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Three binary and one ternary charge-transfer complexes have been made using 1,3,5-tri­nitro­benzene, all of which show alternating donor and acceptor stacks, which have weak C—H...O hydrogen bonds perpendicular to the stacking axis. The final complex is a crystal engineering attempt to modify the packing of the stacks by inserting a third mol­ecule into the structure; this third mol­ecule features strong hydrogen bonds between the carb­oxy­lic acid group of the donor mol­ecule and the pyridine acceptor mol­ecule.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989018000245/eb2004sup1.cif
Contains datablocks I, II, III, IV, shelx

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989018000245/eb2004Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989018000245/eb2004IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989018000245/eb2004IIIsup4.hkl
Contains datablock III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989018000245/eb2004IVsup5.hkl
Contains datablock IV

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2056989018000245/eb2004sup6.pdf
Fingerprint plots

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989018000245/eb2004Isup7.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989018000245/eb2004IIsup8.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989018000245/eb2004IIIsup9.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989018000245/eb2004IVsup10.cml
Supplementary material

CCDC references: 1814637; 1814636; 1814635; 1814634

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • Mean [sigma](C-C) = 0.003 Å
  • Mean [sigma](C-C) = 0.004 Å
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.053
  • wR factor = 0.152
  • Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C PLAT334_ALERT_2_C Small Aver. Benzene C-C Dist C1 -C6 1.37 Ang. PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00411 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H22A ..O4 2.64 Ang. PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 2.712 Check
Alert level G PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 2 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 4 ALERT level C = Check. Ensure it is not caused by an omission or oversight 4 ALERT level G = General information/check it is not something unexpected 2 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 3 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
Datablock: II
Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H6 ..O5 2.68 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H21 ..O1 2.65 Ang. PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 2.162 Check
Alert level G PLAT128_ALERT_4_G Alternate Setting for Input Space Group P21/c P21/n Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 12 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 3 ALERT level C = Check. Ensure it is not caused by an omission or oversight 2 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Datablock: III

Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00437 Ang. PLAT412_ALERT_2_C Short Intra XH3 .. XHn H15 ..H18A .. 1.83 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H20 ..O3 2.64 Ang. PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 6.712 Check PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min). 9 Note PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 8 Report
Alert level G PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large 0.13 Report PLAT180_ALERT_4_G Check Cell Rounding: # of Values Ending with 0 = 3 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 10 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 6 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 6 ALERT level C = Check. Ensure it is not caused by an omission or oversight 4 ALERT level G = General information/check it is not something unexpected 0 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 4 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Datablock: IV
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low . 0.967 Why? PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00518 Ang. PLAT430_ALERT_2_C Short Inter D...A Contact O2 ..O9 . 2.90 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H26 ..O1 2.69 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H26 ..O2 2.72 Ang. PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 9.257 Check PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 2.297 Check PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min). 9 Note PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 122 Report
Alert level G PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size .... 0.63 mm PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 3 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ... 5 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 1 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 9 ALERT level C = Check. Ensure it is not caused by an omission or oversight 4 ALERT level G = General information/check it is not something unexpected 0 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 6 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

For all structures, data collection: APEX3 (Bruker, 2016); cell refinement: SAINT-Plus (Bruker, 2016); data reduction: SAINT-Plus and XPREP (Bruker, 2016). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (I); SHELXS97 (Sheldrick, 2015) for (II), (III), (IV). For all structures, program(s) used to refine structure: SHELXL2017/1 (Sheldrick, 2015). Molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) for (I); ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006) for (II), (III), (IV). For all structures, software used to prepare material for publication: WinGX publication routines (Farrugia, 2012).

1,3,5-Trinitrobenzene–1-(naphthalen-2-yl)ethan-1-one (1/1) (I) top
Crystal data top
C6H3N3O6·C12H10OF(000) = 792
Mr = 383.31Dx = 1.484 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1787 reflections
a = 16.6728 (10) Åθ = 2.5–19.9°
b = 6.8197 (3) ŵ = 0.12 mm1
c = 15.4419 (7) ÅT = 293 K
β = 102.217 (3)°Plate, yellow
V = 1716.03 (15) Å30.15 × 0.12 × 0.07 mm
Z = 4
Data collection top
Bruker D8 Venture Photon CCD area detector
diffractometer
1874 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.063
ω scansθmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1820
Tmin = 0.9, Tmax = 0.95k = 88
15612 measured reflectionsl = 1818
3195 independent reflections
Refinement top
Refinement on F20 constraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H-atom parameters constrained
wR(F2) = 0.152 w = 1/[σ2(Fo2) + (0.0652P)2 + 0.4622P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
3195 reflectionsΔρmax = 0.40 e Å3
254 parametersΔρmin = 0.28 e Å3
0 restraints
Special details top

Experimental. (SADABS; Sheldrick, 1996)

