

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314616002212/pk4001sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2414314616002212/pk4001Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314616002212/pk4001Isup3.cml |
CCDC reference: 1451830
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.032
- wR factor = 0.091
- Data-to-parameter ratio = 12.3
checkCIF/PLATON results
No syntax errors found
Alert level C THETM01_ALERT_3_C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5860 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.974 Note PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.586 83 Report PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers .... 1 Check
Alert level G PLAT005_ALERT_5_G No Embedded Refinement Details found in the CIF Please Do ! PLAT008_ALERT_5_G No _iucr_refine_reflections_details in the CIF Please Do ! PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still 89 % PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ... 1 Report PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density 9 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 4 ALERT level C = Check. Ensure it is not caused by an omission or oversight 5 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
C23H16Cl2N4 | F(000) = 1728 |
Mr = 419.30 | Dx = 1.427 Mg m−3 |
Orthorhombic, Pbca | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 3210 reflections |
a = 13.2330 (11) Å | θ = 4.3–64.6° |
b = 8.7515 (7) Å | µ = 3.13 mm−1 |
c = 33.695 (3) Å | T = 296 K |
V = 3902.2 (6) Å3 | Block, light yellow |
Z = 8 | 0.29 × 0.26 × 0.23 mm |
Bruker X8 Proteum diffractometer | 3210 independent reflections |
Radiation source: Bruker MicroStar microfocus rotating anode | 3089 reflections with I > 2σ(I) |
Helios multilayer optics monochromator | Rint = 0.041 |
Detector resolution: 10.7 pixels mm-1 | θmax = 64.6°, θmin = 4.3° |
φ and ω scans | h = −13→15 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | k = −10→8 |
Tmin = 0.464, Tmax = 0.533 | l = −38→38 |
20100 measured reflections |
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0531P)2 + 1.9833P] where P = (Fo2 + 2Fc2)/3 |
3210 reflections | (Δ/σ)max = 0.001 |
262 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > 2sigma(F2) is used only for calculating -R-factor-obs 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. |
x | y | z | Uiso*/Ueq | ||
