The title compound, C
7H
10N
+·C
7H
3ClNO
4−·C
7H
4ClNO
4, consists of a 3,5-lutidinium (3,5-dimethylpyridinium) cation, a 2-chloro-4-nitrobenzoate anion and 2-chloro-4-nitrobenzoic acid. The anion is linked to the cation and the acid, respectively, by N—H
O and O—H
O hydrogen bonds. There are three C—H
O hydrogen bonds which connect the lutidinium–benzoate–benzoic acid units, forming a molecular tape.
Supporting information
CCDC reference: 252958
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.005 Å
- R factor = 0.059
- wR factor = 0.167
- Data-to-parameter ratio = 16.4
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact O1 .. N1 .. 2.85 Ang.
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.12
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.12
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.51
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C7 ... 1.53 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact Cl2 .. O1 .. 3.12 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3
C7 H3 Cl N O4
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
8 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
6 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1990); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (MSC, 1997-1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); 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).
Crystal data top
C7H10N+·C7H3ClNO4−·C7H4ClNO4 | Z = 2 |
Mr = 510.28 | F(000) = 524.00 |
Triclinic, P1 | Dx = 1.503 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.517 (3) Å | Cell parameters from 25 reflections |
b = 9.9163 (19) Å | θ = 10.1–12.3° |
c = 13.194 (5) Å | µ = 0.34 mm−1 |
α = 75.30 (2)° | T = 296 K |
β = 70.12 (3)° | Prism, colorless |
γ = 80.030 (19)° | 0.40 × 0.30 × 0.25 mm |
V = 1127.5 (6) Å3 | |
Data collection top
Rigaku AFC-5R diffractometer | 2574 reflections with I > 2σ(I) |
Radiation source: Rigaku rotating anode | Rint = 0.038 |
Graphite monochromator | θmax = 27.5°, θmin = 2.1° |
ω–2θ scans | h = −12→12 |
Absorption correction: ψ scan (North et al., 1968) | k = −12→0 |
Tmin = 0.846, Tmax = 0.918 | l = −17→16 |
5486 measured reflections | 3 standard reflections every 97 reflections |
