A chiral di­amine: practical implications of a three-stereoisomer cocrystallization

A brief comparison of seven straightforward methods for mol­ecular crystal-volume estimation revealed that their precisions are comparable. A chiral di­amine, N²,N³-bis­[2,6-bis­(propan-2-yl)phen­yl]butane-2,3-di­amine, C₂₈H₄₄N₂, has been used to illustrate the application of the methods. Three stereoisomers of the di­amine cocrystallize in the centrosymmetric space group P2₁/c with Z′ = 1.5. The mol­ecules occupying general positions are RR and SS, whereas that residing on an inversion center is meso. This is one of only ten examples of three stereoisomers with two asymmetric atoms cocrystallizing together reported to the Cambridge Structural Database (CSD). The conformations of the SS/RR and meso molecules differ considerably and lead to statistically significantly different C(asymmetric)—C(asymmetric) bond lengths in the diastereomers. An advanced Python script-based CSD searching technique for chiral compounds is presented.

Computing details

Data collection: APEX3 (Bruker, 2017); cell refinement: APEX3 (Bruker, 2017); data reduction: APEX3 (Bruker, 2017); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

N²,N³-Bis[2,6-bis(propan-2-yl)phenyl]butane-2,3-diamine

Crystal data

C28H44N2	F(000) = 1356
Mr = 408.65	Dx = 1.082 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.992 (5) Å	Cell parameters from 9994 reflections
b = 12.399 (5) Å	θ = 2.4–26.4°
c = 23.385 (9) Å	µ = 0.06 mm^−1
β = 92.810 (13)°	T = 100 K
V = 3762 (2) Å^3	Needle, colourless
Z = 6	0.19 × 0.05 × 0.04 mm

Data collection

Bruker APEXII Quazar diffractometer	7718 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	5851 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.065
Detector resolution: 7.9 pixels mm^-1	θmax = 26.4°, θmin = 1.7°
0.5° ω and 0.5° φ scans	h = −16→16
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −15→15
Tmin = 0.938, Tmax = 0.992	l = −29→29
67111 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.113	w = 1/[σ^2(Fo^2) + (0.0325P)^2 + 2.4243P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
7718 reflections	Δρmax = 0.25 e Å^−3
433 parameters	Δρmin = −0.22 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
N1	0.32615 (10)	0.60265 (10)	0.27604 (6)	0.0154 (3)
H1	0.2824 (14)	0.6061 (14)	0.2483 (8)	0.019 (5)*