Cl28 | 0.53010 (3) | 0.65530 (5) | 0.53902 (1) | 0.0260 (1) | |
Cl29 | 0.63027 (3) | 1.03517 (5) | 0.42010 (1) | 0.0302 (2) | |
N1 | 0.66079 (10) | 0.58214 (15) | 0.67786 (4) | 0.0182 (4) | |
N18 | 0.84679 (10) | 0.53348 (14) | 0.59627 (4) | 0.0193 (4) | |
N19 | 0.83790 (10) | 0.59721 (15) | 0.56132 (4) | 0.0193 (4) | |
N20 | 0.75208 (10) | 0.68295 (14) | 0.56223 (4) | 0.0170 (3) | |
C2 | 0.57186 (12) | 0.52280 (17) | 0.65898 (4) | 0.0181 (4) | |
C3 | 0.57308 (12) | 0.38226 (18) | 0.63960 (5) | 0.0205 (5) | |
C4 | 0.48933 (13) | 0.32968 (19) | 0.61912 (5) | 0.0241 (5) | |
C5 | 0.40285 (13) | 0.4183 (2) | 0.61745 (5) | 0.0260 (5) | |
C6 | 0.40111 (13) | 0.5588 (2) | 0.63632 (5) | 0.0255 (5) | |
C7 | 0.48426 (12) | 0.61320 (19) | 0.65786 (5) | 0.0212 (5) | |
C8 | 0.47687 (13) | 0.7600 (2) | 0.67837 (5) | 0.0261 (5) | |
C9 | 0.52101 (13) | 0.79772 (19) | 0.71276 (5) | 0.0256 (5) | |
C10 | 0.58799 (12) | 0.70227 (18) | 0.73680 (5) | 0.0209 (5) | |
C11 | 0.58832 (13) | 0.72054 (19) | 0.77811 (5) | 0.0254 (5) | |
C12 | 0.65044 (14) | 0.6344 (2) | 0.80224 (5) | 0.0264 (5) | |
C13 | 0.71444 (13) | 0.52698 (19) | 0.78552 (5) | 0.0247 (5) | |
C14 | 0.71582 (12) | 0.50611 (19) | 0.74478 (5) | 0.0211 (5) | |
C15 | 0.65428 (12) | 0.59383 (17) | 0.72018 (5) | 0.0184 (5) | |
C16 | 0.75821 (12) | 0.53003 (17) | 0.66218 (4) | 0.0184 (5) | |
C17 | 0.76794 (11) | 0.57852 (17) | 0.61969 (4) | 0.0172 (4) | |
C21 | 0.70728 (12) | 0.67415 (17) | 0.59844 (4) | 0.0175 (4) | |
C22 | 0.72075 (12) | 0.76532 (17) | 0.52791 (4) | 0.0177 (4) | |
C23 | 0.79272 (12) | 0.84767 (18) | 0.50702 (5) | 0.0207 (5) | |
C24 | 0.76590 (13) | 0.92902 (19) | 0.47349 (5) | 0.0225 (5) | |
C25 | 0.66572 (13) | 0.92946 (19) | 0.46149 (4) | 0.0218 (5) | |
C26 | 0.59215 (13) | 0.84824 (18) | 0.48186 (5) | 0.0214 (5) | |
C27 | 0.62067 (12) | 0.76384 (18) | 0.51495 (5) | 0.0192 (5) | |
H3 | 0.63120 | 0.32260 | 0.64040 | 0.0250* | |
H4 | 0.49120 | 0.23510 | 0.60650 | 0.0290* | |
H5 | 0.34630 | 0.38380 | 0.60370 | 0.0310* | |
H6 | 0.34320 | 0.61870 | 0.63470 | 0.0310* | |
H8 | 0.43750 | 0.83480 | 0.66630 | 0.0310* | |
H9 | 0.50760 | 0.89520 | 0.72240 | 0.0310* | |
H11 | 0.54560 | 0.79250 | 0.78960 | 0.0300* | |
H12 | 0.64930 | 0.64840 | 0.82960 | 0.0320* | |
H13 | 0.75650 | 0.46880 | 0.80170 | 0.0300* | |
H14 | 0.75820 | 0.43280 | 0.73370 | 0.0250* | |
H16A | 0.76260 | 0.41960 | 0.66400 | 0.0220* | |