5184 independent reflections | intensity decay: 2.5% |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.059 | w = 1/[σ2(Fo2) + (0.071P)2 + 0.0055P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.167 | (Δ/σ)max = 0.01 |
S = 1.01 | Δρmax = 0.39 e Å−3 |
5184 reflections | Δρmin = −0.34 e Å−3 |
317 parameters | |
Special details top
Experimental. The scan width was (1.42 + 0.30tanθ)° with an ω scan speed of 4° per minute
(up to 4 scans to achieve I/σ(I) > 10). Stationary background counts were
recorded at each end of the scan, and the scan time:background time ratio was
2:1. |
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 | |
Cl1 | −0.30070 (10) | 0.10620 (11) | 0.86869 (8) | 0.0708 (4) | |
Cl2 | 0.53431 (10) | 0.06480 (12) | 0.25628 (8) | 0.0698 (4) | |
O1 | 0.1586 (3) | 0.0924 (3) | 0.72563 (18) | 0.0582 (7) | |
O2 | −0.0245 (3) | 0.0473 (3) | 0.67355 (19) | 0.0648 (8) | |
O3 | −0.3384 (3) | −0.2813 (3) | 1.2191 (2) | 0.0746 (9) | |
O4 | −0.1166 (4) | −0.3827 (3) | 1.2124 (2) | 0.0877 (10) | |
O5 | 0.0702 (3) | 0.1639 (3) | 0.4707 (2) | 0.0531 (7) | |
O6 | 0.2697 (3) | 0.0088 (3) | 0.4458 (2) | 0.0704 (8) | |
O7 | 0.4922 (3) | 0.4188 (3) | −0.0899 (2) | 0.0759 (9) | |
O8 | 0.2685 (4) | 0.5172 (3) | −0.0615 (2) | 0.0913 (11) | |
N1 | −0.2023 (4) | −0.2975 (3) | 1.1732 (2) | 0.0588 (9) | |
N2 | 0.3636 (4) | 0.4357 (3) | −0.0314 (2) | 0.0599 (9) | |
N3 | 0.3205 (3) | 0.2638 (3) | 0.5513 (2) | 0.0466 (7) | |
C1 | −0.0278 (3) | −0.0412 (3) | 0.8577 (2) | 0.0377 (7) | |
C2 | −0.1796 (3) | −0.0242 (3) | 0.9181 (2) | 0.0390 (8) | |
C3 | −0.2361 (4) | −0.1065 (4) | 1.0222 (2) | 0.0463 (9) | |
C4 | −0.1415 (4) | −0.2064 (3) | 1.0637 (2) | 0.0454 (8) | |
C5 | 0.0088 (4) | −0.2259 (4) | 1.0094 (3) | 0.0525 (9) | |
C6 | 0.0643 (4) | −0.1417 (4) | 0.9057 (3) | 0.0465 (9) | |
C7 | 0.0413 (3) | 0.0420 (3) | 0.7408 (3) | 0.0413 (8) | |
C8 | 0.2458 (3) | 0.1935 (3) | 0.2948 (2) | 0.0392 (8) | |
C9 | 0.3905 (3) | 0.1786 (3) | 0.2217 (3) | 0.0433 (8) | |
C10 | 0.4281 (4) | 0.2586 (4) | 0.1154 (3) | 0.0472 (9) | |
C11 | 0.3205 (4) | 0.3520 (4) | 0.0828 (3) | 0.0486 (9) | |
C12 | 0.1764 (4) | 0.3705 (4) | 0.1504 (3) | 0.0546 (10) | |
C13 | 0.1416 (4) | 0.2911 (4) | 0.2563 (3) | 0.0527 (9) | |
C14 | 0.1981 (4) | 0.1102 (4) | 0.4112 (3) | 0.0442 (8) | |
C15 | 0.4662 (4) | 0.2316 (4) | 0.5052 (3) | 0.0469 (9) | |
C16 | 0.5471 (4) | 0.3245 (4) | 0.4157 (3) | 0.0501 (9) | |
