2,5-Bis[5-(3,5-dido­decyl­oxyphen­yl)-1,3,4-oxa­diazol-2-yl]-3,6-di­methyl­pyrazine

The nearly planar mol­ecule of the title compound, C₇₀H₁₁₂N₆O₆, is centrosymmetric with two all-s-trans chains, the other two chains have an s-cis unit starting with the oxygen atoms. The chains are inter­digitated in the packing.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.050
• wR factor = 0.143
• Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full value Low .      0.925 Why?

Author Response: geometrical limitations of the instrument

Alert level B
PLAT911_ALERT_3_B Missing FCF Refl Between Thmin & STh/L=    0.600        445 Report

Author Response: geometrical limitations of the instrument.

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.75 Report
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      6.207 Check

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.003 Degree
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....         C4 Check
PLAT398_ALERT_2_G Deviating  C-O-C   Angle From 120 for O9       .      102.2 Degree
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        44% Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          5 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          3 Note
PLAT967_ALERT_5_G Note: Two-Theta Cutoff Value in Embedded .res ..      136.0 Degree
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info

   1 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: X-AREA WinXpose (Stoe & Cie, 2019); cell refinement: X-AREA Recipe (Stoe & Cie, 2019); data reduction: X-AREA Integrate (Stoe & Cie, 2019); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020).

2,5-Bis[5-(3,5-didodecyloxyphenyl)-1,3,4-oxadiazol-2-yl]-3,6-dimethylpyrazine

Crystal data

C70H112N6O6	F(000) = 622
Mr = 1133.65	Dx = 1.137 Mg m^−3
Triclinic, P1	Melting point: 399 K
a = 8.1119 (3) Å	Cu Kα radiation, λ = 1.54178 Å
b = 9.5566 (3) Å	Cell parameters from 12421 reflections
c = 22.2332 (8) Å	θ = 2.0–71.5°
α = 90.553 (3)°	µ = 0.56 mm^−1
β = 91.592 (3)°	T = 120 K
γ = 106.047 (3)°	Block, colorless
V = 1655.50 (10) Å^3	0.14 × 0.08 × 0.03 mm
Z = 1

Data collection

Stoe Stadivari diffractometer	3360 reflections with I > 2σ(I)
Radiation source: microfocus tube	Rint = 0.090
Detector resolution: 13.33 pixels mm^-1	θmax = 68.0°, θmin = 2.0°
rotation method, ω scans	h = −9→9
46250 measured reflections	k = −11→11
5582 independent reflections	l = −26→26

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.143	w = 1/[σ^2(Fo^2) + (0.0817P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.94	(Δ/σ)max < 0.001
5582 reflections	Δρmax = 0.57 e Å^−3
373 parameters	Δρmin = −0.21 e Å^−3
0 restraints

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.

Refinement. Hydrogen atoms were placed at calculated positions and were refined in the riding-model approximation with C_aromatic–H = 0.95 Å, C_methylene–H = 0.99 Å, and C_methyl–H = 0.98 Å and with U_iso(H) = 1.2 U_eq(C) or U_iso(H) = 1.5 U_eq(C_methyl). The methyl groups were allowed to rotate but not to tip.

