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The structure of the title compound, C42H54N4, has originally been refined in space group P1 (No. 1) with two mol­ecules in the asymmetric unit. However, successful refinement clearly demonstrates that the structure is better described in space group P\overline{1} (No. 2) with two half mol­ecules in the asymmetric unit, both molecules being located on centres of inversion.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805011414/cv6490sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805011414/cv6490Isup2.hkl
Contains datablock I

CCDC reference: 271856

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.079
  • wR factor = 0.270
  • Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found



Alert level A CELL004_ALERT_1_A _cell_measurement_theta_min is missing Minimum theta of reflections used to measure unit cell. The following tests will not be performed. CELLT_01
Author Response: This value has not been given by the authors who first published this structure.
CELL005_ALERT_1_A  _cell_measurement_theta_max is missing
            Maximum theta of reflections used to measure unit cell.
            The following tests will not be performed.
            CELLT_01
Author Response: This value has not been given by the authors who first published this structure.
DIFF019_ALERT_1_A  _diffrn_standards_number is missing
            Number of standards used in measurement.
Author Response: This value has not been given by the authors who first published this structure.
DIFF020_ALERT_1_A  _diffrn_standards_interval_count and
            _diffrn_standards_interval_time are missing. Number of measurements
            between standards or time (min) between standards.
Author Response: This value has not been given by the authors who first published this structure.
DIFF022_ALERT_1_A  _diffrn_standards_decay_% is missing
            Percentage decrease in standards intensity.
Author Response: This value has not been given by the authors who first published this structure.
PLAT213_ALERT_2_A Atom C20'    has ADP max/min Ratio .............       5.50 prolat
Author Response: This atom is disordered.
PLAT241_ALERT_2_A Check High      Ueq as Compared to Neighbors for       C21'
Author Response: This atom is disordered.
PLAT242_ALERT_2_A Check Low       Ueq as Compared to Neighbors for        C22
Author Response: This atom is a neighbour of a disordered atom.

Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.03 Ratio PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C21
Author Response: This atom is disordered.
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C77
Author Response: This atom is disordered.
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for       C81'
