In the title compound, C
9H
7N
5Cl
2·1.5C
3H
7NO, 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
CCDC reference: 281328
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean
(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
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
C9H7Cl2N5·1.5C3H7NO | Z = 4 |
Mr = 365.74 | F(000) = 760 |
Triclinic, P1 | Dx = 1.369 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.4444 (13) Å | Cell parameters from 5760 reflections |
b = 10.9943 (13) Å | θ = 2.2–25.8° |
c = 16.976 (2) Å | µ = 0.38 mm−1 |
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 tube | Rint = 0.028 |
Graphite monochromator | θmax = 25.0°, θmin = 1.2° |
ω scans | h = −12→12 |
17267 measured reflections | k = −13→13 |
6231 independent reflections | l = −20→20 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.173 | H-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 parameters | Δρmax = 0.31 e Å−3 |
4 restraints | Δρmin = −0.31 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cl2 | 0.11702 (11) | 0.98331 (7) | 0.57951 (5) | 0.1028 (3) | |
Cl3 | 0.29796 (13) | 0.97405 (10) | 0.39984 (5) | 0.1185 (4) | |
N1 | −0.00301 (19) | 0.7130 (2) | 0.67727 (12) | 0.0600 (5) | |
N2 | −0.08188 (19) | 0.7184 (2) | 0.75402 (11) | 0.0616 (5) | |
N3 | −0.11178 (19) | 0.7503 (2) | 0.88869 (12) | 0.0682 (6) | |
H3A | −0.1924 | 0.7398 | 0.8976 | 0.082* | |
H3B | −0.0832 | 0.7657 | 0.9285 | 0.082* | |
N4 | 0.09423 (17) | 0.75930 (19) | 0.80270 (11) | 0.0532 (5) | |
N5 | 0.29929 (19) | 0.7598 (2) | 0.71463 (12) | 0.0677 (6) | |
H5A | 0.3288 | 0.7724 | 0.7549 | 0.081* | |
H5B | 0.3521 | 0.7537 | 0.6660 | 0.081* | |
C1 | 0.2007 (2) | 0.7257 (2) | 0.57624 (13) | 0.0545 (5) | |
C2 | 0.2075 (2) | 0.8377 (2) | 0.53270 (14) | 0.0605 (6) | |
C3 | 0.2849 (3) | 0.8350 (3) | 0.45342 (15) | 0.0703 (7) | |
C4 | 0.3556 (3) | 0.7193 (3) | 0.41631 (17) | 0.0813 (8) | |
H4 | 0.4079 | 0.7171 | 0.3627 | 0.098* | |
C5 | 0.3494 (3) | 0.6078 (3) | 0.45765 (18) | 0.0878 (9) | |
H5 | 0.3966 | 0.5292 | 0.4322 | 0.105* | |
C6 | 0.2729 (3) | 0.6109 (3) | 0.53753 (16) | 0.0740 (7) | |
H6 | 0.2702 | 0.5339 | 0.5657 | 0.089* | |
C7 | 0.1200 (2) | 0.7294 (2) | 0.66241 (13) | 0.0518 (5) | |
C8 | −0.0309 (2) | 0.7426 (2) | 0.81293 (13) | 0.0529 (5) | |
C9 | 0.1727 (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) | |
