—C8 | 1.374 (4) | C10—H11 | 0.960 |
C7—C10 | 1.512 (4) | | |
| | | |
C3—N1—C2 | 122.6 (4) | C3—N1—H4 | 115 (3) |
O2—C1—O1 | 123.9 (3) | N1—C2—H2 | 109.00 |
O2—C1—C2 | 125.8 (3) | N1—C2—H3 | 109.00 |
O1—C1—C2 | 110.4 (4) | C1—C2—H2 | 109.00 |
N1—C2—C1 | 113.4 (3) | C1—C2—H3 | 109.00 |
O3—C3—N1 | 119.9 (4) | H2—C2—H3 | 108.00 |
O3—C3—C4 | 121.6 (4) | C4—C5—H5 | 119.00 |
N1—C3—C4 | 118.5 (4) | C6—C5—H5 | 119.00 |
C5—C4—C9 | 117.4 (3) | C5—C6—H6 | 120.00 |
C5—C4—C3 | 118.1 (4) | C7—C6—H6 | 119.00 |
C9—C4—C3 | 124.5 (3) | C7—C8—H7 | 119.00 |
C6—C5—C4 | 121.4 (3) | C9—C8—H7 | 119.00 |
C5—C6—C7 | 121.0 (3) | C4—C9—H8 | 120.00 |
C8—C7—C6 | 117.9 (3) | C8—C9—H8 | 120.00 |
C8—C7—C10 | 120.8 (4) | C7—C10—H9 | 109.00 |
C6—C7—C10 | 121.3 (3) | C7—C10—H10 | 109.00 |
C7—C8—C9 | 121.6 (3) | C7—C10—H11 | 109.00 |
C8—C9—C4 | 120.6 (3) | H9—C10—H10 | 109.00 |
C1—O1—H1 | 111 (2) | H9—C10—H11 | 109.00 |
C2—N1—H4 | 123 (3) | H10—C10—H11 | 109.00 |
2-[(4-Methylbenzoyl)amino]ethanoic acid (4MHA-II)
top
Crystal data top
C10H11NO3 | Dx = 1.300 Mg m−3 |
Mr = 193.20 | Melting point = 433–434 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.590 (3) Å | Cell parameters from 4019 reflections |
b = 8.670 (3) Å | θ = 2.5–26.4° |
c = 23.811 (7) Å | µ = 0.10 mm−1 |
β = 94.364 (10)° | T = 298 K |
V = 1974.1 (11) Å3 | Rectangular plates, colourless |
Z = 8 | 0.31 × 0.31 × 0.03 mm |
F(000) = 816 | |
Data collection top
Bruker SMART APEXII CCD diffractometer | 4019 independent reflections |
Radiation source: sealed tube | 2413 reflections with I > 2σ(I) |
Detector resolution: CCD pixels mm-1 | Rint = 0.095 |
φ and ω scans | θmax = 26.4°, θmin = 2.5° |
Absorption correction: multi-scan (Jacobson, 1998) | h = −11→11 |
Tmin = 0.970, Tmax = 0.997 | k = −10→10 |
46748 measured reflections | l = −29→29 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.122 | w = 1/[σ2(Fo2) + (0.0438P)2 + 0.6696P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
4019 reflections | Δρmax = 0.22 e Å−3 |
272 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXL2018 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0079 (9) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1A | 0.41603 (16) | 0.55182 (18) | −0.07757 (6) | 0.0490 (4) | |
H1A | 0.509 (3) | 0.575 (3) | −0.0767 (12) | 0.102 (10)* | |
O2A | 0.42402 (13) | 0.69175 (17) | 0.00177 (6) | 0.0489 (4) | |
O3A | 0.31008 (14) | 0.40957 (17) | 0.06907 (6) | 0.0525 (4) | |
N1A | 0.16422 (18) | 0.5815 (2) | 0.02682 (7) | 0.0436 (5) | |
H4A | 0.102 (2) | 0.651 (3) | 0.0297 (9) | 0.055 (7)* | |
C1A | 0.3629 (2) | 0.6070 (2) | −0.03182 (9) | 0.0377 (5) | |
C2A | 0.2158 (2) | 0.5504 (2) | −0.02739 (8) | 0.0442 (5) | |
