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In the title compound, C9H7N5Cl2·1.5C3H7NO, the asymmetric unit consists of two crystallographically independent lamotrigine [systematic name: 3,5-diamino-6-(2,3-dichloro­phenyl)-1,2,4-triazine] and three dimethyl­formamide mol­ecules. In the crystal structure, N—H...N and N—H...O hydrogen bonds lead to the formation of R22(8) and R32(8) motifs.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806039353/is2071sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806039353/is2071Isup2.hkl
Contains datablock I

CCDC reference: 281328

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in solvent or counterion
  • R factor = 0.052
  • wR factor = 0.172
  • Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for O21 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for O31 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N21 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N31 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N11 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 29.00 Perc. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 C3 H7 N O
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 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 0 ALERT type 3 Indicator that the structure quality may be low 8 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXL97.

3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine dimethylformamide sesquisolvate top
Crystal data top
C9H7Cl2N5·1.5C3H7NOZ = 4
Mr = 365.74F(000) = 760
Triclinic, P1Dx = 1.369 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.4444 (13) ÅCell parameters from 5760 reflections
b = 10.9943 (13) Åθ = 2.2–25.8°
c = 16.976 (2) ŵ = 0.38 mm1
α = 83.637 (2)°T = 273 K
β = 74.850 (2)°Block, colorless
γ = 70.582 (2)°0.21 × 0.17 × 0.08 mm
V = 1773.9 (4) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4575 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.028
Graphite monochromatorθmax = 25.0°, θmin = 1.2°
ω scansh = 1212
17267 measured reflectionsk = 1313
6231 independent reflectionsl = 2020
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.105P)2 + 0.2266P]
where P = (Fo2 + 2Fc2)/3
6231 reflections(Δ/σ)max = 0.001
443 parametersΔρmax = 0.31 e Å3
4 restraintsΔρmin = 0.31 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl20.11702 (11)0.98331 (7)0.57951 (5)0.1028 (3)
Cl30.29796 (13)0.97405 (10)0.39984 (5)0.1185 (4)
