The title compound [systematic name: 21,24-dimethyl-3,12,21,24-tetraazahexacyclo[9.7.3.3
2,10.0
1,10.0
4,9.0
13,18]tetracosa-4,6,8,13(18),14,16-hexaene monohydrate], C
22H
28N
4·H
2O, crystallizes in space group
P2
12
12
1 with
Z = 4 and exhibits approximate
C2 symmetry. Intermolecular hydrogen bonds [O—H
N = 2.872 (3)° and N—H
O = 3.062 (4) Å] form chains along the direction [010].
Supporting information
CCDC reference: 242335
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.065
- wR factor = 0.150
- Data-to-parameter ratio = 8.1
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.87
| Author Response: The intensities measurements were extended to
theta(max)= 74.86 degrees but 302 reflections could not
be measured due to scintillator-collimator collision predicted.
The total reflections measured was 2444, but 342 were
rejected after data reduction and refinement.
|
_diffrn_reflns_theta_full 74.86
As explained above, the measurements during data collection were
extended to 74.86, with reduction of expected reflections due to
obscuration near the collimator.
Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor O1 - H2W ... ?
| Author Response: `see _publ_section_exptl_refinement'
|
PROBLEM: D-H Without Acceptor N26 - H26 ...
RESPONSE: `see _publ_section_exptl_refinement'
`see _publ_section_exptl_refinement'
Alert level C
REFLT03_ALERT_1_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 74.86
From the CIF: _diffrn_reflns_theta_full 0.00
From the CIF: _reflns_number_total 2051
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 2200
Completeness (_total/calc) 93.23%
| Author Response: The line below shows that the theta_full is 74.86
and not zero, as stated.
|
PROBLEM: Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
RESPONSE: `see _publ_section_exptl_refinement'
`see _publ_section_exptl_refinement'
Estimate of Friedel pairs measured 51
Are heavy atom types Z>Si present no
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.93
PLAT420_ALERT_2_C D-H Without Acceptor N26 - H26 ... ?
| Author Response: `see _publ_section_exptl_refinement'
|
PROBLEM: D-H Without Acceptor N26 - H26 ...
RESPONSE: `see _publ_section_exptl_refinement'
`see _publ_section_exptl_refinement'
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 74.86
From the CIF: _reflns_number_total 2051
Count of symmetry unique reflns 2200
Completeness (_total/calc) 93.23%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
| Author Response: The line below shows that the theta_full is 74.86
and not zero, as stated.
|
PROBLEM: Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
RESPONSE: `see _publ_section_exptl_refinement'
`see _publ_section_exptl_refinement'