Geometry. All standard uncertainties (s.u.) (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u. are taken into account individually in the estimation of s.u. in distances, angles and torsion angles; correlations between s.u. in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u. is used for estimating s.u. involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.21511 (18)0.3392 (4)0.53179 (17)0.0389 (7)
C20.29340 (17)0.3382 (4)0.51644 (18)0.0405 (7)
H20.3389390.3136650.5614950.049*
C30.30078 (16)0.3753 (4)0.43143 (18)0.0375 (6)
C40.23515 (17)0.4104 (3)0.36307 (17)0.0380 (7)
H40.2421620.4356360.3059490.046*
C50.15851 (17)0.4066 (3)0.38276 (17)0.0373 (6)
C60.14629 (17)0.3724 (3)0.46663 (17)0.0393 (7)
H60.0939960.3717350.4788050.047*
N10.2053 (2)0.3015 (4)0.62306 (17)0.0552 (7)
N20.38409 (17)0.3748 (3)0.4122 (2)0.0530 (7)
N30.08572 (17)0.4407 (4)0.31102 (18)0.0552 (7)
O10.14078 (18)0.3516 (4)0.64216 (16)0.0780 (8)
O20.26172 (18)0.2195 (3)0.67273 (14)0.0753 (8)
O30.44113 (14)0.3279 (3)0.47247 (19)0.0778 (8)
O40.39003 (15)0.4197 (4)0.33769 (17)0.0748 (7)
O50.09752 (15)0.5061 (3)0.24181 (15)0.0707 (7)
O60.01788 (16)0.4066 (4)0.32863 (18)0.0871 (8)
C110.37425 (18)0.8616 (4)0.44847 (17)0.0416 (7)
H110.4311990.8555880.464460.05*
C120.33560 (17)0.8871 (4)0.35789 (17)0.0386 (6)
C130.25164 (17)0.9004 (4)0.33542 (18)0.0399 (7)
H130.2258730.9186820.2764120.048*
C140.20357 (16)0.8866 (3)0.40060 (17)0.0355 (6)
C150.11648 (17)0.8960 (4)0.37776 (19)0.0447 (7)
H150.0900080.9177910.3192320.054*
C160.07171 (19)0.8732 (4)0.4412 (2)0.0491 (8)
H160.0147330.8782110.4255280.059*
C170.11022 (19)0.8425 (4)0.5296 (2)0.0490 (8)
H170.0786940.8272250.5721770.059*
C180.19420 (19)0.8348 (4)0.55427 (19)0.0437 (7)
H180.21920.8154730.613450.052*
C190.24309 (17)0.8560 (3)0.49009 (17)0.0363 (6)
C200.32950 (17)0.8457 (4)0.51201 (18)0.0402 (7)
H200.3561460.8278980.570770.048*
C210.3838 (2)0.8968 (4)0.2863 (2)0.0473 (7)
C220.4755 (2)0.9057 (5)0.3127 (2)0.0672 (10)
H22A0.4980450.9171320.2606320.101*
H22B0.4957320.7883750.3441690.101*
H22C0.4914391.0174720.3501960.101*
O70.34871 (15)0.8966 (3)0.20881 (14)0.0650 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0476 (19)0.0333 (14)0.0369 (15)0.0045 (12)0.0118 (14)0.0014 (11)
C20.0381 (18)0.0357 (14)0.0434 (16)0.0008 (12)0.0011 (14)0.0009 (12)
C30.0303 (16)0.0325 (13)0.0510 (17)0.0010 (11)0.0114 (14)0.0037 (12)
C40.0447 (19)0.0346 (14)0.0363 (14)0.0034 (12)0.0121 (14)0.0028 (11)
C50.0352 (17)0.0306 (13)0.0421 (15)0.0039 (11)0.0007 (13)0.0036 (11)
C60.0346 (17)0.0345 (14)0.0502 (17)0.0023 (12)0.0121 (14)0.0070 (12)
N10.073 (2)0.0471 (15)0.0475 (16)0.0166 (14)0.0164 (16)0.0030 (12)
N20.0416 (17)0.0424 (14)0.078 (2)0.0023 (12)0.0204 (16)0.0066 (13)
N30.0462 (19)0.0524 (15)0.0570 (17)0.0066 (13)0.0114 (14)0.0043 (13)
O10.095 (2)0.0840 (17)0.0698 (16)0.0071 (15)0.0500 (16)0.0035 (13)
O20.097 (2)0.0782 (16)0.0457 (13)0.0164 (15)0.0035 (14)0.0144 (12)
O30.0317 (14)0.0797 (16)0.118 (2)0.0058 (12)0.0062 (15)0.0163 (15)
O40.0642 (18)0.0922 (18)0.0813 (17)0.0031 (13)0.0449 (15)0.0105 (14)
O50.0794 (19)0.0802 (16)0.0436 (12)0.0271 (13)0.0073 (13)0.0002 (12)
O60.0373 (16)0.101 (2)0.112 (2)0.0084 (14)0.0087 (15)0.0112 (16)
C110.0329 (16)0.0417 (15)0.0488 (17)0.0003 (12)0.0056 (14)0.0014 (12)
C120.0349 (17)0.0365 (14)0.0451 (16)0.0017 (12)0.0102 (13)0.0027 (12)
C130.0406 (18)0.0362 (14)0.0407 (15)0.0010 (12)0.0038 (13)0.0014 (12)
C140.0290 (16)0.0292 (12)0.0461 (16)0.0018 (11)0.0032 (13)0.0040 (11)
C150.0361 (18)0.0404 (15)0.0538 (17)0.0053 (12)0.0010 (15)0.0034 (13)
C160.0349 (18)0.0454 (16)0.068 (2)0.0061 (13)0.0131 (16)0.0054 (15)
C170.044 (2)0.0430 (16)0.066 (2)0.0039 (13)0.0249 (17)0.0054 (14)
C180.049 (2)0.0382 (15)0.0456 (16)0.0023 (13)0.0137 (15)0.0019 (12)
C190.0359 (17)0.0307 (14)0.0413 (15)0.0020 (11)0.0063 (13)0.0026 (11)
C200.0381 (18)0.0401 (14)0.0396 (15)0.0016 (12)0.0016 (13)0.0004 (12)
C210.052 (2)0.0463 (16)0.0466 (18)0.0000 (14)0.0180 (16)0.0048 (14)
C220.046 (2)0.095 (3)0.067 (2)0.0053 (19)0.0274 (18)0.0026 (19)
O70.0648 (16)0.0863 (16)0.0466 (13)0.0020 (13)0.0180 (12)0.0060 (11)
Geometric parameters (Å, º) top
C1—C21.375 (4)C12—C131.372 (4)
C1—C61.375 (4)C12—C211.500 (4)
C1—N11.475 (4)C13—C141.416 (4)
C2—C31.368 (4)C13—H130.93
C2—H20.93C14—C191.415 (4)
C3—C41.371 (4)C14—C151.421 (4)
C3—N21.481 (4)C15—C161.361 (4)
C4—C51.375 (4)C15—H150.93
C4—H40.93C16—C171.396 (4)
C5—C61.373 (4)C16—H160.93
C5—N31.478 (4)C17—C181.372 (4)
C6—H60.93C17—H170.93
N1—O21.217 (4)C18—C191.418 (4)
N1—O11.222 (3)C18—H180.93
N2—O41.214 (3)C19—C201.410 (4)
N2—O31.224 (3)C20—H200.93
N3—O51.212 (3)C21—O71.215 (3)
N3—O61.240 (3)C21—C221.497 (4)
C11—C201.357 (4)C22—H22A0.96
C11—C121.422 (4)C22—H22B0.96
C11—H110.93C22—H22C0.96
C2—C1—C6123.4 (2)C12—C13—C14121.1 (3)
C2—C1—N1117.7 (3)C12—C13—H13119.5
C6—C1—N1118.9 (3)C14—C13—H13119.5
C3—C2—C1116.5 (3)C19—C14—C13119.2 (2)
C3—C2—H2121.8C19—C14—C15119.3 (2)
C1—C2—H2121.8C13—C14—C15121.5 (2)
C2—C3—C4123.5 (2)C16—C15—C14120.2 (3)
C2—C3—N2118.1 (3)C16—C15—H15119.9
C4—C3—N2118.4 (2)C14—C15—H15119.9
C3—C4—C5117.0 (2)C15—C16—C17120.8 (3)
C3—C4—H4121.5C15—C16—H16119.6
C5—C4—H4121.5C17—C16—H16119.6
C6—C5—C4122.8 (3)C18—C17—C16120.5 (3)
C6—C5—N3118.1 (3)C18—C17—H17119.7
C4—C5—N3119.0 (2)C16—C17—H17119.7
C5—C6—C1116.8 (3)C17—C18—C19120.4 (3)
C5—C6—H6121.6C17—C18—H18119.8
C1—C6—H6121.6C19—C18—H18119.8
O2—N1—O1125.4 (3)C20—C19—C14118.9 (2)
O2—N1—C1117.0 (3)C20—C19—C18122.4 (2)
O1—N1—C1117.6 (3)C14—C19—C18118.7 (3)
O4—N2—O3125.5 (3)C11—C20—C19120.8 (3)
O4—N2—C3117.2 (3)C11—C20—H20119.6
O3—N2—C3117.3 (3)C19—C20—H20119.6
O5—N3—O6126.0 (3)O7—C21—C22121.3 (3)
O5—N3—C5117.3 (3)O7—C21—C12120.2 (3)
O6—N3—C5116.6 (3)C22—C21—C12118.4 (3)
C20—C11—C12121.1 (3)C21—C22—H22A109.5
C20—C11—H11119.4C21—C22—H22B109.5
C12—C11—H11119.4H22A—C22—H22B109.5
C13—C12—C11118.9 (2)C21—C22—H22C109.5
C13—C12—C21119.2 (3)H22A—C22—H22C109.5
C11—C12—C21121.9 (3)H22B—C22—H22C109.5
C6—C1—C2—C30.9 (4)C20—C11—C12—C131.5 (4)
N1—C1—C2—C3179.4 (2)C20—C11—C12—C21177.5 (2)
C1—C2—C3—C40.6 (4)C11—C12—C13—C140.8 (4)
C1—C2—C3—N2179.8 (2)C21—C12—C13—C14178.3 (2)
C2—C3—C4—C50.3 (4)C12—C13—C14—C190.9 (3)
N2—C3—C4—C5178.9 (2)C12—C13—C14—C15178.7 (2)
C3—C4—C5—C60.9 (4)C19—C14—C15—C160.9 (4)
C3—C4—C5—N3179.1 (2)C13—C14—C15—C16176.9 (2)
C4—C5—C6—C10.7 (4)C14—C15—C16—C170.7 (4)
N3—C5—C6—C1179.4 (2)C15—C16—C17—C180.0 (4)
C2—C1—C6—C50.2 (4)C16—C17—C18—C190.6 (4)
N1—C1—C6—C5179.9 (2)C13—C14—C19—C201.8 (3)
C2—C1—N1—O220.0 (4)C15—C14—C19—C20179.6 (2)
C6—C1—N1—O2159.7 (3)C13—C14—C19—C18177.6 (2)
C2—C1—N1—O1161.3 (3)C15—C14—C19—C180.3 (3)
C6—C1—N1—O119.0 (4)C17—C18—C19—C20178.9 (2)
C2—C3—N2—O4175.6 (2)C17—C18—C19—C140.4 (4)
C4—C3—N2—O45.2 (4)C12—C11—C20—C190.6 (4)
C2—C3—N2—O34.9 (4)C14—C19—C20—C111.1 (3)
C4—C3—N2—O3174.4 (2)C18—C19—C20—C11178.2 (2)
C6—C5—N3—O5166.6 (2)C13—C12—C21—O77.3 (4)
C4—C5—N3—O513.4 (3)C11—C12—C21—O7171.7 (3)
C6—C5—N3—O610.7 (4)C13—C12—C21—C22173.0 (3)
C4—C5—N3—O6169.3 (3)C11—C12—C21—C228.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O2i0.932.43.189 (3)143
C11—H11···O3ii0.932.483.323 (4)150
C22—H22A···O4iii0.962.643.554 (4)159
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x+1, y+1, z+1; (iii) x+1, y+1/2, z+1/2.
1,3,5-Trinitrobenzene–9-bromoanthracene (1/1) (II) top
Crystal data top
C14H9Br·C6H3N3O6F(000) = 944
Mr = 470.24Dx = 1.695 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8164 reflections
a = 7.0928 (2) Åθ = 2.2–27.9°
b = 9.7701 (3) ŵ = 2.28 mm1
c = 27.0563 (7) ÅT = 173 K
β = 100.674 (1)°Needle, yellow
V = 1842.49 (9) Å30.33 × 0.12 × 0.11 mm
Z = 4
Data collection top
Bruker D8 Venture Photon CCD area detector
diffractometer
3758 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
ω scansθmax = 28.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.56, Tmax = 0.77k = 1212
28424 measured reflectionsl = 3535
4450 independent reflections
Refinement top
Refinement on F20 constraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.096 w = 1/[σ2(Fo2) + (0.0343P)2 + 2.1935P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
4450 reflectionsΔρmax = 1.42 e Å3
271 parametersΔρmin = 0.94 e Å3
0 restraints
Special details top

