Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806010129/bt2034sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806010129/bt2034Isup2.hkl |
CCDC reference: 604988
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.002 Å
- R factor = 0.038
- wR factor = 0.087
- Data-to-parameter ratio = 20.2
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C9 - C12 .. 8.14 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C13 - C14 .. 15.07 su PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C13
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.78 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - C7 .. 5.39 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C9 - C10 .. 5.48 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 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 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia,1997); software used to prepare material for publication: CrystalStructure.
C15H18Cl2N2O3 | F(000) = 720.00 |
Mr = 345.22 | Dx = 1.297 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: -P 2ybc | Cell parameters from 11821 reflections |
a = 9.700 (4) Å | θ = 3.0–27.6° |
b = 11.068 (4) Å | µ = 0.38 mm−1 |
c = 16.514 (8) Å | T = 298 K |
β = 94.135 (19)° | Platelet, colourless |
V = 1768.2 (13) Å3 | 0.47 × 0.40 × 0.20 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 2237 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.033 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −11→12 |
Tmin = 0.830, Tmax = 0.927 | k = −14→14 |
16776 measured reflections | l = −21→21 |
4042 independent reflections |
Refinement on F2 | w = 1/[0.0002Fo2 + 1.1σ(Fo2)]/(4Fo2) |
R[F2 > 2σ(F2)] = 0.038 | (Δ/σ)max < 0.001 |
wR(F2) = 0.087 | Δρmax = 0.28 e Å−3 |
S = 1.01 | Δρmin = −0.39 e Å−3 |
4042 reflections | Extinction correction: Larson (1970) |
200 parameters | Extinction coefficient: 680 (31) |
H-atom parameters constrained |
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.61000 (5) | 0.34219 (4) | 0.59774 (3) | 0.08260 (17) | |
Cl2 | 0.52794 (6) | 0.80583 (5) | 0.67346 (4) | 0.1122 (2) | |
O1 | 0.94279 (12) | 0.34897 (12) | 0.56869 (8) | 0.0812 (4) | |
O2 | 0.93898 (11) | 0.31647 (9) | 0.43213 (6) | 0.0631 (3) | |
O3 | 0.68748 (14) | 0.85931 (11) | 0.53821 (8) | 0.0896 (4) | |
N1 | 0.79123 (13) | 0.44406 (12) | 0.47346 (8) | 0.0596 (4) | |
N2 | 0.77606 (13) | 0.44566 (12) | 0.38864 (8) | 0.0611 (4) | |
C1 | 0.72188 (14) | 0.53029 (13) | 0.52013 (10) | 0.0551 (4) | |
C2 | 0.64082 (14) | 0.49367 (13) | 0.58086 (10) | 0.0587 (4) | |
C3 | 0.58093 (16) | 0.57965 (16) | 0.62739 (11) | 0.0666 (5) | |
C4 | 0.59967 (17) | 0.69976 (16) | 0.61198 (11) | 0.0677 (5) | |
