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The mol­ecular and crystal structures of (I), C20H19N3O2, and (II), C22H21N3O, are similar because they differ only in the substituent at the hydrazide N atom where a phenyl­methyl­ene moiety for (II) is present instead of a furan­methyl­ene moiety for (I).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989021001353/wm5599sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989021001353/wm5599Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989021001353/wm5599IIsup3.hkl
Contains datablock II

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989021001353/wm5599Isup4.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989021001353/wm5599IIsup5.cml
Supplementary material

CCDC references: 2061393; 2061392

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.002 Å
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.036
  • wR factor = 0.095
  • Data-to-parameter ratio = 11.1

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 39 Report
Alert level G PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT398_ALERT_2_G Deviating C-O-C Angle From 120 for O2 106.1 Degree PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 50 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 1 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 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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 PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 2.065 Check PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 24 Report
Alert level G PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 35 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ... 1 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 11 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 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 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
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

For both structures, data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

3-(2,3-Dimethylanilino)-N'-[(E)-(furan-2-yl)methylidene]benzohydrazide (I) top
Crystal data top
C20H19N3O2F(000) = 704
Mr = 333.38Dx = 1.302 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 13.8467 (3) ÅCell parameters from 9755 reflections
b = 15.8409 (3) Åθ = 3.3–74.5°
c = 8.0225 (2) ŵ = 0.69 mm1
β = 104.814 (1)°T = 150 K
V = 1701.20 (7) Å3Column, colourless
Z = 40.19 × 0.11 × 0.07 mm
Data collection top
Bruker D8 VENTURE PHOTON 100 CMOS
diffractometer
3372 independent reflections
Radiation source: INCOATEC IµS micro–focus source2939 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.031
Detector resolution: 10.4167 pixels mm-1θmax = 74.5°, θmin = 3.3°
