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In the title compound, C22H19N3O2, there are two independent mol­ecules in the asymmetric unit. Intra­molecular O—H...N hydrogen bonds are observed in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806044680/rz2070sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806044680/rz2070Isup2.hkl
Contains datablock I

CCDC reference: 630219

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.041
  • wR factor = 0.129
  • Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C24 - C25 .. 7.01 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C31 - C32 .. 7.35 su
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for N3 - C1 .. 5.25 su PLAT230_ALERT_2_C Hirshfeld Test Diff for N4 - N5 .. 6.78 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C34
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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.

5-(2-Hydroxyphenyl)-4-(4-methoxyphenyl)-3-(4-methylphenyl)-4H-1,2,4-triazole top
Crystal data top
C22H19N3O2Z = 4
Mr = 357.40F(000) = 752
Triclinic, P1Dx = 1.285 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.5954 (4) ÅCell parameters from 3025 reflections
b = 12.4637 (5) Åθ = 2.3–25.3°
c = 15.8750 (6) ŵ = 0.08 mm1
α = 90.9566 (6)°T = 298 K
β = 103.2093 (6)°Block, colourless
γ = 90.4278 (6)°0.18 × 0.16 × 0.11 mm
V = 1847.95 (13) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
8963 independent reflections
Radiation source: fine-focus sealed tube4446 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
φ and ω scansθmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.985, Tmax = 0.991k = 1616
22546 measured reflectionsl = 2021
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)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.129 w = 1/[σ2(Fo2) + (0.0672P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max = 0.019
8963 reflectionsΔρmax = 0.20 e Å3
500 parametersΔρmin = 0.12 e Å3
2 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997a), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0081 (12)
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
C10.24942 (14)1.01507 (11)0.49980 (9)0.0562 (3)
C20.10930 (14)0.87280 (11)0.47266 (9)0.0564 (4)
C30.02160 (14)0.78044 (11)0.43379 (9)0.0588 (4)
C40.01245 (17)0.70181 (13)0.48799 (10)0.0686 (4)
C50.09376 (19)0.61227 (13)0.45341 (13)0.0818 (5)
H50.11560.56050.49010.098*
