N-(3-Methyl­phenyl)-N,N-bis(4-methyl­phenyl)­amine

The title complex, C₂₁H₂₁N, crystallizes in space group P, with Z = 6. The N atom is sp²-hybridized. The geometry of each of the three independent mol­ecules is unremarkable. The interaction of the three mol­ecules is discussed.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.071
• wR factor = 0.245
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found





Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         36 Perc.
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C43    -   C47     ..       7.16 su

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C13    -   C14     ..       6.95 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C73    -   C77     ..       5.10 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C84    -   C87     ..       5.46 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C14
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C43
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C73
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C84
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C17
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C37
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C47
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C57
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C67
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C87
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C97
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C21 H21 N
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C21 H21 N
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              C21 H21 N

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

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

---

Computing details

Data collection: COLLECT (Nonius, 2001); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 2001); software used to prepare material for publication: SHELXTL/PC.

N-(3-Methylphenyl)-N,N-bis(4-methylphenyl)amine

Crystal data

C21H21N	Z = 6
Mr = 287.39	F(000) = 924
Triclinic, P1	Dx = 1.127 Mg m^−3
Hall symbol: -P 1	Melting point: 329.7 K
a = 11.1573 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.8063 (12) Å	Cell parameters from 10662 reflections
c = 16.8629 (13) Å	θ = 1.7–25.0°
α = 66.738 (3)°	µ = 0.07 mm^−1
β = 86.740 (4)°	T = 295 K
γ = 83.251 (4)°	Prism, colourless
V = 2541.4 (3) Å^3	0.28 × 0.20 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer	8908 independent reflections
Radiation source: fine-focus sealed tube	3216 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.074
φ scans, and ω scans with κ offsets	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = −13→13
Tmin = 0.985, Tmax = 0.995	k = −15→17
24267 measured reflections	l = −20→20

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.071	H-atom parameters constrained
wR(F^2) = 0.245	w = 1/[σ^2(Fo^2) + (0.118P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.93	(Δ/σ)max = 0.001
8908 reflections	Δρmax = 0.26 e Å^−3
596 parameters	Δρmin = −0.19 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0094 (16)

