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The asymmetric unit of the title compound, C21H15Cl2N5O4, contains two independent mol­ecules (A and B) having similar conformations. The amine (NH2) group forms an intra­molecular hydrogen bond with the benzoyl group, giving an S(6) ring motif in both mol­ecules. The central six-membered rings adopt sofa conformations and the imidazole rings are planar (r.m.s deviations = 0.0150 and 0.0166 Å). The pyridine and imidazole rings are inclined to one another by 3.54 (1) and 3.03 (1)° in mol­ecules A and B, respectively. In the crystal, mol­ecules are linked by N—H...O hydrogen bonds, forming chains along the a axis which enclose R22(16) ring motifs. The rings are linked by weak N—H...O and C—H...O hydrogen bonds and C—H...π inter­actions forming sheets lying parallel to (001). A region of disordered electron density, most probably disordered solvent mol­ecules, occupying voids of ca 753 Å3 for an electron count of 260, was treated using the SQUEEZE routine in PLATON [Spek (2009). Acta Cryst. D65, 148–155]. Their formula mass and unit-cell characteristics were not taken into account during refinement.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536814017486/su2757sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536814017486/su2757Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536814017486/su2757Isup3.cml
Supplementary material

CCDC reference: 1016869

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.058
  • wR factor = 0.181
  • Data-to-parameter ratio = 19.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT242_ALERT_2_C Low Ueq as Compared to Neighbors for ..... C35A Check PLAT242_ALERT_2_C Low Ueq as Compared to Neighbors for ..... C35B Check PLAT334_ALERT_2_C Small Average Benzene C-C Dist. C32A -C37A 1.37 Ang. PLAT334_ALERT_2_C Small Average Benzene C-C Dist. C32B -C37B 1.37 Ang. PLAT420_ALERT_2_C D-H Without Acceptor N2A - H9 ... Please Check PLAT420_ALERT_2_C D-H Without Acceptor N2B - H11 ... Please Check PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 13.886 Check PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 2.667 Check PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 7 Report PLAT918_ALERT_3_C Reflection(s) with I(obs) much smaller I(calc) . 3 Check
Alert level G PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ... 4 Report PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF Please Do ! PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 8 Report PLAT154_ALERT_1_G The su's on the Cell Angles are Equal .......... 0.00200 Degree PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check PLAT606_ALERT_4_G VERY LARGE Solvent Accessible VOID(S) in Structure ! Info PLAT793_ALERT_4_G The Model has Chirality at C2A ............. S Verify PLAT793_ALERT_4_G The Model has Chirality at C2B ............. R Verify PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 2 Note PLAT869_ALERT_4_G ALERTS Related to the use of SQUEEZE Suppressed ! Info PLAT910_ALERT_3_G Missing # of FCF Reflections Below Th(Min) ..... 1 Report PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 40 Note PLAT961_ALERT_5_G Dataset Contains no Negative Intensities ....... Please Check
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 10 ALERT level C = Check. Ensure it is not caused by an omission or oversight 14 ALERT level G = General information/check it is not something unexpected 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 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 5 ALERT type 4 Improvement, methodology, query or suggestion 3 ALERT type 5 Informative message, check

Synthesis and crystallization top

A mixture of 4-chloro­benzoyl­aceto­nitrile (1.0 mmol), 5-chloro­isatin (1.0 mmol) and 2-(nitro­methyl­ene)imidazolidine were dissolved in 10 ml of EtOH and tri­ethyl­amine (1.0 mmol) was added and the reaction mixture was heated to reflux for 45 min. After completion of the reaction, as evident from TLC, the precipitate was filtered and dried to obtain pure pale brown solid. Colourless crystals of the title compound were obtaind by slow evaporation of a solution in di­methyl sulphoxide (yield 93 %; m.p. 534 K).

Refinement top

H atoms were placed in calculated positions and treated as riding atoms: N—H = 0.86 Å, C—H = 0.93 (aromatic CH), 0.96 (methyl CH3) and 0.97 Å (methyl­ene CH2) with Uiso(H) = 1.5Ueq(C-methyl) and = 1.2Ueq(N,C) for other H atoms. A region of disordered electron density, most probably disordered solvent molecules, occupying voids of ca. 753 Å3 for an electron count of 260, was treated using the SQUEEZE routine in PLATON [Spek (2009). Acta Cryst. D65, 148-155]. Their formula mass and unit-cell characteristics were not taken into account during refinement.

Related literature top

For a similar structure, a pharmacologically active pyridine-related compound, see: Nagalakshmi et al. (2014).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of molecule A of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 20% probability level. H-atoms have been omitted for clarity.
[Figure 2] Fig. 2. The molecular structure of molecule B of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 20% probability level. H-atoms have been omitted for clarity.
[Figure 3] Fig. 3. A view along the a axis of the crystal packing of the title compound. Dashed bonds represent N-H···O hydrogen bonds (see Table 1 for details; C bound H atoms have been omitted for clarity).