Estimate of Friedel pairs measured 51
Are heavy atom types Z>Si present no
1 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 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
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 Software (Enraf–Nonius, 1994); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
21,24-dimethyl-3,12,21,24-tetraazahexacyclo[9.7.3.3
2,10.
O
1,10·O
4,9·O
13,18]tetracosa-4,6,8,13 (18),14,16-hexaene
top
Crystal data top
C22H26N4·H2O | Dx = 1.292 Mg m−3 |
Mr = 364.48 | Melting point = 245–250 K |
Orthorhombic, P212121 | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 25 reflections |
a = 10.419 (6) Å | θ = 21.2–40.1° |
b = 12.996 (2) Å | µ = 0.64 mm−1 |
c = 13.841 (2) Å | T = 293 K |
V = 1874.1 (11) Å3 | Irregular, brown |
Z = 4 | 0.35 × 0.32 × 0.20 mm |
F(000) = 784 | |
Data collection top
Enraf-Nonius CAD-4 diffractometer | θmax = 74.9°, θmin = 4.7° |
non–profiled ω/2θ scans | h = 0→13 |
2102 measured reflections | k = 0→16 |
2051 independent reflections | l = −1→17 |
2018 reflections with I > 2σ(I) | 2 standard reflections every 120 min |
Rint = 0.015 | intensity decay: 1% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.065 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.150 | w = 1/[σ2(Fo2) + (0.1114P)2 + 0.1995P] where P = (Fo2 + 2Fc2)/3 |
S = 1.16 | (Δ/σ)max = 0.023 |
2051 reflections | Δρmax = 0.47 e Å−3 |
254 parameters | Δρmin = −0.38 e Å−3 |
3 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.141 (8) |
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 | |
O1 | 0.1865 (3) | 0.27333 (17) | 0.7058 (2) | 0.0745 (7) | |
C2 | 0.2959 (3) | 0.83674 (19) | 0.97945 (19) | 0.0512 (7) | |
H2 | 0.3071 | 0.8904 | 1.0231 | 0.061* | |
C3 | 0.3848 (3) | 0.8213 (2) | 0.90715 (19) | 0.0491 (7) | |
H3 | 0.4552 | 0.8650 | 0.9023 | 0.059* | |
C4 | 0.3701 (2) | 0.74026 (19) | 0.84055 (17) | 0.0401 (6) | |
C5 | 0.2608 (2) | 0.67757 (17) | 0.84627 (15) | 0.0352 (5) | |
C6 | 0.1743 (3) | 0.69437 (18) | 0.92086 (16) | 0.0399 (6) | |
H6 | 0.1032 | 0.6514 | 0.9262 | 0.048* | |
C7 | 0.1900 (3) | 0.77290 (19) | 0.98764 (18) | 0.0467 (6) | |
H7 | 0.1306 | 0.7825 | 1.0370 | 0.056* | |
C8 | 0.1046 (2) | 0.56883 (17) | 0.74923 (16) | 0.0356 (5) | |
H8 | 0.0593 | 0.5507 | 0.8089 | 0.043* | |
C9 | 0.2463 (2) | 0.58910 (17) | 0.77474 (15) | 0.0345 (5) | |
N10 | 0.0949 (2) | 0.48025 (15) | 0.68226 (14) | 0.0403 (5) | |
C11 | −0.0386 (3) | 0.4539 (2) | 0.6651 (2) | 0.0527 (7) | |
H11A | −0.0802 | 0.4400 | 0.7256 | 0.079* | |
H11B | −0.0431 | 0.3939 | 0.6247 | 0.079* | |
H11C | −0.0809 | 0.5103 | 0.6336 | 0.079* | |
C12 | 0.1595 (3) | 0.5018 (2) | 0.58953 (16) | 0.0457 (6) | |