Special details

Experimental. melting point: 329.7 K

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
N10	−0.1101 (2)	0.0116 (2)	−0.2361 (2)	0.0727 (9)
C11	−0.1765 (3)	0.0207 (3)	−0.1657 (3)	0.0685 (10)
C12	−0.2892 (3)	0.0737 (3)	−0.1763 (3)	0.0738 (11)
H12A	−0.3213	0.1028	−0.2315	0.089*
C13	−0.3564 (4)	0.0857 (3)	−0.1097 (3)	0.0895 (13)
C14	−0.3074 (5)	0.0407 (4)	−0.0276 (4)	0.1166 (17)
H14A	−0.3509	0.0464	0.0192	0.140*
C15	−0.1954 (6)	−0.0120 (4)	−0.0148 (3)	0.1087 (16)
H15A	−0.1633	−0.0408	0.0404	0.130*
C16	−0.1290 (4)	−0.0226 (3)	−0.0841 (3)	0.0890 (13)
H16A	−0.0534	−0.0588	−0.0750	0.107*
C17	−0.4768 (4)	0.1459 (3)	−0.1235 (3)	0.1229 (18)
H17A	−0.5090	0.1448	−0.0691	0.184*
H17B	−0.5309	0.1188	−0.1483	0.184*
H17C	−0.4675	0.2129	−0.1618	0.184*
C21	−0.1645 (3)	0.0030 (3)	−0.3072 (2)	0.0629 (10)
C22	−0.1090 (3)	0.0371 (3)	−0.3871 (3)	0.0689 (10)
H22A	−0.0375	0.0661	−0.3942	0.083*
C23	−0.1585 (3)	0.0286 (3)	−0.4569 (2)	0.0723 (11)
H23A	−0.1196	0.0519	−0.5103	0.087*
C24	−0.2653 (3)	−0.0140 (3)	−0.4487 (3)	0.0698 (10)
C25	−0.3189 (3)	−0.0478 (3)	−0.3683 (3)	0.0716 (10)
H25A	−0.3906	−0.0767	−0.3611	0.086*
C26	−0.2700 (3)	−0.0406 (3)	−0.2979 (2)	0.0669 (10)
H26A	−0.3082	−0.0651	−0.2442	0.080*
C27	−0.3185 (4)	−0.0245 (3)	−0.5260 (3)	0.1009 (14)
H27A	−0.3915	−0.0560	−0.5084	0.151*
H27B	−0.2614	−0.0639	−0.5470	0.151*
H27C	−0.3360	0.0398	−0.5709	0.151*
C31	0.0190 (3)	0.0031 (3)	−0.2336 (2)	0.0664 (10)
C32	0.0873 (3)	−0.0791 (3)	−0.2375 (2)	0.0702 (10)
H32A	0.0489	−0.1297	−0.2414	0.084*
C33	0.2104 (3)	−0.0870 (3)	−0.2359 (2)	0.0735 (11)
H33A	0.2543	−0.1430	−0.2390	0.088*
C34	0.2714 (3)	−0.0144 (3)	−0.2297 (2)	0.0711 (11)
C35	0.2020 (3)	0.0681 (3)	−0.2263 (2)	0.0778 (11)
H35A	0.2405	0.1186	−0.2224	0.093*
C36	0.0779 (4)	0.0775 (3)	−0.2284 (2)	0.0795 (12)
H36A	0.0338	0.1339	−0.2264	0.095*
C37	0.4074 (3)	−0.0231 (3)	−0.2274 (3)	0.1002 (14)
H37A	0.4326	0.0345	−0.2231	0.150*
H37B	0.4404	−0.0287	−0.2794	0.150*
H37C	0.4358	−0.0808	−0.1784	0.150*
N70	−0.2895 (3)	−0.3414 (2)	−0.5772 (2)	0.0872 (11)
C71	−0.2112 (3)	−0.3772 (3)	−0.6301 (3)	0.0766 (11)
C72	−0.2370 (4)	−0.3488 (3)	−0.7160 (3)	0.0860 (12)
H72A	−0.3062	−0.3067	−0.7392	0.103*
C73	−0.1584 (4)	−0.3835 (3)	−0.7689 (3)	0.0889 (13)
C74	−0.0590 (4)	−0.4454 (3)	−0.7326 (3)	0.0978 (14)
H74A	−0.0060	−0.4673	−0.7674	0.117*
C75	−0.0341 (4)	−0.4767 (3)	−0.6478 (3)	0.1020 (15)
H75A	0.0334	−0.5209	−0.6244	0.122*
C76	−0.1103 (4)	−0.4421 (3)	−0.5964 (3)	0.0932 (14)
H76A	−0.0934	−0.4628	−0.5381	0.112*
C77	−0.1867 (5)	−0.3511 (4)	−0.8606 (3)	0.150 (2)