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

	x	y	z	Uiso*/Ueq
N1	0.4330 (2)	0.5972 (2)	0.53110 (8)	0.0250 (4)
C2	0.4840 (3)	0.4951 (2)	0.56115 (10)	0.0248 (5)
C3	0.5511 (3)	0.3976 (2)	0.52863 (10)	0.0240 (5)
C4	0.4685 (3)	0.4954 (2)	0.62820 (10)	0.0289 (5)
H4A	0.417809	0.572892	0.640336	0.043*
H4B	0.582537	0.512466	0.647519	0.043*
H4C	0.394915	0.401114	0.640563	0.043*
C5	0.6013 (3)	0.2776 (2)	0.55730 (10)	0.0244 (5)
N6	0.5959 (3)	0.2403 (2)	0.61295 (8)	0.0300 (5)
N7	0.6494 (3)	0.1122 (2)	0.61502 (8)	0.0304 (5)
C8	0.6824 (3)	0.0848 (2)	0.56041 (9)	0.0245 (5)
O9	0.6569 (2)	0.18470 (16)	0.52090 (6)	0.0244 (4)
C10	0.7459 (3)	−0.0346 (2)	0.53796 (10)	0.0236 (5)
C11	0.7808 (3)	−0.1302 (2)	0.57946 (10)	0.0247 (5)
H11	0.757950	−0.120829	0.620758	0.030*
C12	0.8500 (3)	−0.2404 (2)	0.56000 (9)	0.0241 (5)
C13	0.8827 (3)	−0.2539 (2)	0.49996 (9)	0.0240 (5)
H13	0.931369	−0.328264	0.486925	0.029*
C14	0.8443 (3)	−0.1580 (2)	0.45843 (9)	0.0228 (5)
C15	0.7753 (3)	−0.0471 (2)	0.47684 (10)	0.0240 (5)
H15	0.749062	0.018229	0.448630	0.029*
O16	0.8803 (2)	−0.32816 (17)	0.60445 (6)	0.0287 (4)
C17	0.9903 (3)	−0.4195 (2)	0.59294 (10)	0.0277 (5)
H17A	1.103735	−0.360190	0.580051	0.033*
H17B	0.938976	−0.492003	0.560728	0.033*
C18	1.0092 (3)	−0.4953 (2)	0.65108 (10)	0.0291 (5)
H18A	1.089988	−0.554965	0.645231	0.035*
H18B	0.896548	−0.562135	0.660717	0.035*
C19	1.0742 (3)	−0.3907 (3)	0.70426 (10)	0.0304 (5)
H19A	0.986994	−0.339312	0.713321	0.036*
H19B	1.180210	−0.316845	0.693067	0.036*
C20	1.1118 (3)	−0.4684 (3)	0.76074 (10)	0.0307 (6)
H20A	1.214195	−0.503073	0.754146	0.037*
H20B	1.013675	−0.554834	0.766994	0.037*
C21	1.1432 (3)	−0.3723 (3)	0.81777 (10)	0.0333 (6)
H21A	1.240036	−0.284909	0.811395	0.040*
H21B	1.039951	−0.339102	0.824945	0.040*
C22	1.1837 (3)	−0.4506 (3)	0.87345 (10)	0.0323 (6)
H22A	1.289125	−0.480808	0.866759	0.039*
H22B	1.088599	−0.539766	0.878963	0.039*
C23	1.2092 (3)	−0.3569 (3)	0.93082 (10)	0.0334 (6)
H23A	1.104016	−0.326191	0.937327	0.040*
H23B	1.304701	−0.267990	0.925339	0.040*
C24	1.2490 (3)	−0.4354 (3)	0.98696 (10)	0.0319 (6)
H24A	1.153882	−0.524675	0.992303	0.038*
H24B	1.354663	−0.465467	0.980597	0.038*
C25	1.2732 (3)	−0.3418 (3)	1.04433 (10)	0.0335 (6)
H25A	1.367141	−0.251867	1.038704	0.040*
H25B	1.166897	−0.312784	1.050905	0.040*
C26	1.3151 (3)	−0.4182 (3)	1.10030 (10)	0.0338 (6)
H26A	1.221315	−0.508143	1.106018	0.041*
H26B	1.421681	−0.446844	1.093908	0.041*
C27	1.3385 (4)	−0.3235 (3)	1.15719 (10)	0.0374 (6)
H27A	1.231819	−0.294916	1.163560	0.045*