H3'1 | 0.7053 | 0.7444 | 0.7726 | 0.087* | |
H3'2 | 0.5875 | 0.7422 | 0.7394 | 0.087* | |
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) | |
H5'1 | 0.1545 | 0.8018 | 0.9064 | 0.077* | |
H5'2 | 0.1322 | 0.8139 | 0.9959 | 0.077* | |
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' | 0.1221 | 0.8280 | 1.3101 | 0.098* | |
C5' | 0.2056 (3) | 0.9224 (3) | 1.21395 (18) | 0.0855 (9) | |
H5' | 0.1872 | 0.9974 | 1.2413 | 0.103* | |
C6' | 0.2720 (3) | 0.9135 (3) | 1.13226 (16) | 0.0698 (7) | |
H6' | 0.2981 | 0.9828 | 1.1048 | 0.084* | |
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) | |
O11 | 0.7115 (4) | 0.5954 (3) | 0.29446 (17) | 0.1396 (11) | |
N11 | 0.7388 (3) | 0.5597 (2) | 0.16278 (16) | 0.0831 (7) | |
C11 | 0.8293 (6) | 0.5357 (4) | 0.0818 (2) | 0.1354 (17) | |
H11A | 0.9144 | 0.5529 | 0.0797 | 0.203* | |
H11B | 0.7830 | 0.5910 | 0.0429 | 0.203* | |
H11C | 0.8505 | 0.4472 | 0.0689 | 0.203* | |
C12 | 0.7815 (4) | 0.5747 (3) | 0.2251 (2) | 0.0985 (10) | |
H12 | 0.8751 | 0.5691 | 0.2157 | 0.118* | |
C13 | 0.5985 (5) | 0.5586 (5) | 0.1736 (3) | 0.1461 (17) | |
H13A | 0.5541 | 0.5596 | 0.2308 | 0.219* | |
H13B | 0.6000 | 0.4820 | 0.1506 | 0.219* | |
H13C | 0.5472 | 0.6332 | 0.1467 | 0.219* | |
O21 | −0.0961 (2) | 0.8446 (3) | 1.04246 (14) | 0.1048 (7) | |
N21 | −0.2583 (2) | 0.8948 (2) | 1.16070 (14) | 0.0717 (6) | |
C21 | −0.3988 (5) | 0.9115 (5) | 1.2077 (3) | 0.123 (2) | 0.784 (3) |
H21A | −0.4072 | 0.9325 | 1.2626 | 0.184* | 0.784 (3) |
H21B | −0.4203 | 0.8330 | 1.2082 | 0.184* | 0.784 (3) |
H21C | −0.4628 | 0.9801 | 1.1836 | 0.184* | 0.784 (3) |
C22 | −0.2176 (4) | 0.8660 (4) | 1.0830 (2) | 0.0773 (10) | 0.784 (3) |
H22 | −0.2842 | 0.8614 | 1.0572 | 0.093* | 0.784 (3) |
C23 | −0.1569 (5) | 0.9003 (5) | 1.2022 (3) | 0.1045 (14) | 0.784 (3) |
H23A | −0.2022 | 0.9229 | 1.2580 | 0.157* | 0.784 (3) |
H23B | −0.1146 | 0.9642 | 1.1759 | 0.157* | 0.784 (3) |
H23C | −0.0861 | 0.8176 | 1.2006 | 0.157* | 0.784 (3) |
C211 | −0.3596 (15) | 0.8915 (14) | 1.1167 (9) | 0.123* | 0.216 (3) |
H21D | −0.4503 | 0.9088 | 1.1535 | 0.128* | 0.216 (3) |
H21E | −0.3324 | 0.8077 | 1.0942 | 0.128* | 0.216 (3) |
H21F | −0.3629 | 0.9556 | 1.0734 | 0.128* | 0.216 (3) |
C221 | −0.1251 (13) | 0.8739 (11) | 1.1167 (5) | 0.077* | 0.216 (3) |
