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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989018013075/zl2738sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989018013075/zl2738Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989018013075/zl2738Isup3.cml
Supplementary material

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

Computing details top

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
C17H16N4O6Z = 4
Mr = 372.34F(000) = 776
Triclinic, P1Dx = 1.447 Mg m3
a = 9.625 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.673 (1) ÅCell parameters from 2127 reflections
c = 18.500 (2) Åθ = 2.9–27.7°
α = 95.37 (1)°µ = 0.11 mm1
β = 93.38 (1)°T = 293 K
γ = 92.77 (1)°Rod, yellow
V = 1709.3 (3) Å30.48 × 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 SourceRint = 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 = 1111
Tmin = 0.948, Tmax = 0.993k = 116
10696 measured reflectionsl = 2022
6248 independent reflections
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)] = 0.058Hydrogen site location: mixed
wR(F2) = 0.158H 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 parametersΔρmax = 0.27 e Å3
4 restraintsΔρmin = 0.21 e Å3
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
xyzUiso*/Ueq
O10.3147 (3)0.67820 (19)0.05292 (11)0.0655 (7)
O20.2237 (2)0.73540 (16)0.33207 (10)0.0451 (5)
O30.0896 (3)0.2146 (3)0.18879 (14)0.1000 (10)
O40.0869 (3)0.2646 (3)0.07551 (13)0.0799 (8)
O50.0882 (2)0.6967 (2)0.35971 (12)0.0655 (6)
O60.0156 (2)0.9019 (2)0.40685 (13)0.0644 (6)
N10.2543 (3)0.4663 (2)0.00794 (13)0.0491 (6)
H1N0.206 (3)0.391 (2)0.0022 (16)0.059*
N20.1565 (3)0.5376 (2)0.37960 (12)0.0408 (6)
H2N0.154 (3)0.4480 (18)0.3730 (15)0.049*
N30.1320 (3)0.2859 (3)0.13395 (15)0.0515 (6)
N40.0203 (2)0.7745 (2)0.40554 (13)0.0452 (6)
C10.2958 (3)0.4828 (3)0.07765 (14)0.0393 (6)
C20.2399 (3)0.3959 (3)0.13878 (15)0.0408 (7)
C30.2840 (3)0.4113 (3)0.20821 (16)0.0543 (8)
H30.24610.35200.24770.065*
C40.3825 (4)0.5128 (4)0.21869 (18)0.0607 (9)
H40.41110.52370.26510.073*
C50.4389 (3)0.5990 (3)0.15941 (18)0.0551 (8)
H50.50610.66820.16630.066*
C60.3978 (3)0.5847 (3)0.09057 (17)0.0485 (7)
H60.43840.64370.05170.058*
C70.2653 (3)0.5604 (3)0.05253 (15)0.0424 (7)
C80.2078 (3)0.5029 (3)0.11788 (15)0.0480 (7)
H8A0.24760.41410.12380.058*
H8B0.10790.48580.10880.058*
C90.2354 (3)0.5960 (3)0.18866 (14)0.0441 (7)
H9A0.33410.62280.19560.053*
H9B0.18500.68000.18590.053*
C100.1911 (4)0.5236 (3)0.25192 (15)0.0541 (8)