H27B	1.432107	−0.233484	1.151410	0.045*
C28	1.3808 (4)	−0.3996 (3)	1.21353 (11)	0.0446 (7)
H28A	1.287662	−0.488016	1.220028	0.067*
H28B	1.393540	−0.333864	1.248507	0.067*
H28C	1.488134	−0.425691	1.208107	0.067*
O29	0.8808 (2)	−0.18117 (16)	0.40032 (6)	0.0284 (4)
C30	0.8427 (3)	−0.0874 (2)	0.35478 (9)	0.0287 (5)
H30A	0.910389	0.014655	0.362777	0.034*
H30B	0.719233	−0.092015	0.354322	0.034*
C31	0.8895 (3)	−0.1410 (3)	0.29551 (10)	0.0326 (6)
H31A	0.825290	−0.244774	0.289450	0.039*
H31B	1.013475	−0.134541	0.296749	0.039*
C32	0.8501 (4)	−0.0542 (3)	0.24239 (10)	0.0329 (6)
H32A	0.734167	−0.040872	0.246459	0.039*
H32B	0.933784	0.043378	0.243139	0.039*
C33	0.8580 (3)	−0.1298 (3)	0.18232 (10)	0.0320 (6)
H33A	0.776254	−0.228237	0.182322	0.038*
H33B	0.974638	−0.141789	0.178384	0.038*
C34	0.8164 (3)	−0.0486 (3)	0.12775 (10)	0.0319 (6)
H34A	0.908077	0.043686	0.123919	0.038*
H34B	0.707375	−0.023895	0.134115	0.038*
C35	0.8002 (3)	−0.1378 (3)	0.06942 (9)	0.0317 (6)
H35A	0.709602	−0.230584	0.073611	0.038*
H35B	0.909714	−0.161648	0.063027	0.038*
C36	0.7566 (3)	−0.0591 (3)	0.01426 (9)	0.0321 (6)
H36A	0.648880	−0.032642	0.021052	0.039*
H36B	0.849030	0.032104	0.009195	0.039*
C37	0.7354 (3)	−0.1514 (3)	−0.04338 (10)	0.0332 (6)
H37A	0.843351	−0.177654	−0.050164	0.040*
H37B	0.643403	−0.242829	−0.038181	0.040*
C38	0.6913 (3)	−0.0740 (3)	−0.09865 (10)	0.0324 (6)
H38A	0.784213	0.016683	−0.104200	0.039*
H38B	0.584358	−0.046434	−0.091618	0.039*
C39	0.6675 (4)	−0.1669 (3)	−0.15610 (10)	0.0349 (6)
H39A	0.576900	−0.258829	−0.150162	0.042*
H39B	0.775603	−0.192197	−0.163757	0.042*
C40	0.6186 (4)	−0.0908 (3)	−0.21120 (10)	0.0377 (6)
H40A	0.513767	−0.060992	−0.202886	0.045*
H40B	0.712046	−0.001719	−0.218608	0.045*
C41	0.5864 (4)	−0.1877 (3)	−0.26715 (11)	0.0446 (7)
H41A	0.691687	−0.213281	−0.276828	0.054*
H41B	0.551884	−0.135694	−0.300897	0.054*
H41C	0.494847	−0.276608	−0.259900	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0246 (11)	0.0213 (10)	0.0288 (11)	0.0063 (10)	−0.0022 (8)	−0.0021 (7)
C2	0.0223 (13)	0.0218 (12)	0.0303 (12)	0.0063 (12)	−0.0024 (9)	−0.0013 (9)
C3	0.0206 (12)	0.0198 (12)	0.0301 (12)	0.0037 (11)	−0.0020 (9)	−0.0028 (9)
C4	0.0338 (14)	0.0253 (12)	0.0302 (13)	0.0125 (12)	0.0005 (10)	−0.0015 (9)
C5	0.0226 (12)	0.0220 (12)	0.0294 (12)	0.0078 (11)	−0.0016 (9)	−0.0044 (9)
N6	0.0388 (13)	0.0280 (11)	0.0280 (11)	0.0177 (11)	−0.0011 (9)	−0.0018 (8)
N7	0.0387 (13)	0.0265 (11)	0.0310 (11)	0.0174 (11)	0.0000 (9)	0.0016 (8)
C8	0.0282 (13)	0.0211 (12)	0.0253 (12)	0.0088 (12)	−0.0022 (9)	0.0027 (8)
