The title bis-amide derivative was obtained by the reaction between glutaric acid chloride and 2-nitroaniline. The two benzene rings are twisted by angles of 79.14 (7) and 19.02 (14)° in the two independent molecules. In the crystal, amide–amide interactions link the molecules into chains running along b-axis direction.
Supporting information
CCDC reference: 1578746
checkCIF/PLATON results
No syntax errors found
Datablock: I
Alert level C
PLAT242_ALERT_2_C Low 'MainMol' Ueq as Compared to Neighbors of N3 Check
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00403 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 5.119 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min). 8 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 12 Report
Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 8 Note
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note) 0.01 Degree
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 1 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check
PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check
PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 4 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 3 Info
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
8 ALERT level G = General information/check it is not something unexpected
4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
5 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS2013/1 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/6 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL2014/6 (Sheldrick, 2015).
N,
N'-bis(2-nitrophenyl)glutaramide
top
Crystal data top
C17H16N4O6 | Z = 4 |
Mr = 372.34 | F(000) = 776 |
Triclinic, P1 | Dx = 1.447 Mg m−3 |
a = 9.625 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.673 (1) Å | Cell parameters from 2127 reflections |
c = 18.500 (2) Å | θ = 2.9–27.7° |
α = 95.37 (1)° | µ = 0.11 mm−1 |
β = 93.38 (1)° | T = 293 K |
γ = 92.77 (1)° | Rod, yellow |
V = 1709.3 (3) Å3 | 0.48 × 0.26 × 0.06 mm |
Data collection top
Oxford Diffraction Xcalibur
with Sapphire CCD diffractometer | 3877 reflections with I > 2σ(I) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.030 |
Rotation method data acquisition using ω scans. | θmax = 25.4°, θmin = 2.9° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −11→11 |
Tmin = 0.948, Tmax = 0.993 | k = −11→6 |
10696 measured reflections | l = −20→22 |
6248 independent reflections | |
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)] = 0.058 | Hydrogen site location: mixed |
wR(F2) = 0.158 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0698P)2 + 0.4948P] where P = (Fo2 + 2Fc2)/3 |
