In the title compound, C
21H
26N
2O
2S, one of the pyrrolidine rings adopts a twist conformation, while the other is in an envelope conformation. Weak C—H
O interactions stabilize the crystal structure.
Supporting information
CCDC reference: 647151
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.045
- wR factor = 0.127
- Data-to-parameter ratio = 31.4
checkCIF/PLATON results
No syntax errors found
Alert level C
STRVA01_ALERT_4_C Flack test results are ambiguous.
From the CIF: _refine_ls_abs_structure_Flack 0.520
From the CIF: _refine_ls_abs_structure_Flack_su 0.060
PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 0.52
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.09
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.56 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.20 Ratio
Alert level G
ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be
replaced by the scaled T values. Since the ratio of scaled T's
is identical to the ratio of reported T values, the scaling
does not imply a change to the absorption corrections used in
the study.
Ratio of Tmax expected/reported 1.093
Tmax scaled 0.965 Tmin scaled 0.878
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 32.70
From the CIF: _reflns_number_total 7377
Count of symmetry unique reflns 4165
Completeness (_total/calc) 177.12%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 3212
Fraction of Friedel pairs measured 0.771
Are heavy atom types Z>Si present yes
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7 = . R
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
7 ALERT level G = General alerts; check
5 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
2 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).
1-Benzoyl-6-ethyl-5-(phenylsulfonyl)perhydropyrrolo[3,4-
b]pyrrole
top
Crystal data top
C21H26N2O2S | F(000) = 792 |
Mr = 370.50 | Dx = 1.224 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 39402 reflections |
a = 8.1022 (2) Å | θ = 2.1–32.7° |
b = 9.9925 (2) Å | µ = 0.18 mm−1 |
c = 24.8288 (5) Å | T = 293 K |
V = 2010.17 (8) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.20 × 0.20 mm |
Data collection top
Bruker Kappa-APEXII area-detector diffractometer | 7377 independent reflections |
Radiation source: fine-focus sealed tube | 5770 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
ω and φ scans | θmax = 32.7°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS: Sheldrick, 1996) | h = −11→12 |
Tmin = 0.803, Tmax = 0.883 | k = −15→10 |
39402 measured reflections | l = −37→28 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.0713P)2 + 0.1323P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