C60.14188 (19)0.59956 (14)0.36592 (14)0.0857 (5)
H60.19360.53820.34330.103*
C70.11408 (18)0.67720 (14)0.31116 (12)0.0808 (5)
H70.14960.66960.25170.097*
C80.03340 (16)0.76601 (13)0.34493 (10)0.0701 (4)
H80.01490.81800.30750.084*
C90.34288 (14)1.10637 (11)0.49094 (9)0.0555 (3)
C100.42773 (16)1.10746 (12)0.43117 (10)0.0634 (4)
H100.42501.04920.39340.076*
C110.51598 (16)1.19357 (12)0.42689 (10)0.0680 (4)
H110.57141.19240.38590.082*
C120.52475 (15)1.28183 (12)0.48172 (10)0.0655 (4)
C130.44224 (17)1.27926 (13)0.54290 (10)0.0706 (4)
H130.44711.33680.58150.085*
C140.35334 (16)1.19362 (12)0.54785 (9)0.0650 (4)
H140.29961.19410.58980.078*
C150.61729 (18)1.37738 (13)0.47302 (12)0.0877 (5)
H15A0.70981.35330.46780.132*
H15B0.62771.42330.52330.132*
H15C0.57331.41640.42240.132*
C160.17266 (14)0.95902 (10)0.34289 (8)0.0527 (3)
C170.25054 (15)0.89442 (11)0.30036 (9)0.0591 (4)
H170.31030.84260.33050.071*
C180.24011 (15)0.90631 (11)0.21283 (9)0.0619 (4)
H180.29190.86190.18390.074*
C190.15301 (16)0.98390 (12)0.16841 (9)0.0613 (4)
C200.07391 (17)1.04825 (12)0.21219 (9)0.0705 (4)
H200.01381.10010.18230.085*
C210.08364 (16)1.03603 (11)0.29886 (9)0.0641 (4)
H210.03061.07940.32780.077*
C220.20854 (19)0.93831 (14)0.03339 (10)0.0820 (5)
H22A0.30920.94100.05950.123*
H22B0.19220.96470.02450.123*
H22C0.17440.86550.03180.123*
C230.29425 (19)0.53207 (14)0.88987 (11)0.0805 (5)
C240.46717 (19)0.51286 (12)0.82096 (11)0.0750 (5)
C250.57951 (19)0.52689 (13)0.77400 (10)0.0742 (5)
C260.6467 (2)0.43526 (15)0.74909 (12)0.0911 (6)
C270.7551 (3)0.4467 (2)0.70579 (13)0.1096 (7)
H270.79950.38580.69030.132*
C280.7983 (2)0.5443 (2)0.68527 (12)0.1006 (6)
H280.87150.55000.65590.121*
C290.7341 (2)0.63527 (16)0.70789 (12)0.0911 (5)
H290.76330.70250.69350.109*
C300.6272 (2)0.62657 (14)0.75155 (11)0.0820 (5)
H300.58500.68870.76680.098*
C310.18659 (19)0.58328 (13)0.92926 (11)0.0782 (5)
C320.1918 (2)0.57627 (16)1.01618 (13)0.0980 (6)
H320.26220.53491.05050.118*
C330.0949 (2)0.62928 (17)1.05370 (13)0.1009 (6)
H330.10220.62291.11280.121*
C340.0111 (2)0.69076 (15)1.00679 (14)0.0896 (5)
C350.0212 (2)0.69422 (17)0.91951 (14)0.1001 (6)
H350.09550.73220.88530.120*
C360.0754 (2)0.64311 (17)0.88078 (13)0.0962 (6)
H360.06620.64860.82140.115*
C370.1104 (2)0.75419 (17)1.04873 (16)0.1185 (7)
H37A0.13290.82061.01910.178*
H37B0.06480.76901.10820.178*
H37C0.19690.71361.04570.178*
C380.38954 (15)0.70377 (11)0.84731 (9)0.0579 (4)