H221 | −0.0568 | 0.8808 | 1.1402 | 0.082* | 0.216 (3) |
C231 | −0.304 (2) | 0.938 (2) | 1.2450 (12) | 0.105* | 0.216 (3) |
H23D | −0.4021 | 0.9475 | 1.2653 | 0.176* | 0.216 (3) |
H23E | −0.2895 | 1.0187 | 1.2469 | 0.176* | 0.216 (3) |
H23F | −0.2519 | 0.8746 | 1.2783 | 0.176* | 0.216 (3) |
O31 | 0.5756 (2) | 0.7319 (3) | 0.61727 (14) | 0.1206 (9) | |
N31 | 0.7487 (3) | 0.7156 (3) | 0.50572 (15) | 0.0856 (7) | |
C31 | 0.6583 (7) | 0.7811 (6) | 0.4556 (3) | 0.134 (2) | 0.784 (3) |
H31A | 0.7112 | 0.7821 | 0.4002 | 0.201* | 0.784 (3) |
H31B | 0.6111 | 0.8681 | 0.4734 | 0.201* | 0.784 (3) |
H31C | 0.5906 | 0.7381 | 0.4590 | 0.201* | 0.784 (3) |
C32 | 0.7032 (4) | 0.7006 (4) | 0.5839 (2) | 0.0884 (12) | 0.784 (3) |
H32A | 0.7675 | 0.6656 | 0.6159 | 0.106* | 0.784 (3) |
C33 | 0.8968 (6) | 0.6773 (5) | 0.4689 (4) | 0.152 (3) | 0.784 (3) |
H33A | 0.9117 | 0.6944 | 0.4111 | 0.228* | 0.784 (3) |
H33B | 0.9377 | 0.5868 | 0.4792 | 0.228* | 0.784 (3) |
H33C | 0.9394 | 0.7252 | 0.4919 | 0.228* | 0.784 (3) |
C311 | 0.800 (4) | 0.713 (3) | 0.4187 (17) | 0.134* | 0.216 (3) |
H31D | 0.7229 | 0.7401 | 0.3933 | 0.254* | 0.216 (3) |
H31E | 0.8566 | 0.6262 | 0.4030 | 0.254* | 0.216 (3) |
H31F | 0.8557 | 0.7693 | 0.4017 | 0.254* | 0.216 (3) |
C321 | 0.6115 (9) | 0.7499 (12) | 0.5407 (5) | 0.088* | 0.216 (3) |
H321 | 0.5453 | 0.7854 | 0.5100 | 0.091* | 0.216 (3) |
C331 | 0.836 (2) | 0.6639 (19) | 0.5572 (12) | 0.152* | 0.216 (3) |
H33D | 0.9317 | 0.6442 | 0.5265 | 0.175* | 0.216 (3) |
H33E | 0.8200 | 0.5863 | 0.5829 | 0.175* | 0.216 (3) |
H33F | 0.8184 | 0.7249 | 0.5982 | 0.175* | 0.216 (3) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl2 | 0.1456 (8) | 0.0689 (5) | 0.0716 (5) | −0.0203 (5) | −0.0029 (5) | −0.0093 (4) |
Cl3 | 0.1832 (11) | 0.1169 (7) | 0.0633 (5) | −0.0774 (7) | −0.0106 (5) | 0.0138 (5) |
N1 | 0.0511 (11) | 0.0804 (14) | 0.0529 (11) | −0.0263 (9) | −0.0109 (9) | −0.0059 (9) |
N2 | 0.0500 (10) | 0.0912 (15) | 0.0510 (11) | −0.0327 (10) | −0.0096 (9) | −0.0058 (10) |
N3 | 0.0481 (10) | 0.1160 (18) | 0.0462 (11) | −0.0372 (11) | −0.0061 (8) | −0.0019 (11) |
N4 | 0.0419 (9) | 0.0733 (12) | 0.0462 (10) | −0.0210 (8) | −0.0106 (8) | −0.0007 (9) |
N5 | 0.0488 (10) | 0.1154 (17) | 0.0469 (11) | −0.0386 (11) | −0.0059 (8) | −0.0088 (11) |
C1 | 0.0485 (11) | 0.0716 (15) | 0.0470 (12) | −0.0216 (10) | −0.0119 (9) | −0.0074 (11) |