O9	0.0286 (9)	0.0228 (8)	0.0245 (8)	0.0118 (8)	−0.0002 (6)	−0.0004 (6)
C10	0.0209 (12)	0.0223 (12)	0.0283 (12)	0.0076 (11)	−0.0012 (9)	−0.0022 (9)
C11	0.0253 (13)	0.0248 (12)	0.0237 (11)	0.0066 (12)	−0.0006 (9)	−0.0025 (8)
C12	0.0232 (13)	0.0227 (12)	0.0262 (12)	0.0060 (12)	−0.0029 (9)	0.0017 (9)
C13	0.0255 (13)	0.0190 (11)	0.0284 (12)	0.0080 (11)	−0.0009 (9)	−0.0025 (8)
C14	0.0234 (12)	0.0206 (12)	0.0227 (11)	0.0034 (11)	−0.0020 (8)	−0.0007 (8)
C15	0.0251 (13)	0.0201 (11)	0.0267 (11)	0.0067 (11)	−0.0032 (9)	0.0016 (8)
O16	0.0358 (10)	0.0304 (9)	0.0262 (8)	0.0192 (9)	0.0016 (7)	0.0043 (6)
C17	0.0313 (14)	0.0284 (13)	0.0277 (12)	0.0157 (12)	0.0000 (9)	−0.0006 (9)
C18	0.0315 (14)	0.0265 (12)	0.0325 (13)	0.0141 (12)	−0.0036 (10)	0.0026 (9)
C19	0.0366 (15)	0.0282 (13)	0.0290 (12)	0.0138 (13)	−0.0020 (10)	0.0016 (9)
C20	0.0360 (15)	0.0279 (13)	0.0311 (13)	0.0137 (13)	−0.0025 (10)	0.0020 (9)
C21	0.0402 (16)	0.0334 (14)	0.0299 (13)	0.0164 (14)	−0.0028 (10)	0.0006 (10)
C22	0.0392 (15)	0.0302 (13)	0.0291 (13)	0.0127 (13)	−0.0018 (10)	0.0006 (9)
C23	0.0391 (16)	0.0309 (14)	0.0318 (13)	0.0127 (14)	−0.0018 (11)	0.0012 (10)
C24	0.0382 (15)	0.0303 (14)	0.0279 (13)	0.0113 (13)	−0.0023 (10)	0.0005 (10)
C25	0.0386 (16)	0.0320 (14)	0.0303 (13)	0.0110 (14)	−0.0032 (10)	0.0006 (10)
C26	0.0367 (15)	0.0336 (14)	0.0323 (13)	0.0118 (13)	−0.0020 (11)	0.0024 (10)
C27	0.0414 (16)	0.0399 (15)	0.0299 (13)	0.0101 (15)	−0.0022 (11)	0.0006 (10)
C28	0.0494 (18)	0.0547 (18)	0.0323 (14)	0.0194 (16)	−0.0047 (12)	0.0015 (12)
O29	0.0394 (10)	0.0268 (9)	0.0226 (8)	0.0150 (9)	0.0000 (7)	0.0007 (6)
C30	0.0353 (14)	0.0278 (13)	0.0252 (12)	0.0127 (13)	−0.0026 (10)	0.0026 (9)
C31	0.0432 (16)	0.0324 (14)	0.0250 (12)	0.0151 (14)	0.0007 (10)	0.0007 (9)
C32	0.0447 (16)	0.0303 (13)	0.0267 (12)	0.0156 (13)	0.0006 (10)	0.0014 (9)
C33	0.0407 (16)	0.0318 (13)	0.0250 (12)	0.0130 (13)	−0.0006 (10)	0.0016 (9)
C34	0.0379 (15)	0.0336 (14)	0.0261 (12)	0.0132 (13)	0.0005 (10)	0.0013 (9)
C35	0.0371 (15)	0.0328 (14)	0.0261 (13)	0.0112 (13)	−0.0008 (10)	0.0001 (10)
C36	0.0382 (15)	0.0362 (14)	0.0241 (12)	0.0142 (14)	−0.0004 (10)	0.0004 (10)
C37	0.0393 (15)	0.0349 (14)	0.0268 (12)	0.0129 (14)	−0.0026 (10)	−0.0015 (10)
C38	0.0384 (15)	0.0344 (14)	0.0250 (12)	0.0115 (13)	−0.0024 (10)	−0.0008 (9)
C39	0.0401 (16)	0.0358 (14)	0.0294 (13)	0.0117 (14)	−0.0008 (11)	−0.0013 (10)
C40	0.0452 (17)	0.0406 (15)	0.0269 (13)	0.0115 (15)	−0.0023 (11)	−0.0022 (10)
C41	0.0508 (19)	0.0566 (18)	0.0275 (14)	0.0169 (17)	−0.0020 (12)	−0.0019 (12)

