The structure of the title compound, 2-methyl-1-(1,2,3,9-tetrahydro-9-methyl-4-oxo-4H-carbazol-3-ylmethyl)-1H-imidazol-3-ium chloride dihydrate, C18H24N3+·Cl-·2H2O, has been reported previously by Collin, Moureau, Quintero, Vercauteren, Evrard & Durant [(1995). J. Chem. Soc. Perkin Trans. 2, pp. 77-84] and Chandra Mohan & Ravikumar, [(1995), Acta Cryst. C51, 2627-2629]. In both determinations, all atoms were refined as clearly ordered. In contrast to this, we present here a redetermination of this structure from new intensity data where two atoms of the cyclohexenone ring are disordered over two sites. Apart from this disorder, our results agree with the already published data.
Supporting information
CCDC reference: 262440
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.002 Å
- R factor = 0.033
- wR factor = 0.087
- Data-to-parameter ratio = 15.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT301_ALERT_3_C Main Residue Disorder ......................... 8.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 6
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3
H2 O
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 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
1 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 1990).
2-methyl-1-(1,2,3,9-tetrahydro-9-methyl-4-oxo-4
H-carbazol-3-ylmethyl)-1
H- imidazol-3-ium chloride dihydrate
top
Crystal data top
C18H20N3O+·Cl−·2H2O | F(000) = 776 |
Mr = 365.85 | Dx = 1.349 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 20705 reflections |
a = 15.0216 (13) Å | θ = 3.7–27.6° |
b = 9.6464 (8) Å | µ = 0.23 mm−1 |
c = 12.6545 (10) Å | T = 173 K |
β = 100.708 (6)° | Plate, colourless |
V = 1801.8 (3) Å3 | 0.33 × 0.27 × 0.14 mm |
Z = 4 | |
Data collection top
Stoe IPDS-II two-circle diffractometer | 4181 independent reflections |
Radiation source: fine-focus sealed tube | 3172 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
ω scans | θmax = 27.7°, θmin = 3.9° |
Absorption correction: multi-scan (MULABS; Spek, 1990; Blessing, 1995) | h = −19→19 |
Tmin = 0.928, Tmax = 0.967 | k = −12→12 |
24157 measured reflections | l = −16→16 |
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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.087 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | w = 1/[σ2(Fo2) + (0.0567P)2] where P = (Fo2 + 2Fc2)/3 |
4181 reflections | (Δ/σ)max < 0.001 |