C2 | 0.0651 (14) | 0.0700 (15) | 0.0490 (13) | −0.0235 (12) | −0.0127 (11) | −0.0075 (11) |
C3 | 0.0809 (17) | 0.0905 (19) | 0.0464 (13) | −0.0376 (15) | −0.0135 (12) | −0.0011 (13) |
C4 | 0.0818 (18) | 0.113 (2) | 0.0477 (14) | −0.0363 (17) | −0.0003 (13) | −0.0156 (15) |
C5 | 0.093 (2) | 0.086 (2) | 0.0663 (18) | −0.0123 (16) | −0.0018 (15) | −0.0236 (16) |
C6 | 0.0844 (18) | 0.0704 (16) | 0.0616 (16) | −0.0220 (14) | −0.0078 (13) | −0.0095 (13) |
C7 | 0.0478 (11) | 0.0622 (13) | 0.0466 (12) | −0.0183 (10) | −0.0112 (9) | −0.0034 (10) |
C8 | 0.0417 (11) | 0.0646 (14) | 0.0507 (12) | −0.0167 (10) | −0.0106 (9) | 0.0030 (10) |
C9 | 0.0449 (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) |
O11 | 0.219 (3) | 0.116 (2) | 0.0731 (16) | −0.032 (2) | −0.0406 (19) | −0.0110 (15) |
N11 | 0.1011 (18) | 0.0697 (15) | 0.0774 (16) | −0.0126 (13) | −0.0363 (14) | −0.0064 (12) |
C11 | 0.198 (5) | 0.097 (3) | 0.087 (3) | −0.024 (3) | −0.021 (3) | −0.011 (2) |
C12 | 0.125 (3) | 0.0715 (19) | 0.102 (3) | −0.0158 (18) | −0.052 (2) | −0.0047 (18) |
C13 | 0.132 (4) | 0.128 (4) | 0.198 (5) | −0.040 (3) | −0.075 (4) | −0.001 (3) |
O21 | 0.0813 (14) | 0.147 (2) | 0.0781 (14) | −0.0454 (13) | 0.0165 (11) | −0.0277 (14) |
N21 | 0.0663 (13) | 0.0757 (14) | 0.0615 (14) | −0.0169 (10) | −0.0022 (10) | −0.0038 (11) |
C21 | 0.084 (3) | 0.097 (3) | 0.125 (4) | −0.005 (2) | 0.037 (3) | 0.020 (3) |
C22 | 0.067 (2) | 0.097 (3) | 0.072 (2) | −0.0322 (19) | −0.0143 (18) | −0.0063 (19) |
C23 | 0.116 (4) | 0.118 (4) | 0.085 (3) | −0.036 (3) | −0.029 (3) | −0.016 (2) |
O31 | 0.0849 (15) | 0.198 (3) | 0.0766 (14) | −0.0630 (17) | 0.0176 (12) | −0.0240 (16) |
N31 | 0.0909 (17) | 0.1027 (19) | 0.0589 (14) | −0.0420 (14) | 0.0085 (13) | −0.0125 (13) |
C31 | 0.168 (5) | 0.166 (5) | 0.087 (3) | −0.064 (4) | −0.047 (4) | −0.006 (3) |
C32 | 0.074 (2) | 0.121 (3) | 0.068 (2) | −0.036 (2) | −0.0075 (19) | −0.001 (2) |
C33 | 0.116 (4) | 0.110 (4) | 0.159 (5) | −0.024 (3) | 0.070 (4) | 0.004 (3) |
Geometric parameters (Å, º) top
Cl2—C2 | 1.724 (3) | C11—H11A | 0.9600 |
Cl3—C3 | 1.717 (3) | C11—H11B | 0.9600 |
N1—C7 | 1.312 (3) | C11—H11C | 0.9600 |
N1—N2 | 1.343 (3) | C12—H12 | 0.9300 |
N2—C8 | 1.337 (3) | C13—H13A | 0.9600 |
N3—C8 | 1.336 (3) | C13—H13B | 0.9600 |