H77A	−0.1250	−0.3799	−0.8881	0.226*
H77B	−0.1904	−0.2804	−0.8879	0.226*
H77C	−0.2632	−0.3718	−0.8658	0.226*
C81	−0.4175 (3)	−0.3274 (3)	−0.5881 (2)	0.0721 (11)
C82	−0.4755 (4)	−0.3982 (3)	−0.6001 (3)	0.0869 (13)
H82A	−0.4308	−0.4547	−0.6016	0.104*
C83	−0.5976 (4)	−0.3865 (3)	−0.6099 (3)	0.0922 (13)
H83A	−0.6344	−0.4348	−0.6188	0.111*
C84	−0.6674 (3)	−0.3052 (3)	−0.6069 (2)	0.0793 (12)
C85	−0.6092 (4)	−0.2342 (3)	−0.5944 (2)	0.0801 (12)
H85A	−0.6542	−0.1785	−0.5916	0.096*
C86	−0.4852 (4)	−0.2450 (3)	−0.5862 (2)	0.0791 (11)
H86A	−0.4475	−0.1959	−0.5792	0.095*
C87	−0.8027 (3)	−0.2944 (3)	−0.6158 (3)	0.1127 (16)
H87A	−0.8264	−0.3506	−0.6235	0.169*
H87B	−0.8269	−0.2353	−0.6650	0.169*
H87C	−0.8408	−0.2902	−0.5647	0.169*
C91	−0.2380 (3)	−0.3180 (3)	−0.5127 (3)	0.0688 (10)
C92	−0.2903 (3)	−0.3430 (3)	−0.4321 (3)	0.0797 (12)
H92A	−0.3606	−0.3743	−0.4193	0.096*
C93	−0.2373 (4)	−0.3214 (3)	−0.3696 (3)	0.0803 (12)
H93A	−0.2733	−0.3384	−0.3152	0.096*
C94	−0.1331 (4)	−0.2754 (3)	−0.3865 (3)	0.0736 (11)
C95	−0.0829 (3)	−0.2512 (3)	−0.4678 (3)	0.0807 (12)
H95A	−0.0118	−0.2209	−0.4804	0.097*
C96	−0.1342 (3)	−0.2704 (3)	−0.5314 (3)	0.0791 (11)
H96A	−0.0993	−0.2516	−0.5862	0.095*
C97	−0.0744 (4)	−0.2537 (3)	−0.3180 (3)	0.0985 (14)
H97A	−0.1214	−0.2760	−0.2656	0.148*
H97B	−0.0701	−0.1838	−0.3375	0.148*
H97C	0.0056	−0.2875	−0.3074	0.148*
N40	−0.4928 (3)	0.3171 (2)	0.0820 (2)	0.0765 (9)
C41	−0.4312 (3)	0.3310 (3)	0.0027 (3)	0.0722 (11)
C42	−0.3160 (3)	0.2838 (3)	0.0020 (3)	0.0820 (12)
H42A	−0.2784	0.2429	0.0535	0.098*
C43	−0.2569 (4)	0.2984 (3)	−0.0775 (4)	0.0868 (13)
C44	−0.3143 (5)	0.3569 (4)	−0.1527 (3)	0.1050 (15)
H44A	−0.2750	0.3657	−0.2049	0.126*
C45	−0.4276 (5)	0.4028 (4)	−0.1533 (3)	0.1048 (15)
H45A	−0.4647	0.4429	−0.2053	0.126*
C46	−0.4868 (4)	0.3889 (3)	−0.0757 (3)	0.0826 (12)
H46A	−0.5649	0.4187	−0.0758	0.099*
C47	−0.1354 (4)	0.2483 (4)	−0.0795 (4)	0.141 (2)
H47A	−0.1083	0.2661	−0.1383	0.211*
H47B	−0.1379	0.1780	−0.0525	0.211*
H47C	−0.0806	0.2680	−0.0489	0.211*
C51	−0.6223 (3)	0.3259 (3)	0.0831 (2)	0.0687 (10)
C52	−0.6879 (3)	0.4054 (3)	0.0922 (3)	0.0781 (11)
H52A	−0.6481	0.4543	0.0980	0.094*
C53	−0.8124 (4)	0.4140 (3)	0.0928 (3)	0.0844 (12)
H53A	−0.8552	0.4681	0.1001	0.101*
C54	−0.8738 (4)	0.3452 (4)	0.0831 (3)	0.0835 (12)
C55	−0.8080 (4)	0.2655 (3)	0.0744 (3)	0.0881 (13)
H55A	−0.8485	0.2171	0.0685	0.106*
C56	−0.6825 (4)	0.2545 (3)	0.0742 (3)	0.0842 (12)
H56A	−0.6399	0.1997	0.0680	0.101*
C57	−1.0110 (3)	0.3541 (4)	0.0831 (3)	0.1207 (17)
H57A	−1.0424	0.4141	0.0897	0.181*
H57B	−1.0391	0.2986	0.1302	0.181*