C17 | 0.4699 (4) | 0.4467 (4) | 0.3774 (3) | 0.0550 (10) | |
C18 | 0.3190 (4) | 0.4789 (4) | 0.4253 (3) | 0.0564 (10) | |
C19 | 0.2471 (4) | 0.3817 (4) | 0.5156 (3) | 0.0528 (9) | |
C20 | 0.7133 (4) | 0.2895 (5) | 0.3625 (3) | 0.0754 (13) | |
C21 | 0.2362 (5) | 0.6128 (5) | 0.3822 (4) | 0.1039 (18) | |
H1 | −0.3368 | −0.0935 | 1.0628 | 0.056* | |
H2 | 0.0716 | −0.2932 | 1.0409 | 0.063* | |
H3 | 0.1661 | −0.1532 | 0.8674 | 0.056* | |
H4 | 0.5249 | 0.2488 | 0.0672 | 0.057* | |
H5 | 0.1049 | 0.4342 | 0.1258 | 0.066* | |
H6 | 0.0447 | 0.3031 | 0.3039 | 0.063* | |
H7 | 0.055 (6) | 0.114 (5) | 0.537 (4) | 0.13 (2)* | |
H8 | 0.273 (4) | 0.194 (4) | 0.605 (3) | 0.075 (12)* | |
H9 | 0.5134 | 0.1470 | 0.5330 | 0.056* | |
H10 | 0.5220 | 0.5100 | 0.3166 | 0.066* | |
H11 | 0.1454 | 0.3996 | 0.5517 | 0.063* | |
H12 | 0.7336 | 0.2981 | 0.2849 | 0.113* | |
H13 | 0.7426 | 0.1953 | 0.3949 | 0.113* | |
H14 | 0.7691 | 0.3531 | 0.3741 | 0.113* | |
H15 | 0.3001 | 0.6874 | 0.3572 | 0.156* | |
H16 | 0.1479 | 0.6351 | 0.4400 | 0.156* | |
H17 | 0.2077 | 0.6014 | 0.3220 | 0.156* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0528 (5) | 0.0719 (7) | 0.0561 (6) | 0.0106 (5) | −0.0001 (4) | 0.0073 (5) |
Cl2 | 0.0430 (5) | 0.0890 (8) | 0.0529 (6) | 0.0108 (5) | −0.0034 (4) | 0.0007 (5) |
O1 | 0.0519 (14) | 0.0725 (18) | 0.0396 (13) | −0.0338 (13) | −0.0031 (11) | 0.0101 (12) |
O2 | 0.0570 (15) | 0.099 (2) | 0.0305 (13) | −0.0316 (15) | −0.0048 (12) | 0.0035 (13) |
O3 | 0.082 (2) | 0.084 (2) | 0.0417 (15) | −0.0458 (16) | 0.0086 (14) | 0.0033 (14) |
O4 | 0.119 (3) | 0.066 (2) | 0.0472 (16) | −0.0034 (18) | −0.0118 (17) | 0.0188 (15) |
O5 | 0.0438 (13) | 0.0630 (17) | 0.0354 (13) | −0.0028 (11) | 0.0026 (10) | −0.0026 (12) |
O6 | 0.0532 (15) | 0.077 (2) | 0.0512 (16) | 0.0079 (14) | −0.0055 (12) | 0.0133 (14) |
O7 | 0.089 (2) | 0.078 (2) | 0.0391 (15) | −0.0189 (16) | 0.0069 (14) | −0.0036 (14) |
O8 | 0.110 (3) | 0.078 (2) | 0.0553 (18) | 0.0089 (19) | −0.0183 (17) | 0.0163 (16) |
N1 | 0.085 (2) | 0.048 (2) | 0.0320 (16) | −0.0273 (17) | −0.0019 (16) | 0.0029 (14) |
N2 | 0.080 (2) | 0.049 (2) | 0.0401 (17) | −0.0118 (17) | −0.0089 (17) | −0.0014 (15) |
N3 | 0.0465 (17) | 0.0497 (19) | 0.0333 (15) | −0.0170 (14) | −0.0039 (13) | 0.0060 (13) |