6248 reflections | (Δ/σ)max < 0.001 |
499 parameters | Δρmax = 0.27 e Å−3 |
4 restraints | Δρmin = −0.21 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.3147 (3) | 0.67820 (19) | 0.05292 (11) | 0.0655 (7) | |
O2 | 0.2237 (2) | 0.73540 (16) | 0.33207 (10) | 0.0451 (5) | |
O3 | 0.0896 (3) | 0.2146 (3) | −0.18879 (14) | 0.1000 (10) | |
O4 | 0.0869 (3) | 0.2646 (3) | −0.07551 (13) | 0.0799 (8) | |
O5 | −0.0882 (2) | 0.6967 (2) | 0.35971 (12) | 0.0655 (6) | |
O6 | −0.0156 (2) | 0.9019 (2) | 0.40685 (13) | 0.0644 (6) | |
N1 | 0.2543 (3) | 0.4663 (2) | −0.00794 (13) | 0.0491 (6) | |
H1N | 0.206 (3) | 0.391 (2) | −0.0022 (16) | 0.059* | |
N2 | 0.1565 (3) | 0.5376 (2) | 0.37960 (12) | 0.0408 (6) | |
H2N | 0.154 (3) | 0.4480 (18) | 0.3730 (15) | 0.049* | |
N3 | 0.1320 (3) | 0.2859 (3) | −0.13395 (15) | 0.0515 (6) | |
N4 | −0.0203 (2) | 0.7745 (2) | 0.40554 (13) | 0.0452 (6) | |
C1 | 0.2958 (3) | 0.4828 (3) | −0.07765 (14) | 0.0393 (6) | |
C2 | 0.2399 (3) | 0.3959 (3) | −0.13878 (15) | 0.0408 (7) | |
C3 | 0.2840 (3) | 0.4113 (3) | −0.20821 (16) | 0.0543 (8) | |
H3 | 0.2461 | 0.3520 | −0.2477 | 0.065* | |
C4 | 0.3825 (4) | 0.5128 (4) | −0.21869 (18) | 0.0607 (9) | |
H4 | 0.4111 | 0.5237 | −0.2651 | 0.073* | |
C5 | 0.4389 (3) | 0.5990 (3) | −0.15941 (18) | 0.0551 (8) | |
H5 | 0.5061 | 0.6682 | −0.1663 | 0.066* | |
C6 | 0.3978 (3) | 0.5847 (3) | −0.09057 (17) | 0.0485 (7) | |
H6 | 0.4384 | 0.6437 | −0.0517 | 0.058* | |
C7 | 0.2653 (3) | 0.5604 (3) | 0.05253 (15) | 0.0424 (7) | |
C8 | 0.2078 (3) | 0.5029 (3) | 0.11788 (15) | 0.0480 (7) | |
H8A | 0.2476 | 0.4141 | 0.1238 | 0.058* | |
H8B | 0.1079 | 0.4858 | 0.1088 | 0.058* | |
C9 | 0.2354 (3) | 0.5960 (3) | 0.18866 (14) | 0.0441 (7) | |
H9A | 0.3341 | 0.6228 | 0.1956 | 0.053* | |
H9B | 0.1850 | 0.6800 | 0.1859 | 0.053* | |
C10 | 0.1911 (4) | 0.5236 (3) | 0.25192 (15) | 0.0541 (8) | |
H10A | 0.2503 | 0.4462 | 0.2572 | 0.065* | |
H10B | 0.0966 | 0.4849 | 0.2406 | 0.065* | |
C11 | 0.1953 (3) | 0.6099 (2) | 0.32375 (14) | 0.0361 (6) | |
C12 | 0.1367 (3) | 0.5978 (2) | 0.45035 (14) | 0.0336 (6) | |
C13 | 0.0578 (3) | 0.7132 (3) | 0.46469 (14) | 0.0360 (6) | |
C14 | 0.0414 (3) | 0.7718 (3) | 0.53445 (16) | 0.0482 (8) | |
H14 | −0.0110 | 0.8496 | 0.5418 | 0.058* | |
C15 | 0.1025 (3) | 0.7150 (3) | 0.59281 (16) | 0.0548 (8) | |
H15 | 0.0925 | 0.7541 | 0.6400 | 0.066* | |
C16 | 0.1794 (3) | 0.5988 (3) | 0.58054 (16) | 0.0546 (8) | |
H16 | 0.2198 | 0.5586 | 0.6198 | 0.065* | |
C17 | 0.1970 (3) | 0.5415 (3) | 0.51009 (16) | 0.0451 (7) | |
H17 | 0.2501 | 0.4642 | 0.5029 | 0.054* | |
