Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806012694/wn2015sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806012694/wn2015Isup2.hkl |
CCDC reference: 608525
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.037
- wR factor = 0.102
- Data-to-parameter ratio = 18.8
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 39 Perc.
Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.757 PLAT230_ALERT_2_C Hirshfeld Test Diff for Cl1 - C1 .. 5.38 su PLAT230_ALERT_2_C Hirshfeld Test Diff for Cl2 - C15 .. 6.06 su PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C20 .. 5.60 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C2 - C3 .. 5.64 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.20 From the CIF: _reflns_number_total 4606 Count of symmetry unique reflns 2688 Completeness (_total/calc) 171.35% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1918 Fraction of Friedel pairs measured 0.714 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
C22H17Cl2NO2 | F(000) = 824 |
Mr = 398.27 | Dx = 1.401 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2564 reflections |
a = 5.6553 (11) Å | θ = 5.0–12.5° |
b = 15.754 (3) Å | µ = 0.36 mm−1 |
c = 21.191 (4) Å | T = 298 K |
V = 1888.0 (6) Å3 | Block, yellow |
Z = 4 | 0.34 × 0.13 × 0.08 mm |
Bruker SMART APEX area-detector diffractometer | 4606 independent reflections |
Radiation source: fine-focus sealed tube | 1774 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.054 |
ω scans | θmax = 28.2°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→7 |
Tmin = 0.941, Tmax = 0.969 | k = −20→20 |
17030 measured reflections | l = −27→27 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[σ2(Fo2) + (0.0544P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.102 | (Δ/σ)max < 0.001 |
S = 0.76 | Δρmax = 0.14 e Å−3 |
4606 reflections | Δρmin = −0.18 e Å−3 |
245 parameters | Extinction correction: SHELXL97 (Sheldrick, 1997a), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0066 (10) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), with 1918 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.01 (7) |
Experimental. The ratio of observed to unique reflections is low (39%), probably due to the poor diffraction quality of the crystal. |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 1.0968 (6) | 0.14064 (16) | −0.00139 (13) | 0.0673 (7) | |
C2 | 0.8826 (6) | 0.10070 (17) | −0.01273 (14) | 0.0732 (8) | |
H2 | 0.8252 | 0.0948 | −0.0536 | 0.088* | |
C3 | 0.7574 (6) | 0.07015 (16) | 0.03763 (13) | 0.0653 (7) | |
H3 | 0.6141 | 0.0428 | 0.0306 | 0.078* | |
C4 | 0.8401 (5) | 0.07916 (15) | 0.09936 (12) | 0.0585 (7) | |
C5 | 1.0550 (5) | 0.11963 (16) | 0.10880 (13) | 0.0641 (7) | |
H5 | 1.1137 | 0.1258 | 0.1495 | 0.077* | |
C6 | 1.1827 (5) | 0.15079 (17) | 0.05831 (13) | 0.0703 (8) | |
H6 | 1.3258 | 0.1784 | 0.0649 | 0.084* | |
C7 | 0.6929 (5) | 0.04654 (17) | 0.15195 (13) | 0.0639 (7) | |
C8 | 0.7561 (5) | 0.06909 (16) | 0.21835 (11) | 0.0646 (7) | |