H12A | 0.1156 | 0.5576 | 0.5569 | 0.055* | |
H12B | 0.1548 | 0.4413 | 0.5485 | 0.055* | |
C13 | 0.2986 (3) | 0.5307 (2) | 0.60507 (17) | 0.0435 (6) | |
H13A | 0.3360 | 0.5517 | 0.5440 | 0.052* | |
H13B | 0.3455 | 0.4710 | 0.6281 | 0.052* | |
C14 | 0.3122 (2) | 0.61881 (19) | 0.67871 (15) | 0.0375 (5) | |
C15 | 0.4540 (3) | 0.6369 (2) | 0.70445 (18) | 0.0457 (6) | |
H15 | 0.4990 | 0.6561 | 0.6450 | 0.055* | |
N16 | 0.5111 (2) | 0.5409 (2) | 0.73995 (18) | 0.0493 (6) | |
C17 | 0.6504 (3) | 0.5455 (3) | 0.7487 (3) | 0.0672 (9) | |
H17A | 0.6867 | 0.5688 | 0.6888 | 0.101* | |
H17B | 0.6831 | 0.4783 | 0.7637 | 0.101* | |
H17C | 0.6732 | 0.5925 | 0.7994 | 0.101* | |
C18 | 0.4534 (3) | 0.5067 (2) | 0.83102 (18) | 0.0470 (6) | |
H18A | 0.4702 | 0.5572 | 0.8811 | 0.056* | |
H18B | 0.4918 | 0.4420 | 0.8507 | 0.056* | |
C19 | 0.3102 (3) | 0.49285 (18) | 0.81925 (17) | 0.0415 (6) | |
H19A | 0.2721 | 0.4791 | 0.8819 | 0.050* | |
H19B | 0.2939 | 0.4339 | 0.7780 | 0.050* | |
C20 | 0.2469 (4) | 0.8651 (3) | 0.5349 (2) | 0.0642 (9) | |
H20 | 0.2908 | 0.9098 | 0.4941 | 0.077* | |
C21 | 0.3103 (3) | 0.7830 (2) | 0.57652 (19) | 0.0528 (7) | |
H21 | 0.3970 | 0.7737 | 0.5634 | 0.063* | |
C22 | 0.2482 (3) | 0.71381 (19) | 0.63748 (16) | 0.0401 (6) | |
C23 | 0.1159 (3) | 0.72997 (17) | 0.65511 (17) | 0.0395 (6) | |
C24 | 0.0536 (3) | 0.8136 (2) | 0.61311 (19) | 0.0502 (7) | |
H24 | −0.0333 | 0.8241 | 0.6252 | 0.060* | |
C25 | 0.1186 (4) | 0.8810 (2) | 0.5539 (2) | 0.0600 (8) | |
H25 | 0.0761 | 0.9370 | 0.5268 | 0.072* | |
N26 | 0.4621 (2) | 0.72361 (18) | 0.77089 (17) | 0.0481 (6) | |
H26 | 0.5258 | 0.7654 | 0.7665 | 0.058* | |
N27 | 0.0479 (2) | 0.66176 (16) | 0.71153 (16) | 0.0417 (5) | |
H27 | −0.026 (3) | 0.682 (2) | 0.735 (2) | 0.050* | |
H1W | 0.157 (3) | 0.3387 (16) | 0.698 (2) | 0.050* | |
H2W | 0.222 (3) | 0.256 (2) | 0.6479 (17) | 0.050* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0941 (19) | 0.0512 (11) | 0.0782 (15) | 0.0042 (13) | 0.0149 (16) | −0.0032 (12) |
C2 | 0.0715 (19) | 0.0386 (11) | 0.0435 (12) | 0.0027 (13) | −0.0103 (13) | −0.0091 (10) |
C3 | 0.0585 (17) | 0.0422 (11) | 0.0465 (13) | −0.0064 (13) | −0.0078 (13) | −0.0029 (11) |
C4 | 0.0458 (14) | 0.0402 (11) | 0.0342 (10) | −0.0039 (11) | −0.0024 (10) | 0.0009 (9) |
C5 | 0.0433 (13) | 0.0337 (9) | 0.0287 (9) | −0.0006 (10) | −0.0032 (10) | 0.0003 (9) |
C6 | 0.0484 (14) | 0.0395 (10) | 0.0318 (10) | 0.0053 (12) | 0.0012 (10) | −0.0008 (9) |
C7 | 0.0591 (15) | 0.0466 (12) | 0.0344 (11) | 0.0109 (13) | −0.0009 (12) | −0.0058 (10) |
C8 | 0.0385 (12) | 0.0367 (10) | 0.0317 (10) | 0.0007 (10) | 0.0015 (10) | −0.0019 (9) |
C9 | 0.0404 (12) | 0.0345 (9) | 0.0285 (9) | 0.0021 (10) | 0.0009 (9) | −0.0015 (8) |