5-Amino-5'-chloro-6-(4-chlorobenzoyl)-8-nitro-2,3-dihydro-1H-spiro[imidazo[1,2-a]pyridine-7,3'-indolin]-2'-one top
Crystal data top
C21H15Cl2N5O4Z = 4
Mr = 472.28F(000) = 968
Triclinic, P1Dx = 1.173 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.9805 (7) ÅCell parameters from 2000 reflections
b = 13.2085 (8) Åθ = 2–31°
c = 16.7175 (10) ŵ = 0.27 mm1
α = 105.713 (2)°T = 293 K
β = 103.367 (2)°Block, colourless
γ = 91.051 (2)°0.21 × 0.19 × 0.18 mm
V = 2674.4 (3) Å3
Data collection top
Bruker Kappa APEXII
diffractometer
11499 independent reflections
Radiation source: fine-focus sealed tube7063 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
Detector resolution: 0 pixels mm-1θmax = 26.9°, θmin = 1.6°
ω and ϕ scansh = 1616
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
k = 1616
Tmin = 0.967, Tmax = 0.974l = 2121
87748 measured 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: inferred from neighbouring sites
wR(F2) = 0.181H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.0894P)2 + 0.2555P]
where P = (Fo2 + 2Fc2)/3
11499 reflections(Δ/σ)max < 0.001
577 parametersΔρmax = 0.38 e Å3
2 restraintsΔρmin = 0.31 e Å3
Crystal data top
C21H15Cl2N5O4γ = 91.051 (2)°
Mr = 472.28V = 2674.4 (3) Å3
Triclinic, P1Z = 4
a = 12.9805 (7) ÅMo Kα radiation
b = 13.2085 (8) ŵ = 0.27 mm1
c = 16.7175 (10) ÅT = 293 K
α = 105.713 (2)°0.21 × 0.19 × 0.18 mm
β = 103.367 (2)°
Data collection top
Bruker Kappa APEXII
diffractometer
11499 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
7063 reflections with I > 2σ(I)
Tmin = 0.967, Tmax = 0.974Rint = 0.044
87748 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0582 restraints
wR(F2) = 0.181H-atom parameters constrained
S = 1.11Δρmax = 0.38 e Å3
11499 reflectionsΔρmin = 0.31 e Å3
577 parameters
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
xyzUiso*/Ueq
C1A0.73023 (17)0.01119 (19)0.11139 (15)0.0368 (5)
C1B0.25621 (18)0.57859 (18)0.12320 (15)0.0374 (5)
C2A0.72616 (16)0.11182 (17)0.17862 (14)0.0316 (5)
C2B0.24268 (17)0.51805 (17)0.18571 (15)0.0346 (5)
C3A0.61102 (16)0.13082 (17)0.18449 (15)0.0338 (5)
C3B0.12348 (17)0.50010 (17)0.18260 (14)0.0331 (5)
C4A0.53098 (17)0.04635 (18)0.14696 (16)0.0369 (5)
C4B0.04671 (18)0.55272 (17)0.13823 (15)0.0351 (5)
C5A0.64378 (18)0.06481 (18)0.07503 (15)0.0374 (5)
C5B0.17571 (19)0.62288 (18)0.07933 (15)0.0376 (5)
C6A0.5327 (2)0.2160 (2)0.0028 (2)0.0587 (7)
H10.53850.27830.02320.070*
H20.49970.23710.05820.070*
C6B0.0723 (2)0.7147 (2)0.00442 (19)0.0544 (7)
H30.04820.68750.06630.065*
H40.07460.79110.01150.065*
C7A0.4711 (2)0.1373 (2)0.05076 (18)0.0514 (7)
H50.41090.11950.01190.062*
H60.44560.16400.09200.062*
C7B0.0004 (2)0.6690 (2)0.03965 (17)0.0464 (6)
H70.02750.72440.07810.056*
H80.05820.62290.00180.056*
C8A0.78204 (18)0.20686 (19)0.15986 (16)0.0387 (6)
C8B0.2955 (2)0.4118 (2)0.16477 (18)0.0431 (6)
C9A0.87762 (17)0.19669 (18)0.28932 (15)0.0346 (5)
C9B0.38129 (18)0.5008 (2)0.30110 (17)0.0419 (6)
C10A0.79719 (16)0.11549 (17)0.26521 (14)0.0313 (5)
C10B0.30771 (17)0.56908 (18)0.27676 (15)0.0352 (5)