O7 | 0.3045 (3) | 0.17649 (19) | 0.05705 (11) | 0.0663 (7) | |
O8 | 0.2036 (2) | 0.23692 (17) | 0.33766 (10) | 0.0448 (5) | |
O9 | 0.0953 (3) | −0.2729 (3) | −0.19779 (13) | 0.0802 (8) | |
O10 | 0.0912 (3) | −0.2415 (2) | −0.08189 (13) | 0.0700 (7) | |
O11 | 0.5169 (2) | 0.2177 (2) | 0.34074 (12) | 0.0629 (6) | |
O12 | 0.4749 (2) | 0.41508 (19) | 0.39786 (11) | 0.0568 (6) | |
N5 | 0.2408 (3) | −0.0328 (2) | −0.00706 (13) | 0.0455 (6) | |
H5N | 0.197 (3) | −0.112 (2) | −0.0042 (16) | 0.055* | |
N6 | 0.2854 (2) | 0.0364 (2) | 0.37197 (12) | 0.0376 (5) | |
H6N | 0.272 (3) | −0.0524 (18) | 0.3653 (14) | 0.045* | |
N7 | 0.1378 (3) | −0.2110 (2) | −0.13923 (15) | 0.0509 (6) | |
N8 | 0.4744 (2) | 0.2875 (2) | 0.39265 (13) | 0.0432 (6) | |
C18 | 0.2939 (3) | −0.0158 (3) | −0.07437 (14) | 0.0386 (6) | |
C19 | 0.2469 (3) | −0.1001 (3) | −0.13854 (15) | 0.0407 (7) | |
C20 | 0.3026 (3) | −0.0821 (3) | −0.20481 (16) | 0.0559 (8) | |
H20 | 0.2700 | −0.1393 | −0.2461 | 0.067* | |
C21 | 0.4051 (4) | 0.0189 (3) | −0.20990 (17) | 0.0592 (9) | |
H21 | 0.4422 | 0.0306 | −0.2544 | 0.071* | |
C22 | 0.4527 (3) | 0.1035 (3) | −0.14813 (17) | 0.0530 (8) | |
H22 | 0.5213 | 0.1733 | −0.1514 | 0.064* | |
C23 | 0.3996 (3) | 0.0855 (3) | −0.08174 (15) | 0.0463 (7) | |
H23 | 0.4351 | 0.1422 | −0.0408 | 0.056* | |
C24 | 0.2492 (3) | 0.0601 (3) | 0.05446 (15) | 0.0422 (7) | |
C25 | 0.1819 (3) | 0.0042 (3) | 0.11826 (14) | 0.0429 (7) | |
H25A | 0.2108 | −0.0894 | 0.1229 | 0.052* | |
H25B | 0.0815 | −0.0008 | 0.1089 | 0.052* | |
C26 | 0.2196 (3) | 0.0934 (3) | 0.18947 (14) | 0.0410 (7) | |
H26A | 0.1857 | 0.1855 | 0.1859 | 0.049* | |
H26B | 0.3202 | 0.1029 | 0.1975 | 0.049* | |
C27 | 0.1582 (3) | 0.0320 (3) | 0.25438 (14) | 0.0434 (7) | |
H27A | 0.0575 | 0.0352 | 0.2503 | 0.052* | |
H27B | 0.1811 | −0.0645 | 0.2545 | 0.052* | |
C28 | 0.2149 (3) | 0.1123 (2) | 0.32459 (14) | 0.0340 (6) | |
C29 | 0.3407 (3) | 0.0933 (2) | 0.44173 (14) | 0.0334 (6) | |
C30 | 0.4243 (3) | 0.2158 (2) | 0.45335 (14) | 0.0348 (6) | |
C31 | 0.4704 (3) | 0.2724 (3) | 0.52307 (16) | 0.0463 (7) | |
H31 | 0.5248 | 0.3553 | 0.5295 | 0.056* | |
C32 | 0.4354 (3) | 0.2058 (3) | 0.58253 (16) | 0.0539 (8) | |
H32 | 0.4655 | 0.2433 | 0.6293 | 0.065* | |
C33 | 0.3553 (3) | 0.0829 (3) | 0.57198 (16) | 0.0538 (8) | |
H33 | 0.3325 | 0.0367 | 0.6119 | 0.065* | |
C34 | 0.3083 (3) | 0.0273 (3) | 0.50262 (15) | 0.0448 (7) | |
H34 | 0.2542 | −0.0557 | 0.4967 | 0.054* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.111 (2) | 0.0311 (11) | 0.0515 (13) | −0.0148 (12) | 0.0110 (12) | −0.0030 (9) |