N10.00301 (19)0.7130 (2)0.67727 (12)0.0600 (5)
N20.08188 (19)0.7184 (2)0.75402 (11)0.0616 (5)
N30.11178 (19)0.7503 (2)0.88869 (12)0.0682 (6)
H3A0.19240.73980.89760.082*
H3B0.08320.76570.92850.082*
N40.09423 (17)0.75930 (19)0.80270 (11)0.0532 (5)
N50.29929 (19)0.7598 (2)0.71463 (12)0.0677 (6)
H5A0.32880.77240.75490.081*
H5B0.35210.75370.66600.081*
C10.2007 (2)0.7257 (2)0.57624 (13)0.0545 (5)
C20.2075 (2)0.8377 (2)0.53270 (14)0.0605 (6)
C30.2849 (3)0.8350 (3)0.45342 (15)0.0703 (7)
C40.3556 (3)0.7193 (3)0.41631 (17)0.0813 (8)
H40.40790.71710.36270.098*
C50.3494 (3)0.6078 (3)0.45765 (18)0.0878 (9)
H50.39660.52920.43220.105*
C60.2729 (3)0.6109 (3)0.53753 (16)0.0740 (7)
H60.27020.53390.56570.089*
C70.1200 (2)0.7294 (2)0.66241 (13)0.0518 (5)
C80.0309 (2)0.7426 (2)0.81293 (13)0.0529 (5)
C90.1727 (2)0.7496 (2)0.72751 (13)0.0506 (5)
Cl2'0.29808 (9)0.55985 (7)1.08410 (4)0.0844 (3)
Cl3'0.14152 (11)0.58499 (10)1.26775 (5)0.1143 (4)
N1'0.51125 (19)0.7865 (2)0.99053 (12)0.0613 (5)
N2'0.59303 (19)0.7732 (2)0.91476 (12)0.0649 (5)
N3'0.61932 (19)0.7484 (2)0.78013 (12)0.0726 (6)
H3'10.70530.74440.77260.087*
H3'20.58750.74220.73940.087*
N4'0.40211 (17)0.77344 (19)0.86265 (11)0.0534 (5)
N5'0.18694 (18)0.8033 (2)0.94783 (12)0.0641 (5)
H5'10.15450.80180.90640.077*
H5'20.13220.81390.99590.077*
C1'0.3003 (2)0.8029 (2)1.09043 (13)0.0537 (5)
C2'0.2587 (2)0.7016 (2)1.13293 (14)0.0592 (6)
C3'0.1928 (3)0.7115 (3)1.21488 (15)0.0716 (7)
C4'0.1666 (3)0.8217 (3)1.25488 (16)0.0815 (9)
H4'0.12210.82801.31010.098*
C5'0.2056 (3)0.9224 (3)1.21395 (18)0.0855 (9)
H5'0.18720.99741.24130.103*
C6'0.2720 (3)0.9135 (3)1.13226 (16)0.0698 (7)
H6'0.29810.98281.10480.084*
C7'0.3803 (2)0.7918 (2)1.00404 (13)0.0522 (5)
C8'0.5364 (2)0.7641 (2)0.85408 (14)0.0546 (5)
C9'0.3215 (2)0.7894 (2)0.93747 (13)0.0503 (5)
O110.7115 (4)0.5954 (3)0.29446 (17)0.1396 (11)
N110.7388 (3)0.5597 (2)0.16278 (16)0.0831 (7)
C110.8293 (6)0.5357 (4)0.0818 (2)0.1354 (17)
H11A0.91440.55290.07970.203*
H11B0.78300.59100.04290.203*
H11C0.85050.44720.06890.203*
C120.7815 (4)0.5747 (3)0.2251 (2)0.0985 (10)
H120.87510.56910.21570.118*
C130.5985 (5)0.5586 (5)0.1736 (3)0.1461 (17)
H13A0.55410.55960.23080.219*
H13B0.60000.48200.15060.219*
H13C0.54720.63320.14670.219*
O210.0961 (2)0.8446 (3)1.04246 (14)0.1048 (7)
N210.2583 (2)0.8948 (2)1.16070 (14)0.0717 (6)
C210.3988 (5)0.9115 (5)1.2077 (3)0.123 (2)0.784 (3)
H21A0.40720.93251.26260.184*0.784 (3)
H21B0.42030.83301.20820.184*0.784 (3)
