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The structure of the title compound, C
42H
54N
4, 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 (No. 2) with two half molecules in the asymmetric unit, both molecules being located on centres of inversion.
Supporting information
CCDC reference: 271856
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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).
Crystal data top
C42H54N4 | V = 1837.8 (8) Å3 |
Mr = 614.89 | Z = 2 |
Triclinic, P1 | F(000) = 668 |
Hall symbol: -P 1 | Dx = 1.111 Mg m−3 |
a = 11.915 (3) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 12.050 (4) Å | Cell parameters from 25 reflections |
c = 13.544 (2) Å | µ = 0.07 mm−1 |
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 tube | Rint = 0.026 |
Graphite monochromator | θmax = 27.0°, θmin = 2.0° |
φ or ω scans? | h = 0→15 |
8328 measured reflections | k = −15→15 |
7957 independent reflections | l = −17→17 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.080 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.270 | H-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 parameters | Δρmax = 0.32 e Å−3 |
10 restraints | Δρmin = −0.23 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
N51 | 0.0709 (2) | −0.1189 (2) | −0.0652 (2) | 0.0698 (7) | |
N52 | 0.7479 (2) | 0.5612 (2) | 0.3534 (2) | 0.0824 (8) | |
C62 | 0.0593 (2) | −0.0117 (3) | −0.0086 (2) | 0.0594 (8) | |
C63 | 0.1498 (2) | 0.0739 (3) | 0.0333 (2) | 0.0613 (8) | |
H63 | 0.1372 | 0.1469 | 0.0724 | 0.074* | |
C64 | 0.2596 (3) | 0.0515 (3) | 0.0172 (2) | 0.0629 (8) | |
C65 | 0.2711 (3) | −0.0581 (3) | −0.0429 (3) | 0.0726 (9) | |
H65 | 0.3421 | −0.0773 | −0.0582 | 0.087* | |
C66 | 0.1765 (3) | −0.1386 (3) | −0.0800 (3) | 0.0767 (9) | |
H66 | 0.1872 | −0.2126 | −0.1184 | 0.092* | |
C67 | 0.3593 (3) | 0.1375 (3) | 0.0612 (3) | 0.0691 (9) | |
H67 | 0.4215 | 0.1291 | 0.0272 | 0.083* | |
C68 | 0.3681 (3) | 0.2264 (3) | 0.1456 (3) | 0.0694 (9) | |
H68 | 0.3045 | 0.2333 | 0.1778 | 0.083* | |
C69 | 0.4642 (3) | 0.3146 (3) | 0.1945 (2) | 0.0617 (8) | |
C70 | 0.4675 (3) | 0.3889 (3) | 0.2927 (3) | 0.0767 (10) | |
H70 | 0.4052 | 0.3834 | 0.3254 | 0.092* | |
C71 | 0.5586 (3) | 0.4710 (3) | 0.3450 (3) | 0.0817 (10) | |
H71 | 0.5559 | 0.5192 | 0.4108 | 0.098* | |
C72 | 0.6550 (3) | 0.4825 (3) | 0.3000 (3) | 0.0697 (9) | |
C73 | 0.6491 (3) | 0.4119 (3) | 0.1988 (3) | 0.0699 (9) | |
H73 | 0.7093 | 0.4198 | 0.1642 | 0.084* | |
C74 | 0.5579 (3) | 0.3313 (3) | 0.1485 (2) | 0.0670 (8) | |
H74 | 0.5586 | 0.2859 | 0.0811 | 0.080* | |
C75 | 0.8452 (3) | 0.5764 (3) | 0.3047 (3) | 0.0933 (12) | |
H75A | 0.8860 | 0.6527 | 0.3387 | 0.112* | |
H75B | 0.8188 | 0.5713 | 0.2320 | 0.112* | |
C76 | 0.9282 (4) | 0.4816 (4) | 0.3126 (4) | 0.1174 (15) | |
H76A | 0.9599 | 0.4923 | 0.3855 | 0.141* | |
H76B | 0.8845 | 0.4058 | 0.2861 | 0.141* | |
C77 | 1.0174 (5) | 0.4839 (6) | 0.2582 (4) | 0.158 (2) | |