ω scansh = 1416
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
k = 1819
Tmin = 0.88, Tmax = 0.95l = 99
13222 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036All H-atom parameters refined
wR(F2) = 0.095 w = 1/[σ2(Fo2) + (0.0475P)2 + 0.3981P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
3372 reflectionsΔρmax = 0.23 e Å3
303 parametersΔρmin = 0.19 e Å3
0 restraintsExtinction correction: SHELXL 2016/6 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0049 (4)
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.

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 > 2sigma(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
O10.43892 (6)0.33178 (5)0.45837 (10)0.0275 (2)
O20.10644 (7)0.20592 (6)0.31256 (12)0.0371 (2)
N10.62923 (8)0.38535 (8)0.58252 (15)0.0353 (3)
H10.5810 (13)0.3629 (11)0.495 (2)0.051 (5)*
N20.37222 (7)0.26862 (7)0.65665 (13)0.0262 (2)
H20.3836 (12)0.2485 (11)0.763 (2)0.043 (4)*
N30.29029 (7)0.24278 (6)0.52997 (12)0.0260 (2)
C10.70907 (9)0.42610 (8)0.53437 (15)0.0279 (3)
C20.76645 (9)0.37935 (8)0.44626 (15)0.0276 (3)
C30.84199 (9)0.42133 (9)0.39033 (15)0.0313 (3)
C40.85989 (10)0.50619 (9)0.42738 (17)0.0361 (3)
H40.9119 (12)0.5334 (11)0.389 (2)0.047 (5)*
C50.80281 (11)0.55168 (9)0.51433 (19)0.0378 (3)
H50.8130 (13)0.6122 (12)0.533 (2)0.052 (5)*
C60.72631 (10)0.51191 (9)0.56546 (18)0.0342 (3)
H60.6815 (13)0.5435 (11)0.618 (2)0.052 (5)*
C70.74397 (12)0.28753 (9)0.40596 (19)0.0381 (3)
H7A0.6963 (16)0.2816 (13)0.295 (3)0.073 (6)*
H7B0.8049 (17)0.2542 (14)0.398 (3)0.078 (6)*
H7C0.7169 (13)0.2599 (12)0.493 (2)0.055 (5)*
C80.90166 (13)0.37716 (12)0.2834 (2)0.0470 (4)
H8A0.8587 (14)0.3622 (12)0.170 (3)0.056 (5)*
H8B0.957 (2)0.4145 (17)0.265 (3)0.105 (8)*
H8C0.9298 (16)0.3242 (15)0.331 (3)0.075 (6)*
C90.60374 (9)0.39480 (8)0.73618 (15)0.0275 (3)
C100.66889 (10)0.43330 (8)0.88024 (16)0.0326 (3)
H100.7324 (13)0.4574 (11)0.866 (2)0.045 (4)*
C110.64394 (10)0.44053 (9)1.03499 (16)0.0350 (3)
H110.6916 (11)0.4702 (10)1.131 (2)0.037 (4)*
C120.55432 (10)0.40856 (9)1.05579 (16)0.0343 (3)
H120.5341 (11)0.4161 (10)1.165 (2)0.037 (4)*
C130.48990 (10)0.36959 (8)0.91722 (16)0.0293 (3)
H130.4250 (12)0.3490 (10)0.9272 (19)0.038 (4)*
C140.51281 (9)0.36090 (7)0.75761 (15)0.0251 (3)
C150.44003 (8)0.32000 (7)0.61193 (14)0.0238 (2)
C160.23183 (9)0.19224 (8)0.58218 (15)0.0280 (3)
H160.2460 (11)0.1729 (10)0.701 (2)0.038 (4)*
C170.13770 (9)0.16726 (8)0.46938 (16)0.0297 (3)
C180.06614 (11)0.11334 (10)0.4926 (2)0.0410 (3)
H180.0716 (14)0.0788 (12)0.597 (2)0.059 (5)*
C190.01455 (11)0.11896 (10)0.3418 (2)0.0440 (4)
H190.0782 (15)0.0886 (12)0.319 (2)0.061 (5)*
C200.01305 (10)0.17477 (10)0.2391 (2)0.0425 (4)
