Bis(4-dodecyl­oxyphen­yl)diazene oxide

The title compound, C₃₆H₅₈N₂O₃, also known as a liquid crystalline material, has a phase sequence of crystal–smectic C–isotropic liquid. The two benzene rings are nearly coplanar with the central NNO group, and each paraffin chain has an all-trans conformation. The mol­ecules form a tilted layer structure via inter­molecular π–π, C—H...O and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.117
• wR factor = 0.226
• Data-to-parameter ratio = 20.1

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.778     0.997
            Tmin(prime) and Tmax expected:      0.989     0.997
            RR(prime) =      0.787
            Please check that your absorption correction is appropriate.
RFACG01_ALERT_3_C  The value of the R factor is > 0.10
            R factor given   0.117
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.79
PLAT082_ALERT_2_C High R1 Value ..................................       0.12
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.91 Ratio
PLAT480_ALERT_4_C Long H...A H-Bond Reported H33    ..  O2      ..       2.71 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H34    ..  O1      ..       2.68 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7     ..  C2      ..       2.87 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC & Rigaku, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Bruno et al., 2002); software used to prepare material for publication: CrystalStructure.

Bis(4-dodecyloxyphenyl)diazene oxide

Crystal data

C36H58N2O3	Z = 2
Mr = 566.84	F(000) = 624.00
Triclinic, P1	Dx = 1.129 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.7107 Å
a = 7.514 (7) Å	Cell parameters from 2246 reflections
b = 8.853 (8) Å	θ = 3.2–27.5°
c = 25.21 (2) Å	µ = 0.07 mm^−1
α = 85.15 (2)°	T = 123 K
β = 89.36 (2)°	Platelet, yellow
γ = 86.19 (2)°	0.15 × 0.10 × 0.04 mm
V = 1667 (3) Å^3

Data collection

Rigaku Saturn diffractometer	4191 reflections with F^2 > 2σ(F^2)
Detector resolution: 7.31 pixels mm^-1	Rint = 0.077
ω scans	θmax = 27.6°
Absorption correction: multi-scan (Jacobson, 1998)	h = −9→9
Tmin = 0.778, Tmax = 0.997	k = −11→11
21767 measured reflections	l = −32→32
7497 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.117	w = 1/[σ^2(Fo^2) + (0.0282P)^2 + 2.294P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.226	(Δ/σ)max = 0.001