O2 | 0.0691 (13) | 0.0216 (9) | 0.0441 (11) | −0.0060 (9) | 0.0122 (10) | −0.0012 (8) |
O3 | 0.111 (2) | 0.118 (2) | 0.0579 (17) | −0.0585 (19) | −0.0034 (15) | −0.0241 (15) |
O4 | 0.0968 (19) | 0.0837 (17) | 0.0527 (16) | −0.0467 (15) | 0.0060 (14) | −0.0017 (13) |
O5 | 0.0732 (16) | 0.0596 (14) | 0.0594 (15) | 0.0004 (12) | −0.0224 (12) | 0.0010 (11) |
O6 | 0.0776 (16) | 0.0361 (12) | 0.0822 (17) | 0.0150 (11) | 0.0116 (13) | 0.0100 (11) |
N1 | 0.0760 (19) | 0.0321 (12) | 0.0369 (14) | −0.0132 (12) | 0.0053 (12) | −0.0010 (11) |
N2 | 0.0626 (16) | 0.0208 (10) | 0.0395 (14) | 0.0009 (11) | 0.0136 (11) | 0.0003 (10) |
N3 | 0.0525 (16) | 0.0524 (15) | 0.0454 (16) | −0.0078 (13) | −0.0075 (13) | −0.0049 (13) |
N4 | 0.0467 (15) | 0.0373 (14) | 0.0520 (16) | 0.0063 (11) | 0.0070 (12) | 0.0020 (12) |
C1 | 0.0477 (17) | 0.0326 (14) | 0.0374 (16) | 0.0024 (12) | −0.0005 (13) | 0.0045 (12) |
C2 | 0.0438 (16) | 0.0379 (15) | 0.0400 (17) | 0.0018 (13) | −0.0035 (13) | 0.0032 (12) |
C3 | 0.062 (2) | 0.064 (2) | 0.0360 (18) | 0.0035 (17) | −0.0036 (15) | 0.0015 (15) |
C4 | 0.066 (2) | 0.074 (2) | 0.046 (2) | 0.0075 (19) | 0.0119 (17) | 0.0167 (17) |
C5 | 0.0527 (19) | 0.0509 (18) | 0.065 (2) | 0.0003 (15) | 0.0138 (16) | 0.0166 (16) |
C6 | 0.0539 (18) | 0.0393 (16) | 0.0509 (19) | −0.0059 (14) | 0.0024 (14) | 0.0017 (13) |
C7 | 0.0597 (19) | 0.0290 (14) | 0.0371 (16) | −0.0001 (13) | −0.0012 (13) | 0.0008 (12) |
C8 | 0.069 (2) | 0.0327 (15) | 0.0414 (17) | −0.0047 (14) | 0.0072 (15) | −0.0005 (12) |
C9 | 0.066 (2) | 0.0299 (14) | 0.0355 (16) | −0.0008 (13) | 0.0070 (14) | −0.0023 (12) |
C10 | 0.092 (2) | 0.0304 (15) | 0.0388 (17) | −0.0057 (15) | 0.0142 (16) | −0.0030 (12) |
C11 | 0.0445 (16) | 0.0273 (14) | 0.0367 (15) | 0.0010 (12) | 0.0086 (12) | 0.0016 (11) |
C12 | 0.0343 (14) | 0.0313 (13) | 0.0349 (15) | −0.0054 (11) | 0.0070 (11) | 0.0031 (11) |
C13 | 0.0397 (15) | 0.0316 (14) | 0.0355 (15) | −0.0061 (12) | 0.0040 (12) | 0.0003 (11) |
C14 | 0.0534 (18) | 0.0427 (16) | 0.0459 (18) | −0.0076 (14) | 0.0140 (15) | −0.0117 (14) |
C15 | 0.059 (2) | 0.067 (2) | 0.0349 (18) | −0.0189 (17) | 0.0070 (15) | −0.0050 (15) |
C16 | 0.0450 (18) | 0.077 (2) | 0.0412 (19) | −0.0155 (17) | −0.0016 (14) | 0.0176 (16) |
C17 | 0.0406 (16) | 0.0461 (17) | 0.0506 (19) | −0.0011 (13) | 0.0056 (14) | 0.0147 (14) |
O7 | 0.118 (2) | 0.0311 (11) | 0.0479 (13) | −0.0172 (12) | 0.0230 (13) | −0.0062 (9) |
O8 | 0.0652 (13) | 0.0241 (10) | 0.0440 (12) | 0.0046 (9) | −0.0024 (9) | 0.0004 (8) |
O9 | 0.0763 (17) | 0.0865 (17) | 0.0662 (17) | −0.0178 (14) | −0.0146 (13) | −0.0306 (13) |