7377 reflections | Δρmax = 0.37 e Å−3 |
235 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Absolute structure: Flack (1983), with 3223 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.52 (6) |
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 | |
S1 | 0.60207 (5) | 0.53847 (4) | 0.239943 (13) | 0.04630 (10) | |
N1 | 0.68186 (15) | 0.64223 (12) | 0.07120 (4) | 0.0398 (2) | |
N2 | 0.57674 (15) | 0.65159 (12) | 0.19410 (4) | 0.0411 (2) | |
C6 | 0.47453 (18) | 0.62178 (16) | 0.14603 (5) | 0.0424 (3) | |
H6 | 0.4850 | 0.5271 | 0.1363 | 0.051* | |
C15 | 0.7386 (2) | 0.41615 (15) | 0.21463 (5) | 0.0442 (3) | |
O2 | 0.6826 (2) | 0.60255 (15) | 0.28424 (4) | 0.0679 (4) | |
C5 | 0.7138 (2) | 0.74275 (15) | 0.18131 (6) | 0.0458 (3) | |
H5A | 0.8140 | 0.6934 | 0.1733 | 0.055* | |
H5B | 0.7351 | 0.8039 | 0.2108 | 0.055* | |
C7 | 0.55312 (19) | 0.70939 (14) | 0.10248 (6) | 0.0416 (3) | |
H7 | 0.4693 | 0.7492 | 0.0790 | 0.050* | |
C9 | 0.75508 (19) | 0.47437 (14) | 0.00291 (5) | 0.0436 (3) | |
C8 | 0.61827 (19) | 0.55120 (17) | 0.03029 (6) | 0.0497 (3) | |
H8A | 0.5576 | 0.6020 | 0.0035 | 0.060* | |
H8B | 0.5423 | 0.4886 | 0.0469 | 0.060* | |
C4 | 0.6515 (2) | 0.81669 (14) | 0.13217 (6) | 0.0483 (3) | |
H4 | 0.5820 | 0.8930 | 0.1421 | 0.058* | |
C10 | 0.7620 (2) | 0.46460 (19) | −0.05280 (6) | 0.0563 (4) | |
H10 | 0.6836 | 0.5086 | −0.0737 | 0.068* | |
C16 | 0.6750 (3) | 0.30066 (17) | 0.19180 (7) | 0.0568 (4) | |
H16 | 0.5615 | 0.2878 | 0.1898 | 0.068* | |
O1 | 0.44579 (17) | 0.47526 (13) | 0.24773 (5) | 0.0657 (4) | |
C14 | 0.8746 (2) | 0.40921 (19) | 0.03273 (7) | 0.0591 (4) | |
H14 | 0.8722 | 0.4140 | 0.0701 | 0.071* | |
C2 | 0.7806 (2) | 0.75049 (17) | 0.04844 (7) | 0.0546 (4) | |
H2A | 0.7293 | 0.7856 | 0.0161 | 0.066* | |
H2B | 0.8906 | 0.7192 | 0.0395 | 0.066* | |
C20 | 0.9080 (2) | 0.43559 (18) | 0.21798 (7) | 0.0571 (4) | |
H20 | 0.9500 | 0.5129 | 0.2337 | 0.069* | |
C3 | 0.7879 (3) | 0.85758 (16) | 0.09232 (7) | 0.0625 (5) | |
H3A | 0.7664 | 0.9456 | 0.0775 | 0.075* | |
H3B | 0.8950 | 0.8582 | 0.1098 | 0.075* | |
C17 | 0.7819 (3) | 0.2049 (2) | 0.17213 (9) | 0.0730 (6) | |
H17 | 0.7403 | 0.1269 | 0.1569 | 0.088* | |
C11 | 0.8841 (3) | 0.3902 (2) | −0.07765 (7) | 0.0715 (6) | |
H11 | 0.8863 | 0.3833 | −0.1150 | 0.086* | |
C21 | 0.2932 (2) | 0.6567 (3) | 0.15614 (8) | 0.0721 (6) | |
H21A | 0.2585 | 0.6184 | 0.1902 | 0.086* | |
H21B | 0.2814 | 0.7531 | 0.1586 | 0.086* | |
C19 | 1.0130 (3) | 0.3399 (2) | 0.19801 (9) | 0.0700 (5) | |
H19 | 1.1266 | 0.3526 | 0.1999 | 0.084* | |
C12 | 1.0012 (3) | 0.3271 (2) | −0.04763 (10) | 0.0761 (6) | |
H12 | 1.0833 | 0.2773 | −0.0645 | 0.091* | |
C18 | 0.9500 (3) | 0.2243 (2) | 0.17500 (10) | 0.0749 (6) | |