S = 1.21	Δρmax = 0.34 e Å^−3
7466 reflections	Δρmin = −0.27 e Å^−3
371 parameters

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Some low-angle reflections were excluded from the refinement, as they were probably obscured by the beam-stop. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
O1	0.4569 (3)	0.3543 (3)	0.59577 (9)	0.0322 (6)
O2	0.9474 (3)	0.0820 (2)	0.41994 (8)	0.0234 (5)
O3	0.3448 (3)	0.9648 (2)	0.71163 (8)	0.0253 (5)
N1	0.5773 (3)	0.4199 (3)	0.56857 (10)	0.0230 (6)
N2	0.6289 (3)	0.5535 (3)	0.57234 (10)	0.0227 (5)
C1	0.6727 (4)	0.3326 (3)	0.52910 (11)	0.0205 (6)
C2	0.6362 (4)	0.1819 (4)	0.52722 (12)	0.0247 (7)
C3	0.7259 (4)	0.0940 (3)	0.49113 (12)	0.0239 (7)
C4	0.8520 (4)	0.1583 (3)	0.45684 (11)	0.0212 (6)
C5	0.8871 (4)	0.3103 (3)	0.45916 (12)	0.0233 (6)
C6	0.7982 (4)	0.3979 (3)	0.49502 (12)	0.0225 (6)
C7	0.9061 (4)	−0.0721 (3)	0.41339 (12)	0.0220 (6)
C8	1.0249 (4)	−0.1281 (3)	0.36931 (12)	0.0234 (6)
C9	0.9932 (4)	−0.2912 (3)	0.35927 (12)	0.0233 (6)
C10	1.1169 (4)	−0.3552 (3)	0.31724 (11)	0.0222 (6)
C11	1.0645 (4)	−0.5093 (3)	0.30296 (12)	0.0229 (6)
C12	1.1808 (4)	−0.5837 (3)	0.26060 (12)	0.0222 (6)
C13	1.1088 (4)	−0.7325 (3)	0.24720 (12)	0.0224 (6)
C14	1.2138 (4)	−0.8141 (3)	0.20460 (12)	0.0238 (6)
C15	1.1304 (4)	−0.9612 (3)	0.19417 (12)	0.0251 (7)
C16	1.2235 (4)	−1.0506 (3)	0.15164 (12)	0.0260 (7)
C17	1.1349 (5)	−1.1966 (4)	0.14388 (13)	0.0314 (7)
C18	1.2251 (6)	−1.2903 (4)	0.1019 (2)	0.0443 (9)
C19	0.5449 (4)	0.6478 (3)	0.60922 (11)	0.0199 (6)
C20	0.3922 (4)	0.6250 (3)	0.64082 (12)	0.0225 (6)
C21	0.3305 (4)	0.7337 (3)	0.67359 (12)	0.0231 (6)
C22	0.4185 (4)	0.8666 (3)	0.67703 (11)	0.0216 (6)
C23	0.5681 (4)	0.8919 (3)	0.64572 (12)	0.0257 (7)
C24	0.6292 (4)	0.7836 (3)	0.61208 (12)	0.0230 (6)
C25	0.4299 (4)	1.1032 (3)	0.71761 (12)	0.0224 (6)
C26	0.3258 (4)	1.1834 (3)	0.75999 (12)	0.0246 (7)
C27	0.4001 (4)	1.3343 (3)	0.77066 (12)	0.0246 (7)
C28	0.2973 (4)	1.4125 (3)	0.81424 (12)	0.0257 (7)
C29	0.3678 (4)	1.5647 (3)	0.82565 (13)	0.0269 (7)
C30	0.2672 (4)	1.6409 (3)	0.87028 (12)	0.0271 (7)
C31	0.3395 (4)	1.7924 (3)	0.88079 (13)	0.0281 (7)
C32	0.2422 (4)	1.8728 (4)	0.92491 (12)	0.0273 (7)
C33	0.3211 (5)	2.0220 (4)	0.93469 (13)	0.0317 (7)