Geometric parameters (Å, º)

N1—C2	1.338 (3)	C25—C26	1.526 (3)
N1—C3^i	1.338 (3)	C25—H25A	0.9900
C2—C3	1.406 (3)	C25—H25B	0.9900
C2—C4	1.499 (3)	C26—C27	1.524 (3)
C3—C5	1.465 (3)	C26—H26A	0.9900
C4—H4A	0.9800	C26—H26B	0.9900
C4—H4B	0.9800	C27—C28	1.532 (3)
C4—H4C	0.9800	C27—H27A	0.9900
C5—N6	1.290 (3)	C27—H27B	0.9900
C5—O9	1.369 (2)	C28—H28A	0.9800
N6—N7	1.408 (2)	C28—H28B	0.9800
N7—C8	1.290 (3)	C28—H28C	0.9800
C8—O9	1.357 (2)	O29—C30	1.441 (2)
C8—C10	1.465 (3)	C30—C31	1.505 (3)
C10—C11	1.382 (3)	C30—H30A	0.9900
C10—C15	1.396 (3)	C30—H30B	0.9900
C11—C12	1.394 (3)	C31—C32	1.526 (3)
C11—H11	0.9500	C31—H31A	0.9900
C12—O16	1.362 (3)	C31—H31B	0.9900
C12—C13	1.380 (3)	C32—C33	1.523 (3)
C13—C14	1.395 (3)	C32—H32A	0.9900
C13—H13	0.9500	C32—H32B	0.9900
C14—O29	1.363 (3)	C33—C34	1.526 (3)
C14—C15	1.391 (3)	C33—H33A	0.9900
C15—H15	0.9500	C33—H33B	0.9900
O16—C17	1.437 (2)	C34—C35	1.527 (3)
C17—C18	1.513 (3)	C34—H34A	0.9900
C17—H17A	0.9900	C34—H34B	0.9900
C17—H17B	0.9900	C35—C36	1.528 (3)
C18—C19	1.525 (3)	C35—H35A	0.9900
C18—H18A	0.9900	C35—H35B	0.9900
C18—H18B	0.9900	C36—C37	1.527 (3)
C19—C20	1.530 (3)	C36—H36A	0.9900
C19—H19A	0.9900	C36—H36B	0.9900
C19—H19B	0.9900	C37—C38	1.525 (3)
C20—C21	1.532 (3)	C37—H37A	0.9900
C20—H20A	0.9900	C37—H37B	0.9900
C20—H20B	0.9900	C38—C39	1.525 (3)
C21—C22	1.527 (3)	C38—H38A	0.9900
C21—H21A	0.9900	C38—H38B	0.9900
C21—H21B	0.9900	C39—C40	1.529 (3)
C22—C23	1.527 (3)	C39—H39A	0.9900
C22—H22A	0.9900	C39—H39B	0.9900
C22—H22B	0.9900	C40—C41	1.516 (3)
C23—C24	1.534 (3)	C40—H40A	0.9900
C23—H23A	0.9900	C40—H40B	0.9900
C23—H23B	0.9900	C41—H41A	0.9800
C24—C25	1.527 (3)	C41—H41B	0.9800
C24—H24A	0.9900	C41—H41C	0.9800
C24—H24B	0.9900
C2—N1—C3^i	118.49 (19)	C24—C25—H25B	108.8
N1—C2—C3	118.7 (2)	H25A—C25—H25B	107.7
N1—C2—C4	116.83 (18)	C27—C26—C25	113.1 (2)
C3—C2—C4	124.49 (19)	C27—C26—H26A	109.0
N1^i—C3—C2	122.8 (2)	C25—C26—H26A	109.0
N1^i—C3—C5	114.69 (19)	C27—C26—H26B	109.0
C2—C3—C5	122.4 (2)	C25—C26—H26B	109.0
C2—C4—H4A	109.5	H26A—C26—H26B	107.8
C2—C4—H4B	109.5	C26—C27—C28	113.3 (2)
H4A—C4—H4B	109.5	C26—C27—H27A	108.9
C2—C4—H4C	109.5	C28—C27—H27A	108.9
H4A—C4—H4C	109.5	C26—C27—H27B	108.9
H4B—C4—H4C	109.5	C28—C27—H27B	108.9
N6—C5—O9	112.67 (18)	H27A—C27—H27B	107.7
N6—C5—C3	129.76 (19)	C27—C28—H28A	109.5
O9—C5—C3	117.52 (18)	C27—C28—H28B	109.5
C5—N6—N7	106.03 (17)	H28A—C28—H28B	109.5