C11A0.78829 (18)0.05466 (18)0.31873 (15)0.0366 (5)
H11A0.73470.00030.30300.044*
C11B0.29907 (19)0.66252 (19)0.33363 (16)0.0410 (6)
H11B0.25030.70860.31790.049*
C12A0.8622 (2)0.0776 (2)0.39682 (16)0.0450 (6)
C12B0.3646 (2)0.6868 (2)0.41515 (17)0.0515 (6)
C13A0.9416 (2)0.1583 (2)0.42154 (18)0.0540 (7)
H13A0.98850.17320.47530.065*
C13B0.4378 (2)0.6207 (3)0.44003 (19)0.0598 (7)
H13B0.48050.63920.49570.072*
C14A0.9517 (2)0.2178 (2)0.36629 (17)0.0480 (6)
H14A1.00700.27030.38110.058*
C14B0.4481 (2)0.5263 (2)0.3822 (2)0.0570 (7)
H14B0.49850.48150.39770.068*
C31A0.58488 (19)0.2271 (2)0.23432 (18)0.0440 (6)
C31B0.08794 (18)0.43654 (18)0.22841 (15)0.0378 (5)
C32A0.6616 (2)0.32226 (19)0.27750 (18)0.0447 (6)
C32B0.15700 (18)0.36977 (19)0.27329 (16)0.0384 (6)
C33A0.7186 (2)0.3388 (2)0.36101 (19)0.0568 (7)
H33A0.71200.28920.39020.068*
C33B0.2000 (2)0.4052 (2)0.36081 (17)0.0512 (7)
H33B0.19200.47370.39100.061*
C34A0.7868 (3)0.4317 (3)0.4018 (2)0.0725 (9)
H34A0.82460.44410.45860.087*
C34B0.2551 (2)0.3383 (3)0.4037 (2)0.0655 (8)
H34B0.28490.36220.46250.079*
C35A0.7976 (3)0.5016 (2)0.3598 (2)0.0720 (9)
C35B0.2651 (3)0.2381 (3)0.3594 (2)0.0705 (9)
C36A0.7365 (3)0.4889 (2)0.2770 (2)0.0674 (9)
H36A0.74090.54070.24930.081*
C36B0.2220 (2)0.2015 (2)0.2736 (2)0.0613 (8)
H36B0.22960.13260.24410.074*
C37A0.6699 (2)0.3989 (2)0.2368 (2)0.0553 (7)
H37A0.62950.38930.18120.066*
C37B0.1672 (2)0.2668 (2)0.23076 (18)0.0522 (7)
H37B0.13660.24130.17230.063*
N1A0.82389 (17)0.01200 (18)0.09059 (15)0.0521 (6)
N1B0.35638 (17)0.59169 (17)0.11129 (14)0.0462 (5)
N2A0.43450 (16)0.05275 (18)0.15897 (17)0.0598 (7)
H90.38720.00040.13390.072*
H100.41860.10930.19190.072*
N2B0.05243 (15)0.55052 (17)0.14117 (14)0.0487 (5)
H110.09620.58340.11230.058*
H120.07430.51620.17200.058*
N3A0.86499 (15)0.24959 (15)0.22690 (13)0.0396 (5)
H3A0.90560.30370.23060.047*
N3B0.37179 (15)0.41016 (16)0.23522 (15)0.0455 (5)
H3B0.40990.35810.23820.055*
N4A0.54899 (14)0.04556 (15)0.09405 (13)0.0380 (5)
N4B0.07354 (15)0.60967 (15)0.08717 (13)0.0389 (5)
N5A0.63672 (17)0.15890 (16)0.02111 (14)0.0494 (5)
H5A0.68770.18420.00100.059*
N5B0.17403 (17)0.68062 (16)0.02601 (13)0.0470 (5)
H5B0.22970.69650.01080.056*
O1A0.83315 (16)0.09805 (16)0.03680 (14)0.0713 (6)
O1B0.37291 (15)0.64175 (16)0.06023 (14)0.0649 (6)
O2A0.90296 (14)0.05404 (16)0.12491 (13)0.0658 (6)
O2B0.43195 (15)0.55275 (17)0.15150 (14)0.0625 (5)
O3A0.75237 (14)0.23385 (15)0.09537 (11)0.0525 (5)
O3B0.27203 (16)0.34371 (14)0.09631 (13)0.0573 (5)
O4A0.49204 (14)0.24063 (15)0.24575 (16)0.0674 (6)
O4B0.00657 (13)0.42797 (14)0.23356 (12)0.0522 (5)
Cl10.85274 (7)0.00066 (7)0.46504 (5)0.0701 (2)
Cl20.88459 (12)0.61410 (9)0.40925 (9)0.1355 (5)
Cl30.35428 (8)0.80620 (7)0.48853 (5)0.0795 (3)
Cl40.33373 (11)0.15562 (10)0.41399 (9)0.1317 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0333 (12)0.0421 (14)0.0393 (13)0.0009 (10)0.0141 (10)0.0147 (11)
C1B0.0401 (13)0.0322 (12)0.0439 (14)0.0005 (10)0.0169 (11)0.0121 (11)
C2A0.0291 (11)0.0337 (12)0.0363 (12)0.0016 (9)0.0094 (9)0.0161 (10)