C34	0.2255 (5)	2.1093 (4)	0.97741 (13)	0.0334 (8)
C35	0.3074 (6)	2.2576 (4)	0.9855 (2)	0.0455 (10)
C36	0.2095 (7)	2.3494 (5)	1.0265 (2)	0.0578 (12)
H1	0.5516	0.1397	0.5502	0.030*
H2	0.7019	−0.0073	0.4898	0.029*
H3	0.9715	0.3530	0.4363	0.028*
H4	0.8218	0.4993	0.4964	0.027*
H5	0.7816	−0.0753	0.4040	0.026*
H6	0.9281	−0.1355	0.4462	0.026*
H7	1.1487	−0.1218	0.3789	0.028*
H8	1.0021	−0.0630	0.3368	0.028*
H9	0.8707	−0.2959	0.3481	0.028*
H10	1.0091	−0.3547	0.3924	0.028*
H11	1.1134	−0.2850	0.2855	0.027*
H12	1.2382	−0.3646	0.3304	0.027*
H13	0.9423	−0.4984	0.2905	0.027*
H14	1.0673	−0.5777	0.3351	0.027*
H15	1.1838	−0.5148	0.2286	0.027*
H16	1.3018	−0.6028	0.2737	0.027*
H17	0.9866	−0.7121	0.2353	0.027*
H18	1.1070	−0.8003	0.2795	0.027*
H19	1.2154	−0.7482	0.1719	0.029*
H20	1.3360	−0.8368	0.2162	0.029*
H21	1.1297	−1.0258	0.2272	0.030*
H22	1.0073	−0.9370	0.1837	0.030*
H23	1.2225	−0.9877	0.1182	0.031*
H24	1.3470	−1.0751	0.1617	0.031*
H25	1.0117	−1.1713	0.1338	0.038*
H26	1.1348	−1.2583	0.1776	0.038*
H27	1.2398	−1.2267	0.0696	0.053*
H28	1.1526	−1.3718	0.0952	0.053*
H29	1.3398	−1.3314	0.1146	0.053*
H30	0.3329	0.5365	0.6396	0.027*
H31	0.2281	0.7185	0.6939	0.028*
H32	0.6268	0.9807	0.6473	0.031*
H33	0.7288	0.8014	0.5908	0.028*
H34	0.4280	1.1665	0.6842	0.027*
H35	0.5530	1.0809	0.7284	0.027*
H36	0.3278	1.1176	0.7928	0.030*
H37	0.2026	1.2018	0.7489	0.030*
H38	0.5242	1.3163	0.7810	0.030*
H39	0.3955	1.4011	0.7381	0.030*
H40	0.3025	1.3453	0.8467	0.031*
H41	0.1731	1.4292	0.8039	0.031*
H42	0.4928	1.5485	0.8351	0.032*
H43	0.3598	1.6328	0.7934	0.032*
H44	0.1422	1.6575	0.8609	0.033*
H45	0.2755	1.5734	0.9027	0.033*
H46	0.4646	1.7752	0.8901	0.034*
H47	0.3321	1.8590	0.8482	0.034*
H48	0.1176	1.8926	0.9154	0.033*
H49	0.2480	1.8063	0.9576	0.033*
H50	0.3188	2.0863	0.9016	0.038*
H51	0.4449	2.0009	0.9449	0.038*
H52	0.1014	2.1306	0.9675	0.040*
H53	0.2288	2.0461	1.0108	0.040*
H54	0.3083	2.3188	0.9517	0.055*
H55	0.4302	2.2357	0.9966	0.055*
H56	0.0832	2.3442	1.0226	0.069*
H57	0.2395	2.4533	1.0212	0.069*
H58	0.2443	2.3085	1.0616	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0349 (12)	0.0269 (12)	0.0373 (13)	−0.0135 (10)	0.0146 (10)	−0.0098 (10)
O2	0.0262 (11)	0.0175 (11)	0.0279 (11)	−0.0070 (8)	0.0053 (9)	−0.0056 (9)
O3	0.0242 (11)	0.0216 (11)	0.0325 (12)	−0.0090 (9)	0.0061 (9)	−0.0111 (9)