H10A0.25030.44620.25720.065*
H10B0.09660.48490.24060.065*
C110.1953 (3)0.6099 (2)0.32375 (14)0.0361 (6)
C120.1367 (3)0.5978 (2)0.45035 (14)0.0336 (6)
C130.0578 (3)0.7132 (3)0.46469 (14)0.0360 (6)
C140.0414 (3)0.7718 (3)0.53445 (16)0.0482 (8)
H140.01100.84960.54180.058*
C150.1025 (3)0.7150 (3)0.59281 (16)0.0548 (8)
H150.09250.75410.64000.066*
C160.1794 (3)0.5988 (3)0.58054 (16)0.0546 (8)
H160.21980.55860.61980.065*
C170.1970 (3)0.5415 (3)0.51009 (16)0.0451 (7)
H170.25010.46420.50290.054*
O70.3045 (3)0.17649 (19)0.05705 (11)0.0663 (7)
O80.2036 (2)0.23692 (17)0.33766 (10)0.0448 (5)
O90.0953 (3)0.2729 (3)0.19779 (13)0.0802 (8)
O100.0912 (3)0.2415 (2)0.08189 (13)0.0700 (7)
O110.5169 (2)0.2177 (2)0.34074 (12)0.0629 (6)
O120.4749 (2)0.41508 (19)0.39786 (11)0.0568 (6)
N50.2408 (3)0.0328 (2)0.00706 (13)0.0455 (6)
H5N0.197 (3)0.112 (2)0.0042 (16)0.055*
N60.2854 (2)0.0364 (2)0.37197 (12)0.0376 (5)
H6N0.272 (3)0.0524 (18)0.3653 (14)0.045*
N70.1378 (3)0.2110 (2)0.13923 (15)0.0509 (6)
N80.4744 (2)0.2875 (2)0.39265 (13)0.0432 (6)
C180.2939 (3)0.0158 (3)0.07437 (14)0.0386 (6)
C190.2469 (3)0.1001 (3)0.13854 (15)0.0407 (7)
C200.3026 (3)0.0821 (3)0.20481 (16)0.0559 (8)
H200.27000.13930.24610.067*
C210.4051 (4)0.0189 (3)0.20990 (17)0.0592 (9)
H210.44220.03060.25440.071*
C220.4527 (3)0.1035 (3)0.14813 (17)0.0530 (8)
H220.52130.17330.15140.064*
C230.3996 (3)0.0855 (3)0.08174 (15)0.0463 (7)
H230.43510.14220.04080.056*
C240.2492 (3)0.0601 (3)0.05446 (15)0.0422 (7)
C250.1819 (3)0.0042 (3)0.11826 (14)0.0429 (7)
H25A0.21080.08940.12290.052*
H25B0.08150.00080.10890.052*
C260.2196 (3)0.0934 (3)0.18947 (14)0.0410 (7)
H26A0.18570.18550.18590.049*
H26B0.32020.10290.19750.049*
C270.1582 (3)0.0320 (3)0.25438 (14)0.0434 (7)
H27A0.05750.03520.25030.052*
H27B0.18110.06450.25450.052*
C280.2149 (3)0.1123 (2)0.32459 (14)0.0340 (6)
C290.3407 (3)0.0933 (2)0.44173 (14)0.0334 (6)
C300.4243 (3)0.2158 (2)0.45335 (14)0.0348 (6)
C310.4704 (3)0.2724 (3)0.52307 (16)0.0463 (7)
H310.52480.35530.52950.056*
C320.4354 (3)0.2058 (3)0.58253 (16)0.0539 (8)
H320.46550.24330.62930.065*
C330.3553 (3)0.0829 (3)0.57198 (16)0.0538 (8)
H330.33250.03670.61190.065*
C340.3083 (3)0.0273 (3)0.50262 (15)0.0448 (7)
H340.25420.05570.49670.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.111 (2)0.0311 (11)0.0515 (13)0.0148 (12)0.0110 (12)0.0030 (9)
O20.0691 (13)0.0216 (9)0.0441 (11)0.0060 (9)0.0122 (10)0.0012 (8)
O30.111 (2)0.118 (2)0.0579 (17)0.0585 (19)0.0034 (15)0.0241 (15)