C2B0.0329 (12)0.0300 (12)0.0437 (13)0.0007 (9)0.0127 (10)0.0126 (10)
C3A0.0276 (11)0.0340 (12)0.0452 (14)0.0001 (9)0.0082 (10)0.0211 (11)
C3B0.0331 (11)0.0306 (12)0.0387 (13)0.0021 (9)0.0119 (10)0.0121 (10)
C4A0.0266 (11)0.0384 (13)0.0527 (15)0.0051 (10)0.0086 (10)0.0250 (12)
C4B0.0377 (12)0.0266 (11)0.0428 (13)0.0002 (9)0.0147 (10)0.0092 (10)
C5A0.0448 (14)0.0368 (13)0.0352 (13)0.0020 (10)0.0086 (11)0.0190 (11)
C5B0.0462 (14)0.0284 (12)0.0378 (13)0.0081 (10)0.0140 (11)0.0062 (10)
C6A0.0625 (18)0.0456 (16)0.0588 (18)0.0109 (14)0.0047 (14)0.0091 (14)
C6B0.0631 (18)0.0467 (16)0.0551 (17)0.0054 (13)0.0046 (14)0.0262 (14)
C7A0.0420 (14)0.0478 (16)0.0583 (17)0.0159 (12)0.0021 (12)0.0185 (13)
C7B0.0533 (15)0.0392 (14)0.0484 (15)0.0080 (12)0.0071 (12)0.0195 (12)
C8A0.0370 (13)0.0404 (13)0.0458 (15)0.0007 (10)0.0135 (11)0.0210 (12)
C8B0.0468 (14)0.0382 (14)0.0528 (16)0.0038 (11)0.0258 (13)0.0153 (13)
C9A0.0287 (11)0.0335 (12)0.0433 (14)0.0022 (9)0.0117 (10)0.0111 (10)
C9B0.0337 (12)0.0458 (15)0.0560 (16)0.0050 (11)0.0159 (12)0.0264 (13)
C10A0.0272 (11)0.0329 (12)0.0373 (12)0.0051 (9)0.0106 (9)0.0135 (10)
C10B0.0304 (11)0.0336 (12)0.0472 (14)0.0001 (9)0.0122 (10)0.0185 (11)
C11A0.0354 (12)0.0375 (13)0.0398 (13)0.0017 (10)0.0122 (10)0.0133 (11)
C11B0.0403 (13)0.0382 (14)0.0480 (15)0.0041 (11)0.0134 (12)0.0158 (12)
C12A0.0464 (14)0.0518 (16)0.0438 (15)0.0127 (12)0.0123 (12)0.0234 (12)
C12B0.0568 (16)0.0493 (13)0.0458 (16)0.0084 (13)0.0116 (13)0.0109 (10)
C13A0.0505 (16)0.0576 (17)0.0457 (16)0.0044 (13)0.0027 (13)0.0135 (14)
C13B0.0502 (16)0.0732 (17)0.0550 (18)0.0099 (15)0.0002 (13)0.0286 (13)
C14A0.0411 (14)0.0469 (15)0.0494 (16)0.0024 (12)0.0022 (12)0.0108 (13)
C14B0.0417 (14)0.0625 (15)0.076 (2)0.0026 (13)0.0063 (14)0.0413 (13)
C31A0.0343 (13)0.0439 (15)0.0621 (17)0.0059 (11)0.0152 (12)0.0258 (13)
C31B0.0384 (13)0.0347 (13)0.0426 (14)0.0016 (10)0.0127 (11)0.0125 (11)
C32A0.0450 (14)0.0359 (14)0.0596 (17)0.0096 (11)0.0250 (13)0.0134 (12)
C32B0.0352 (12)0.0405 (14)0.0468 (15)0.0007 (10)0.0130 (11)0.0222 (12)
C33A0.0646 (18)0.0522 (17)0.0576 (19)0.0059 (14)0.0272 (15)0.0118 (14)
C33B0.0536 (16)0.0526 (17)0.0474 (16)0.0011 (13)0.0112 (13)0.0157 (13)
C34A0.086 (2)0.068 (2)0.0472 (18)0.0129 (18)0.0137 (16)0.0079 (16)
C34B0.0640 (19)0.071 (2)0.0616 (19)0.0087 (16)0.0005 (15)0.0338 (17)
C35A0.081 (2)0.0463 (18)0.081 (2)0.0130 (16)0.033 (2)0.0047 (17)
C35B0.065 (2)0.066 (2)0.085 (3)0.0012 (16)0.0011 (18)0.046 (2)
C36A0.081 (2)0.0403 (16)0.083 (2)0.0071 (15)0.0272 (19)0.0157 (16)
C36B0.0632 (18)0.0380 (15)0.085 (2)0.0083 (14)0.0178 (17)0.0209 (16)
C37A0.0612 (17)0.0410 (15)0.0678 (19)0.0065 (13)0.0170 (15)0.0209 (14)
C37B0.0610 (17)0.0420 (15)0.0532 (17)0.0061 (13)0.0111 (13)0.0164 (13)
N1A0.0467 (13)0.0525 (14)0.0562 (14)0.0067 (11)0.0252 (11)0.0036 (12)
N1B0.0464 (12)0.0459 (12)0.0585 (14)0.0024 (10)0.0261 (11)0.0238 (11)
N2A0.0328 (11)0.0460 (13)0.102 (2)0.0006 (10)0.0170 (12)0.0228 (13)
N2B0.0347 (11)0.0559 (14)0.0679 (15)0.0057 (10)0.0138 (10)0.0365 (12)