H2A | 0.154653 | 0.599489 | −0.056412 | 0.053* | |
H3A | 0.212763 | 0.440045 | −0.034180 | 0.053* | |
C3A | 0.21786 (19) | 0.5081 (2) | 0.07295 (9) | 0.0410 (5) | |
C4A | 0.16457 (19) | 0.5458 (2) | 0.12847 (9) | 0.0420 (5) | |
C5A | 0.2249 (2) | 0.4715 (3) | 0.17611 (10) | 0.0523 (6) | |
H5A | 0.294401 | 0.398418 | 0.172088 | 0.063* | |
C6A | 0.1842 (2) | 0.5037 (3) | 0.22902 (10) | 0.0596 (7) | |
H6A | 0.227498 | 0.452621 | 0.259964 | 0.072* | |
C7A | 0.0811 (2) | 0.6097 (3) | 0.23724 (10) | 0.0597 (7) | |
C8A | 0.0198 (3) | 0.6815 (3) | 0.18972 (10) | 0.0707 (8) | |
H7A | −0.051433 | 0.752478 | 0.193813 | 0.085* | |
C9A | 0.0606 (2) | 0.6517 (3) | 0.13640 (10) | 0.0611 (7) | |
H8A | 0.017646 | 0.703549 | 0.105564 | 0.073* | |
C10A | 0.0392 (3) | 0.6469 (4) | 0.29573 (10) | 0.0859 (9) | |
H9A | 0.093283 | 0.585227 | 0.322883 | 0.129* | |
H10A | −0.058366 | 0.624906 | 0.297821 | 0.129* | |
H11A | 0.056146 | 0.754149 | 0.303603 | 0.129* | |
O1B | 0.93657 (17) | 0.9188 (2) | −0.07612 (6) | 0.0606 (5) | |
H1B | 1.026 (3) | 0.906 (4) | −0.0719 (13) | 0.114 (12)* | |
O2B | 0.93440 (13) | 0.80226 (17) | 0.00767 (6) | 0.0507 (4) | |
O3B | 0.78581 (13) | 1.09458 (17) | 0.06821 (6) | 0.0473 (4) | |
N1B | 0.66341 (17) | 0.9100 (2) | 0.01986 (7) | 0.0405 (4) | |
H4B | 0.597 (2) | 0.843 (2) | 0.0197 (9) | 0.049 (6)* | |
C1B | 0.8778 (2) | 0.8775 (2) | −0.03010 (8) | 0.0371 (5) | |
C2B | 0.73181 (19) | 0.9378 (2) | −0.03122 (8) | 0.0421 (5) | |
H2B | 0.733513 | 1.048035 | −0.038082 | 0.051* | |
H3B | 0.676804 | 0.890489 | −0.062485 | 0.051* | |
C3B | 0.69173 (18) | 0.9959 (2) | 0.06611 (8) | 0.0375 (5) | |
C4B | 0.60166 (18) | 0.9766 (2) | 0.11392 (8) | 0.0370 (5) | |
C5B | 0.5782 (2) | 1.1050 (3) | 0.14675 (9) | 0.0451 (5) | |
H5B | 0.622658 | 1.197473 | 0.139600 | 0.054* | |
C6B | 0.4898 (2) | 1.0975 (3) | 0.18989 (9) | 0.0518 (6) | |
H6B | 0.474385 | 1.185933 | 0.210651 | 0.062* | |
C7B | 0.4242 (2) | 0.9627 (3) | 0.20284 (9) | 0.0534 (6) | |
C8B | 0.4499 (2) | 0.8348 (3) | 0.17056 (10) | 0.0610 (7) | |
H7B | 0.407618 | 0.741739 | 0.178677 | 0.073* | |
C9B | 0.5361 (2) | 0.8404 (3) | 0.12659 (9) | 0.0522 (6) | |
H8B | 0.549996 | 0.752184 | 0.105495 | 0.063* | |
C10B | 0.3293 (3) | 0.9573 (4) | 0.25101 (11) | 0.0856 (9) | |
H9B | 0.385025 | 0.958497 | 0.286239 | 0.128* | |
H10B | 0.274303 | 0.864701 | 0.248335 | 0.128* | |
H11B | 0.268414 | 1.045391 | 0.248896 | 0.128* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0458 (9) | 0.0544 (10) | 0.0478 (9) | 0.0025 (8) | 0.0103 (7) | −0.0046 (7) |
O2A | 0.0428 (8) | 0.0517 (10) | 0.0523 (9) | −0.0061 (7) | 0.0030 (7) | −0.0066 (8) |
O3A | 0.0405 (8) | 0.0488 (10) | 0.0691 (10) | 0.0102 (7) | 0.0088 (7) | 0.0021 (8) |