Author Response: This atom is disordered.
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C82
Author Response: This atom is disordered.
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C19
Author Response: This atom is a neighbour of a disordered atom.
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C81
Author Response: This atom is a neighbour of a disordered atom.

Alert level C RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.270 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 41 Perc. PLAT084_ALERT_2_C High R2 Value .................................. 0.27 PLAT213_ALERT_2_C Atom C21' has ADP max/min Ratio ............. 3.20 prolat
Author Response: This atom is disordered.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.88 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.78 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.26 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C20'
Author Response: This atom is disordered.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C80'
Author Response: This atom is a neighbour of a disordered atom.
PLAT301_ALERT_3_C Main Residue  Disorder .........................       8.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C76    -   C77    ...       1.39 Ang.
PLAT410_ALERT_2_C Short Intra H...H Contact  H13    ..  H19A    ..       1.93 Ang.
PLAT410_ALERT_2_C Short Intra H...H Contact  H71    ..  H79B    ..       1.94 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C42 H54 N4

8 ALERT level A = In general: serious problem 7 ALERT level B = Potentially serious problem 15 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 18 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: Enraf–Nonius CAD-4; cell refinement: Enraf–Nonius CAD-4; data reduction: Enraf–Nonius CAD-4; program(s) used to solve structure: coordinates were input directly; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

; top
Crystal data top
C42H54N4V = 1837.8 (8) Å3
Mr = 614.89Z = 2
Triclinic, P1F(000) = 668
Hall symbol: -P 1Dx = 1.111 Mg m3
a = 11.915 (3) ÅMo Kα radiation, λ = 0.71069 Å
b = 12.050 (4) ÅCell parameters from 25 reflections
c = 13.544 (2) ŵ = 0.07 mm1
α = 105.67 (2)°T = 293 K
β = 99.141 (10)°Prism, yellow
γ = 93.40 (2)°0.45 × 0.35 × 0.32 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
3290 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 27.0°, θmin = 2.0°
φ or ω scans?h = 015
8328 measured reflectionsk = 1515
7957 independent reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.080Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.270H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.1309P)2 + 0.0377P]
where P = (Fo2 + 2Fc2)/3
7957 reflections(Δ/σ)max < 0.001
453 parametersΔρmax = 0.32 e Å3
10 restraintsΔρmin = 0.23 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