C390.46871 (16)0.75577 (11)0.92031 (9)0.0638 (4)
H390.51640.71650.96730.077*
C400.47669 (16)0.86524 (11)0.92317 (9)0.0640 (4)
H400.52980.90050.97230.077*
C410.40582 (15)0.92418 (10)0.85303 (9)0.0554 (3)
C420.32699 (15)0.87201 (11)0.78019 (9)0.0601 (4)
H420.27990.91100.73290.072*
C430.31854 (15)0.76107 (11)0.77817 (9)0.0619 (4)
H430.26440.72530.72960.074*
C440.3460 (2)1.09826 (13)0.79523 (12)0.0996 (6)
H44A0.37991.08300.74400.149*
H44B0.36371.17250.81150.149*
H44C0.24501.08340.78410.149*
H10.074 (2)0.7768 (13)0.5875 (14)0.134 (9)*
H20.545 (2)0.3377 (19)0.8002 (15)0.146 (11)*
N10.22230 (13)0.98581 (10)0.57369 (7)0.0630 (3)
N20.13441 (13)0.89634 (10)0.55629 (7)0.0636 (3)
N30.18100 (12)0.94645 (9)0.43397 (7)0.0540 (3)
N40.3256 (2)0.42997 (12)0.89016 (12)0.1030 (5)
N50.4330 (2)0.41817 (12)0.84640 (12)0.0988 (5)
N60.37982 (14)0.58820 (9)0.84669 (8)0.0686 (3)
O10.02918 (15)0.70856 (11)0.57578 (8)0.0918 (4)
O20.13424 (13)1.00302 (9)0.08275 (6)0.0852 (3)
O30.6088 (2)0.33499 (12)0.76654 (12)0.1232 (5)
O40.41904 (12)1.03287 (8)0.86360 (6)0.0756 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0584 (8)0.0628 (9)0.0483 (8)0.0149 (7)0.0131 (6)0.0062 (7)
C20.0571 (8)0.0643 (9)0.0499 (8)0.0127 (7)0.0156 (7)0.0112 (7)
C30.0576 (8)0.0634 (9)0.0572 (9)0.0104 (7)0.0162 (7)0.0097 (7)
C40.0689 (10)0.0706 (10)0.0672 (11)0.0103 (8)0.0162 (8)0.0151 (8)
C50.0856 (12)0.0671 (11)0.0949 (14)0.0051 (9)0.0241 (10)0.0197 (9)
C60.0857 (12)0.0693 (11)0.1033 (15)0.0000 (9)0.0244 (11)0.0013 (10)
C70.0829 (11)0.0840 (12)0.0742 (11)0.0073 (10)0.0161 (9)0.0050 (9)
C80.0715 (10)0.0761 (11)0.0637 (10)0.0011 (8)0.0175 (8)0.0045 (8)
C90.0561 (8)0.0605 (9)0.0500 (8)0.0106 (7)0.0116 (6)0.0057 (7)
C100.0709 (10)0.0610 (9)0.0612 (9)0.0087 (8)0.0210 (8)0.0010 (7)
C110.0697 (10)0.0714 (10)0.0671 (10)0.0052 (8)0.0242 (8)0.0044 (8)
C120.0585 (9)0.0676 (10)0.0675 (10)0.0068 (7)0.0081 (7)0.0061 (8)
C130.0709 (10)0.0710 (10)0.0671 (10)0.0019 (8)0.0110 (8)0.0100 (8)
C140.0674 (9)0.0742 (10)0.0541 (9)0.0079 (8)0.0150 (7)0.0003 (7)
C150.0832 (12)0.0814 (12)0.0986 (14)0.0102 (10)0.0213 (10)0.0009 (10)
C160.0598 (8)0.0568 (8)0.0430 (7)0.0063 (7)0.0138 (6)0.0081 (6)
C170.0649 (9)0.0601 (9)0.0541 (9)0.0144 (7)0.0164 (7)0.0097 (6)
C180.0691 (9)0.0630 (9)0.0572 (9)0.0079 (7)0.0218 (7)0.0011 (7)
C190.0707 (9)0.0698 (9)0.0446 (8)0.0007 (8)0.0153 (7)0.0061 (7)
C200.0838 (11)0.0742 (10)0.0542 (9)0.0266 (8)0.0156 (8)0.0162 (7)