H18 | 1.0214 | 0.1597 | 0.1615 | 0.090* | |
C13 | 0.9980 (3) | 0.3368 (2) | 0.00740 (10) | 0.0765 (6) | |
H13 | 1.0789 | 0.2946 | 0.0278 | 0.092* | |
C22 | 0.1843 (3) | 0.6047 (4) | 0.11195 (9) | 0.1066 (11) | |
H22A | 0.0718 | 0.6287 | 0.1193 | 0.160* | |
H22C | 0.1937 | 0.5090 | 0.1101 | 0.160* | |
H22B | 0.2177 | 0.6431 | 0.0782 | 0.160* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0541 (2) | 0.05103 (18) | 0.03378 (14) | 0.00048 (16) | 0.00773 (14) | 0.00629 (13) |
N1 | 0.0415 (6) | 0.0426 (5) | 0.0354 (5) | 0.0023 (5) | 0.0081 (4) | −0.0001 (4) |
N2 | 0.0445 (6) | 0.0435 (5) | 0.0354 (5) | −0.0004 (5) | 0.0073 (4) | 0.0040 (4) |
C6 | 0.0395 (6) | 0.0503 (7) | 0.0375 (6) | −0.0001 (6) | 0.0050 (5) | 0.0061 (5) |
C15 | 0.0490 (7) | 0.0459 (7) | 0.0378 (6) | 0.0016 (6) | −0.0004 (6) | 0.0077 (5) |
O2 | 0.0914 (10) | 0.0769 (8) | 0.0355 (5) | 0.0043 (8) | −0.0015 (6) | −0.0061 (6) |
C5 | 0.0505 (8) | 0.0426 (7) | 0.0442 (7) | −0.0051 (6) | 0.0081 (6) | −0.0044 (5) |
C7 | 0.0431 (7) | 0.0432 (6) | 0.0385 (6) | 0.0083 (5) | 0.0086 (5) | 0.0070 (5) |
C9 | 0.0496 (8) | 0.0435 (7) | 0.0376 (6) | 0.0005 (7) | 0.0009 (5) | −0.0037 (5) |
C8 | 0.0450 (7) | 0.0609 (9) | 0.0432 (7) | 0.0052 (7) | −0.0033 (6) | −0.0076 (6) |
C4 | 0.0626 (9) | 0.0337 (6) | 0.0486 (7) | 0.0038 (6) | 0.0173 (7) | 0.0014 (5) |
C10 | 0.0693 (10) | 0.0610 (9) | 0.0386 (6) | 0.0030 (9) | −0.0013 (7) | −0.0028 (7) |
C16 | 0.0639 (10) | 0.0485 (8) | 0.0580 (9) | −0.0034 (8) | −0.0045 (8) | 0.0009 (7) |
O1 | 0.0609 (7) | 0.0662 (7) | 0.0700 (8) | −0.0040 (6) | 0.0234 (6) | 0.0215 (7) |
C14 | 0.0675 (11) | 0.0655 (9) | 0.0442 (7) | 0.0177 (9) | −0.0028 (7) | −0.0027 (7) |
C2 | 0.0638 (10) | 0.0541 (8) | 0.0459 (8) | −0.0042 (7) | 0.0191 (7) | 0.0071 (6) |
C20 | 0.0533 (9) | 0.0590 (9) | 0.0590 (9) | 0.0004 (8) | −0.0083 (8) | 0.0065 (7) |
C3 | 0.0859 (13) | 0.0420 (7) | 0.0595 (9) | −0.0136 (8) | 0.0264 (9) | 0.0029 (7) |
C17 | 0.0952 (16) | 0.0508 (9) | 0.0729 (12) | 0.0095 (10) | −0.0062 (12) | −0.0066 (9) |
C11 | 0.0980 (16) | 0.0702 (11) | 0.0461 (8) | −0.0022 (12) | 0.0209 (10) | −0.0089 (8) |
C21 | 0.0436 (8) | 0.1165 (18) | 0.0560 (10) | 0.0094 (10) | 0.0112 (7) | 0.0177 (11) |
C19 | 0.0545 (10) | 0.0850 (14) | 0.0705 (12) | 0.0177 (10) | −0.0042 (9) | 0.0164 (11) |
C12 | 0.0854 (15) | 0.0693 (12) | 0.0738 (13) | 0.0170 (11) | 0.0263 (11) | −0.0108 (10) |
C18 | 0.0863 (14) | 0.0696 (12) | 0.0688 (12) | 0.0320 (11) | 0.0003 (11) | 0.0059 (10) |
C13 | 0.0772 (14) | 0.0757 (13) | 0.0765 (13) | 0.0323 (11) | −0.0008 (11) | −0.0011 (11) |
C22 | 0.0518 (11) | 0.197 (3) | 0.0704 (14) | −0.0146 (17) | −0.0061 (10) | 0.0233 (18) |
Geometric parameters (Å, º) top