C1 | 0.0407 (17) | 0.0379 (18) | 0.0283 (16) | −0.0149 (14) | −0.0009 (13) | −0.0024 (13) |
C2 | 0.0386 (17) | 0.0392 (18) | 0.0314 (16) | −0.0067 (14) | −0.0024 (13) | −0.0037 (14) |
C3 | 0.0402 (18) | 0.050 (2) | 0.0358 (18) | −0.0169 (16) | 0.0069 (14) | −0.0043 (16) |
C4 | 0.062 (2) | 0.0390 (19) | 0.0258 (16) | −0.0171 (16) | −0.0012 (15) | 0.0005 (14) |
C5 | 0.055 (2) | 0.048 (2) | 0.0416 (19) | −0.0040 (17) | −0.0096 (16) | 0.0046 (16) |
C6 | 0.0428 (18) | 0.050 (2) | 0.0367 (18) | −0.0082 (16) | −0.0026 (14) | −0.0022 (16) |
C7 | 0.0368 (17) | 0.0403 (19) | 0.0329 (17) | −0.0081 (14) | 0.0008 (14) | 0.0037 (14) |
C8 | 0.0377 (17) | 0.0395 (19) | 0.0360 (17) | −0.0083 (14) | −0.0059 (13) | −0.0048 (14) |
C9 | 0.0381 (17) | 0.048 (2) | 0.0399 (18) | −0.0023 (15) | −0.0093 (14) | −0.0069 (15) |
C10 | 0.0437 (19) | 0.053 (2) | 0.0372 (18) | −0.0086 (16) | −0.0017 (15) | −0.0076 (16) |
C11 | 0.061 (2) | 0.044 (2) | 0.0344 (18) | −0.0135 (17) | −0.0072 (16) | −0.0031 (15) |
C12 | 0.055 (2) | 0.048 (2) | 0.048 (2) | 0.0003 (17) | −0.0124 (17) | 0.0036 (17) |
C13 | 0.0402 (18) | 0.055 (2) | 0.045 (2) | −0.0011 (16) | −0.0004 (15) | −0.0008 (17) |
C14 | 0.0363 (17) | 0.052 (2) | 0.0382 (18) | −0.0113 (15) | −0.0056 (14) | −0.0021 (16) |
C15 | 0.049 (2) | 0.044 (2) | 0.0406 (18) | −0.0087 (16) | −0.0089 (16) | −0.0007 (15) |
C16 | 0.050 (2) | 0.051 (2) | 0.0403 (19) | −0.0146 (17) | −0.0017 (15) | −0.0026 (16) |
C17 | 0.062 (2) | 0.047 (2) | 0.0400 (19) | −0.0201 (18) | −0.0002 (16) | 0.0069 (16) |
C18 | 0.056 (2) | 0.048 (2) | 0.051 (2) | −0.0053 (17) | −0.0111 (18) | 0.0060 (17) |
C19 | 0.0401 (18) | 0.059 (2) | 0.049 (2) | −0.0069 (17) | −0.0071 (16) | −0.0009 (18) |
C20 | 0.049 (2) | 0.077 (3) | 0.075 (3) | −0.012 (2) | 0.009 (2) | −0.007 (2) |
C21 | 0.098 (4) | 0.081 (3) | 0.097 (4) | 0.015 (3) | −0.028 (3) | 0.023 (3) |
Geometric parameters (Å, º) top
Cl1—C2 | 1.730 (3) | C11—C12 | 1.368 (5) |
Cl2—C9 | 1.726 (3) | C12—C13 | 1.379 (4) |
O1—C7 | 1.236 (4) | C15—C16 | 1.382 (4) |
O2—C7 | 1.235 (4) | C16—C17 | 1.377 (5) |
O3—N1 | 1.231 (4) | C16—C20 | 1.515 (5) |
O4—N1 | 1.214 (4) | C17—C18 | 1.375 (5) |
O5—C14 | 1.311 (4) | C18—C19 | 1.381 (4) |
O6—C14 | 1.193 (4) | C18—C21 | 1.506 (5) |
O7—N2 | 1.214 (4) | O5—H7 | 0.87 (5) |
O8—N2 | 1.208 (4) | N3—H8 | 0.91 (4) |
N1—C4 | 1.479 (4) | C3—H1 | 0.9300 |