N3A0.0358 (11)0.0369 (11)0.0478 (12)0.0079 (9)0.0113 (9)0.0148 (9)
N3B0.0367 (11)0.0390 (12)0.0701 (15)0.0128 (9)0.0203 (11)0.0242 (11)
N4A0.0333 (10)0.0332 (11)0.0465 (12)0.0054 (8)0.0038 (9)0.0150 (9)
N4B0.0395 (11)0.0374 (11)0.0458 (12)0.0034 (9)0.0114 (9)0.0207 (9)
N5A0.0550 (13)0.0415 (13)0.0496 (13)0.0063 (10)0.0164 (11)0.0072 (11)
N5B0.0540 (13)0.0450 (12)0.0484 (13)0.0026 (10)0.0123 (10)0.0245 (10)
O1A0.0693 (13)0.0580 (13)0.0798 (15)0.0087 (10)0.0425 (12)0.0111 (11)
O1B0.0609 (12)0.0743 (14)0.0861 (15)0.0016 (10)0.0382 (11)0.0497 (12)
O2A0.0440 (11)0.0638 (13)0.0797 (15)0.0131 (10)0.0311 (10)0.0082 (11)
O2B0.0429 (10)0.0775 (14)0.0871 (15)0.0110 (10)0.0309 (10)0.0434 (12)
O3A0.0560 (11)0.0606 (12)0.0487 (11)0.0107 (9)0.0099 (9)0.0320 (10)
O3B0.0764 (13)0.0379 (10)0.0635 (13)0.0091 (9)0.0317 (11)0.0116 (10)
O4A0.0416 (10)0.0435 (11)0.1263 (19)0.0142 (8)0.0356 (12)0.0259 (12)
O4B0.0394 (10)0.0571 (11)0.0744 (13)0.0009 (8)0.0194 (9)0.0379 (10)
Cl10.0825 (5)0.0836 (6)0.0548 (5)0.0085 (4)0.0105 (4)0.0422 (4)
Cl20.1648 (12)0.0872 (8)0.1189 (10)0.0690 (8)0.0301 (8)0.0201 (7)
Cl30.1047 (7)0.0664 (5)0.0559 (5)0.0044 (5)0.0201 (4)0.0011 (4)
Cl40.1366 (10)0.1045 (9)0.1475 (11)0.0217 (7)0.0301 (8)0.0787 (8)
Geometric parameters (Å, º) top
C1A—N1A1.358 (3)C11A—H11A0.9300
C1A—C5A1.396 (3)C11B—C12B1.379 (4)
C1A—C2A1.501 (3)C11B—H11B0.9300
C1B—C5B1.368 (3)C12A—C13A1.376 (4)
C1B—N1B1.375 (3)C12A—Cl11.743 (3)
C1B—C2B1.515 (3)C12B—C13B1.372 (4)
C2A—C10A1.514 (3)C12B—Cl31.745 (3)
C2A—C3A1.541 (3)C13A—C14A1.390 (4)
C2A—C8A1.577 (3)C13A—H13A0.9300
C2B—C10B1.521 (3)C13B—C14B1.385 (4)
C2B—C3B1.548 (3)C13B—H13B0.9300
C2B—C8B1.563 (3)C14A—H14A0.9300
C3A—C4A1.412 (3)C14B—H14B0.9300
C3A—C31A1.414 (3)C31A—O4A1.271 (3)
C3B—C4B1.410 (3)C31A—C32A1.491 (4)
C3B—C31B1.415 (3)C31B—O4B1.255 (3)
C4A—N2A1.314 (3)C31B—C32B1.490 (3)
C4A—N4A1.355 (3)C32A—C33A1.376 (4)
C4B—N2B1.299 (3)C32A—C37A1.379 (4)
C4B—N4B1.375 (3)C32B—C37B1.378 (4)
C5A—N5A1.310 (3)C32B—C33B1.383 (3)
C5A—N4A1.352 (3)C33A—C34A1.408 (4)
C5B—N5B1.318 (3)C33A—H33A0.9300
C5B—N4B1.375 (3)C33B—C34B1.391 (4)
C6A—N5A1.460 (3)C33B—H33B0.9300
C6A—C7A1.497 (4)C34A—C35A1.326 (5)
C6A—H10.9700C34A—H34A0.9300
C6A—H20.9700C34B—C35B1.355 (5)
C6B—N5B1.428 (3)C34B—H34B0.9300
C6B—C7B1.522 (4)C35A—C36A1.392 (5)
C6B—H30.9700C35A—Cl21.734 (3)
C6B—H40.9700C35B—C36B1.359 (4)
C7A—N4A1.469 (3)C35B—Cl41.736 (3)
C7A—H50.9700C36A—C37A1.369 (4)
C7A—H60.9700C36A—H36A0.9300
C7B—N4B1.470 (3)C36B—C37B1.373 (4)
C7B—H70.9700C36B—H36B0.9300
C7B—H80.9700C37A—H37A0.9300
C8A—O3A1.208 (3)C37B—H37B0.9300
C8A—N3A1.346 (3)N1A—O2A1.252 (3)
C8B—O3B1.218 (3)N1A—O1A1.271 (3)
C8B—N3B1.358 (3)N1B—O2B1.257 (3)
C9A—C14A1.372 (3)N1B—O1B1.264 (3)
C9A—N3A1.387 (3)N2A—H90.8600
C9A—C10A1.390 (3)N2A—H100.8600
C9B—N3B1.371 (3)N2B—H110.8600
C9B—C14B1.380 (4)N2B—H120.8600
C9B—C10B1.394 (3)N3A—H3A0.8600
C10A—C11A1.376 (3)N3B—H3B0.8600
C10B—C11B1.363 (3)N5A—H5A0.8600
C11A—C12A1.383 (3)N5B—H5B0.8600
N1A—C1A—C5A118.1 (2)C13B—C12B—C11B122.2 (3)
N1A—C1A—C2A119.2 (2)C13B—C12B—Cl3119.2 (2)
