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The title compound, C22H19N3O2, is a Schiff base compound derived from 4-amino­anti­pyrine and 2-hydr­oxy-1-naphthaldehyde. As expected, the two crystallographically independent mol­ecules adopt trans configurations about the central C=N bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680601110X/ac2010sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680601110X/ac2010Isup2.hkl
Contains datablock I

CCDC reference: 604947

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.069
  • wR factor = 0.180
  • Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT024_ALERT_4_B Merging of Friedel Pairs is STRONGLY Indicated . !
Alert level C STRVA01_ALERT_4_C Flack test results are meaningless. From the CIF: _refine_ls_abs_structure_Flack 0.000 From the CIF: _refine_ls_abs_structure_Flack_su 2.000 PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 2.00 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C39 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 55.00 A   3 PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 2.00
Alert level G REFLT03_ALERT_4_G ALERT: MoKa measured Friedel data cannot be used to determine absolute structure in a light-atom study EXCEPT under VERY special conditions. It is preferred that Friedel data is merged in such cases. From the CIF: _diffrn_reflns_theta_max 26.50 From the CIF: _reflns_number_total 7941 Count of symmetry unique reflns 4081 Completeness (_total/calc) 194.58% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3860 Fraction of Friedel pairs measured 0.946 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 1 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

4-{[(2-Hydroxy-1-naphthyl)methylidene]amino}-1,5-dimethyl-2-phenyl- 1H-pyrazol-3(2H)-one top
Crystal data top
C22H19N3O2Dx = 1.239 Mg m3
Mr = 357.40Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21Cell parameters from 2824 reflections
a = 11.713 (1) Åθ = 2.3–24.9°
b = 14.951 (1) ŵ = 0.08 mm1
c = 21.877 (2) ÅT = 298 K
V = 3831.1 (5) Å3Block, yellow
Z = 80.30 × 0.17 × 0.10 mm
F(000) = 1504
Data collection top
Bruker SMART CCD area-detector
diffractometer
7941 independent reflections
Radiation source: fine-focus sealed tube4828 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
ω scansθmax = 26.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1414
Tmin = 0.976, Tmax = 0.992k = 1818
29274 measured reflectionsl = 2727
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.069H-atom parameters constrained
wR(F2) = 0.180 w = 1/[σ2(Fo2) + (0.0909P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
7941 reflectionsΔρmax = 0.32 e Å3
492 parametersΔρmin = 0.17 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0 (2)
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
O10.4986 (3)0.4407 (2)0.39088 (17)0.0716 (10)