H16B | 0.81280 | 0.57370 | 0.67770 | 0.0220* | |
H21 | 0.64850 | 0.72250 | 0.60680 | 0.0210* | |
H23 | 0.85950 | 0.84810 | 0.51560 | 0.0250* | |
H24 | 0.81440 | 0.98270 | 0.45920 | 0.0270* | |
H26 | 0.52510 | 0.85020 | 0.47350 | 0.0260* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl28 | 0.0191 (2) | 0.0327 (3) | 0.0262 (2) | −0.0071 (2) | 0.0001 (2) | 0.0035 (2) |
Cl29 | 0.0328 (3) | 0.0320 (3) | 0.0257 (2) | −0.0015 (2) | −0.0065 (2) | 0.0086 (2) |
N1 | 0.0192 (7) | 0.0194 (7) | 0.0159 (6) | 0.0014 (5) | 0.0018 (5) | −0.0003 (5) |
N18 | 0.0187 (7) | 0.0192 (7) | 0.0200 (7) | −0.0003 (5) | 0.0020 (5) | −0.0005 (5) |
N19 | 0.0182 (7) | 0.0197 (7) | 0.0200 (7) | 0.0015 (5) | 0.0013 (5) | −0.0008 (5) |
N20 | 0.0165 (6) | 0.0174 (6) | 0.0170 (6) | −0.0005 (5) | 0.0015 (5) | −0.0008 (5) |
C2 | 0.0192 (8) | 0.0205 (8) | 0.0146 (7) | −0.0003 (6) | 0.0033 (6) | 0.0041 (6) |
C3 | 0.0226 (8) | 0.0205 (8) | 0.0185 (8) | 0.0003 (7) | 0.0033 (6) | 0.0015 (6) |
C4 | 0.0280 (9) | 0.0257 (9) | 0.0187 (8) | −0.0062 (7) | 0.0021 (7) | 0.0008 (6) |
C5 | 0.0248 (9) | 0.0343 (10) | 0.0188 (8) | −0.0073 (7) | −0.0013 (7) | 0.0051 (7) |
C6 | 0.0196 (8) | 0.0339 (9) | 0.0229 (8) | 0.0035 (7) | 0.0022 (7) | 0.0086 (7) |
C7 | 0.0231 (8) | 0.0233 (8) | 0.0172 (8) | 0.0021 (7) | 0.0043 (6) | 0.0052 (6) |
C8 | 0.0276 (9) | 0.0243 (9) | 0.0263 (9) | 0.0092 (7) | 0.0039 (7) | 0.0047 (7) |
C9 | 0.0313 (9) | 0.0188 (8) | 0.0267 (9) | 0.0068 (7) | 0.0073 (7) | −0.0009 (7) |
C10 | 0.0247 (8) | 0.0164 (8) | 0.0216 (8) | −0.0023 (6) | 0.0036 (6) | −0.0015 (6) |
C11 | 0.0316 (9) | 0.0202 (8) | 0.0244 (8) | −0.0012 (7) | 0.0061 (7) | −0.0056 (7) |
C12 | 0.0358 (10) | 0.0266 (9) | 0.0168 (8) | −0.0054 (7) | 0.0007 (7) | −0.0037 (7) |
C13 | 0.0290 (9) | 0.0242 (9) | 0.0210 (8) | −0.0015 (7) | −0.0033 (7) | 0.0008 (6) |
C14 | 0.0236 (8) | 0.0185 (8) | 0.0212 (8) | 0.0006 (6) | 0.0002 (6) | −0.0013 (6) |
C15 | 0.0224 (8) | 0.0155 (8) | 0.0174 (8) | −0.0036 (6) | 0.0019 (6) | −0.0010 (6) |
C16 | 0.0195 (8) | 0.0171 (8) | 0.0186 (8) | 0.0020 (6) | 0.0008 (6) | 0.0003 (6) |
C17 | 0.0176 (8) | 0.0147 (7) | 0.0193 (8) | −0.0021 (6) | 0.0014 (6) | −0.0029 (6) |
C21 | 0.0196 (8) | 0.0165 (7) | 0.0165 (7) | −0.0013 (6) | 0.0028 (6) | −0.0022 (6) |
C22 | 0.0211 (8) | 0.0164 (7) | 0.0156 (7) | 0.0008 (6) | 0.0017 (6) | −0.0028 (6) |
C23 | 0.0191 (8) | 0.0221 (8) | 0.0210 (8) | −0.0005 (6) | 0.0008 (6) | −0.0017 (6) |