C5A—C1A—C2A122.4 (2)C11B—C12B—Cl3118.6 (2)
C5B—C1B—N1B118.0 (2)C12A—C13A—C14A120.1 (2)
C5B—C1B—C2B124.2 (2)C12A—C13A—H13A119.9
N1B—C1B—C2B117.7 (2)C14A—C13A—H13A119.9
C1A—C2A—C10A112.31 (18)C12B—C13B—C14B120.0 (3)
C1A—C2A—C3A111.22 (18)C12B—C13B—H13B120.0
C10A—C2A—C3A111.30 (17)C14B—C13B—H13B120.0
C1A—C2A—C8A109.75 (17)C9A—C14A—C13A118.0 (2)
C10A—C2A—C8A99.90 (17)C9A—C14A—H14A121.0
C3A—C2A—C8A111.88 (18)C13A—C14A—H14A121.0
C1B—C2B—C10B113.39 (18)C9B—C14B—C13B118.0 (3)
C1B—C2B—C3B110.24 (18)C9B—C14B—H14B121.0
C10B—C2B—C3B111.44 (18)C13B—C14B—H14B121.0
C1B—C2B—C8B109.31 (18)O4A—C31A—C3A122.5 (2)
C10B—C2B—C8B100.11 (19)O4A—C31A—C32A113.5 (2)
C3B—C2B—C8B112.00 (18)C3A—C31A—C32A124.0 (2)
C4A—C3A—C31A118.5 (2)O4B—C31B—C3B123.4 (2)
C4A—C3A—C2A119.3 (2)O4B—C31B—C32B112.48 (19)
C31A—C3A—C2A121.84 (19)C3B—C31B—C32B124.1 (2)
C4B—C3B—C31B117.4 (2)C33A—C32A—C37A119.1 (3)
C4B—C3B—C2B120.74 (19)C33A—C32A—C31A120.3 (2)
C31B—C3B—C2B121.8 (2)C37A—C32A—C31A120.4 (3)
N2A—C4A—N4A116.1 (2)C37B—C32B—C33B118.6 (2)
N2A—C4A—C3A122.5 (2)C37B—C32B—C31B120.4 (2)
N4A—C4A—C3A121.37 (19)C33B—C32B—C31B120.3 (2)
N2B—C4B—N4B115.5 (2)C32A—C33A—C34A119.3 (3)
N2B—C4B—C3B123.7 (2)C32A—C33A—H33A120.3
N4B—C4B—C3B120.8 (2)C34A—C33A—H33A120.3
N5A—C5A—N4A109.7 (2)C32B—C33B—C34B120.1 (3)
N5A—C5A—C1A130.0 (2)C32B—C33B—H33B120.0
N4A—C5A—C1A120.3 (2)C34B—C33B—H33B120.0
N5B—C5B—C1B132.2 (2)C35A—C34A—C33A120.4 (3)
N5B—C5B—N4B107.5 (2)C35A—C34A—H34A119.8
C1B—C5B—N4B120.3 (2)C33A—C34A—H34A119.8
N5A—C6A—C7A103.5 (2)C35B—C34B—C33B119.5 (3)
N5A—C6A—H1111.1C35B—C34B—H34B120.2
C7A—C6A—H1111.1C33B—C34B—H34B120.2
N5A—C6A—H2111.1C34A—C35A—C36A121.1 (3)
C7A—C6A—H2111.1C34A—C35A—Cl2120.3 (3)
H1—C6A—H2109.0C36A—C35A—Cl2118.6 (3)
N5B—C6B—C7B103.9 (2)C34B—C35B—C36B121.2 (3)
N5B—C6B—H3111.0C34B—C35B—Cl4118.9 (3)
C7B—C6B—H3111.0C36B—C35B—Cl4119.8 (3)
N5B—C6B—H4111.0C37A—C36A—C35A118.8 (3)
C7B—C6B—H4111.0C37A—C36A—H36A120.6
H3—C6B—H4109.0C35A—C36A—H36A120.6
N4A—C7A—C6A103.4 (2)C35B—C36B—C37B119.7 (3)
N4A—C7A—H5111.1C35B—C36B—H36B120.2
C6A—C7A—H5111.1C37B—C36B—H36B120.2
N4A—C7A—H6111.1C36A—C37A—C32A121.2 (3)
C6A—C7A—H6111.1C36A—C37A—H37A119.4
H5—C7A—H6109.1C32A—C37A—H37A119.4
N4B—C7B—C6B102.0 (2)C36B—C37B—C32B120.9 (3)
N4B—C7B—H7111.4C36B—C37B—H37B119.6
C6B—C7B—H7111.4C32B—C37B—H37B119.6
N4B—C7B—H8111.4O2A—N1A—O1A119.3 (2)
C6B—C7B—H8111.4O2A—N1A—C1A118.8 (2)
H7—C7B—H8109.2O1A—N1A—C1A122.0 (2)
O3A—C8A—N3A128.0 (2)O2B—N1B—O1B119.92 (19)
O3A—C8A—C2A123.8 (2)O2B—N1B—C1B119.3 (2)
N3A—C8A—C2A108.21 (19)O1B—N1B—C1B120.8 (2)
O3B—C8B—N3B126.7 (2)C4A—N2A—H9120.0
O3B—C8B—C2B125.1 (2)C4A—N2A—H10120.0
N3B—C8B—C2B108.2 (2)H9—N2A—H10120.0
C14A—C9A—N3A129.1 (2)C4B—N2B—H11120.0
C14A—C9A—C10A121.4 (2)C4B—N2B—H12120.0
N3A—C9A—C10A109.4 (2)H11—N2B—H12120.0
N3B—C9B—C14B128.8 (2)C8A—N3A—C9A112.49 (18)
N3B—C9B—C10B109.9 (2)C8A—N3A—H3A123.8
C14B—C9B—C10B121.2 (3)C9A—N3A—H3A123.8
C11A—C10A—C9A120.9 (2)C8B—N3B—C9B112.4 (2)
C11A—C10A—C2A129.1 (2)C8B—N3B—H3B123.8
C9A—C10A—C2A109.95 (18)C9B—N3B—H3B123.8
C11B—C10B—C9B120.4 (2)C5A—N4A—C4A123.45 (19)