H57C	−1.0381	0.3555	0.0296	0.181*
C61	−0.4362 (3)	0.3227 (3)	0.1531 (3)	0.0676 (10)
C62	−0.4840 (3)	0.2792 (3)	0.2344 (3)	0.0751 (11)
H62A	−0.5520	0.2457	0.2423	0.090*
C63	−0.4326 (4)	0.2846 (3)	0.3046 (3)	0.0827 (12)
H63A	−0.4674	0.2553	0.3590	0.099*
C64	−0.3303 (3)	0.3326 (3)	0.2961 (3)	0.0784 (11)
C65	−0.2831 (3)	0.3748 (3)	0.2150 (3)	0.0780 (11)
H65A	−0.2142	0.4072	0.2076	0.094*
C66	−0.3338 (3)	0.3712 (3)	0.1433 (3)	0.0738 (11)
H66A	−0.2994	0.4012	0.0889	0.089*
C67	−0.2750 (4)	0.3385 (4)	0.3739 (3)	0.1164 (16)
H67A	−0.2051	0.3741	0.3559	0.175*
H67B	−0.2519	0.2729	0.4152	0.175*
H67C	−0.3330	0.3722	0.3997	0.175*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N10	0.0574 (19)	0.107 (2)	0.063 (2)	0.0004 (16)	−0.0052 (16)	−0.0456 (19)
C11	0.074 (3)	0.079 (3)	0.056 (3)	−0.009 (2)	−0.001 (2)	−0.030 (2)
C12	0.076 (3)	0.083 (3)	0.069 (3)	−0.019 (2)	0.012 (2)	−0.036 (2)
C13	0.090 (3)	0.104 (4)	0.096 (4)	−0.029 (3)	0.025 (3)	−0.059 (3)
C14	0.134 (5)	0.133 (5)	0.113 (5)	−0.054 (4)	0.053 (4)	−0.076 (4)
C15	0.157 (5)	0.117 (4)	0.057 (3)	−0.037 (4)	0.002 (3)	−0.034 (3)
C16	0.104 (3)	0.091 (3)	0.076 (3)	−0.011 (2)	−0.008 (3)	−0.036 (3)
C17	0.085 (3)	0.146 (4)	0.182 (6)	−0.028 (3)	0.046 (3)	−0.113 (4)
C21	0.057 (2)	0.077 (3)	0.056 (3)	−0.0019 (19)	−0.003 (2)	−0.028 (2)
C22	0.058 (2)	0.081 (3)	0.068 (3)	−0.0076 (19)	0.002 (2)	−0.030 (2)
C23	0.067 (2)	0.093 (3)	0.050 (3)	−0.001 (2)	0.001 (2)	−0.024 (2)
C24	0.063 (2)	0.085 (3)	0.064 (3)	0.008 (2)	−0.010 (2)	−0.034 (2)
C25	0.060 (2)	0.086 (3)	0.075 (3)	−0.0116 (19)	−0.001 (2)	−0.038 (2)
C26	0.061 (2)	0.084 (3)	0.055 (3)	−0.0089 (19)	0.0051 (19)	−0.027 (2)
C27	0.093 (3)	0.144 (4)	0.078 (3)	−0.002 (3)	−0.020 (2)	−0.057 (3)
C31	0.059 (2)	0.084 (3)	0.060 (3)	0.000 (2)	−0.0106 (18)	−0.033 (2)
C32	0.064 (3)	0.071 (3)	0.076 (3)	0.000 (2)	−0.011 (2)	−0.030 (2)
C33	0.069 (3)	0.078 (3)	0.078 (3)	0.003 (2)	−0.011 (2)	−0.036 (2)
C34	0.065 (2)	0.089 (3)	0.062 (3)	−0.004 (2)	−0.0041 (19)	−0.032 (2)
C35	0.070 (3)	0.086 (3)	0.085 (3)	−0.017 (2)	−0.008 (2)	−0.038 (2)
C36	0.081 (3)	0.084 (3)	0.083 (3)	0.003 (2)	−0.011 (2)	−0.045 (2)
C37	0.062 (3)	0.129 (4)	0.118 (4)	−0.011 (2)	−0.001 (2)	−0.056 (3)
N70	0.064 (2)	0.124 (3)	0.097 (3)	0.0081 (19)	−0.0118 (19)	−0.071 (2)
C71	0.077 (3)	0.094 (3)	0.069 (3)	−0.003 (2)	−0.009 (2)	−0.042 (2)
C72	0.087 (3)	0.090 (3)	0.085 (3)	−0.011 (2)	−0.009 (3)	−0.037 (3)
C73	0.101 (3)	0.108 (3)	0.066 (3)	−0.027 (3)	0.002 (3)	−0.039 (3)
C74	0.090 (3)	0.119 (4)	0.094 (4)	−0.009 (3)	0.007 (3)	−0.053 (3)
C75	0.095 (3)	0.114 (4)	0.110 (4)	0.009 (3)	−0.009 (3)	−0.062 (3)