H77A | 1.0625 | 0.5588 | 0.2879 | 0.190* | |
H77B | 0.9846 | 0.4792 | 0.1868 | 0.190* | |
C78 | 1.0974 (4) | 0.3917 (4) | 0.2559 (4) | 0.1320 (18) | |
H78A | 1.1551 | 0.4032 | 0.2165 | 0.198* | |
H78B | 1.0552 | 0.3168 | 0.2238 | 0.198* | |
H78C | 1.1330 | 0.3962 | 0.3258 | 0.198* | |
C79 | 0.7629 (4) | 0.6195 (3) | 0.4633 (3) | 0.1028 (13) | |
H79A | 0.8376 | 0.6045 | 0.4940 | 0.123* | 0.464 (13) |
H79B | 0.7075 | 0.5791 | 0.4902 | 0.123* | 0.464 (13) |
H79C | 0.8430 | 0.6401 | 0.4949 | 0.123* | 0.536 (13) |
H79D | 0.7265 | 0.5734 | 0.5004 | 0.123* | 0.536 (13) |
C80 | 0.7554 (10) | 0.7461 (8) | 0.5086 (10) | 0.109 (5) | 0.464 (13) |
H80A | 0.7884 | 0.7689 | 0.5823 | 0.130* | 0.464 (13) |
H80B | 0.7992 | 0.7902 | 0.4747 | 0.130* | 0.464 (13) |
C81 | 0.6367 (7) | 0.7731 (8) | 0.4953 (10) | 0.087 (4) | 0.464 (13) |
H81A | 0.5925 | 0.7303 | 0.5300 | 0.104* | 0.464 (13) |
H81B | 0.6030 | 0.7508 | 0.4218 | 0.104* | 0.464 (13) |
C80' | 0.6995 (11) | 0.7302 (8) | 0.4586 (8) | 0.118 (5) | 0.536 (13) |
H80C | 0.7350 | 0.7709 | 0.4168 | 0.141* | 0.536 (13) |
H80D | 0.6203 | 0.7059 | 0.4251 | 0.141* | 0.536 (13) |
C81' | 0.7040 (13) | 0.8101 (9) | 0.5648 (9) | 0.171 (7) | 0.536 (13) |
H81C | 0.7823 | 0.8393 | 0.5983 | 0.205* | 0.536 (13) |
H81D | 0.6692 | 0.7712 | 0.6082 | 0.205* | 0.536 (13) |
C82 | 0.6345 (5) | 0.9103 (5) | 0.5449 (5) | 0.161 (2) | |
H82A | 0.5568 | 0.9275 | 0.5440 | 0.241* | 0.464 (13) |
H82B | 0.6701 | 0.9519 | 0.5047 | 0.241* | 0.464 (13) |
H82C | 0.6754 | 0.9334 | 0.6155 | 0.241* | 0.464 (13) |
H82D | 0.6365 | 0.9683 | 0.6098 | 0.241* | 0.536 (13) |
H82E | 0.5567 | 0.8799 | 0.5142 | 0.241* | 0.536 (13) |
H82F | 0.6677 | 0.9444 | 0.4983 | 0.241* | 0.536 (13) |
N1 | 0.0696 (2) | −0.6286 (2) | −0.0418 (2) | 0.0729 (7) | |
N2 | 0.7652 (2) | 0.0539 (2) | 0.3227 (2) | 0.0769 (8) | |
C2 | 0.0599 (3) | −0.5164 (3) | 0.0012 (2) | 0.0629 (8) | |
C3 | 0.1532 (3) | −0.4341 (3) | 0.0455 (2) | 0.0676 (9) | |
H3 | 0.1424 | −0.3568 | 0.0730 | 0.081* | |
C4 | 0.2636 (3) | −0.4674 (3) | 0.0489 (2) | 0.0644 (8) | |
C5 | 0.2722 (3) | −0.5842 (3) | 0.0048 (3) | 0.0746 (9) | |
H5 | 0.3436 | −0.6115 | 0.0050 | 0.089* | |
C6 | 0.1749 (3) | −0.6588 (3) | −0.0390 (3) | 0.0782 (10) | |
H6 | 0.1833 | −0.7362 | −0.0690 | 0.094* | |
C7 | 0.3679 (3) | −0.3873 (3) | 0.0959 (3) | 0.0737 (9) | |
H7 | 0.4356 | −0.4204 | 0.1073 | 0.088* | |
C8 | 0.3753 (3) | −0.2737 (3) | 0.1234 (2) | 0.0717 (9) | |
H8 | 0.3073 | −0.2414 | 0.1110 | 0.086* | |
C9 | 0.4785 (3) | −0.1906 (3) | 0.1717 (2) | 0.0660 (8) | |
C10 | 0.5861 (3) | −0.2246 (3) | 0.1975 (3) | 0.0733 (9) | |
H10 | 0.5948 | −0.3032 | 0.1831 | 0.088* | |
C11 | 0.6801 (3) | −0.1447 (3) | 0.2438 (3) | 0.0770 (10) | |
H11 | 0.7512 | −0.1709 | 0.2577 | 0.092* | |
C12 | 0.6716 (3) | −0.0260 (3) | 0.2706 (2) | 0.0654 (8) | |
C13 | 0.5635 (3) | 0.0079 (3) | 0.2430 (3) | 0.0715 (9) | |
H13 | 0.5541 | 0.0864 | 0.2571 | 0.086* | |