N3—H3A | 0.8600 | C13—H13C | 0.9600 |
N3—H3B | 0.8600 | O21—C22 | 1.232 (4) |
N4—C9 | 1.318 (3) | O21—C221 | 1.269 (8) |
N4—C8 | 1.344 (3) | N21—C22 | 1.315 (4) |
N5—C9 | 1.323 (3) | N21—C221 | 1.352 (12) |
N5—H5A | 0.8600 | N21—C23 | 1.437 (5) |
N5—H5B | 0.8600 | N21—C21 | 1.437 (4) |
C1—C6 | 1.373 (3) | N21—C211 | 1.458 (15) |
C1—C2 | 1.377 (3) | N21—C231 | 1.46 (2) |
C1—C7 | 1.482 (3) | C21—H21A | 0.9600 |
C2—C3 | 1.375 (3) | C21—H21B | 0.9600 |
C3—C4 | 1.367 (4) | C21—H21C | 0.9600 |
C4—C5 | 1.356 (4) | C22—H22 | 0.9300 |
C4—H4 | 0.9300 | C23—H23A | 0.9600 |
C5—C6 | 1.380 (4) | C23—H23B | 0.9600 |
C5—H5 | 0.9300 | C23—H23C | 0.9600 |
C6—H6 | 0.9300 | C211—H21D | 0.9600 |
C7—C9 | 1.424 (3) | C211—H21E | 0.9600 |
Cl2'—C2' | 1.723 (3) | C211—H21F | 0.9600 |
Cl3'—C3' | 1.730 (3) | C221—H221 | 0.9300 |
N1'—C7' | 1.309 (3) | C231—H23D | 0.9600 |
N1'—N2' | 1.338 (3) | C231—H23E | 0.9600 |
N2'—C8' | 1.342 (3) | C231—H23F | 0.9600 |
N3'—C8' | 1.318 (3) | O31—C32 | 1.249 (4) |
N3'—H3'1 | 0.8600 | O31—C321 | 1.268 (8) |
N3'—H3'2 | 0.8600 | N31—C32 | 1.299 (4) |
N4'—C9' | 1.321 (3) | N31—C321 | 1.339 (8) |
N4'—C8' | 1.342 (3) | N31—C331 | 1.37 (2) |
N5'—C9' | 1.327 (3) | N31—C31 | 1.402 (6) |
N5'—H5'1 | 0.8600 | N31—C311 | 1.43 (3) |
N5'—H5'2 | 0.8600 | N31—C33 | 1.442 (5) |
C1'—C6' | 1.383 (3) | C31—H31A | 0.9600 |
C1'—C2' | 1.389 (3) | C31—H31B | 0.9600 |
C1'—C7' | 1.481 (3) | C31—H31C | 0.9600 |
C2'—C3' | 1.380 (3) | C32—H32A | 0.9300 |
C3'—C4' | 1.368 (4) | C33—H33A | 0.9600 |
C4'—C5' | 1.362 (5) | C33—H33B | 0.9600 |
C4'—H4' | 0.9300 | C33—H33C | 0.9600 |
C5'—C6' | 1.377 (4) | C311—H31D | 0.9600 |
C5'—H5' | 0.9300 | C311—H31E | 0.9600 |
C6'—H6' | 0.9300 | C311—H31F | 0.9600 |
C7'—C9' | 1.427 (3) | C321—H321 | 0.9300 |
O11—C12 | 1.214 (4) | C331—H33D | 0.9600 |
N11—C12 | 1.296 (4) | C331—H33E | 0.9600 |
N11—C13 | 1.433 (5) | C331—H33F | 0.9600 |
N11—C11 | 1.445 (5) | | |
| | | |
C7—N1—N2 | 120.13 (19) | C22—N21—C221 | 57.1 (4) |
C8—N2—N1 | 117.49 (17) | C22—N21—C23 | 119.2 (3) |
C8—N3—H3A | 120.0 | C221—N21—C23 | 62.2 (5) |
C8—N3—H3B | 120.0 | C22—N21—C21 | 122.4 (4) |
H3A—N3—H3B | 120.0 | C221—N21—C21 | 177.7 (6) |
C9—N4—C8 | 116.14 (18) | C23—N21—C21 | 118.2 (4) |
C9—N5—H5A | 120.0 | C22—N21—C211 | 59.7 (6) |
C9—N5—H5B | 120.0 | C221—N21—C211 | 116.7 (7) |
H5A—N5—H5B | 120.0 | C23—N21—C211 | 178.4 (7) |