Experimental. (SADABS; Sheldrick, 1996)

Geometry. All standard uncertainties (s.u.) (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u. are taken into account individually in the estimation of s.u. in distances, angles and torsion angles; correlations between s.u. in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u. is used for estimating s.u. involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3620 (3)0.7554 (2)0.10545 (9)0.0275 (5)
C20.3965 (3)0.6350 (2)0.08161 (9)0.0256 (5)
H20.3691130.626740.0460110.031*
C30.4723 (3)0.5280 (2)0.11194 (9)0.0236 (4)
C40.5164 (3)0.5366 (2)0.16372 (9)0.0267 (5)
H40.5680610.4608840.1837710.032*
C50.4822 (4)0.6599 (3)0.18498 (9)0.0293 (5)
C60.4047 (4)0.7724 (2)0.15702 (10)0.0303 (5)
H60.3822480.8565850.1725170.036*
N10.2782 (3)0.8716 (2)0.07398 (10)0.0370 (5)
N20.5097 (3)0.3967 (2)0.08822 (8)0.0290 (4)
N30.5319 (4)0.6732 (2)0.24030 (8)0.0401 (6)
O10.2533 (3)0.9777 (2)0.09572 (9)0.0543 (6)
O20.2376 (3)0.8538 (2)0.02904 (9)0.0519 (6)
O30.4729 (3)0.3904 (2)0.04231 (7)0.0396 (4)
O40.5756 (3)0.30406 (19)0.11577 (8)0.0434 (5)
O50.5774 (5)0.5714 (2)0.26496 (8)0.0654 (7)
O60.5271 (4)0.7868 (3)0.25776 (9)0.0634 (7)
C110.9660 (3)0.6511 (2)0.16436 (8)0.0235 (4)
C120.8864 (3)0.7691 (2)0.13900 (8)0.0231 (4)
C130.8514 (4)0.8940 (2)0.16310 (9)0.0305 (5)
H130.8839230.9009380.1986810.037*
C140.7719 (4)1.0031 (2)0.13575 (10)0.0338 (6)
H140.7486851.0849590.152610.041*
C150.7233 (4)0.9972 (3)0.08274 (10)0.0319 (5)
H150.6689811.0748760.0642720.038*
C160.7543 (3)0.8804 (2)0.05821 (9)0.0285 (5)
H160.7219390.8774210.022550.034*
C170.8346 (3)0.7622 (2)0.08509 (8)0.0223 (4)
C180.8607 (3)0.6406 (2)0.06047 (8)0.0239 (5)
H180.8243850.6367030.0248880.029*
C190.9385 (3)0.5241 (2)0.08641 (8)0.0226 (4)
C200.9636 (3)0.4002 (2)0.06075 (9)0.0274 (5)
H200.9243360.3960030.025250.033*
C211.0428 (4)0.2876 (3)0.08608 (10)0.0322 (5)
H211.0581740.2056580.0683140.039*
C221.1019 (4)0.2928 (3)0.13873 (10)0.0319 (5)
H221.1590530.2142830.1560670.038*
C231.0789 (3)0.4077 (2)0.16519 (9)0.0282 (5)
H231.1186680.4080270.2007020.034*
C240.9956 (3)0.5283 (2)0.14027 (8)0.0224 (4)
Br11.03399 (4)0.65915 (3)0.23592 (2)0.03853 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0215 (11)0.0233 (11)0.0390 (13)0.0012 (9)0.0088 (10)0.0050 (10)
C20.0224 (11)0.0255 (12)0.0296 (11)0.0013 (9)0.0067 (9)0.0014 (9)
C30.0203 (10)0.0211 (11)0.0306 (11)0.0022 (8)0.0075 (9)0.0027 (9)
C40.0268 (12)0.0232 (11)0.0307 (12)0.0006 (9)0.0068 (9)0.0009 (9)
C50.0297 (12)0.0287 (12)0.0301 (12)0.0045 (10)0.0071 (10)0.0041 (10)
C60.0309 (13)0.0228 (12)0.0393 (13)0.0013 (10)0.0121 (10)0.0064 (10)
N10.0296 (11)0.0304 (12)0.0515 (14)0.0040 (9)0.0094 (10)0.0117 (10)
N20.0264 (10)0.0259 (10)0.0353 (11)0.0005 (8)0.0076 (8)0.0060 (9)
N30.0492 (14)0.0377 (13)0.0331 (12)0.0039 (11)0.0068 (10)0.0095 (10)
O10.0568 (14)0.0288 (11)0.0759 (16)0.0161 (10)0.0087 (12)0.0048 (10)
O20.0588 (14)0.0489 (13)0.0476 (13)0.0129 (11)0.0091 (10)0.0208 (10)
O30.0412 (11)0.0416 (11)0.0347 (10)0.0031 (9)0.0040 (8)0.0129 (8)
O40.0580 (13)0.0250 (9)0.0485 (12)0.0132 (9)0.0136 (10)0.0009 (8)
O50.116 (2)0.0441 (13)0.0327 (11)0.0039 (13)0.0041 (12)0.0036 (10)
O60.0894 (19)0.0487 (13)0.0455 (13)0.0123 (13)0.0048 (12)0.0221 (11)
C110.0252 (11)0.0260 (11)0.0195 (10)0.0006 (9)0.0044 (8)0.0025 (8)
C120.0239 (11)0.0214 (11)0.0242 (11)0.0001 (9)0.0047 (9)0.0014 (8)
C130.0406 (14)0.0230 (11)0.0279 (12)0.0002 (10)0.0061 (10)0.0032 (9)
C140.0423 (15)0.0183 (11)0.0409 (14)0.0006 (10)0.0077 (11)0.0026 (10)
C150.0334 (13)0.0232 (12)0.0388 (13)0.0023 (10)0.0062 (10)0.0078 (10)
C160.0297 (12)0.0277 (12)0.0275 (11)0.0021 (10)0.0042 (9)0.0061 (9)
C170.0199 (10)0.0233 (11)0.0245 (10)0.0006 (8)0.0060 (8)0.0031 (8)
C180.0225 (11)0.0290 (12)0.0207 (10)0.0019 (9)0.0053 (8)0.0003 (8)
C190.0188 (10)0.0242 (11)0.0260 (11)0.0005 (8)0.0071 (8)0.0003 (9)
C200.0249 (11)0.0286 (12)0.0300 (12)0.0002 (9)0.0086 (9)0.0047 (10)
C210.0301 (13)0.0227 (11)0.0465 (15)0.0021 (10)0.0146 (11)0.0055 (10)
C220.0309 (13)0.0219 (11)0.0443 (14)0.0046 (10)0.0103 (11)0.0073 (10)
C230.0274 (12)0.0252 (12)0.0319 (12)0.0020 (9)0.0056 (10)0.0057 (9)
C240.0197 (10)0.0216 (11)0.0267 (11)0.0000 (8)0.0061 (8)0.0019 (8)
Br10.05475 (19)0.03823 (16)0.02111 (13)0.01206 (12)0.00313 (10)0.00126 (10)
Geometric parameters (Å, º) top
C1—C61.382 (4)C12—C171.438 (3)
C1—C21.385 (3)C13—C141.359 (3)
C1—N11.477 (3)C13—H130.95
C2—C31.376 (3)C14—C151.413 (4)
C2—H20.95C14—H140.95