C210.0744 (10)0.0675 (9)0.0538 (9)0.0207 (7)0.0203 (7)0.0077 (7)
C220.0925 (12)0.1028 (13)0.0560 (9)0.0119 (10)0.0286 (9)0.0072 (9)
C230.0813 (12)0.0698 (12)0.0798 (12)0.0184 (10)0.0035 (9)0.0108 (9)
C240.0865 (12)0.0490 (9)0.0749 (11)0.0022 (9)0.0115 (9)0.0012 (8)
C250.0852 (12)0.0638 (10)0.0623 (10)0.0077 (9)0.0067 (9)0.0028 (8)
C260.1171 (16)0.0672 (12)0.0734 (12)0.0170 (11)0.0100 (11)0.0110 (9)
C270.133 (2)0.1104 (18)0.0781 (14)0.0440 (15)0.0080 (13)0.0147 (12)
C280.1072 (15)0.1196 (17)0.0692 (12)0.0331 (14)0.0075 (10)0.0028 (12)
C290.0855 (13)0.1013 (15)0.0843 (13)0.0118 (11)0.0139 (10)0.0046 (10)
C300.0852 (12)0.0713 (11)0.0842 (12)0.0123 (9)0.0081 (10)0.0012 (9)
C310.0758 (11)0.0784 (11)0.0712 (11)0.0267 (9)0.0027 (9)0.0169 (9)
C320.0965 (14)0.1036 (15)0.0817 (14)0.0090 (12)0.0062 (11)0.0215 (11)
C330.1054 (16)0.1171 (16)0.0737 (13)0.0190 (13)0.0069 (12)0.0160 (11)
C340.0783 (12)0.0928 (13)0.0945 (15)0.0293 (10)0.0125 (11)0.0207 (11)
C350.0744 (12)0.1236 (16)0.0971 (16)0.0086 (11)0.0065 (11)0.0392 (12)
C360.0820 (13)0.1240 (16)0.0771 (12)0.0110 (12)0.0052 (10)0.0278 (11)
C370.1041 (16)0.1251 (18)0.1351 (19)0.0251 (14)0.0452 (14)0.0176 (14)
C380.0642 (9)0.0509 (8)0.0539 (8)0.0059 (7)0.0038 (7)0.0025 (6)
C390.0754 (10)0.0597 (9)0.0494 (8)0.0019 (7)0.0002 (7)0.0080 (7)
C400.0775 (10)0.0603 (9)0.0474 (8)0.0047 (7)0.0008 (7)0.0019 (7)
C410.0641 (9)0.0504 (8)0.0512 (8)0.0009 (6)0.0123 (7)0.0005 (6)
C420.0688 (9)0.0591 (9)0.0489 (8)0.0059 (7)0.0055 (7)0.0062 (7)
C430.0715 (9)0.0602 (9)0.0481 (8)0.0035 (7)0.0019 (7)0.0026 (7)
C440.1221 (15)0.0607 (10)0.1027 (14)0.0085 (10)0.0034 (12)0.0199 (10)
N10.0691 (8)0.0720 (8)0.0492 (7)0.0060 (7)0.0157 (6)0.0066 (6)
N20.0679 (8)0.0733 (8)0.0513 (7)0.0052 (6)0.0166 (6)0.0075 (6)
N30.0592 (7)0.0593 (7)0.0443 (6)0.0072 (5)0.0131 (5)0.0062 (5)
N40.1086 (13)0.0628 (10)0.1271 (14)0.0195 (9)0.0046 (11)0.0183 (9)
N50.1062 (13)0.0609 (10)0.1202 (14)0.0076 (9)0.0067 (10)0.0078 (8)
N60.0785 (9)0.0548 (8)0.0646 (8)0.0099 (7)0.0000 (7)0.0047 (6)
O10.1101 (10)0.0946 (10)0.0698 (8)0.0079 (8)0.0174 (7)0.0251 (7)
O20.1053 (9)0.1071 (9)0.0466 (6)0.0216 (7)0.0233 (6)0.0119 (6)
O30.1670 (16)0.0674 (9)0.1274 (13)0.0193 (9)0.0181 (12)0.0135 (8)
O40.0964 (8)0.0530 (6)0.0697 (7)0.0030 (5)0.0031 (6)0.0009 (5)
Geometric parameters (Å, º) top
C1—N11.3150 (17)C23—C311.469 (3)
C1—N31.3794 (17)C24—N51.317 (2)
C1—C91.4720 (19)C24—N61.381 (2)
C2—N21.3216 (17)C24—C251.455 (2)