O40.0968 (19)0.0837 (17)0.0527 (16)0.0467 (15)0.0060 (14)0.0017 (13)
O50.0732 (16)0.0596 (14)0.0594 (15)0.0004 (12)0.0224 (12)0.0010 (11)
O60.0776 (16)0.0361 (12)0.0822 (17)0.0150 (11)0.0116 (13)0.0100 (11)
N10.0760 (19)0.0321 (12)0.0369 (14)0.0132 (12)0.0053 (12)0.0010 (11)
N20.0626 (16)0.0208 (10)0.0395 (14)0.0009 (11)0.0136 (11)0.0003 (10)
N30.0525 (16)0.0524 (15)0.0454 (16)0.0078 (13)0.0075 (13)0.0049 (13)
N40.0467 (15)0.0373 (14)0.0520 (16)0.0063 (11)0.0070 (12)0.0020 (12)
C10.0477 (17)0.0326 (14)0.0374 (16)0.0024 (12)0.0005 (13)0.0045 (12)
C20.0438 (16)0.0379 (15)0.0400 (17)0.0018 (13)0.0035 (13)0.0032 (12)
C30.062 (2)0.064 (2)0.0360 (18)0.0035 (17)0.0036 (15)0.0015 (15)
C40.066 (2)0.074 (2)0.046 (2)0.0075 (19)0.0119 (17)0.0167 (17)
C50.0527 (19)0.0509 (18)0.065 (2)0.0003 (15)0.0138 (16)0.0166 (16)
C60.0539 (18)0.0393 (16)0.0509 (19)0.0059 (14)0.0024 (14)0.0017 (13)
C70.0597 (19)0.0290 (14)0.0371 (16)0.0001 (13)0.0012 (13)0.0008 (12)
C80.069 (2)0.0327 (15)0.0414 (17)0.0047 (14)0.0072 (15)0.0005 (12)
C90.066 (2)0.0299 (14)0.0355 (16)0.0008 (13)0.0070 (14)0.0023 (12)
C100.092 (2)0.0304 (15)0.0388 (17)0.0057 (15)0.0142 (16)0.0030 (12)
C110.0445 (16)0.0273 (14)0.0367 (15)0.0010 (12)0.0086 (12)0.0016 (11)
C120.0343 (14)0.0313 (13)0.0349 (15)0.0054 (11)0.0070 (11)0.0031 (11)
C130.0397 (15)0.0316 (14)0.0355 (15)0.0061 (12)0.0040 (12)0.0003 (11)
C140.0534 (18)0.0427 (16)0.0459 (18)0.0076 (14)0.0140 (15)0.0117 (14)
C150.059 (2)0.067 (2)0.0349 (18)0.0189 (17)0.0070 (15)0.0050 (15)
C160.0450 (18)0.077 (2)0.0412 (19)0.0155 (17)0.0016 (14)0.0176 (16)
C170.0406 (16)0.0461 (17)0.0506 (19)0.0011 (13)0.0056 (14)0.0147 (14)
O70.118 (2)0.0311 (11)0.0479 (13)0.0172 (12)0.0230 (13)0.0062 (9)
O80.0652 (13)0.0241 (10)0.0440 (12)0.0046 (9)0.0024 (9)0.0004 (8)
O90.0763 (17)0.0865 (17)0.0662 (17)0.0178 (14)0.0146 (13)0.0306 (13)
O100.0775 (17)0.0651 (15)0.0622 (16)0.0260 (13)0.0001 (13)0.0028 (12)
O110.0771 (16)0.0529 (13)0.0581 (14)0.0100 (11)0.0341 (12)0.0102 (11)
O120.0718 (15)0.0289 (11)0.0686 (15)0.0100 (10)0.0086 (11)0.0032 (9)
N50.0667 (17)0.0322 (12)0.0354 (14)0.0096 (12)0.0028 (12)0.0016 (10)
N60.0516 (14)0.0201 (10)0.0393 (13)0.0046 (10)0.0016 (11)0.0001 (10)
N70.0477 (15)0.0455 (14)0.0551 (17)0.0016 (12)0.0094 (13)0.0094 (13)
N80.0452 (14)0.0335 (13)0.0494 (15)0.0088 (11)0.0105 (11)0.0035 (11)
C180.0478 (17)0.0310 (14)0.0366 (16)0.0050 (12)0.0008 (13)0.0000 (11)
C190.0445 (16)0.0370 (15)0.0385 (16)0.0058 (13)0.0044 (13)0.0048 (12)