N10 | 0.0444 (12) | 0.0387 (9) | 0.0378 (9) | −0.0033 (9) | −0.0041 (9) | −0.0036 (8) |
C11 | 0.0480 (14) | 0.0557 (14) | 0.0543 (14) | −0.0089 (14) | −0.0095 (13) | −0.0018 (12) |
C12 | 0.0569 (16) | 0.0479 (12) | 0.0323 (10) | 0.0004 (14) | −0.0046 (11) | −0.0092 (10) |
C13 | 0.0445 (14) | 0.0543 (13) | 0.0318 (10) | 0.0037 (12) | 0.0019 (10) | −0.0103 (10) |
C14 | 0.0396 (12) | 0.0450 (10) | 0.0280 (9) | −0.0010 (11) | 0.0022 (9) | −0.0025 (9) |
C15 | 0.0427 (13) | 0.0585 (14) | 0.0358 (11) | −0.0037 (13) | 0.0030 (11) | −0.0038 (12) |
N16 | 0.0391 (12) | 0.0620 (13) | 0.0466 (11) | 0.0068 (11) | −0.0024 (10) | −0.0086 (11) |
C17 | 0.0397 (15) | 0.092 (2) | 0.0700 (19) | 0.0046 (17) | −0.0015 (14) | −0.010 (2) |
C18 | 0.0482 (14) | 0.0493 (12) | 0.0435 (12) | 0.0081 (13) | −0.0030 (11) | −0.0033 (11) |
C19 | 0.0477 (14) | 0.0391 (10) | 0.0377 (11) | 0.0062 (12) | −0.0060 (11) | −0.0025 (10) |
C20 | 0.086 (2) | 0.0607 (15) | 0.0458 (14) | −0.0172 (18) | −0.0014 (16) | 0.0167 (13) |
C21 | 0.0633 (17) | 0.0590 (14) | 0.0362 (12) | −0.0143 (16) | 0.0028 (12) | 0.0038 (11) |
C22 | 0.0491 (15) | 0.0421 (11) | 0.0290 (10) | −0.0032 (12) | 0.0018 (10) | −0.0012 (9) |
C23 | 0.0489 (14) | 0.0377 (10) | 0.0318 (10) | −0.0021 (11) | −0.0059 (10) | −0.0010 (9) |
C24 | 0.0608 (16) | 0.0447 (12) | 0.0451 (12) | 0.0027 (13) | −0.0091 (13) | 0.0016 (11) |
C25 | 0.084 (2) | 0.0461 (12) | 0.0499 (13) | −0.0031 (15) | −0.0137 (16) | 0.0119 (12) |
N26 | 0.0433 (12) | 0.0544 (11) | 0.0466 (11) | −0.0140 (11) | 0.0020 (10) | −0.0074 (10) |
N27 | 0.0389 (11) | 0.0426 (9) | 0.0434 (11) | 0.0051 (10) | 0.0024 (10) | 0.0049 (9) |
Geometric parameters (Å, º) top
O1—H1W | 0.911 (17) | C13—H13B | 0.9700 |
O1—H2W | 0.908 (18) | C14—C22 | 1.515 (3) |
C2—C3 | 1.378 (4) | C14—C15 | 1.537 (4) |
C2—C7 | 1.385 (4) | C15—N26 | 1.457 (3) |
C2—H2 | 0.9300 | C15—N16 | 1.467 (4) |
C3—C4 | 1.408 (3) | C15—H15 | 0.9800 |
C3—H3 | 0.9300 | N16—C17 | 1.457 (4) |
C4—N26 | 1.376 (4) | N16—C18 | 1.466 (4) |
C4—C5 | 1.403 (4) | C17—H17A | 0.9600 |
C5—C6 | 1.388 (3) | C17—H17B | 0.9600 |
C5—C9 | 1.525 (3) | C17—H17C | 0.9600 |
C6—C7 | 1.387 (3) | C18—C19 | 1.512 (4) |
C6—H6 | 0.9300 | C18—H18A | 0.9700 |
C7—H7 | 0.9300 | C18—H18B | 0.9700 |
C8—N27 | 1.442 (3) | C19—H19A | 0.9700 |
C8—N10 | 1.481 (3) | C19—H19B | 0.9700 |
C8—C9 | 1.541 (3) | C20—C25 | 1.377 (6) |
C8—H8 | 0.9800 | C20—C21 | 1.381 (5) |
C9—C19 | 1.545 (3) | C20—H20 | 0.9300 |
C9—C14 | 1.545 (3) | C21—C22 | 1.393 (4) |
N10—C11 | 1.453 (4) | C21—H21 | 0.9300 |
N10—C12 | 1.476 (3) | C22—C23 | 1.415 (4) |
C11—H11A | 0.9600 | C23—N27 | 1.378 (3) |
C11—H11B | 0.9600 | C23—C24 | 1.393 (4) |
C11—H11C | 0.9600 | C24—C25 | 1.378 (4) |