C11B—C10B—C2B130.2 (2)C5A—N4A—C7A110.8 (2)
C9B—C10B—C2B109.3 (2)C4A—N4A—C7A125.7 (2)
C10A—C11A—C12A117.4 (2)C5B—N4B—C4B122.8 (2)
C10A—C11A—H11A121.3C5B—N4B—C7B111.89 (19)
C12A—C11A—H11A121.3C4B—N4B—C7B125.18 (19)
C10B—C11B—C12B118.2 (2)C5A—N5A—C6A112.5 (2)
C10B—C11B—H11B120.9C5A—N5A—H5A123.8
C12B—C11B—H11B120.9C6A—N5A—H5A123.8
C13A—C12A—C11A122.2 (2)C5B—N5B—C6B114.6 (2)
C13A—C12A—Cl1119.8 (2)C5B—N5B—H5B122.7
C11A—C12A—Cl1118.0 (2)C6B—N5B—H5B122.7
N1A—C1A—C2A—C10A62.0 (3)Cl3—C12B—C13B—C14B179.1 (2)
C5A—C1A—C2A—C10A111.6 (2)N3A—C9A—C14A—C13A174.2 (2)
N1A—C1A—C2A—C3A172.5 (2)C10A—C9A—C14A—C13A2.7 (4)
C5A—C1A—C2A—C3A13.9 (3)C12A—C13A—C14A—C9A3.1 (4)
N1A—C1A—C2A—C8A48.2 (3)N3B—C9B—C14B—C13B175.6 (2)
C5A—C1A—C2A—C8A138.2 (2)C10B—C9B—C14B—C13B2.0 (4)
C5B—C1B—C2B—C10B117.6 (2)C12B—C13B—C14B—C9B1.6 (4)
N1B—C1B—C2B—C10B60.9 (3)C4A—C3A—C31A—O4A0.7 (4)
C5B—C1B—C2B—C3B8.1 (3)C2A—C3A—C31A—O4A173.7 (2)
N1B—C1B—C2B—C3B173.3 (2)C4A—C3A—C31A—C32A179.9 (2)
C5B—C1B—C2B—C8B131.6 (2)C2A—C3A—C31A—C32A6.9 (4)
N1B—C1B—C2B—C8B49.8 (3)C4B—C3B—C31B—O4B2.5 (4)
C1A—C2A—C3A—C4A16.1 (3)C2B—C3B—C31B—O4B173.4 (2)
C10A—C2A—C3A—C4A110.0 (2)C4B—C3B—C31B—C32B175.4 (2)
C8A—C2A—C3A—C4A139.2 (2)C2B—C3B—C31B—C32B8.8 (4)
C1A—C2A—C3A—C31A171.0 (2)O4A—C31A—C32A—C33A88.0 (3)
C10A—C2A—C3A—C31A63.0 (3)C3A—C31A—C32A—C33A92.6 (3)
C8A—C2A—C3A—C31A47.8 (3)O4A—C31A—C32A—C37A86.6 (3)
C1B—C2B—C3B—C4B10.7 (3)C3A—C31A—C32A—C37A92.8 (3)
C10B—C2B—C3B—C4B116.1 (2)O4B—C31B—C32B—C37B88.3 (3)
C8B—C2B—C3B—C4B132.7 (2)C3B—C31B—C32B—C37B89.7 (3)
C1B—C2B—C3B—C31B173.6 (2)O4B—C31B—C32B—C33B82.8 (3)
C10B—C2B—C3B—C31B59.6 (3)C3B—C31B—C32B—C33B99.1 (3)
C8B—C2B—C3B—C31B51.7 (3)C37A—C32A—C33A—C34A2.3 (4)
C31A—C3A—C4A—N2A2.4 (3)C31A—C32A—C33A—C34A177.0 (3)
C2A—C3A—C4A—N2A170.8 (2)C37B—C32B—C33B—C34B2.0 (4)
C31A—C3A—C4A—N4A175.7 (2)C31B—C32B—C33B—C34B173.3 (2)
C2A—C3A—C4A—N4A11.1 (3)C32A—C33A—C34A—C35A1.2 (5)
C31B—C3B—C4B—N2B3.9 (3)C32B—C33B—C34B—C35B0.9 (4)
C2B—C3B—C4B—N2B171.9 (2)C33A—C34A—C35A—C36A4.6 (5)
C31B—C3B—C4B—N4B175.2 (2)C33A—C34A—C35A—Cl2178.1 (2)
C2B—C3B—C4B—N4B8.9 (3)C33B—C34B—C35B—C36B0.1 (5)
N1A—C1A—C5A—N5A0.7 (4)C33B—C34B—C35B—Cl4179.8 (2)
C2A—C1A—C5A—N5A174.4 (2)C34A—C35A—C36A—C37A4.5 (5)
N1A—C1A—C5A—N4A179.7 (2)Cl2—C35A—C36A—C37A178.2 (2)
C2A—C1A—C5A—N4A6.0 (3)C34B—C35B—C36B—C37B0.0 (5)
N1B—C1B—C5B—N5B1.5 (4)Cl4—C35B—C36B—C37B179.6 (2)
C2B—C1B—C5B—N5B177.0 (2)C35A—C36A—C37A—C32A0.9 (4)
N1B—C1B—C5B—N4B178.2 (2)C33A—C32A—C37A—C36A2.4 (4)
C2B—C1B—C5B—N4B3.2 (4)C31A—C32A—C37A—C36A177.1 (3)
N5A—C6A—C7A—N4A2.3 (3)C35B—C36B—C37B—C32B1.2 (4)
N5B—C6B—C7B—N4B2.6 (3)C33B—C32B—C37B—C36B2.2 (4)
C1A—C2A—C8A—O3A61.2 (3)C31B—C32B—C37B—C36B173.5 (2)
C10A—C2A—C8A—O3A179.4 (2)C5A—C1A—N1A—O2A177.7 (2)
C3A—C2A—C8A—O3A62.7 (3)C2A—C1A—N1A—O2A3.8 (4)
C1A—C2A—C8A—N3A118.9 (2)C5A—C1A—N1A—O1A3.1 (4)
C10A—C2A—C8A—N3A0.7 (2)C2A—C1A—N1A—O1A177.0 (2)
C3A—C2A—C8A—N3A117.2 (2)C5B—C1B—N1B—O2B179.3 (2)
C1B—C2B—C8B—O3B58.4 (3)C2B—C1B—N1B—O2B0.6 (3)
C10B—C2B—C8B—O3B177.7 (2)C5B—C1B—N1B—O1B1.1 (3)
C3B—C2B—C8B—O3B64.1 (3)C2B—C1B—N1B—O1B179.8 (2)