N2	0.47351 (10)	0.86690 (10)	0.27191 (5)	0.0151 (3)
H2	0.5190 (14)	0.8545 (15)	0.2448 (8)	0.025 (5)*
C1	0.28063 (12)	0.61417 (12)	0.33003 (6)	0.0164 (3)
C2	0.18199 (13)	0.65947 (12)	0.33532 (7)	0.0184 (3)
C3	0.14309 (14)	0.66752 (13)	0.38961 (7)	0.0228 (4)
H3	0.077012	0.698677	0.393557	0.027*
C4	0.19830 (14)	0.63127 (14)	0.43792 (7)	0.0262 (4)
H4	0.170986	0.638554	0.474669	0.031*
C5	0.29369 (14)	0.58434 (14)	0.43207 (7)	0.0252 (4)
H5	0.331313	0.558699	0.465188	0.030*
C6	0.33587 (13)	0.57378 (13)	0.37888 (7)	0.0195 (3)
C7	0.11411 (12)	0.69901 (13)	0.28458 (7)	0.0210 (4)
H7	0.151724	0.684859	0.249043	0.025*
C8	0.01273 (14)	0.63624 (15)	0.27969 (8)	0.0291 (4)
H8A	0.027330	0.559233	0.275229	0.044*
H8B	−0.028835	0.661888	0.246323	0.044*
H8C	−0.025259	0.647371	0.314391	0.044*
C9	0.09234 (14)	0.82053 (14)	0.28711 (8)	0.0268 (4)
H9A	0.054884	0.836786	0.321441	0.040*
H9B	0.050590	0.842186	0.252991	0.040*
H9C	0.157649	0.860215	0.288504	0.040*
C10	0.43774 (13)	0.51382 (13)	0.37514 (7)	0.0222 (4)
H10	0.457935	0.516924	0.334453	0.027*
C11	0.42620 (15)	0.39498 (15)	0.39125 (9)	0.0323 (4)
H11A	0.410270	0.389404	0.431677	0.048*
H11B	0.490715	0.356798	0.384963	0.048*
H11C	0.370217	0.362611	0.367440	0.048*
C12	0.52426 (15)	0.56649 (16)	0.41240 (8)	0.0330 (4)
H12A	0.533959	0.641072	0.399868	0.049*
H12B	0.588378	0.526057	0.408606	0.049*
H12C	0.505712	0.565995	0.452513	0.049*
C13	0.41327 (12)	0.67441 (12)	0.26426 (6)	0.0147 (3)
H13	0.466264	0.664789	0.296327	0.018*
C14	0.46096 (13)	0.63449 (13)	0.20982 (7)	0.0211 (4)
H14A	0.491633	0.563177	0.216749	0.032*
H14B	0.514455	0.685105	0.198833	0.032*
H14C	0.407449	0.629530	0.178913	0.032*
C15	0.38376 (12)	0.79534 (12)	0.26268 (6)	0.0146 (3)
H15	0.337164	0.808357	0.294764	0.017*
C16	0.32581 (13)	0.83004 (13)	0.20760 (7)	0.0192 (3)
H16A	0.297376	0.902467	0.212520	0.029*
H16B	0.269581	0.779207	0.198559	0.029*
H16C	0.373159	0.830781	0.176241	0.029*
C17	0.52224 (12)	0.86978 (12)	0.32764 (6)	0.0155 (3)
C18	0.46893 (12)	0.91975 (12)	0.37160 (7)	0.0172 (3)
C19	0.51397 (13)	0.92120 (13)	0.42683 (7)	0.0203 (3)
H19	0.476841	0.951261	0.456989	0.024*
C20	0.61138 (13)	0.87996 (13)	0.43881 (7)	0.0224 (4)
H20	0.640959	0.881671	0.476768	0.027*
C21	0.66537 (13)	0.83613 (13)	0.39489 (7)	0.0211 (4)
H21	0.733378	0.810240	0.402877	0.025*
C22	0.62247 (12)	0.82900 (12)	0.33919 (7)	0.0182 (3)