C5 | 0.67629 (17) | 0.73834 (14) | 0.54864 (10) | 0.0645 (5) | |
C6 | 0.73817 (14) | 0.65100 (14) | 0.50390 (10) | 0.0596 (5) | |
C7 | 0.89451 (18) | 0.36929 (14) | 0.50152 (12) | 0.0612 (5) | |
C8 | 0.86450 (17) | 0.36838 (13) | 0.36800 (10) | 0.0571 (4) | |
C9 | 0.89543 (19) | 0.32991 (14) | 0.28464 (10) | 0.0663 (5) | |
C10 | 0.8707 (2) | 0.19493 (16) | 0.27599 (12) | 0.0889 (7) | |
C11 | 1.0471 (2) | 0.3585 (2) | 0.27323 (13) | 0.1142 (9) | |
C12 | 0.8001 (2) | 0.3975 (2) | 0.22321 (12) | 0.1054 (8) | |
C13 | 0.7536 (2) | 0.90625 (17) | 0.47009 (12) | 0.0838 (7) | |
C14 | 0.6630 (2) | 0.8937 (2) | 0.39353 (14) | 0.1058 (8) | |
C15 | 0.7839 (3) | 1.0369 (2) | 0.49061 (16) | 0.1531 (12) | |
H3 | 0.5277 | 0.5560 | 0.6693 | 0.080* | |
H6 | 0.7918 | 0.6742 | 0.4621 | 0.072* | |
H13 | 0.8406 | 0.8630 | 0.4645 | 0.101* | |
H101 | 0.7786 | 0.1762 | 0.2898 | 0.107* | |
H102 | 0.9361 | 0.1522 | 0.3118 | 0.107* | |
H103 | 0.8817 | 0.1710 | 0.2210 | 0.107* | |
H111 | 1.1053 | 0.3058 | 0.3068 | 0.137* | |
H112 | 1.0651 | 0.3468 | 0.2174 | 0.137* | |
H113 | 1.0662 | 0.4409 | 0.2883 | 0.137* | |
H121 | 0.8180 | 0.3723 | 0.1693 | 0.126* | |
H122 | 0.8164 | 0.4828 | 0.2287 | 0.126* | |
H123 | 0.7057 | 0.3802 | 0.2328 | 0.126* | |
H141 | 0.6565 | 0.8100 | 0.3784 | 0.127* | |
H142 | 0.7017 | 0.9388 | 0.3510 | 0.127* | |
H143 | 0.5725 | 0.9242 | 0.4020 | 0.127* | |
H151 | 0.8271 | 1.0744 | 0.4466 | 0.184* | |
H152 | 0.6992 | 1.0780 | 0.4993 | 0.184* | |
H153 | 0.8448 | 1.0412 | 0.5390 | 0.184* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0747 (3) | 0.0763 (3) | 0.0964 (4) | −0.0096 (2) | 0.0033 (2) | 0.0183 (2) |
Cl2 | 0.1382 (5) | 0.1007 (4) | 0.1061 (4) | 0.0235 (3) | 0.0653 (4) | −0.0047 (3) |
O1 | 0.0749 (8) | 0.1199 (10) | 0.0480 (8) | 0.0260 (7) | −0.0006 (6) | 0.0086 (7) |
O2 | 0.0670 (7) | 0.0722 (7) | 0.0501 (7) | 0.0091 (5) | 0.0050 (5) | 0.0027 (5) |
O3 | 0.1286 (11) | 0.0656 (7) | 0.0801 (9) | 0.0047 (7) | 0.0447 (8) | 0.0019 (6) |
N1 | 0.0655 (8) | 0.0683 (8) | 0.0441 (8) | 0.0081 (6) | −0.0019 (6) | −0.0002 (6) |
N2 | 0.0690 (8) | 0.0662 (8) | 0.0470 (8) | 0.0012 (6) | −0.0022 (6) | 0.0018 (6) |
C1 | 0.0487 (8) | 0.0661 (9) | 0.0497 (9) | 0.0023 (7) | −0.0018 (7) | −0.0010 (7) |
C2 | 0.0479 (8) | 0.0693 (10) | 0.0581 (10) | −0.0039 (7) | −0.0017 (8) | 0.0086 (8) |
C3 | 0.0555 (10) | 0.0837 (11) | 0.0621 (11) | 0.0019 (8) | 0.0148 (8) | 0.0107 (9) |
C4 | 0.0634 (10) | 0.0796 (11) | 0.0619 (11) | 0.0083 (8) | 0.0162 (9) | 0.0006 (9) |
C5 | 0.0689 (10) | 0.0668 (10) | 0.0592 (11) | 0.0015 (8) | 0.0140 (9) | 0.0024 (8) |
C6 | 0.0595 (10) | 0.0709 (10) | 0.0493 (10) | −0.0005 (7) | 0.0099 (8) | 0.0037 (8) |
C7 | 0.0609 (10) | 0.0713 (10) | 0.0514 (11) | 0.0057 (8) | 0.0044 (8) | 0.0027 (9) |