N1	0.0203 (12)	0.0229 (13)	0.0262 (13)	−0.0058 (10)	0.0051 (10)	−0.0024 (10)
N2	0.0211 (12)	0.0210 (13)	0.0271 (13)	−0.0052 (10)	0.0025 (10)	−0.0053 (10)
C1	0.0185 (13)	0.020 (2)	0.024 (2)	−0.0022 (11)	−0.0002 (11)	−0.0059 (12)
C2	0.021 (1)	0.028 (2)	0.026 (2)	−0.0087 (12)	0.0008 (12)	−0.0028 (13)
C3	0.027 (2)	0.019 (2)	0.028 (2)	−0.0051 (12)	0.0010 (12)	−0.0065 (12)
C4	0.019 (1)	0.025 (2)	0.021 (1)	−0.0001 (12)	0.0005 (11)	−0.0082 (12)
C5	0.024 (2)	0.021 (2)	0.026 (2)	−0.0078 (12)	0.0036 (12)	−0.0038 (12)
C6	0.022 (1)	0.019 (2)	0.028 (2)	−0.0055 (12)	0.0001 (12)	−0.0047 (12)
C7	0.022 (1)	0.017 (1)	0.029 (2)	−0.0053 (11)	0.0006 (12)	−0.0043 (12)
C8	0.023 (1)	0.018 (2)	0.030 (2)	−0.0056 (12)	0.0008 (12)	−0.0052 (12)
C9	0.022 (1)	0.022 (2)	0.028 (2)	−0.0060 (12)	0.0017 (12)	−0.0088 (12)
C10	0.024 (1)	0.022 (2)	0.022 (2)	−0.0029 (12)	0.0011 (12)	−0.0060 (12)
C11	0.022 (1)	0.023 (2)	0.025 (2)	−0.0032 (12)	0.0046 (12)	−0.0063 (12)
C12	0.022 (1)	0.021 (2)	0.024 (2)	−0.0030 (12)	0.0034 (12)	−0.0050 (12)
C13	0.025 (2)	0.021 (2)	0.023 (2)	−0.0053 (12)	0.0027 (12)	−0.0057 (12)
C14	0.024 (2)	0.022 (2)	0.026 (2)	−0.0056 (12)	0.0039 (12)	−0.0060 (12)
C15	0.027 (2)	0.024 (2)	0.025 (2)	−0.0050 (13)	0.0035 (12)	−0.0071 (12)
C16	0.031 (2)	0.020 (2)	0.028 (2)	−0.0040 (13)	−0.0010 (13)	−0.0061 (12)
C17	0.041 (2)	0.024 (2)	0.030 (2)	−0.003 (1)	−0.001 (1)	−0.0091 (13)
C18	0.059 (3)	0.033 (2)	0.042 (2)	0.003 (2)	−0.003 (2)	−0.016 (2)
C19	0.024 (1)	0.016 (1)	0.020 (1)	−0.0002 (11)	−0.0014 (11)	−0.0046 (11)
C20	0.021 (1)	0.021 (2)	0.027 (2)	−0.0072 (12)	0.0025 (12)	−0.0068 (12)
C21	0.019 (1)	0.024 (2)	0.027 (2)	−0.0090 (12)	0.0010 (11)	−0.0027 (12)
C22	0.022 (1)	0.022 (2)	0.022 (2)	−0.0014 (12)	−0.0016 (11)	−0.0042 (12)
C23	0.025 (2)	0.021 (2)	0.032 (2)	−0.0069 (12)	0.0048 (13)	−0.0064 (13)
C24	0.019 (1)	0.023 (2)	0.027 (2)	−0.0063 (12)	0.0022 (11)	0.0000 (12)
C25	0.023 (1)	0.017 (2)	0.029 (2)	−0.0046 (12)	0.0026 (12)	−0.0069 (12)
C26	0.026 (2)	0.024 (2)	0.025 (2)	−0.0023 (12)	−0.0016 (12)	−0.0054 (12)
C27	0.025 (2)	0.020 (2)	0.030 (2)	−0.0046 (12)	0.0008 (12)	−0.0043 (12)
C28	0.031 (2)	0.021 (2)	0.027 (2)	−0.0064 (13)	0.0022 (13)	−0.0079 (12)
C29	0.032 (2)	0.018 (2)	0.032 (2)	−0.0047 (13)	0.0011 (13)	−0.0034 (12)
C30	0.033 (2)	0.023 (2)	0.026 (2)	−0.0043 (13)	0.0015 (13)	−0.0058 (13)