H21C0.46280.98011.18360.184*0.784 (3)
C220.2176 (4)0.8660 (4)1.0830 (2)0.0773 (10)0.784 (3)
H220.28420.86141.05720.093*0.784 (3)
C230.1569 (5)0.9003 (5)1.2022 (3)0.1045 (14)0.784 (3)
H23A0.20220.92291.25800.157*0.784 (3)
H23B0.11460.96421.17590.157*0.784 (3)
H23C0.08610.81761.20060.157*0.784 (3)
C2110.3596 (15)0.8915 (14)1.1167 (9)0.123*0.216 (3)
H21D0.45030.90881.15350.128*0.216 (3)
H21E0.33240.80771.09420.128*0.216 (3)
H21F0.36290.95561.07340.128*0.216 (3)
C2210.1251 (13)0.8739 (11)1.1167 (5)0.077*0.216 (3)
H2210.05680.88081.14020.082*0.216 (3)
C2310.304 (2)0.938 (2)1.2450 (12)0.105*0.216 (3)
H23D0.40210.94751.26530.176*0.216 (3)
H23E0.28951.01871.24690.176*0.216 (3)
H23F0.25190.87461.27830.176*0.216 (3)
O310.5756 (2)0.7319 (3)0.61727 (14)0.1206 (9)
N310.7487 (3)0.7156 (3)0.50572 (15)0.0856 (7)
C310.6583 (7)0.7811 (6)0.4556 (3)0.134 (2)0.784 (3)
H31A0.71120.78210.40020.201*0.784 (3)
H31B0.61110.86810.47340.201*0.784 (3)
H31C0.59060.73810.45900.201*0.784 (3)
C320.7032 (4)0.7006 (4)0.5839 (2)0.0884 (12)0.784 (3)
H32A0.76750.66560.61590.106*0.784 (3)
C330.8968 (6)0.6773 (5)0.4689 (4)0.152 (3)0.784 (3)
H33A0.91170.69440.41110.228*0.784 (3)
H33B0.93770.58680.47920.228*0.784 (3)
H33C0.93940.72520.49190.228*0.784 (3)
C3110.800 (4)0.713 (3)0.4187 (17)0.134*0.216 (3)
H31D0.72290.74010.39330.254*0.216 (3)
H31E0.85660.62620.40300.254*0.216 (3)
H31F0.85570.76930.40170.254*0.216 (3)
C3210.6115 (9)0.7499 (12)0.5407 (5)0.088*0.216 (3)
H3210.54530.78540.51000.091*0.216 (3)
C3310.836 (2)0.6639 (19)0.5572 (12)0.152*0.216 (3)
H33D0.93170.64420.52650.175*0.216 (3)
H33E0.82000.58630.58290.175*0.216 (3)
H33F0.81840.72490.59820.175*0.216 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl20.1456 (8)0.0689 (5)0.0716 (5)0.0203 (5)0.0029 (5)0.0093 (4)
Cl30.1832 (11)0.1169 (7)0.0633 (5)0.0774 (7)0.0106 (5)0.0138 (5)
N10.0511 (11)0.0804 (14)0.0529 (11)0.0263 (9)0.0109 (9)0.0059 (9)
N20.0500 (10)0.0912 (15)0.0510 (11)0.0327 (10)0.0096 (9)0.0058 (10)
N30.0481 (10)0.1160 (18)0.0462 (11)0.0372 (11)0.0061 (8)0.0019 (11)
N40.0419 (9)0.0733 (12)0.0462 (10)0.0210 (8)0.0106 (8)0.0007 (9)
N50.0488 (10)0.1154 (17)0.0469 (11)0.0386 (11)0.0059 (8)0.0088 (11)
C10.0485 (11)0.0716 (15)0.0470 (12)0.0216 (10)0.0119 (9)0.0074 (11)
C20.0651 (14)0.0700 (15)0.0490 (13)0.0235 (12)0.0127 (11)0.0075 (11)
C30.0809 (17)0.0905 (19)0.0464 (13)0.0376 (15)0.0135 (12)0.0011 (13)
C40.0818 (18)0.113 (2)0.0477 (14)0.0363 (17)0.0003 (13)0.0156 (15)