C23	0.36775 (12)	0.98009 (13)	0.36043 (7)	0.0187 (3)
H23	0.345451	0.969853	0.319253	0.022*
C24	0.28184 (13)	0.93803 (14)	0.39695 (7)	0.0251 (4)
H24A	0.274165	0.860067	0.391314	0.038*
H24B	0.216959	0.974134	0.385525	0.038*
H24C	0.299379	0.952935	0.437421	0.038*
C25	0.38382 (13)	1.10120 (13)	0.37095 (7)	0.0217 (4)
H25A	0.403611	1.113415	0.411414	0.033*
H25B	0.319639	1.139873	0.361010	0.033*
H25C	0.438486	1.127659	0.347158	0.033*
C26	0.68753 (12)	0.77985 (13)	0.29321 (7)	0.0211 (4)
H26	0.643129	0.775528	0.257123	0.025*
C27	0.77922 (15)	0.85207 (16)	0.28121 (8)	0.0343 (5)
H27A	0.754319	0.923591	0.269260	0.051*
H27B	0.818282	0.820118	0.250663	0.051*
H27C	0.823910	0.858836	0.316025	0.051*
C28	0.72273 (16)	0.66543 (16)	0.30831 (9)	0.0353 (5)
H28A	0.765904	0.666736	0.343859	0.053*
H28B	0.762538	0.636378	0.277279	0.053*
H28C	0.662354	0.619719	0.313469	0.053*
N3	0.07048 (11)	0.87022 (10)	0.51081 (6)	0.0182 (3)
H3A	0.1355 (16)	0.8942 (16)	0.5028 (8)	0.035 (6)*
C29	0.07930 (12)	0.78335 (12)	0.55107 (6)	0.0168 (3)
C30	0.16899 (13)	0.76839 (12)	0.58636 (7)	0.0182 (3)
C31	0.17508 (13)	0.67856 (13)	0.62228 (7)	0.0206 (4)
H31	0.235950	0.666924	0.645645	0.025*
C32	0.09452 (13)	0.60606 (13)	0.62464 (7)	0.0205 (3)
H32	0.099620	0.546056	0.649882	0.025*
C33	0.00665 (12)	0.62159 (12)	0.59004 (7)	0.0177 (3)
H33	−0.048887	0.572111	0.592020	0.021*
C34	−0.00227 (12)	0.70836 (12)	0.55225 (6)	0.0162 (3)
C35	0.26126 (13)	0.84410 (13)	0.58523 (7)	0.0216 (4)
H35	0.236367	0.913901	0.568169	0.026*
C36	0.30807 (16)	0.86838 (17)	0.64488 (8)	0.0366 (5)
H36A	0.341209	0.803256	0.660806	0.055*
H36B	0.253651	0.891623	0.669710	0.055*
H36C	0.359440	0.925866	0.642465	0.055*
C37	0.34286 (14)	0.79954 (15)	0.54704 (8)	0.0290 (4)
H37A	0.313260	0.791069	0.507942	0.043*
H37B	0.366585	0.729313	0.561696	0.043*
H37C	0.401239	0.849579	0.546910	0.043*
C38	−0.09693 (12)	0.71611 (13)	0.51173 (7)	0.0188 (3)
H38	−0.088037	0.779905	0.486279	0.023*
C39	−0.19441 (13)	0.73373 (15)	0.54443 (8)	0.0279 (4)
H39A	−0.187264	0.799880	0.567217	0.042*
H39B	−0.204666	0.672234	0.569854	0.042*
H39C	−0.253852	0.740389	0.517206	0.042*
C40	−0.10840 (14)	0.61579 (14)	0.47373 (7)	0.0249 (4)
H40A	−0.118112	0.552140	0.497721	0.037*
H40B	−0.046166	0.606602	0.452187	0.037*
H40C	−0.168262	0.624431	0.446961	0.037*
C41	0.00630 (12)	0.96246 (12)	0.52599 (6)	0.0153 (3)