C76	0.079 (3)	0.118 (4)	0.096 (4)	0.018 (3)	−0.020 (3)	−0.061 (3)
C77	0.165 (5)	0.184 (6)	0.100 (5)	−0.034 (4)	−0.011 (4)	−0.048 (4)
C81	0.067 (3)	0.084 (3)	0.068 (3)	−0.003 (2)	−0.0057 (19)	−0.033 (2)
C82	0.080 (3)	0.079 (3)	0.104 (4)	0.004 (2)	−0.018 (2)	−0.040 (3)
C83	0.090 (3)	0.080 (3)	0.106 (4)	−0.012 (3)	−0.013 (3)	−0.035 (3)
C84	0.060 (2)	0.099 (3)	0.073 (3)	−0.010 (2)	−0.007 (2)	−0.027 (3)
C85	0.074 (3)	0.085 (3)	0.076 (3)	0.010 (2)	−0.011 (2)	−0.030 (2)
C86	0.075 (3)	0.081 (3)	0.083 (3)	−0.001 (2)	−0.009 (2)	−0.034 (2)
C87	0.082 (3)	0.129 (4)	0.130 (4)	−0.015 (3)	0.003 (3)	−0.054 (3)
C91	0.061 (2)	0.083 (3)	0.071 (3)	0.005 (2)	−0.006 (2)	−0.042 (2)
C92	0.068 (2)	0.091 (3)	0.087 (3)	−0.002 (2)	0.000 (2)	−0.044 (3)
C93	0.077 (3)	0.095 (3)	0.067 (3)	0.007 (2)	0.003 (2)	−0.034 (2)
C94	0.075 (3)	0.077 (3)	0.073 (3)	0.007 (2)	−0.013 (2)	−0.036 (2)
C95	0.076 (3)	0.083 (3)	0.086 (3)	−0.010 (2)	−0.006 (3)	−0.035 (3)
C96	0.076 (3)	0.097 (3)	0.066 (3)	−0.007 (2)	−0.003 (2)	−0.035 (2)
C97	0.106 (3)	0.115 (3)	0.087 (3)	−0.001 (3)	−0.022 (3)	−0.053 (3)
N40	0.056 (2)	0.108 (3)	0.071 (2)	−0.0129 (17)	0.0049 (17)	−0.040 (2)
C41	0.067 (3)	0.075 (3)	0.081 (3)	−0.016 (2)	0.006 (2)	−0.036 (3)
C42	0.066 (3)	0.090 (3)	0.094 (4)	−0.013 (2)	0.006 (2)	−0.039 (3)
C43	0.066 (3)	0.102 (3)	0.111 (4)	−0.021 (2)	0.025 (3)	−0.062 (3)
C44	0.125 (4)	0.126 (4)	0.077 (4)	−0.040 (3)	0.018 (3)	−0.048 (3)
C45	0.110 (4)	0.114 (4)	0.096 (4)	−0.031 (3)	0.015 (3)	−0.044 (3)
C46	0.079 (3)	0.084 (3)	0.088 (4)	−0.013 (2)	0.002 (3)	−0.037 (3)
C47	0.104 (4)	0.174 (5)	0.181 (6)	−0.030 (4)	0.029 (4)	−0.109 (5)
C51	0.061 (2)	0.079 (3)	0.067 (3)	−0.014 (2)	0.0003 (19)	−0.028 (2)
C52	0.067 (3)	0.081 (3)	0.094 (3)	−0.013 (2)	0.001 (2)	−0.041 (2)
C53	0.066 (3)	0.093 (3)	0.089 (3)	−0.007 (2)	−0.003 (2)	−0.030 (3)
C54	0.063 (3)	0.106 (4)	0.067 (3)	−0.013 (3)	−0.001 (2)	−0.017 (3)
C55	0.083 (3)	0.095 (3)	0.087 (3)	−0.036 (3)	−0.007 (2)	−0.028 (3)
C56	0.087 (3)	0.082 (3)	0.085 (3)	−0.012 (2)	−0.005 (2)	−0.034 (2)
C57	0.065 (3)	0.159 (5)	0.116 (4)	−0.016 (3)	−0.008 (3)	−0.029 (3)
C61	0.053 (2)	0.078 (3)	0.069 (3)	−0.0018 (19)	0.002 (2)	−0.027 (2)
C62	0.061 (2)	0.089 (3)	0.072 (3)	−0.012 (2)	0.011 (2)	−0.028 (3)
C63	0.075 (3)	0.094 (3)	0.069 (3)	0.002 (2)	0.009 (2)	−0.025 (2)
C64	0.067 (3)	0.102 (3)	0.071 (3)	−0.002 (2)	−0.002 (2)	−0.040 (3)
C65	0.061 (2)	0.098 (3)	0.079 (3)	−0.012 (2)	0.004 (2)	−0.039 (3)
C66	0.065 (2)	0.081 (3)	0.070 (3)	−0.007 (2)	−0.001 (2)	−0.024 (2)
C67	0.099 (3)	0.178 (5)	0.085 (4)	−0.008 (3)	−0.010 (3)	−0.066 (3)