N510.0709 (2)0.1189 (2)0.0652 (2)0.0698 (7)
N520.7479 (2)0.5612 (2)0.3534 (2)0.0824 (8)
C620.0593 (2)0.0117 (3)0.0086 (2)0.0594 (8)
C630.1498 (2)0.0739 (3)0.0333 (2)0.0613 (8)
H630.13720.14690.07240.074*
C640.2596 (3)0.0515 (3)0.0172 (2)0.0629 (8)
C650.2711 (3)0.0581 (3)0.0429 (3)0.0726 (9)
H650.34210.07730.05820.087*
C660.1765 (3)0.1386 (3)0.0800 (3)0.0767 (9)
H660.18720.21260.11840.092*
C670.3593 (3)0.1375 (3)0.0612 (3)0.0691 (9)
H670.42150.12910.02720.083*
C680.3681 (3)0.2264 (3)0.1456 (3)0.0694 (9)
H680.30450.23330.17780.083*
C690.4642 (3)0.3146 (3)0.1945 (2)0.0617 (8)
C700.4675 (3)0.3889 (3)0.2927 (3)0.0767 (10)
H700.40520.38340.32540.092*
C710.5586 (3)0.4710 (3)0.3450 (3)0.0817 (10)
H710.55590.51920.41080.098*
C720.6550 (3)0.4825 (3)0.3000 (3)0.0697 (9)
C730.6491 (3)0.4119 (3)0.1988 (3)0.0699 (9)
H730.70930.41980.16420.084*
C740.5579 (3)0.3313 (3)0.1485 (2)0.0670 (8)
H740.55860.28590.08110.080*
C750.8452 (3)0.5764 (3)0.3047 (3)0.0933 (12)
H75A0.88600.65270.33870.112*
H75B0.81880.57130.23200.112*
C760.9282 (4)0.4816 (4)0.3126 (4)0.1174 (15)
H76A0.95990.49230.38550.141*
H76B0.88450.40580.28610.141*
C771.0174 (5)0.4839 (6)0.2582 (4)0.158 (2)
H77A1.06250.55880.28790.190*
H77B0.98460.47920.18680.190*
C781.0974 (4)0.3917 (4)0.2559 (4)0.1320 (18)
H78A1.15510.40320.21650.198*
H78B1.05520.31680.22380.198*
H78C1.13300.39620.32580.198*
C790.7629 (4)0.6195 (3)0.4633 (3)0.1028 (13)
H79A0.83760.60450.49400.123*0.464 (13)
H79B0.70750.57910.49020.123*0.464 (13)
H79C0.84300.64010.49490.123*0.536 (13)
H79D0.72650.57340.50040.123*0.536 (13)
C800.7554 (10)0.7461 (8)0.5086 (10)0.109 (5)0.464 (13)
H80A0.78840.76890.58230.130*0.464 (13)
H80B0.79920.79020.47470.130*0.464 (13)
C810.6367 (7)0.7731 (8)0.4953 (10)0.087 (4)0.464 (13)
H81A0.59250.73030.53000.104*0.464 (13)
H81B0.60300.75080.42180.104*0.464 (13)
C80'0.6995 (11)0.7302 (8)0.4586 (8)0.118 (5)0.536 (13)
H80C0.73500.77090.41680.141*0.536 (13)
H80D0.62030.70590.42510.141*0.536 (13)
C81'0.7040 (13)0.8101 (9)0.5648 (9)0.171 (7)0.536 (13)
H81C0.78230.83930.59830.205*0.536 (13)
H81D0.66920.77120.60820.205*0.536 (13)
C820.6345 (5)0.9103 (5)0.5449 (5)0.161 (2)
H82A0.55680.92750.54400.241*0.464 (13)
H82B0.67010.95190.50470.241*0.464 (13)
H82C0.67540.93340.61550.241*0.464 (13)
H82D0.63650.96830.60980.241*0.536 (13)
H82E0.55670.87990.51420.241*0.536 (13)
H82F0.66770.94440.49830.241*0.536 (13)
N10.0696 (2)0.6286 (2)0.0418 (2)0.0729 (7)
N20.7652 (2)0.0539 (2)0.3227 (2)0.0769 (8)
C20.0599 (3)0.5164 (3)0.0012 (2)0.0629 (8)
C30.1532 (3)0.4341 (3)0.0455 (2)0.0676 (9)
H30.14240.35680.07300.081*
C40.2636 (3)0.4674 (3)0.0489 (2)0.0644 (8)
C50.2722 (3)0.5842 (3)0.0048 (3)0.0746 (9)
H50.34360.61150.00500.089*
C60.1749 (3)0.6588 (3)0.0390 (3)0.0782 (10)
H60.18330.73620.06900.094*