C8—N7—N6	106.06 (17)	C27—C28—H28C	109.5
N7—C8—O9	113.02 (18)	H28A—C28—H28C	109.5
N7—C8—C10	128.27 (19)	H28B—C28—H28C	109.5
O9—C8—C10	118.69 (18)	C14—O29—C30	118.34 (16)
C8—O9—C5	102.21 (16)	O29—C30—C31	106.77 (17)
C11—C10—C15	121.71 (19)	O29—C30—H30A	110.4
C11—C10—C8	117.78 (19)	C31—C30—H30A	110.4
C15—C10—C8	120.48 (19)	O29—C30—H30B	110.4
C10—C11—C12	119.2 (2)	C31—C30—H30B	110.4
C10—C11—H11	120.4	H30A—C30—H30B	108.6
C12—C11—H11	120.4	C30—C31—C32	112.61 (19)
O16—C12—C13	125.20 (19)	C30—C31—H31A	109.1
O16—C12—C11	114.55 (19)	C32—C31—H31A	109.1
C13—C12—C11	120.25 (19)	C30—C31—H31B	109.1
C12—C13—C14	119.89 (19)	C32—C31—H31B	109.1
C12—C13—H13	120.1	H31A—C31—H31B	107.8
C14—C13—H13	120.1	C33—C32—C31	112.02 (19)
O29—C14—C15	123.95 (19)	C33—C32—H32A	109.2
O29—C14—C13	115.19 (18)	C31—C32—H32A	109.2
C15—C14—C13	120.8 (2)	C33—C32—H32B	109.2
C14—C15—C10	118.08 (19)	C31—C32—H32B	109.2
C14—C15—H15	121.0	H32A—C32—H32B	107.9
C10—C15—H15	121.0	C32—C33—C34	114.08 (19)
C12—O16—C17	118.96 (17)	C32—C33—H33A	108.7
O16—C17—C18	106.94 (17)	C34—C33—H33A	108.7
O16—C17—H17A	110.3	C32—C33—H33B	108.7
C18—C17—H17A	110.3	C34—C33—H33B	108.7
O16—C17—H17B	110.3	H33A—C33—H33B	107.6
C18—C17—H17B	110.3	C33—C34—C35	112.41 (19)
H17A—C17—H17B	108.6	C33—C34—H34A	109.1
C17—C18—C19	113.50 (19)	C35—C34—H34A	109.1
C17—C18—H18A	108.9	C33—C34—H34B	109.1
C19—C18—H18A	108.9	C35—C34—H34B	109.1
C17—C18—H18B	108.9	H34A—C34—H34B	107.9
C19—C18—H18B	108.9	C34—C35—C36	113.29 (19)
H18A—C18—H18B	107.7	C34—C35—H35A	108.9
C18—C19—C20	112.56 (19)	C36—C35—H35A	108.9
C18—C19—H19A	109.1	C34—C35—H35B	108.9
C20—C19—H19A	109.1	C36—C35—H35B	108.9
C18—C19—H19B	109.1	H35A—C35—H35B	107.7
C20—C19—H19B	109.1	C37—C36—C35	112.69 (19)
H19A—C19—H19B	107.8	C37—C36—H36A	109.1
C19—C20—C21	113.68 (19)	C35—C36—H36A	109.1
C19—C20—H20A	108.8	C37—C36—H36B	109.1
C21—C20—H20A	108.8	C35—C36—H36B	109.1
C19—C20—H20B	108.8	H36A—C36—H36B	107.8
C21—C20—H20B	108.8	C38—C37—C36	113.07 (19)
H20A—C20—H20B	107.7	C38—C37—H37A	109.0
C22—C21—C20	112.97 (19)	C36—C37—H37A	109.0
C22—C21—H21A	109.0	C38—C37—H37B	109.0
C20—C21—H21A	109.0	C36—C37—H37B	109.0
C22—C21—H21B	109.0	H37A—C37—H37B	107.8
C20—C21—H21B	109.0	C37—C38—C39	113.1 (2)
H21A—C21—H21B	107.8	C37—C38—H38A	109.0
C21—C22—C23	113.19 (19)	C39—C38—H38A	109.0
C21—C22—H22A	108.9	C37—C38—H38B	109.0
C23—C22—H22A	108.9	C39—C38—H38B	109.0