Geometric parameters (Å, º)

N10—C11	1.407 (4)	C84—C85	1.386 (5)
N10—C21	1.430 (4)	C84—C87	1.509 (5)
N10—C31	1.433 (4)	C85—C86	1.383 (5)
C11—C16	1.376 (5)	C85—H85A	0.9300
C11—C12	1.383 (5)	C86—H86A	0.9300
C12—C13	1.372 (5)	C87—H87A	0.9600
C12—H12A	0.9300	C87—H87B	0.9600
C13—C14	1.391 (6)	C87—H87C	0.9600
C13—C17	1.498 (5)	C91—C92	1.373 (5)
C14—C15	1.373 (6)	C91—C96	1.382 (5)
C14—H14A	0.9300	C92—C93	1.395 (5)
C15—C16	1.400 (6)	C92—H92A	0.9300
C15—H15A	0.9300	C93—C94	1.376 (5)
C16—H16A	0.9300	C93—H93A	0.9300
C17—H17A	0.9600	C94—C95	1.376 (5)
C17—H17B	0.9600	C94—C97	1.515 (5)
C17—H17C	0.9600	C95—C96	1.381 (5)
C21—C22	1.377 (5)	C95—H95A	0.9300
C21—C26	1.380 (4)	C96—H96A	0.9300
C22—C23	1.383 (4)	C97—H97A	0.9600
C22—H22A	0.9300	C97—H97B	0.9600
C23—C24	1.387 (5)	C97—H97C	0.9600
C23—H23A	0.9300	N40—C41	1.419 (5)
C24—C25	1.374 (5)	N40—C61	1.420 (4)
C24—C27	1.532 (5)	N40—C51	1.435 (4)
C25—C26	1.381 (4)	C41—C42	1.391 (5)
C25—H25A	0.9300	C41—C46	1.393 (5)
C26—H26A	0.9300	C42—C43	1.408 (5)
C27—H27A	0.9600	C42—H42A	0.9300
C27—H27B	0.9600	C43—C44	1.364 (6)
C27—H27C	0.9600	C43—C47	1.473 (6)
C31—C36	1.380 (5)	C44—C45	1.361 (6)
C31—C32	1.381 (4)	C44—H44A	0.9300
C32—C33	1.366 (4)	C45—C46	1.383 (6)
C32—H32A	0.9300	C45—H45A	0.9300
C33—C34	1.378 (5)	C46—H46A	0.9300
C33—H33A	0.9300	C47—H47A	0.9600
C34—C35	1.387 (5)	C47—H47B	0.9600
C34—C37	1.510 (5)	C47—H47C	0.9600
C35—C36	1.376 (5)	C51—C52	1.368 (5)
C35—H35A	0.9300	C51—C56	1.377 (5)
C36—H36A	0.9300	C52—C53	1.380 (5)
C37—H37A	0.9600	C52—H52A	0.9300
C37—H37B	0.9600	C53—C54	1.358 (5)
C37—H37C	0.9600	C53—H53A	0.9300
N70—C71	1.421 (4)	C54—C55	1.369 (5)
N70—C81	1.430 (4)	C54—C57	1.521 (5)
N70—C91	1.431 (4)	C55—C56	1.390 (5)
C71—C72	1.376 (5)	C55—H55A	0.9300
C71—C76	1.378 (5)	C56—H56A	0.9300
C72—C73	1.413 (6)	C57—H57A	0.9600
C72—H72A	0.9300	C57—H57B	0.9600
C73—C74	1.356 (5)	C57—H57C	0.9600
C73—C77	1.469 (6)	C61—C62	1.371 (5)
C74—C75	1.353 (6)	C61—C66	1.388 (5)
C74—H74A	0.9300	C62—C63	1.377 (5)
C75—C76	1.378 (5)	C62—H62A	0.9300
C75—H75A	0.9300	C63—C64	1.386 (5)
C76—H76A	0.9300	C63—H63A	0.9300
C77—H77A	0.9600	C64—C65	1.362 (5)
C77—H77B	0.9600	C64—C67	1.519 (5)
C77—H77C	0.9600	C65—C66	1.386 (5)
C81—C86	1.368 (5)	C65—H65A	0.9300
C81—C82	1.379 (5)	C66—H66A	0.9300
C82—C83	1.364 (5)	C67—H67A	0.9600
C82—H82A	0.9300	C67—H67B	0.9600
C83—C84	1.372 (5)	C67—H67C	0.9600
C83—H83A	0.9300
C11—N10—C21	123.3 (3)	C85—C84—C87	121.4 (4)
C11—N10—C31	118.5 (3)	C86—C85—C84	120.9 (4)
C21—N10—C31	118.1 (3)	C86—C85—H85A	119.6
C16—C11—C12	118.4 (4)	C84—C85—H85A	119.6
C16—C11—N10	120.0 (4)	C81—C86—C85	120.6 (4)
C12—C11—N10	121.5 (3)	C81—C86—H86A	119.7
C13—C12—C11	123.5 (4)	C85—C86—H86A	119.7
C13—C12—H12A	118.3	C84—C87—H87A	109.5
C11—C12—H12A	118.3	C84—C87—H87B	109.5
C12—C13—C14	117.3 (4)	H87A—C87—H87B	109.5
C12—C13—C17	122.4 (5)	C84—C87—H87C	109.5
C14—C13—C17	120.3 (5)	H87A—C87—H87C	109.5
C15—C14—C13	120.7 (5)	H87B—C87—H87C	109.5
C15—C14—H14A	119.6	C92—C91—C96	119.6 (3)
C13—C14—H14A	119.6	C92—C91—N70	120.6 (4)
C14—C15—C16	120.6 (5)	C96—C91—N70	119.8 (4)
C14—C15—H15A	119.7	C91—C92—C93	119.7 (4)
C16—C15—H15A	119.7	C91—C92—H92A	120.1
C11—C16—C15	119.5 (4)	C93—C92—H92A	120.1
C11—C16—H16A	120.3	C94—C93—C92	121.5 (4)
C15—C16—H16A	120.3	C94—C93—H93A	119.3
C13—C17—H17A	109.5	C92—C93—H93A	119.3
C13—C17—H17B	109.5	C93—C94—C95	117.4 (4)
H17A—C17—H17B	109.5	C93—C94—C97	121.4 (4)
C13—C17—H17C	109.5	C95—C94—C97	121.1 (4)
H17A—C17—H17C	109.5	C94—C95—C96	122.3 (4)