267 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.21 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 | Occ. (<1) |
Cl1 | 0.08662 (2) | 0.57279 (4) | 0.19007 (3) | 0.03587 (10) | |
C1 | 0.37820 (9) | 0.65753 (13) | 0.86936 (11) | 0.0294 (3) | |
O1 | 0.33929 (7) | 0.74929 (12) | 0.91009 (10) | 0.0455 (3) | |
C2 | 0.32432 (15) | 0.5479 (2) | 0.7974 (2) | 0.0245 (5) | 0.791 (6) |
H2 | 0.3175 | 0.4661 | 0.8438 | 0.029* | 0.791 (6) |
C3 | 0.37766 (11) | 0.4994 (2) | 0.71167 (15) | 0.0279 (5) | 0.791 (6) |
H3A | 0.3873 | 0.5792 | 0.6658 | 0.034* | 0.791 (6) |
H3B | 0.3417 | 0.4291 | 0.6652 | 0.034* | 0.791 (6) |
C2' | 0.3343 (5) | 0.5782 (10) | 0.7584 (8) | 0.0247 (17) | 0.209 (6) |
H2' | 0.3532 | 0.6274 | 0.6965 | 0.030* | 0.209 (6) |
C3' | 0.3709 (4) | 0.4339 (7) | 0.7639 (6) | 0.0254 (19) | 0.209 (6) |
H3'1 | 0.3391 | 0.3796 | 0.7019 | 0.031* | 0.209 (6) |
H3'2 | 0.3602 | 0.3885 | 0.8306 | 0.031* | 0.209 (6) |
C4 | 0.47062 (9) | 0.43667 (13) | 0.76273 (11) | 0.0293 (3) | |
H4A | 0.4619 | 0.3473 | 0.7979 | 0.035* | |
H4B | 0.5073 | 0.4197 | 0.7066 | 0.035* | |
C5 | 0.51773 (8) | 0.53692 (12) | 0.84345 (10) | 0.0242 (2) | |
C6 | 0.47471 (8) | 0.63949 (12) | 0.89128 (10) | 0.0233 (2) | |
N1 | 0.60874 (7) | 0.54516 (11) | 0.87892 (9) | 0.0271 (2) | |
C7 | 0.67788 (10) | 0.45190 (17) | 0.85347 (13) | 0.0398 (3) | |
H7A | 0.7046 | 0.3995 | 0.9179 | 0.060* | |
H7B | 0.7252 | 0.5059 | 0.8285 | 0.060* | |
H7C | 0.6504 | 0.3875 | 0.7968 | 0.060* | |
C11 | 0.54397 (9) | 0.83385 (13) | 1.02566 (11) | 0.0287 (3) | |
H11 | 0.4887 | 0.8760 | 1.0345 | 0.034* | |
C12 | 0.62640 (10) | 0.88621 (14) | 1.07744 (12) | 0.0333 (3) | |
H12 | 0.6275 | 0.9663 | 1.1214 | 0.040* | |
C13 | 0.70791 (9) | 0.82355 (14) | 1.06628 (11) | 0.0327 (3) | |
H13 | 0.7633 | 0.8616 | 1.1033 | 0.039* | |
C14 | 0.70995 (9) | 0.70743 (14) | 1.00265 (11) | 0.0299 (3) | |
H14 | 0.7654 | 0.6645 | 0.9953 | 0.036* | |
C15 | 0.62667 (8) | 0.65657 (12) | 0.94981 (10) | 0.0250 (2) | |
C16 | 0.54407 (8) | 0.71765 (12) | 0.96013 (10) | 0.0235 (2) | |
N21 | 0.17623 (7) | 0.50012 (11) | 0.68255 (9) | 0.0263 (2) | |
C21 | 0.23061 (9) | 0.60123 (14) | 0.75318 (11) | 0.0296 (3) | |
H21A | 0.1997 | 0.6237 | 0.8136 | 0.035* | |
H21B | 0.2353 | 0.6877 | 0.7124 | 0.035* | |
C22 | 0.14748 (8) | 0.51214 (13) | 0.57668 (10) | 0.0255 (2) | |
N23 | 0.10021 (7) | 0.39848 (11) | 0.54364 (9) | 0.0275 (2) | |