C14 | 0.4716 (3) | −0.0728 (3) | 0.1956 (3) | 0.0731 (9) | |
H14 | 0.4010 | −0.0469 | 0.1787 | 0.088* | |
C15 | 0.8744 (3) | 0.0146 (3) | 0.3592 (3) | 0.0829 (10) | |
H15A | 0.8590 | −0.0528 | 0.3831 | 0.100* | |
H15B | 0.9165 | 0.0754 | 0.4184 | 0.100* | |
C16 | 0.9486 (3) | −0.0162 (3) | 0.2763 (3) | 0.0812 (10) | |
H16A | 0.9030 | −0.0675 | 0.2128 | 0.097* | |
H16B | 0.9753 | 0.0538 | 0.2609 | 0.097* | |
C17 | 1.0506 (3) | −0.0747 (4) | 0.3111 (3) | 0.0979 (12) | |
H17A | 1.0951 | −0.0238 | 0.3754 | 0.118* | |
H17B | 1.0235 | −0.1452 | 0.3256 | 0.118* | |
C18 | 1.1259 (4) | −0.1041 (4) | 0.2315 (3) | 0.1218 (15) | |
H18A | 1.1889 | −0.1411 | 0.2572 | 0.183* | |
H18B | 1.1545 | −0.0345 | 0.2181 | 0.183* | |
H18C | 1.0828 | −0.1557 | 0.1681 | 0.183* | |
C19 | 0.7611 (3) | 0.1778 (3) | 0.3464 (3) | 0.0908 (11) | |
H19A | 0.6937 | 0.1904 | 0.3020 | 0.109* | 0.551 (15) |
H19B | 0.8267 | 0.2093 | 0.3246 | 0.109* | 0.551 (15) |
H19C | 0.7148 | 0.1980 | 0.2894 | 0.109* | 0.449 (15) |
H19D | 0.8373 | 0.2184 | 0.3603 | 0.109* | 0.449 (15) |
C20 | 0.7592 (11) | 0.2505 (9) | 0.4552 (8) | 0.126 (5) | 0.551 (15) |
H20A | 0.8229 | 0.2327 | 0.5005 | 0.152* | 0.551 (15) |
H20B | 0.7755 | 0.3308 | 0.4565 | 0.152* | 0.551 (15) |
C21 | 0.6710 (10) | 0.2448 (14) | 0.4975 (9) | 0.175 (8) | 0.551 (15) |
H21A | 0.6484 | 0.1638 | 0.4898 | 0.210* | 0.551 (15) |
H21B | 0.6091 | 0.2729 | 0.4584 | 0.210* | 0.551 (15) |
C21' | 0.7539 (12) | 0.273 (2) | 0.5290 (9) | 0.255 (14) | 0.449 (15) |
H21C | 0.7875 | 0.3414 | 0.5159 | 0.306* | 0.449 (15) |
H21D | 0.8165 | 0.2351 | 0.5563 | 0.306* | 0.449 (15) |
C20' | 0.7064 (13) | 0.2067 (14) | 0.4442 (11) | 0.198 (12) | 0.449 (15) |
H20C | 0.6351 | 0.2372 | 0.4253 | 0.238* | 0.449 (15) |
H20D | 0.6860 | 0.1333 | 0.4568 | 0.238* | 0.449 (15) |
C22 | 0.6832 (5) | 0.3139 (5) | 0.6172 (4) | 0.156 (2) | |
H22A | 0.6118 | 0.3036 | 0.6396 | 0.234* | 0.551 (15) |
H22B | 0.7033 | 0.3948 | 0.6264 | 0.234* | 0.551 (15) |
H22C | 0.7417 | 0.2849 | 0.6578 | 0.234* | 0.551 (15) |
H22D | 0.7337 | 0.3562 | 0.6805 | 0.234* | 0.449 (15) |
H22E | 0.6435 | 0.2477 | 0.6281 | 0.234* | 0.449 (15) |
H22F | 0.6287 | 0.3630 | 0.5972 | 0.234* | 0.449 (15) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N51 | 0.0675 (18) | 0.0601 (17) | 0.0762 (18) | 0.0068 (13) | 0.0161 (14) | 0.0082 (14) |
N52 | 0.079 (2) | 0.076 (2) | 0.084 (2) | −0.0060 (16) | 0.0072 (16) | 0.0150 (16) |
C62 | 0.0607 (18) | 0.0594 (19) | 0.0574 (17) | 0.0051 (16) | 0.0107 (15) | 0.0158 (15) |
C63 | 0.0581 (19) | 0.062 (2) | 0.0640 (18) | 0.0078 (16) | 0.0137 (15) | 0.0157 (15) |
C64 | 0.062 (2) | 0.062 (2) | 0.067 (2) | 0.0093 (16) | 0.0119 (16) | 0.0221 (17) |
C65 | 0.062 (2) | 0.075 (2) | 0.079 (2) | 0.0145 (18) | 0.0149 (17) | 0.0161 (18) |
C66 | 0.078 (2) | 0.065 (2) | 0.080 (2) | 0.0148 (19) | 0.0171 (19) | 0.0058 (17) |
C67 | 0.0584 (19) | 0.070 (2) | 0.078 (2) | 0.0061 (17) | 0.0153 (17) | 0.0187 (18) |