C70.3679 (3)0.3873 (3)0.0959 (3)0.0737 (9)
H70.43560.42040.10730.088*
C80.3753 (3)0.2737 (3)0.1234 (2)0.0717 (9)
H80.30730.24140.11100.086*
C90.4785 (3)0.1906 (3)0.1717 (2)0.0660 (8)
C100.5861 (3)0.2246 (3)0.1975 (3)0.0733 (9)
H100.59480.30320.18310.088*
C110.6801 (3)0.1447 (3)0.2438 (3)0.0770 (10)
H110.75120.17090.25770.092*
C120.6716 (3)0.0260 (3)0.2706 (2)0.0654 (8)
C130.5635 (3)0.0079 (3)0.2430 (3)0.0715 (9)
H130.55410.08640.25710.086*
C140.4716 (3)0.0728 (3)0.1956 (3)0.0731 (9)
H140.40100.04690.17870.088*
C150.8744 (3)0.0146 (3)0.3592 (3)0.0829 (10)
H15A0.85900.05280.38310.100*
H15B0.91650.07540.41840.100*
C160.9486 (3)0.0162 (3)0.2763 (3)0.0812 (10)
H16A0.90300.06750.21280.097*
H16B0.97530.05380.26090.097*
C171.0506 (3)0.0747 (4)0.3111 (3)0.0979 (12)
H17A1.09510.02380.37540.118*
H17B1.02350.14520.32560.118*
C181.1259 (4)0.1041 (4)0.2315 (3)0.1218 (15)
H18A1.18890.14110.25720.183*
H18B1.15450.03450.21810.183*
H18C1.08280.15570.16810.183*
C190.7611 (3)0.1778 (3)0.3464 (3)0.0908 (11)
H19A0.69370.19040.30200.109*0.551 (15)
H19B0.82670.20930.32460.109*0.551 (15)
H19C0.71480.19800.28940.109*0.449 (15)
H19D0.83730.21840.36030.109*0.449 (15)
C200.7592 (11)0.2505 (9)0.4552 (8)0.126 (5)0.551 (15)
H20A0.82290.23270.50050.152*0.551 (15)
H20B0.77550.33080.45650.152*0.551 (15)
C210.6710 (10)0.2448 (14)0.4975 (9)0.175 (8)0.551 (15)
H21A0.64840.16380.48980.210*0.551 (15)
H21B0.60910.27290.45840.210*0.551 (15)
C21'0.7539 (12)0.273 (2)0.5290 (9)0.255 (14)0.449 (15)
H21C0.78750.34140.51590.306*0.449 (15)
H21D0.81650.23510.55630.306*0.449 (15)
C20'0.7064 (13)0.2067 (14)0.4442 (11)0.198 (12)0.449 (15)
H20C0.63510.23720.42530.238*0.449 (15)
H20D0.68600.13330.45680.238*0.449 (15)
C220.6832 (5)0.3139 (5)0.6172 (4)0.156 (2)
H22A0.61180.30360.63960.234*0.551 (15)
H22B0.70330.39480.62640.234*0.551 (15)
H22C0.74170.28490.65780.234*0.551 (15)
H22D0.73370.35620.68050.234*0.449 (15)
H22E0.64350.24770.62810.234*0.449 (15)
H22F0.62870.36300.59720.234*0.449 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N510.0675 (18)0.0601 (17)0.0762 (18)0.0068 (13)0.0161 (14)0.0082 (14)
N520.079 (2)0.076 (2)0.084 (2)0.0060 (16)0.0072 (16)0.0150 (16)
C620.0607 (18)0.0594 (19)0.0574 (17)0.0051 (16)0.0107 (15)0.0158 (15)
C630.0581 (19)0.062 (2)0.0640 (18)0.0078 (16)0.0137 (15)0.0157 (15)
C640.062 (2)0.062 (2)0.067 (2)0.0093 (16)0.0119 (16)0.0221 (17)
C650.062 (2)0.075 (2)0.079 (2)0.0145 (18)0.0149 (17)0.0161 (18)
C660.078 (2)0.065 (2)0.080 (2)0.0148 (19)0.0171 (19)0.0058 (17)
C670.0584 (19)0.070 (2)0.078 (2)0.0061 (17)0.0153 (17)0.0187 (18)
C680.0574 (19)0.075 (2)0.078 (2)0.0047 (17)0.0111 (16)0.0268 (19)
C690.0592 (19)0.061 (2)0.068 (2)0.0126 (16)0.0135 (16)0.0220 (16)
C700.072 (2)0.074 (2)0.086 (2)0.0005 (19)0.0278 (19)0.021 (2)
C710.095 (3)0.070 (2)0.075 (2)0.001 (2)0.023 (2)0.0092 (18)