C50.093 (2)0.086 (2)0.0663 (18)0.0123 (16)0.0018 (15)0.0236 (16)
C60.0844 (18)0.0704 (16)0.0616 (16)0.0220 (14)0.0078 (13)0.0095 (13)
C70.0478 (11)0.0622 (13)0.0466 (12)0.0183 (10)0.0112 (9)0.0034 (10)
C80.0417 (11)0.0646 (14)0.0507 (12)0.0167 (10)0.0106 (9)0.0030 (10)
C90.0449 (11)0.0613 (13)0.0467 (12)0.0190 (10)0.0098 (9)0.0018 (10)
Cl2'0.1135 (6)0.0756 (5)0.0655 (4)0.0369 (4)0.0132 (4)0.0057 (3)
Cl3'0.1249 (7)0.1271 (8)0.0731 (5)0.0465 (6)0.0059 (5)0.0196 (5)
N1'0.0474 (10)0.0854 (14)0.0539 (11)0.0214 (9)0.0134 (9)0.0089 (10)
N2'0.0432 (10)0.0973 (16)0.0569 (12)0.0234 (10)0.0115 (9)0.0104 (11)
N3'0.0432 (10)0.1231 (19)0.0507 (11)0.0269 (11)0.0045 (9)0.0131 (11)
N4'0.0427 (9)0.0736 (12)0.0455 (10)0.0203 (8)0.0099 (8)0.0039 (9)
N5'0.0442 (10)0.1032 (16)0.0468 (11)0.0272 (10)0.0082 (8)0.0040 (10)
C1'0.0455 (11)0.0670 (14)0.0477 (12)0.0116 (10)0.0155 (9)0.0061 (10)
C2'0.0533 (12)0.0725 (15)0.0484 (13)0.0146 (11)0.0118 (10)0.0058 (11)
C3'0.0595 (14)0.0927 (19)0.0508 (14)0.0151 (13)0.0072 (11)0.0027 (13)
C4'0.0737 (17)0.101 (2)0.0465 (14)0.0001 (15)0.0070 (12)0.0124 (15)
C5'0.099 (2)0.083 (2)0.0636 (18)0.0026 (17)0.0248 (16)0.0261 (15)
C6'0.0741 (16)0.0715 (16)0.0612 (15)0.0139 (13)0.0207 (13)0.0096 (12)
C7'0.0459 (11)0.0630 (13)0.0485 (12)0.0155 (10)0.0134 (9)0.0048 (10)
C8'0.0429 (11)0.0686 (14)0.0533 (13)0.0175 (10)0.0117 (10)0.0051 (10)
C9'0.0431 (11)0.0606 (13)0.0472 (12)0.0172 (9)0.0100 (9)0.0015 (10)
O110.219 (3)0.116 (2)0.0731 (16)0.032 (2)0.0406 (19)0.0110 (15)
N110.1011 (18)0.0697 (15)0.0774 (16)0.0126 (13)0.0363 (14)0.0064 (12)
C110.198 (5)0.097 (3)0.087 (3)0.024 (3)0.021 (3)0.011 (2)
C120.125 (3)0.0715 (19)0.102 (3)0.0158 (18)0.052 (2)0.0047 (18)
C130.132 (4)0.128 (4)0.198 (5)0.040 (3)0.075 (4)0.001 (3)
O210.0813 (14)0.147 (2)0.0781 (14)0.0454 (13)0.0165 (11)0.0277 (14)
N210.0663 (13)0.0757 (14)0.0615 (14)0.0169 (10)0.0022 (10)0.0038 (11)
C210.084 (3)0.097 (3)0.125 (4)0.005 (2)0.037 (3)0.020 (3)
C220.067 (2)0.097 (3)0.072 (2)0.0322 (19)0.0143 (18)0.0063 (19)
C230.116 (4)0.118 (4)0.085 (3)0.036 (3)0.029 (3)0.016 (2)
O310.0849 (15)0.198 (3)0.0766 (14)0.0630 (17)0.0176 (12)0.0240 (16)
N310.0909 (17)0.1027 (19)0.0589 (14)0.0420 (14)0.0085 (13)0.0125 (13)
C310.168 (5)0.166 (5)0.087 (3)0.064 (4)0.047 (4)0.006 (3)
C320.074 (2)0.121 (3)0.068 (2)0.036 (2)0.0075 (19)0.001 (2)
C330.116 (4)0.110 (4)0.159 (5)0.024 (3)0.070 (4)0.004 (3)
Geometric parameters (Å, º) top
Cl2—C21.724 (3)C11—H11A0.9600