H23 | 0.0737 (14) | 0.380 (2) | 0.4738 (17) | 0.052 (5)* | |
C24 | 0.09870 (10) | 0.31217 (14) | 0.62952 (11) | 0.0325 (3) | |
H24 | 0.0699 | 0.2243 | 0.6277 | 0.039* | |
C25 | 0.14590 (9) | 0.37590 (14) | 0.71680 (11) | 0.0314 (3) | |
H25 | 0.1564 | 0.3418 | 0.7885 | 0.038* | |
C26 | 0.16314 (10) | 0.62967 (15) | 0.50696 (12) | 0.0353 (3) | |
H26A | 0.1302 | 0.6134 | 0.4336 | 0.053* | |
H26B | 0.2281 | 0.6377 | 0.5064 | 0.053* | |
H26C | 0.1415 | 0.7156 | 0.5348 | 0.053* | |
O1W | 0.02177 (9) | 0.35198 (13) | 0.33988 (9) | 0.0460 (3) | |
H1WB | 0.0308 (14) | 0.406 (2) | 0.2929 (18) | 0.054 (6)* | |
H1WA | −0.0074 (16) | 0.279 (3) | 0.3157 (19) | 0.065 (6)* | |
O2W | −0.10943 (9) | 0.49567 (17) | 0.05256 (12) | 0.0553 (3) | |
H2WA | −0.1021 (17) | 0.470 (3) | −0.007 (2) | 0.071 (7)* | |
H2WB | −0.054 (2) | 0.515 (3) | 0.087 (2) | 0.081 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.03523 (18) | 0.03761 (17) | 0.03515 (18) | 0.00018 (13) | 0.00751 (13) | −0.00090 (14) |
C1 | 0.0255 (6) | 0.0290 (6) | 0.0327 (7) | 0.0009 (5) | 0.0025 (5) | −0.0078 (5) |
O1 | 0.0261 (5) | 0.0469 (6) | 0.0613 (7) | 0.0045 (4) | 0.0027 (5) | −0.0286 (5) |
C2 | 0.0238 (9) | 0.0278 (10) | 0.0222 (11) | −0.0013 (7) | 0.0051 (8) | −0.0028 (8) |
C3 | 0.0278 (8) | 0.0313 (10) | 0.0241 (9) | 0.0011 (6) | 0.0031 (6) | −0.0056 (8) |
C2' | 0.021 (3) | 0.035 (4) | 0.019 (4) | −0.006 (3) | 0.005 (3) | −0.004 (3) |
C3' | 0.024 (3) | 0.026 (3) | 0.027 (4) | −0.002 (2) | 0.004 (2) | −0.005 (3) |
C4 | 0.0300 (6) | 0.0284 (6) | 0.0296 (6) | 0.0027 (5) | 0.0056 (5) | −0.0072 (5) |
C5 | 0.0260 (6) | 0.0243 (5) | 0.0222 (6) | 0.0027 (5) | 0.0042 (4) | 0.0018 (4) |
C6 | 0.0241 (6) | 0.0224 (5) | 0.0231 (6) | −0.0004 (4) | 0.0037 (4) | −0.0004 (4) |
N1 | 0.0243 (5) | 0.0299 (5) | 0.0266 (5) | 0.0050 (4) | 0.0034 (4) | −0.0010 (4) |
C7 | 0.0323 (7) | 0.0493 (8) | 0.0374 (8) | 0.0166 (6) | 0.0049 (6) | −0.0061 (6) |
C11 | 0.0295 (6) | 0.0268 (6) | 0.0287 (6) | 0.0009 (5) | 0.0026 (5) | −0.0019 (5) |
C12 | 0.0363 (7) | 0.0295 (6) | 0.0314 (7) | −0.0036 (5) | −0.0003 (5) | −0.0035 (5) |
C13 | 0.0284 (7) | 0.0361 (7) | 0.0307 (7) | −0.0072 (5) | −0.0022 (5) | 0.0052 (5) |
C14 | 0.0234 (6) | 0.0363 (7) | 0.0291 (7) | 0.0003 (5) | 0.0023 (5) | 0.0076 (5) |
C15 | 0.0256 (6) | 0.0273 (6) | 0.0219 (6) | 0.0012 (5) | 0.0041 (4) | 0.0038 (5) |
C16 | 0.0240 (6) | 0.0245 (6) | 0.0218 (6) | −0.0004 (4) | 0.0033 (4) | 0.0030 (4) |