C21—C22—H22B	108.9	H38A—C38—H38B	107.8
C23—C22—H22B	108.9	C38—C39—C40	113.1 (2)
H22A—C22—H22B	107.8	C38—C39—H39A	109.0
C22—C23—C24	113.40 (19)	C40—C39—H39A	109.0
C22—C23—H23A	108.9	C38—C39—H39B	109.0
C24—C23—H23A	108.9	C40—C39—H39B	109.0
C22—C23—H23B	108.9	H39A—C39—H39B	107.8
C24—C23—H23B	108.9	C41—C40—C39	112.3 (2)
H23A—C23—H23B	107.7	C41—C40—H40A	109.1
C25—C24—C23	113.27 (19)	C39—C40—H40A	109.1
C25—C24—H24A	108.9	C41—C40—H40B	109.1
C23—C24—H24A	108.9	C39—C40—H40B	109.1
C25—C24—H24B	108.9	H40A—C40—H40B	107.9
C23—C24—H24B	108.9	C40—C41—H41A	109.5
H24A—C24—H24B	107.7	C40—C41—H41B	109.5
C26—C25—C24	113.68 (19)	H41A—C41—H41B	109.5
C26—C25—H25A	108.8	C40—C41—H41C	109.5
C24—C25—H25A	108.8	H41A—C41—H41C	109.5
C26—C25—H25B	108.8	H41B—C41—H41C	109.5
C3^i—N1—C2—C3	−0.3 (4)	O29—C14—C15—C10	−179.3 (2)
C3^i—N1—C2—C4	178.4 (2)	C13—C14—C15—C10	0.0 (4)
N1—C2—C3—N1^i	0.4 (4)	C11—C10—C15—C14	−1.0 (3)
C4—C2—C3—N1^i	−178.3 (2)	C8—C10—C15—C14	176.6 (2)
N1—C2—C3—C5	−176.6 (2)	C13—C12—O16—C17	15.8 (3)
C4—C2—C3—C5	4.8 (4)	C11—C12—O16—C17	−164.1 (2)
N1^i—C3—C5—N6	−177.5 (2)	C12—O16—C17—C18	176.2 (2)
C2—C3—C5—N6	−0.4 (4)	O16—C17—C18—C19	−55.3 (3)
N1^i—C3—C5—O9	−0.4 (3)	C17—C18—C19—C20	−173.5 (2)
C2—C3—C5—O9	176.7 (2)	C18—C19—C20—C21	−168.7 (2)
O9—C5—N6—N7	−0.7 (3)	C19—C20—C21—C22	−179.0 (2)
C3—C5—N6—N7	176.5 (2)	C20—C21—C22—C23	−178.1 (2)
C5—N6—N7—C8	0.2 (3)	C21—C22—C23—C24	179.7 (2)
N6—N7—C8—O9	0.4 (3)	C22—C23—C24—C25	−179.6 (2)
N6—N7—C8—C10	178.7 (2)	C23—C24—C25—C26	−179.2 (2)
N7—C8—O9—C5	−0.8 (3)	C24—C25—C26—C27	−179.9 (2)
C10—C8—O9—C5	−179.2 (2)	C25—C26—C27—C28	−179.9 (2)
N6—C5—O9—C8	0.9 (3)	C15—C14—O29—C30	−1.4 (3)
C3—C5—O9—C8	−176.6 (2)	C13—C14—O29—C30	179.3 (2)
N7—C8—C10—C11	−2.0 (4)	C14—O29—C30—C31	−177.9 (2)
O9—C8—C10—C11	176.2 (2)	O29—C30—C31—C32	178.1 (2)
N7—C8—C10—C15	−179.7 (2)	C30—C31—C32—C33	−166.6 (2)
O9—C8—C10—C15	−1.6 (4)	C31—C32—C33—C34	179.0 (2)
C15—C10—C11—C12	1.1 (4)	C32—C33—C34—C35	−171.7 (2)
C8—C10—C11—C12	−176.6 (2)	C33—C34—C35—C36	179.4 (2)
C10—C11—C12—O16	179.8 (2)	C34—C35—C36—C37	−178.2 (2)
C10—C11—C12—C13	−0.1 (4)	C35—C36—C37—C38	179.8 (2)
O16—C12—C13—C14	179.2 (2)	C36—C37—C38—C39	−179.2 (2)
C11—C12—C13—C14	−0.9 (4)	C37—C38—C39—C40	178.4 (2)
C12—C13—C14—O29	−179.7 (2)	C38—C39—C40—C41	−177.0 (2)
C12—C13—C14—C15	0.9 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.