C720.071 (2)0.060 (2)0.078 (2)0.0041 (17)0.0116 (18)0.0211 (18)
C730.0577 (19)0.074 (2)0.078 (2)0.0058 (17)0.0152 (17)0.0187 (18)
C740.066 (2)0.074 (2)0.0626 (19)0.0104 (17)0.0148 (16)0.0183 (17)
C750.077 (3)0.078 (3)0.112 (3)0.004 (2)0.010 (2)0.013 (2)
C760.088 (3)0.143 (4)0.116 (4)0.015 (3)0.012 (3)0.031 (3)
C770.136 (5)0.244 (7)0.129 (4)0.054 (5)0.048 (4)0.090 (4)
C780.111 (4)0.143 (4)0.127 (4)0.051 (3)0.008 (3)0.013 (3)
C790.116 (3)0.081 (3)0.092 (3)0.007 (2)0.003 (2)0.005 (2)
C800.155 (12)0.068 (7)0.072 (9)0.022 (7)0.027 (7)0.027 (6)
C810.092 (7)0.077 (8)0.106 (10)0.024 (5)0.028 (6)0.043 (7)
C80'0.157 (15)0.073 (7)0.093 (8)0.045 (8)0.021 (7)0.014 (5)
C81'0.239 (18)0.140 (12)0.116 (9)0.047 (12)0.019 (10)0.027 (8)
C820.160 (5)0.121 (5)0.217 (7)0.027 (4)0.080 (5)0.045 (5)
N10.078 (2)0.0578 (18)0.0829 (19)0.0096 (14)0.0091 (15)0.0232 (14)
N20.0628 (17)0.074 (2)0.087 (2)0.0060 (15)0.0078 (15)0.0146 (16)
C20.071 (2)0.059 (2)0.0589 (18)0.0041 (17)0.0089 (16)0.0185 (15)
C30.075 (2)0.058 (2)0.068 (2)0.0038 (18)0.0135 (17)0.0142 (16)
C40.066 (2)0.069 (2)0.0604 (19)0.0031 (17)0.0131 (15)0.0209 (16)
C50.072 (2)0.072 (2)0.081 (2)0.0160 (19)0.0144 (18)0.0225 (19)
C60.086 (3)0.060 (2)0.088 (2)0.011 (2)0.010 (2)0.0232 (18)
C70.073 (2)0.076 (2)0.076 (2)0.0160 (19)0.0186 (18)0.0246 (19)
C80.074 (2)0.077 (3)0.067 (2)0.0149 (19)0.0199 (17)0.0206 (18)
C90.059 (2)0.079 (2)0.0615 (19)0.0100 (18)0.0165 (15)0.0183 (17)
C100.079 (2)0.059 (2)0.081 (2)0.0086 (18)0.0194 (18)0.0155 (17)
C110.067 (2)0.074 (2)0.087 (2)0.0110 (19)0.0130 (18)0.0176 (19)
C120.065 (2)0.064 (2)0.0632 (19)0.0001 (17)0.0126 (16)0.0128 (16)
C130.062 (2)0.070 (2)0.082 (2)0.0081 (18)0.0141 (17)0.0191 (18)
C140.065 (2)0.073 (2)0.082 (2)0.0122 (19)0.0135 (17)0.0214 (18)
C150.073 (2)0.092 (3)0.076 (2)0.0011 (19)0.0076 (18)0.0174 (19)
C160.073 (2)0.086 (3)0.081 (2)0.0036 (19)0.0120 (19)0.0205 (19)
C170.082 (3)0.116 (3)0.104 (3)0.021 (2)0.015 (2)0.043 (3)
C180.114 (3)0.146 (4)0.110 (3)0.049 (3)0.030 (3)0.030 (3)
C190.091 (3)0.073 (3)0.102 (3)0.002 (2)0.015 (2)0.017 (2)
C200.171 (12)0.070 (7)0.102 (8)0.006 (7)0.025 (8)0.031 (5)
C210.125 (10)0.29 (2)0.154 (14)0.069 (11)0.070 (9)0.108 (14)
C21'0.126 (12)0.46 (3)0.077 (9)0.120 (16)0.038 (9)0.068 (13)
C20'0.127 (13)0.114 (12)0.26 (2)0.097 (10)0.064 (14)0.101 (12)
C220.167 (5)0.164 (5)0.134 (5)0.049 (4)0.051 (4)0.019 (4)
Geometric parameters (Å, º) top
N51—C661.330 (4)N1—C61.325 (4)
N51—C621.340 (4)N1—C21.339 (4)
N52—C721.378 (4)N2—C121.387 (4)
N52—C791.440 (4)N2—C191.446 (4)
N52—C751.447 (4)N2—C151.469 (4)
C62—C631.381 (4)C2—C31.384 (4)
C62—C62i1.498 (6)C2—C2ii1.501 (6)
C63—C641.391 (4)C3—C41.395 (4)
C63—H630.9300C3—H30.9300
C64—C651.378 (4)C4—C51.389 (4)
C64—C671.461 (4)C4—C71.468 (4)
C65—C661.375 (4)C5—C61.369 (4)
C65—H650.9300C5—H50.9300