C2—N31.3770 (17)C25—C301.400 (2)
C2—C31.462 (2)C25—C261.410 (2)
C3—C81.397 (2)C26—O31.350 (2)
C3—C41.400 (2)C26—C271.379 (3)
C4—O11.3602 (18)C27—C281.351 (3)
C4—C51.388 (2)C27—H270.9300
C5—C61.366 (2)C28—C291.375 (3)
C5—H50.9300C28—H280.9300
C6—C71.376 (2)C29—C301.367 (2)
C6—H60.9300C29—H290.9300
C7—C81.375 (2)C30—H300.9300
C7—H70.9300C31—C321.374 (2)
C8—H80.9300C31—C361.394 (2)
C9—C101.3845 (19)C32—C331.380 (3)
C9—C141.3903 (19)C32—H320.9300
C10—C111.374 (2)C33—C341.364 (3)
C10—H100.9300C33—H330.9300
C11—C121.381 (2)C34—C351.368 (3)
C11—H110.9300C34—C371.503 (3)
C12—C131.387 (2)C35—C361.378 (3)
C12—C151.507 (2)C35—H350.9300
C13—C141.376 (2)C36—H360.9300
C13—H130.9300C37—H37A0.9600
C14—H140.9300C37—H37B0.9600
C15—H15A0.9600C37—H37C0.9600
C15—H15B0.9600C38—C431.3677 (18)
C15—H15C0.9600C38—C391.3803 (18)
C16—C171.3725 (18)C38—N61.4424 (17)
C16—C211.3788 (18)C39—C401.3653 (18)
C16—N31.4411 (16)C39—H390.9300
C17—C181.3808 (18)C40—C411.3895 (19)
C17—H170.9300C40—H400.9300
C18—C191.3771 (18)C41—O41.3637 (15)
C18—H180.9300C41—C421.3783 (19)
C19—O21.3558 (16)C42—C431.3840 (18)
C19—C201.391 (2)C42—H420.9300
C20—C211.3688 (19)C43—H430.9300
C20—H200.9300C44—O41.4227 (18)
C21—H210.9300C44—H44A0.9600
C22—O21.4197 (19)C44—H44B0.9600
C22—H22A0.9600C44—H44C0.9600
C22—H22B0.9600N1—N21.3784 (16)
C22—H22C0.9600N4—N51.376 (2)
C23—N41.310 (2)O1—H10.946 (15)
C23—N61.378 (2)O3—H20.902 (16)
N1—C1—N3110.07 (13)C30—C25—C24124.30 (15)
N1—C1—C9123.94 (13)C26—C25—C24118.92 (17)
N3—C1—C9125.97 (12)O3—C26—C27118.0 (2)
N2—C2—N3108.44 (12)O3—C26—C25122.1 (2)
N2—C2—C3122.49 (13)C27—C26—C25119.9 (2)
N3—C2—C3129.05 (12)C28—C27—C26121.6 (2)
C8—C3—C4117.13 (15)C28—C27—H27119.2
C8—C3—C2123.97 (13)C26—C27—H27119.2
C4—C3—C2118.89 (14)C27—C28—C29119.9 (2)
O1—C4—C5116.47 (15)C27—C28—H28120.0
O1—C4—C3122.98 (15)C29—C28—H28120.0
C5—C4—C3120.54 (16)C30—C29—C28119.8 (2)
C6—C5—C4120.49 (16)C30—C29—H29120.1
C6—C5—H5119.8C28—C29—H29120.1
C4—C5—H5119.8C29—C30—C25121.92 (17)
C5—C6—C7120.28 (17)C29—C30—H30119.0
C5—C6—H6119.9C25—C30—H30119.0
C7—C6—H6119.9C32—C31—C36116.5 (2)
C8—C7—C6119.53 (17)C32—C31—C23121.66 (17)
C8—C7—H7120.2C36—C31—C23121.81 (17)
C6—C7—H7120.2C31—C32—C33121.44 (19)
C7—C8—C3121.97 (15)C31—C32—H32119.3
C7—C8—H8119.0C33—C32—H32119.3
C3—C8—H8119.0C34—C33—C32122.1 (2)
C10—C9—C14117.76 (14)C34—C33—H33119.0
C10—C9—C1123.03 (13)C32—C33—H33119.0
C14—C9—C1119.12 (13)C33—C34—C35116.9 (2)
C11—C10—C9120.83 (14)C33—C34—C37121.9 (2)