C24 | 0.0244 (9) | 0.0227 (8) | 0.0203 (8) | −0.0021 (6) | 0.0033 (7) | 0.0008 (6) |
C25 | 0.0283 (9) | 0.0195 (8) | 0.0177 (8) | 0.0009 (7) | −0.0015 (6) | −0.0009 (6) |
C26 | 0.0194 (8) | 0.0234 (8) | 0.0215 (8) | 0.0002 (6) | −0.0022 (6) | −0.0038 (6) |
C27 | 0.0191 (8) | 0.0195 (8) | 0.0191 (8) | −0.0016 (6) | 0.0020 (6) | −0.0034 (6) |
C2—C3 | 1.393 (2) | C24—C25 | 1.386 (2) |
C2—C7 | 1.404 (2) | C25—C26 | 1.387 (2) |
C3—C4 | 1.384 (2) | C26—C27 | 1.390 (2) |
C4—C5 | 1.384 (2) | C3—H3 | 0.9300 |
C5—C6 | 1.384 (2) | C4—H4 | 0.9300 |
C6—C7 | 1.402 (2) | C5—H5 | 0.9300 |
C7—C8 | 1.462 (2) | C6—H6 | 0.9300 |
C8—C9 | 1.339 (2) | C8—H8 | 0.9300 |
C9—C10 | 1.463 (2) | C9—H9 | 0.9300 |
C10—C11 | 1.401 (2) | C11—H11 | 0.9300 |
C10—C15 | 1.409 (2) | C12—H12 | 0.9300 |
C11—C12 | 1.380 (2) | C13—H13 | 0.9300 |
C12—C13 | 1.385 (2) | C14—H14 | 0.9300 |
C13—C14 | 1.385 (2) | C16—H16A | 0.9700 |
C14—C15 | 1.393 (2) | C16—H16B | 0.9700 |
C16—C17 | 1.4988 (19) | C21—H21 | 0.9300 |
C17—C21 | 1.363 (2) | C23—H23 | 0.9300 |
C22—C23 | 1.386 (2) | C24—H24 | 0.9300 |
C22—C27 | 1.395 (2) | C26—H26 | 0.9300 |
C23—C24 | 1.382 (2) | ||
Cl28···N20 | 3.0494 (14) | C13···H8vi | 3.0800 |
Cl28···C21 | 3.0876 (16) | C14···H16B | 2.6700 |
Cl28···C23i | 3.5035 (17) | C14···H16A | 2.8900 |
Cl28···C24i | 3.5980 (18) | C16···H3 | 2.5800 |
Cl28···H21 | 2.8300 | C16···H14 | 2.5600 |
Cl28···H23i | 2.9100 | C16···H3v | 3.0400 |
Cl28···H24i | 3.1000 | C17···H3v | 2.6100 |
Cl29···H5ii | 3.0500 | C17···H3 | 2.9600 |
Cl29···H4iii | 3.0000 | C21···H3v | 2.8700 |
N18···C21iv | 3.226 (2) | H3···C16 | 2.5800 |
N18···C22iv | 3.408 (2) | H3···C17 | 2.9600 |
N19···C27iv | 3.355 (2) | H3···H16A | 2.0900 |
N19···C23iv | 3.332 (2) | H3···N18iv | 2.9500 |
N19···C22iv | 3.210 (2) | H3···C16iv | 3.0400 |
N20···Cl28 | 3.0494 (14) | H3···C17iv | 2.6100 |
N1···H21 | 2.7000 | H3···C21iv | 2.8700 |
N18···H3v | 2.9500 | H4···Cl29iii | 3.0000 |
N18···H21iv | 2.7500 | H4···N18iv | 2.8000 |
N18···H4v | 2.8000 | H5···Cl29i | 3.0500 |
N19···H23 | 2.7000 | H5···H24i | 2.4600 |
N19···H26ii | 2.7800 | H6···H8 | 2.5000 |
C2···C21 | 3.021 (2) | H8···H6 | 2.5000 |
C3···C21 | 3.406 (2) | H8···C12viii | 3.0600 |
C3···C17 | 3.170 (2) | H8···C13viii | 3.0800 |
C3···C17iv | 3.456 (2) | H9···H11 | 2.4900 |
C17···C3 | 3.170 (2) | H9···C12viii | 3.0700 |
C17···C3v | 3.456 (2) | H11···H9 | 2.4900 |