C66—H660.9300C6—H60.9300
C67—C681.323 (4)C7—C81.312 (4)
C67—H670.9300C7—H70.9300
C68—C691.453 (4)C8—C91.479 (4)
C68—H680.9300C8—H80.9300
C69—C701.383 (4)C9—C141.379 (4)
C69—C741.392 (4)C9—C101.389 (4)
C70—C711.382 (4)C10—C111.377 (4)
C70—H700.9300C10—H100.9300
C71—C721.399 (4)C11—C121.392 (4)
C71—H710.9300C11—H110.9300
C72—C731.394 (4)C12—C131.399 (4)
C73—C741.368 (4)C13—C141.367 (4)
C73—H730.9300C13—H130.9300
C74—H740.9300C14—H140.9300
C75—C761.569 (5)C15—C161.519 (4)
C75—H75A0.9700C15—H15A0.9700
C75—H75B0.9700C15—H15B0.9700
C76—C771.389 (6)C16—C171.515 (5)
C76—H76A0.9700C16—H16A0.9700
C76—H76B0.9700C16—H16B0.9700
C77—C781.504 (6)C17—C181.494 (5)
C77—H77A0.9700C17—H17A0.9700
C77—H77B0.9700C17—H17B0.9700
C78—H78A0.9600C18—H18A0.9600
C78—H78B0.9600C18—H18B0.9600
C78—H78C0.9600C18—H18C0.9600
C79—C801.497 (9)C19—C201.501 (8)
C79—C80'1.582 (11)C19—C20'1.534 (11)
C79—H79A0.9700C19—H19A0.9700
C79—H79B0.9700C19—H19B0.9700
C79—H79C0.9700C19—H19C0.9700
C79—H79D0.9700C19—H19D0.9700
C80—C811.464 (11)C20—C211.281 (13)
C80—H80A0.9700C20—H20A0.9700
C80—H80B0.9700C20—H20B0.9700
C81—C821.611 (10)C21—C221.589 (11)
C81—H81A0.9700C21—H21A0.9700
C81—H81B0.9700C21—H21B0.9700
C80'—C81'1.490 (12)C21'—C20'1.233 (12)
C80'—H80C0.9700C21'—C221.559 (11)
C80'—H80D0.9700C21'—H21C0.9700
C81'—C821.562 (12)C21'—H21D0.9700
C81'—H81C0.9700C20'—H20C0.9700
C81'—H81D0.9700C20'—H20D0.9700
C82—H82A0.9600C22—H22A0.9600
C82—H82B0.9600C22—H22B0.9600
C82—H82C0.9600C22—H22C0.9600
C82—H82D0.9600C22—H22D0.9600
C82—H82E0.9600C22—H22E0.9600
C82—H82F0.9600C22—H22F0.9600
C66—N51—C62115.7 (3)C12—N2—C19123.1 (3)
C72—N52—C79123.1 (3)C12—N2—C15120.4 (3)
C72—N52—C75120.7 (3)C19—N2—C15116.5 (3)
C79—N52—C75115.6 (3)N1—C2—C3123.1 (3)
N51—C62—C63123.2 (3)N1—C2—C2ii115.9 (3)
N51—C62—C62i116.2 (3)C3—C2—C2ii121.0 (4)
C63—C62—C62i120.5 (4)C2—C3—C4119.9 (3)
C62—C63—C64120.2 (3)C2—C3—H3120.1
C62—C63—H63119.9C4—C3—H3120.1
C64—C63—H63119.9C5—C4—C3116.4 (3)
C65—C64—C63116.4 (3)C5—C4—C7119.6 (3)
C65—C64—C67120.6 (3)C3—C4—C7124.0 (3)
C63—C64—C67122.9 (3)C6—C5—C4119.5 (3)
C66—C65—C64119.4 (3)C6—C5—H5120.2
C66—C65—H65120.3C4—C5—H5120.2
C64—C65—H65120.3N1—C6—C5124.7 (3)
N51—C66—C65125.0 (3)N1—C6—H6117.6
N51—C66—H66117.5C5—C6—H6117.6
C65—C66—H66117.5C8—C7—C4126.5 (3)
C68—C67—C64125.3 (3)C8—C7—H7116.7
C68—C67—H67117.3C4—C7—H7116.7
C64—C67—H67117.3C7—C8—C9127.9 (3)
C67—C68—C69128.5 (3)C7—C8—H8116.0
C67—C68—H68115.7C9—C8—H8116.0
C69—C68—H68115.7C14—C9—C10116.1 (3)
C70—C69—C74115.1 (3)C14—C9—C8120.7 (3)
C70—C69—C68120.8 (3)C10—C9—C8123.2 (3)
C74—C69—C68124.1 (3)C11—C10—C9121.6 (3)
C71—C70—C69123.4 (3)C11—C10—H10119.2
C71—C70—H70118.3C9—C10—H10119.2
C69—C70—H70118.3C10—C11—C12121.8 (3)
C70—C71—C72120.8 (3)C10—C11—H11119.1
C70—C71—H71119.6C12—C11—H11119.1
C72—C71—H71119.6N2—C12—C11121.6 (3)
N52—C72—C73123.1 (3)N2—C12—C13122.1 (3)