C68 | 0.0574 (19) | 0.075 (2) | 0.078 (2) | 0.0047 (17) | 0.0111 (16) | 0.0268 (19) |
C69 | 0.0592 (19) | 0.061 (2) | 0.068 (2) | 0.0126 (16) | 0.0135 (16) | 0.0220 (16) |
C70 | 0.072 (2) | 0.074 (2) | 0.086 (2) | 0.0005 (19) | 0.0278 (19) | 0.021 (2) |
C71 | 0.095 (3) | 0.070 (2) | 0.075 (2) | −0.001 (2) | 0.023 (2) | 0.0092 (18) |
C72 | 0.071 (2) | 0.060 (2) | 0.078 (2) | 0.0041 (17) | 0.0116 (18) | 0.0211 (18) |
C73 | 0.0577 (19) | 0.074 (2) | 0.078 (2) | 0.0058 (17) | 0.0152 (17) | 0.0187 (18) |
C74 | 0.066 (2) | 0.074 (2) | 0.0626 (19) | 0.0104 (17) | 0.0148 (16) | 0.0183 (17) |
C75 | 0.077 (3) | 0.078 (3) | 0.112 (3) | −0.004 (2) | 0.010 (2) | 0.013 (2) |
C76 | 0.088 (3) | 0.143 (4) | 0.116 (4) | 0.015 (3) | 0.012 (3) | 0.031 (3) |
C77 | 0.136 (5) | 0.244 (7) | 0.129 (4) | 0.054 (5) | 0.048 (4) | 0.090 (4) |
C78 | 0.111 (4) | 0.143 (4) | 0.127 (4) | 0.051 (3) | 0.008 (3) | 0.013 (3) |
C79 | 0.116 (3) | 0.081 (3) | 0.092 (3) | −0.007 (2) | 0.003 (2) | 0.005 (2) |
C80 | 0.155 (12) | 0.068 (7) | 0.072 (9) | −0.022 (7) | 0.027 (7) | −0.027 (6) |
C81 | 0.092 (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) |
C82 | 0.160 (5) | 0.121 (5) | 0.217 (7) | 0.027 (4) | 0.080 (5) | 0.045 (5) |
N1 | 0.078 (2) | 0.0578 (18) | 0.0829 (19) | 0.0096 (14) | 0.0091 (15) | 0.0232 (14) |
N2 | 0.0628 (17) | 0.074 (2) | 0.087 (2) | 0.0060 (15) | 0.0078 (15) | 0.0146 (16) |
C2 | 0.071 (2) | 0.059 (2) | 0.0589 (18) | 0.0041 (17) | 0.0089 (16) | 0.0185 (15) |
C3 | 0.075 (2) | 0.058 (2) | 0.068 (2) | 0.0038 (18) | 0.0135 (17) | 0.0142 (16) |
C4 | 0.066 (2) | 0.069 (2) | 0.0604 (19) | 0.0031 (17) | 0.0131 (15) | 0.0209 (16) |
C5 | 0.072 (2) | 0.072 (2) | 0.081 (2) | 0.0160 (19) | 0.0144 (18) | 0.0225 (19) |
C6 | 0.086 (3) | 0.060 (2) | 0.088 (2) | 0.011 (2) | 0.010 (2) | 0.0232 (18) |
C7 | 0.073 (2) | 0.076 (2) | 0.076 (2) | 0.0160 (19) | 0.0186 (18) | 0.0246 (19) |
C8 | 0.074 (2) | 0.077 (3) | 0.067 (2) | 0.0149 (19) | 0.0199 (17) | 0.0206 (18) |
C9 | 0.059 (2) | 0.079 (2) | 0.0615 (19) | 0.0100 (18) | 0.0165 (15) | 0.0183 (17) |
C10 | 0.079 (2) | 0.059 (2) | 0.081 (2) | 0.0086 (18) | 0.0194 (18) | 0.0155 (17) |
C11 | 0.067 (2) | 0.074 (2) | 0.087 (2) | 0.0110 (19) | 0.0130 (18) | 0.0176 (19) |
C12 | 0.065 (2) | 0.064 (2) | 0.0632 (19) | 0.0001 (17) | 0.0126 (16) | 0.0128 (16) |
C13 | 0.062 (2) | 0.070 (2) | 0.082 (2) | 0.0081 (18) | 0.0141 (17) | 0.0191 (18) |
C14 | 0.065 (2) | 0.073 (2) | 0.082 (2) | 0.0122 (19) | 0.0135 (17) | 0.0214 (18) |
C15 | 0.073 (2) | 0.092 (3) | 0.076 (2) | −0.0011 (19) | 0.0076 (18) | 0.0174 (19) |
C16 | 0.073 (2) | 0.086 (3) | 0.081 (2) | 0.0036 (19) | 0.0120 (19) | 0.0205 (19) |
C17 | 0.082 (3) | 0.116 (3) | 0.104 (3) | 0.021 (2) | 0.015 (2) | 0.043 (3) |
C18 | 0.114 (3) | 0.146 (4) | 0.110 (3) | 0.049 (3) | 0.030 (3) | 0.030 (3) |
C19 | 0.091 (3) | 0.073 (3) | 0.102 (3) | 0.002 (2) | 0.015 (2) | 0.017 (2) |