C6—C1—C2 | 117.7 (2) | C21—N21—C211 | 63.0 (6) |
C6—C1—C7 | 121.4 (2) | C22—N21—C231 | 175.4 (8) |
C2—C1—C7 | 120.9 (2) | C221—N21—C231 | 122.2 (10) |
C3—C2—C1 | 121.3 (2) | C23—N21—C231 | 60.4 (9) |
C3—C2—Cl2 | 119.9 (2) | C21—N21—C231 | 58.6 (9) |
C1—C2—Cl2 | 118.78 (18) | C211—N21—C231 | 120.5 (11) |
C4—C3—C2 | 119.7 (3) | N21—C21—H21A | 109.5 |
C4—C3—Cl3 | 118.8 (2) | N21—C21—H21B | 109.5 |
C2—C3—Cl3 | 121.5 (2) | H21A—C21—H21B | 109.5 |
C5—C4—C3 | 120.1 (2) | N21—C21—H21C | 109.5 |
C5—C4—H4 | 120.0 | H21A—C21—H21C | 109.5 |
C3—C4—H4 | 120.0 | H21B—C21—H21C | 109.5 |
C4—C5—C6 | 120.0 (3) | O21—C22—N21 | 123.7 (3) |
C4—C5—H5 | 120.0 | O21—C22—H22 | 118.2 |
C6—C5—H5 | 120.0 | N21—C22—H22 | 118.2 |
C1—C6—C5 | 121.2 (3) | N21—C23—H23A | 109.5 |
C1—C6—H6 | 119.4 | N21—C23—H23B | 109.5 |
C5—C6—H6 | 119.4 | H23A—C23—H23B | 109.5 |
N1—C7—C9 | 120.46 (19) | N21—C23—H23C | 109.5 |
N1—C7—C1 | 117.62 (19) | H23A—C23—H23C | 109.5 |
C9—C7—C1 | 121.92 (19) | H23B—C23—H23C | 109.5 |
N3—C8—N2 | 116.78 (19) | N21—C211—H21D | 109.5 |
N3—C8—N4 | 117.4 (2) | N21—C211—H21E | 109.5 |
N2—C8—N4 | 125.9 (2) | H21D—C211—H21E | 109.5 |
N4—C9—N5 | 118.6 (2) | N21—C211—H21F | 109.5 |
N4—C9—C7 | 119.82 (18) | H21D—C211—H21F | 109.5 |
N5—C9—C7 | 121.6 (2) | H21E—C211—H21F | 109.5 |
C7'—N1'—N2' | 120.54 (19) | O21—C221—N21 | 118.0 (9) |
N1'—N2'—C8' | 117.71 (17) | O21—C221—H221 | 121.0 |
C8'—N3'—H3'1 | 120.0 | N21—C221—H221 | 121.0 |
C8'—N3'—H3'2 | 120.0 | N21—C231—H23D | 109.5 |
H3'1—N3'—H3'2 | 120.0 | N21—C231—H23E | 109.5 |
C9'—N4'—C8' | 116.59 (18) | H23D—C231—H23E | 109.5 |
C9'—N5'—H5'1 | 120.0 | N21—C231—H23F | 109.5 |
C9'—N5'—H5'2 | 120.0 | H23D—C231—H23F | 109.5 |
H5'1—N5'—H5'2 | 120.0 | H23E—C231—H23F | 109.5 |
C6'—C1'—C2' | 118.2 (2) | C32—O31—C321 | 62.1 (5) |
C6'—C1'—C7' | 120.1 (2) | C32—N31—C321 | 58.9 (5) |
C2'—C1'—C7' | 121.7 (2) | C32—N31—C331 | 57.1 (9) |
C3'—C2'—C1' | 120.4 (2) | C321—N31—C331 | 116.0 (10) |
C3'—C2'—Cl2' | 119.9 (2) | C32—N31—C31 | 121.8 (4) |
C1'—C2'—Cl2' | 119.58 (18) | C321—N31—C31 | 63.3 (5) |
C4'—C3'—C2' | 120.2 (3) | C331—N31—C31 | 174.0 (9) |
C4'—C3'—Cl3' | 119.4 (2) | C32—N31—C311 | 171.5 (12) |
C2'—C3'—Cl3' | 120.3 (2) | C321—N31—C311 | 121.5 (15) |
C5'—C4'—C3' | 120.1 (2) | C331—N31—C311 | 121.6 (16) |
C5'—C4'—H4' | 120.0 | C31—N31—C311 | 60.4 (13) |