H8A | 0.7763 | 0.1301 | 0.2211 | 0.078* | |
H8B | 0.9065 | 0.0430 | 0.2287 | 0.078* | |
C9 | 0.5722 (5) | 0.04133 (16) | 0.26742 (12) | 0.0635 (7) | |
H9A | 0.4150 | 0.0564 | 0.2515 | 0.076* | |
C10 | 0.6124 (5) | 0.08820 (16) | 0.32854 (12) | 0.0672 (8) | |
H10A | 0.7602 | 0.0688 | 0.3468 | 0.081* | |
H10B | 0.6295 | 0.1482 | 0.3193 | 0.081* | |
C11 | 0.4196 (5) | 0.07753 (16) | 0.37676 (13) | 0.0621 (7) | |
C12 | 0.4676 (5) | 0.10638 (15) | 0.44257 (13) | 0.0576 (7) | |
C13 | 0.3044 (5) | 0.08878 (16) | 0.48980 (14) | 0.0662 (8) | |
H13 | 0.1671 | 0.0593 | 0.4797 | 0.079* | |
C14 | 0.3414 (5) | 0.11388 (18) | 0.55086 (14) | 0.0727 (9) | |
H14 | 0.2296 | 0.1021 | 0.5818 | 0.087* | |
C15 | 0.5479 (5) | 0.15720 (17) | 0.56613 (12) | 0.0657 (7) | |
C16 | 0.7119 (5) | 0.17494 (18) | 0.52041 (13) | 0.0685 (8) | |
H16 | 0.8489 | 0.2046 | 0.5306 | 0.082* | |
C17 | 0.6728 (5) | 0.14869 (16) | 0.45959 (13) | 0.0629 (7) | |
H17 | 0.7868 | 0.1595 | 0.4290 | 0.076* | |
C18 | 0.5809 (5) | −0.05525 (16) | 0.27675 (11) | 0.0597 (7) | |
C19 | 0.4000 (5) | −0.10674 (19) | 0.25609 (12) | 0.0669 (8) | |
H19 | 0.2680 | −0.0830 | 0.2368 | 0.080* | |
C20 | 0.4144 (6) | −0.1926 (2) | 0.26393 (13) | 0.0781 (9) | |
H20 | 0.2883 | −0.2252 | 0.2496 | 0.094* | |
C21 | 0.7672 (6) | −0.1836 (2) | 0.31066 (13) | 0.0759 (8) | |
H21 | 0.8964 | −0.2093 | 0.3300 | 0.091* | |
C22 | 0.7689 (6) | −0.09574 (18) | 0.30506 (12) | 0.0677 (8) | |
H22 | 0.8961 | −0.0645 | 0.3203 | 0.081* | |
N1 | 0.5945 (6) | −0.23314 (15) | 0.29042 (11) | 0.0793 (7) | |
O1 | 0.5145 (4) | 0.00522 (13) | 0.14023 (9) | 0.0899 (7) | |
O2 | 0.2290 (4) | 0.04825 (14) | 0.36310 (9) | 0.0895 (6) | |
Cl1 | 1.25397 (18) | 0.17991 (6) | −0.06528 (4) | 0.1027 (3) | |
Cl2 | 0.59811 (19) | 0.18941 (6) | 0.64306 (3) | 0.1063 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.075 (2) | 0.0669 (18) | 0.0603 (18) | 0.0027 (17) | 0.0120 (16) | 0.0021 (14) |
C2 | 0.080 (2) | 0.074 (2) | 0.0661 (19) | 0.0041 (18) | −0.0077 (19) | −0.0121 (16) |
C3 | 0.0663 (17) | 0.0625 (17) | 0.0670 (18) | −0.0015 (17) | −0.0028 (17) | −0.0046 (14) |
C4 | 0.0642 (19) | 0.0497 (16) | 0.0617 (17) | 0.0024 (14) | −0.0046 (15) | −0.0018 (13) |
C5 | 0.0616 (18) | 0.0689 (18) | 0.0618 (17) | 0.0010 (17) | −0.0059 (16) | −0.0013 (14) |
C6 | 0.0671 (19) | 0.0725 (19) | 0.0712 (19) | −0.0036 (16) | 0.0000 (17) | −0.0030 (16) |
C7 | 0.0638 (19) | 0.0556 (17) | 0.072 (2) | 0.0026 (16) | −0.0069 (16) | 0.0060 (15) |
C8 | 0.0731 (18) | 0.0548 (16) | 0.0660 (18) | −0.0093 (16) | 0.0052 (17) | −0.0037 (13) |
C9 | 0.0632 (18) | 0.0590 (17) | 0.0683 (17) | −0.0050 (15) | 0.0066 (16) | −0.0055 (14) |
C10 | 0.0735 (19) | 0.0623 (18) | 0.0658 (17) | −0.0077 (16) | 0.0085 (16) | −0.0098 (13) |
C11 | 0.0569 (17) | 0.0554 (17) | 0.0741 (19) | 0.0011 (15) | 0.0064 (17) | −0.0030 (13) |
C12 | 0.0494 (17) | 0.0537 (15) | 0.0696 (18) | 0.0022 (14) | 0.0049 (15) | 0.0024 (14) |
C13 | 0.0501 (17) | 0.0689 (19) | 0.080 (2) | −0.0022 (14) | 0.0126 (16) | 0.0081 (15) |