H200.0217 (15)0.1968 (13)0.124 (3)0.063 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0276 (4)0.0337 (5)0.0215 (4)0.0028 (3)0.0067 (3)0.0006 (3)
O20.0308 (5)0.0430 (5)0.0328 (5)0.0046 (4)0.0004 (4)0.0003 (4)
N10.0289 (6)0.0477 (7)0.0315 (6)0.0131 (5)0.0118 (4)0.0092 (5)
N20.0236 (5)0.0337 (5)0.0197 (5)0.0034 (4)0.0026 (4)0.0016 (4)
N30.0225 (5)0.0315 (5)0.0229 (5)0.0018 (4)0.0040 (4)0.0016 (4)
C10.0224 (6)0.0326 (6)0.0280 (6)0.0021 (5)0.0051 (4)0.0011 (5)
C20.0266 (6)0.0307 (6)0.0239 (6)0.0007 (5)0.0037 (4)0.0010 (5)
C30.0236 (6)0.0426 (7)0.0269 (6)0.0005 (5)0.0050 (5)0.0022 (5)
C40.0288 (7)0.0433 (8)0.0352 (7)0.0101 (6)0.0065 (5)0.0057 (6)
C50.0387 (8)0.0292 (7)0.0428 (8)0.0044 (5)0.0056 (6)0.0025 (6)
C60.0295 (7)0.0321 (7)0.0402 (7)0.0025 (5)0.0078 (5)0.0009 (5)
C70.0498 (9)0.0314 (7)0.0344 (7)0.0032 (6)0.0130 (6)0.0027 (5)
C80.0392 (9)0.0645 (11)0.0414 (9)0.0004 (7)0.0176 (7)0.0055 (7)
C90.0250 (6)0.0297 (6)0.0271 (6)0.0004 (5)0.0052 (4)0.0000 (5)
C100.0260 (6)0.0356 (7)0.0327 (7)0.0025 (5)0.0011 (5)0.0009 (5)
C110.0358 (7)0.0358 (7)0.0275 (6)0.0008 (5)0.0028 (5)0.0015 (5)
C120.0411 (7)0.0370 (7)0.0235 (6)0.0008 (6)0.0060 (5)0.0024 (5)
C130.0301 (7)0.0313 (6)0.0268 (6)0.0012 (5)0.0079 (5)0.0003 (5)
C140.0232 (6)0.0275 (6)0.0233 (6)0.0009 (4)0.0033 (4)0.0001 (4)
C150.0217 (6)0.0260 (6)0.0236 (6)0.0023 (4)0.0055 (4)0.0000 (4)
C160.0264 (6)0.0335 (6)0.0249 (6)0.0010 (5)0.0081 (5)0.0001 (5)
C170.0272 (6)0.0341 (6)0.0286 (6)0.0013 (5)0.0088 (5)0.0029 (5)
C180.0342 (7)0.0482 (8)0.0433 (8)0.0102 (6)0.0150 (6)0.0046 (6)
C190.0250 (7)0.0502 (9)0.0563 (9)0.0075 (6)0.0097 (6)0.0170 (7)
C200.0285 (7)0.0471 (8)0.0451 (8)0.0014 (6)0.0033 (6)0.0108 (7)
Geometric parameters (Å, º) top
O1—C151.2422 (14)C7—H7C0.978 (19)
O2—C171.3663 (16)C8—H8A0.98 (2)
O2—C201.3687 (16)C8—H8B1.01 (3)
N1—C91.3744 (16)C8—H8C0.96 (2)
N1—C11.4165 (16)C9—C101.4102 (17)
N1—H10.910 (19)C9—C141.4191 (17)
N2—C151.3582 (15)C10—C111.3759 (19)
N2—N31.3777 (13)C10—H100.993 (17)
N2—H20.883 (18)C11—C121.389 (2)
N3—C161.2826 (16)C11—H110.996 (16)
C1—C61.3915 (18)C12—C131.3804 (18)
C1—C21.4023 (17)C12—H120.989 (16)
C2—C31.4063 (17)C13—C141.4024 (17)
C2—C71.5053 (18)C13—H130.978 (16)
C3—C41.385 (2)C14—C151.4829 (15)
C3—C81.507 (2)C16—C171.4392 (17)
C4—C51.383 (2)C16—H160.973 (16)
C4—H40.955 (17)C17—C181.3566 (19)
C5—C61.3818 (19)C18—C191.424 (2)
C5—H50.975 (19)C18—H180.990 (19)
C6—H60.976 (18)C19—C201.330 (2)
C7—H7A0.97 (2)C19—H190.98 (2)
C7—H7B1.01 (2)C20—H200.99 (2)
C17—O2—C20106.08 (11)H8B—C8—H8C108.9 (19)
C9—N1—C1126.32 (11)N1—C9—C10121.67 (11)
C9—N1—H1115.6 (11)N1—C9—C14120.45 (11)
C1—N1—H1115.8 (11)C10—C9—C14117.77 (11)
C15—N2—N3118.53 (10)C11—C10—C9121.32 (12)
C15—N2—H2120.4 (11)C11—C10—H10120.6 (10)
N3—N2—H2120.9 (11)C9—C10—H10118.0 (10)
C16—N3—N2114.45 (10)C10—C11—C12121.07 (12)