O10 | 0.0775 (17) | 0.0651 (15) | 0.0622 (16) | −0.0260 (13) | 0.0001 (13) | −0.0028 (12) |
O11 | 0.0771 (16) | 0.0529 (13) | 0.0581 (14) | −0.0100 (11) | 0.0341 (12) | −0.0102 (11) |
O12 | 0.0718 (15) | 0.0289 (11) | 0.0686 (15) | −0.0100 (10) | 0.0086 (11) | 0.0032 (9) |
N5 | 0.0667 (17) | 0.0322 (12) | 0.0354 (14) | −0.0096 (12) | 0.0028 (12) | −0.0016 (10) |
N6 | 0.0516 (14) | 0.0201 (10) | 0.0393 (13) | −0.0046 (10) | −0.0016 (11) | 0.0001 (10) |
N7 | 0.0477 (15) | 0.0455 (14) | 0.0551 (17) | 0.0016 (12) | −0.0094 (13) | −0.0094 (13) |
N8 | 0.0452 (14) | 0.0335 (13) | 0.0494 (15) | −0.0088 (11) | 0.0105 (11) | −0.0035 (11) |
C18 | 0.0478 (17) | 0.0310 (14) | 0.0366 (16) | 0.0050 (12) | 0.0008 (13) | 0.0000 (11) |
C19 | 0.0445 (16) | 0.0370 (15) | 0.0385 (16) | 0.0058 (13) | −0.0044 (13) | −0.0048 (12) |
C20 | 0.065 (2) | 0.061 (2) | 0.0389 (19) | 0.0070 (17) | −0.0041 (15) | −0.0070 (15) |
C21 | 0.068 (2) | 0.067 (2) | 0.0425 (19) | 0.0055 (18) | 0.0116 (16) | 0.0030 (16) |
C22 | 0.057 (2) | 0.0473 (18) | 0.055 (2) | −0.0008 (15) | 0.0095 (16) | 0.0054 (15) |
C23 | 0.0570 (19) | 0.0407 (16) | 0.0390 (17) | −0.0041 (14) | 0.0023 (14) | −0.0036 (12) |
C24 | 0.0616 (19) | 0.0280 (14) | 0.0365 (16) | 0.0020 (13) | 0.0025 (13) | 0.0011 (12) |
C25 | 0.0571 (18) | 0.0327 (14) | 0.0378 (16) | −0.0053 (13) | 0.0037 (13) | 0.0010 (12) |
C26 | 0.0541 (18) | 0.0319 (14) | 0.0357 (16) | −0.0045 (13) | 0.0028 (13) | 0.0004 (11) |
C27 | 0.0599 (19) | 0.0324 (14) | 0.0361 (16) | −0.0104 (13) | −0.0020 (13) | 0.0042 (12) |
C28 | 0.0423 (15) | 0.0261 (14) | 0.0332 (15) | −0.0056 (11) | 0.0053 (12) | 0.0031 (11) |
C29 | 0.0340 (14) | 0.0278 (13) | 0.0381 (15) | 0.0042 (11) | 0.0017 (11) | 0.0006 (11) |
C30 | 0.0396 (15) | 0.0287 (13) | 0.0357 (15) | −0.0003 (11) | 0.0076 (12) | −0.0016 (11) |
C31 | 0.0464 (17) | 0.0389 (15) | 0.0501 (19) | −0.0007 (13) | −0.0019 (14) | −0.0092 (13) |
C32 | 0.059 (2) | 0.062 (2) | 0.0387 (18) | 0.0054 (17) | −0.0029 (15) | −0.0039 (15) |
C33 | 0.0527 (19) | 0.070 (2) | 0.0409 (18) | 0.0060 (16) | 0.0005 (14) | 0.0147 (15) |
C34 | 0.0448 (17) | 0.0435 (16) | 0.0466 (18) | −0.0057 (13) | −0.0011 (14) | 0.0127 (13) |
Geometric parameters (Å, º) top
O1—C7 | 1.213 (3) | O7—C24 | 1.218 (3) |
O2—C11 | 1.224 (3) | O8—C28 | 1.218 (3) |
O3—N3 | 1.210 (3) | O9—N7 | 1.225 (3) |
O4—N3 | 1.220 (3) | O10—N7 | 1.231 (3) |
O5—N4 | 1.217 (3) | O11—N8 | 1.223 (3) |
O6—N4 | 1.228 (3) | O12—N8 | 1.229 (3) |
N1—C7 | 1.370 (3) | N5—C24 | 1.378 (3) |
N1—C1 | 1.393 (3) | N5—C18 | 1.394 (3) |
N1—H1N | 0.863 (17) | N5—H5N | 0.862 (17) |
N2—C11 | 1.361 (3) | N6—C28 | 1.366 (3) |