C21···Cl28 | 3.0876 (16) | H11···C2viii | 3.0800 |
C21···N18v | 3.226 (2) | H11···C3viii | 2.9600 |
C21···C2 | 3.021 (2) | H12···C4viii | 2.9800 |
C21···C3 | 3.406 (2) | H12···C5viii | 3.0400 |
C22···C24iv | 3.472 (2) | H13···C6ix | 2.9400 |
C22···N19v | 3.210 (2) | H13···C11iv | 3.0900 |
C22···N18v | 3.408 (2) | H14···C16 | 2.5600 |
C23···Cl28ii | 3.5035 (17) | H14···H16A | 2.3500 |
C23···N19v | 3.332 (2) | H14···H16B | 2.3700 |
C24···C22v | 3.472 (2) | H14···C10iv | 2.8700 |
C24···C27v | 3.576 (2) | H16A···C3 | 2.6600 |
C24···Cl28ii | 3.5980 (18) | H16A···C14 | 2.8900 |
C27···N19v | 3.355 (2) | H16A···H3 | 2.0900 |
C27···C24iv | 3.576 (2) | H16A···H14 | 2.3500 |
C2···H11vi | 3.0800 | H16B···C14 | 2.6700 |
C2···H21 | 2.6800 | H16B···H14 | 2.3700 |
C3···H11vi | 2.9600 | H21···Cl28 | 2.8300 |
C3···H16A | 2.6600 | H21···N1 | 2.7000 |
C4···H12vi | 2.9800 | H21···C2 | 2.6800 |
C5···H24i | 2.9600 | H21···C7 | 2.9300 |
C5···H12vi | 3.0400 | H21···N18v | 2.7500 |
C6···H13vii | 2.9400 | H23···N19 | 2.7000 |
C7···H21 | 2.9300 | H23···Cl28ii | 2.9100 |
C10···H14v | 2.8700 | H24···Cl28ii | 3.1000 |
C11···H13v | 3.0900 | H24···C5ii | 2.9600 |
C12···H9vi | 3.0700 | H24···H5ii | 2.4600 |
C12···H8vi | 3.0600 | H26···N19i | 2.7800 |
C3—C2—C7 | 119.65 (14) | C4—C5—H5 | 120.00 |
C2—C3—C4 | 121.20 (15) | C6—C5—H5 | 120.00 |
C3—C4—C5 | 119.75 (15) | C5—C6—H6 | 119.00 |
C4—C5—C6 | 119.53 (16) | C7—C6—H6 | 119.00 |
C5—C6—C7 | 121.77 (16) | C7—C8—H8 | 117.00 |
C2—C7—C6 | 118.08 (15) | C9—C8—H8 | 117.00 |
C2—C7—C8 | 122.53 (15) | C8—C9—H9 | 116.00 |
C6—C7—C8 | 119.39 (15) | C10—C9—H9 | 116.00 |
C7—C8—C9 | 126.62 (16) | C10—C11—H11 | 119.00 |
C8—C9—C10 | 127.07 (16) | C12—C11—H11 | 119.00 |
C9—C10—C11 | 119.14 (15) | C11—C12—H12 | 120.00 |
C9—C10—C15 | 122.82 (15) | C13—C12—H12 | 120.00 |
C11—C10—C15 | 118.03 (15) | C12—C13—H13 | 120.00 |
C10—C11—C12 | 121.65 (16) | C14—C13—H13 | 120.00 |
C11—C12—C13 | 119.69 (16) | C13—C14—H14 | 120.00 |
C12—C13—C14 | 120.05 (16) | C15—C14—H14 | 120.00 |
C13—C14—C15 | 120.63 (15) | N1—C16—H16A | 110.00 |
C10—C15—C14 | 119.93 (15) | N1—C16—H16B | 110.00 |
C16—C17—C21 | 128.69 (13) | C17—C16—H16A | 110.00 |
C23—C22—C27 | 119.88 (14) | C17—C16—H16B | 110.00 |
C22—C23—C24 | 120.43 (15) | H16A—C16—H16B | 108.00 |
C23—C24—C25 | 119.06 (15) | N20—C21—H21 | 128.00 |
C24—C25—C26 | 121.70 (14) | C17—C21—H21 | 128.00 |
C25—C26—C27 | 118.60 (15) | C22—C23—H23 | 120.00 |