S1—O1 | 1.4282 (14) | C16—C17 | 1.380 (3) |
S1—O2 | 1.4301 (13) | C16—H16 | 0.93 |
S1—N2 | 1.6172 (12) | C14—C13 | 1.385 (3) |
S1—C15 | 1.7645 (16) | C14—H14 | 0.93 |
N1—C8 | 1.4576 (18) | C2—C3 | 1.528 (2) |
N1—C2 | 1.4595 (19) | C2—H2A | 0.97 |
N1—C7 | 1.4634 (17) | C2—H2B | 0.97 |
N2—C5 | 1.4713 (19) | C20—C19 | 1.373 (3) |
N2—C6 | 1.4829 (19) | C20—H20 | 0.93 |
C6—C7 | 1.5299 (19) | C3—H3A | 0.97 |
C6—C21 | 1.531 (2) | C3—H3B | 0.97 |
C6—H6 | 0.98 | C17—C18 | 1.378 (4) |
C15—C16 | 1.385 (2) | C17—H17 | 0.93 |
C15—C20 | 1.389 (2) | C11—C12 | 1.361 (3) |
C5—C4 | 1.513 (2) | C11—H11 | 0.93 |
C5—H5A | 0.97 | C21—C22 | 1.501 (3) |
C5—H5B | 0.97 | C21—H21A | 0.97 |
C7—C4 | 1.526 (2) | C21—H21B | 0.97 |
C7—H7 | 0.98 | C19—C18 | 1.386 (3) |
C9—C14 | 1.382 (2) | C19—H19 | 0.93 |
C9—C10 | 1.3878 (19) | C12—C13 | 1.370 (3) |
C9—C8 | 1.510 (2) | C12—H12 | 0.93 |
C8—H8A | 0.97 | C18—H18 | 0.93 |
C8—H8B | 0.97 | C13—H13 | 0.93 |
C4—C3 | 1.538 (2) | C22—H22A | 0.96 |
C4—H4 | 0.98 | C22—H22C | 0.96 |
C10—C11 | 1.383 (3) | C22—H22B | 0.96 |
C10—H10 | 0.93 | | |
| | | |
O1—S1—O2 | 119.88 (9) | C17—C16—C15 | 119.28 (19) |
O1—S1—N2 | 106.97 (7) | C17—C16—H16 | 120.4 |
O2—S1—N2 | 106.64 (7) | C15—C16—H16 | 120.4 |
O1—S1—C15 | 107.33 (8) | C9—C14—C13 | 120.58 (16) |
O2—S1—C15 | 107.35 (8) | C9—C14—H14 | 119.7 |
N2—S1—C15 | 108.24 (6) | C13—C14—H14 | 119.7 |
C8—N1—C2 | 112.74 (12) | N1—C2—C3 | 105.31 (12) |
C8—N1—C7 | 113.83 (12) | N1—C2—H2A | 110.7 |
C2—N1—C7 | 104.86 (11) | C3—C2—H2A | 110.7 |
C5—N2—C6 | 111.86 (11) | N1—C2—H2B | 110.7 |
C5—N2—S1 | 119.26 (10) | C3—C2—H2B | 110.7 |
C6—N2—S1 | 119.80 (10) | H2A—C2—H2B | 108.8 |
N2—C6—C7 | 102.79 (11) | C19—C20—C15 | 119.58 (18) |
N2—C6—C21 | 110.99 (13) | C19—C20—H20 | 120.2 |
C7—C6—C21 | 112.65 (14) | C15—C20—H20 | 120.2 |
N2—C6—H6 | 110.1 | C2—C3—C4 | 104.18 (13) |
C7—C6—H6 | 110.1 | C2—C3—H3A | 110.9 |
C21—C6—H6 | 110.1 | C4—C3—H3A | 110.9 |
C16—C15—C20 | 120.59 (16) | C2—C3—H3B | 110.9 |
C16—C15—S1 | 119.31 (13) | C4—C3—H3B | 110.9 |
C20—C15—S1 | 120.10 (13) | H3A—C3—H3B | 108.9 |
N2—C5—C4 | 102.96 (13) | C18—C17—C16 | 120.3 (2) |
N2—C5—H5A | 111.2 | C18—C17—H17 | 119.9 |
C4—C5—H5A | 111.2 | C16—C17—H17 | 119.9 |
N2—C5—H5B | 111.2 | C12—C11—C10 | 120.21 (17) |
C4—C5—H5B | 111.2 | C12—C11—H11 | 119.9 |
H5A—C5—H5B | 109.1 | C10—C11—H11 | 119.9 |
N1—C7—C4 | 101.90 (12) | C22—C21—C6 | 111.44 (19) |
N1—C7—C6 | 114.16 (11) | C22—C21—H21A | 109.3 |
C4—C7—C6 | 106.15 (12) | C6—C21—H21A | 109.3 |
N1—C7—H7 | 111.4 | C22—C21—H21B | 109.3 |
C4—C7—H7 | 111.4 | C6—C21—H21B | 109.3 |
C6—C7—H7 | 111.4 | H21A—C21—H21B | 108.0 |
C14—C9—C10 | 118.19 (15) | C20—C19—C18 | 120.1 (2) |
C14—C9—C8 | 120.85 (13) | C20—C19—H19 | 120.0 |