H41	−0.063605	0.933564	0.533542	0.018*
C42	0.04532 (14)	1.02178 (13)	0.57991 (7)	0.0242 (4)
H42A	−0.004732	1.077093	0.589708	0.036*
H42B	0.111590	1.056011	0.573080	0.036*
H42C	0.054191	0.970353	0.611593	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0161 (7)	0.0159 (7)	0.0140 (7)	−0.0022 (5)	0.0006 (6)	−0.0017 (5)
N2	0.0159 (7)	0.0162 (7)	0.0132 (6)	−0.0020 (5)	0.0012 (5)	−0.0007 (5)
C1	0.0198 (8)	0.0118 (7)	0.0176 (8)	−0.0048 (6)	0.0024 (6)	−0.0018 (6)
C2	0.0211 (9)	0.0136 (7)	0.0208 (8)	−0.0054 (6)	0.0048 (7)	−0.0026 (6)
C3	0.0249 (9)	0.0167 (8)	0.0275 (9)	−0.0052 (7)	0.0093 (7)	−0.0038 (7)
C4	0.0364 (11)	0.0217 (9)	0.0212 (9)	−0.0086 (8)	0.0101 (7)	−0.0028 (7)
C5	0.0348 (10)	0.0220 (9)	0.0186 (8)	−0.0061 (8)	0.0008 (7)	0.0025 (7)
C6	0.0236 (9)	0.0146 (8)	0.0204 (8)	−0.0055 (7)	0.0017 (7)	0.0004 (6)
C7	0.0170 (8)	0.0216 (8)	0.0247 (9)	0.0003 (7)	0.0043 (7)	−0.0029 (7)
C8	0.0222 (9)	0.0258 (10)	0.0394 (11)	−0.0022 (7)	0.0020 (8)	−0.0053 (8)
C9	0.0263 (10)	0.0225 (9)	0.0316 (10)	0.0014 (7)	0.0003 (8)	−0.0011 (7)
C10	0.0245 (9)	0.0196 (8)	0.0220 (8)	−0.0008 (7)	−0.0027 (7)	0.0055 (7)
C11	0.0270 (10)	0.0239 (9)	0.0452 (11)	−0.0006 (8)	−0.0052 (8)	0.0076 (8)
C12	0.0284 (10)	0.0372 (11)	0.0329 (10)	−0.0104 (9)	−0.0029 (8)	0.0044 (8)
C13	0.0144 (8)	0.0140 (7)	0.0158 (7)	−0.0016 (6)	0.0001 (6)	−0.0011 (6)
C14	0.0224 (9)	0.0192 (8)	0.0221 (8)	−0.0021 (7)	0.0058 (7)	−0.0042 (6)
C15	0.0133 (8)	0.0139 (7)	0.0163 (7)	−0.0016 (6)	−0.0006 (6)	−0.0011 (6)
C16	0.0197 (8)	0.0178 (8)	0.0197 (8)	−0.0022 (7)	−0.0028 (6)	0.0016 (6)
C17	0.0176 (8)	0.0127 (7)	0.0161 (7)	−0.0039 (6)	−0.0005 (6)	0.0004 (6)
C18	0.0190 (8)	0.0126 (7)	0.0198 (8)	−0.0027 (6)	−0.0008 (6)	−0.0008 (6)
C19	0.0242 (9)	0.0182 (8)	0.0185 (8)	−0.0020 (7)	0.0016 (7)	−0.0030 (6)
C20	0.0267 (9)	0.0221 (9)	0.0176 (8)	−0.0007 (7)	−0.0063 (7)	−0.0013 (7)
C21	0.0175 (8)	0.0201 (8)	0.0252 (9)	−0.0008 (7)	−0.0051 (7)	−0.0004 (7)
C22	0.0172 (8)	0.0158 (8)	0.0214 (8)	−0.0033 (6)	−0.0013 (6)	−0.0004 (6)
C23	0.0214 (9)	0.0172 (8)	0.0172 (8)	0.0005 (7)	−0.0014 (6)	−0.0030 (6)
C24	0.0210 (9)	0.0249 (9)	0.0293 (9)	−0.0030 (7)	0.0011 (7)	−0.0009 (7)
C25	0.0245 (9)	0.0170 (8)	0.0237 (9)	0.0021 (7)	0.0014 (7)	−0.0023 (6)
C26	0.0162 (8)	0.0246 (9)	0.0223 (8)	0.0005 (7)	−0.0009 (6)	−0.0024 (7)
C27	0.0335 (11)	0.0371 (11)	0.0331 (10)	−0.0073 (9)	0.0103 (8)	−0.0067 (8)