C6—C1—C2120.85 (11)C10—C11—H11118.0 (9)
C6—C1—N1120.43 (11)C12—C11—H11120.9 (9)
C2—C1—N1118.62 (11)C13—C12—C11118.64 (12)
C1—C2—C3118.33 (11)C13—C12—H12119.6 (9)
C1—C2—C7120.39 (11)C11—C12—H12121.7 (9)
C3—C2—C7121.21 (12)C12—C13—C14121.92 (12)
C4—C3—C2119.82 (12)C12—C13—H13120.1 (9)
C4—C3—C8118.60 (13)C14—C13—H13118.0 (9)
C2—C3—C8121.53 (13)C13—C14—C9119.23 (11)
C5—C4—C3121.32 (12)C13—C14—C15119.71 (11)
C5—C4—H4120.2 (10)C9—C14—C15121.00 (10)
C3—C4—H4118.5 (10)O1—C15—N2121.19 (10)
C6—C5—C4119.50 (13)O1—C15—C14123.33 (10)
C6—C5—H5119.7 (10)N2—C15—C14115.47 (10)
C4—C5—H5120.7 (10)N3—C16—C17120.80 (11)
C5—C6—C1120.11 (13)N3—C16—H16122.0 (9)
C5—C6—H6121.1 (11)C17—C16—H16117.0 (9)
C1—C6—H6118.7 (11)C18—C17—O2109.77 (12)
C2—C7—H7A110.2 (13)C18—C17—C16131.50 (13)
C2—C7—H7B112.8 (13)O2—C17—C16118.59 (11)
H7A—C7—H7B106.1 (17)C17—C18—C19106.60 (14)
C2—C7—H7C112.1 (11)C17—C18—H18124.4 (11)
H7A—C7—H7C108.4 (16)C19—C18—H18129.0 (11)
H7B—C7—H7C106.9 (17)C20—C19—C18106.30 (13)
C3—C8—H8A110.5 (11)C20—C19—H19126.7 (11)
C3—C8—H8B111.0 (15)C18—C19—H19127.0 (11)
H8A—C8—H8B108.1 (18)C19—C20—O2111.25 (13)
C3—C8—H8C113.8 (13)C19—C20—H20131.6 (12)
H8A—C8—H8C104.2 (17)O2—C20—H20117.1 (12)
C15—N2—N3—C16177.81 (11)C11—C12—C13—C140.5 (2)
C9—N1—C1—C644.52 (19)C12—C13—C14—C91.49 (19)
C9—N1—C1—C2139.08 (13)C12—C13—C14—C15178.79 (12)
C6—C1—C2—C30.10 (18)N1—C9—C14—C13178.37 (11)
N1—C1—C2—C3176.49 (11)C10—C9—C14—C132.26 (17)
C6—C1—C2—C7177.09 (12)N1—C9—C14—C154.36 (18)
N1—C1—C2—C70.70 (18)C10—C9—C14—C15179.53 (11)
C1—C2—C3—C41.90 (18)N3—N2—C15—O112.62 (17)
C7—C2—C3—C4179.07 (12)N3—N2—C15—C14166.53 (10)
C1—C2—C3—C8175.36 (12)C13—C14—C15—O1157.42 (11)
C7—C2—C3—C81.81 (19)C9—C14—C15—O119.84 (18)
C2—C3—C4—C51.98 (19)C13—C14—C15—N221.70 (16)
C8—C3—C4—C5175.36 (13)C9—C14—C15—N2161.04 (11)
C3—C4—C5—C60.0 (2)N2—N3—C16—C17173.06 (11)
C4—C5—C6—C12.0 (2)C20—O2—C17—C180.28 (15)
C2—C1—C6—C52.09 (19)C20—O2—C17—C16175.78 (12)
N1—C1—C6—C5178.41 (12)N3—C16—C17—C18177.42 (14)
C1—N1—C9—C1014.2 (2)N3—C16—C17—O27.54 (18)
C1—N1—C9—C14169.88 (12)O2—C17—C18—C190.22 (16)
N1—C9—C10—C11178.26 (12)C16—C17—C18—C19175.15 (13)
C14—C9—C10—C112.20 (19)C17—C18—C19—C200.08 (17)
C9—C10—C11—C121.3 (2)C18—C19—C20—O20.10 (18)
C10—C11—C12—C130.4 (2)C17—O2—C20—C190.23 (16)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C17–C20/O2 and C1–C6 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.910 (19)1.977 (18)2.7045 (14)135.8 (15)
N2—H2···O1i0.883 (18)2.014 (18)2.8458 (13)156.4 (15)
C4—H4···Cg1ii0.955 (17)2.941 (17)3.7248 (15)140.1 (17)
C6—H6···O1iii0.976 (18)2.556 (18)3.3434 (16)137.7 (14)
C11—H11···Cg2iv0.996 (16)2.765 (16)3.6231 (14)144.8 (12)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y+1/2, z+1/2; (iii) x+1, y+1, z+1; (iv) x, y, z+1.