C12—C13 | 1.513 (4) | C24—H24 | 0.9300 |
C12—H12A | 0.9700 | C25—H25 | 0.9300 |
C12—H12B | 0.9700 | N26—H26 | 0.8600 |
C13—C14 | 1.540 (3) | N27—H27 | 0.88 (4) |
C13—H13A | 0.9700 | | |
| | | |
H1W—O1—H2W | 105 (2) | C22—C14—C9 | 109.39 (19) |
C3—C2—C7 | 120.5 (2) | C15—C14—C9 | 105.41 (18) |
C3—C2—H2 | 119.7 | C13—C14—C9 | 110.03 (19) |
C7—C2—H2 | 119.7 | N26—C15—N16 | 115.0 (2) |
C2—C3—C4 | 120.7 (3) | N26—C15—C14 | 108.7 (2) |
C2—C3—H3 | 119.6 | N16—C15—C14 | 109.7 (2) |
C4—C3—H3 | 119.6 | N26—C15—H15 | 107.7 |
N26—C4—C5 | 120.9 (2) | N16—C15—H15 | 107.7 |
N26—C4—C3 | 120.1 (2) | C14—C15—H15 | 107.7 |
C5—C4—C3 | 119.0 (2) | C17—N16—C18 | 110.5 (3) |
C6—C5—C4 | 118.6 (2) | C17—N16—C15 | 113.4 (3) |
C6—C5—C9 | 122.5 (2) | C18—N16—C15 | 112.3 (2) |
C4—C5—C9 | 118.8 (2) | N16—C17—H17A | 109.5 |
C7—C6—C5 | 122.4 (3) | N16—C17—H17B | 109.5 |
C7—C6—H6 | 118.8 | H17A—C17—H17B | 109.5 |
C5—C6—H6 | 118.8 | N16—C17—H17C | 109.5 |
C2—C7—C6 | 118.7 (3) | H17A—C17—H17C | 109.5 |
C2—C7—H7 | 120.7 | H17B—C17—H17C | 109.5 |
C6—C7—H7 | 120.7 | N16—C18—C19 | 110.4 (2) |
N27—C8—N10 | 113.37 (18) | N16—C18—H18A | 109.6 |
N27—C8—C9 | 109.41 (19) | C19—C18—H18A | 109.6 |
N10—C8—C9 | 109.95 (18) | N16—C18—H18B | 109.6 |
N27—C8—H8 | 108.0 | C19—C18—H18B | 109.6 |
N10—C8—H8 | 108.0 | H18A—C18—H18B | 108.1 |
C9—C8—H8 | 108.0 | C18—C19—C9 | 111.8 (2) |
C5—C9—C8 | 111.85 (19) | C18—C19—H19A | 109.3 |
C5—C9—C19 | 108.01 (17) | C9—C19—H19A | 109.3 |
C8—C9—C19 | 111.4 (2) | C18—C19—H19B | 109.3 |
C5—C9—C14 | 109.04 (18) | C9—C19—H19B | 109.3 |
C8—C9—C14 | 105.75 (17) | H19A—C19—H19B | 107.9 |
C19—C9—C14 | 110.74 (19) | C25—C20—C21 | 120.0 (3) |
C11—N10—C12 | 109.8 (2) | C25—C20—H20 | 120.0 |
C11—N10—C8 | 110.5 (2) | C21—C20—H20 | 120.0 |
C12—N10—C8 | 111.48 (18) | C20—C21—C22 | 122.0 (3) |
N10—C11—H11A | 109.5 | C20—C21—H21 | 119.0 |
N10—C11—H11B | 109.5 | C22—C21—H21 | 119.0 |
H11A—C11—H11B | 109.5 | C21—C22—C23 | 117.4 (3) |
N10—C11—H11C | 109.5 | C21—C22—C14 | 123.4 (3) |
H11A—C11—H11C | 109.5 | C23—C22—C14 | 119.0 (2) |
H11B—C11—H11C | 109.5 | N27—C23—C24 | 119.9 (3) |
N10—C12—C13 | 111.09 (19) | N27—C23—C22 | 120.2 (2) |
N10—C12—H12A | 109.4 | C24—C23—C22 | 119.9 (2) |
C13—C12—H12A | 109.4 | C25—C24—C23 | 121.0 (3) |
N10—C12—H12B | 109.4 | C25—C24—H24 | 119.5 |
C13—C12—H12B | 109.4 | C23—C24—H24 | 119.5 |
H12A—C12—H12B | 108.0 | C20—C25—C24 | 119.7 (3) |
C12—C13—C14 | 111.5 (2) | C20—C25—H25 | 120.2 |
C12—C13—H13A | 109.3 | C24—C25—H25 | 120.2 |
C14—C13—H13A | 109.3 | C4—N26—C15 | 121.6 (2) |
C12—C13—H13B | 109.3 | C4—N26—H26 | 119.2 |
C14—C13—H13B | 109.3 | C15—N26—H26 | 119.2 |
H13A—C13—H13B | 108.0 | C23—N27—C8 | 122.2 (2) |