C20 | 0.171 (12) | 0.070 (7) | 0.102 (8) | −0.006 (7) | 0.025 (8) | −0.031 (5) |
C21 | 0.125 (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) |
C22 | 0.167 (5) | 0.164 (5) | 0.134 (5) | 0.049 (4) | 0.051 (4) | 0.019 (4) |
Geometric parameters (Å, º) top
N51—C66 | 1.330 (4) | N1—C6 | 1.325 (4) |
N51—C62 | 1.340 (4) | N1—C2 | 1.339 (4) |
N52—C72 | 1.378 (4) | N2—C12 | 1.387 (4) |
N52—C79 | 1.440 (4) | N2—C19 | 1.446 (4) |
N52—C75 | 1.447 (4) | N2—C15 | 1.469 (4) |
C62—C63 | 1.381 (4) | C2—C3 | 1.384 (4) |
C62—C62i | 1.498 (6) | C2—C2ii | 1.501 (6) |
C63—C64 | 1.391 (4) | C3—C4 | 1.395 (4) |
C63—H63 | 0.9300 | C3—H3 | 0.9300 |
C64—C65 | 1.378 (4) | C4—C5 | 1.389 (4) |
C64—C67 | 1.461 (4) | C4—C7 | 1.468 (4) |
C65—C66 | 1.375 (4) | C5—C6 | 1.369 (4) |
C65—H65 | 0.9300 | C5—H5 | 0.9300 |
C66—H66 | 0.9300 | C6—H6 | 0.9300 |
C67—C68 | 1.323 (4) | C7—C8 | 1.312 (4) |
C67—H67 | 0.9300 | C7—H7 | 0.9300 |
C68—C69 | 1.453 (4) | C8—C9 | 1.479 (4) |
C68—H68 | 0.9300 | C8—H8 | 0.9300 |
C69—C70 | 1.383 (4) | C9—C14 | 1.379 (4) |
C69—C74 | 1.392 (4) | C9—C10 | 1.389 (4) |
C70—C71 | 1.382 (4) | C10—C11 | 1.377 (4) |
C70—H70 | 0.9300 | C10—H10 | 0.9300 |
C71—C72 | 1.399 (4) | C11—C12 | 1.392 (4) |
C71—H71 | 0.9300 | C11—H11 | 0.9300 |
C72—C73 | 1.394 (4) | C12—C13 | 1.399 (4) |
C73—C74 | 1.368 (4) | C13—C14 | 1.367 (4) |
C73—H73 | 0.9300 | C13—H13 | 0.9300 |
C74—H74 | 0.9300 | C14—H14 | 0.9300 |
C75—C76 | 1.569 (5) | C15—C16 | 1.519 (4) |
C75—H75A | 0.9700 | C15—H15A | 0.9700 |
C75—H75B | 0.9700 | C15—H15B | 0.9700 |
C76—C77 | 1.389 (6) | C16—C17 | 1.515 (5) |
C76—H76A | 0.9700 | C16—H16A | 0.9700 |
C76—H76B | 0.9700 | C16—H16B | 0.9700 |
C77—C78 | 1.504 (6) | C17—C18 | 1.494 (5) |
C77—H77A | 0.9700 | C17—H17A | 0.9700 |
C77—H77B | 0.9700 | C17—H17B | 0.9700 |
C78—H78A | 0.9600 | C18—H18A | 0.9600 |
C78—H78B | 0.9600 | C18—H18B | 0.9600 |
C78—H78C | 0.9600 | C18—H18C | 0.9600 |
C79—C80 | 1.497 (9) | C19—C20 | 1.501 (8) |
C79—C80' | 1.582 (11) | C19—C20' | 1.534 (11) |
C79—H79A | 0.9700 | C19—H19A | 0.9700 |
C79—H79B | 0.9700 | C19—H19B | 0.9700 |
C79—H79C | 0.9700 | C19—H19C | 0.9700 |
C79—H79D | 0.9700 | C19—H19D | 0.9700 |
C80—C81 | 1.464 (11) | C20—C21 | 1.281 (13) |
C80—H80A | 0.9700 | C20—H20A | 0.9700 |
C80—H80B | 0.9700 | C20—H20B | 0.9700 |
C81—C82 | 1.611 (10) | C21—C22 | 1.589 (11) |
C81—H81A | 0.9700 | C21—H21A | 0.9700 |
C81—H81B | 0.9700 | C21—H21B | 0.9700 |
C80'—C81' | 1.490 (12) | C21'—C20' | 1.233 (12) |
C80'—H80C | 0.9700 | C21'—C22 | 1.559 (11) |
C80'—H80D | 0.9700 | C21'—H21C | 0.9700 |
C81'—C82 | 1.562 (12) | C21'—H21D | 0.9700 |
C81'—H81C | 0.9700 | C20'—H20C | 0.9700 |
C81'—H81D | 0.9700 | C20'—H20D | 0.9700 |
C82—H82A | 0.9600 | C22—H22A | 0.9600 |
C82—H82B | 0.9600 | C22—H22B | 0.9600 |
C82—H82C | 0.9600 | C22—H22C | 0.9600 |
C82—H82D | 0.9600 | C22—H22D | 0.9600 |
C82—H82E | 0.9600 | C22—H22E | 0.9600 |
C82—H82F | 0.9600 | C22—H22F | 0.9600 |