Cl3—C31.717 (3)C11—H11B0.9600
N1—C71.312 (3)C11—H11C0.9600
N1—N21.343 (3)C12—H120.9300
N2—C81.337 (3)C13—H13A0.9600
N3—C81.336 (3)C13—H13B0.9600
N3—H3A0.8600C13—H13C0.9600
N3—H3B0.8600O21—C221.232 (4)
N4—C91.318 (3)O21—C2211.269 (8)
N4—C81.344 (3)N21—C221.315 (4)
N5—C91.323 (3)N21—C2211.352 (12)
N5—H5A0.8600N21—C231.437 (5)
N5—H5B0.8600N21—C211.437 (4)
C1—C61.373 (3)N21—C2111.458 (15)
C1—C21.377 (3)N21—C2311.46 (2)
C1—C71.482 (3)C21—H21A0.9600
C2—C31.375 (3)C21—H21B0.9600
C3—C41.367 (4)C21—H21C0.9600
C4—C51.356 (4)C22—H220.9300
C4—H40.9300C23—H23A0.9600
C5—C61.380 (4)C23—H23B0.9600
C5—H50.9300C23—H23C0.9600
C6—H60.9300C211—H21D0.9600
C7—C91.424 (3)C211—H21E0.9600
Cl2'—C2'1.723 (3)C211—H21F0.9600
Cl3'—C3'1.730 (3)C221—H2210.9300
N1'—C7'1.309 (3)C231—H23D0.9600
N1'—N2'1.338 (3)C231—H23E0.9600
N2'—C8'1.342 (3)C231—H23F0.9600
N3'—C8'1.318 (3)O31—C321.249 (4)
N3'—H3'10.8600O31—C3211.268 (8)
N3'—H3'20.8600N31—C321.299 (4)
N4'—C9'1.321 (3)N31—C3211.339 (8)
N4'—C8'1.342 (3)N31—C3311.37 (2)
N5'—C9'1.327 (3)N31—C311.402 (6)
N5'—H5'10.8600N31—C3111.43 (3)
N5'—H5'20.8600N31—C331.442 (5)
C1'—C6'1.383 (3)C31—H31A0.9600
C1'—C2'1.389 (3)C31—H31B0.9600
C1'—C7'1.481 (3)C31—H31C0.9600
C2'—C3'1.380 (3)C32—H32A0.9300
C3'—C4'1.368 (4)C33—H33A0.9600
C4'—C5'1.362 (5)C33—H33B0.9600
C4'—H4'0.9300C33—H33C0.9600
C5'—C6'1.377 (4)C311—H31D0.9600
C5'—H5'0.9300C311—H31E0.9600
C6'—H6'0.9300C311—H31F0.9600
C7'—C9'1.427 (3)C321—H3210.9300
O11—C121.214 (4)C331—H33D0.9600
N11—C121.296 (4)C331—H33E0.9600
N11—C131.433 (5)C331—H33F0.9600
N11—C111.445 (5)
C7—N1—N2120.13 (19)C22—N21—C22157.1 (4)
C8—N2—N1117.49 (17)C22—N21—C23119.2 (3)
C8—N3—H3A120.0C221—N21—C2362.2 (5)
C8—N3—H3B120.0C22—N21—C21122.4 (4)
H3A—N3—H3B120.0C221—N21—C21177.7 (6)
C9—N4—C8116.14 (18)C23—N21—C21118.2 (4)
C9—N5—H5A120.0C22—N21—C21159.7 (6)
C9—N5—H5B120.0C221—N21—C211116.7 (7)
H5A—N5—H5B120.0C23—N21—C211178.4 (7)
C6—C1—C2117.7 (2)C21—N21—C21163.0 (6)
C6—C1—C7121.4 (2)C22—N21—C231175.4 (8)
C2—C1—C7120.9 (2)C221—N21—C231122.2 (10)
C3—C2—C1121.3 (2)C23—N21—C23160.4 (9)
C3—C2—Cl2119.9 (2)C21—N21—C23158.6 (9)
C1—C2—Cl2118.78 (18)C211—N21—C231120.5 (11)
C4—C3—C2119.7 (3)N21—C21—H21A109.5
C4—C3—Cl3118.8 (2)N21—C21—H21B109.5
C2—C3—Cl3121.5 (2)H21A—C21—H21B109.5
C5—C4—C3120.1 (2)N21—C21—H21C109.5
C5—C4—H4120.0H21A—C21—H21C109.5
C3—C4—H4120.0H21B—C21—H21C109.5
C4—C5—C6120.0 (3)O21—C22—N21123.7 (3)
C4—C5—H5120.0O21—C22—H22118.2
C6—C5—H5120.0N21—C22—H22118.2
C1—C6—C5121.2 (3)N21—C23—H23A109.5