C11—C10—H10119.6C35—C34—C37121.2 (2)
C9—C10—H10119.6C34—C35—C36122.02 (19)
C10—C11—C12121.92 (14)C34—C35—H35119.0
C10—C11—H11119.0C36—C35—H35119.0
C12—C11—H11119.0C35—C36—C31120.98 (18)
C11—C12—C13117.06 (15)C35—C36—H36119.5
C11—C12—C15120.86 (15)C31—C36—H36119.5
C13—C12—C15122.06 (15)C34—C37—H37A109.5
C14—C13—C12121.62 (15)C34—C37—H37B109.5
C14—C13—H13119.2H37A—C37—H37B109.5
C12—C13—H13119.2C34—C37—H37C109.5
C13—C14—C9120.77 (14)H37A—C37—H37C109.5
C13—C14—H14119.6H37B—C37—H37C109.5
C9—C14—H14119.6C43—C38—C39120.50 (13)
C12—C15—H15A109.5C43—C38—N6120.88 (12)
C12—C15—H15B109.5C39—C38—N6118.59 (12)
H15A—C15—H15B109.5C40—C39—C38119.64 (13)
C12—C15—H15C109.5C40—C39—H39120.2
H15A—C15—H15C109.5C38—C39—H39120.2
H15B—C15—H15C109.5C39—C40—C41120.31 (13)
C17—C16—C21120.52 (12)C39—C40—H40119.8
C17—C16—N3120.56 (11)C41—C40—H40119.8
C21—C16—N3118.92 (12)O4—C41—C42124.78 (12)
C16—C17—C18120.00 (12)O4—C41—C40115.30 (12)
C16—C17—H17120.0C42—C41—C40119.91 (13)
C18—C17—H17120.0C41—C42—C43119.36 (13)
C19—C18—C17120.01 (13)C41—C42—H42120.3
C19—C18—H18120.0C43—C42—H42120.3
C17—C18—H18120.0C38—C43—C42120.27 (13)
O2—C19—C18125.29 (13)C38—C43—H43119.9
O2—C19—C20115.33 (13)C42—C43—H43119.9
C18—C19—C20119.37 (13)O4—C44—H44A109.5
C21—C20—C19120.60 (13)O4—C44—H44B109.5
C21—C20—H20119.7H44A—C44—H44B109.5
C19—C20—H20119.7O4—C44—H44C109.5
C20—C21—C16119.50 (13)H44A—C44—H44C109.5
C20—C21—H21120.2H44B—C44—H44C109.5
C16—C21—H21120.2C1—N1—N2106.92 (12)
O2—C22—H22A109.5C2—N2—N1109.10 (11)
O2—C22—H22B109.5C2—N3—C1105.47 (11)
H22A—C22—H22B109.5C2—N3—C16127.81 (11)
O2—C22—H22C109.5C1—N3—C16126.28 (11)
H22A—C22—H22C109.5C23—N4—N5107.31 (15)
H22B—C22—H22C109.5C24—N5—N4109.20 (16)
N4—C23—N6109.71 (18)C23—N6—C24105.69 (14)
N4—C23—C31127.09 (18)C23—N6—C38123.51 (14)
N6—C23—C31123.20 (15)C24—N6—C38129.62 (14)
N5—C24—N6108.08 (18)C4—O1—H1104.7 (13)
N5—C24—C25122.23 (17)C19—O2—C22118.44 (12)
N6—C24—C25129.69 (14)C26—O3—H2110.0 (16)
C30—C25—C26116.78 (19)C41—O4—C44118.30 (12)
N2—C2—C3—C8165.26 (13)C36—C31—C32—C332.4 (3)
N3—C2—C3—C816.6 (2)C23—C31—C32—C33176.47 (17)
N2—C2—C3—C413.6 (2)C31—C32—C33—C340.3 (3)
N3—C2—C3—C4164.59 (13)C32—C33—C34—C352.6 (3)
C8—C3—C4—O1177.14 (13)C32—C33—C34—C37175.91 (18)
C2—C3—C4—O11.8 (2)C33—C34—C35—C363.4 (3)
C8—C3—C4—C52.0 (2)C37—C34—C35—C36175.08 (18)
C2—C3—C4—C5179.10 (13)C34—C35—C36—C311.4 (3)
O1—C4—C5—C6179.12 (15)C32—C31—C36—C351.6 (3)
C3—C4—C5—C60.0 (2)C23—C31—C36—C35177.30 (17)