C3—C41.381 (3)C15—C161.358 (4)
C3—N21.480 (3)C15—H150.95
C4—C51.376 (3)C16—C171.426 (3)
C4—H40.95C16—H160.95
C5—C61.388 (3)C17—C181.391 (3)
C5—N31.479 (3)C18—C191.396 (3)
C6—H60.95C18—H180.95
N1—O21.209 (3)C19—C201.423 (3)
N1—O11.221 (3)C19—C241.439 (3)
N2—O41.210 (3)C20—C211.362 (4)
N2—O31.222 (3)C20—H200.95
N3—O51.208 (3)C21—C221.409 (4)
N3—O61.209 (3)C21—H210.95
C11—C241.400 (3)C22—C231.358 (4)
C11—C121.405 (3)C22—H220.95
C11—Br11.908 (2)C23—C241.430 (3)
C12—C131.426 (3)C23—H230.95
C6—C1—C2123.2 (2)C12—C13—H13119.6
C6—C1—N1118.6 (2)C13—C14—C15121.3 (2)
C2—C1—N1118.1 (2)C13—C14—H14119.4
C3—C2—C1116.8 (2)C15—C14—H14119.4
C3—C2—H2121.6C16—C15—C14119.9 (2)
C1—C2—H2121.6C16—C15—H15120
C2—C3—C4123.3 (2)C14—C15—H15120
C2—C3—N2118.8 (2)C15—C16—C17121.1 (2)
C4—C3—N2117.9 (2)C15—C16—H16119.4
C5—C4—C3117.0 (2)C17—C16—H16119.4
C5—C4—H4121.5C18—C17—C16121.6 (2)
C3—C4—H4121.5C18—C17—C12119.6 (2)
C4—C5—C6123.2 (2)C16—C17—C12118.8 (2)
C4—C5—N3118.2 (2)C17—C18—C19122.1 (2)
C6—C5—N3118.6 (2)C17—C18—H18119
C1—C6—C5116.4 (2)C19—C18—H18119
C1—C6—H6121.8C18—C19—C20121.5 (2)
C5—C6—H6121.8C18—C19—C24119.8 (2)
O2—N1—O1125.3 (2)C20—C19—C24118.8 (2)
O2—N1—C1117.7 (2)C21—C20—C19121.3 (2)
O1—N1—C1117.0 (2)C21—C20—H20119.4
O4—N2—O3125.0 (2)C19—C20—H20119.4
O4—N2—C3117.4 (2)C20—C21—C22119.8 (2)
O3—N2—C3117.6 (2)C20—C21—H21120.1
O5—N3—O6124.3 (2)C22—C21—H21120.1
O5—N3—C5118.4 (2)C23—C22—C21121.4 (2)
O6—N3—C5117.2 (2)C23—C22—H22119.3
C24—C11—C12123.9 (2)C21—C22—H22119.3
C24—C11—Br1118.43 (16)C22—C23—C24120.8 (2)
C12—C11—Br1117.69 (17)C22—C23—H23119.6
C11—C12—C13124.5 (2)C24—C23—H23119.6
C11—C12—C17117.4 (2)C11—C24—C23124.9 (2)
C13—C12—C17118.0 (2)C11—C24—C19117.23 (19)
C14—C13—C12120.8 (2)C23—C24—C19117.9 (2)
C14—C13—H13119.6
C6—C1—C2—C31.8 (4)C17—C12—C13—C140.2 (4)
N1—C1—C2—C3179.2 (2)C12—C13—C14—C150.6 (4)
C1—C2—C3—C40.9 (3)C13—C14—C15—C160.6 (4)
C1—C2—C3—N2179.4 (2)C14—C15—C16—C170.4 (4)
C2—C3—C4—C50.3 (4)C15—C16—C17—C18177.7 (2)
N2—C3—C4—C5179.4 (2)C15—C16—C17—C121.2 (4)
C3—C4—C5—C60.8 (4)C11—C12—C17—C181.3 (3)
C3—C4—C5—N3178.7 (2)C13—C12—C17—C18177.8 (2)
C2—C1—C6—C51.3 (4)C11—C12—C17—C16179.7 (2)
N1—C1—C6—C5179.6 (2)C13—C12—C17—C161.2 (3)
C4—C5—C6—C10.0 (4)C16—C17—C18—C19179.8 (2)
N3—C5—C6—C1179.5 (2)C12—C17—C18—C190.8 (3)
C6—C1—N1—O2178.3 (2)C17—C18—C19—C20179.7 (2)
C2—C1—N1—O22.6 (3)C17—C18—C19—C240.4 (3)
C6—C1—N1—O10.8 (3)C18—C19—C20—C21178.8 (2)
C2—C1—N1—O1178.3 (2)C24—C19—C20—C211.0 (3)
C2—C3—N2—O4179.7 (2)C19—C20—C21—C220.1 (4)
C4—C3—N2—O40.6 (3)C20—C21—C22—C231.1 (4)
C2—C3—N2—O30.8 (3)C21—C22—C23—C240.8 (4)
C4—C3—N2—O3179.0 (2)C12—C11—C24—C23179.0 (2)
C4—C5—N3—O59.2 (4)Br1—C11—C24—C231.9 (3)
C6—C5—N3—O5171.2 (3)C12—C11—C24—C190.7 (3)
C4—C5—N3—O6169.6 (3)Br1—C11—C24—C19178.46 (16)
C6—C5—N3—O69.9 (4)C22—C23—C24—C11179.9 (2)
C24—C11—C12—C13178.5 (2)C22—C23—C24—C190.5 (3)
Br1—C11—C12—C130.6 (3)C18—C19—C24—C111.2 (3)
C24—C11—C12—C170.6 (3)C20—C19—C24—C11179.0 (2)
Br1—C11—C12—C17179.70 (16)C18—C19—C24—C23178.5 (2)
C11—C12—C13—C14179.3 (2)C20—C19—C24—C231.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O6i0.952.53.287 (3)140
C6—H6···O5ii0.952.683.593 (3)162
C14—H14···O4iii0.952.573.255 (3)129
C21—H21···O1iv0.952.653.364 (3)132
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x+1, y+1/2, z+1/2; (iii) x, y+1, z; (iv) x+1, y1, z.
1,3,5-Trinitrobenzene–2-{(E)-[4-(dimethylamino)phenyl]diazenyl}benzoic acid (1/1) (III) top
Crystal data top
C15H15N3O2·C6H3N3O6Z = 2
Mr = 482.41F(000) = 500
Triclinic, P1Dx = 1.518 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.550 (3) ÅCell parameters from 9824 reflections
b = 10.437 (3) Åθ = 3.1–28.2°
c = 13.072 (5) ŵ = 0.12 mm1
α = 110.689 (10)°T = 173 K
β = 103.510 (12)°Cuboid, red
γ = 90.730 (12)°0.29 × 0.13 × 0.12 mm
V = 1055.2 (7) Å3
Data collection top
Bruker D8 Venture Photon CCD area detector
diffractometer
3262 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.072
ω scansθmax = 28.0°, θmin = 3.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.9, Tmax = 0.95k = 1313
39527 measured reflectionsl = 1717
5072 independent reflections
Refinement top
Refinement on F20 constraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.078H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.249 w = 1/[σ2(Fo2) + (0.1346P)2 + 0.8758P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
5072 reflectionsΔρmax = 0.49 e Å3
322 parametersΔρmin = 0.43 e Å3
0 restraints
Special details top

Experimental. (SADABS; Sheldrick, 1996)

