Two conformational polymorphs of 4-methyl­hippuric acid

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.

Computing details

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)

Crystal data

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) Å^3	T = 298 K
Z = 4	Needle, colourless
F(000) = 408	0.41 × 0.18 × 0.01 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.027	Hydrogen site location: mixed
wR(F^2) = 0.071	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0599P)^2 + 0.0172P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

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

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)

Crystal data

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) Å^3	Rectangular plates, colourless
Z = 8	0.31 × 0.31 × 0.03 mm
F(000) = 816

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.122	w = 1/[σ^2(Fo^2) + (0.0438P)^2 + 0.6696P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0079 (9)

Special details

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 (Ų)

	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 (Ų)

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

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