C31	0.032 (2)	0.021 (2)	0.032 (2)	−0.0044 (13)	0.0013 (13)	−0.0076 (13)
C32	0.031 (2)	0.026 (2)	0.026 (2)	0.0001 (13)	0.0023 (13)	−0.0080 (13)
C33	0.040 (2)	0.024 (2)	0.032 (2)	−0.003 (1)	0.001 (1)	−0.007 (1)
C34	0.042 (2)	0.030 (2)	0.029 (2)	0.003 (2)	−0.001 (1)	−0.009 (1)
C35	0.079 (3)	0.023 (2)	0.036 (2)	−0.002 (2)	0.001 (2)	−0.009 (2)
C36	0.087 (3)	0.037 (2)	0.051 (3)	0.008 (2)	−0.000 (2)	−0.019 (2)

Geometric parameters (Å, º)

O1—N1	1.270 (3)	C8—H8	0.9700
O2—C4	1.364 (3)	C9—H9	0.9700
O2—C7	1.442 (3)	C9—H10	0.9701
O3—C22	1.370 (4)	C10—H11	0.9701
O3—C25	1.439 (4)	C10—H12	0.9699
N1—N2	1.280 (4)	C11—H13	0.9700
N1—C1	1.464 (4)	C11—H14	0.9699
N2—C19	1.417 (4)	C12—H15	0.9699
C1—C2	1.384 (4)	C12—H16	0.9701
C1—C6	1.390 (4)	C13—H17	0.9700
C2—C3	1.387 (4)	C13—H18	0.9700
C3—C2	1.387 (4)	C14—H19	0.9700
C3—C4	1.392 (4)	C14—H20	0.9700
C4—C3	1.392 (4)	C15—H21	0.9698
C4—C5	1.395 (4)	C15—H22	0.9701
C5—C6	1.379 (4)	C16—H23	0.9699
C7—C8	1.513 (4)	C16—H24	0.9701
C8—C9	1.521 (4)	C17—H25	0.9700
C9—C10	1.522 (4)	C17—H26	0.9700
C10—C11	1.518 (4)	C18—H27	0.9599
C11—C12	1.536 (4)	C18—H28	0.9599
C12—C13	1.522 (4)	C18—H29	0.9601
C13—C14	1.528 (4)	C20—H30	0.9300
C14—C15	1.525 (4)	C21—H31	0.9299
C15—C16	1.522 (4)	C23—H32	0.9300
C16—C17	1.521 (5)	C24—H33	0.9300
C17—C18	1.524 (5)	C25—H34	0.9700
C19—C20	1.405 (4)	C25—H35	0.9700
C19—C24	1.403 (4)	C26—H36	0.9700
C20—C21	1.375 (4)	C26—H37	0.9700
C21—C22	1.396 (4)	C27—H38	0.9700
C22—C23	1.386 (4)	C27—H39	0.9701
C23—C24	1.386 (4)	C28—H40	0.9698
C25—C26	1.514 (4)	C28—H41	0.9700
C26—C27	1.527 (4)	C29—H42	0.9700
C27—C28	1.523 (4)	C29—H43	0.9701
C28—C29	1.531 (4)	C30—H44	0.9699
C29—C30	1.528 (4)	C30—H45	0.9700
C30—C31	1.525 (4)	C31—H46	0.9700
C31—C32	1.524 (4)	C31—H47	0.9700
C32—C33	1.523 (5)	C32—H48	0.9699
C33—C34	1.524 (5)	C32—H49	0.9700
C34—C35	1.516 (5)	C33—H50	0.9699
C35—C36	1.522 (6)	C33—H51	0.9701
C2—H1	0.9300	C34—H52	0.9700
C3—H2	0.9299	C34—H53	0.9699
C5—H3	0.9300	C35—H54	0.9699
C6—H4	0.9301	C35—H55	0.9700
C7—H5	0.9700	C36—H56	0.9600
C7—H6	0.9699	C36—H57	0.9600
C8—H7	0.9701	C36—H58	0.9600
O1···N2	2.289 (3)	C4···C20^i	3.456 (4)
O1···C1	2.333 (4)	C5···C3	2.410 (4)
O1···C2	2.693 (4)	C5···C20^i	3.286 (4)
O1···C6^i	3.523 (3)	C6···O1^i	3.523 (3)
O1···C19	2.772 (4)	C6···N1^i	3.491 (4)
O1···C20	2.750 (4)	C6···C3	2.790 (4)
