In the title compound, C
16H
14N
2O
2, the two crystallographically independent molecules in the asymmetric unit have different orientations of the phenyl and methoxyphenyl substituents with respect to the pyrazole ring. Both independent molecules exist as O—H
N hydrogen-bonded dimers, which are interlinked
via C—H
N hydrogen bonds to form one-dimensional double-stranded chains. A three-dimensional network is formed
via C—H
π interactions.
Supporting information
CCDC reference: 221749
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.004 Å
- R factor = 0.053
- wR factor = 0.138
- Data-to-parameter ratio = 14.7
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing .. ?
Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5 .. CG1 .. 3.07 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5A .. CG2 .. 2.97 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8A .. CG3 .. 2.91 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10F .. CG2 .. 2.85 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15A .. CG4 .. 2.81 Ang.
1 ALERT level A = In general: serious problem
0 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
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
5 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: XSCANS (Bruker, 2000); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 2000); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
5-(4-Methoxyphenyl)-1-phenyl-3-hydroxy-1
H-pyrazole
top
Crystal data top
C16H14N2O2 | Z = 4 |
Mr = 266.29 | F(000) = 560 |
Triclinic, P1 | Dx = 1.308 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.4266 (19) Å | Cell parameters from 25 reflections |
b = 9.938 (2) Å | θ = 2.0–24.1° |
c = 15.347 (3) Å | µ = 0.09 mm−1 |
α = 88.90 (3)° | T = 291 K |
β = 86.63 (3)° | Block, white |
γ = 70.37 (3)° | 0.20 × 0.18 × 0.18 mm |
V = 1351.9 (5) Å3 | |
Data collection top
Bruker P4 diffractometer | 3789 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.012 |
Graphite monochromator | θmax = 26.0°, θmin = 1.3° |
2θ/ω scans | h = −11→11 |
Absorption correction: ψ scan (XPREP in SHELXTL; Bruker, 2000) | k = −12→12 |
Tmin = 0.97, Tmax = 0.98 | l = 0→18 |
5322 measured reflections | 3 standard reflections every 97 reflections |
5322 independent reflections | intensity decay: 0.01% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.138 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.06P)2 + 0.44P] where P = (Fo2 + 2Fc2)/3 |
5322 reflections | (Δ/σ)max < 0.001 |