| | | |
C66—N51—C62 | 115.7 (3) | C12—N2—C19 | 123.1 (3) |
C72—N52—C79 | 123.1 (3) | C12—N2—C15 | 120.4 (3) |
C72—N52—C75 | 120.7 (3) | C19—N2—C15 | 116.5 (3) |
C79—N52—C75 | 115.6 (3) | N1—C2—C3 | 123.1 (3) |
N51—C62—C63 | 123.2 (3) | N1—C2—C2ii | 115.9 (3) |
N51—C62—C62i | 116.2 (3) | C3—C2—C2ii | 121.0 (4) |
C63—C62—C62i | 120.5 (4) | C2—C3—C4 | 119.9 (3) |
C62—C63—C64 | 120.2 (3) | C2—C3—H3 | 120.1 |
C62—C63—H63 | 119.9 | C4—C3—H3 | 120.1 |
C64—C63—H63 | 119.9 | C5—C4—C3 | 116.4 (3) |
C65—C64—C63 | 116.4 (3) | C5—C4—C7 | 119.6 (3) |
C65—C64—C67 | 120.6 (3) | C3—C4—C7 | 124.0 (3) |
C63—C64—C67 | 122.9 (3) | C6—C5—C4 | 119.5 (3) |
C66—C65—C64 | 119.4 (3) | C6—C5—H5 | 120.2 |
C66—C65—H65 | 120.3 | C4—C5—H5 | 120.2 |
C64—C65—H65 | 120.3 | N1—C6—C5 | 124.7 (3) |
N51—C66—C65 | 125.0 (3) | N1—C6—H6 | 117.6 |
N51—C66—H66 | 117.5 | C5—C6—H6 | 117.6 |
C65—C66—H66 | 117.5 | C8—C7—C4 | 126.5 (3) |
C68—C67—C64 | 125.3 (3) | C8—C7—H7 | 116.7 |
C68—C67—H67 | 117.3 | C4—C7—H7 | 116.7 |
C64—C67—H67 | 117.3 | C7—C8—C9 | 127.9 (3) |
C67—C68—C69 | 128.5 (3) | C7—C8—H8 | 116.0 |
C67—C68—H68 | 115.7 | C9—C8—H8 | 116.0 |
C69—C68—H68 | 115.7 | C14—C9—C10 | 116.1 (3) |
C70—C69—C74 | 115.1 (3) | C14—C9—C8 | 120.7 (3) |
C70—C69—C68 | 120.8 (3) | C10—C9—C8 | 123.2 (3) |
C74—C69—C68 | 124.1 (3) | C11—C10—C9 | 121.6 (3) |
C71—C70—C69 | 123.4 (3) | C11—C10—H10 | 119.2 |
C71—C70—H70 | 118.3 | C9—C10—H10 | 119.2 |
C69—C70—H70 | 118.3 | C10—C11—C12 | 121.8 (3) |
C70—C71—C72 | 120.8 (3) | C10—C11—H11 | 119.1 |
C70—C71—H71 | 119.6 | C12—C11—H11 | 119.1 |
C72—C71—H71 | 119.6 | N2—C12—C11 | 121.6 (3) |
N52—C72—C73 | 123.1 (3) | N2—C12—C13 | 122.1 (3) |
N52—C72—C71 | 121.0 (3) | C11—C12—C13 | 116.3 (3) |
C73—C72—C71 | 115.9 (3) | C14—C13—C12 | 120.9 (3) |
C74—C73—C72 | 122.2 (3) | C14—C13—H13 | 119.6 |
C74—C73—H73 | 118.9 | C12—C13—H13 | 119.6 |
C72—C73—H73 | 118.9 | C13—C14—C9 | 123.2 (3) |
C73—C74—C69 | 122.4 (3) | C13—C14—H14 | 118.4 |
C73—C74—H74 | 118.8 | C9—C14—H14 | 118.4 |
C69—C74—H74 | 118.8 | N2—C15—C16 | 113.5 (3) |
N52—C75—C76 | 110.9 (3) | N2—C15—H15A | 108.9 |
N52—C75—H75A | 109.5 | C16—C15—H15A | 108.9 |
C76—C75—H75A | 109.5 | N2—C15—H15B | 108.9 |
N52—C75—H75B | 109.5 | C16—C15—H15B | 108.9 |
C76—C75—H75B | 109.5 | H15A—C15—H15B | 107.7 |
H75A—C75—H75B | 108.1 | C17—C16—C15 | 111.8 (3) |
C77—C76—C75 | 113.8 (4) | C17—C16—H16A | 109.3 |
C77—C76—H76A | 108.8 | C15—C16—H16A | 109.3 |
C75—C76—H76A | 108.8 | C17—C16—H16B | 109.3 |
C77—C76—H76B | 108.8 | C15—C16—H16B | 109.3 |
C75—C76—H76B | 108.8 | H16A—C16—H16B | 107.9 |
H76A—C76—H76B | 107.7 | C18—C17—C16 | 112.8 (3) |
C76—C77—C78 | 117.7 (5) | C18—C17—H17A | 109.0 |
C76—C77—H77A | 107.9 | C16—C17—H17A | 109.0 |
C78—C77—H77A | 107.9 | C18—C17—H17B | 109.0 |
C76—C77—H77B | 107.9 | C16—C17—H17B | 109.0 |
C78—C77—H77B | 107.9 | H17A—C17—H17B | 107.8 |
H77A—C77—H77B | 107.2 | C17—C18—H18A | 109.5 |
C77—C78—H78A | 109.5 | C17—C18—H18B | 109.5 |