C10—C9—C8 | 120.95 (14) | C18—C19—H19 | 120.0 |
N1—C8—C9 | 111.81 (12) | C11—C12—C13 | 120.01 (19) |
N1—C8—H8A | 109.3 | C11—C12—H12 | 120.0 |
C9—C8—H8A | 109.3 | C13—C12—H12 | 120.0 |
N1—C8—H8B | 109.3 | C17—C18—C19 | 120.2 (2) |
C9—C8—H8B | 109.3 | C17—C18—H18 | 119.9 |
H8A—C8—H8B | 107.9 | C19—C18—H18 | 119.9 |
C5—C4—C7 | 102.76 (11) | C12—C13—C14 | 120.2 (2) |
C5—C4—C3 | 114.12 (15) | C12—C13—H13 | 119.9 |
C7—C4—C3 | 104.54 (12) | C14—C13—H13 | 119.9 |
C5—C4—H4 | 111.6 | C21—C22—H22A | 109.5 |
C7—C4—H4 | 111.6 | C21—C22—H22C | 109.5 |
C3—C4—H4 | 111.6 | H22A—C22—H22C | 109.5 |
C11—C10—C9 | 120.77 (17) | C21—C22—H22B | 109.5 |
C11—C10—H10 | 119.6 | H22A—C22—H22B | 109.5 |
C9—C10—H10 | 119.6 | H22C—C22—H22B | 109.5 |
| | | |
O1—S1—N2—C5 | 173.97 (11) | N2—C5—C4—C7 | −35.39 (14) |
O2—S1—N2—C5 | 44.57 (13) | N2—C5—C4—C3 | −147.94 (12) |
C15—S1—N2—C5 | −70.66 (12) | N1—C7—C4—C5 | −85.23 (12) |
O1—S1—N2—C6 | −41.66 (12) | C6—C7—C4—C5 | 34.54 (15) |
O2—S1—N2—C6 | −171.07 (11) | N1—C7—C4—C3 | 34.21 (15) |
C15—S1—N2—C6 | 73.71 (12) | C6—C7—C4—C3 | 153.98 (13) |
C5—N2—C6—C7 | −3.42 (15) | C14—C9—C10—C11 | 0.8 (3) |
S1—N2—C6—C7 | −150.22 (10) | C8—C9—C10—C11 | −177.68 (17) |
C5—N2—C6—C21 | −124.09 (16) | C20—C15—C16—C17 | −0.3 (3) |
S1—N2—C6—C21 | 89.12 (16) | S1—C15—C16—C17 | −179.84 (15) |
O1—S1—C15—C16 | 18.63 (14) | C10—C9—C14—C13 | 0.3 (3) |
O2—S1—C15—C16 | 148.74 (13) | C8—C9—C14—C13 | 178.77 (19) |
N2—S1—C15—C16 | −96.50 (13) | C8—N1—C2—C3 | 161.85 (14) |
O1—S1—C15—C20 | −160.95 (13) | C7—N1—C2—C3 | 37.48 (18) |
O2—S1—C15—C20 | −30.84 (15) | C16—C15—C20—C19 | 0.6 (3) |
N2—S1—C15—C20 | 83.92 (14) | S1—C15—C20—C19 | −179.81 (14) |
C6—N2—C5—C4 | 24.83 (15) | N1—C2—C3—C4 | −14.73 (19) |
S1—N2—C5—C4 | 171.83 (9) | C5—C4—C3—C2 | 99.48 (17) |
C8—N1—C7—C4 | −168.30 (12) | C7—C4—C3—C2 | −12.00 (18) |
C2—N1—C7—C4 | −44.63 (14) | C15—C16—C17—C18 | −0.3 (3) |
C8—N1—C7—C6 | 77.75 (16) | C9—C10—C11—C12 | −1.1 (3) |
C2—N1—C7—C6 | −158.58 (13) | N2—C6—C21—C22 | −169.8 (2) |
N2—C6—C7—N1 | 91.97 (14) | C7—C6—C21—C22 | 75.5 (3) |
C21—C6—C7—N1 | −148.51 (16) | C15—C20—C19—C18 | −0.4 (3) |
N2—C6—C7—C4 | −19.45 (14) | C10—C11—C12—C13 | 0.2 (4) |
C21—C6—C7—C4 | 100.08 (16) | C16—C17—C18—C19 | 0.4 (4) |
C2—N1—C8—C9 | 66.34 (17) | C20—C19—C18—C17 | −0.1 (3) |
C7—N1—C8—C9 | −174.38 (12) | C11—C12—C13—C14 | 0.9 (4) |
C14—C9—C8—N1 | 49.5 (2) | C9—C14—C13—C12 | −1.1 (4) |
C10—C9—C8—N1 | −132.03 (16) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5B···O1i | 0.97 | 2.48 | 3.190 (2) | 130 |
C11—H11···O2ii | 0.93 | 2.57 | 3.472 (2) | 164 |
C21—H21A···O1 | 0.97 | 2.53 | 3.160 (3) | 123 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+3/2, −y+1, z−1/2. |