N2—C11 | 1.480 (4) | C5—H2 | 0.9300 |
N3—C19 | 1.318 (4) | C6—H3 | 0.9300 |
N3—C15 | 1.329 (4) | C10—H4 | 0.9300 |
C1—C6 | 1.384 (4) | C12—H5 | 0.9300 |
C1—C2 | 1.397 (4) | C13—H6 | 0.9300 |
C1—C7 | 1.531 (4) | C15—H9 | 0.9300 |
C2—C3 | 1.387 (4) | C17—H10 | 0.9300 |
C3—C4 | 1.357 (5) | C19—H11 | 0.9300 |
C4—C5 | 1.369 (4) | C20—H12 | 0.9599 |
C5—C6 | 1.389 (4) | C20—H13 | 0.9599 |
C8—C13 | 1.392 (4) | C20—H14 | 0.9599 |
C8—C9 | 1.396 (4) | C21—H15 | 0.9599 |
C8—C14 | 1.503 (4) | C21—H16 | 0.9599 |
C9—C10 | 1.384 (4) | C21—H17 | 0.9599 |
C10—C11 | 1.364 (5) | | |
| | | |
Cl2···O1i | 3.120 (3) | O3···H10iv | 2.48 |
O1···N1ii | 2.853 (4) | O2···C14v | 3.075 (5) |
O1···N3 | 2.658 (4) | O5···H6 | 2.35 |
O1···H8 | 1.77 (4) | O6···H13i | 2.51 |
O2···O5 | 2.542 (4) | O6···H9i | 2.41 |
O2···H7 | 1.70 (5) | O8···H2vi | 2.69 |
O7···C11iii | 3.159 (5) | | |
| | | |
Cl1—C2—C1 | 121.1 (2) | C15—C16—C17 | 117.3 (3) |
Cl1—C2—C3 | 117.9 (2) | C15—C16—C20 | 120.2 (3) |
O1—C7—O2 | 128.4 (3) | C16—C17—C18 | 122.7 (3) |
O1—C7—C1 | 115.1 (3) | C17—C16—C20 | 122.5 (3) |
O2—C7—C1 | 116.4 (3) | C17—C18—C19 | 116.3 (3) |
O3—N1—O4 | 124.0 (3) | C17—C18—C21 | 122.0 (3) |
O3—N1—C4 | 117.2 (3) | C19—C18—C21 | 121.6 (4) |
O4—N1—C4 | 118.9 (3) | C19—N3—H8 | 122 (2) |
C6—C1—C2 | 117.8 (3) | C15—N3—H8 | 114 (2) |
C6—C1—C7 | 118.3 (3) | C4—C3—H1 | 120.7 |
C2—C1—C7 | 123.8 (3) | C2—C3—H1 | 120.7 |
C3—C2—C1 | 121.0 (3) | C4—C5—H2 | 121.2 |
C4—C3—C2 | 118.6 (3) | C6—C5—H2 | 121.2 |
C3—C4—C5 | 123.0 (3) | C1—C6—H3 | 119.1 |
C3—C4—N1 | 118.9 (3) | C5—C6—H3 | 119.1 |
C5—C4—N1 | 118.1 (3) | C9—C10—H4 | 120.6 |
C4—C5—C6 | 117.7 (3) | C11—C10—H4 | 120.6 |
C1—C6—C5 | 121.8 (3) | C11—C12—H5 | 121.3 |
C14—O5—H7 | 106 (3) | C13—C12—H5 | 121.3 |
Cl2—C9—C8 | 123.6 (2) | C8—C13—H6 | 118.7 |
Cl2—C9—C10 | 115.6 (2) | C12—C13—H6 | 118.7 |
O5—C14—O6 | 124.1 (3) | N3—C15—H9 | 120.2 |
O5—C14—C8 | 111.9 (3) | C16—C15—H9 | 120.2 |
O6—C14—C8 | 123.9 (3) | C18—C17—H10 | 118.6 |
O7—N2—O8 | 123.4 (3) | C16—C17—H10 | 118.6 |
O7—N2—C11 | 118.5 (3) | N3—C19—H11 | 119.5 |
O8—N2—C11 | 118.1 (3) | C18—C19—H11 | 119.5 |
N2—C11—C10 | 117.6 (3) | C16—C20—H12 | 109.5 |
N2—C11—C12 | 119.3 (3) | C16—C20—H13 | 109.5 |
C8—C9—C10 | 120.9 (3) | H12—C20—H13 | 109.5 |
C9—C8—C13 | 117.4 (3) | C16—C20—H14 | 109.5 |
C9—C8—C14 | 123.5 (3) | H12—C20—H14 | 109.5 |