361 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.1190 (2) | 0.29610 (18) | 0.49408 (11) | 0.0570 (4) | |
H1 | 0.0396 | 0.3520 | 0.5151 | 0.086* | |
O2 | 0.9594 (2) | 0.37515 (18) | 0.23268 (11) | 0.0576 (5) | |
N1 | 0.1547 (2) | 0.5107 (2) | 0.45785 (13) | 0.0542 (5) | |
N2 | 0.2785 (2) | 0.5424 (2) | 0.41793 (13) | 0.0532 (5) | |
C1 | 0.2037 (3) | 0.3675 (3) | 0.46163 (17) | 0.0546 (6) | |
C2 | 0.3453 (3) | 0.3038 (3) | 0.42142 (16) | 0.0549 (6) | |
H2 | 0.3988 | 0.2071 | 0.4137 | 0.066* | |
C3 | 0.3891 (3) | 0.4228 (3) | 0.39484 (17) | 0.0544 (6) | |
C4 | 0.5379 (3) | 0.4224 (3) | 0.35122 (17) | 0.0555 (6) | |
C5 | 0.6045 (3) | 0.5207 (3) | 0.36527 (17) | 0.0558 (6) | |
H5 | 0.5552 | 0.5976 | 0.4020 | 0.067* | |
C6 | 0.7446 (3) | 0.5096 (3) | 0.32615 (17) | 0.0564 (6) | |
H6 | 0.7868 | 0.5802 | 0.3346 | 0.068* | |
C7 | 0.8177 (3) | 0.3964 (3) | 0.27637 (17) | 0.0568 (6) | |
C8 | 0.7613 (3) | 0.2903 (3) | 0.26193 (17) | 0.0569 (6) | |
H8 | 0.8152 | 0.2124 | 0.2270 | 0.068* | |
C9 | 0.6175 (3) | 0.3015 (3) | 0.30180 (17) | 0.0566 (6) | |
H9 | 0.5772 | 0.2290 | 0.2950 | 0.068* | |
C10 | 1.0348 (3) | 0.4642 (3) | 0.25523 (18) | 0.0583 (6) | |
H10A | 0.9755 | 0.5612 | 0.2429 | 0.087* | |
H10B | 1.1298 | 0.4394 | 0.2222 | 0.087* | |
H10C | 1.0521 | 0.4544 | 0.3164 | 0.087* | |
C11 | 0.2482 (3) | 0.6880 (3) | 0.39407 (16) | 0.0493 (6) | |
C12 | 0.2499 (3) | 0.7253 (3) | 0.30674 (16) | 0.0526 (6) | |
H12 | 0.2730 | 0.6549 | 0.2640 | 0.063* | |
C13 | 0.2169 (3) | 0.8691 (3) | 0.28257 (18) | 0.0551 (6) | |
H13 | 0.2198 | 0.8949 | 0.2241 | 0.066* | |
C14 | 0.1807 (3) | 0.9688 (3) | 0.34594 (17) | 0.0558 (6) | |
H14 | 0.1569 | 1.0644 | 0.3302 | 0.067* | |
C15 | 0.1778 (3) | 0.9343 (3) | 0.43357 (17) | 0.0553 (6) | |
H15 | 0.1539 | 1.0052 | 0.4760 | 0.066* | |
C16 | 0.2110 (3) | 0.7924 (3) | 0.45693 (17) | 0.0532 (6) | |
H16 | 0.2080 | 0.7676 | 0.5156 | 0.064* | |
O1A | 0.9535 (2) | 0.94177 (18) | −0.10783 (11) | 0.0565 (4) | |
H1A | 1.0028 | 0.9820 | −0.0831 | 0.085* | |
O2A | 0.26504 (19) | 0.55211 (18) | 0.09247 (11) | 0.0564 (4) | |
N1A | 0.8693 (2) | 0.9293 (2) | 0.03676 (14) | 0.0542 (5) | |
N2A | 0.7633 (2) | 0.8763 (2) | 0.07750 (13) | 0.0538 (5) | |
C1A | 0.8623 (3) | 0.9031 (3) | −0.04811 (17) | 0.0548 (6) | |
C2A | 0.7638 (3) | 0.8341 (3) | −0.06357 (17) | 0.0548 (6) | |
H2A | 0.7465 | 0.8019 | −0.1171 | 0.066* | |
C3A | 0.6940 (3) | 0.8214 (3) | 0.01698 (17) | 0.0542 (6) | |
C4A | 0.5826 (3) | 0.7490 (3) | 0.03654 (17) | 0.0545 (6) | |