C77—C78—H78B | 109.5 | H18A—C18—H18B | 109.5 |
H78A—C78—H78B | 109.5 | C17—C18—H18C | 109.5 |
C77—C78—H78C | 109.5 | H18A—C18—H18C | 109.5 |
H78A—C78—H78C | 109.5 | H18B—C18—H18C | 109.5 |
H78B—C78—H78C | 109.5 | N2—C19—C20 | 121.3 (5) |
N52—C79—C80 | 124.8 (6) | N2—C19—C20' | 103.4 (8) |
N52—C79—C80' | 99.6 (5) | N2—C19—H19A | 107.0 |
N52—C79—H79A | 106.1 | C20—C19—H19A | 107.0 |
C80—C79—H79A | 106.1 | N2—C19—H19B | 107.0 |
N52—C79—H79B | 106.1 | C20—C19—H19B | 107.0 |
C80—C79—H79B | 106.1 | H19A—C19—H19B | 106.7 |
H79A—C79—H79B | 106.3 | N2—C19—H19C | 111.1 |
N52—C79—H79C | 111.8 | C20—C19—H19C | 117.4 |
C80'—C79—H79C | 111.8 | C20'—C19—H19C | 111.1 |
N52—C79—H79D | 111.8 | N2—C19—H19D | 111.1 |
C80'—C79—H79D | 111.8 | C20'—C19—H19D | 111.1 |
H79C—C79—H79D | 109.6 | H19C—C19—H19D | 109.0 |
C81—C80—C79 | 111.3 (9) | C21—C20—C19 | 121.4 (11) |
C81—C80—H80A | 109.4 | C21—C20—H20A | 107.0 |
C79—C80—H80A | 109.4 | C19—C20—H20A | 107.0 |
C81—C80—H80B | 109.4 | C21—C20—H20B | 107.0 |
C79—C80—H80B | 109.4 | C19—C20—H20B | 107.0 |
H80A—C80—H80B | 108.0 | H20A—C20—H20B | 106.7 |
C80—C81—C82 | 108.9 (8) | C20—C21—C22 | 117.2 (11) |
C80—C81—H81A | 109.9 | C20—C21—H21A | 108.0 |
C82—C81—H81A | 109.9 | C22—C21—H21A | 108.0 |
C80—C81—H81B | 109.9 | C20—C21—H21B | 108.0 |
C82—C81—H81B | 109.9 | C22—C21—H21B | 108.0 |
H81A—C81—H81B | 108.3 | H21A—C21—H21B | 107.2 |
C81'—C80'—C79 | 111.4 (9) | C20'—C21'—C22 | 119.6 (11) |
C81'—C80'—H80C | 109.3 | C20'—C21'—H21C | 107.4 |
C79—C80'—H80C | 109.3 | C22—C21'—H21C | 107.4 |
C81'—C80'—H80D | 109.3 | C20'—C21'—H21D | 107.4 |
C79—C80'—H80D | 109.3 | C22—C21'—H21D | 107.4 |
H80C—C80'—H80D | 108.0 | H21C—C21'—H21D | 107.0 |
C80'—C81'—C82 | 104.1 (9) | C21'—C20'—C19 | 124.0 (10) |
C80'—C81'—H81C | 110.9 | C21'—C20'—H20C | 106.3 |
C82—C81'—H81C | 110.9 | C19—C20'—H20C | 106.3 |
C80'—C81'—H81D | 110.9 | C21'—C20'—H20D | 106.3 |
C82—C81'—H81D | 110.9 | C19—C20'—H20D | 106.3 |
H81C—C81'—H81D | 109.0 | H20C—C20'—H20D | 106.4 |
C81—C82—H82A | 109.5 | C21—C22—H22A | 109.5 |
C81—C82—H82B | 109.5 | C21—C22—H22B | 109.5 |
H82A—C82—H82B | 109.5 | H22A—C22—H22B | 109.5 |
C81'—C82—H82C | 70.8 | C21—C22—H22C | 109.5 |
C81'—C82—H82D | 109.5 | H22A—C22—H22C | 109.5 |
C81'—C82—H82E | 109.5 | H22B—C22—H22C | 109.5 |
C81—C82—H82E | 74.2 | C21'—C22—H22D | 109.5 |
H82D—C82—H82E | 109.5 | C21'—C22—H22E | 109.5 |
C81'—C82—H82F | 109.5 | H22D—C22—H22E | 109.5 |
H82D—C82—H82F | 109.5 | C21'—C22—H22F | 109.5 |
H82E—C82—H82F | 109.5 | H22D—C22—H22F | 109.5 |
C6—N1—C2 | 116.4 (3) | H22E—C22—H22F | 109.5 |
| | | |
C66—N51—C62—C63 | −0.5 (4) | C6—N1—C2—C3 | 0.9 (4) |
C66—N51—C62—C62i | 179.9 (3) | C6—N1—C2—C2ii | −179.3 (3) |
N51—C62—C63—C64 | 0.4 (5) | N1—C2—C3—C4 | −1.6 (5) |
C62i—C62—C63—C64 | 179.9 (3) | C2ii—C2—C3—C4 | 178.5 (3) |
C62—C63—C64—C65 | 0.9 (4) | C2—C3—C4—C5 | 1.0 (4) |
C62—C63—C64—C67 | −178.6 (3) | C2—C3—C4—C7 | −178.8 (3) |