N21 | 0.0227 (5) | 0.0297 (5) | 0.0262 (5) | −0.0036 (4) | 0.0037 (4) | −0.0012 (4) |
C21 | 0.0239 (6) | 0.0334 (6) | 0.0303 (7) | −0.0038 (5) | 0.0021 (5) | −0.0083 (5) |
C22 | 0.0215 (6) | 0.0283 (6) | 0.0269 (6) | −0.0007 (4) | 0.0053 (5) | −0.0012 (5) |
N23 | 0.0266 (5) | 0.0298 (5) | 0.0257 (5) | −0.0041 (4) | 0.0038 (4) | −0.0028 (4) |
C24 | 0.0336 (7) | 0.0301 (6) | 0.0343 (7) | −0.0073 (5) | 0.0076 (5) | 0.0020 (5) |
C25 | 0.0311 (7) | 0.0341 (6) | 0.0290 (7) | −0.0055 (5) | 0.0054 (5) | 0.0042 (5) |
C26 | 0.0405 (8) | 0.0317 (7) | 0.0341 (7) | −0.0055 (6) | 0.0081 (6) | 0.0042 (6) |
O1W | 0.0676 (8) | 0.0406 (6) | 0.0272 (5) | −0.0150 (6) | 0.0024 (5) | −0.0019 (5) |
O2W | 0.0364 (7) | 0.0870 (10) | 0.0433 (7) | −0.0037 (6) | 0.0099 (5) | −0.0151 (7) |
Geometric parameters (Å, º) top
C1—O1 | 1.2259 (17) | C11—C16 | 1.3944 (18) |
C1—C6 | 1.4351 (17) | C11—H11 | 0.9500 |
C1—C2 | 1.526 (2) | C12—C13 | 1.396 (2) |
C1—C2' | 1.627 (8) | C12—H12 | 0.9500 |
C2—C21 | 1.505 (2) | C13—C14 | 1.383 (2) |
C2—C3 | 1.536 (3) | C13—H13 | 0.9500 |
C2—H2 | 1.0000 | C14—C15 | 1.3935 (18) |
C3—C4 | 1.549 (2) | C14—H14 | 0.9500 |
C3—H3A | 0.9900 | C15—C16 | 1.4015 (18) |
C3—H3B | 0.9900 | N21—C22 | 1.3341 (17) |
C2'—C3' | 1.493 (12) | N21—C25 | 1.3801 (17) |
C2'—C21 | 1.563 (8) | N21—C21 | 1.4650 (16) |
C2'—H2' | 1.0000 | C21—H21A | 0.9900 |
C3'—C4 | 1.501 (6) | C21—H21B | 0.9900 |
C3'—H3'1 | 0.9900 | C22—N23 | 1.3308 (16) |
C3'—H3'2 | 0.9900 | C22—C26 | 1.4819 (18) |
C4—C5 | 1.4868 (17) | N23—C24 | 1.3725 (18) |
C4—H4A | 0.9900 | N23—H23 | 0.92 (2) |
C4—H4B | 0.9900 | C24—C25 | 1.3453 (19) |
C5—N1 | 1.3597 (16) | C24—H24 | 0.9500 |
C5—C6 | 1.3814 (17) | C25—H25 | 0.9500 |
C6—C16 | 1.4407 (16) | C26—H26A | 0.9800 |
N1—C15 | 1.3938 (16) | C26—H26B | 0.9800 |
N1—C7 | 1.4547 (17) | C26—H26C | 0.9800 |
C7—H7A | 0.9800 | O1W—H1WB | 0.82 (2) |
C7—H7B | 0.9800 | O1W—H1WA | 0.85 (3) |
C7—H7C | 0.9800 | O2W—H2WA | 0.82 (3) |
C11—C12 | 1.3843 (19) | O2W—H2WB | 0.89 (3) |
| | | |
O1—C1—C6 | 123.36 (12) | H7B—C7—H7C | 109.5 |
O1—C1—C2 | 120.65 (14) | C12—C11—C16 | 118.37 (13) |
C6—C1—C2 | 115.85 (13) | C12—C11—H11 | 120.8 |
O1—C1—C2' | 123.6 (3) | C16—C11—H11 | 120.8 |
C6—C1—C2' | 110.0 (3) | C11—C12—C13 | 121.22 (13) |
C21—C2—C1 | 109.91 (14) | C11—C12—H12 | 119.4 |
C21—C2—C3 | 114.6 (2) | C13—C12—H12 | 119.4 |
C1—C2—C3 | 110.11 (18) | C14—C13—C12 | 121.62 (12) |