C10—C11—C12 | 123.1 (3) | H13—C20—H14 | 109.5 |
C11—C10—C9 | 118.8 (3) | C18—C21—H15 | 109.5 |
C11—C12—C13 | 117.4 (3) | C18—C21—H16 | 109.5 |
C12—C13—C8 | 122.6 (3) | H15—C21—H16 | 109.5 |
C13—C8—C14 | 119.2 (3) | C18—C21—H17 | 109.5 |
N3—C15—C16 | 119.6 (3) | H15—C21—H17 | 109.5 |
N3—C19—C18 | 121.0 (3) | H16—C21—H17 | 109.5 |
C15—N3—C19 | 123.1 (3) | | |
| | | |
C6—C1—C2—C3 | −0.7 (5) | Cl2—C9—C10—C11 | −179.3 (3) |
C7—C1—C2—C3 | 177.7 (3) | C9—C10—C11—C12 | 0.0 (6) |
C6—C1—C2—Cl1 | 175.8 (3) | C9—C10—C11—N2 | −179.7 (3) |
C7—C1—C2—Cl1 | −5.8 (5) | O8—N2—C11—C10 | 179.0 (4) |
C1—C2—C3—C4 | −1.3 (5) | O7—N2—C11—C10 | −0.9 (5) |
Cl1—C2—C3—C4 | −178.0 (3) | O8—N2—C11—C12 | −0.8 (5) |
C2—C3—C4—C5 | 2.9 (5) | O7—N2—C11—C12 | 179.4 (4) |
C2—C3—C4—N1 | −178.1 (3) | C10—C11—C12—C13 | 0.7 (6) |
O4—N1—C4—C3 | −176.8 (4) | N2—C11—C12—C13 | −179.5 (3) |
O3—N1—C4—C3 | 3.0 (5) | C11—C12—C13—C8 | −1.0 (6) |
O4—N1—C4—C5 | 2.3 (5) | C9—C8—C13—C12 | 0.5 (6) |
O3—N1—C4—C5 | −177.8 (3) | C14—C8—C13—C12 | −179.4 (3) |
C3—C4—C5—C6 | −2.2 (5) | C13—C8—C14—O6 | 166.6 (4) |
N1—C4—C5—C6 | 178.7 (3) | C9—C8—C14—O6 | −13.3 (6) |
C2—C1—C6—C5 | 1.4 (5) | C13—C8—C14—O5 | −14.7 (5) |
C7—C1—C6—C5 | −177.1 (3) | C9—C8—C14—O5 | 165.4 (3) |
C4—C5—C6—C1 | 0.0 (5) | C19—N3—C15—C16 | 0.3 (5) |
C6—C1—C7—O2 | 129.3 (3) | N3—C15—C16—C17 | −1.2 (5) |
C2—C1—C7—O2 | −49.1 (5) | N3—C15—C16—C20 | 179.8 (3) |
C6—C1—C7—O1 | −49.1 (4) | C15—C16—C17—C18 | 0.9 (6) |
C2—C1—C7—O1 | 132.5 (3) | C20—C16—C17—C18 | 179.9 (4) |
C13—C8—C9—C10 | 0.3 (5) | C16—C17—C18—C19 | 0.3 (6) |
C14—C8—C9—C10 | −179.8 (3) | C16—C17—C18—C21 | −179.9 (4) |
C13—C8—C9—Cl2 | 178.9 (3) | C15—N3—C19—C18 | 1.0 (6) |
C14—C8—C9—Cl2 | −1.2 (5) | C17—C18—C19—N3 | −1.3 (6) |
C8—C9—C10—C11 | −0.5 (5) | C21—C18—C19—N3 | 178.9 (4) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y, −z+2; (iii) −x+1, −y+1, −z; (iv) x−1, y−1, z+1; (v) −x, −y, −z+1; (vi) x, y+1, z−1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H7···O2 | 0.87 (5) | 1.70 (5) | 2.542 (4) | 163 (6) |
N3—H8···O1 | 0.91 (4) | 1.77 (4) | 2.658 (4) | 166 (4) |
C15—H9···O6i | 0.93 | 2.41 | 3.266 (5) | 153 |
C17—H10···O3vii | 0.93 | 2.48 | 3.350 (5) | 156 |
C20—H13···O6i | 0.96 | 2.51 | 3.390 (5) | 153 |
Symmetry codes: (i) −x+1, −y, −z+1; (vii) x+1, y+1, z−1. |