H10.56230.44110.40650.107*
O20.8274 (3)0.24940 (15)0.52372 (16)0.0581 (10)
O30.7437 (3)0.0598 (2)0.17357 (17)0.0733 (10)
H30.79900.05820.15060.110*
O41.0713 (3)0.25090 (15)0.04195 (17)0.0623 (10)
N10.6663 (2)0.3787 (2)0.44958 (14)0.0484 (7)
N20.8834 (3)0.47425 (17)0.54214 (14)0.0522 (8)
N30.9123 (3)0.38358 (18)0.54892 (15)0.0529 (8)
N40.9098 (3)0.1211 (2)0.11165 (15)0.0507 (8)
N51.1240 (3)0.02692 (18)0.01714 (15)0.0537 (8)
N61.1531 (3)0.11739 (19)0.01070 (16)0.0555 (9)
C10.5324 (3)0.2843 (3)0.39861 (18)0.0432 (9)
C20.4672 (3)0.3559 (3)0.37953 (17)0.0522 (10)
C30.3658 (4)0.3422 (4)0.3478 (2)0.0626 (12)
H3A0.32200.39120.33610.075*
C40.3300 (4)0.2591 (3)0.3338 (2)0.0604 (14)
H40.26210.25200.31230.072*
C50.3925 (3)0.1827 (3)0.35072 (18)0.0510 (11)
C60.3585 (4)0.0967 (3)0.33524 (19)0.0653 (12)
H60.28970.08910.31470.078*
C70.4221 (4)0.0229 (3)0.3490 (2)0.0713 (13)
H70.39840.03390.33730.086*
C80.5239 (4)0.0355 (3)0.3812 (2)0.0724 (14)
H80.56790.01430.39110.087*
C90.5605 (3)0.1167 (3)0.3983 (2)0.0563 (10)
H90.62820.12170.42030.068*
C100.4974 (3)0.1959 (3)0.38331 (19)0.0490 (10)
C110.6342 (3)0.2981 (2)0.43532 (17)0.0447 (9)
H110.67640.24920.44870.054*
C120.7611 (3)0.3958 (2)0.48612 (16)0.0448 (9)
C130.7976 (3)0.4771 (3)0.50101 (19)0.0450 (10)
C140.7563 (4)0.5674 (3)0.4780 (2)0.0674 (12)
H14A0.81920.60850.47670.101*
H14B0.69850.59000.50500.101*
H14C0.72510.56070.43770.101*
C150.9715 (4)0.5396 (3)0.5513 (3)0.0743 (15)
H15A1.02190.53960.51670.111*
H15B1.01380.52510.58750.111*
H15C0.93760.59770.55570.111*
C160.8316 (3)0.3310 (2)0.51801 (18)0.0485 (9)
C170.9718 (3)0.3562 (2)0.60279 (19)0.0504 (9)
C180.9366 (4)0.3844 (3)0.6594 (2)0.0681 (12)
H180.87280.42100.66320.082*
C190.9954 (5)0.3585 (4)0.7103 (3)0.0945 (17)
H190.97310.37870.74870.113*
C201.0888 (6)0.3019 (4)0.7044 (3)0.102 (2)
H201.12630.28080.73900.123*
C211.1255 (5)0.2770 (4)0.6467 (4)0.100 (2)
H211.19140.24290.64250.120*
C221.0658 (4)0.3022 (3)0.5962 (2)0.0702 (13)
H221.08850.28300.55760.084*
C230.7772 (3)0.2179 (3)0.16267 (18)0.0461 (10)
C240.7135 (4)0.1471 (3)0.1838 (2)0.0579 (11)
C250.6123 (4)0.1616 (3)0.2169 (2)0.0643 (13)
H250.57080.11280.23100.077*
C260.5744 (4)0.2450 (3)0.2286 (2)0.0595 (15)
H260.50560.25250.24920.071*
C270.6374 (4)0.3218 (3)0.2100 (2)0.0545 (11)
C280.6025 (4)0.4086 (3)0.22507 (19)0.0630 (12)
H280.53600.41720.24750.076*
C290.6645 (4)0.4800 (3)0.2072 (2)0.0715 (13)
H290.64020.53760.21670.086*
C300.7643 (4)0.4671 (3)0.1749 (2)0.0623 (12)
H300.80700.51660.16300.075*
C310.8020 (4)0.3833 (3)0.1597 (2)0.0594 (11)
H310.86970.37690.13780.071*
C320.7408 (3)0.3079 (3)0.17648 (19)0.0448 (9)
C330.8790 (3)0.2011 (3)0.12645 (16)0.0469 (9)
H330.92310.24930.11360.056*
C341.0042 (3)0.1058 (2)0.07410 (17)0.0453 (9)
C351.0389 (3)0.0210 (3)0.05805 (19)0.0482 (10)
C360.9970 (4)0.0664 (3)0.0808 (2)0.0627 (12)
H36A1.00080.10980.04850.094*