C200.065 (2)0.061 (2)0.0389 (19)0.0070 (17)0.0041 (15)0.0070 (15)
C210.068 (2)0.067 (2)0.0425 (19)0.0055 (18)0.0116 (16)0.0030 (16)
C220.057 (2)0.0473 (18)0.055 (2)0.0008 (15)0.0095 (16)0.0054 (15)
C230.0570 (19)0.0407 (16)0.0390 (17)0.0041 (14)0.0023 (14)0.0036 (12)
C240.0616 (19)0.0280 (14)0.0365 (16)0.0020 (13)0.0025 (13)0.0011 (12)
C250.0571 (18)0.0327 (14)0.0378 (16)0.0053 (13)0.0037 (13)0.0010 (12)
C260.0541 (18)0.0319 (14)0.0357 (16)0.0045 (13)0.0028 (13)0.0004 (11)
C270.0599 (19)0.0324 (14)0.0361 (16)0.0104 (13)0.0020 (13)0.0042 (12)
C280.0423 (15)0.0261 (14)0.0332 (15)0.0056 (11)0.0053 (12)0.0031 (11)
C290.0340 (14)0.0278 (13)0.0381 (15)0.0042 (11)0.0017 (11)0.0006 (11)
C300.0396 (15)0.0287 (13)0.0357 (15)0.0003 (11)0.0076 (12)0.0016 (11)
C310.0464 (17)0.0389 (15)0.0501 (19)0.0007 (13)0.0019 (14)0.0092 (13)
C320.059 (2)0.062 (2)0.0387 (18)0.0054 (17)0.0029 (15)0.0039 (15)
C330.0527 (19)0.070 (2)0.0409 (18)0.0060 (16)0.0005 (14)0.0147 (15)
C340.0448 (17)0.0435 (16)0.0466 (18)0.0057 (13)0.0011 (14)0.0127 (13)
Geometric parameters (Å, º) top
O1—C71.213 (3)O7—C241.218 (3)
O2—C111.224 (3)O8—C281.218 (3)
O3—N31.210 (3)O9—N71.225 (3)
O4—N31.220 (3)O10—N71.231 (3)
O5—N41.217 (3)O11—N81.223 (3)
O6—N41.228 (3)O12—N81.229 (3)
N1—C71.370 (3)N5—C241.378 (3)
N1—C11.393 (3)N5—C181.394 (3)
N1—H1N0.863 (17)N5—H5N0.862 (17)
N2—C111.361 (3)N6—C281.366 (3)
N2—C121.409 (3)N6—C291.417 (3)
N2—H2N0.863 (17)N6—H6N0.859 (16)
N3—C21.463 (4)N7—C191.464 (4)
N4—C131.477 (4)N8—C301.467 (3)
C1—C61.404 (4)C18—C231.399 (4)
C1—C21.408 (4)C18—C191.414 (4)
C2—C31.395 (4)C19—C201.389 (4)
C3—C41.367 (4)C20—C211.368 (4)
C3—H30.9300C20—H200.9300
C4—C51.381 (4)C21—C221.383 (4)
C4—H40.9300C21—H210.9300
C5—C61.373 (4)C22—C231.380 (4)
C5—H50.9300C22—H220.9300
C6—H60.9300C23—H230.9300
C7—C81.501 (4)C24—C251.510 (4)
C8—C91.521 (3)C25—C261.520 (3)
C8—H8A0.9700C25—H25A0.9700
C8—H8B0.9700C25—H25B0.9700
C9—C101.492 (4)C26—C271.525 (4)
C9—H9A0.9700C26—H26A0.9700
C9—H9B0.9700C26—H26B0.9700
C10—C111.499 (4)C27—C281.508 (3)
C10—H10A0.9700C27—H27A0.9700
C10—H10B0.9700C27—H27B0.9700
C12—C171.386 (4)C29—C341.389 (3)
C12—C131.394 (4)C29—C301.392 (3)
C13—C141.381 (4)C30—C311.392 (4)
C14—C151.371 (4)C31—C321.376 (4)
C14—H140.9300C31—H310.9300
C15—C161.384 (4)C32—C331.376 (4)
C15—H150.9300C32—H320.9300
C16—C171.391 (4)C33—C341.385 (4)
C16—H160.9300C33—H330.9300
C17—H170.9300C34—H340.9300
C7—N1—C1128.9 (2)C24—N5—C18128.3 (2)
C7—N1—H1N114 (2)C24—N5—H5N117 (2)