C5A | 0.4553 (3) | 0.7820 (3) | −0.01006 (17) | 0.0546 (6) | |
H5A | 0.4416 | 0.8502 | −0.0540 | 0.066* | |
C6A | 0.3467 (3) | 0.7181 (3) | 0.00557 (17) | 0.0553 (6) | |
H6A | 0.2620 | 0.7415 | −0.0274 | 0.066* | |
C7A | 0.3683 (3) | 0.6179 (3) | 0.07191 (17) | 0.0558 (6) | |
C8A | 0.4898 (3) | 0.5880 (3) | 0.12016 (17) | 0.0557 (6) | |
H8A | 0.5014 | 0.5214 | 0.1649 | 0.067* | |
C9A | 0.5965 (3) | 0.6520 (3) | 0.10583 (17) | 0.0551 (6) | |
H9A | 0.6775 | 0.6315 | 0.1416 | 0.066* | |
C10A | 0.1389 (3) | 0.5796 (3) | 0.03929 (17) | 0.0562 (6) | |
H10D | 0.0769 | 0.5254 | 0.0606 | 0.084* | |
H10E | 0.1741 | 0.5524 | −0.0199 | 0.084* | |
H10F | 0.0809 | 0.6796 | 0.0414 | 0.084* | |
C11A | 0.7359 (3) | 0.8895 (3) | 0.16712 (17) | 0.0545 (6) | |
C12A | 0.5876 (3) | 0.9299 (3) | 0.20412 (17) | 0.0548 (6) | |
H12A | 0.5061 | 0.9509 | 0.1688 | 0.066* | |
C13A | 0.5645 (3) | 0.9381 (3) | 0.29568 (17) | 0.0553 (6) | |
H13A | 0.4674 | 0.9622 | 0.3213 | 0.066* | |
C14A | 0.6868 (3) | 0.9101 (3) | 0.34766 (18) | 0.0554 (6) | |
H14A | 0.6714 | 0.9116 | 0.4081 | 0.066* | |
C15A | 0.8288 (3) | 0.8806 (3) | 0.31110 (17) | 0.0554 (6) | |
H15A | 0.9093 | 0.8687 | 0.3462 | 0.066* | |
C16A | 0.8531 (3) | 0.8683 (3) | 0.22081 (17) | 0.0548 (6) | |
H16A | 0.9509 | 0.8451 | 0.1963 | 0.066* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0572 (10) | 0.0553 (10) | 0.0577 (10) | −0.0179 (9) | −0.0015 (8) | 0.0003 (8) |
O2 | 0.0568 (11) | 0.0554 (11) | 0.0605 (11) | −0.0190 (9) | −0.0013 (9) | −0.0007 (8) |
N1 | 0.0558 (12) | 0.0517 (12) | 0.0550 (12) | −0.0183 (10) | −0.0015 (10) | 0.0019 (9) |
N2 | 0.0550 (12) | 0.0513 (12) | 0.0538 (12) | −0.0187 (10) | −0.0021 (10) | 0.0015 (9) |
C1 | 0.0558 (15) | 0.0526 (15) | 0.0552 (15) | −0.0179 (12) | −0.0020 (12) | 0.0015 (12) |
C2 | 0.0557 (15) | 0.0526 (14) | 0.0553 (15) | −0.0172 (12) | −0.0020 (12) | 0.0011 (12) |
C3 | 0.0556 (15) | 0.0522 (15) | 0.0552 (15) | −0.0179 (12) | −0.0025 (12) | 0.0007 (12) |
C4 | 0.0563 (15) | 0.0537 (15) | 0.0559 (15) | −0.0176 (12) | −0.0028 (12) | −0.0003 (12) |
C5 | 0.0564 (15) | 0.0544 (15) | 0.0564 (15) | −0.0181 (12) | −0.0033 (12) | −0.0009 (12) |
C6 | 0.0569 (15) | 0.0546 (15) | 0.0575 (15) | −0.0183 (12) | −0.0031 (12) | −0.0007 (12) |
C7 | 0.0568 (15) | 0.0545 (15) | 0.0590 (16) | −0.0185 (13) | −0.0021 (12) | 0.0003 (12) |
C8 | 0.0574 (16) | 0.0542 (15) | 0.0583 (15) | −0.0180 (13) | −0.0023 (12) | −0.0005 (12) |
C9 | 0.0571 (15) | 0.0541 (15) | 0.0577 (15) | −0.0175 (12) | −0.0025 (12) | −0.0007 (12) |