N2—C12 | 1.409 (3) | N6—C29 | 1.417 (3) |
N2—H2N | 0.863 (17) | N6—H6N | 0.859 (16) |
N3—C2 | 1.463 (4) | N7—C19 | 1.464 (4) |
N4—C13 | 1.477 (4) | N8—C30 | 1.467 (3) |
C1—C6 | 1.404 (4) | C18—C23 | 1.399 (4) |
C1—C2 | 1.408 (4) | C18—C19 | 1.414 (4) |
C2—C3 | 1.395 (4) | C19—C20 | 1.389 (4) |
C3—C4 | 1.367 (4) | C20—C21 | 1.368 (4) |
C3—H3 | 0.9300 | C20—H20 | 0.9300 |
C4—C5 | 1.381 (4) | C21—C22 | 1.383 (4) |
C4—H4 | 0.9300 | C21—H21 | 0.9300 |
C5—C6 | 1.373 (4) | C22—C23 | 1.380 (4) |
C5—H5 | 0.9300 | C22—H22 | 0.9300 |
C6—H6 | 0.9300 | C23—H23 | 0.9300 |
C7—C8 | 1.501 (4) | C24—C25 | 1.510 (4) |
C8—C9 | 1.521 (3) | C25—C26 | 1.520 (3) |
C8—H8A | 0.9700 | C25—H25A | 0.9700 |
C8—H8B | 0.9700 | C25—H25B | 0.9700 |
C9—C10 | 1.492 (4) | C26—C27 | 1.525 (4) |
C9—H9A | 0.9700 | C26—H26A | 0.9700 |
C9—H9B | 0.9700 | C26—H26B | 0.9700 |
C10—C11 | 1.499 (4) | C27—C28 | 1.508 (3) |
C10—H10A | 0.9700 | C27—H27A | 0.9700 |
C10—H10B | 0.9700 | C27—H27B | 0.9700 |
C12—C17 | 1.386 (4) | C29—C34 | 1.389 (3) |
C12—C13 | 1.394 (4) | C29—C30 | 1.392 (3) |
C13—C14 | 1.381 (4) | C30—C31 | 1.392 (4) |
C14—C15 | 1.371 (4) | C31—C32 | 1.376 (4) |
C14—H14 | 0.9300 | C31—H31 | 0.9300 |
C15—C16 | 1.384 (4) | C32—C33 | 1.376 (4) |
C15—H15 | 0.9300 | C32—H32 | 0.9300 |
C16—C17 | 1.391 (4) | C33—C34 | 1.385 (4) |
C16—H16 | 0.9300 | C33—H33 | 0.9300 |
C17—H17 | 0.9300 | C34—H34 | 0.9300 |
| | | |
C7—N1—C1 | 128.9 (2) | C24—N5—C18 | 128.3 (2) |
C7—N1—H1N | 114 (2) | C24—N5—H5N | 117 (2) |
C1—N1—H1N | 117 (2) | C18—N5—H5N | 115 (2) |
C11—N2—C12 | 124.6 (2) | C28—N6—C29 | 123.0 (2) |
C11—N2—H2N | 117.7 (19) | C28—N6—H6N | 116.9 (18) |
C12—N2—H2N | 117.2 (19) | C29—N6—H6N | 116.9 (18) |
O3—N3—O4 | 120.3 (3) | O9—N7—O10 | 121.3 (3) |
O3—N3—C2 | 118.9 (3) | O9—N7—C19 | 118.5 (3) |
O4—N3—C2 | 120.7 (2) | O10—N7—C19 | 120.2 (2) |
O5—N4—O6 | 124.0 (3) | O11—N8—O12 | 123.6 (2) |
O5—N4—C13 | 118.4 (2) | O11—N8—C30 | 118.5 (2) |
O6—N4—C13 | 117.7 (2) | O12—N8—C30 | 117.9 (2) |
N1—C1—C6 | 121.9 (2) | N5—C18—C23 | 121.3 (2) |
N1—C1—C2 | 121.7 (2) | N5—C18—C19 | 122.6 (2) |
C6—C1—C2 | 116.4 (3) | C23—C18—C19 | 116.1 (3) |
C3—C2—C1 | 121.4 (3) | C20—C19—C18 | 121.5 (3) |
C3—C2—N3 | 116.0 (2) | C20—C19—N7 | 116.2 (3) |
C1—C2—N3 | 122.6 (3) | C18—C19—N7 | 122.3 (3) |
C4—C3—C2 | 120.5 (3) | C21—C20—C19 | 120.7 (3) |
C4—C3—H3 | 119.7 | C21—C20—H20 | 119.7 |
C2—C3—H3 | 119.7 | C19—C20—H20 | 119.7 |
C3—C4—C5 | 119.0 (3) | C20—C21—C22 | 119.2 (3) |
C3—C4—H4 | 120.5 | C20—C21—H21 | 120.4 |
C5—C4—H4 | 120.5 | C22—C21—H21 | 120.4 |
C6—C5—C4 | 121.3 (3) | C23—C22—C21 | 120.8 (3) |
C6—C5—H5 | 119.4 | C23—C22—H22 | 119.6 |