C1—C6—H6119.4N21—C23—H23B109.5
C5—C6—H6119.4H23A—C23—H23B109.5
N1—C7—C9120.46 (19)N21—C23—H23C109.5
N1—C7—C1117.62 (19)H23A—C23—H23C109.5
C9—C7—C1121.92 (19)H23B—C23—H23C109.5
N3—C8—N2116.78 (19)N21—C211—H21D109.5
N3—C8—N4117.4 (2)N21—C211—H21E109.5
N2—C8—N4125.9 (2)H21D—C211—H21E109.5
N4—C9—N5118.6 (2)N21—C211—H21F109.5
N4—C9—C7119.82 (18)H21D—C211—H21F109.5
N5—C9—C7121.6 (2)H21E—C211—H21F109.5
C7'—N1'—N2'120.54 (19)O21—C221—N21118.0 (9)
N1'—N2'—C8'117.71 (17)O21—C221—H221121.0
C8'—N3'—H3'1120.0N21—C221—H221121.0
C8'—N3'—H3'2120.0N21—C231—H23D109.5
H3'1—N3'—H3'2120.0N21—C231—H23E109.5
C9'—N4'—C8'116.59 (18)H23D—C231—H23E109.5
C9'—N5'—H5'1120.0N21—C231—H23F109.5
C9'—N5'—H5'2120.0H23D—C231—H23F109.5
H5'1—N5'—H5'2120.0H23E—C231—H23F109.5
C6'—C1'—C2'118.2 (2)C32—O31—C32162.1 (5)
C6'—C1'—C7'120.1 (2)C32—N31—C32158.9 (5)
C2'—C1'—C7'121.7 (2)C32—N31—C33157.1 (9)
C3'—C2'—C1'120.4 (2)C321—N31—C331116.0 (10)
C3'—C2'—Cl2'119.9 (2)C32—N31—C31121.8 (4)
C1'—C2'—Cl2'119.58 (18)C321—N31—C3163.3 (5)
C4'—C3'—C2'120.2 (3)C331—N31—C31174.0 (9)
C4'—C3'—Cl3'119.4 (2)C32—N31—C311171.5 (12)
C2'—C3'—Cl3'120.3 (2)C321—N31—C311121.5 (15)
C5'—C4'—C3'120.1 (2)C331—N31—C311121.6 (16)
C5'—C4'—H4'120.0C31—N31—C31160.4 (13)
C3'—C4'—H4'120.0C32—N31—C33120.5 (4)
C4'—C5'—C6'120.2 (3)C321—N31—C33179.2 (6)
C4'—C5'—H5'119.9C331—N31—C3363.3 (9)
C6'—C5'—H5'119.9C31—N31—C33117.4 (4)
C5'—C6'—C1'120.9 (3)C311—N31—C3359.0 (13)
C5'—C6'—H6'119.6N31—C31—H31A109.5
C1'—C6'—H6'119.6N31—C31—H31B109.5
N1'—C7'—C9'120.2 (2)H31A—C31—H31B109.5
N1'—C7'—C1'116.08 (19)N31—C31—H31C109.5
C9'—C7'—C1'123.72 (18)H31A—C31—H31C109.5
N3'—C8'—N2'116.83 (19)H31B—C31—H31C109.5
N3'—C8'—N4'118.0 (2)O31—C32—N31121.8 (4)
N2'—C8'—N4'125.2 (2)O31—C32—H32A119.1
N4'—C9'—N5'118.20 (19)N31—C32—H32A119.1
N4'—C9'—C7'119.62 (18)N31—C33—H33A109.5
N5'—C9'—C7'122.18 (19)N31—C33—H33B109.5
C12—N11—C13119.9 (4)H33A—C33—H33B109.5
C12—N11—C11123.0 (4)N31—C33—H33C109.5
C13—N11—C11117.0 (4)H33A—C33—H33C109.5
N11—C11—H11A109.5H33B—C33—H33C109.5
N11—C11—H11B109.5N31—C311—H31D109.5
H11A—C11—H11B109.5N31—C311—H31E109.5
N11—C11—H11C109.5H31D—C311—H31E109.5
H11A—C11—H11C109.5N31—C311—H31F109.5
H11B—C11—H11C109.5H31D—C311—H31F109.5
O11—C12—N11126.5 (4)H31E—C311—H31F109.5
O11—C12—H12116.8O31—C321—N31117.3 (8)
N11—C12—H12116.8O31—C321—H321121.4
N11—C13—H13A109.5N31—C321—H321121.4
N11—C13—H13B109.5N31—C331—H33D109.5
H13A—C13—H13B109.5N31—C331—H33E109.5
N11—C13—H13C109.5H33D—C331—H33E109.5