N1A | 0.0358 (9) | 0.0453 (12) | 0.0503 (12) | 0.0057 (9) | 0.0072 (8) | 0.0014 (9) |
C1A | 0.0389 (11) | 0.0335 (12) | 0.0404 (12) | 0.0045 (9) | 0.0018 (10) | 0.0046 (10) |
C2A | 0.0434 (11) | 0.0426 (13) | 0.0467 (13) | −0.0041 (10) | 0.0048 (10) | −0.0027 (10) |
C3A | 0.0293 (10) | 0.0377 (12) | 0.0565 (14) | −0.0038 (9) | 0.0051 (9) | 0.0031 (11) |
C4A | 0.0341 (10) | 0.0421 (13) | 0.0496 (13) | −0.0010 (9) | 0.0024 (9) | 0.0038 (10) |
C5A | 0.0440 (12) | 0.0505 (15) | 0.0626 (16) | 0.0021 (11) | 0.0048 (11) | 0.0109 (12) |
C6A | 0.0573 (14) | 0.0695 (17) | 0.0512 (15) | −0.0044 (13) | −0.0017 (12) | 0.0152 (13) |
C7A | 0.0557 (14) | 0.0748 (18) | 0.0487 (15) | −0.0045 (13) | 0.0041 (11) | −0.0018 (13) |
C8A | 0.0685 (16) | 0.090 (2) | 0.0540 (16) | 0.0303 (15) | 0.0069 (13) | −0.0033 (15) |
C9A | 0.0584 (14) | 0.0780 (18) | 0.0464 (14) | 0.0272 (13) | 0.0018 (11) | 0.0026 (13) |
C10A | 0.090 (2) | 0.121 (3) | 0.0477 (15) | 0.0066 (19) | 0.0129 (14) | −0.0029 (16) |
O1B | 0.0432 (9) | 0.0934 (14) | 0.0461 (10) | −0.0017 (9) | 0.0090 (8) | 0.0090 (9) |
O2B | 0.0402 (8) | 0.0568 (10) | 0.0552 (9) | 0.0113 (7) | 0.0037 (7) | 0.0113 (8) |
O3B | 0.0366 (7) | 0.0495 (9) | 0.0560 (9) | −0.0084 (7) | 0.0045 (6) | −0.0017 (7) |
N1B | 0.0311 (9) | 0.0445 (11) | 0.0464 (11) | −0.0034 (8) | 0.0057 (8) | −0.0023 (9) |
C1B | 0.0365 (10) | 0.0383 (12) | 0.0371 (12) | −0.0048 (9) | 0.0054 (9) | −0.0063 (10) |
C2B | 0.0389 (11) | 0.0462 (13) | 0.0410 (12) | 0.0043 (10) | 0.0014 (9) | −0.0003 (10) |
C3B | 0.0278 (10) | 0.0389 (12) | 0.0453 (12) | 0.0033 (9) | −0.0009 (9) | 0.0044 (10) |
C4B | 0.0304 (9) | 0.0405 (13) | 0.0393 (11) | 0.0007 (9) | −0.0024 (8) | 0.0016 (10) |
C5B | 0.0447 (11) | 0.0410 (13) | 0.0501 (13) | −0.0024 (10) | 0.0077 (10) | 0.0046 (11) |
C6B | 0.0518 (13) | 0.0516 (15) | 0.0530 (14) | 0.0092 (11) | 0.0112 (11) | 0.0023 (11) |
C7B | 0.0456 (12) | 0.0636 (17) | 0.0522 (14) | −0.0018 (12) | 0.0116 (10) | 0.0097 (13) |
C8B | 0.0675 (15) | 0.0585 (17) | 0.0582 (15) | −0.0232 (13) | 0.0125 (13) | 0.0071 (13) |
C9B | 0.0637 (14) | 0.0419 (14) | 0.0515 (14) | −0.0104 (11) | 0.0077 (11) | −0.0007 (11) |
C10B | 0.0763 (18) | 0.101 (2) | 0.084 (2) | −0.0021 (17) | 0.0392 (15) | 0.0106 (18) |
Geometric parameters (Å, º) top
O1A—C1A | 1.326 (2) | O1B—C1B | 1.319 (2) |
O2A—C1A | 1.205 (2) | O2B—C1B | 1.206 (2) |
O3A—C3A | 1.238 (2) | O3B—C3B | 1.241 (2) |
N1A—C3A | 1.338 (3) | N1B—C3B | 1.340 (3) |
N1A—C2A | 1.442 (3) | N1B—C2B | 1.445 (2) |
C1A—C2A | 1.506 (3) | C1B—C2B | 1.493 (3) |
C3A—C4A | 1.490 (3) | C3B—C4B | 1.490 (3) |
C4A—C9A | 1.379 (3) | C4B—C9B | 1.382 (3) |
C4A—C5A | 1.391 (3) | C4B—C5B | 1.388 (3) |