C10 | 0.0567 (15) | 0.0578 (16) | 0.0597 (16) | −0.0183 (13) | −0.0026 (12) | −0.0017 (12) |
C11 | 0.0522 (14) | 0.0492 (14) | 0.0498 (14) | −0.0214 (11) | −0.0027 (11) | 0.0017 (11) |
C12 | 0.0538 (14) | 0.0526 (15) | 0.0529 (14) | −0.0200 (12) | −0.0021 (11) | 0.0023 (11) |
C13 | 0.0549 (15) | 0.0549 (15) | 0.0560 (15) | −0.0192 (12) | −0.0029 (12) | 0.0023 (12) |
C14 | 0.0554 (15) | 0.0552 (15) | 0.0574 (15) | −0.0195 (12) | −0.0028 (12) | 0.0009 (12) |
C15 | 0.0554 (15) | 0.0548 (15) | 0.0563 (15) | −0.0193 (12) | −0.0025 (12) | −0.0006 (12) |
C16 | 0.0544 (15) | 0.0529 (15) | 0.0536 (14) | −0.0199 (12) | −0.0019 (11) | 0.0007 (11) |
O1A | 0.0598 (11) | 0.0566 (10) | 0.0530 (10) | −0.0193 (9) | −0.0031 (8) | −0.0033 (8) |
O2A | 0.0555 (10) | 0.0552 (10) | 0.0580 (10) | −0.0179 (8) | −0.0025 (8) | 0.0005 (8) |
N1A | 0.0559 (13) | 0.0528 (12) | 0.0531 (12) | −0.0173 (10) | −0.0017 (10) | 0.0013 (9) |
N2A | 0.0546 (12) | 0.0526 (12) | 0.0537 (12) | −0.0175 (10) | −0.0022 (10) | 0.0009 (10) |
C1A | 0.0568 (15) | 0.0540 (15) | 0.0534 (15) | −0.0183 (12) | −0.0025 (12) | 0.0003 (12) |
C2A | 0.0566 (15) | 0.0536 (15) | 0.0540 (14) | −0.0183 (12) | −0.0031 (12) | 0.0002 (11) |
C3A | 0.0554 (15) | 0.0528 (15) | 0.0543 (15) | −0.0179 (12) | −0.0028 (12) | 0.0007 (11) |
C4A | 0.0548 (15) | 0.0535 (15) | 0.0547 (15) | −0.0177 (12) | −0.0026 (12) | −0.0004 (12) |
C5A | 0.0544 (15) | 0.0538 (15) | 0.0551 (15) | −0.0174 (12) | −0.0032 (12) | 0.0000 (11) |
C6A | 0.0545 (15) | 0.0542 (15) | 0.0562 (15) | −0.0171 (12) | −0.0027 (12) | 0.0000 (12) |
C7A | 0.0550 (15) | 0.0547 (15) | 0.0568 (15) | −0.0174 (12) | −0.0025 (12) | −0.0001 (12) |
C8A | 0.0551 (15) | 0.0546 (15) | 0.0559 (15) | −0.0166 (12) | −0.0023 (12) | −0.0003 (12) |
C9A | 0.0548 (15) | 0.0541 (15) | 0.0554 (15) | −0.0169 (12) | −0.0021 (12) | −0.0014 (12) |
C10A | 0.0550 (15) | 0.0533 (15) | 0.0593 (15) | −0.0170 (12) | −0.0023 (12) | −0.0013 (12) |
C11A | 0.0549 (15) | 0.0537 (15) | 0.0541 (15) | −0.0173 (12) | −0.0014 (12) | −0.0001 (11) |
C12A | 0.0549 (15) | 0.0543 (15) | 0.0549 (15) | −0.0182 (12) | −0.0013 (12) | −0.0006 (12) |
C13A | 0.0551 (15) | 0.0548 (15) | 0.0557 (15) | −0.0186 (12) | −0.0005 (12) | −0.0013 (12) |
C14A | 0.0553 (15) | 0.0551 (15) | 0.0554 (15) | −0.0184 (12) | −0.0005 (12) | −0.0008 (12) |
C15A | 0.0554 (15) | 0.0549 (15) | 0.0550 (15) | −0.0178 (12) | −0.0005 (12) | −0.0010 (12) |