Geometry. All standard uncertainties (s.u.) (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u. are taken into account individually in the estimation of s.u. in distances, angles and torsion angles; correlations between s.u. in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u. is used for estimating s.u. involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3627 (3)0.4196 (3)0.8376 (2)0.0274 (6)
C20.4468 (3)0.3469 (3)0.7610 (2)0.0265 (6)
H20.496730.2679510.766490.032*
C30.4549 (3)0.3944 (3)0.6758 (2)0.0266 (6)
C40.3817 (3)0.5079 (3)0.6651 (2)0.0279 (6)
H40.3864760.5376510.6050260.033*
C50.3010 (4)0.5763 (3)0.7456 (3)0.0287 (6)
C60.2887 (3)0.5341 (3)0.8327 (2)0.0284 (6)
H60.2317230.5820360.886680.034*
N10.3560 (3)0.3737 (3)0.9312 (2)0.0324 (6)
N20.5442 (3)0.3204 (3)0.5938 (2)0.0305 (6)
N30.2291 (3)0.7015 (3)0.7399 (2)0.0367 (6)
O10.2796 (3)0.4374 (3)0.9979 (2)0.0475 (6)
O20.4303 (3)0.2766 (3)0.93921 (19)0.0437 (6)
O30.6018 (3)0.2169 (2)0.6015 (2)0.0405 (6)
O40.5548 (3)0.3668 (3)0.5212 (2)0.0435 (6)
O50.2266 (3)0.7301 (3)0.6567 (2)0.0485 (7)
O60.1772 (3)0.7707 (3)0.8201 (2)0.0507 (7)
C110.1578 (3)0.1335 (3)0.5551 (2)0.0255 (6)
C120.1935 (4)0.0433 (3)0.6139 (2)0.0272 (6)
H12A0.2581460.0288520.5885790.033*
C130.1372 (3)0.0571 (3)0.7067 (2)0.0278 (6)
H130.1637170.0048670.7451810.033*
C140.0402 (3)0.1627 (3)0.7454 (2)0.0262 (6)
C150.0005 (3)0.2516 (3)0.6840 (3)0.0293 (6)
H150.0682930.321880.7074510.035*
C160.0572 (3)0.2365 (3)0.5914 (3)0.0283 (6)
H160.0287850.2965260.5512940.034*
C170.0277 (4)0.0891 (4)0.9028 (3)0.0388 (8)
H17A0.0127450.0061560.8529590.058*
H17B0.0222330.1160760.9666140.058*
H17C0.1453830.0962730.931180.058*
C180.1074 (5)0.2903 (4)0.8855 (3)0.0444 (9)
H18A0.1168740.3516730.8428310.067*
H18B0.0536110.3425230.9650880.067*
H18C0.2154790.2513830.879650.067*
C190.2781 (3)0.1679 (3)0.3235 (2)0.0265 (6)
C200.3656 (4)0.0550 (3)0.2908 (3)0.0336 (7)
H200.3801190.0056910.3311850.04*
C210.4310 (4)0.0317 (3)0.1995 (3)0.0378 (7)
H210.4902570.0453470.1772990.045*
C220.4111 (4)0.1198 (3)0.1398 (3)0.0347 (7)
H220.4553780.102060.0765070.042*
C230.3273 (4)0.2324 (3)0.1724 (2)0.0315 (7)
H230.3141850.2924070.1313610.038*
C240.2613 (3)0.2597 (3)0.2650 (2)0.0259 (6)
C250.1757 (4)0.3865 (3)0.2948 (3)0.0338 (7)
N110.2263 (3)0.1105 (2)0.4652 (2)0.0280 (6)
N120.2057 (3)0.1977 (3)0.4154 (2)0.0282 (6)
N130.0133 (3)0.1802 (3)0.8396 (2)0.0343 (6)
O110.1681 (4)0.4628 (3)0.2426 (2)0.0520 (7)
O120.1077 (3)0.4150 (2)0.3810 (2)0.0395 (6)
H120.130 (6)0.347 (6)0.413 (5)0.096 (18)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0319 (15)0.0312 (16)0.0233 (14)0.0012 (12)0.0082 (12)0.0144 (12)
C20.0295 (15)0.0266 (15)0.0271 (14)0.0022 (11)0.0080 (12)0.0138 (11)
C30.0283 (15)0.0286 (15)0.0275 (14)0.0014 (11)0.0117 (12)0.0130 (12)
C40.0310 (15)0.0302 (16)0.0273 (14)0.0010 (12)0.0080 (12)0.0162 (12)
C50.0340 (16)0.0247 (15)0.0322 (15)0.0045 (12)0.0108 (12)0.0147 (12)
C60.0308 (15)0.0286 (16)0.0284 (15)0.0018 (12)0.0111 (12)0.0115 (12)
N10.0394 (15)0.0364 (15)0.0263 (13)0.0010 (11)0.0120 (11)0.0150 (11)
N20.0340 (14)0.0340 (14)0.0290 (13)0.0028 (11)0.0128 (11)0.0151 (11)
N30.0400 (15)0.0311 (15)0.0463 (16)0.0088 (11)0.0155 (13)0.0197 (12)
O10.0657 (17)0.0558 (16)0.0391 (13)0.0174 (12)0.0322 (12)0.0264 (11)
O20.0643 (16)0.0442 (14)0.0379 (13)0.0172 (12)0.0205 (12)0.0283 (11)
O30.0502 (14)0.0396 (13)0.0461 (14)0.0167 (11)0.0266 (11)0.0232 (11)
O40.0583 (16)0.0514 (15)0.0398 (13)0.0125 (11)0.0292 (12)0.0285 (11)
O50.0607 (16)0.0482 (15)0.0630 (17)0.0212 (12)0.0295 (13)0.0424 (13)
O60.0681 (18)0.0384 (14)0.0545 (16)0.0222 (12)0.0277 (13)0.0194 (12)
C110.0235 (14)0.0251 (14)0.0304 (15)0.0009 (11)0.0062 (11)0.0138 (11)
C120.0304 (15)0.0251 (15)0.0286 (15)0.0056 (11)0.0074 (12)0.0129 (11)
C130.0329 (16)0.0257 (15)0.0289 (15)0.0065 (12)0.0069 (12)0.0154 (12)
C140.0245 (14)0.0278 (15)0.0284 (14)0.0001 (11)0.0056 (11)0.0134 (12)
C150.0269 (15)0.0301 (16)0.0361 (16)0.0075 (12)0.0095 (12)0.0173 (13)
C160.0280 (15)0.0289 (15)0.0332 (15)0.0029 (11)0.0062 (12)0.0185 (12)
C170.049 (2)0.0442 (19)0.0345 (17)0.0110 (15)0.0156 (15)0.0247 (15)
C180.054 (2)0.047 (2)0.048 (2)0.0202 (16)0.0299 (17)0.0257 (16)
C190.0272 (15)0.0297 (15)0.0255 (14)0.0022 (11)0.0074 (11)0.0130 (11)
C200.0400 (18)0.0306 (16)0.0373 (17)0.0089 (13)0.0128 (14)0.0188 (13)
C210.0437 (19)0.0353 (18)0.0395 (18)0.0131 (14)0.0151 (15)0.0163 (14)
C220.0404 (18)0.0392 (18)0.0294 (15)0.0066 (14)0.0161 (13)0.0135 (13)
C230.0387 (17)0.0324 (17)0.0285 (15)0.0046 (13)0.0106 (13)0.0159 (12)
C240.0310 (15)0.0255 (15)0.0236 (14)0.0031 (11)0.0086 (11)0.0110 (11)
C250.0413 (18)0.0328 (17)0.0356 (16)0.0088 (13)0.0156 (14)0.0186 (13)
N110.0310 (13)0.0289 (13)0.0284 (12)0.0023 (10)0.0077 (10)0.0155 (10)
N120.0303 (13)0.0280 (13)0.0320 (13)0.0039 (10)0.0104 (10)0.0162 (10)
N130.0427 (15)0.0367 (15)0.0351 (14)0.0125 (12)0.0185 (12)0.0214 (12)
O110.0814 (19)0.0462 (15)0.0579 (16)0.0309 (13)0.0425 (14)0.0375 (13)
O120.0535 (15)0.0356 (13)0.0446 (14)0.0169 (10)0.0292 (11)0.0218 (11)