C28	0.0377 (11)	0.0320 (10)	0.0373 (11)	0.0098 (9)	0.0114 (9)	−0.0003 (8)
N3	0.0208 (8)	0.0141 (7)	0.0200 (7)	0.0015 (6)	0.0049 (6)	0.0020 (5)
C29	0.0223 (8)	0.0138 (7)	0.0147 (7)	0.0012 (6)	0.0045 (6)	−0.0011 (6)
C30	0.0209 (8)	0.0147 (8)	0.0190 (8)	−0.0009 (6)	0.0029 (6)	−0.0021 (6)
C31	0.0205 (9)	0.0184 (8)	0.0227 (8)	0.0012 (7)	−0.0014 (7)	0.0017 (6)
C32	0.0260 (9)	0.0145 (8)	0.0212 (8)	0.0014 (7)	0.0027 (7)	0.0030 (6)
C33	0.0199 (8)	0.0139 (8)	0.0196 (8)	−0.0013 (6)	0.0046 (6)	−0.0004 (6)
C34	0.0185 (8)	0.0146 (7)	0.0159 (7)	0.0024 (6)	0.0046 (6)	−0.0031 (6)
C35	0.0213 (9)	0.0191 (8)	0.0241 (9)	−0.0033 (7)	−0.0007 (7)	0.0030 (7)
C36	0.0431 (12)	0.0387 (11)	0.0279 (10)	−0.0211 (10)	0.0001 (9)	−0.0038 (8)
C37	0.0249 (10)	0.0331 (10)	0.0291 (10)	−0.0076 (8)	0.0031 (8)	−0.0001 (8)
C38	0.0209 (9)	0.0166 (8)	0.0187 (8)	−0.0012 (7)	0.0005 (6)	0.0018 (6)
C39	0.0206 (9)	0.0358 (10)	0.0273 (9)	0.0054 (8)	0.0005 (7)	−0.0011 (8)
C40	0.0302 (10)	0.0219 (9)	0.0224 (9)	−0.0042 (8)	−0.0007 (7)	−0.0003 (7)
C41	0.0171 (8)	0.0137 (7)	0.0155 (8)	−0.0006 (6)	0.0033 (6)	−0.0001 (6)
C42	0.0349 (10)	0.0198 (8)	0.0179 (8)	0.0035 (7)	0.0000 (7)	−0.0009 (6)

Geometric parameters (Å, º)

N1—H1	0.842 (18)	C23—H23	1.0000
N1—C1	1.427 (2)	C23—C24	1.530 (2)
N1—C13	1.476 (2)	C23—C25	1.534 (2)
N2—H2	0.901 (19)	C24—H24A	0.9800
N2—C15	1.4727 (19)	C24—H24B	0.9800
N2—C17	1.421 (2)	C24—H24C	0.9800
C1—C2	1.410 (2)	C25—H25A	0.9800
C1—C6	1.411 (2)	C25—H25B	0.9800
C2—C3	1.393 (2)	C25—H25C	0.9800
C2—C7	1.524 (2)	C26—H26	1.0000
C3—H3	0.9500	C26—C27	1.527 (2)
C3—C4	1.383 (3)	C26—C28	1.527 (2)
C4—H4	0.9500	C27—H27A	0.9800
C4—C5	1.382 (3)	C27—H27B	0.9800
C5—H5	0.9500	C27—H27C	0.9800
C5—C6	1.390 (2)	C28—H28A	0.9800
C6—C10	1.524 (2)	C28—H28B	0.9800
C7—H7	1.0000	C28—H28C	0.9800
C7—C8	1.529 (2)	N3—H3A	0.92 (2)
C7—C9	1.535 (2)	N3—C29	1.431 (2)
C8—H8A	0.9800	N3—C41	1.469 (2)
C8—H8B	0.9800	C29—C30	1.407 (2)
C8—H8C	0.9800	C29—C34	1.411 (2)
C9—H9A	0.9800	C30—C31	1.395 (2)
C9—H9B	0.9800	C30—C35	1.524 (2)
C9—H9C	0.9800	C31—H31	0.9500
C10—H10	1.0000	C31—C32	1.383 (2)
C10—C11	1.530 (2)	C32—H32	0.9500
C10—C12	1.534 (2)	C32—C33	1.380 (2)
C11—H11A	0.9800	C33—H33	0.9500
C11—H11B	0.9800	C33—C34	1.393 (2)
C11—H11C	0.9800	C34—C38	1.518 (2)
C12—H12A	0.9800	C35—H35	1.0000
C12—H12B	0.9800	C35—C36	1.524 (2)
C12—H12C	0.9800	C35—C37	1.523 (2)