C16A | 0.0549 (15) | 0.0542 (15) | 0.0544 (15) | −0.0172 (12) | −0.0012 (12) | −0.0013 (11) |
Geometric parameters (Å, º) top
O1—C1 | 1.307 (3) | O1A—C1A | 1.358 (3) |
O1—H1 | 0.82 | O1A—H1A | 0.82 |
O2—C10 | 1.368 (3) | O2A—C7A | 1.363 (3) |
O2—C7 | 1.410 (3) | O2A—C10A | 1.429 (3) |
N1—C1 | 1.341 (3) | N1A—C1A | 1.343 (3) |
N1—N2 | 1.411 (3) | N1A—N2A | 1.391 (3) |
N2—C3 | 1.328 (3) | N2A—C3A | 1.385 (3) |
N2—C11 | 1.423 (3) | N2A—C11A | 1.385 (3) |
C1—C2 | 1.384 (4) | C1A—C2A | 1.360 (4) |
C2—C3 | 1.423 (3) | C2A—C3A | 1.389 (3) |
C2—H2 | 0.93 | C2A—H2A | 0.93 |
C3—C4 | 1.517 (4) | C3A—C4A | 1.474 (4) |
C4—C5 | 1.353 (4) | C4A—C5A | 1.374 (4) |
C4—C9 | 1.395 (4) | C4A—C9A | 1.403 (4) |
C5—C6 | 1.388 (4) | C5A—C6A | 1.383 (4) |
C5—H5 | 0.93 | C5A—H5A | 0.93 |
C6—C7 | 1.332 (4) | C6A—C7A | 1.385 (4) |
C6—H6 | 0.93 | C6A—H6A | 0.93 |
C7—C8 | 1.357 (4) | C7A—C8A | 1.346 (4) |
C8—C9 | 1.425 (4) | C8A—C9A | 1.365 (4) |
C8—H8 | 0.93 | C8A—H8A | 0.93 |
C9—H9 | 0.93 | C9A—H9A | 0.93 |
C10—H10A | 0.96 | C10A—H10D | 0.96 |
C10—H10B | 0.96 | C10A—H10E | 0.96 |
C10—H10C | 0.96 | C10A—H10F | 0.96 |
C11—C16 | 1.373 (3) | C11A—C16A | 1.374 (4) |
C11—C12 | 1.384 (3) | C11A—C12A | 1.406 (4) |
C12—C13 | 1.404 (4) | C12A—C13A | 1.409 (4) |
C12—H12 | 0.93 | C12A—H12A | 0.93 |
C13—C14 | 1.348 (4) | C13A—C14A | 1.388 (4) |
C13—H13 | 0.93 | C13A—H13A | 0.93 |
C14—C15 | 1.383 (4) | C14A—C15A | 1.359 (4) |
C14—H14 | 0.93 | C14A—H14A | 0.93 |
C15—C16 | 1.383 (4) | C15A—C16A | 1.392 (4) |
C15—H15 | 0.93 | C15A—H15A | 0.93 |
C16—H16 | 0.93 | C16A—H16A | 0.93 |
| | | |
C1—O1—H1 | 109.5 | C1A—O1A—H1A | 109.5 |
C10—O2—C7 | 116.6 (2) | C7A—O2A—C10A | 118.5 (2) |
C1—N1—N2 | 103.7 (2) | C1A—N1A—N2A | 103.3 (2) |
C3—N2—N1 | 110.4 (2) | C3A—N2A—C11A | 129.4 (2) |
C3—N2—C11 | 132.8 (2) | C3A—N2A—N1A | 111.0 (2) |
N1—N2—C11 | 115.0 (2) | C11A—N2A—N1A | 119.5 (2) |
O1—C1—N1 | 122.3 (2) | N1A—C1A—O1A | 119.1 (2) |
O1—C1—C2 | 123.6 (2) | N1A—C1A—C2A | 113.7 (2) |
N1—C1—C2 | 113.8 (2) | O1A—C1A—C2A | 127.1 (2) |
C1—C2—C3 | 102.9 (2) | C1A—C2A—C3A | 106.0 (2) |
C1—C2—H2 | 128.5 | C1A—C2A—H2A | 127.0 |
C3—C2—H2 | 128.5 | C3A—C2A—H2A | 127.0 |
N2—C3—C2 | 109.0 (2) | N2A—C3A—C2A | 105.8 (2) |
N2—C3—C4 | 122.7 (2) | N2A—C3A—C4A | 126.2 (2) |
C2—C3—C4 | 128.3 (2) | C2A—C3A—C4A | 127.6 (2) |
C5—C4—C9 | 118.9 (2) | C5A—C4A—C9A | 117.5 (2) |
C5—C4—C3 | 124.8 (2) | C5A—C4A—C3A | 120.2 (2) |
C9—C4—C3 | 115.8 (2) | C9A—C4A—C3A | 122.1 (2) |
C4—C5—C6 | 121.6 (3) | C4A—C5A—C6A | 122.8 (3) |
C4—C5—H5 | 119.2 | C4A—C5A—H5A | 118.6 |