N'-[(E)-Benzylidene]-2-(2,3-dimethylanilino)-benzohydrazide (II) top
Crystal data top
C22H21N3OF(000) = 728
Mr = 343.42Dx = 1.256 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 14.3493 (8) ÅCell parameters from 9904 reflections
b = 15.7501 (9) Åθ = 4.3–74.6°
c = 8.3737 (5) ŵ = 0.62 mm1
β = 106.285 (2)°T = 150 K
V = 1816.55 (18) Å3Block, pale yellow
Z = 40.19 × 0.13 × 0.08 mm
Data collection top
Bruker D8 VENTURE PHOTON 100 CMOS
diffractometer
3665 independent reflections
Radiation source: INCOATEC IµS micro–focus source3140 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.031
Detector resolution: 10.4167 pixels mm-1θmax = 74.6°, θmin = 4.3°
ω scansh = 1716
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
k = 1918
Tmin = 0.86, Tmax = 0.95l = 109
13875 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037All H-atom parameters refined
wR(F2) = 0.092 w = 1/[σ2(Fo2) + (0.0409P)2 + 0.444P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
3665 reflectionsΔρmax = 0.17 e Å3
320 parametersΔρmin = 0.15 e Å3
0 restraintsExtinction correction: SHELXL 2016/6 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0033 (3)
Special details top

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

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 > 2sigma(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
O10.44514 (6)0.33126 (6)0.43024 (9)0.0300 (2)
N10.62636 (8)0.39413 (8)0.53993 (14)0.0392 (3)
H10.5771 (13)0.3712 (11)0.458 (2)0.051 (5)*
N20.39227 (7)0.26174 (7)0.62519 (12)0.0287 (2)
H20.4042 (11)0.2421 (10)0.732 (2)0.040 (4)*
N30.30815 (7)0.23802 (7)0.50842 (12)0.0278 (2)
C10.70441 (8)0.43293 (8)0.49433 (14)0.0301 (3)
C20.75817 (9)0.38475 (8)0.41121 (14)0.0301 (3)
C30.83421 (9)0.42441 (9)0.36395 (15)0.0330 (3)
C40.85496 (10)0.50931 (9)0.40197 (17)0.0386 (3)
H40.9098 (13)0.5351 (11)0.367 (2)0.052 (5)*
C50.80049 (11)0.55653 (9)0.48198 (18)0.0411 (3)
H50.8132 (13)0.6202 (12)0.504 (2)0.053 (5)*
C60.72458 (10)0.51889 (9)0.52686 (16)0.0365 (3)
H60.6833 (13)0.5527 (12)0.578 (2)0.054 (5)*
C70.73544 (13)0.29257 (9)0.3725 (2)0.0451 (4)
H7A0.7008 (18)0.2847 (16)0.256 (3)0.095 (7)*
H7B0.7995 (19)0.2567 (16)0.388 (3)0.096 (8)*
H7C0.6979 (15)0.2671 (13)0.443 (3)0.072 (6)*
C80.89350 (12)0.37677 (12)0.2713 (2)0.0490 (4)
H8A0.8504 (15)0.3577 (13)0.155 (3)0.068 (6)*
H8B0.9499 (16)0.4120 (13)0.259 (2)0.074 (6)*