Geometric parameters (Å, º) top
C1—C61.374 (4)C15—C161.371 (4)
C1—C21.382 (4)C15—H150.95
C1—N11.476 (4)C16—H160.95
C2—C31.384 (4)C17—N131.461 (4)
C2—H20.95C17—H17A0.98
C3—C41.382 (4)C17—H17B0.98
C3—N21.463 (4)C17—H17C0.98
C4—C51.383 (4)C18—N131.446 (4)
C4—H40.95C18—H18A0.98
C5—C61.383 (4)C18—H18B0.98
C5—N31.469 (4)C18—H18C0.98
C6—H60.95C19—C201.396 (4)
N1—O11.223 (4)C19—C241.412 (4)
N1—O21.225 (4)C19—N121.418 (4)
N2—O31.219 (3)C20—C211.380 (5)
N2—O41.227 (3)C20—H200.95
N3—O51.221 (4)C21—C221.390 (5)
N3—O61.228 (4)C21—H210.95
C11—N111.381 (4)C22—C231.374 (4)
C11—C161.406 (4)C22—H220.95
C11—C121.406 (4)C23—C241.395 (4)
C12—C131.370 (4)C23—H230.95
C12—H12A0.95C24—C251.494 (4)
C13—C141.408 (4)C25—O111.212 (4)
C13—H130.95C25—O121.331 (4)
C14—N131.366 (4)N11—N121.285 (3)
C14—C151.425 (4)O12—H120.95 (6)
C6—C1—C2123.5 (3)C15—C16—C11120.9 (3)
C6—C1—N1118.4 (3)C15—C16—H16119.6
C2—C1—N1118.1 (3)C11—C16—H16119.6
C1—C2—C3116.9 (3)N13—C17—H17A109.5
C1—C2—H2121.5N13—C17—H17B109.5
C3—C2—H2121.5H17A—C17—H17B109.5
C4—C3—C2122.6 (3)N13—C17—H17C109.5
C4—C3—N2119.1 (2)H17A—C17—H17C109.5
C2—C3—N2118.3 (3)H17B—C17—H17C109.5
C3—C4—C5117.2 (3)N13—C18—H18A109.5
C3—C4—H4121.4N13—C18—H18B109.5
C5—C4—H4121.4H18A—C18—H18B109.5
C6—C5—C4122.9 (3)N13—C18—H18C109.5
C6—C5—N3118.6 (3)H18A—C18—H18C109.5
C4—C5—N3118.5 (3)H18B—C18—H18C109.5
C1—C6—C5116.9 (3)C20—C19—C24119.7 (3)
C1—C6—H6121.6C20—C19—N12123.1 (3)
C5—C6—H6121.6C24—C19—N12117.3 (2)
O1—N1—O2124.0 (3)C21—C20—C19119.8 (3)
O1—N1—C1117.8 (3)C21—C20—H20120.1
O2—N1—C1118.2 (3)C19—C20—H20120.1
O3—N2—O4124.5 (3)C20—C21—C22120.8 (3)
O3—N2—C3118.1 (2)C20—C21—H21119.6
O4—N2—C3117.3 (3)C22—C21—H21119.6
O5—N3—O6124.7 (3)C23—C22—C21120.0 (3)
O5—N3—C5117.9 (3)C23—C22—H22120
O6—N3—C5117.3 (3)C21—C22—H22120
N11—C11—C16126.2 (3)C22—C23—C24120.7 (3)
N11—C11—C12115.5 (3)C22—C23—H23119.7
C16—C11—C12118.3 (3)C24—C23—H23119.7
C13—C12—C11121.6 (3)C23—C24—C19119.1 (3)
C13—C12—H12A119.2C23—C24—C25116.4 (3)
C11—C12—H12A119.2C19—C24—C25124.5 (3)
C12—C13—C14120.3 (3)O11—C25—O12120.1 (3)
C12—C13—H13119.9O11—C25—C24121.4 (3)
C14—C13—H13119.9O12—C25—C24118.4 (3)
N13—C14—C13121.1 (3)N12—N11—C11116.7 (2)
N13—C14—C15120.6 (3)N11—N12—C19114.0 (2)
C13—C14—C15118.3 (3)C14—N13—C18123.2 (3)
C16—C15—C14120.6 (3)C14—N13—C17120.9 (3)
C16—C15—H15119.7C18—N13—C17115.9 (3)
C14—C15—H15119.7C25—O12—H12108 (3)
C6—C1—C2—C30.0 (4)N13—C14—C15—C16178.1 (3)
N1—C1—C2—C3178.3 (3)C13—C14—C15—C161.7 (4)
C1—C2—C3—C40.8 (4)C14—C15—C16—C110.1 (4)
C1—C2—C3—N2179.5 (2)N11—C11—C16—C15178.3 (3)
C2—C3—C4—C51.5 (4)C12—C11—C16—C152.1 (4)
N2—C3—C4—C5178.9 (3)C24—C19—C20—C211.8 (5)
C3—C4—C5—C61.4 (4)N12—C19—C20—C21179.2 (3)
C3—C4—C5—N3176.9 (3)C19—C20—C21—C220.1 (5)
C2—C1—C6—C50.0 (4)C20—C21—C22—C230.8 (5)
N1—C1—C6—C5178.4 (3)C21—C22—C23—C240.1 (5)
C4—C5—C6—C10.7 (4)C22—C23—C24—C191.6 (4)
N3—C5—C6—C1177.6 (3)C22—C23—C24—C25178.7 (3)
C6—C1—N1—O12.5 (4)C20—C19—C24—C232.5 (4)
C2—C1—N1—O1179.1 (3)N12—C19—C24—C23178.5 (3)
C6—C1—N1—O2175.7 (3)C20—C19—C24—C25177.7 (3)
C2—C1—N1—O22.7 (4)N12—C19—C24—C251.3 (4)
C4—C3—N2—O3176.7 (3)C23—C24—C25—O111.7 (5)
C2—C3—N2—O32.9 (4)C19—C24—C25—O11178.5 (3)
C4—C3—N2—O42.8 (4)C23—C24—C25—O12178.5 (3)
C2—C3—N2—O4177.6 (3)C19—C24—C25—O121.2 (5)
C6—C5—N3—O5172.8 (3)C16—C11—N11—N125.5 (4)
C4—C5—N3—O58.8 (4)C12—C11—N11—N12174.9 (2)
C6—C5—N3—O67.8 (4)C11—N11—N12—C19179.7 (2)
C4—C5—N3—O6170.5 (3)C20—C19—N12—N110.7 (4)
N11—C11—C12—C13178.1 (3)C24—C19—N12—N11179.7 (2)
C16—C11—C12—C132.3 (4)C13—C14—N13—C18177.4 (3)
C11—C12—C13—C140.4 (4)C15—C14—N13—C182.4 (5)
C12—C13—C14—N13178.2 (3)C13—C14—N13—C170.4 (4)
C12—C13—C14—C151.6 (4)C15—C14—N13—C17179.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O4i0.952.353.285 (4)169
C15—H15···O11ii0.952.343.254 (4)161
C18—H18A···O11ii0.982.553.519 (4)170
C20—H20···O3iii0.952.643.574 (4)167
O12—H12···N120.95 (6)1.70 (6)2.577 (3)153 (5)
C21—H21···O2iii0.952.563.469 (4)161
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z+1; (iii) x+1, y, z+1.
1,3,5-Trinitrobenzene–1-naphthoic acid–2-amino-5-nitropyridine (1/1/1) (IV) top
Crystal data top
C6H3N3O6·C11H8O2·C5H5N3O2Z = 2
Mr = 524.41F(000) = 540
Triclinic, P1Dx = 1.571 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.5365 (15) ÅCell parameters from 8623 reflections
b = 7.9003 (16) Åθ = 3.1–28.3°
c = 19.153 (4) ŵ = 0.13 mm1
α = 97.580 (7)°T = 173 K
β = 94.667 (6)°Plate, brown
γ = 99.547 (7)°0.63 × 0.33 × 0.06 mm
V = 1108.5 (4) Å3
Data collection top
Bruker D8 Venture Photon CCD area detector
diffractometer
3368 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ω scansθmax = 25.5°, θmin = 3.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.9, Tmax = 0.95k = 98
12982 measured reflectionsl = 2323
3988 independent reflections
Refinement top
Refinement on F20 constraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.072H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.168 w = 1/[σ2(Fo2) + 2.9593P]
where P = (Fo2 + 2Fc2)/3
S = 1.22(Δ/σ)max < 0.001
3988 reflectionsΔρmax = 0.32 e Å3
355 parametersΔρmin = 0.36 e Å3
0 restraints
Special details top