C4—C5—H5 | 119.4 | C21—C22—H22 | 119.6 |
C5—C6—C1 | 121.4 (3) | C22—C23—C18 | 121.8 (3) |
C5—C6—H6 | 119.3 | C22—C23—H23 | 119.1 |
C1—C6—H6 | 119.3 | C18—C23—H23 | 119.1 |
O1—C7—N1 | 123.5 (3) | O7—C24—N5 | 123.3 (3) |
O1—C7—C8 | 123.6 (2) | O7—C24—C25 | 123.1 (2) |
N1—C7—C8 | 112.9 (2) | N5—C24—C25 | 113.6 (2) |
C7—C8—C9 | 114.8 (2) | C24—C25—C26 | 112.7 (2) |
C7—C8—H8A | 108.6 | C24—C25—H25A | 109.0 |
C9—C8—H8A | 108.6 | C26—C25—H25A | 109.0 |
C7—C8—H8B | 108.6 | C24—C25—H25B | 109.0 |
C9—C8—H8B | 108.6 | C26—C25—H25B | 109.0 |
H8A—C8—H8B | 107.6 | H25A—C25—H25B | 107.8 |
C10—C9—C8 | 111.1 (2) | C25—C26—C27 | 112.5 (2) |
C10—C9—H9A | 109.4 | C25—C26—H26A | 109.1 |
C8—C9—H9A | 109.4 | C27—C26—H26A | 109.1 |
C10—C9—H9B | 109.4 | C25—C26—H26B | 109.1 |
C8—C9—H9B | 109.4 | C27—C26—H26B | 109.1 |
H9A—C9—H9B | 108.0 | H26A—C26—H26B | 107.8 |
C9—C10—C11 | 116.5 (2) | C28—C27—C26 | 110.5 (2) |
C9—C10—H10A | 108.2 | C28—C27—H27A | 109.6 |
C11—C10—H10A | 108.2 | C26—C27—H27A | 109.6 |
C9—C10—H10B | 108.2 | C28—C27—H27B | 109.6 |
C11—C10—H10B | 108.2 | C26—C27—H27B | 109.6 |
H10A—C10—H10B | 107.3 | H27A—C27—H27B | 108.1 |
O2—C11—N2 | 121.9 (2) | O8—C28—N6 | 121.8 (2) |
O2—C11—C10 | 124.2 (2) | O8—C28—C27 | 123.0 (2) |
N2—C11—C10 | 113.8 (2) | N6—C28—C27 | 115.2 (2) |
C17—C12—C13 | 116.7 (2) | C34—C29—C30 | 117.2 (2) |
C17—C12—N2 | 119.8 (2) | C34—C29—N6 | 119.5 (2) |
C13—C12—N2 | 123.5 (2) | C30—C29—N6 | 123.3 (2) |
C14—C13—C12 | 122.5 (3) | C31—C30—C29 | 121.6 (3) |
C14—C13—N4 | 116.1 (3) | C31—C30—N8 | 116.7 (2) |
C12—C13—N4 | 121.2 (2) | C29—C30—N8 | 121.6 (2) |
C15—C14—C13 | 119.9 (3) | C32—C31—C30 | 120.0 (3) |
C15—C14—H14 | 120.1 | C32—C31—H31 | 120.0 |
C13—C14—H14 | 120.1 | C30—C31—H31 | 120.0 |
C14—C15—C16 | 119.1 (3) | C33—C32—C31 | 119.2 (3) |
C14—C15—H15 | 120.5 | C33—C32—H32 | 120.4 |
C16—C15—H15 | 120.5 | C31—C32—H32 | 120.4 |
C15—C16—C17 | 120.7 (3) | C32—C33—C34 | 120.8 (3) |
C15—C16—H16 | 119.6 | C32—C33—H33 | 119.6 |
C17—C16—H16 | 119.6 | C34—C33—H33 | 119.6 |
C12—C17—C16 | 121.1 (3) | C33—C34—C29 | 121.2 (3) |
C12—C17—H17 | 119.4 | C33—C34—H34 | 119.4 |
C16—C17—H17 | 119.4 | C29—C34—H34 | 119.4 |
| | | |
C7—N1—C1—C6 | 22.1 (5) | C24—N5—C18—C23 | 19.3 (4) |
C7—N1—C1—C2 | −159.5 (3) | C24—N5—C18—C19 | −161.9 (3) |
N1—C1—C2—C3 | −178.7 (3) | N5—C18—C19—C20 | −179.2 (3) |
C6—C1—C2—C3 | −0.2 (4) | C23—C18—C19—C20 | −0.3 (4) |
N1—C1—C2—N3 | 2.0 (4) | N5—C18—C19—N7 | 0.6 (4) |
C6—C1—C2—N3 | −179.4 (2) | C23—C18—C19—N7 | 179.5 (2) |
O3—N3—C2—C3 | 1.1 (4) | O9—N7—C19—C20 | −5.5 (4) |
O4—N3—C2—C3 | 180.0 (3) | O10—N7—C19—C20 | 173.9 (3) |