C63—C64—C65—C66 | −2.0 (5) | C3—C4—C5—C6 | 0.3 (5) |
C67—C64—C65—C66 | 177.5 (3) | C7—C4—C5—C6 | −179.9 (3) |
C62—N51—C66—C65 | −0.7 (5) | C2—N1—C6—C5 | 0.5 (5) |
C64—C65—C66—N51 | 2.1 (5) | C4—C5—C6—N1 | −1.1 (5) |
C65—C64—C67—C68 | −155.0 (3) | C5—C4—C7—C8 | 167.0 (3) |
C63—C64—C67—C68 | 24.5 (5) | C3—C4—C7—C8 | −13.3 (5) |
C64—C67—C68—C69 | 179.4 (3) | C4—C7—C8—C9 | 179.3 (3) |
C67—C68—C69—C70 | −168.0 (3) | C7—C8—C9—C14 | 179.8 (3) |
C67—C68—C69—C74 | 11.9 (5) | C7—C8—C9—C10 | −1.6 (5) |
C74—C69—C70—C71 | −2.8 (5) | C14—C9—C10—C11 | −0.3 (5) |
C68—C69—C70—C71 | 177.1 (3) | C8—C9—C10—C11 | −179.0 (3) |
C69—C70—C71—C72 | −0.5 (5) | C9—C10—C11—C12 | 2.3 (5) |
C79—N52—C72—C73 | −168.9 (3) | C19—N2—C12—C11 | 176.4 (3) |
C75—N52—C72—C73 | 1.5 (5) | C15—N2—C12—C11 | −5.3 (5) |
C79—N52—C72—C71 | 12.4 (5) | C19—N2—C12—C13 | −4.3 (5) |
C75—N52—C72—C71 | −177.2 (3) | C15—N2—C12—C13 | 174.0 (3) |
C70—C71—C72—N52 | −177.5 (3) | C10—C11—C12—N2 | 176.2 (3) |
C70—C71—C72—C73 | 3.8 (5) | C10—C11—C12—C13 | −3.1 (5) |
N52—C72—C73—C74 | 177.5 (3) | N2—C12—C13—C14 | −177.2 (3) |
C71—C72—C73—C74 | −3.8 (5) | C11—C12—C13—C14 | 2.1 (5) |
C72—C73—C74—C69 | 0.5 (5) | C12—C13—C14—C9 | −0.3 (5) |
C70—C69—C74—C73 | 2.8 (4) | C10—C9—C14—C13 | −0.7 (5) |
C68—C69—C74—C73 | −177.1 (3) | C8—C9—C14—C13 | 178.1 (3) |
C72—N52—C75—C76 | −82.7 (4) | C12—N2—C15—C16 | 84.7 (4) |
C79—N52—C75—C76 | 88.4 (4) | C19—N2—C15—C16 | −96.8 (4) |
N52—C75—C76—C77 | 173.8 (4) | N2—C15—C16—C17 | −170.5 (3) |
C75—C76—C77—C78 | −176.4 (4) | C15—C16—C17—C18 | −179.1 (3) |
C72—N52—C79—C80 | −110.7 (7) | C12—N2—C19—C20 | 105.6 (7) |
C75—N52—C79—C80 | 78.5 (7) | C15—N2—C19—C20 | −72.8 (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—C81 | 74.5 (12) | N2—C19—C20—C21 | −70.9 (14) |
C80'—C79—C80—C81 | 32.3 (11) | C20'—C19—C20—C21 | −13 (2) |
C79—C80—C81—C82 | −179.6 (7) | C19—C20—C21—C22 | 172.9 (8) |
N52—C79—C80'—C81' | −178.7 (10) | C22—C21'—C20'—C19 | 168.7 (15) |
C80—C79—C80'—C81' | −32.7 (12) | N2—C19—C20'—C21' | 119 (3) |
C79—C80'—C81'—C82 | −178.1 (8) | C20—C19—C20'—C21' | −13.0 (18) |
C80'—C81'—C82—C81 | 31.6 (8) | C20'—C21'—C22—C21 | −7.7 (18) |
C80—C81—C82—C81' | −34.2 (10) | C20—C21—C22—C21' | −11.1 (17) |
Symmetry codes: (i) −x, −y, −z; (ii) −x, −y−1, −z. |
Results of the refinement in P1 and P1. top | P1 | P1 |
reflections | 7957 | 8401 |
parameters | 453 | 820 |
R[F2 > 2σ(F2)] | 0.0795 | 0.0776 |
wR(F2) | 0.2702 | 0.3179 |
S | 1.023 | 0.928 |
(Δ/σ)max | <0.001 | 0.851 |
N1-C2 | 1.325 (4) | 1.366 (13) |
N1-C6 | 1.325 (4) | 1.295 (14) |
N3-C32 | - | 1.311 (12) |
N3-C36 | - | 1.383 (15) |
N51-C62 | 1.340 (4) | 1.349 (12) |
N51-C66 | 1.330 (4) | 1.315 (14) |
N53-C92 | - | 1.324 (12) |
N53-C92 | - | 1.353 (14) |
C6-N1-C2 | 116.4 (3) | 114.0 (9) |
C32-N3-C36 | - | 119.4 (9) |
C66-N51-C62 | 115.7 (3) | 116.0 (8) |
C92-N53-C96 | - | 115.8 (9) |
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