H13A—C13—H13C109.5N31—C331—H33F109.5
H13B—C13—H13C109.5H33D—C331—H33F109.5
C22—O21—C22161.2 (6)H33E—C331—H33F109.5
C7—N1—N2—C81.0 (3)C3'—C4'—C5'—C6'0.3 (4)
C6—C1—C2—C30.6 (4)C4'—C5'—C6'—C1'0.0 (4)
C7—C1—C2—C3178.3 (2)C2'—C1'—C6'—C5'0.6 (4)
C6—C1—C2—Cl2179.62 (19)C7'—C1'—C6'—C5'175.9 (2)
C7—C1—C2—Cl21.4 (3)N2'—N1'—C7'—C9'2.9 (3)
C1—C2—C3—C40.8 (4)N2'—N1'—C7'—C1'178.3 (2)
Cl2—C2—C3—C4179.5 (2)C6'—C1'—C7'—N1'66.8 (3)
C1—C2—C3—Cl3178.05 (19)C2'—C1'—C7'—N1'109.6 (3)
Cl2—C2—C3—Cl31.7 (3)C6'—C1'—C7'—C9'111.9 (3)
C2—C3—C4—C50.1 (4)C2'—C1'—C7'—C9'71.7 (3)
Cl3—C3—C4—C5178.7 (3)N1'—N2'—C8'—N3'178.7 (2)
C3—C4—C5—C60.7 (5)N1'—N2'—C8'—N4'3.3 (4)
C2—C1—C6—C50.2 (4)C9'—N4'—C8'—N3'179.9 (2)
C7—C1—C6—C5179.1 (3)C9'—N4'—C8'—N2'1.9 (3)
C4—C5—C6—C10.8 (5)C8'—N4'—C9'—N5'177.8 (2)
N2—N1—C7—C91.6 (3)C8'—N4'—C9'—C7'1.9 (3)
N2—N1—C7—C1178.5 (2)N1'—C7'—C9'—N4'4.4 (3)
C6—C1—C7—N178.6 (3)C1'—C7'—C9'—N4'177.0 (2)
C2—C1—C7—N1102.5 (3)N1'—C7'—C9'—N5'175.3 (2)
C6—C1—C7—C9101.2 (3)C1'—C7'—C9'—N5'3.3 (4)
C2—C1—C7—C977.7 (3)C13—N11—C12—O114.1 (5)
N1—N2—C8—N3178.6 (2)C11—N11—C12—O11179.8 (4)
N1—N2—C8—N41.7 (4)C221—O21—C22—N211.2 (7)
C9—N4—C8—N3179.2 (2)C221—N21—C22—O211.2 (7)
C9—N4—C8—N20.5 (3)C23—N21—C22—O211.0 (6)
C8—N4—C9—N5177.1 (2)C21—N21—C22—O21176.1 (4)
C8—N4—C9—C73.2 (3)C211—N21—C22—O21177.6 (8)
N1—C7—C9—N43.9 (3)C22—O21—C221—N211.1 (6)
C1—C7—C9—N4176.3 (2)C22—N21—C221—O211.1 (6)
N1—C7—C9—N5176.5 (2)C23—N21—C221—O21176.7 (12)
C1—C7—C9—N53.4 (3)C211—N21—C221—O214.6 (13)
C7'—N1'—N2'—C8'0.7 (3)C231—N21—C221—O21175.8 (11)
C6'—C1'—C2'—C3'0.9 (3)C321—O31—C32—N310.2 (7)
C7'—C1'—C2'—C3'175.5 (2)C321—N31—C32—O310.2 (7)
C6'—C1'—C2'—Cl2'177.48 (18)C331—N31—C32—O31179.5 (11)
C7'—C1'—C2'—Cl2'1.0 (3)C31—N31—C32—O317.5 (7)
C1'—C2'—C3'—C4'0.6 (4)C33—N31—C32—O31179.4 (4)
Cl2'—C2'—C3'—C4'177.2 (2)C32—O31—C321—N310.1 (7)
C1'—C2'—C3'—Cl3'179.80 (18)C32—N31—C321—O310.1 (7)
Cl2'—C2'—C3'—Cl3'3.3 (3)C331—N31—C321—O310.2 (16)
C2'—C3'—C4'—C5'0.0 (4)C31—N31—C321—O31173.2 (13)
Cl3'—C3'—C4'—C5'179.6 (2)C311—N31—C321—O31169.9 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3B···O210.862.162.975 (3)158
N3—H3A···N2i0.862.092.926 (3)163
N5—H5A···N40.862.163.015 (3)171
N5—H5B···O310.862.202.861 (3)133
N3—H31···N2ii0.862.092.944 (3)175
N3—H32···O310.862.132.952 (3)161
N5—H52···O210.862.232.884 (3)133
N5—H51···N40.862.163.011 (3)169
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z.
 

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