H17B—C17—H17C	109.5	C94—C95—H95A	118.8
C22—C21—C26	118.7 (3)	C96—C95—H95A	118.8
C22—C21—N10	119.3 (3)	C95—C96—C91	119.4 (4)
C26—C21—N10	122.0 (4)	C95—C96—H96A	120.3
C21—C22—C23	120.7 (3)	C91—C96—H96A	120.3
C21—C22—H22A	119.7	C94—C97—H97A	109.5
C23—C22—H22A	119.7	C94—C97—H97B	109.5
C22—C23—C24	121.2 (4)	H97A—C97—H97B	109.5
C22—C23—H23A	119.4	C94—C97—H97C	109.5
C24—C23—H23A	119.4	H97A—C97—H97C	109.5
C25—C24—C23	117.2 (3)	H97B—C97—H97C	109.5
C25—C24—C27	122.0 (4)	C41—N40—C61	122.3 (3)
C23—C24—C27	120.9 (4)	C41—N40—C51	118.5 (3)
C24—C25—C26	122.3 (3)	C61—N40—C51	116.8 (3)
C24—C25—H25A	118.8	C42—C41—C46	118.9 (4)
C26—C25—H25A	118.8	C42—C41—N40	120.4 (4)
C21—C26—C25	120.0 (4)	C46—C41—N40	120.7 (4)
C21—C26—H26A	120.0	C41—C42—C43	119.4 (4)
C25—C26—H26A	120.0	C41—C42—H42A	120.3
C24—C27—H27A	109.5	C43—C42—H42A	120.3
C24—C27—H27B	109.5	C44—C43—C42	119.6 (4)
H27A—C27—H27B	109.5	C44—C43—C47	120.3 (5)
C24—C27—H27C	109.5	C42—C43—C47	120.1 (5)
H27A—C27—H27C	109.5	C45—C44—C43	121.9 (5)
H27B—C27—H27C	109.5	C45—C44—H44A	119.1
C36—C31—C32	118.5 (3)	C43—C44—H44A	119.1
C36—C31—N10	120.8 (3)	C44—C45—C46	119.1 (5)
C32—C31—N10	120.7 (3)	C44—C45—H45A	120.4
C33—C32—C31	120.8 (3)	C46—C45—H45A	120.4
C33—C32—H32A	119.6	C45—C46—C41	121.1 (4)
C31—C32—H32A	119.6	C45—C46—H46A	119.5
C32—C33—C34	121.8 (4)	C41—C46—H46A	119.5
C32—C33—H33A	119.1	C43—C47—H47A	109.5
C34—C33—H33A	119.1	C43—C47—H47B	109.5
C33—C34—C35	116.9 (3)	H47A—C47—H47B	109.5
C33—C34—C37	121.9 (4)	C43—C47—H47C	109.5
C35—C34—C37	121.1 (4)	H47A—C47—H47C	109.5
C36—C35—C34	122.0 (3)	H47B—C47—H47C	109.5
C36—C35—H35A	119.0	C52—C51—C56	118.9 (3)
C34—C35—H35A	119.0	C52—C51—N40	120.8 (3)
C35—C36—C31	119.9 (4)	C56—C51—N40	120.2 (4)
C35—C36—H36A	120.0	C51—C52—C53	120.7 (4)
C31—C36—H36A	120.0	C51—C52—H52A	119.6
C34—C37—H37A	109.5	C53—C52—H52A	119.6
C34—C37—H37B	109.5	C54—C53—C52	121.4 (4)
H37A—C37—H37B	109.5	C54—C53—H53A	119.3
C34—C37—H37C	109.5	C52—C53—H53A	119.3
H37A—C37—H37C	109.5	C53—C54—C55	117.7 (4)
H37B—C37—H37C	109.5	C53—C54—C57	121.9 (5)
C71—N70—C81	121.2 (3)	C55—C54—C57	120.4 (4)
C71—N70—C91	118.7 (3)	C54—C55—C56	122.1 (4)
C81—N70—C91	120.1 (3)	C54—C55—H55A	119.0
C72—C71—C76	119.1 (4)	C56—C55—H55A	119.0
C72—C71—N70	120.0 (4)	C51—C56—C55	119.1 (4)
C76—C71—N70	120.9 (4)	C51—C56—H56A	120.5
C71—C72—C73	119.9 (4)	C55—C56—H56A	120.5
C71—C72—H72A	120.0	C54—C57—H57A	109.5
C73—C72—H72A	120.0	C54—C57—H57B	109.5
C74—C73—C72	118.4 (4)	H57A—C57—H57B	109.5
C74—C73—C77	122.5 (5)	C54—C57—H57C	109.5
C72—C73—C77	119.1 (5)	H57A—C57—H57C	109.5
C75—C74—C73	122.5 (4)	H57B—C57—H57C	109.5
C75—C74—H74A	118.7	C62—C61—C66	118.3 (4)
C73—C74—H74A	118.7	C62—C61—N40	119.4 (3)
C74—C75—C76	119.0 (4)	C66—C61—N40	122.3 (4)
C74—C75—H75A	120.5	C61—C62—C63	120.9 (4)
C76—C75—H75A	120.5	C61—C62—H62A	119.5
C71—C76—C75	121.0 (4)	C63—C62—H62A	119.5
C71—C76—H76A	119.5	C62—C63—C64	121.5 (4)
C75—C76—H76A	119.5	C62—C63—H63A	119.2
C73—C77—H77A	109.5	C64—C63—H63A	119.2
C73—C77—H77B	109.5	C65—C64—C63	117.0 (4)
H77A—C77—H77B	109.5	C65—C64—C67	121.9 (4)
C73—C77—H77C	109.5	C63—C64—C67	121.0 (4)
H77A—C77—H77C	109.5	C64—C65—C66	122.5 (4)
H77B—C77—H77C	109.5	C64—C65—H65A	118.8
C86—C81—C82	118.5 (4)	C66—C65—H65A	118.8
C86—C81—N70	121.4 (4)	C65—C66—C61	119.7 (4)
C82—C81—N70	120.1 (4)	C65—C66—H66A	120.1
C83—C82—C81	120.8 (4)	C61—C66—H66A	120.1
C83—C82—H82A	119.6	C64—C67—H67A	109.5
C81—C82—H82A	119.6	C64—C67—H67B	109.5