C13—H13	1.0000	C36—H36A	0.9800
C13—C14	1.525 (2)	C36—H36B	0.9800
C13—C15	1.548 (2)	C36—H36C	0.9800
C14—H14A	0.9800	C37—H37A	0.9800
C14—H14B	0.9800	C37—H37B	0.9800
C14—H14C	0.9800	C37—H37C	0.9800
C15—H15	1.0000	C38—H38	1.0000
C15—C16	1.522 (2)	C38—C39	1.527 (2)
C16—H16A	0.9800	C38—C40	1.532 (2)
C16—H16B	0.9800	C39—H39A	0.9800
C16—H16C	0.9800	C39—H39B	0.9800
C17—C18	1.411 (2)	C39—H39C	0.9800
C17—C22	1.411 (2)	C40—H40A	0.9800
C18—C19	1.392 (2)	C40—H40B	0.9800
C18—C23	1.524 (2)	C40—H40C	0.9800
C19—H19	0.9500	C41—C41^i	1.534 (3)
C19—C20	1.381 (2)	C41—H41	1.0000
C20—H20	0.9500	C41—C42	1.525 (2)
C20—C21	1.383 (2)	C42—H42A	0.9800
C21—H21	0.9500	C42—H42B	0.9800
C21—C22	1.394 (2)	C42—H42C	0.9800
C22—C26	1.527 (2)
C1—N1—H1	112.5 (12)	C18—C23—C25	110.09 (13)
C1—N1—C13	117.35 (12)	C24—C23—H23	108.0
C13—N1—H1	108.7 (12)	C24—C23—C25	109.96 (14)
C15—N2—H2	109.7 (12)	C25—C23—H23	108.0
C17—N2—H2	111.8 (12)	C23—C24—H24A	109.5
C17—N2—C15	117.61 (12)	C23—C24—H24B	109.5
C2—C1—N1	122.35 (14)	C23—C24—H24C	109.5
C2—C1—C6	119.92 (14)	H24A—C24—H24B	109.5
C6—C1—N1	117.66 (14)	H24A—C24—H24C	109.5
C1—C2—C7	123.61 (14)	H24B—C24—H24C	109.5
C3—C2—C1	118.71 (15)	C23—C25—H25A	109.5
C3—C2—C7	117.68 (15)	C23—C25—H25B	109.5
C2—C3—H3	119.2	C23—C25—H25C	109.5
C4—C3—C2	121.62 (17)	H25A—C25—H25B	109.5
C4—C3—H3	119.2	H25A—C25—H25C	109.5
C3—C4—H4	120.4	H25B—C25—H25C	109.5
C5—C4—C3	119.19 (16)	C22—C26—H26	107.4
C5—C4—H4	120.4	C22—C26—C27	111.04 (14)
C4—C5—H5	119.2	C27—C26—H26	107.4
C4—C5—C6	121.54 (16)	C28—C26—C22	112.21 (14)
C6—C5—H5	119.2	C28—C26—H26	107.4
C1—C6—C10	122.37 (14)	C28—C26—C27	111.08 (15)
C5—C6—C1	118.95 (16)	C26—C27—H27A	109.5
C5—C6—C10	118.61 (15)	C26—C27—H27B	109.5
C2—C7—H7	107.6	C26—C27—H27C	109.5
C2—C7—C8	110.97 (14)	H27A—C27—H27B	109.5
C2—C7—C9	112.73 (14)	H27A—C27—H27C	109.5
C8—C7—H7	107.6	H27B—C27—H27C	109.5
C8—C7—C9	110.05 (14)	C26—C28—H28A	109.5
C9—C7—H7	107.6	C26—C28—H28B	109.5
C7—C8—H8A	109.5	C26—C28—H28C	109.5
C7—C8—H8B	109.5	H28A—C28—H28B	109.5
C7—C8—H8C	109.5	H28A—C28—H28C	109.5
H8A—C8—H8B	109.5	H28B—C28—H28C	109.5
H8A—C8—H8C	109.5	C29—N3—H3A	109.3 (13)
H8B—C8—H8C	109.5	C29—N3—C41	117.06 (13)
C7—C9—H9A	109.5	C41—N3—H3A	109.5 (13)
C7—C9—H9B	109.5	C30—C29—N3	121.49 (14)
C7—C9—H9C	109.5	C30—C29—C34	120.20 (14)
H9A—C9—H9B	109.5	C34—C29—N3	118.20 (14)
H9A—C9—H9C	109.5	C29—C30—C35	122.57 (14)
H9B—C9—H9C	109.5	C31—C30—C29	118.64 (15)