O2···C3	2.438 (4)	C7···C3	2.828 (4)
O2···C3^ii	3.536 (3)	C7···C9	2.513 (4)
O2···C5	2.340 (4)	C8···C10	2.546 (4)
O2···C8	2.381 (4)	C9···C11	2.517 (4)
O2···C21^i	3.404 (3)	C10···C12	2.589 (4)
O2···C24^iii	3.532 (4)	C11···C13	2.522 (4)
O3···C21	2.341 (4)	C12···C14	2.574 (4)
O3···C23	2.442 (4)	C13···C15	2.514 (4)
O3···C26	2.369 (4)	C14···C16	2.573 (4)
N1···C2	2.441 (4)	C15···C17	2.527 (5)
N1···C6	2.486 (4)	C16···C18	2.554 (5)
N1···C6^i	3.491 (4)	C19···C21	2.407 (4)
N1···C19	2.336 (4)	C19···C22	2.803 (4)
N1···C20	2.952 (4)	C19···C23	2.437 (4)
N1···C24	3.535 (4)	C20···C4^i	3.456 (4)
N2···C1	2.322 (4)	C20···C5^i	3.286 (4)
N2···C1^i	3.476 (4)	C20···C22	2.416 (4)
N2···C2	3.567 (4)	C20···C23	2.795 (4)
N2···C6	2.735 (4)	C20···C24	2.408 (4)
N2···C20	2.552 (4)	C21···O2^i	3.404 (3)
N2···C24	2.345 (4)	C21···C23	2.404 (4)
C1···N2^i	3.476 (4)	C21···C24	2.752 (4)
C1···C3	2.400 (4)	C22···C24	2.391 (4)
C1···C4	2.767 (4)	C22···C25	2.414 (4)
C1···C5	2.387 (4)	C23···C25	2.852 (4)
C2···C4	2.403 (4)	C24···O2^iii	3.532 (4)
C2···C5	2.770 (4)	C25···C27	2.534 (4)
C2···C6	2.413 (4)	C26···C28	2.536 (4)
C3···O2	2.438 (4)	C27···C29	2.558 (4)
C3···O2^ii	3.536 (3)	C28···C30	2.560 (4)
C3···C1	2.400 (4)	C29···C31	2.540 (5)
C3···C5	2.410 (4)	C30···C32	2.562 (4)
C3···C6	2.790 (4)	C31···C33	2.534 (5)
C3···C7	2.828 (4)	C32···C34	2.565 (5)
C4···C6	2.411 (4)	C33···C35	2.533 (5)
C4···C7	2.404 (4)	C34···C36	2.544 (5)
O1—N1—N2	127.6 (3)	C13—C14—H20	109.4597
O1—N1—C1	117.0 (2)	H18—C13—H17	107.5102
O2—C4—C3	124.3 (3)	H19—C14—C15	109.4638
O2—C4—C5	116.0 (2)	H20—C14—C15	109.4650
C7—O2—C4	117.9 (2)	C14—C15—H21	108.4867
O2—C7—C8	107.3 (2)	C14—C15—H22	108.4806
O3—C22—C21	115.6 (2)	H20—C14—H19	108.0454
O3—C22—C23	124.8 (3)	H21—C15—C16	108.4770
C25—O3—C22	118.5 (2)	H22—C15—C16	108.4644
O3—C25—C26	106.6 (2)	C15—C16—H23	109.1431
C1—N1—N2	115.4 (2)	C15—C16—H24	109.1277
N1—N2—C19	119.9 (2)	H22—C15—H21	107.5119
N1—C1—C2	118.0 (2)	H23—C16—C17	109.1489
N1—C1—C6	121.1 (3)	H24—C16—C17	109.1457
N2—C19—C20	129.4 (3)	C16—C17—H25	108.7525
N2—C19—C24	112.5 (2)	C16—C17—H26	108.7508
C1—C2—C3	120.0 (3)	H24—C16—H23	107.8695
C6—C1—C2	120.9 (3)	H25—C17—C18	108.7585
C1—C6—C5	119.1 (3)	H26—C17—C18	108.7576
C2—C3—C4	119.6 (3)	C17—C18—H27	109.4721
C3—C4—C5	119.7 (3)	C17—C18—H28	109.4634
C4—C5—C6	120.7 (3)	C17—C18—H29	109.4594