C82—C83—C84	121.7 (4)	H67A—C67—H67B	109.5
C82—C83—H83A	119.2	C64—C67—H67C	109.5
C84—C83—H83A	119.2	H67A—C67—H67C	109.5
C83—C84—C85	117.6 (4)	H67B—C67—H67C	109.5
C83—C84—C87	121.0 (4)
C21—N10—C11—C16	144.6 (4)	C82—C83—C84—C85	0.7 (6)
C31—N10—C11—C16	−30.6 (5)	C82—C83—C84—C87	−178.6 (4)
C21—N10—C11—C12	−36.1 (5)	C83—C84—C85—C86	0.5 (6)
C31—N10—C11—C12	148.7 (3)	C87—C84—C85—C86	179.9 (4)
C16—C11—C12—C13	0.2 (6)	C82—C81—C86—C85	1.3 (6)
N10—C11—C12—C13	−179.1 (4)	N70—C81—C86—C85	−178.1 (4)
C11—C12—C13—C14	−0.7 (6)	C84—C85—C86—C81	−1.5 (6)
C11—C12—C13—C17	178.2 (3)	C71—N70—C91—C92	−138.7 (4)
C12—C13—C14—C15	1.0 (7)	C81—N70—C91—C92	42.0 (5)
C17—C13—C14—C15	−177.9 (4)	C71—N70—C91—C96	40.8 (5)
C13—C14—C15—C16	−0.9 (7)	C81—N70—C91—C96	−138.5 (4)
C12—C11—C16—C15	−0.1 (6)	C96—C91—C92—C93	−0.8 (5)
N10—C11—C16—C15	179.2 (4)	N70—C91—C92—C93	178.7 (3)
C14—C15—C16—C11	0.4 (7)	C91—C92—C93—C94	−0.1 (5)
C11—N10—C21—C22	151.5 (3)	C92—C93—C94—C95	0.1 (5)
C31—N10—C21—C22	−33.3 (5)	C92—C93—C94—C97	−178.8 (3)
C11—N10—C21—C26	−30.0 (5)	C93—C94—C95—C96	0.9 (6)
C31—N10—C21—C26	145.3 (3)	C97—C94—C95—C96	179.7 (3)
C26—C21—C22—C23	0.5 (5)	C94—C95—C96—C91	−1.8 (6)
N10—C21—C22—C23	179.1 (3)	C92—C91—C96—C95	1.7 (5)
C21—C22—C23—C24	0.2 (5)	N70—C91—C96—C95	−177.8 (3)
C22—C23—C24—C25	−0.4 (5)	C61—N40—C41—C42	46.6 (5)
C22—C23—C24—C27	−179.1 (3)	C51—N40—C41—C42	−151.6 (3)
C23—C24—C25—C26	−0.1 (5)	C61—N40—C41—C46	−136.0 (4)
C27—C24—C25—C26	178.5 (3)	C51—N40—C41—C46	25.8 (5)
C22—C21—C26—C25	−1.0 (5)	C46—C41—C42—C43	2.3 (5)
N10—C21—C26—C25	−179.6 (3)	N40—C41—C42—C43	179.8 (3)
C24—C25—C26—C21	0.8 (5)	C41—C42—C43—C44	−1.4 (6)
C11—N10—C31—C36	−60.8 (5)	C41—C42—C43—C47	−179.5 (4)
C21—N10—C31—C36	123.7 (4)	C42—C43—C44—C45	0.6 (7)
C11—N10—C31—C32	120.1 (4)	C47—C43—C44—C45	178.7 (4)
C21—N10—C31—C32	−55.3 (5)	C43—C44—C45—C46	−0.7 (7)
C36—C31—C32—C33	0.4 (5)	C44—C45—C46—C41	1.6 (6)
N10—C31—C32—C33	179.4 (3)	C42—C41—C46—C45	−2.4 (6)
C31—C32—C33—C34	0.4 (6)	N40—C41—C46—C45	−179.9 (3)
C32—C33—C34—C35	−0.7 (6)	C41—N40—C51—C52	−108.3 (4)
C32—C33—C34—C37	179.7 (4)	C61—N40—C51—C52	54.5 (5)
C33—C34—C35—C36	0.3 (6)	C41—N40—C51—C56	71.0 (5)
C37—C34—C35—C36	179.9 (4)	C61—N40—C51—C56	−126.2 (4)
C34—C35—C36—C31	0.4 (6)	C56—C51—C52—C53	0.3 (6)
C32—C31—C36—C35	−0.8 (6)	N40—C51—C52—C53	179.7 (4)
N10—C31—C36—C35	−179.9 (3)	C51—C52—C53—C54	−1.1 (6)
C81—N70—C71—C72	36.7 (6)	C52—C53—C54—C55	1.4 (6)
C91—N70—C71—C72	−142.5 (4)	C52—C53—C54—C57	−179.6 (4)
C81—N70—C71—C76	−141.9 (4)	C53—C54—C55—C56	−0.9 (6)
C91—N70—C71—C76	38.9 (6)	C57—C54—C55—C56	−179.9 (4)
C76—C71—C72—C73	−2.1 (6)	C52—C51—C56—C55	0.1 (6)
N70—C71—C72—C73	179.3 (4)	N40—C51—C56—C55	−179.2 (3)
C71—C72—C73—C74	0.7 (6)	C54—C55—C56—C51	0.2 (6)
C71—C72—C73—C77	−179.1 (4)	C41—N40—C61—C62	−159.5 (3)
C72—C73—C74—C75	1.5 (7)	C51—N40—C61—C62	38.4 (5)
C77—C73—C74—C75	−178.8 (5)	C41—N40—C61—C66	20.8 (5)
C73—C74—C75—C76	−2.1 (7)	C51—N40—C61—C66	−141.3 (4)
C72—C71—C76—C75	1.5 (6)	C66—C61—C62—C63	0.7 (5)
N70—C71—C76—C75	−179.8 (4)	N40—C61—C62—C63	−179.0 (3)
C74—C75—C76—C71	0.5 (7)	C61—C62—C63—C64	−0.9 (6)
C71—N70—C81—C86	−136.9 (4)	C62—C63—C64—C65	0.4 (6)
C91—N70—C81—C86	42.3 (5)	C62—C63—C64—C67	179.6 (4)
C71—N70—C81—C82	43.7 (6)	C63—C64—C65—C66	0.3 (6)
C91—N70—C81—C82	−137.1 (4)	C67—C64—C65—C66	−179.0 (3)
C86—C81—C82—C83	0.0 (6)	C64—C65—C66—C61	−0.4 (6)
N70—C81—C82—C83	179.4 (4)	C62—C61—C66—C65	−0.1 (5)
C81—C82—C83—C84	−1.0 (7)	N40—C61—C66—C65	179.6 (3)