C21—C2—H2 | 107.3 | C14—C13—H13 | 119.2 |
C1—C2—H2 | 107.3 | C12—C13—H13 | 119.2 |
C3—C2—H2 | 107.3 | C13—C14—C15 | 116.70 (13) |
C2—C3—C4 | 111.86 (16) | C13—C14—H14 | 121.6 |
C2—C3—H3A | 109.2 | C15—C14—H14 | 121.6 |
C4—C3—H3A | 109.2 | C14—C15—N1 | 128.99 (12) |
C2—C3—H3B | 109.2 | C14—C15—C16 | 122.60 (12) |
C4—C3—H3B | 109.2 | N1—C15—C16 | 108.40 (11) |
H3A—C3—H3B | 107.9 | C11—C16—C15 | 119.48 (11) |
C3'—C2'—C21 | 119.3 (7) | C11—C16—C6 | 134.41 (12) |
C3'—C2'—C1 | 108.1 (7) | C15—C16—C6 | 106.07 (11) |
C21—C2'—C1 | 102.1 (5) | C22—N21—C25 | 109.07 (10) |
C3'—C2'—H2' | 108.9 | C22—N21—C21 | 126.48 (11) |
C21—C2'—H2' | 108.9 | C25—N21—C21 | 124.45 (11) |
C1—C2'—H2' | 108.9 | N21—C21—C2 | 112.09 (12) |
C2'—C3'—C4 | 110.0 (6) | N21—C21—C2' | 111.7 (3) |
C2'—C3'—H3'1 | 109.7 | N21—C21—H21A | 109.2 |
C4—C3'—H3'1 | 109.7 | C2—C21—H21A | 109.2 |
C2'—C3'—H3'2 | 109.7 | C2'—C21—H21A | 127.3 |
C4—C3'—H3'2 | 109.7 | N21—C21—H21B | 109.2 |
H3'1—C3'—H3'2 | 108.2 | C2—C21—H21B | 109.2 |
C5—C4—C3' | 110.7 (2) | C2'—C21—H21B | 88.5 |
C5—C4—C3 | 108.03 (11) | H21A—C21—H21B | 107.9 |
C5—C4—H4A | 110.1 | N23—C22—N21 | 107.34 (11) |
C3'—C4—H4A | 76.4 | N23—C22—C26 | 125.29 (12) |
C3—C4—H4A | 110.1 | N21—C22—C26 | 127.36 (12) |
C5—C4—H4B | 110.1 | C22—N23—C24 | 109.72 (11) |
C3'—C4—H4B | 133.9 | C22—N23—H23 | 124.8 (13) |
C3—C4—H4B | 110.1 | C24—N23—H23 | 125.5 (13) |
H4A—C4—H4B | 108.4 | C25—C24—N23 | 106.80 (12) |
N1—C5—C6 | 109.69 (11) | C25—C24—H24 | 126.6 |
N1—C5—C4 | 125.87 (11) | N23—C24—H24 | 126.6 |
C6—C5—C4 | 124.41 (11) | C24—C25—N21 | 107.06 (12) |
C5—C6—C1 | 122.70 (11) | C24—C25—H25 | 126.5 |
C5—C6—C16 | 107.17 (11) | N21—C25—H25 | 126.5 |
C1—C6—C16 | 130.12 (11) | C22—C26—H26A | 109.5 |
C5—N1—C15 | 108.65 (10) | C22—C26—H26B | 109.5 |
C5—N1—C7 | 127.31 (11) | H26A—C26—H26B | 109.5 |
C15—N1—C7 | 123.98 (11) | C22—C26—H26C | 109.5 |
N1—C7—H7A | 109.5 | H26A—C26—H26C | 109.5 |
N1—C7—H7B | 109.5 | H26B—C26—H26C | 109.5 |
H7A—C7—H7B | 109.5 | H1WB—O1W—H1WA | 114 (2) |
N1—C7—H7C | 109.5 | H2WA—O2W—H2WB | 104 (3) |
H7A—C7—H7C | 109.5 | | |
| | | |
O1—C1—C2—C21 | 22.0 (3) | C12—C13—C14—C15 | 0.34 (19) |
C6—C1—C2—C21 | −162.28 (16) | C13—C14—C15—N1 | 177.86 (12) |
C2'—C1—C2—C21 | −82.6 (9) | C13—C14—C15—C16 | −0.52 (19) |
O1—C1—C2—C3 | 149.11 (17) | C5—N1—C15—C14 | −177.44 (13) |
C6—C1—C2—C3 | −35.1 (2) | C7—N1—C15—C14 | 5.2 (2) |