C6—C5—H5 | 119.2 | C6A—C5A—H5A | 118.6 |
C7—C6—C5 | 119.1 (3) | C5A—C6A—C7A | 117.8 (3) |
C7—C6—H6 | 120.5 | C5A—C6A—H6A | 121.1 |
C5—C6—H6 | 120.5 | C7A—C6A—H6A | 121.1 |
C6—C7—C8 | 122.9 (3) | C8A—C7A—O2A | 118.4 (2) |
C6—C7—O2 | 123.8 (2) | C8A—C7A—C6A | 120.2 (3) |
C8—C7—O2 | 113.3 (2) | O2A—C7A—C6A | 121.3 (2) |
C7—C8—C9 | 118.2 (2) | C7A—C8A—C9A | 122.4 (3) |
C7—C8—H8 | 120.9 | C7A—C8A—H8A | 118.8 |
C9—C8—H8 | 120.9 | C9A—C8A—H8A | 118.8 |
C4—C9—C8 | 119.1 (2) | C8A—C9A—C4A | 119.2 (3) |
C4—C9—H9 | 120.4 | C8A—C9A—H9A | 120.4 |
C8—C9—H9 | 120.4 | C4A—C9A—H9A | 120.4 |
O2—C10—H10A | 109.5 | O2A—C10A—H10D | 109.5 |
O2—C10—H10B | 109.5 | O2A—C10A—H10E | 109.5 |
H10A—C10—H10B | 109.5 | H10D—C10A—H10E | 109.5 |
O2—C10—H10C | 109.5 | O2A—C10A—H10F | 109.5 |
H10A—C10—H10C | 109.5 | H10D—C10A—H10F | 109.5 |
H10B—C10—H10C | 109.5 | H10E—C10A—H10F | 109.5 |
C16—C11—C12 | 119.8 (2) | C16A—C11A—N2A | 120.4 (2) |
C16—C11—N2 | 120.4 (2) | C16A—C11A—C12A | 119.1 (2) |
C12—C11—N2 | 119.7 (2) | N2A—C11A—C12A | 120.5 (2) |
C11—C12—C13 | 120.1 (2) | C11A—C12A—C13A | 118.8 (2) |
C11—C12—H12 | 119.9 | C11A—C12A—H12A | 120.6 |
C13—C12—H12 | 119.9 | C13A—C12A—H12A | 120.6 |
C14—C13—C12 | 118.5 (2) | C14A—C13A—C12A | 120.0 (2) |
C14—C13—H13 | 120.7 | C14A—C13A—H13A | 120.0 |
C12—C13—H13 | 120.7 | C12A—C13A—H13A | 120.0 |
C13—C14—C15 | 122.4 (3) | C15A—C14A—C13A | 120.6 (3) |
C13—C14—H14 | 118.8 | C15A—C14A—H14A | 119.7 |
C15—C14—H14 | 118.8 | C13A—C14A—H14A | 119.7 |
C14—C15—C16 | 118.7 (2) | C14A—C15A—C16A | 119.6 (3) |
C14—C15—H15 | 120.6 | C14A—C15A—H15A | 120.2 |
C16—C15—H15 | 120.6 | C16A—C15A—H15A | 120.2 |
C11—C16—C15 | 120.4 (2) | C11A—C16A—C15A | 121.5 (2) |
C11—C16—H16 | 119.8 | C11A—C16A—H16A | 119.2 |
C15—C16—H16 | 119.8 | C15A—C16A—H16A | 119.2 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1i | 0.82 | 1.91 | 2.718 (3) | 169 |
O1A—H1A···N1Aii | 0.82 | 1.89 | 2.707 (3) | 174 |
C10—H10C···N1iii | 0.96 | 2.57 | 3.461 (4) | 154 |
C10A—H10F···N1Aiv | 0.96 | 2.61 | 3.551 (3) | 166 |
C5—H5···Cg1v | 0.93 | 3.07 | 3.495 (3) | 110 |
C5A—H5A···Cg2vi | 0.93 | 2.97 | 3.434 (3) | 113 |
C8A—H8A···Cg3 | 0.93 | 2.91 | 3.682 (3) | 142 |
C10—H10C···Cg1vii | 0.96 | 2.76 | 3.553 (3) | 141 |
C10A—H10F···Cg2iv | 0.96 | 2.85 | 3.646 (3) | 141 |
C15A—H15A···Cg4iii | 0.93 | 2.81 | 3.660 (3) | 152 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+2, −y+2, −z; (iii) x+1, y, z; (iv) x−1, y, z; (v) −x+1, −y+1, −z+1; (vi) −x+1, −y+2, −z; (vii) x+1, y+1, z. |