N52—C72—C71121.0 (3)C11—C12—C13116.3 (3)
C73—C72—C71115.9 (3)C14—C13—C12120.9 (3)
C74—C73—C72122.2 (3)C14—C13—H13119.6
C74—C73—H73118.9C12—C13—H13119.6
C72—C73—H73118.9C13—C14—C9123.2 (3)
C73—C74—C69122.4 (3)C13—C14—H14118.4
C73—C74—H74118.8C9—C14—H14118.4
C69—C74—H74118.8N2—C15—C16113.5 (3)
N52—C75—C76110.9 (3)N2—C15—H15A108.9
N52—C75—H75A109.5C16—C15—H15A108.9
C76—C75—H75A109.5N2—C15—H15B108.9
N52—C75—H75B109.5C16—C15—H15B108.9
C76—C75—H75B109.5H15A—C15—H15B107.7
H75A—C75—H75B108.1C17—C16—C15111.8 (3)
C77—C76—C75113.8 (4)C17—C16—H16A109.3
C77—C76—H76A108.8C15—C16—H16A109.3
C75—C76—H76A108.8C17—C16—H16B109.3
C77—C76—H76B108.8C15—C16—H16B109.3
C75—C76—H76B108.8H16A—C16—H16B107.9
H76A—C76—H76B107.7C18—C17—C16112.8 (3)
C76—C77—C78117.7 (5)C18—C17—H17A109.0
C76—C77—H77A107.9C16—C17—H17A109.0
C78—C77—H77A107.9C18—C17—H17B109.0
C76—C77—H77B107.9C16—C17—H17B109.0
C78—C77—H77B107.9H17A—C17—H17B107.8
H77A—C77—H77B107.2C17—C18—H18A109.5
C77—C78—H78A109.5C17—C18—H18B109.5
C77—C78—H78B109.5H18A—C18—H18B109.5
H78A—C78—H78B109.5C17—C18—H18C109.5
C77—C78—H78C109.5H18A—C18—H18C109.5
H78A—C78—H78C109.5H18B—C18—H18C109.5
H78B—C78—H78C109.5N2—C19—C20121.3 (5)
N52—C79—C80124.8 (6)N2—C19—C20'103.4 (8)
N52—C79—C80'99.6 (5)N2—C19—H19A107.0
N52—C79—H79A106.1C20—C19—H19A107.0
C80—C79—H79A106.1N2—C19—H19B107.0
N52—C79—H79B106.1C20—C19—H19B107.0
C80—C79—H79B106.1H19A—C19—H19B106.7
H79A—C79—H79B106.3N2—C19—H19C111.1
N52—C79—H79C111.8C20—C19—H19C117.4
C80'—C79—H79C111.8C20'—C19—H19C111.1
N52—C79—H79D111.8N2—C19—H19D111.1
C80'—C79—H79D111.8C20'—C19—H19D111.1
H79C—C79—H79D109.6H19C—C19—H19D109.0
C81—C80—C79111.3 (9)C21—C20—C19121.4 (11)
C81—C80—H80A109.4C21—C20—H20A107.0
C79—C80—H80A109.4C19—C20—H20A107.0
C81—C80—H80B109.4C21—C20—H20B107.0
C79—C80—H80B109.4C19—C20—H20B107.0
H80A—C80—H80B108.0H20A—C20—H20B106.7
C80—C81—C82108.9 (8)C20—C21—C22117.2 (11)
C80—C81—H81A109.9C20—C21—H21A108.0
C82—C81—H81A109.9C22—C21—H21A108.0
C80—C81—H81B109.9C20—C21—H21B108.0
C82—C81—H81B109.9C22—C21—H21B108.0
H81A—C81—H81B108.3H21A—C21—H21B107.2
C81'—C80'—C79111.4 (9)C20'—C21'—C22119.6 (11)
C81'—C80'—H80C109.3C20'—C21'—H21C107.4
C79—C80'—H80C109.3C22—C21'—H21C107.4
C81'—C80'—H80D109.3C20'—C21'—H21D107.4
C79—C80'—H80D109.3C22—C21'—H21D107.4
H80C—C80'—H80D108.0H21C—C21'—H21D107.0
C80'—C81'—C82104.1 (9)C21'—C20'—C19124.0 (10)
C80'—C81'—H81C110.9C21'—C20'—H20C106.3
C82—C81'—H81C110.9C19—C20'—H20C106.3
C80'—C81'—H81D110.9C21'—C20'—H20D106.3
C82—C81'—H81D110.9C19—C20'—H20D106.3
H81C—C81'—H81D109.0H20C—C20'—H20D106.4
C81—C82—H82A109.5C21—C22—H22A109.5
C81—C82—H82B109.5C21—C22—H22B109.5
H82A—C82—H82B109.5H22A—C22—H22B109.5
C81'—C82—H82C70.8C21—C22—H22C109.5
C81'—C82—H82D109.5H22A—C22—H22C109.5
C81'—C82—H82E109.5H22B—C22—H22C109.5
C81—C82—H82E74.2C21'—C22—H22D109.5
H82D—C82—H82E109.5C21'—C22—H22E109.5