C2'—C1—C2—C3 | 44.5 (9) | C5—N1—C15—C16 | 1.13 (14) |
C21—C2—C3—C4 | −176.08 (14) | C7—N1—C15—C16 | −176.24 (12) |
C1—C2—C3—C4 | 59.4 (2) | C12—C11—C16—C15 | 0.89 (19) |
O1—C1—C2'—C3' | −149.4 (5) | C12—C11—C16—C6 | −176.58 (14) |
C6—C1—C2'—C3' | 49.7 (8) | C14—C15—C16—C11 | −0.10 (19) |
C2—C1—C2'—C3' | −59.9 (9) | N1—C15—C16—C11 | −178.77 (11) |
O1—C1—C2'—C21 | −22.7 (8) | C14—C15—C16—C6 | 178.02 (11) |
C6—C1—C2'—C21 | 176.3 (4) | N1—C15—C16—C6 | −0.66 (13) |
C2—C1—C2'—C21 | 66.7 (8) | C5—C6—C16—C11 | 177.67 (14) |
C21—C2'—C3'—C4 | 177.2 (5) | C1—C6—C16—C11 | −1.2 (2) |
C1—C2'—C3'—C4 | −66.9 (8) | C5—C6—C16—C15 | −0.04 (13) |
C2'—C3'—C4—C5 | 49.5 (7) | C1—C6—C16—C15 | −178.94 (13) |
C2'—C3'—C4—C3 | −42.8 (6) | C22—N21—C21—C2 | −112.50 (18) |
C2—C3—C4—C5 | −51.1 (2) | C25—N21—C21—C2 | 68.0 (2) |
C2—C3—C4—C3' | 49.4 (4) | C22—N21—C21—C2' | −87.6 (5) |
C3'—C4—C5—N1 | 165.7 (3) | C25—N21—C21—C2' | 92.9 (5) |
C3—C4—C5—N1 | −156.52 (14) | C1—C2—C21—N21 | 179.46 (16) |
C3'—C4—C5—C6 | −16.5 (4) | C3—C2—C21—N21 | 54.9 (2) |
C3—C4—C5—C6 | 21.28 (19) | C1—C2—C21—C2' | 85.7 (8) |
N1—C5—C6—C1 | 179.74 (12) | C3—C2—C21—C2' | −38.9 (8) |
C4—C5—C6—C1 | 1.6 (2) | C3'—C2'—C21—N21 | −40.7 (9) |
N1—C5—C6—C16 | 0.74 (14) | C1—C2'—C21—N21 | −159.8 (4) |
C4—C5—C6—C16 | −177.37 (12) | C3'—C2'—C21—C2 | 54.9 (9) |
O1—C1—C6—C5 | −178.95 (14) | C1—C2'—C21—C2 | −64.1 (7) |
C2—C1—C6—C5 | 5.4 (2) | C25—N21—C22—N23 | −0.22 (14) |
C2'—C1—C6—C5 | −17.9 (5) | C21—N21—C22—N23 | −179.75 (12) |
O1—C1—C6—C16 | −0.2 (2) | C25—N21—C22—C26 | 179.03 (13) |
C2—C1—C6—C16 | −175.80 (17) | C21—N21—C22—C26 | −0.5 (2) |
C2'—C1—C6—C16 | 160.8 (4) | N21—C22—N23—C24 | −0.08 (15) |
C6—C5—N1—C15 | −1.16 (14) | C26—C22—N23—C24 | −179.35 (13) |
C4—C5—N1—C15 | 176.91 (12) | C22—N23—C24—C25 | 0.35 (16) |
C6—C5—N1—C7 | 176.09 (13) | N23—C24—C25—N21 | −0.48 (16) |
C4—C5—N1—C7 | −5.8 (2) | C22—N21—C25—C24 | 0.44 (16) |
C16—C11—C12—C13 | −1.1 (2) | C21—N21—C25—C24 | 179.98 (12) |
C11—C12—C13—C14 | 0.5 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N23—H23···O1W | 0.92 (2) | 1.75 (2) | 2.6663 (16) | 178.0 (19) |
O1W—H1WB···Cl1 | 0.82 (2) | 2.32 (2) | 3.1252 (14) | 166 (2) |
O2W—H2WB···Cl1 | 0.89 (3) | 2.33 (3) | 3.2171 (15) | 175 (2) |
O1W—H1WA···Cl1i | 0.85 (3) | 2.32 (3) | 3.1334 (14) | 161 (2) |
O2W—H2WA···Cl1ii | 0.82 (3) | 2.41 (3) | 3.2205 (15) | 172 (2) |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, −y+1, −z. |