C4—C5—C6—C72.1 (3)C43—C38—C39—C400.4 (2)
C5—C6—C7—C82.2 (3)N6—C38—C39—C40178.47 (14)
C6—C7—C8—C30.2 (2)C38—C39—C40—C410.1 (2)
C4—C3—C8—C71.9 (2)C39—C40—C41—O4178.84 (13)
C2—C3—C8—C7179.24 (14)C39—C40—C41—C420.0 (2)
N1—C1—C9—C10146.37 (14)O4—C41—C42—C43178.18 (13)
N3—C1—C9—C1031.8 (2)C40—C41—C42—C430.5 (2)
N1—C1—C9—C1430.0 (2)C39—C38—C43—C420.9 (2)
N3—C1—C9—C14151.76 (13)N6—C38—C43—C42178.98 (13)
C14—C9—C10—C111.9 (2)C41—C42—C43—C381.0 (2)
C1—C9—C10—C11178.33 (13)N3—C1—N1—N20.02 (14)
C9—C10—C11—C120.4 (2)C9—C1—N1—N2178.46 (11)
C10—C11—C12—C131.2 (2)N3—C2—N2—N10.23 (14)
C10—C11—C12—C15177.19 (13)C3—C2—N2—N1178.75 (11)
C11—C12—C13—C141.2 (2)C1—N1—N2—C20.13 (15)
C15—C12—C13—C14177.12 (14)N2—C2—N3—C10.23 (14)
C12—C13—C14—C90.3 (2)C3—C2—N3—C1178.62 (12)
C10—C9—C14—C131.8 (2)N2—C2—N3—C16172.88 (12)
C1—C9—C14—C13178.42 (12)C3—C2—N3—C168.7 (2)
C21—C16—C17—C180.0 (2)N1—C1—N3—C20.15 (14)
N3—C16—C17—C18179.13 (12)C9—C1—N3—C2178.56 (12)
C16—C17—C18—C190.8 (2)N1—C1—N3—C16172.95 (12)
C17—C18—C19—O2180.00 (13)C9—C1—N3—C168.6 (2)
C17—C18—C19—C201.3 (2)C17—C16—N3—C281.62 (17)
O2—C19—C20—C21179.76 (14)C21—C16—N3—C297.50 (17)
C18—C19—C20—C210.9 (2)C17—C16—N3—C1107.18 (16)
C19—C20—C21—C160.1 (2)C21—C16—N3—C173.70 (17)
C17—C16—C21—C200.4 (2)N6—C23—N4—N50.2 (2)
N3—C16—C21—C20179.51 (13)C31—C23—N4—N5179.59 (16)
N5—C24—C25—C30174.79 (15)N6—C24—N5—N41.08 (19)
N6—C24—C25—C305.3 (3)C25—C24—N5—N4179.00 (15)
N5—C24—C25—C264.9 (2)C23—N4—N5—C240.8 (2)
N6—C24—C25—C26174.97 (15)N4—C23—N6—C240.47 (18)
C30—C25—C26—O3179.43 (15)C31—C23—N6—C24178.98 (14)
C24—C25—C26—O30.8 (2)N4—C23—N6—C38169.13 (13)
C30—C25—C26—C270.8 (2)C31—C23—N6—C3810.3 (2)
C24—C25—C26—C27178.91 (16)N5—C24—N6—C230.95 (17)
O3—C26—C27—C28179.42 (17)C25—C24—N6—C23179.14 (16)
C25—C26—C27—C280.8 (3)N5—C24—N6—C38168.67 (13)
C26—C27—C28—C290.2 (3)C25—C24—N6—C3811.4 (3)
C27—C28—C29—C300.4 (3)C43—C38—N6—C23101.90 (17)
C28—C29—C30—C250.4 (3)C39—C38—N6—C2376.19 (19)
C26—C25—C30—C290.2 (2)C43—C38—N6—C2492.32 (19)
C24—C25—C30—C29179.49 (16)C39—C38—N6—C2489.59 (19)
N4—C23—C31—C3258.6 (2)C18—C19—O2—C220.5 (2)
N6—C23—C31—C32120.79 (18)C20—C19—O2—C22178.26 (14)
N4—C23—C31—C36122.6 (2)C42—C41—O4—C440.4 (2)
N6—C23—C31—C3658.0 (2)C40—C41—O4—C44178.31 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N20.95 (2)1.72 (2)2.5932 (18)153 (2)
O3—H2···N50.90 (2)1.75 (2)2.547 (3)147 (2)
 

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