C8 | 0.0635 (10) | 0.0591 (9) | 0.0484 (10) | −0.0053 (8) | 0.0009 (8) | 0.0041 (8) |
C9 | 0.0787 (11) | 0.0749 (11) | 0.0461 (10) | −0.0056 (9) | 0.0093 (9) | 0.0014 (8) |
C10 | 0.1224 (17) | 0.0827 (12) | 0.0633 (13) | 0.0054 (11) | 0.0187 (12) | −0.0129 (10) |
C11 | 0.1025 (16) | 0.162 (2) | 0.0817 (16) | −0.0277 (15) | 0.0336 (13) | −0.0008 (14) |
C12 | 0.157 (2) | 0.1063 (15) | 0.0519 (12) | 0.0141 (14) | −0.0004 (13) | 0.0037 (11) |
C13 | 0.1141 (16) | 0.0715 (11) | 0.0684 (13) | −0.0140 (11) | 0.0238 (12) | −0.0021 (10) |
C14 | 0.1310 (19) | 0.0863 (14) | 0.1028 (18) | −0.0037 (13) | 0.0271 (15) | 0.0119 (13) |
C15 | 0.269 (3) | 0.0887 (16) | 0.108 (2) | −0.0652 (19) | 0.060 (2) | −0.0177 (14) |
Cl1—C2 | 1.7291 (16) | C13—C14 | 1.494 (3) |
Cl2—C4 | 1.7306 (19) | C13—C15 | 1.509 (2) |
O1—C7 | 1.194 (2) | C3—H3 | 0.930 |
O2—C7 | 1.383 (2) | C6—H6 | 0.930 |
O2—C8 | 1.3650 (19) | C10—H101 | 0.960 |
O3—C5 | 1.355 (2) | C10—H102 | 0.960 |
O3—C13 | 1.432 (2) | C10—H103 | 0.960 |
N1—N2 | 1.3980 (18) | C11—H111 | 0.960 |
N1—C1 | 1.426 (2) | C11—H112 | 0.960 |
N1—C7 | 1.355 (2) | C11—H113 | 0.960 |
N2—C8 | 1.275 (2) | C12—H121 | 0.960 |
C1—C2 | 1.379 (2) | C12—H122 | 0.960 |
C1—C6 | 1.374 (2) | C12—H123 | 0.960 |
C2—C3 | 1.378 (2) | C13—H13 | 0.980 |
C3—C4 | 1.368 (2) | C14—H141 | 0.960 |
C4—C5 | 1.393 (2) | C14—H142 | 0.960 |
C5—C6 | 1.380 (2) | C14—H143 | 0.960 |
C8—C9 | 1.492 (2) | C15—H151 | 0.960 |
C9—C10 | 1.518 (2) | C15—H152 | 0.960 |
C9—C11 | 1.530 (2) | C15—H153 | 0.960 |
C9—C12 | 1.520 (2) | ||
O1···N1i | 3.5562 (18) | H102···C11vii | 3.549 |
O1···N2i | 3.5809 (18) | H102···H112vii | 3.415 |
O1···C6i | 3.398 (2) | H102···H113vii | 2.863 |
O1···C10ii | 3.576 (2) | H102···H122vii | 3.156 |
O2···C6i | 3.2519 (17) | H102···H142v | 3.374 |
N1···O1i | 3.5562 (18) | H102···H151v | 2.674 |
N2···O1i | 3.5809 (18) | H103···Cl1iv | 3.214 |
N2···C3iii | 3.465 (2) | H103···O1iv | 2.634 |
C3···N2iii | 3.465 (2) | H103···C11vii | 3.526 |
C6···O1i | 3.398 (2) | H103···H113vii | 2.602 |
C6···O2i | 3.2519 (17) | H111···C3i | 3.402 |
C6···C7i | 3.578 (2) | H111···C4i | 3.072 |
C7···C6i | 3.578 (2) | H111···C5i | 3.114 |
C7···C7i | 3.546 (2) | H111···C6i | 3.409 |
C10···O1iv | 3.576 (2) | H112···O1iv | 3.422 |
Cl1···H101ii | 3.467 | H112···C14vii | 3.358 |
Cl1···H103ii | 3.214 | H112···H13vii | 3.208 |
Cl1···H121ii | 3.280 | H112···H102viii | 3.415 |
Cl1···H123ii | 3.405 | H112···H141vii | 3.252 |
Cl1···H141iii | 3.134 | H112···H142vii | 2.792 |
Cl1···H143iii | 3.438 | H113···O1i | 3.319 |
Cl1···H152v | 3.484 | H113···C2i | 3.519 |
Cl2···H101iii | 3.084 | H113···C10viii | 3.082 |
Cl2···H123iii | 3.503 | H113···H101viii | 3.315 |