Experimental. (SADABS; Sheldrick, 1996)

Geometry. All standard uncertainties (s.u.) (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u. are taken into account individually in the estimation of s.u. in distances, angles and torsion angles; correlations between s.u. in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u. is used for estimating s.u. involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3489 (5)0.8531 (5)0.28180 (19)0.0286 (8)
C20.5027 (5)0.7901 (5)0.2644 (2)0.0305 (8)
H20.5923980.7748780.2996620.037*
C30.5190 (5)0.7506 (5)0.1933 (2)0.0321 (9)
C40.3924 (5)0.7760 (5)0.1413 (2)0.0337 (9)
H40.4062940.7475250.0925260.04*
C50.2448 (5)0.8441 (5)0.1624 (2)0.0309 (8)
C60.2177 (5)0.8818 (5)0.23294 (19)0.0287 (8)
H60.1137330.9254190.2468430.034*
N10.3220 (5)0.8876 (4)0.35735 (17)0.0340 (8)
N20.6777 (5)0.6813 (5)0.1725 (2)0.0445 (9)
N30.1080 (5)0.8742 (5)0.10842 (18)0.0416 (9)
O10.1697 (4)0.8928 (4)0.37245 (15)0.0441 (7)
O20.4547 (4)0.9063 (5)0.40103 (15)0.0521 (9)
O30.7923 (4)0.6648 (5)0.2201 (2)0.0562 (9)
O40.6891 (5)0.6423 (5)0.10927 (19)0.0617 (10)
O50.1245 (5)0.8221 (6)0.04677 (17)0.0680 (11)
O60.0122 (4)0.9495 (5)0.12813 (17)0.0520 (8)
C110.2801 (5)0.3592 (5)0.23195 (19)0.0283 (8)
C120.1324 (5)0.4164 (5)0.2022 (2)0.0339 (9)
H120.05570.4665510.2326610.041*
C130.0906 (6)0.4036 (6)0.1289 (2)0.0413 (10)
H130.0133420.4424950.1099790.05*
C140.2039 (6)0.3333 (6)0.0846 (2)0.0423 (11)
H140.1764840.3225850.0347870.051*
C150.3602 (5)0.2768 (5)0.11240 (19)0.0333 (9)
C160.4790 (6)0.2077 (6)0.0674 (2)0.0427 (11)
H160.4514170.1963790.0175720.051*
C170.6309 (6)0.1573 (6)0.0937 (2)0.0465 (11)
H170.7096030.1129820.062540.056*
C180.6715 (5)0.1709 (5)0.1671 (2)0.0370 (10)
H180.7786090.1360360.1853560.044*
C190.5604 (5)0.2332 (5)0.2127 (2)0.0309 (8)
H190.5903960.2400160.2622660.037*
C200.3986 (5)0.2887 (5)0.18715 (19)0.0296 (8)
C210.3071 (5)0.3680 (5)0.31063 (19)0.0293 (8)
O70.2603 (4)0.5052 (4)0.34527 (15)0.0370 (7)
O80.3642 (4)0.2557 (4)0.33988 (14)0.0385 (7)
H5A0.309 (7)0.226 (7)0.440 (3)0.058 (15)*
H5B0.256 (5)0.144 (6)0.506 (2)0.030 (11)*
H70.270 (7)0.503 (7)0.395 (3)0.063 (15)*
C220.2465 (5)0.3802 (5)0.51944 (18)0.0265 (8)
C230.1956 (5)0.3906 (5)0.58930 (19)0.0296 (8)
H230.1831910.2910920.6126650.036*
C240.1651 (5)0.5429 (5)0.62225 (19)0.0309 (9)
H240.1326390.5532610.6693350.037*
C250.1822 (5)0.6859 (5)0.58541 (19)0.0272 (8)
C260.2293 (5)0.6680 (5)0.51770 (19)0.0295 (8)
H260.2400270.7661880.4935430.035*
N40.2607 (4)0.5197 (4)0.48431 (15)0.0290 (7)
N50.2777 (5)0.2340 (4)0.48463 (19)0.0353 (8)
N60.1470 (4)0.8518 (4)0.61748 (17)0.0325 (7)
O90.1578 (4)0.9701 (4)0.58321 (17)0.0439 (7)
O100.1098 (5)0.8655 (4)0.67946 (15)0.0508 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0303 (19)0.025 (2)0.0300 (19)0.0012 (15)0.0051 (15)0.0064 (15)
C20.0284 (19)0.026 (2)0.038 (2)0.0046 (16)0.0043 (16)0.0101 (16)
C30.0267 (19)0.025 (2)0.045 (2)0.0021 (16)0.0119 (17)0.0048 (17)
C40.034 (2)0.031 (2)0.034 (2)0.0036 (17)0.0090 (16)0.0040 (17)
C50.0273 (19)0.030 (2)0.033 (2)0.0025 (16)0.0025 (15)0.0057 (16)
C60.0250 (18)0.0252 (19)0.036 (2)0.0028 (15)0.0065 (15)0.0047 (16)
N10.042 (2)0.0284 (18)0.0328 (18)0.0076 (15)0.0059 (15)0.0074 (14)
N20.035 (2)0.037 (2)0.064 (3)0.0037 (16)0.0163 (18)0.0109 (19)
N30.037 (2)0.050 (2)0.034 (2)0.0059 (17)0.0021 (15)0.0095 (17)
O10.0461 (18)0.052 (2)0.0390 (16)0.0127 (15)0.0175 (14)0.0090 (14)
O20.0512 (19)0.069 (2)0.0340 (16)0.0103 (17)0.0051 (14)0.0065 (15)
O30.0378 (18)0.056 (2)0.083 (3)0.0206 (15)0.0153 (17)0.0201 (19)
O40.052 (2)0.068 (3)0.064 (2)0.0079 (18)0.0286 (17)0.0023 (19)
O50.058 (2)0.107 (3)0.0313 (18)0.004 (2)0.0025 (15)0.0035 (18)
O60.0405 (18)0.066 (2)0.0508 (19)0.0108 (16)0.0000 (15)0.0138 (17)
C110.0286 (19)0.024 (2)0.0307 (19)0.0004 (15)0.0074 (15)0.0017 (15)
C120.030 (2)0.033 (2)0.039 (2)0.0021 (17)0.0073 (17)0.0092 (17)
C130.033 (2)0.047 (3)0.040 (2)0.0048 (19)0.0023 (18)0.0105 (19)
C140.044 (2)0.046 (3)0.030 (2)0.006 (2)0.0002 (18)0.0029 (19)
C150.035 (2)0.034 (2)0.0260 (19)0.0062 (17)0.0064 (16)0.0008 (16)
C160.055 (3)0.041 (3)0.030 (2)0.002 (2)0.0142 (19)0.0001 (18)
C170.049 (3)0.044 (3)0.044 (2)0.000 (2)0.018 (2)0.001 (2)
C180.032 (2)0.035 (2)0.041 (2)0.0008 (17)0.0113 (17)0.0005 (18)
C190.0294 (19)0.026 (2)0.035 (2)0.0004 (16)0.0047 (16)0.0007 (16)
C200.032 (2)0.025 (2)0.0282 (19)0.0052 (16)0.0064 (15)0.0018 (15)
C210.0298 (19)0.027 (2)0.031 (2)0.0026 (16)0.0085 (15)0.0050 (17)
O70.0569 (18)0.0299 (16)0.0279 (15)0.0144 (13)0.0103 (13)0.0055 (12)
O80.0495 (17)0.0396 (17)0.0307 (14)0.0163 (14)0.0107 (12)0.0064 (13)
C220.0257 (18)0.026 (2)0.0279 (18)0.0047 (15)0.0000 (14)0.0045 (15)
C230.0316 (19)0.032 (2)0.0265 (19)0.0071 (16)0.0016 (15)0.0087 (16)
C240.033 (2)0.034 (2)0.0249 (18)0.0044 (17)0.0033 (15)0.0053 (16)
C250.0253 (18)0.028 (2)0.0278 (18)0.0037 (15)0.0020 (14)0.0022 (15)
C260.033 (2)0.023 (2)0.032 (2)0.0046 (16)0.0036 (16)0.0052 (16)