O3—N3—C2—C1 | −179.5 (3) | O9—N7—C19—C18 | 174.7 (3) |
O4—N3—C2—C1 | −0.7 (4) | O10—N7—C19—C18 | −5.9 (4) |
C1—C2—C3—C4 | −0.6 (4) | C18—C19—C20—C21 | −0.3 (4) |
N3—C2—C3—C4 | 178.7 (3) | N7—C19—C20—C21 | 179.9 (3) |
C2—C3—C4—C5 | 0.7 (5) | C19—C20—C21—C22 | −0.1 (5) |
C3—C4—C5—C6 | −0.1 (5) | C20—C21—C22—C23 | 1.0 (5) |
C4—C5—C6—C1 | −0.6 (5) | C21—C22—C23—C18 | −1.6 (5) |
N1—C1—C6—C5 | 179.3 (3) | N5—C18—C23—C22 | −179.8 (3) |
C2—C1—C6—C5 | 0.8 (4) | C19—C18—C23—C22 | 1.2 (4) |
C1—N1—C7—O1 | 0.7 (5) | C18—N5—C24—O7 | 2.0 (5) |
C1—N1—C7—C8 | 179.8 (3) | C18—N5—C24—C25 | −178.7 (3) |
O1—C7—C8—C9 | −8.9 (4) | O7—C24—C25—C26 | −13.5 (4) |
N1—C7—C8—C9 | 172.0 (3) | N5—C24—C25—C26 | 167.2 (2) |
C7—C8—C9—C10 | −172.7 (3) | C24—C25—C26—C27 | −176.7 (2) |
C8—C9—C10—C11 | −172.3 (3) | C25—C26—C27—C28 | 171.9 (2) |
C12—N2—C11—O2 | 4.0 (4) | C29—N6—C28—O8 | 5.2 (4) |
C12—N2—C11—C10 | −172.6 (3) | C29—N6—C28—C27 | −177.3 (2) |
C9—C10—C11—O2 | 4.8 (5) | C26—C27—C28—O8 | 57.3 (4) |
C9—C10—C11—N2 | −178.7 (3) | C26—C27—C28—N6 | −120.2 (3) |
C11—N2—C12—C17 | −131.7 (3) | C28—N6—C29—C34 | 127.7 (3) |
C11—N2—C12—C13 | 48.6 (4) | C28—N6—C29—C30 | −50.6 (4) |
C17—C12—C13—C14 | 1.3 (4) | C34—C29—C30—C31 | −1.9 (4) |
N2—C12—C13—C14 | −179.0 (2) | N6—C29—C30—C31 | 176.4 (2) |
C17—C12—C13—N4 | −175.0 (2) | C34—C29—C30—N8 | 174.8 (2) |
N2—C12—C13—N4 | 4.7 (4) | N6—C29—C30—N8 | −6.9 (4) |
O5—N4—C13—C14 | −131.3 (3) | O11—N8—C30—C31 | 134.3 (3) |
O6—N4—C13—C14 | 46.7 (3) | O12—N8—C30—C31 | −43.7 (3) |
O5—N4—C13—C12 | 45.2 (4) | O11—N8—C30—C29 | −42.5 (4) |
O6—N4—C13—C12 | −136.7 (3) | O12—N8—C30—C29 | 139.5 (3) |
C12—C13—C14—C15 | −0.9 (4) | C29—C30—C31—C32 | 1.2 (4) |
N4—C13—C14—C15 | 175.5 (2) | N8—C30—C31—C32 | −175.7 (3) |
C13—C14—C15—C16 | −0.3 (4) | C30—C31—C32—C33 | 0.3 (4) |
C14—C15—C16—C17 | 1.2 (4) | C31—C32—C33—C34 | −0.9 (5) |
C13—C12—C17—C16 | −0.4 (4) | C32—C33—C34—C29 | 0.1 (4) |
N2—C12—C17—C16 | 179.9 (2) | C30—C29—C34—C33 | 1.3 (4) |
C15—C16—C17—C12 | −0.9 (4) | N6—C29—C34—C33 | −177.1 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O4 | 0.86 (2) | 2.01 (3) | 2.639 (3) | 130 (3) |
N2—H2N···O8 | 0.86 (2) | 2.17 (2) | 3.002 (3) | 162 (3) |
C3—H3···O5i | 0.93 | 2.49 | 3.337 (4) | 151 |
C14—H14···O6ii | 0.93 | 2.50 | 3.267 (3) | 140 |
N5—H5N···O10 | 0.86 (2) | 2.01 (3) | 2.651 (3) | 130 (3) |
N6—H6N···O2iii | 0.86 (2) | 2.11 (2) | 2.959 (3) | 171 (3) |
C27—H27B···O2iii | 0.97 | 2.55 | 3.396 (3) | 146 |
C31—H31···O12iv | 0.93 | 2.49 | 3.238 (3) | 138 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x, −y+2, −z+1; (iii) x, y−1, z; (iv) −x+1, −y+1, −z+1. |