C5A—C6A | 1.376 (3) | C5B—C6B | 1.382 (3) |
C6A—C7A | 1.374 (3) | C6B—C7B | 1.374 (3) |
C7A—C8A | 1.383 (3) | C7B—C8B | 1.381 (3) |
C7A—C10A | 1.514 (3) | C7B—C10B | 1.519 (3) |
C8A—C9A | 1.381 (3) | C8B—C9B | 1.384 (3) |
O1A—H1A | 0.910 (3) | O1B—H1B | 0.860 (3) |
N1A—H4A | 0.850 (2) | N1B—H4B | 0.862 (2) |
C2A—H2A | 0.970 | C2B—H2B | 0.970 |
C2A—H3A | 0.970 | C2B—H3B | 0.970 |
C5A—H5A | 0.930 | C5B—H5B | 0.930 |
C6A—H6A | 0.930 | C6B—H6B | 0.930 |
C8A—H7A | 0.930 | C8B—H7B | 0.930 |
C9A—H8A | 0.930 | C9B—H8B | 0.930 |
C10A—H9A | 0.960 | C10B—H9B | 0.960 |
C10A—H10A | 0.960 | C10B—H10B | 0.960 |
C10A—H11A | 0.960 | C10B—H11B | 0.960 |
| | | |
C3A—N1A—C2A | 120.61 (19) | C3B—N1B—C2B | 121.50 (18) |
O2A—C1A—O1A | 124.58 (18) | O2B—C1B—O1B | 124.74 (19) |
C1A—O1A—H1A | 109.7 (2) | C1B—O1B—H1B | 111.0 (2) |
O2A—C1A—C2A | 124.29 (18) | O2B—C1B—C2B | 124.81 (18) |
O1A—C1A—C2A | 111.13 (18) | O1B—C1B—C2B | 110.45 (18) |
N1A—C2A—C1A | 112.87 (17) | N1B—C2B—C1B | 114.32 (16) |
C2A—N1A—H4A | 119.5 (2) | C2B—N1B—H4B | 119.4 (1) |
C3A—N1A—H4A | 119.8 (2) | C3B—N1B—H4B | 118.8 (1) |
O3A—C3A—N1A | 119.9 (2) | O3B—C3B—N1B | 121.14 (18) |
O3A—C3A—C4A | 120.85 (19) | O3B—C3B—C4B | 120.57 (18) |
N1A—C3A—C4A | 119.20 (18) | N1B—C3B—C4B | 118.19 (17) |
C9A—C4A—C5A | 117.2 (2) | C9B—C4B—C5B | 117.79 (18) |
C9A—C4A—C3A | 124.61 (19) | C9B—C4B—C3B | 124.24 (19) |
C5A—C4A—C3A | 118.21 (19) | C5B—C4B—C3B | 117.94 (18) |
C6A—C5A—C4A | 121.6 (2) | C6B—C5B—C4B | 121.1 (2) |
C7A—C6A—C5A | 121.6 (2) | C7B—C6B—C5B | 121.6 (2) |
C6A—C7A—C8A | 116.8 (2) | C6B—C7B—C8B | 117.0 (2) |
C6A—C7A—C10A | 121.2 (2) | C6B—C7B—C10B | 120.4 (2) |
C8A—C7A—C10A | 122.1 (2) | C8B—C7B—C10B | 122.5 (2) |
C9A—C8A—C7A | 122.4 (2) | C7B—C8B—C9B | 122.3 (2) |
C4A—C9A—C8A | 120.6 (2) | C4B—C9B—C8B | 120.2 (2) |
C1A—C2A—H2A | 109.0 | N1B—C2B—H2B | 109.0 |
N1A—C2A—H2A | 109.0 | N1B—C2B—H3B | 109.0 |
N1A—C2A—H3A | 109.0 | C1B—C2B—H2B | 109.0 |
H2A—C2A—H3A | 108.0 | C1B—C2B—H3B | 109.0 |
C1A—C2A—H3A | 109.0 | H2B—C2B—H3B | 108.0 |
C6A—C5A—H5A | 119.0 | C4B—C5B—H5B | 120.0 |
C4A—C5A—H5A | 119.0 | C6B—C5B—H5B | 120.0 |
C7A—C6A—H6A | 119.0 | C5B—C6B—H6B | 119.0 |
C5A—C6A—H6A | 119.0 | C7B—C6B—H6B | 119.0 |
C9A—C8A—H7A | 119.0 | C7B—C8B—H7B | 119.0 |
C7A—C8A—H7A | 119.0 | C9B—C8B—H7B | 119.0 |
C4A—C9A—H8A | 120.0 | C4B—C9B—H8B | 120.0 |
C8A—C9A—H8A | 120.0 | C8B—C9B—H8B | 120.0 |
C7A—C10A—H10A | 109.0 | C7B—C10B—H9B | 109.0 |
C7A—C10A—H9A | 109.0 | C7B—C10B—H10B | 109.0 |
H9A—C10A—H11A | 109.0 | C7B—C10B—H11B | 109.0 |
H9A—C10A—H10A | 109.0 | H9B—C10B—H10B | 109.0 |
C7A—C10A—H11A | 109.0 | H9B—C10B—H11B | 109.0 |
H10A—C10A—H11A | 109.0 | H10B—C10B—H11B | 110.0 |
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