C1—N1—H1N117 (2)C18—N5—H5N115 (2)
C11—N2—C12124.6 (2)C28—N6—C29123.0 (2)
C11—N2—H2N117.7 (19)C28—N6—H6N116.9 (18)
C12—N2—H2N117.2 (19)C29—N6—H6N116.9 (18)
O3—N3—O4120.3 (3)O9—N7—O10121.3 (3)
O3—N3—C2118.9 (3)O9—N7—C19118.5 (3)
O4—N3—C2120.7 (2)O10—N7—C19120.2 (2)
O5—N4—O6124.0 (3)O11—N8—O12123.6 (2)
O5—N4—C13118.4 (2)O11—N8—C30118.5 (2)
O6—N4—C13117.7 (2)O12—N8—C30117.9 (2)
N1—C1—C6121.9 (2)N5—C18—C23121.3 (2)
N1—C1—C2121.7 (2)N5—C18—C19122.6 (2)
C6—C1—C2116.4 (3)C23—C18—C19116.1 (3)
C3—C2—C1121.4 (3)C20—C19—C18121.5 (3)
C3—C2—N3116.0 (2)C20—C19—N7116.2 (3)
C1—C2—N3122.6 (3)C18—C19—N7122.3 (3)
C4—C3—C2120.5 (3)C21—C20—C19120.7 (3)
C4—C3—H3119.7C21—C20—H20119.7
C2—C3—H3119.7C19—C20—H20119.7
C3—C4—C5119.0 (3)C20—C21—C22119.2 (3)
C3—C4—H4120.5C20—C21—H21120.4
C5—C4—H4120.5C22—C21—H21120.4
C6—C5—C4121.3 (3)C23—C22—C21120.8 (3)
C6—C5—H5119.4C23—C22—H22119.6
C4—C5—H5119.4C21—C22—H22119.6
C5—C6—C1121.4 (3)C22—C23—C18121.8 (3)
C5—C6—H6119.3C22—C23—H23119.1
C1—C6—H6119.3C18—C23—H23119.1
O1—C7—N1123.5 (3)O7—C24—N5123.3 (3)
O1—C7—C8123.6 (2)O7—C24—C25123.1 (2)
N1—C7—C8112.9 (2)N5—C24—C25113.6 (2)
C7—C8—C9114.8 (2)C24—C25—C26112.7 (2)
C7—C8—H8A108.6C24—C25—H25A109.0
C9—C8—H8A108.6C26—C25—H25A109.0
C7—C8—H8B108.6C24—C25—H25B109.0
C9—C8—H8B108.6C26—C25—H25B109.0
H8A—C8—H8B107.6H25A—C25—H25B107.8
C10—C9—C8111.1 (2)C25—C26—C27112.5 (2)
C10—C9—H9A109.4C25—C26—H26A109.1
C8—C9—H9A109.4C27—C26—H26A109.1
C10—C9—H9B109.4C25—C26—H26B109.1
C8—C9—H9B109.4C27—C26—H26B109.1
H9A—C9—H9B108.0H26A—C26—H26B107.8
C9—C10—C11116.5 (2)C28—C27—C26110.5 (2)
C9—C10—H10A108.2C28—C27—H27A109.6
C11—C10—H10A108.2C26—C27—H27A109.6
C9—C10—H10B108.2C28—C27—H27B109.6
C11—C10—H10B108.2C26—C27—H27B109.6
H10A—C10—H10B107.3H27A—C27—H27B108.1
O2—C11—N2121.9 (2)O8—C28—N6121.8 (2)
O2—C11—C10124.2 (2)O8—C28—C27123.0 (2)
N2—C11—C10113.8 (2)N6—C28—C27115.2 (2)
C17—C12—C13116.7 (2)C34—C29—C30117.2 (2)
C17—C12—N2119.8 (2)C34—C29—N6119.5 (2)
C13—C12—N2123.5 (2)C30—C29—N6123.3 (2)
C14—C13—C12122.5 (3)C31—C30—C29121.6 (3)
C14—C13—N4116.1 (3)C31—C30—N8116.7 (2)
C12—C13—N4121.2 (2)C29—C30—N8121.6 (2)
C15—C14—C13119.9 (3)C32—C31—C30120.0 (3)
C15—C14—H14120.1C32—C31—H31120.0
C13—C14—H14120.1C30—C31—H31120.0
C14—C15—C16119.1 (3)C33—C32—C31119.2 (3)
C14—C15—H15120.5C33—C32—H32120.4
C16—C15—H15120.5C31—C32—H32120.4
C15—C16—C17120.7 (3)C32—C33—C34120.8 (3)
C15—C16—H16119.6C32—C33—H33119.6
C17—C16—H16119.6C34—C33—H33119.6
C12—C17—C16121.1 (3)C33—C34—C29121.2 (3)
C12—C17—H17119.4C33—C34—H34119.4