H8C0.9197 (17)0.3238 (15)0.328 (3)0.083 (7)*
C90.60826 (8)0.39908 (8)0.69193 (14)0.0300 (3)
C100.67446 (9)0.43734 (9)0.83041 (16)0.0356 (3)
H100.7358 (12)0.4613 (10)0.8156 (19)0.045 (4)*
C110.65461 (10)0.44332 (9)0.98135 (16)0.0391 (3)
H110.7018 (12)0.4732 (10)1.073 (2)0.045 (4)*
C120.56938 (10)0.41042 (9)1.00387 (16)0.0386 (3)
H120.5526 (12)0.4186 (11)1.110 (2)0.053 (5)*
C130.50518 (9)0.36998 (8)0.87248 (15)0.0323 (3)
H130.4448 (11)0.3485 (10)0.8855 (18)0.037 (4)*
C140.52311 (8)0.36209 (8)0.71679 (14)0.0273 (3)
C150.45190 (8)0.31809 (8)0.57935 (14)0.0259 (2)
C160.25463 (8)0.18507 (8)0.55850 (14)0.0283 (3)
H160.2745 (11)0.1595 (10)0.6724 (19)0.039 (4)*
C170.15643 (8)0.16629 (8)0.45380 (14)0.0270 (2)
C180.11897 (9)0.20627 (8)0.30028 (15)0.0325 (3)
H180.1624 (12)0.2442 (11)0.258 (2)0.046 (4)*
C190.02375 (10)0.19387 (9)0.20915 (17)0.0387 (3)
H190.0003 (12)0.2241 (11)0.098 (2)0.051 (5)*
C200.03663 (9)0.14166 (9)0.26957 (17)0.0377 (3)
H200.1059 (13)0.1325 (11)0.205 (2)0.050 (4)*
C210.00080 (9)0.10191 (9)0.42071 (17)0.0373 (3)
H210.0449 (13)0.0660 (11)0.467 (2)0.051 (4)*
C220.09561 (9)0.11354 (9)0.51326 (16)0.0333 (3)
H220.1219 (11)0.0868 (10)0.6234 (19)0.038 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0270 (4)0.0408 (5)0.0213 (4)0.0033 (3)0.0051 (3)0.0017 (3)
N10.0290 (5)0.0598 (8)0.0297 (5)0.0158 (5)0.0096 (4)0.0104 (5)
N20.0229 (5)0.0392 (6)0.0212 (5)0.0030 (4)0.0019 (4)0.0015 (4)
N30.0219 (5)0.0362 (6)0.0235 (5)0.0016 (4)0.0034 (4)0.0018 (4)
C10.0235 (5)0.0390 (7)0.0261 (6)0.0033 (5)0.0041 (4)0.0003 (5)
C20.0309 (6)0.0328 (6)0.0253 (6)0.0003 (5)0.0053 (5)0.0017 (5)
C30.0282 (6)0.0424 (7)0.0281 (6)0.0030 (5)0.0076 (5)0.0056 (5)
C40.0333 (7)0.0454 (8)0.0364 (7)0.0080 (6)0.0085 (5)0.0067 (6)
C50.0463 (8)0.0333 (7)0.0417 (7)0.0066 (6)0.0092 (6)0.0012 (6)
C60.0354 (7)0.0362 (7)0.0368 (7)0.0037 (5)0.0083 (5)0.0027 (5)
C70.0632 (10)0.0346 (7)0.0402 (8)0.0068 (7)0.0189 (7)0.0025 (6)
C80.0463 (8)0.0616 (10)0.0453 (9)0.0114 (8)0.0229 (7)0.0053 (7)
C90.0248 (5)0.0366 (7)0.0263 (6)0.0003 (5)0.0034 (4)0.0009 (5)
C100.0292 (6)0.0416 (7)0.0306 (6)0.0046 (5)0.0005 (5)0.0013 (5)
C110.0416 (7)0.0412 (7)0.0268 (6)0.0047 (6)0.0030 (5)0.0025 (5)
C120.0467 (7)0.0436 (8)0.0234 (6)0.0018 (6)0.0065 (5)0.0032 (5)
C130.0336 (6)0.0367 (7)0.0260 (6)0.0004 (5)0.0074 (5)0.0008 (5)