C7—C8—C9	111.8 (2)	H26—C17—H25	107.6467
C8—C9—C10	113.6 (2)	H28—C18—H27	109.4816
C9—C10—C11	111.8 (2)	H29—C18—H27	109.4797
C10—C11—C12	116.0 (2)	H29—C18—H28	109.4712
C11—C12—C13	111.2 (2)	C19—C20—H30	120.0193
C12—C13—C14	115.2 (2)	C19—C24—H33	119.0983
C13—C14—C15	110.9 (2)	H30—C20—C21	120.0230
C14—C15—C16	115.2 (3)	C20—C21—H31	119.3307
C15—C16—C17	112.3 (3)	H31—C21—C22	119.3420
C16—C17—C18	114.0 (3)	C22—C23—H32	120.3781
C19—C20—C21	120.0 (3)	H32—C23—C24	120.3646
C24—C19—C20	118.0 (3)	C23—C24—H33	119.0917
C19—C24—C23	121.8 (3)	H34—C25—C26	110.3935
C20—C21—C22	121.3 (3)	H35—C25—C26	110.4027
C21—C22—C23	119.6 (3)	C25—C26—H36	109.0157
C22—C23—C24	119.3 (3)	C25—C26—H37	109.0242
C25—C26—C27	112.8 (2)	H35—C25—H34	108.6077
C26—C27—C28	112.5 (2)	H36—C26—C27	109.0152
C27—C28—C29	113.8 (3)	H37—C26—C27	109.0185
C28—C29—C30	113.6 (3)	C26—C27—H38	109.1000
C29—C30—C31	112.6 (3)	C26—C27—H39	109.0920
C30—C31—C32	114.3 (3)	H37—C26—H36	107.7953
C31—C32—C33	112.5 (3)	H38—C27—C28	109.0998
C32—C33—C34	114.7 (3)	H39—C27—C28	109.1089
C33—C34—C35	112.9 (3)	C27—C28—H40	108.7988
C34—C35—C36	113.7 (3)	C27—C28—H41	108.7985
O2—C7—H5	110.2477	H39—C27—H38	107.8435
O2—C7—H6	110.2514	H40—C28—C29	108.8119
O3—C25—H34	110.4056	H41—C28—C29	108.8054
O3—C25—H35	110.3980	C28—C29—H42	108.8378
C1—C2—H1	120.0074	C28—C29—H43	108.8424
C1—C6—H4	120.4625	H41—C28—H40	107.6817
H1—C2—C3	120.0118	H42—C29—C30	108.8440
C2—C3—H2	120.1772	H43—C29—C30	108.8344
H2—C3—C4	120.1857	C29—C30—H44	109.0669
C4—C5—H3	119.6279	C29—C30—H45	109.0630
H3—C5—C6	119.6298	H43—C29—H42	107.6875
C5—C6—H4	120.4843	H44—C30—C31	109.0661
H5—C7—C8	110.2449	H45—C30—C31	109.0653
H6—C7—C8	110.2462	C30—C31—H46	108.6732
C7—C8—H7	109.2552	C30—C31—H47	108.6745
C7—C8—H8	109.2629	H45—C30—H44	107.8278
H6—C7—H5	108.5223	H46—C31—C32	108.6744
H7—C8—C9	109.2657	H47—C31—C32	108.6737
H8—C8—C9	109.2588	C31—C32—H48	109.1071
C8—C9—H9	108.8568	C31—C32—H49	109.0990
C8—C9—H10	108.8559	H47—C31—H46	107.6004
H8—C8—H7	107.9371	H48—C32—C33	109.0950
H9—C9—C10	108.8564	H49—C32—C33	109.0940
H10—C9—C10	108.8490	C32—C33—H50	108.5927
C9—C10—H11	109.2480	C32—C33—H51	108.5919
C9—C10—H12	109.2626	H49—C32—H48	107.8307
H10—C9—H9	107.7048	H50—C33—C34	108.5878
H11—C10—C11	109.2480	H51—C33—C34	108.5769
H12—C10—C11	109.2475	C33—C34—H52	109.0005