N40.0364 (17)0.0246 (17)0.0265 (16)0.0041 (13)0.0071 (13)0.0043 (13)
N50.057 (2)0.0199 (18)0.0309 (18)0.0082 (16)0.0117 (16)0.0045 (15)
N60.0298 (17)0.0297 (19)0.0373 (19)0.0056 (14)0.0041 (14)0.0019 (15)
O90.0505 (18)0.0277 (16)0.0605 (19)0.0122 (13)0.0210 (15)0.0159 (14)
O100.075 (2)0.051 (2)0.0318 (16)0.0285 (17)0.0119 (15)0.0012 (14)
Geometric parameters (Å, º) top
C1—C61.373 (5)C15—C201.425 (5)
C1—C21.382 (5)C16—C171.354 (7)
C1—N11.474 (5)C16—H160.95
C2—C31.376 (5)C17—C181.400 (6)
C2—H20.95C17—H170.95
C3—C41.380 (6)C18—C191.360 (5)
C3—N21.458 (5)C18—H180.95
C4—C51.380 (6)C19—C201.434 (6)
C4—H40.95C19—H190.95
C5—C61.383 (5)C21—O81.227 (5)
C5—N31.470 (5)C21—O71.309 (5)
C6—H60.95O7—H70.95 (5)
N1—O11.212 (4)C22—N51.321 (5)
N1—O21.227 (4)C22—N41.359 (5)
N2—O41.222 (5)C22—C231.418 (5)
N2—O31.240 (5)C23—C241.347 (6)
N3—O51.221 (5)C23—H230.95
N3—O61.222 (5)C24—C251.403 (5)
C11—C121.378 (5)C24—H240.95
C11—C201.417 (5)C25—C261.368 (5)
C11—C211.495 (5)C25—N61.447 (5)
C12—C131.400 (6)C26—N41.325 (5)
C12—H120.95C26—H260.95
C13—C141.380 (6)N5—H5A0.90 (5)
C13—H130.95N5—H5B0.86 (4)
C14—C151.416 (6)N6—O91.207 (4)
C14—H140.95N6—O101.237 (4)
C15—C161.416 (6)
C6—C1—C2124.0 (3)C17—C16—C15121.7 (4)
C6—C1—N1117.9 (3)C17—C16—H16119.2
C2—C1—N1118.1 (3)C15—C16—H16119.2
C3—C2—C1116.6 (4)C16—C17—C18119.7 (4)
C3—C2—H2121.7C16—C17—H17120.2
C1—C2—H2121.7C18—C17—H17120.2
C2—C3—C4122.5 (4)C19—C18—C17121.1 (4)
C2—C3—N2118.5 (4)C19—C18—H18119.4
C4—C3—N2119.0 (4)C17—C18—H18119.4
C5—C4—C3117.8 (4)C18—C19—C20121.0 (4)
C5—C4—H4121.1C18—C19—H19119.5
C3—C4—H4121.1C20—C19—H19119.5
C4—C5—C6122.5 (4)C11—C20—C15118.9 (4)
C4—C5—N3119.3 (3)C11—C20—C19123.7 (3)
C6—C5—N3118.2 (4)C15—C20—C19117.3 (4)
C1—C6—C5116.5 (4)O8—C21—O7123.2 (3)
C1—C6—H6121.7O8—C21—C11123.2 (4)
C5—C6—H6121.7O7—C21—C11113.5 (3)
O1—N1—O2124.1 (3)C21—O7—H7112 (3)
O1—N1—C1118.0 (3)N5—C22—N4116.8 (3)
O2—N1—C1117.9 (3)N5—C22—C23121.9 (4)
O4—N2—O3124.1 (4)N4—C22—C23121.3 (3)
O4—N2—C3118.1 (4)C24—C23—C22119.4 (4)
O3—N2—C3117.8 (4)C24—C23—H23120.3
O5—N3—O6124.9 (4)C22—C23—H23120.3
O5—N3—C5116.9 (4)C23—C24—C25118.4 (3)
O6—N3—C5118.1 (3)C23—C24—H24120.8
C12—C11—C20119.2 (3)C25—C24—H24120.8
C12—C11—C21118.9 (3)C26—C25—C24119.7 (4)
C20—C11—C21121.9 (3)C26—C25—N6119.4 (3)
C11—C12—C13122.8 (4)C24—C25—N6120.9 (3)
C11—C12—H12118.6N4—C26—C25122.9 (4)
C13—C12—H12118.6N4—C26—H26118.5
C14—C13—C12118.5 (4)C25—C26—H26118.5
C14—C13—H13120.7C26—N4—C22118.2 (3)
C12—C13—H13120.7C22—N5—H5A123 (3)
C13—C14—C15121.1 (4)C22—N5—H5B116 (3)
C13—C14—H14119.5H5A—N5—H5B121 (4)
C15—C14—H14119.5O9—N6—O10123.2 (3)
C14—C15—C16121.4 (4)O9—N6—C25118.9 (3)
C14—C15—C20119.4 (4)O10—N6—C25117.9 (3)
C16—C15—C20119.1 (4)
C6—C1—C2—C31.8 (6)C15—C16—C17—C181.0 (7)
N1—C1—C2—C3176.7 (3)C16—C17—C18—C190.3 (7)
C1—C2—C3—C41.7 (6)C17—C18—C19—C200.6 (6)
C1—C2—C3—N2179.1 (3)C12—C11—C20—C150.8 (5)
C2—C3—C4—C50.2 (6)C21—C11—C20—C15177.1 (3)
N2—C3—C4—C5179.1 (3)C12—C11—C20—C19177.0 (4)
C3—C4—C5—C62.1 (6)C21—C11—C20—C195.1 (5)
C3—C4—C5—N3179.5 (3)C14—C15—C20—C110.8 (5)
C2—C1—C6—C50.1 (6)C16—C15—C20—C11179.5 (3)
N1—C1—C6—C5178.4 (3)C14—C15—C20—C19178.8 (4)
C4—C5—C6—C11.9 (5)C16—C15—C20—C191.6 (5)
N3—C5—C6—C1179.6 (3)C18—C19—C20—C11178.2 (4)
C6—C1—N1—O119.8 (5)C18—C19—C20—C150.3 (5)
C2—C1—N1—O1158.8 (4)C12—C11—C21—O8142.1 (4)
C6—C1—N1—O2161.4 (4)C20—C11—C21—O835.8 (5)
C2—C1—N1—O220.0 (5)C12—C11—C21—O736.5 (5)
C2—C3—N2—O4178.1 (4)C20—C11—C21—O7145.6 (3)
C4—C3—N2—O42.6 (5)N5—C22—C23—C24179.8 (4)
C2—C3—N2—O31.5 (5)N4—C22—C23—C241.7 (5)
C4—C3—N2—O3177.8 (4)C22—C23—C24—C251.0 (5)
C4—C5—N3—O56.4 (5)C23—C24—C25—C260.1 (5)
C6—C5—N3—O5172.1 (4)C23—C24—C25—N6178.6 (3)
C4—C5—N3—O6173.2 (4)C24—C25—C26—N40.1 (6)
C6—C5—N3—O68.3 (5)N6—C25—C26—N4178.8 (3)
C20—C11—C12—C131.8 (6)C25—C26—N4—C220.5 (5)
C21—C11—C12—C13176.1 (4)N5—C22—N4—C26179.7 (3)
C11—C12—C13—C141.0 (6)C23—C22—N4—C261.5 (5)
C12—C13—C14—C150.7 (6)C26—C25—N6—O91.0 (5)
C13—C14—C15—C16178.7 (4)C24—C25—N6—O9177.7 (3)
C13—C14—C15—C201.6 (6)C26—C25—N6—O10178.0 (3)
C14—C15—C16—C17178.4 (4)C24—C25—N6—O103.4 (5)
C20—C15—C16—C171.9 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···O80.90 (5)2.03 (5)2.919 (5)168 (5)
N5—H5B···O9i0.86 (4)2.24 (4)3.069 (5)161 (4)
O7—H7···N40.95 (5)1.71 (5)2.650 (4)171 (5)
C23—H23···O9i0.952.53.272 (5)139
C26—H26···O10.952.693.530 (5)147
C26—H26···O20.952.723.477 (5)138
Symmetry code: (i) x, y1, z.
Centroid distances (Å) between the trinitrobenzene and the ring centroids (Cg) of the aromatic polycyclics top
StructureDonorAcceptorCg···CgSymmetry operator
(I)C1–C6C11–C203.3745 (2)x, y, z
(II)C1–C6C11–C243.5173 (11)x, y, z
(III)C1–C6C11–C163.6587 (14)1 - x, 1 - y, 1 - z
(III)C1–C6C19–C244.6432 (18)x, y, z
(IV)C1–C6C11–C204.0417 (8)x, y + 1, z
Proportion (%) of intermolecular contacts between donor and acceptor molecules in the Hirshfeld fingerprint plots top
StructureC···CH···HC···H
(I)12.010.71.5
(II)12.66.60.9
(III)4.411.05.4
(IV)7.58.84.6
 

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