H36B0.91930.06030.09420.094*
H36C1.04360.08570.11440.094*
C371.2108 (4)0.0400 (3)0.0045 (3)0.0666 (14)
H37A1.27410.03170.03170.100*
H37B1.23640.03390.03700.100*
H37C1.17920.09860.01030.100*
C381.0738 (3)0.1693 (2)0.04304 (18)0.0486 (9)
C391.2126 (3)0.1467 (2)0.04194 (18)0.0493 (9)
C401.1767 (4)0.1229 (3)0.0991 (2)0.0759 (13)
H401.11310.08650.10420.091*
C411.2375 (6)0.1542 (4)0.1496 (3)0.1062 (19)
H411.21580.13780.18890.127*
C421.3302 (6)0.2097 (4)0.1407 (3)0.111 (2)
H421.36960.23140.17450.133*
C431.3639 (6)0.2327 (4)0.0853 (4)0.102 (2)
H431.42550.27140.08050.122*
C441.3079 (4)0.1993 (3)0.0344 (2)0.0716 (13)
H441.33460.21230.00470.086*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.069 (2)0.0581 (19)0.087 (3)0.0147 (15)0.0120 (19)0.0064 (18)
O20.075 (2)0.0323 (19)0.067 (2)0.0052 (11)0.0225 (19)0.0010 (12)
O30.072 (2)0.063 (2)0.086 (3)0.0239 (16)0.0155 (18)0.0013 (18)
O40.080 (2)0.0324 (19)0.075 (3)0.0040 (12)0.021 (2)0.0039 (12)
N10.0505 (18)0.0481 (18)0.0467 (18)0.0005 (14)0.0020 (16)0.0024 (14)
N20.062 (2)0.0295 (17)0.065 (2)0.0007 (15)0.0068 (18)0.0054 (16)
N30.068 (2)0.0321 (16)0.059 (2)0.0025 (15)0.0155 (18)0.0008 (14)
N40.0487 (19)0.0477 (19)0.056 (2)0.0047 (15)0.0012 (17)0.0063 (15)
N50.064 (2)0.0345 (18)0.063 (2)0.0026 (16)0.0088 (18)0.0091 (16)
N60.064 (2)0.0346 (17)0.068 (2)0.0005 (15)0.0140 (19)0.0071 (15)
C10.042 (2)0.049 (2)0.039 (2)0.0014 (18)0.0046 (18)0.0028 (19)
C20.050 (2)0.062 (3)0.044 (2)0.007 (2)0.0034 (19)0.001 (2)
C30.043 (2)0.096 (4)0.049 (3)0.014 (2)0.000 (2)0.002 (3)
C40.044 (3)0.100 (4)0.038 (3)0.006 (2)0.004 (2)0.001 (2)
C50.042 (2)0.077 (3)0.033 (2)0.011 (2)0.0058 (19)0.007 (2)
C60.049 (2)0.096 (4)0.051 (3)0.018 (3)0.002 (2)0.012 (3)
C70.081 (3)0.070 (3)0.062 (3)0.022 (3)0.001 (3)0.018 (2)
C80.070 (3)0.058 (3)0.089 (4)0.002 (2)0.000 (3)0.008 (3)
C90.054 (2)0.055 (2)0.060 (2)0.0033 (19)0.013 (2)0.002 (2)
C100.040 (2)0.063 (3)0.044 (2)0.0003 (19)0.0040 (18)0.004 (2)
C110.0363 (19)0.046 (2)0.052 (2)0.0021 (16)0.0000 (17)0.0024 (17)
C120.049 (2)0.044 (2)0.042 (2)0.0039 (17)0.0014 (17)0.0065 (16)
C130.046 (2)0.040 (2)0.048 (2)0.0071 (17)0.0008 (19)0.0077 (18)
C140.077 (3)0.043 (2)0.082 (3)0.009 (2)0.003 (2)0.002 (2)
C150.078 (3)0.045 (3)0.100 (4)0.010 (2)0.017 (3)0.017 (3)
C160.051 (2)0.040 (2)0.054 (2)0.0052 (17)0.0019 (19)0.0020 (18)
C170.052 (2)0.040 (2)0.060 (3)0.0020 (17)0.008 (2)0.0024 (19)
C180.073 (3)0.067 (3)0.064 (3)0.002 (2)0.006 (3)0.008 (2)
C190.129 (5)0.097 (4)0.057 (3)0.001 (4)0.014 (3)0.007 (3)
C200.135 (5)0.079 (4)0.093 (4)0.001 (4)0.053 (4)0.018 (3)
C210.099 (5)0.074 (3)0.127 (6)0.016 (3)0.041 (4)0.004 (4)
C220.072 (3)0.056 (3)0.083 (3)0.013 (2)0.011 (3)0.011 (2)
C230.033 (2)0.068 (3)0.037 (2)0.008 (2)0.0051 (17)0.007 (2)
C240.049 (2)0.068 (3)0.057 (3)0.011 (2)0.006 (2)0.007 (2)
C250.054 (3)0.080 (3)0.059 (3)0.024 (2)0.001 (2)0.016 (3)