C6—C10—H10	107.7	C31—C30—C35	118.75 (14)
C6—C10—C11	111.09 (14)	C30—C31—H31	119.3
C6—C10—C12	111.96 (15)	C32—C31—C30	121.50 (15)
C11—C10—H10	107.7	C32—C31—H31	119.3
C11—C10—C12	110.37 (14)	C31—C32—H32	120.3
C12—C10—H10	107.7	C33—C32—C31	119.46 (15)
C10—C11—H11A	109.5	C33—C32—H32	120.3
C10—C11—H11B	109.5	C32—C33—H33	119.3
C10—C11—H11C	109.5	C32—C33—C34	121.35 (15)
H11A—C11—H11B	109.5	C34—C33—H33	119.3
H11A—C11—H11C	109.5	C29—C34—C38	122.16 (14)
H11B—C11—H11C	109.5	C33—C34—C29	118.80 (14)
C10—C12—H12A	109.5	C33—C34—C38	118.97 (14)
C10—C12—H12B	109.5	C30—C35—H35	107.5
C10—C12—H12C	109.5	C30—C35—C36	112.62 (14)
H12A—C12—H12B	109.5	C36—C35—H35	107.5
H12A—C12—H12C	109.5	C37—C35—C30	110.95 (14)
H12B—C12—H12C	109.5	C37—C35—H35	107.5
N1—C13—H13	107.1	C37—C35—C36	110.50 (15)
N1—C13—C14	107.86 (12)	C35—C36—H36A	109.5
N1—C13—C15	113.39 (13)	C35—C36—H36B	109.5
C14—C13—H13	107.1	C35—C36—H36C	109.5
C14—C13—C15	113.88 (13)	H36A—C36—H36B	109.5
C15—C13—H13	107.1	H36A—C36—H36C	109.5
C13—C14—H14A	109.5	H36B—C36—H36C	109.5
C13—C14—H14B	109.5	C35—C37—H37A	109.5
C13—C14—H14C	109.5	C35—C37—H37B	109.5
H14A—C14—H14B	109.5	C35—C37—H37C	109.5
H14A—C14—H14C	109.5	H37A—C37—H37B	109.5
H14B—C14—H14C	109.5	H37A—C37—H37C	109.5
N2—C15—C13	112.75 (12)	H37B—C37—H37C	109.5
N2—C15—H15	107.3	C34—C38—H38	107.9
N2—C15—C16	108.00 (12)	C34—C38—C39	111.28 (13)
C13—C15—H15	107.3	C34—C38—C40	111.31 (13)
C16—C15—C13	113.94 (12)	C39—C38—H38	107.9
C16—C15—H15	107.3	C39—C38—C40	110.32 (14)
C15—C16—H16A	109.5	C40—C38—H38	107.9
C15—C16—H16B	109.5	C38—C39—H39A	109.5
C15—C16—H16C	109.5	C38—C39—H39B	109.5
H16A—C16—H16B	109.5	C38—C39—H39C	109.5
H16A—C16—H16C	109.5	H39A—C39—H39B	109.5
H16B—C16—H16C	109.5	H39A—C39—H39C	109.5
C18—C17—N2	117.82 (14)	H39B—C39—H39C	109.5
C22—C17—N2	122.14 (14)	C38—C40—H40A	109.5
C22—C17—C18	119.97 (14)	C38—C40—H40B	109.5
C17—C18—C23	122.75 (14)	C38—C40—H40C	109.5
C19—C18—C17	118.87 (15)	H40A—C40—H40B	109.5
C19—C18—C23	118.21 (14)	H40A—C40—H40C	109.5
C18—C19—H19	119.2	H40B—C40—H40C	109.5
C20—C19—C18	121.54 (15)	N3—C41—C41^i	108.71 (15)
C20—C19—H19	119.2	N3—C41—H41	107.2
C19—C20—H20	120.4	N3—C41—C42	113.93 (13)
C19—C20—C21	119.20 (15)	C41^i—C41—H41	107.2
C21—C20—H20	120.4	C42—C41—C41^i	112.39 (16)
C20—C21—H21	119.2	C42—C41—H41	107.2
C20—C21—C22	121.65 (16)	C41—C42—H42A	109.5
C22—C21—H21	119.2	C41—C42—H42B	109.5