C1B—C2B—C8B—N3B120.9 (2)O3A—C8A—N3A—C9A178.5 (2)
C10B—C2B—C8B—N3B1.5 (2)C2A—C8A—N3A—C9A1.7 (3)
C3B—C2B—C8B—N3B116.6 (2)C14A—C9A—N3A—C8A179.1 (2)
C14A—C9A—C10A—C11A1.1 (3)C10A—C9A—N3A—C8A2.0 (3)
N3A—C9A—C10A—C11A176.27 (19)O3B—C8B—N3B—C9B177.7 (2)
C14A—C9A—C10A—C2A178.8 (2)C2B—C8B—N3B—C9B1.5 (3)
N3A—C9A—C10A—C2A1.4 (2)C14B—C9B—N3B—C8B178.6 (2)
C1A—C2A—C10A—C11A66.7 (3)C10B—C9B—N3B—C8B0.8 (3)
C3A—C2A—C10A—C11A58.7 (3)N5A—C5A—N4A—C4A178.6 (2)
C8A—C2A—C10A—C11A177.0 (2)C1A—C5A—N4A—C4A1.0 (3)
C1A—C2A—C10A—C9A115.8 (2)N5A—C5A—N4A—C7A2.0 (3)
C3A—C2A—C10A—C9A118.7 (2)C1A—C5A—N4A—C7A178.3 (2)
C8A—C2A—C10A—C9A0.4 (2)N2A—C4A—N4A—C5A180.0 (2)
N3B—C9B—C10B—C11B176.9 (2)C3A—C4A—N4A—C5A1.8 (3)
C14B—C9B—C10B—C11B1.1 (3)N2A—C4A—N4A—C7A0.8 (3)
N3B—C9B—C10B—C2B0.3 (2)C3A—C4A—N4A—C7A179.0 (2)
C14B—C9B—C10B—C2B177.7 (2)C6A—C7A—N4A—C5A0.4 (3)
C1B—C2B—C10B—C11B66.5 (3)C6A—C7A—N4A—C4A178.9 (2)
C3B—C2B—C10B—C11B58.6 (3)N5B—C5B—N4B—C4B179.9 (2)
C8B—C2B—C10B—C11B177.2 (2)C1B—C5B—N4B—C4B0.0 (3)
C1B—C2B—C10B—C9B117.4 (2)N5B—C5B—N4B—C7B4.0 (3)
C3B—C2B—C10B—C9B117.5 (2)C1B—C5B—N4B—C7B176.2 (2)
C8B—C2B—C10B—C9B1.1 (2)N2B—C4B—N4B—C5B177.7 (2)
C9A—C10A—C11A—C12A0.0 (3)C3B—C4B—N4B—C5B3.1 (3)
C2A—C10A—C11A—C12A177.2 (2)N2B—C4B—N4B—C7B2.1 (3)
C9B—C10B—C11B—C12B0.1 (3)C3B—C4B—N4B—C7B178.7 (2)
C2B—C10B—C11B—C12B175.6 (2)C6B—C7B—N4B—C5B4.0 (3)
C10A—C11A—C12A—C13A0.6 (4)C6B—C7B—N4B—C4B179.9 (2)
C10A—C11A—C12A—Cl1179.50 (17)N4A—C5A—N5A—C6A3.8 (3)
C10B—C11B—C12B—C13B0.5 (4)C1A—C5A—N5A—C6A176.6 (2)
C10B—C11B—C12B—Cl3180.00 (18)C7A—C6A—N5A—C5A3.8 (3)
C11A—C12A—C13A—C14A2.2 (4)C1B—C5B—N5B—C6B178.1 (3)
Cl1—C12A—C13A—C14A177.9 (2)N4B—C5B—N5B—C6B2.2 (3)
C11B—C12B—C13B—C14B0.5 (4)C7B—C6B—N5B—C5B0.4 (3)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of rings C1A–C5A/N4A and C1B–C5B/N4B, respectively.
D—H···AD—HH···AD···AD—H···A
N3B—H3B···O4A0.861.912.774 (3)179
N5A—H5A···O1A0.862.062.592 (3)119
N5B—H5B···O1B0.862.082.604 (3)119
N2A—H10···O4A0.861.852.510 (3)132
N2B—H12···O4B0.861.862.515 (3)132
N3A—H3A···O4Bi0.861.962.823 (2)177
N5A—H5A···O3Bii0.862.423.131 (3)140
N5B—H5B···O3Aiii0.862.262.899 (3)131
C7A—H5···O3Aii0.972.583.302 (3)132
C7A—H6···O1Biv0.972.593.221 (3)123
C7A—H5···Cg1ii0.972.893.679 (3)139
C7B—H8···Cg2v0.972.853.747 (3)155
Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z; (iii) x+1, y+1, z; (iv) x, y1, z; (v) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of rings C1A–C5A/N4A and C1B–C5B/N4B, respectively.
D—H···AD—HH···AD···AD—H···A
N3B—H3B···O4A0.861.912.774 (3)179
N5A—H5A···O1A0.862.062.592 (3)119
N5B—H5B···O1B0.862.082.604 (3)119
N2A—H10···O4A0.861.852.510 (3)132
N2B—H12···O4B0.861.862.515 (3)132
N3A—H3A···O4Bi0.861.962.823 (2)177
N5A—H5A···O3Bii0.862.423.131 (3)140
N5B—H5B···O3Aiii0.862.262.899 (3)131
C7A—H5···O3Aii0.972.583.302 (3)132
C7A—H6···O1Biv0.972.593.221 (3)123
C7A—H5···Cg1ii0.972.893.679 (3)139
C7B—H8···Cg2v0.972.853.747 (3)155
Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z; (iii) x+1, y+1, z; (iv) x, y1, z; (v) x, y+1, z.
 

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