C260.030 (3)0.095 (4)0.053 (3)0.002 (2)0.001 (2)0.007 (2)
C270.044 (2)0.080 (3)0.040 (2)0.002 (2)0.000 (2)0.010 (2)
C280.053 (3)0.085 (3)0.050 (3)0.017 (2)0.003 (2)0.005 (2)
C290.075 (3)0.071 (3)0.069 (3)0.021 (3)0.009 (3)0.008 (3)
C300.073 (3)0.056 (3)0.058 (3)0.016 (2)0.007 (2)0.004 (2)
C310.054 (3)0.064 (3)0.060 (3)0.001 (2)0.006 (2)0.003 (2)
C320.042 (2)0.057 (2)0.035 (2)0.0032 (19)0.0047 (18)0.0028 (19)
C330.048 (2)0.051 (3)0.041 (2)0.0070 (18)0.0027 (17)0.0046 (17)
C340.050 (2)0.035 (2)0.051 (2)0.0013 (17)0.0034 (18)0.0015 (16)
C350.053 (2)0.042 (2)0.050 (3)0.0052 (18)0.010 (2)0.0118 (18)
C360.072 (3)0.040 (2)0.077 (3)0.0121 (19)0.010 (2)0.0049 (19)
C370.069 (3)0.040 (2)0.090 (4)0.008 (2)0.014 (3)0.002 (2)
C380.053 (2)0.037 (2)0.056 (2)0.0028 (17)0.0045 (19)0.0048 (18)
C390.054 (2)0.038 (2)0.055 (3)0.0039 (17)0.011 (2)0.0080 (18)
C400.077 (3)0.083 (3)0.068 (3)0.005 (2)0.005 (3)0.005 (3)
C410.155 (6)0.101 (4)0.063 (3)0.007 (4)0.008 (4)0.003 (3)
C420.149 (6)0.081 (4)0.102 (5)0.013 (4)0.065 (5)0.010 (4)
C430.112 (5)0.068 (3)0.126 (6)0.030 (3)0.058 (4)0.022 (4)
C440.076 (3)0.056 (3)0.083 (3)0.013 (2)0.015 (3)0.011 (2)
Geometric parameters (Å, º) top
O1—C21.343 (5)C17—C221.373 (6)
O1—H10.8200C18—C191.364 (7)
O2—C161.228 (4)C18—H180.9300
O3—C241.371 (5)C19—C201.389 (8)
O3—H30.8200C19—H190.9300
O4—C381.220 (4)C20—C211.383 (9)
N1—C111.300 (4)C20—H200.9300
N1—C121.392 (5)C21—C221.361 (8)
N2—C131.350 (5)C21—H210.9300
N2—N31.405 (4)C22—H220.9300
N2—C151.434 (5)C23—C241.375 (6)
N3—C161.403 (5)C23—C321.444 (6)
N3—C171.429 (5)C23—C331.453 (5)
N4—C331.290 (4)C24—C251.405 (6)
N4—C341.396 (5)C25—C261.348 (6)
N5—C351.343 (5)C25—H250.9300
N5—N61.402 (4)C26—C271.424 (6)
N5—C371.452 (5)C26—H260.9300
N6—C381.402 (5)C27—C281.400 (6)
N6—C391.416 (5)C27—C321.432 (6)
C1—C21.380 (5)C28—C291.349 (6)
C1—C101.423 (5)C28—H280.9300
C1—C111.452 (5)C29—C301.380 (6)
C2—C31.390 (6)C29—H290.9300
C3—C41.347 (6)C30—C311.369 (6)
C3—H3A0.9300C30—H300.9300
C4—C51.406 (6)C31—C321.386 (5)
C4—H40.9300C31—H310.9300
C5—C61.388 (6)C33—H330.9300
C5—C101.434 (6)C34—C351.378 (5)
C6—C71.365 (6)C34—C381.425 (5)
C6—H60.9300C35—C361.482 (5)
C7—C81.398 (6)C36—H36A0.9600
C7—H70.9300C36—H36B0.9600
C8—C91.341 (6)C36—H36C0.9600
C8—H80.9300C37—H37A0.9600
C9—C101.435 (5)C37—H37B0.9600
C9—H90.9300C37—H37C0.9600
C11—H110.9300C39—C401.366 (6)
C12—C131.329 (5)C39—C441.376 (6)
C12—C161.452 (5)C40—C411.396 (7)
C13—C141.519 (5)C40—H400.9300
C14—H14A0.9600C41—C421.380 (8)
C14—H14B0.9600C41—H410.9300
C14—H14C0.9600C42—C431.320 (9)
C15—H15A0.9600C42—H420.9300
C15—H15B0.9600C43—C441.387 (8)
C15—H15C0.9600C43—H430.9300
C17—C181.372 (6)C44—H440.9300
C2—O1—H1109.5C21—C20—H20120.3
C24—O3—H3109.5C19—C20—H20120.3
C11—N1—C12122.7 (3)C22—C21—C20120.5 (5)
C13—N2—N3106.3 (3)C22—C21—H21119.7
C13—N2—C15127.3 (4)C20—C21—H21119.7
N3—N2—C15118.0 (3)C21—C22—C17119.3 (5)