C22—C27—C26 | 120.28 (15) | C24—C23—H23 | 120.00 |
C2—C3—H3 | 119.00 | C23—C24—H24 | 120.00 |
C4—C3—H3 | 119.00 | C25—C24—H24 | 121.00 |
C3—C4—H4 | 120.00 | C25—C26—H26 | 121.00 |
C5—C4—H4 | 120.00 | C27—C26—H26 | 121.00 |
C15—N1—C2—C3 | −113.85 (16) | C6—C7—C8—C9 | 146.28 (18) |
C15—N1—C2—C7 | 70.45 (18) | C7—C8—C9—C10 | 1.6 (3) |
C16—N1—C2—C3 | 26.1 (2) | C8—C9—C10—C11 | −148.74 (18) |
C16—N1—C2—C7 | −149.60 (14) | C8—C9—C10—C15 | 32.6 (3) |
C2—N1—C15—C10 | −68.50 (18) | C9—C10—C11—C12 | −179.55 (16) |
C2—N1—C15—C14 | 114.92 (16) | C15—C10—C11—C12 | −0.8 (2) |
C16—N1—C15—C10 | 151.16 (14) | C9—C10—C15—N1 | 3.6 (2) |
C16—N1—C15—C14 | −25.4 (2) | C9—C10—C15—C14 | −179.74 (15) |
C2—N1—C16—C17 | 61.72 (16) | C11—C10—C15—N1 | −175.10 (14) |
C15—N1—C16—C17 | −158.73 (12) | C11—C10—C15—C14 | 1.5 (2) |
C17—N18—N19—N20 | −0.49 (16) | C10—C11—C12—C13 | 0.1 (3) |
N19—N18—C17—C16 | −177.60 (13) | C11—C12—C13—C14 | −0.1 (3) |
N19—N18—C17—C21 | 0.09 (18) | C12—C13—C14—C15 | 0.9 (3) |
N18—N19—N20—C21 | 0.74 (16) | C13—C14—C15—N1 | 174.92 (15) |
N18—N19—N20—C22 | −178.99 (12) | C13—C14—C15—C10 | −1.6 (2) |
N19—N20—C21—C17 | −0.66 (16) | N1—C16—C17—N18 | −173.67 (13) |
C22—N20—C21—C17 | 179.03 (14) | N1—C16—C17—C21 | 9.1 (2) |
N19—N20—C22—C23 | −45.0 (2) | N18—C17—C21—N20 | 0.35 (16) |
N19—N20—C22—C27 | 134.51 (15) | C16—C17—C21—N20 | 177.85 (14) |
C21—N20—C22—C23 | 135.31 (16) | N20—C22—C23—C24 | 179.84 (14) |
C21—N20—C22—C27 | −45.2 (2) | C27—C22—C23—C24 | 0.3 (2) |
N1—C2—C3—C4 | −175.61 (15) | N20—C22—C27—Cl28 | −2.5 (2) |
C7—C2—C3—C4 | 0.1 (2) | N20—C22—C27—C26 | 178.54 (14) |
N1—C2—C7—C6 | 174.54 (14) | C23—C22—C27—Cl28 | 177.04 (12) |
N1—C2—C7—C8 | −5.8 (2) | C23—C22—C27—C26 | −1.9 (2) |
C3—C2—C7—C6 | −1.2 (2) | C22—C23—C24—C25 | 1.2 (2) |
C3—C2—C7—C8 | 178.41 (15) | C23—C24—C25—Cl29 | 178.38 (13) |
C2—C3—C4—C5 | 0.6 (3) | C23—C24—C25—C26 | −1.2 (2) |
C3—C4—C5—C6 | 0.0 (2) | Cl29—C25—C26—C27 | −180.00 (13) |
C4—C5—C6—C7 | −1.2 (3) | C24—C25—C26—C27 | −0.5 (2) |
C5—C6—C7—C2 | 1.8 (2) | C25—C26—C27—Cl28 | −177.01 (12) |
C5—C6—C7—C8 | −177.82 (16) | C25—C26—C27—C22 | 2.0 (2) |
C2—C7—C8—C9 | −33.4 (3) |
Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) x+1/2, −y+3/2, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+3/2, y−1/2, z; (v) −x+3/2, y+1/2, z; (vi) −x+1, y−1/2, −z+3/2; (vii) x−1/2, y, −z+3/2; (viii) −x+1, y+1/2, −z+3/2; (ix) x+1/2, y, −z+3/2. |