C22—C14—C15 | 112.7 (2) | C23—N27—H27 | 118 (2) |
C22—C14—C13 | 108.44 (19) | C8—N27—H27 | 119 (2) |
C15—C14—C13 | 110.8 (2) | | |
| | | |
C7—C2—C3—C4 | −0.3 (4) | C22—C14—C15—N26 | 55.8 (3) |
C2—C3—C4—N26 | −177.7 (3) | C13—C14—C15—N26 | 177.57 (19) |
C2—C3—C4—C5 | 2.5 (4) | C9—C14—C15—N26 | −63.4 (3) |
N26—C4—C5—C6 | 176.8 (2) | C22—C14—C15—N16 | −177.60 (19) |
C3—C4—C5—C6 | −3.4 (3) | C13—C14—C15—N16 | −55.9 (3) |
N26—C4—C5—C9 | 1.0 (4) | C9—C14—C15—N16 | 63.1 (2) |
C3—C4—C5—C9 | −179.2 (2) | N26—C15—N16—C17 | −68.1 (3) |
C4—C5—C6—C7 | 2.2 (4) | C14—C15—N16—C17 | 169.0 (3) |
C9—C5—C6—C7 | 177.9 (2) | N26—C15—N16—C18 | 58.0 (3) |
C3—C2—C7—C6 | −1.0 (4) | C14—C15—N16—C18 | −64.9 (3) |
C5—C6—C7—C2 | 0.0 (4) | C17—N16—C18—C19 | −175.0 (3) |
C6—C5—C9—C8 | 37.0 (3) | C15—N16—C18—C19 | 57.3 (3) |
C4—C5—C9—C8 | −147.4 (2) | N16—C18—C19—C9 | −51.5 (3) |
C6—C5—C9—C19 | −86.0 (3) | C5—C9—C19—C18 | −65.1 (3) |
C4—C5—C9—C19 | 89.6 (2) | C8—C9—C19—C18 | 171.67 (19) |
C6—C5—C9—C14 | 153.6 (2) | C14—C9—C19—C18 | 54.2 (2) |
C4—C5—C9—C14 | −30.8 (3) | C25—C20—C21—C22 | 0.5 (5) |
N27—C8—C9—C5 | 56.8 (2) | C20—C21—C22—C23 | 0.5 (4) |
N10—C8—C9—C5 | −178.13 (16) | C20—C21—C22—C14 | 175.6 (2) |
N27—C8—C9—C19 | 177.78 (18) | C15—C14—C22—C21 | 36.8 (3) |
N10—C8—C9—C19 | −57.1 (2) | C13—C14—C22—C21 | −86.3 (3) |
N27—C8—C9—C14 | −61.8 (2) | C9—C14—C22—C21 | 153.7 (2) |
N10—C8—C9—C14 | 63.3 (2) | C15—C14—C22—C23 | −148.2 (2) |
N27—C8—N10—C11 | −62.8 (3) | C13—C14—C22—C23 | 88.7 (3) |
C9—C8—N10—C11 | 174.4 (2) | C9—C14—C22—C23 | −31.3 (3) |
N27—C8—N10—C12 | 59.6 (3) | C21—C22—C23—N27 | 177.3 (2) |
C9—C8—N10—C12 | −63.2 (2) | C14—C22—C23—N27 | 2.0 (3) |
C11—N10—C12—C13 | 179.4 (2) | C21—C22—C23—C24 | −0.9 (3) |
C8—N10—C12—C13 | 56.5 (3) | C14—C22—C23—C24 | −176.2 (2) |
N10—C12—C13—C14 | −52.8 (3) | N27—C23—C24—C25 | −177.9 (2) |
C12—C13—C14—C22 | −63.8 (3) | C22—C23—C24—C25 | 0.4 (4) |
C12—C13—C14—C15 | 172.0 (2) | C21—C20—C25—C24 | −1.1 (5) |
C12—C13—C14—C9 | 55.8 (3) | C23—C24—C25—C20 | 0.7 (4) |
C5—C9—C14—C22 | −60.8 (2) | C5—C4—N26—C15 | −3.9 (4) |
C8—C9—C14—C22 | 59.6 (2) | C3—C4—N26—C15 | 176.3 (2) |
C19—C9—C14—C22 | −179.53 (19) | N16—C15—N26—C4 | −87.0 (3) |
C5—C9—C14—C15 | 60.6 (2) | C14—C15—N26—C4 | 36.4 (3) |
C8—C9—C14—C15 | −178.95 (19) | C24—C23—N27—C8 | 174.0 (2) |
C19—C9—C14—C15 | −58.1 (2) | C22—C23—N27—C8 | −4.2 (3) |
C5—C9—C14—C13 | −179.8 (2) | N10—C8—N27—C23 | −87.7 (3) |
C8—C9—C14—C13 | −59.4 (2) | C9—C8—N27—C23 | 35.4 (3) |
C19—C9—C14—C13 | 61.5 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1W···N10 | 0.91 (2) | 1.96 (2) | 2.872 (3) | 179 (3) |
N27—H27···O1i | 0.88 (4) | 2.21 (4) | 3.062 (4) | 165 (3) |
Symmetry code: (i) −x, y+1/2, −z+3/2. |