C3'—C4'—H4' | 120.0 | C32—N31—C33 | 120.5 (4) |
C4'—C5'—C6' | 120.2 (3) | C321—N31—C33 | 179.2 (6) |
C4'—C5'—H5' | 119.9 | C331—N31—C33 | 63.3 (9) |
C6'—C5'—H5' | 119.9 | C31—N31—C33 | 117.4 (4) |
C5'—C6'—C1' | 120.9 (3) | C311—N31—C33 | 59.0 (13) |
C5'—C6'—H6' | 119.6 | N31—C31—H31A | 109.5 |
C1'—C6'—H6' | 119.6 | N31—C31—H31B | 109.5 |
N1'—C7'—C9' | 120.2 (2) | H31A—C31—H31B | 109.5 |
N1'—C7'—C1' | 116.08 (19) | N31—C31—H31C | 109.5 |
C9'—C7'—C1' | 123.72 (18) | H31A—C31—H31C | 109.5 |
N3'—C8'—N2' | 116.83 (19) | H31B—C31—H31C | 109.5 |
N3'—C8'—N4' | 118.0 (2) | O31—C32—N31 | 121.8 (4) |
N2'—C8'—N4' | 125.2 (2) | O31—C32—H32A | 119.1 |
N4'—C9'—N5' | 118.20 (19) | N31—C32—H32A | 119.1 |
N4'—C9'—C7' | 119.62 (18) | N31—C33—H33A | 109.5 |
N5'—C9'—C7' | 122.18 (19) | N31—C33—H33B | 109.5 |
C12—N11—C13 | 119.9 (4) | H33A—C33—H33B | 109.5 |
C12—N11—C11 | 123.0 (4) | N31—C33—H33C | 109.5 |
C13—N11—C11 | 117.0 (4) | H33A—C33—H33C | 109.5 |
N11—C11—H11A | 109.5 | H33B—C33—H33C | 109.5 |
N11—C11—H11B | 109.5 | N31—C311—H31D | 109.5 |
H11A—C11—H11B | 109.5 | N31—C311—H31E | 109.5 |
N11—C11—H11C | 109.5 | H31D—C311—H31E | 109.5 |
H11A—C11—H11C | 109.5 | N31—C311—H31F | 109.5 |
H11B—C11—H11C | 109.5 | H31D—C311—H31F | 109.5 |
O11—C12—N11 | 126.5 (4) | H31E—C311—H31F | 109.5 |
O11—C12—H12 | 116.8 | O31—C321—N31 | 117.3 (8) |
N11—C12—H12 | 116.8 | O31—C321—H321 | 121.4 |
N11—C13—H13A | 109.5 | N31—C321—H321 | 121.4 |
N11—C13—H13B | 109.5 | N31—C331—H33D | 109.5 |
H13A—C13—H13B | 109.5 | N31—C331—H33E | 109.5 |
N11—C13—H13C | 109.5 | H33D—C331—H33E | 109.5 |
H13A—C13—H13C | 109.5 | N31—C331—H33F | 109.5 |
H13B—C13—H13C | 109.5 | H33D—C331—H33F | 109.5 |
C22—O21—C221 | 61.2 (6) | H33E—C331—H33F | 109.5 |
| | | |
C7—N1—N2—C8 | 1.0 (3) | C3'—C4'—C5'—C6' | −0.3 (4) |
C6—C1—C2—C3 | −0.6 (4) | C4'—C5'—C6'—C1' | 0.0 (4) |
C7—C1—C2—C3 | 178.3 (2) | C2'—C1'—C6'—C5' | 0.6 (4) |
C6—C1—C2—Cl2 | 179.62 (19) | C7'—C1'—C6'—C5' | −175.9 (2) |
C7—C1—C2—Cl2 | −1.4 (3) | N2'—N1'—C7'—C9' | −2.9 (3) |
C1—C2—C3—C4 | 0.8 (4) | N2'—N1'—C7'—C1' | 178.3 (2) |
Cl2—C2—C3—C4 | −179.5 (2) | C6'—C1'—C7'—N1' | 66.8 (3) |
C1—C2—C3—Cl3 | −178.05 (19) | C2'—C1'—C7'—N1' | −109.6 (3) |
Cl2—C2—C3—Cl3 | 1.7 (3) | C6'—C1'—C7'—C9' | −111.9 (3) |
C2—C3—C4—C5 | −0.1 (4) | C2'—C1'—C7'—C9' | 71.7 (3) |