C17—C22—C26	123.10 (14)	C41—C42—H42C	109.5
C21—C22—C17	118.62 (15)	H42A—C42—H42B	109.5
C21—C22—C26	118.26 (14)	H42A—C42—H42C	109.5
C18—C23—H23	108.0	H42B—C42—H42C	109.5
C18—C23—C24	112.57 (14)
N1—C1—C2—C3	179.84 (14)	C17—C22—C26—C27	110.96 (18)
N1—C1—C2—C7	0.8 (2)	C17—C22—C26—C28	−124.05 (17)
N1—C1—C6—C5	179.68 (14)	C18—C17—C22—C21	2.1 (2)
N1—C1—C6—C10	−3.5 (2)	C18—C17—C22—C26	−176.31 (14)
N1—C13—C15—N2	159.17 (12)	C18—C19—C20—C21	0.0 (2)
N1—C13—C15—C16	−77.27 (17)	C19—C18—C23—C24	−59.75 (19)
N2—C17—C18—C19	178.42 (14)	C19—C18—C23—C25	63.32 (19)
N2—C17—C18—C23	−6.5 (2)	C19—C20—C21—C22	−2.4 (3)
N2—C17—C22—C21	179.17 (14)	C20—C21—C22—C17	1.3 (2)
N2—C17—C22—C26	0.8 (2)	C20—C21—C22—C26	179.79 (15)
C1—N1—C13—C14	170.02 (13)	C21—C22—C26—C27	−67.4 (2)
C1—N1—C13—C15	−62.91 (17)	C21—C22—C26—C28	57.5 (2)
C1—C2—C3—C4	−0.7 (2)	C22—C17—C18—C19	−4.4 (2)
C1—C2—C7—C8	118.89 (17)	C22—C17—C18—C23	170.70 (14)
C1—C2—C7—C9	−117.15 (17)	C23—C18—C19—C20	−171.92 (15)
C1—C6—C10—C11	−112.10 (17)	N3—C29—C30—C31	−176.28 (14)
C1—C6—C10—C12	124.01 (17)	N3—C29—C30—C35	1.3 (2)
C2—C1—C6—C5	−3.1 (2)	N3—C29—C34—C33	178.11 (14)
C2—C1—C6—C10	173.69 (14)	N3—C29—C34—C38	1.2 (2)
C2—C3—C4—C5	−1.1 (2)	C29—N3—C41—C41^i	−171.50 (15)
C3—C2—C7—C8	−60.18 (19)	C29—N3—C41—C42	62.32 (19)
C3—C2—C7—C9	63.79 (19)	C29—C30—C31—C32	−1.4 (2)
C3—C4—C5—C6	0.7 (3)	C29—C30—C35—C36	138.84 (17)
C4—C5—C6—C1	1.4 (2)	C29—C30—C35—C37	−96.70 (18)
C4—C5—C6—C10	−175.56 (15)	C29—C34—C38—C39	−117.52 (16)
C5—C6—C10—C11	64.7 (2)	C29—C34—C38—C40	118.98 (16)
C5—C6—C10—C12	−59.2 (2)	C30—C29—C34—C33	1.8 (2)
C6—C1—C2—C3	2.8 (2)	C30—C29—C34—C38	−175.11 (14)
C6—C1—C2—C7	−176.27 (14)	C30—C31—C32—C33	1.1 (2)
C7—C2—C3—C4	178.43 (15)	C31—C30—C35—C36	−43.5 (2)
C13—N1—C1—C2	108.56 (17)	C31—C30—C35—C37	80.93 (19)
C13—N1—C1—C6	−74.32 (18)	C31—C32—C33—C34	0.7 (2)
C14—C13—C15—N2	−76.99 (16)	C32—C33—C34—C29	−2.1 (2)
C14—C13—C15—C16	46.57 (18)	C32—C33—C34—C38	174.93 (14)
C15—N2—C17—C18	−70.75 (18)	C33—C34—C38—C39	65.53 (19)
C15—N2—C17—C22	112.11 (17)	C33—C34—C38—C40	−57.97 (19)
C17—N2—C15—C13	−70.30 (17)	C34—C29—C30—C31	−0.1 (2)
C17—N2—C15—C16	162.91 (13)	C34—C29—C30—C35	177.49 (14)
C17—C18—C19—C20	3.4 (2)	C35—C30—C31—C32	−179.10 (15)
C17—C18—C23—C24	125.15 (16)	C41—N3—C29—C30	−104.25 (18)
C17—C18—C23—C25	−111.78 (16)	C41—N3—C29—C34	79.54 (18)

Symmetry code: (i) −x, −y+2, −z+1.