Cl2···H143vi | 3.355 | H113···H102viii | 2.863 |
O1···H6i | 2.672 | H113···H103viii | 2.602 |
O1···H13i | 3.223 | H113···H142vii | 3.334 |
O1···H103ii | 2.634 | H121···Cl1iv | 3.280 |
O1···H112ii | 3.422 | H121···O1iv | 3.243 |
O1···H113i | 3.319 | H121···C15ix | 3.113 |
O1···H121ii | 3.243 | H121···H152ix | 3.008 |
O1···H153v | 3.560 | H121···H153ix | 2.387 |
O2···H6i | 3.037 | H122···H102viii | 3.156 |
O2···H13i | 3.302 | H122···H153ix | 3.175 |
O2···H151v | 2.906 | H123···Cl1iv | 3.405 |
N2···H3iii | 3.032 | H123···Cl2iii | 3.503 |
C2···H113i | 3.519 | H123···H3iii | 2.961 |
C3···H111i | 3.402 | H123···H143xii | 3.406 |
C4···H111i | 3.072 | H141···Cl1iii | 3.134 |
C5···H111i | 3.114 | H141···H112viii | 3.252 |
C6···H111i | 3.409 | H142···C10xiii | 3.543 |
C7···H6i | 3.097 | H142···C11viii | 3.414 |
C7···H151v | 3.437 | H142···H3ix | 3.335 |
C8···H151v | 3.531 | H142···H101xiii | 2.932 |
C10···H113vii | 3.082 | H142···H102xiii | 3.374 |
C10···H142v | 3.543 | H142···H112viii | 2.792 |
C10···H151v | 3.172 | H142···H113viii | 3.334 |
C11···H102viii | 3.549 | H143···Cl1iii | 3.438 |
C11···H103viii | 3.526 | H143···Cl2vi | 3.355 |
C11···H142vii | 3.414 | H143···H123xiv | 3.406 |
C12···H153ix | 3.177 | H143···H152vi | 3.197 |
C14···H112viii | 3.358 | H151···O2xiii | 2.906 |
C15···H121x | 3.113 | H151···C7xiii | 3.437 |
H3···N2iii | 3.032 | H151···C8xiii | 3.531 |
H3···H123iii | 2.961 | H151···C10xiii | 3.172 |
H3···H142x | 3.335 | H151···H13xi | 3.513 |
H6···O1i | 2.672 | H151···H101xiii | 2.832 |
H6···O2i | 3.037 | H151···H102xiii | 2.674 |
H6···C7i | 3.097 | H151···H153xi | 3.423 |
H13···O1i | 3.223 | H152···Cl1xiii | 3.484 |
H13···O2i | 3.302 | H152···H121x | 3.008 |
H13···H112viii | 3.208 | H152···H143vi | 3.197 |
H13···H151xi | 3.513 | H153···O1xiii | 3.560 |
H13···H153xi | 3.234 | H153···C12x | 3.177 |
H101···Cl1iv | 3.467 | H153···H13xi | 3.234 |
H101···Cl2iii | 3.084 | H153···H121x | 2.387 |
H101···H113vii | 3.315 | H153···H122x | 3.175 |
H101···H142v | 2.932 | H153···H151xi | 3.423 |
H101···H151v | 2.832 | H153···H153xi | 3.481 |
C7—O2—C8 | 106.60 (12) | C4—C3—H3 | 120.0 |
C5—O3—C13 | 120.18 (14) | C1—C6—H6 | 119.5 |
N2—N1—C1 | 120.90 (12) | C5—C6—H6 | 119.5 |
N2—N1—C7 | 111.85 (13) | C9—C10—H101 | 109.5 |
C1—N1—C7 | 126.16 (14) | C9—C10—H102 | 109.5 |
N1—N2—C8 | 103.60 (12) | C9—C10—H103 | 109.5 |
N1—C1—C2 | 120.83 (13) | H101—C10—H102 | 109.5 |
N1—C1—C6 | 118.69 (14) | H101—C10—H103 | 109.5 |
C2—C1—C6 | 120.48 (14) | H102—C10—H103 | 109.5 |
Cl1—C2—C1 | 121.09 (12) | C9—C11—H111 | 109.5 |
Cl1—C2—C3 | 119.67 (12) | C9—C11—H112 | 109.5 |
C1—C2—C3 | 119.21 (14) | C9—C11—H113 | 109.5 |
C2—C3—C4 | 120.03 (16) | H111—C11—H112 | 109.5 |