Cl3—C3—C4—C5 | 178.7 (3) | N1'—N2'—C8'—N3' | −178.7 (2) |
C3—C4—C5—C6 | −0.7 (5) | N1'—N2'—C8'—N4' | 3.3 (4) |
C2—C1—C6—C5 | −0.2 (4) | C9'—N4'—C8'—N3' | −179.9 (2) |
C7—C1—C6—C5 | −179.1 (3) | C9'—N4'—C8'—N2' | −1.9 (3) |
C4—C5—C6—C1 | 0.8 (5) | C8'—N4'—C9'—N5' | 177.8 (2) |
N2—N1—C7—C9 | 1.6 (3) | C8'—N4'—C9'—C7' | −1.9 (3) |
N2—N1—C7—C1 | −178.5 (2) | N1'—C7'—C9'—N4' | 4.4 (3) |
C6—C1—C7—N1 | −78.6 (3) | C1'—C7'—C9'—N4' | −177.0 (2) |
C2—C1—C7—N1 | 102.5 (3) | N1'—C7'—C9'—N5' | −175.3 (2) |
C6—C1—C7—C9 | 101.2 (3) | C1'—C7'—C9'—N5' | 3.3 (4) |
C2—C1—C7—C9 | −77.7 (3) | C13—N11—C12—O11 | −4.1 (5) |
N1—N2—C8—N3 | 178.6 (2) | C11—N11—C12—O11 | 179.8 (4) |
N1—N2—C8—N4 | −1.7 (4) | C221—O21—C22—N21 | −1.2 (7) |
C9—N4—C8—N3 | 179.2 (2) | C221—N21—C22—O21 | 1.2 (7) |
C9—N4—C8—N2 | −0.5 (3) | C23—N21—C22—O21 | −1.0 (6) |
C8—N4—C9—N5 | −177.1 (2) | C21—N21—C22—O21 | −176.1 (4) |
C8—N4—C9—C7 | 3.2 (3) | C211—N21—C22—O21 | 177.6 (8) |
N1—C7—C9—N4 | −3.9 (3) | C22—O21—C221—N21 | 1.1 (6) |
C1—C7—C9—N4 | 176.3 (2) | C22—N21—C221—O21 | −1.1 (6) |
N1—C7—C9—N5 | 176.5 (2) | C23—N21—C221—O21 | 176.7 (12) |
C1—C7—C9—N5 | −3.4 (3) | C211—N21—C221—O21 | −4.6 (13) |
C7'—N1'—N2'—C8' | −0.7 (3) | C231—N21—C221—O21 | −175.8 (11) |
C6'—C1'—C2'—C3' | −0.9 (3) | C321—O31—C32—N31 | −0.2 (7) |
C7'—C1'—C2'—C3' | 175.5 (2) | C321—N31—C32—O31 | 0.2 (7) |
C6'—C1'—C2'—Cl2' | −177.48 (18) | C331—N31—C32—O31 | −179.5 (11) |
C7'—C1'—C2'—Cl2' | −1.0 (3) | C31—N31—C32—O31 | 7.5 (7) |
C1'—C2'—C3'—C4' | 0.6 (4) | C33—N31—C32—O31 | −179.4 (4) |
Cl2'—C2'—C3'—C4' | 177.2 (2) | C32—O31—C321—N31 | 0.1 (7) |
C1'—C2'—C3'—Cl3' | −179.80 (18) | C32—N31—C321—O31 | −0.1 (7) |
Cl2'—C2'—C3'—Cl3' | −3.3 (3) | C331—N31—C321—O31 | 0.2 (16) |
C2'—C3'—C4'—C5' | 0.0 (4) | C31—N31—C321—O31 | −173.2 (13) |
Cl3'—C3'—C4'—C5' | −179.6 (2) | C311—N31—C321—O31 | 169.9 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3B···O21 | 0.86 | 2.16 | 2.975 (3) | 158 |
N3—H3A···N2′i | 0.86 | 2.09 | 2.926 (3) | 163 |
N5—H5A···N4′ | 0.86 | 2.16 | 3.015 (3) | 171 |
N5—H5B···O31 | 0.86 | 2.20 | 2.861 (3) | 133 |
N3′—H3′1···N2ii | 0.86 | 2.09 | 2.944 (3) | 175 |
N3′—H3′2···O31 | 0.86 | 2.13 | 2.952 (3) | 161 |
N5′—H5′2···O21 | 0.86 | 2.23 | 2.884 (3) | 133 |
N5′—H5′1···N4 | 0.86 | 2.16 | 3.011 (3) | 169 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z. |