C140.0246 (5)0.0329 (6)0.0226 (5)0.0012 (5)0.0037 (4)0.0007 (4)
C150.0205 (5)0.0326 (6)0.0237 (5)0.0029 (4)0.0050 (4)0.0003 (4)
C160.0260 (6)0.0352 (6)0.0236 (5)0.0009 (5)0.0066 (4)0.0004 (5)
C170.0251 (6)0.0307 (6)0.0252 (5)0.0008 (5)0.0070 (4)0.0030 (4)
C180.0300 (6)0.0369 (7)0.0292 (6)0.0000 (5)0.0057 (5)0.0012 (5)
C190.0330 (7)0.0451 (8)0.0326 (7)0.0035 (6)0.0001 (5)0.0003 (6)
C200.0244 (6)0.0447 (8)0.0402 (7)0.0007 (5)0.0028 (5)0.0106 (6)
C210.0298 (6)0.0425 (7)0.0411 (7)0.0077 (6)0.0123 (5)0.0075 (6)
C220.0306 (6)0.0381 (7)0.0306 (6)0.0049 (5)0.0076 (5)0.0009 (5)
Geometric parameters (Å, º) top
O1—C151.2424 (14)C9—C101.4115 (17)
N1—C91.3707 (16)C9—C141.4208 (17)
N1—C11.4189 (16)C10—C111.3745 (19)
N1—H10.908 (18)C10—H100.997 (16)
N2—C151.3607 (16)C11—C121.389 (2)
N2—N31.3750 (13)C11—H110.990 (16)
N2—H20.913 (16)C12—C131.3770 (18)
N3—C161.2814 (16)C12—H120.988 (17)
C1—C61.3954 (19)C13—C141.4033 (16)
C1—C21.3987 (17)C13—H130.965 (16)
C2—C31.4068 (17)C14—C151.4796 (15)
C2—C71.5034 (19)C16—C171.4659 (16)
C3—C41.387 (2)C16—H161.000 (15)
C3—C81.5030 (19)C17—C221.3941 (17)
C4—C51.381 (2)C17—C181.3966 (17)
C4—H41.001 (17)C18—C191.3793 (18)
C5—C61.382 (2)C18—H180.997 (17)
C5—H51.026 (18)C19—C201.389 (2)
C6—H60.980 (18)C19—H191.013 (18)
C7—H7A0.97 (3)C20—C211.376 (2)
C7—H7B1.06 (3)C20—H201.000 (18)
C7—H7C0.99 (2)C21—C221.3952 (18)
C8—H8A1.04 (2)C21—H211.004 (18)
C8—H8B1.01 (2)C22—H220.988 (15)
C8—H8C0.98 (2)
C9—N1—C1126.50 (11)C11—C10—C9121.30 (12)
C9—N1—H1114.2 (11)C11—C10—H10120.4 (9)
C1—N1—H1118.4 (11)C9—C10—H10118.3 (9)
C15—N2—N3118.21 (10)C10—C11—C12121.11 (12)
C15—N2—H2122.4 (10)C10—C11—H11118.3 (9)
N3—N2—H2119.3 (10)C12—C11—H11120.6 (9)
C16—N3—N2115.55 (10)C13—C12—C11118.77 (12)
C6—C1—C2120.68 (11)C13—C12—H12120.0 (10)
C6—C1—N1120.10 (12)C11—C12—H12121.2 (10)
C2—C1—N1119.17 (12)C12—C13—C14121.83 (12)
C1—C2—C3118.60 (12)C12—C13—H13119.5 (9)
C1—C2—C7120.96 (12)C14—C13—H13118.6 (9)
C3—C2—C7120.44 (12)C13—C14—C9119.28 (11)
C4—C3—C2119.79 (12)C13—C14—C15119.84 (11)
C4—C3—C8118.91 (13)C9—C14—C15120.85 (10)
C2—C3—C8121.30 (13)O1—C15—N2120.95 (10)
C5—C4—C3121.08 (12)O1—C15—C14123.08 (10)
C5—C4—H4121.5 (10)N2—C15—C14115.96 (10)
C3—C4—H4117.4 (10)N3—C16—C17119.96 (11)
C4—C5—C6119.84 (13)N3—C16—H16122.5 (9)
C4—C5—H5121.3 (9)C17—C16—H16117.3 (9)
C6—C5—H5118.8 (10)C22—C17—C18118.65 (11)
C5—C6—C1119.96 (12)C22—C17—C16119.98 (11)