C16—C17—H17119.4C29—C34—H34119.4
C7—N1—C1—C622.1 (5)C24—N5—C18—C2319.3 (4)
C7—N1—C1—C2159.5 (3)C24—N5—C18—C19161.9 (3)
N1—C1—C2—C3178.7 (3)N5—C18—C19—C20179.2 (3)
C6—C1—C2—C30.2 (4)C23—C18—C19—C200.3 (4)
N1—C1—C2—N32.0 (4)N5—C18—C19—N70.6 (4)
C6—C1—C2—N3179.4 (2)C23—C18—C19—N7179.5 (2)
O3—N3—C2—C31.1 (4)O9—N7—C19—C205.5 (4)
O4—N3—C2—C3180.0 (3)O10—N7—C19—C20173.9 (3)
O3—N3—C2—C1179.5 (3)O9—N7—C19—C18174.7 (3)
O4—N3—C2—C10.7 (4)O10—N7—C19—C185.9 (4)
C1—C2—C3—C40.6 (4)C18—C19—C20—C210.3 (4)
N3—C2—C3—C4178.7 (3)N7—C19—C20—C21179.9 (3)
C2—C3—C4—C50.7 (5)C19—C20—C21—C220.1 (5)
C3—C4—C5—C60.1 (5)C20—C21—C22—C231.0 (5)
C4—C5—C6—C10.6 (5)C21—C22—C23—C181.6 (5)
N1—C1—C6—C5179.3 (3)N5—C18—C23—C22179.8 (3)
C2—C1—C6—C50.8 (4)C19—C18—C23—C221.2 (4)
C1—N1—C7—O10.7 (5)C18—N5—C24—O72.0 (5)
C1—N1—C7—C8179.8 (3)C18—N5—C24—C25178.7 (3)
O1—C7—C8—C98.9 (4)O7—C24—C25—C2613.5 (4)
N1—C7—C8—C9172.0 (3)N5—C24—C25—C26167.2 (2)
C7—C8—C9—C10172.7 (3)C24—C25—C26—C27176.7 (2)
C8—C9—C10—C11172.3 (3)C25—C26—C27—C28171.9 (2)
C12—N2—C11—O24.0 (4)C29—N6—C28—O85.2 (4)
C12—N2—C11—C10172.6 (3)C29—N6—C28—C27177.3 (2)
C9—C10—C11—O24.8 (5)C26—C27—C28—O857.3 (4)
C9—C10—C11—N2178.7 (3)C26—C27—C28—N6120.2 (3)
C11—N2—C12—C17131.7 (3)C28—N6—C29—C34127.7 (3)
C11—N2—C12—C1348.6 (4)C28—N6—C29—C3050.6 (4)
C17—C12—C13—C141.3 (4)C34—C29—C30—C311.9 (4)
N2—C12—C13—C14179.0 (2)N6—C29—C30—C31176.4 (2)
C17—C12—C13—N4175.0 (2)C34—C29—C30—N8174.8 (2)
N2—C12—C13—N44.7 (4)N6—C29—C30—N86.9 (4)
O5—N4—C13—C14131.3 (3)O11—N8—C30—C31134.3 (3)
O6—N4—C13—C1446.7 (3)O12—N8—C30—C3143.7 (3)
O5—N4—C13—C1245.2 (4)O11—N8—C30—C2942.5 (4)
O6—N4—C13—C12136.7 (3)O12—N8—C30—C29139.5 (3)
C12—C13—C14—C150.9 (4)C29—C30—C31—C321.2 (4)
N4—C13—C14—C15175.5 (2)N8—C30—C31—C32175.7 (3)
C13—C14—C15—C160.3 (4)C30—C31—C32—C330.3 (4)
C14—C15—C16—C171.2 (4)C31—C32—C33—C340.9 (5)
C13—C12—C17—C160.4 (4)C32—C33—C34—C290.1 (4)
N2—C12—C17—C16179.9 (2)C30—C29—C34—C331.3 (4)
C15—C16—C17—C120.9 (4)N6—C29—C34—C33177.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O40.86 (2)2.01 (3)2.639 (3)130 (3)
N2—H2N···O80.86 (2)2.17 (2)3.002 (3)162 (3)
C3—H3···O5i0.932.493.337 (4)151
C14—H14···O6ii0.932.503.267 (3)140
N5—H5N···O100.86 (2)2.01 (3)2.651 (3)130 (3)
N6—H6N···O2iii0.86 (2)2.11 (2)2.959 (3)171 (3)
C27—H27B···O2iii0.972.553.396 (3)146
C31—H31···O12iv0.932.493.238 (3)138
Symmetry codes: (i) x, y+1, z; (ii) x, y+2, z+1; (iii) x, y1, z; (iv) x+1, y+1, z+1.
 

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