C81'—C82—H82F109.5H22D—C22—H22E109.5
H82D—C82—H82F109.5C21'—C22—H22F109.5
H82E—C82—H82F109.5H22D—C22—H22F109.5
C6—N1—C2116.4 (3)H22E—C22—H22F109.5
C66—N51—C62—C630.5 (4)C6—N1—C2—C30.9 (4)
C66—N51—C62—C62i179.9 (3)C6—N1—C2—C2ii179.3 (3)
N51—C62—C63—C640.4 (5)N1—C2—C3—C41.6 (5)
C62i—C62—C63—C64179.9 (3)C2ii—C2—C3—C4178.5 (3)
C62—C63—C64—C650.9 (4)C2—C3—C4—C51.0 (4)
C62—C63—C64—C67178.6 (3)C2—C3—C4—C7178.8 (3)
C63—C64—C65—C662.0 (5)C3—C4—C5—C60.3 (5)
C67—C64—C65—C66177.5 (3)C7—C4—C5—C6179.9 (3)
C62—N51—C66—C650.7 (5)C2—N1—C6—C50.5 (5)
C64—C65—C66—N512.1 (5)C4—C5—C6—N11.1 (5)
C65—C64—C67—C68155.0 (3)C5—C4—C7—C8167.0 (3)
C63—C64—C67—C6824.5 (5)C3—C4—C7—C813.3 (5)
C64—C67—C68—C69179.4 (3)C4—C7—C8—C9179.3 (3)
C67—C68—C69—C70168.0 (3)C7—C8—C9—C14179.8 (3)
C67—C68—C69—C7411.9 (5)C7—C8—C9—C101.6 (5)
C74—C69—C70—C712.8 (5)C14—C9—C10—C110.3 (5)
C68—C69—C70—C71177.1 (3)C8—C9—C10—C11179.0 (3)
C69—C70—C71—C720.5 (5)C9—C10—C11—C122.3 (5)
C79—N52—C72—C73168.9 (3)C19—N2—C12—C11176.4 (3)
C75—N52—C72—C731.5 (5)C15—N2—C12—C115.3 (5)
C79—N52—C72—C7112.4 (5)C19—N2—C12—C134.3 (5)
C75—N52—C72—C71177.2 (3)C15—N2—C12—C13174.0 (3)
C70—C71—C72—N52177.5 (3)C10—C11—C12—N2176.2 (3)
C70—C71—C72—C733.8 (5)C10—C11—C12—C133.1 (5)
N52—C72—C73—C74177.5 (3)N2—C12—C13—C14177.2 (3)
C71—C72—C73—C743.8 (5)C11—C12—C13—C142.1 (5)
C72—C73—C74—C690.5 (5)C12—C13—C14—C90.3 (5)
C70—C69—C74—C732.8 (4)C10—C9—C14—C130.7 (5)
C68—C69—C74—C73177.1 (3)C8—C9—C14—C13178.1 (3)
C72—N52—C75—C7682.7 (4)C12—N2—C15—C1684.7 (4)
C79—N52—C75—C7688.4 (4)C19—N2—C15—C1696.8 (4)
N52—C75—C76—C77173.8 (4)N2—C15—C16—C17170.5 (3)
C75—C76—C77—C78176.4 (4)C15—C16—C17—C18179.1 (3)
C72—N52—C79—C80110.7 (7)C12—N2—C19—C20105.6 (7)
C75—N52—C79—C8078.5 (7)C15—N2—C19—C2072.8 (7)
C72—N52—C79—C80'89.7 (6)C12—N2—C19—C20'80.6 (8)
C75—N52—C79—C80'99.4 (6)C15—N2—C19—C20'97.9 (8)
N52—C79—C80—C8174.5 (12)N2—C19—C20—C2170.9 (14)
C80'—C79—C80—C8132.3 (11)C20'—C19—C20—C2113 (2)
C79—C80—C81—C82179.6 (7)C19—C20—C21—C22172.9 (8)
N52—C79—C80'—C81'178.7 (10)C22—C21'—C20'—C19168.7 (15)
C80—C79—C80'—C81'32.7 (12)N2—C19—C20'—C21'119 (3)
C79—C80'—C81'—C82178.1 (8)C20—C19—C20'—C21'13.0 (18)
C80'—C81'—C82—C8131.6 (8)C20'—C21'—C22—C217.7 (18)
C80—C81—C82—C81'34.2 (10)C20—C21—C22—C21'11.1 (17)
Symmetry codes: (i) x, y, z; (ii) x, y1, z.
Results of the refinement in P1 and P1. top
P1P1
reflections79578401
parameters453820
R[F2 > 2σ(F2)]0.07950.0776
wR(F2)0.27020.3179
S1.0230.928
(Δ/σ)max<0.0010.851
N1-C21.325 (4)1.366 (13)
N1-C61.325 (4)1.295 (14)
N3-C32-1.311 (12)
N3-C36-1.383 (15)
N51-C621.340 (4)1.349 (12)
N51-C661.330 (4)1.315 (14)
N53-C92-1.324 (12)
N53-C92-1.353 (14)
C6-N1-C2116.4 (3)114.0 (9)
C32-N3-C36-119.4 (9)
C66-N51-C62115.7 (3)116.0 (8)
C92-N53-C96-115.8 (9)
 

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