Cl2—C4—C3 | 119.05 (14) | H111—C11—H113 | 109.5 |
Cl2—C4—C5 | 119.43 (13) | H112—C11—H113 | 109.5 |
C3—C4—C5 | 121.51 (16) | C9—C12—H121 | 109.5 |
O3—C5—C4 | 116.75 (15) | C9—C12—H122 | 109.5 |
O3—C5—C6 | 125.59 (15) | C9—C12—H123 | 109.5 |
C4—C5—C6 | 117.61 (15) | H121—C12—H122 | 109.5 |
C1—C6—C5 | 121.07 (15) | H121—C12—H123 | 109.5 |
O1—C7—O2 | 124.43 (15) | H122—C12—H123 | 109.5 |
O1—C7—N1 | 131.57 (17) | O3—C13—H13 | 109.5 |
O2—C7—N1 | 104.00 (14) | C14—C13—H13 | 109.5 |
O2—C8—N2 | 113.80 (14) | C15—C13—H13 | 109.5 |
O2—C8—C9 | 117.74 (13) | C13—C14—H141 | 109.5 |
N2—C8—C9 | 128.46 (14) | C13—C14—H142 | 109.5 |
C8—C9—C10 | 109.07 (14) | C13—C14—H143 | 109.5 |
C8—C9—C11 | 108.28 (14) | H141—C14—H142 | 109.5 |
C8—C9—C12 | 108.80 (15) | H141—C14—H143 | 109.5 |
C10—C9—C11 | 109.82 (16) | H142—C14—H143 | 109.5 |
C10—C9—C12 | 109.71 (15) | C13—C15—H151 | 109.5 |
C11—C9—C12 | 111.12 (16) | C13—C15—H152 | 109.5 |
O3—C13—C14 | 111.17 (18) | C13—C15—H153 | 109.5 |
O3—C13—C15 | 105.20 (17) | H151—C15—H152 | 109.5 |
C14—C13—C15 | 111.88 (18) | H151—C15—H153 | 109.5 |
C2—C3—H3 | 120.0 | H152—C15—H153 | 109.5 |
C7—O2—C8—N2 | −1.53 (17) | N1—C1—C2—C3 | 176.79 (13) |
C7—O2—C8—C9 | 178.17 (14) | N1—C1—C6—C5 | −178.30 (13) |
C8—O2—C7—O1 | −176.28 (16) | C2—C1—C6—C5 | 1.2 (2) |
C8—O2—C7—N1 | 3.26 (16) | C6—C1—C2—Cl1 | 175.72 (11) |
C5—O3—C13—C14 | 74.6 (2) | C6—C1—C2—C3 | −2.7 (2) |
C5—O3—C13—C15 | −164.09 (17) | Cl1—C2—C3—C4 | −177.02 (12) |
C13—O3—C5—C4 | −174.29 (16) | C1—C2—C3—C4 | 1.4 (2) |
C13—O3—C5—C6 | 8.2 (2) | C2—C3—C4—Cl2 | −177.91 (12) |
N2—N1—C1—C2 | 127.14 (15) | C2—C3—C4—C5 | 1.4 (2) |
N2—N1—C1—C6 | −53.37 (19) | Cl2—C4—C5—O3 | −1.3 (2) |
C1—N1—N2—C8 | 171.90 (13) | Cl2—C4—C5—C6 | 176.46 (12) |
N2—N1—C7—O1 | 175.51 (18) | C3—C4—C5—O3 | 179.45 (15) |
N2—N1—C7—O2 | −4.00 (17) | C3—C4—C5—C6 | −2.8 (2) |
C7—N1—N2—C8 | 3.12 (17) | O3—C5—C6—C1 | 179.04 (14) |
C1—N1—C7—O1 | 7.4 (3) | C4—C5—C6—C1 | 1.5 (2) |
C1—N1—C7—O2 | −172.06 (13) | O2—C8—C9—C10 | 59.71 (19) |
C7—N1—C1—C2 | −65.8 (2) | O2—C8—C9—C11 | −59.76 (19) |
C7—N1—C1—C6 | 113.70 (18) | O2—C8—C9—C12 | 179.35 (15) |
N1—N2—C8—O2 | −0.89 (17) | N2—C8—C9—C10 | −120.64 (19) |
N1—N2—C8—C9 | 179.45 (15) | N2—C8—C9—C11 | 119.9 (2) |
N1—C1—C2—Cl1 | −4.8 (2) | N2—C8—C9—C12 | −1.0 (2) |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x, −y+1/2, z+1/2; (iii) −x+1, −y+1, −z+1; (iv) x, −y+1/2, z−1/2; (v) x, y−1, z; (vi) −x+1, −y+2, −z+1; (vii) −x+2, y−1/2, −z+1/2; (viii) −x+2, y+1/2, −z+1/2; (ix) x, −y+3/2, z−1/2; (x) x, −y+3/2, z+1/2; (xi) −x+2, −y+2, −z+1; (xii) −x+1, y−1/2, −z+1/2; (xiii) x, y+1, z; (xiv) −x+1, y+1/2, −z+1/2. |
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