C16—N3—N2109.1 (3)C21—C22—H22120.4
C16—N3—C17124.5 (3)C17—C22—H22120.4
N2—N3—C17118.7 (3)C24—C23—C32119.1 (4)
C33—N4—C34121.4 (3)C24—C23—C33119.8 (4)
C35—N5—N6108.1 (3)C32—C23—C33121.2 (4)
C35—N5—C37126.9 (4)O3—C24—C23122.5 (4)
N6—N5—C37118.4 (3)O3—C24—C25116.7 (4)
N5—N6—C38108.9 (3)C23—C24—C25120.9 (4)
N5—N6—C39120.0 (3)C26—C25—C24121.2 (4)
C38—N6—C39124.4 (3)C26—C25—H25119.4
C2—C1—C10119.3 (4)C24—C25—H25119.4
C2—C1—C11120.8 (3)C25—C26—C27121.4 (4)
C10—C1—C11119.9 (4)C25—C26—H26119.3
O1—C2—C1121.6 (4)C27—C26—H26119.3
O1—C2—C3117.7 (4)C28—C27—C26122.0 (4)
C1—C2—C3120.6 (4)C28—C27—C32120.2 (4)
C4—C3—C2121.0 (5)C26—C27—C32117.8 (4)
C4—C3—H3A119.5C29—C28—C27120.5 (4)
C2—C3—H3A119.5C29—C28—H28119.7
C3—C4—C5121.8 (4)C27—C28—H28119.7
C3—C4—H4119.1C28—C29—C30119.6 (4)
C5—C4—H4119.1C28—C29—H29120.2
C6—C5—C4122.6 (4)C30—C29—H29120.2
C6—C5—C10119.6 (4)C31—C30—C29121.8 (5)
C4—C5—C10117.7 (4)C31—C30—H30119.1
C7—C6—C5122.6 (4)C29—C30—H30119.1
C7—C6—H6118.7C30—C31—C32120.9 (4)
C5—C6—H6118.7C30—C31—H31119.6
C6—C7—C8117.9 (4)C32—C31—H31119.6
C6—C7—H7121.0C31—C32—C27117.1 (4)
C8—C7—H7121.0C31—C32—C23123.4 (4)
C9—C8—C7122.3 (5)C27—C32—C23119.6 (4)
C9—C8—H8118.8N4—C33—C23121.8 (4)
C7—C8—H8118.8N4—C33—H33119.1
C8—C9—C10121.3 (4)C23—C33—H33119.1
C8—C9—H9119.4C35—C34—N4122.3 (3)
C10—C9—H9119.4C35—C34—C38108.8 (3)
C1—C10—C5119.4 (4)N4—C34—C38128.7 (3)
C1—C10—C9124.3 (4)N5—C35—C34109.2 (4)
C5—C10—C9116.2 (4)N5—C35—C36121.9 (4)
N1—C11—C1120.1 (3)C34—C35—C36128.9 (4)
N1—C11—H11119.9C35—C36—H36A109.5
C1—C11—H11119.9C35—C36—H36B109.5
C13—C12—N1124.5 (3)H36A—C36—H36B109.5
C13—C12—C16108.0 (3)C35—C36—H36C109.5
N1—C12—C16127.3 (3)H36A—C36—H36C109.5
C12—C13—N2111.9 (3)H36B—C36—H36C109.5
C12—C13—C14128.9 (4)N5—C37—H37A109.5
N2—C13—C14119.1 (4)N5—C37—H37B109.5
C13—C14—H14A109.5H37A—C37—H37B109.5
C13—C14—H14B109.5N5—C37—H37C109.5
H14A—C14—H14B109.5H37A—C37—H37C109.5
C13—C14—H14C109.5H37B—C37—H37C109.5
H14A—C14—H14C109.5O4—C38—N6124.0 (4)
H14B—C14—H14C109.5O4—C38—C34131.4 (4)
N2—C15—H15A109.5N6—C38—C34104.5 (3)
N2—C15—H15B109.5C40—C39—C44120.6 (4)
H15A—C15—H15B109.5C40—C39—N6120.8 (4)
N2—C15—H15C109.5C44—C39—N6118.6 (4)
H15A—C15—H15C109.5C39—C40—C41118.7 (5)
H15B—C15—H15C109.5C39—C40—H40120.6
O2—C16—N3122.3 (4)C41—C40—H40120.6
O2—C16—C12133.6 (4)C42—C41—C40119.5 (6)
N3—C16—C12104.0 (3)C42—C41—H41120.3
C18—C17—C22121.1 (4)C40—C41—H41120.3
C18—C17—N3120.7 (4)C43—C42—C41121.4 (5)
C22—C17—N3118.2 (4)C43—C42—H42119.3
C19—C18—C17119.8 (4)C41—C42—H42119.3
C19—C18—H18120.1C42—C43—C44120.2 (5)
C17—C18—H18120.1C42—C43—H43119.9
C18—C19—C20119.7 (5)C44—C43—H43119.9
C18—C19—H19120.1C39—C44—C43119.5 (5)
C20—C19—H19120.1C39—C44—H44120.2
C21—C20—C19119.5 (5)C43—C44—H44120.2
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···N40.821.822.541 (4)147
O1—H1···N10.821.802.523 (4)146
 

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