C10—C11—H13	108.2851	C33—C34—H53	109.0120
C10—C11—H14	108.2874	H51—C33—H50	107.5641
H12—C10—H11	107.9210	H52—C34—C35	109.0041
H13—C11—C12	108.2784	H53—C34—C35	109.0111
H14—C11—C12	108.2902	C34—C35—H54	108.8239
C11—C12—H15	109.4027	C34—C35—H55	108.8176
C11—C12—H16	109.3899	H53—C34—H52	107.7944
H14—C11—H13	107.3979	H54—C35—C36	108.8172
H15—C12—C13	109.4063	H55—C35—C36	108.8238
H16—C12—C13	109.3979	C35—C36—H56	109.4735
C12—C13—H17	108.4765	C35—C36—H57	109.4680
C12—C13—H18	108.4854	C35—C36—H58	109.4660
H16—C12—H15	108.0163	H55—C35—H54	107.6848
H17—C13—C14	108.4658	H57—C36—H56	109.4728
H18—C13—C14	108.4668	H58—C36—H56	109.4743
C13—C14—H19	109.4580	H58—C36—H57	109.4727
C7—O2—C4—C3	4.6 (4)	C9—C10—C11—C12	179.8 (2)
C7—O2—C4—C5	−175.5 (2)	C10—C11—C12—C13	−176.5 (2)
C4—O2—C7—C8	178.1 (2)	C11—C12—C13—C14	179.0 (2)
C25—O3—C22—C21	179.3 (2)	C12—C13—C14—C15	−179.9 (2)
C25—O3—C22—C23	−1.9 (4)	C13—C14—C15—C16	179.1 (2)
C22—O3—C25—C26	−177.0 (2)	C14—C15—C16—C17	179.2 (2)
O1—N1—N2—C19	−2.0 (4)	C15—C16—C17—C18	−179.5 (3)
C1—N1—N2—C19	179.8 (2)	N2—C19—C20—C21	−178.7 (3)
O1—N1—C1—C2	−5.3 (4)	C24—C19—C20—C21	−0.5 (4)
O1—N1—C1—C6	175.7 (3)	N2—C19—C24—C23	179.9 (2)
N2—N1—C1—C2	173.1 (2)	C20—C19—C24—C23	1.4 (4)
N2—N1—C1—C6	−5.9 (4)	C19—C20—C21—C22	−1.1 (4)
N1—N2—C19—C20	−7.8 (4)	C20—C21—C22—O3	−179.2 (3)
N1—N2—C19—C24	173.9 (2)	C20—C21—C22—C23	1.9 (4)
N1—C1—C2—C3	−178.8 (3)	O3—C22—C23—C24	−179.8 (3)
C6—C1—C2—C3	0.2 (4)	C21—C22—C23—C24	−1.0 (4)
N1—C1—C6—C5	178.8 (3)	C22—C23—C24—C19	−0.7 (4)
C2—C1—C6—C5	−0.2 (4)	O3—C25—C26—C27	−179.6 (2)
C1—C2—C3—C4	−0.2 (4)	C25—C26—C27—C28	−178.7 (2)
C2—C3—C4—O2	−180.0 (2)	C26—C27—C28—C29	−179.6 (2)
C2—C3—C4—C5	0.1 (3)	C27—C28—C29—C30	−178.6 (2)
O2—C4—C5—C6	180.0 (3)	C28—C29—C30—C31	−179.9 (2)
C3—C4—C5—C6	−0.1 (3)	C29—C30—C31—C32	179.7 (2)
C4—C5—C6—C1	0.2 (4)	C30—C31—C32—C33	179.0 (3)
O2—C7—C8—C9	179.6 (2)	C31—C32—C33—C34	178.4 (3)
C7—C8—C9—C10	−176.9 (2)	C32—C33—C34—C35	−179.5 (3)
C8—C9—C10—C11	−172.1 (2)	C33—C34—C35—C36	177.8 (3)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y, −z+1; (iii) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C24—H33···O2^iii	0.93	2.71	3.532 (4)	148 (1)
C25—H34···O1^iv	0.97	2.68	3.648 (4)	173 (1)
C8—H7···C2^ii	0.97	2.87	3.646 (4)	137 (1)

Symmetry codes: (ii) −x+2, −y, −z+1; (iii) −x+2, −y+1, −z+1; (iv) x, y+1, z.