C5—C6—H6120.4 (10)C18—C17—C16121.12 (11)
C1—C6—H6119.6 (10)C19—C18—C17120.75 (12)
C2—C7—H7A111.1 (15)C19—C18—H18120.5 (9)
C2—C7—H7B111.2 (13)C17—C18—H18118.7 (9)
H7A—C7—H7B103.8 (19)C18—C19—C20120.31 (12)
C2—C7—H7C112.7 (12)C18—C19—H19118.0 (10)
H7A—C7—H7C109.5 (19)C20—C19—H19121.7 (10)
H7B—C7—H7C108.2 (18)C21—C20—C19119.62 (12)
C3—C8—H8A110.6 (11)C21—C20—H20119.3 (10)
C3—C8—H8B111.4 (12)C19—C20—H20121.0 (10)
H8A—C8—H8B110.3 (15)C20—C21—C22120.51 (12)
C3—C8—H8C111.8 (13)C20—C21—H21119.9 (10)
H8A—C8—H8C104.6 (17)C22—C21—H21119.6 (10)
H8B—C8—H8C107.9 (18)C17—C22—C21120.16 (12)
N1—C9—C10121.87 (11)C17—C22—H22118.3 (9)
N1—C9—C14120.49 (10)C21—C22—H22121.5 (9)
C10—C9—C14117.58 (11)
C15—N2—N3—C16179.78 (11)C12—C13—C14—C92.03 (19)
C9—N1—C1—C649.49 (19)C12—C13—C14—C15179.98 (12)
C9—N1—C1—C2132.87 (14)N1—C9—C14—C13178.39 (12)
C6—C1—C2—C31.20 (17)C10—C9—C14—C134.26 (18)
N1—C1—C2—C3178.83 (11)N1—C9—C14—C150.46 (18)
C6—C1—C2—C7178.68 (12)C10—C9—C14—C15177.81 (11)
N1—C1—C2—C71.05 (18)N3—N2—C15—O118.17 (17)
C1—C2—C3—C40.75 (18)N3—N2—C15—C14161.30 (10)
C7—C2—C3—C4179.36 (12)C13—C14—C15—O1156.06 (12)
C1—C2—C3—C8178.75 (12)C9—C14—C15—O121.86 (18)
C7—C2—C3—C81.13 (19)C13—C14—C15—N223.40 (16)
C2—C3—C4—C51.70 (19)C9—C14—C15—N2158.68 (11)
C8—C3—C4—C5177.82 (13)N2—N3—C16—C17169.95 (10)
C3—C4—C5—C60.7 (2)N3—C16—C17—C22175.28 (12)
C4—C5—C6—C11.3 (2)N3—C16—C17—C181.04 (18)
C2—C1—C6—C52.25 (19)C22—C17—C18—C190.02 (19)
N1—C1—C6—C5179.86 (12)C16—C17—C18—C19174.33 (12)
C1—N1—C9—C107.4 (2)C17—C18—C19—C200.4 (2)
C1—N1—C9—C14175.32 (12)C18—C19—C20—C210.3 (2)
N1—C9—C10—C11178.76 (13)C19—C20—C21—C220.1 (2)
C14—C9—C10—C113.9 (2)C18—C17—C22—C210.45 (19)
C9—C10—C11—C121.2 (2)C16—C17—C22—C21173.93 (12)
C10—C11—C12—C131.2 (2)C20—C21—C22—C170.5 (2)
C11—C12—C13—C140.7 (2)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg3 are the centroids of the C1–C6 and C17–C22 benzene rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.908 (18)1.946 (18)2.6920 (13)138.2 (15)
N2—H2···O1i0.913 (16)1.974 (17)2.8564 (13)162.0 (14)
C4—H4···Cg3ii1.001 (17)2.796 (17)3.6141 (15)139.4 (13)
C6—H6···O1iii0.980 (18)2.583 (19)3.4815 (16)152.5 (13)
C20—H20···Cg1iv1.000 (18)2.838 (17)3.6644 (15)140.5 (13)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y+1/2, z+1/2; (iii) x+1, y+1, z+1; (iv) x1, y1/2, z3/2.
 

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