C14 | 0.065 (2) | 0.082 (2) | 0.071 (2) | 0.0074 (17) | 0.0174 (16) | 0.0153 (16) |
C15 | 0.067 (2) | 0.0726 (18) | 0.0575 (16) | 0.0099 (16) | 0.0027 (16) | 0.0001 (15) |
C16 | 0.0563 (18) | 0.0774 (19) | 0.0718 (19) | −0.0027 (17) | 0.0040 (17) | −0.0029 (15) |
C17 | 0.0544 (18) | 0.0659 (18) | 0.0685 (18) | −0.0008 (15) | 0.0159 (14) | −0.0029 (14) |
C18 | 0.0600 (18) | 0.0603 (18) | 0.0588 (16) | −0.0032 (17) | 0.0019 (16) | −0.0016 (14) |
C19 | 0.0579 (18) | 0.0668 (19) | 0.0760 (19) | −0.0011 (17) | 0.0030 (16) | −0.0009 (15) |
C20 | 0.089 (3) | 0.063 (2) | 0.082 (2) | −0.015 (2) | −0.001 (2) | −0.0044 (17) |
C21 | 0.082 (2) | 0.075 (2) | 0.0704 (18) | 0.005 (2) | −0.0065 (18) | 0.0105 (16) |
C22 | 0.0653 (19) | 0.071 (2) | 0.0668 (17) | −0.0082 (18) | −0.0016 (16) | 0.0008 (14) |
N1 | 0.0918 (19) | 0.0664 (17) | 0.0795 (17) | 0.0027 (19) | −0.0034 (16) | 0.0044 (13) |
O1 | 0.0836 (15) | 0.1023 (16) | 0.0836 (14) | −0.0271 (14) | −0.0169 (12) | 0.0154 (12) |
O2 | 0.0645 (13) | 0.1115 (16) | 0.0926 (15) | −0.0158 (13) | 0.0017 (12) | −0.0268 (12) |
Cl1 | 0.1086 (7) | 0.1230 (7) | 0.0764 (5) | −0.0124 (6) | 0.0195 (5) | 0.0084 (5) |
Cl2 | 0.1061 (7) | 0.1486 (8) | 0.0642 (5) | 0.0105 (7) | −0.0015 (5) | −0.0013 (5) |
C1—C6 | 1.365 (3) | C11—O2 | 1.208 (3) |
C1—C2 | 1.386 (4) | C11—C12 | 1.491 (4) |
C1—Cl1 | 1.734 (3) | C12—C17 | 1.386 (3) |
C2—C3 | 1.368 (4) | C12—C13 | 1.389 (4) |
C2—H2 | 0.9300 | C13—C14 | 1.369 (4) |
C3—C4 | 1.396 (3) | C13—H13 | 0.9300 |
C3—H3 | 0.9300 | C14—C15 | 1.391 (4) |
C4—C5 | 1.387 (4) | C14—H14 | 0.9300 |
C4—C7 | 1.483 (4) | C15—C16 | 1.370 (4) |
C5—C6 | 1.381 (3) | C15—Cl2 | 1.731 (3) |
C5—H5 | 0.9300 | C16—C17 | 1.372 (3) |
C6—H6 | 0.9300 | C16—H16 | 0.9300 |
C7—O1 | 1.226 (3) | C17—H17 | 0.9300 |
C7—C8 | 1.494 (4) | C18—C19 | 1.377 (4) |
C8—C9 | 1.534 (4) | C18—C22 | 1.378 (4) |
C8—H8A | 0.9700 | C19—C20 | 1.365 (4) |
C8—H8B | 0.9700 | C19—H19 | 0.9300 |
C9—C10 | 1.508 (3) | C20—N1 | 1.327 (4) |
C9—C18 | 1.535 (3) | C20—H20 | 0.9300 |
C9—H9A | 0.9800 | C21—N1 | 1.322 (4) |
C10—C11 | 1.504 (4) | C21—C22 | 1.389 (4) |
C10—H10A | 0.9700 | C21—H21 | 0.9300 |
C10—H10B | 0.9700 | C22—H22 | 0.9300 |
C6—C1—C2 | 121.7 (3) | H10A—C10—H10B | 107.5 |
C6—C1—Cl1 | 120.0 (3) | O2—C11—C12 | 120.2 (2) |
C2—C1—Cl1 | 118.3 (2) | O2—C11—C10 | 121.8 (3) |
C3—C2—C1 | 118.5 (3) | C12—C11—C10 | 118.0 (3) |
C3—C2—H2 | 120.8 | C17—C12—C13 | 117.7 (3) |
C1—C2—H2 | 120.8 | C17—C12—C11 | 122.8 (3) |
C2—C3—C4 | 121.4 (3) | C13—C12—C11 | 119.5 (2) |
C2—C3—H3 | 119.3 | C14—C13—C12 | 121.5 (3) |
C4—C3—H3 | 119.3 | C14—C13—H13 | 119.3 |
C5—C4—C3 | 118.4 (3) | C12—C13—H13 | 119.3 |
C5—C4—C7 | 122.9 (3) | C13—C14—C15 | 119.3 (3) |
C3—C4—C7 | 118.7 (3) | C13—C14—H14 | 120.3 |
C6—C5—C4 | 120.6 (3) | C15—C14—H14 | 120.3 |
C6—C5—H5 | 119.7 | C16—C15—C14 | 120.3 (3) |
C4—C5—H5 | 119.7 | C16—C15—Cl2 | 119.7 (2) |
C1—C6—C5 | 119.4 (3) | C14—C15—Cl2 | 120.1 (2) |
C1—C6—H6 | 120.3 | C15—C16—C17 | 119.6 (3) |
C5—C6—H6 | 120.3 | C15—C16—H16 | 120.2 |
O1—C7—C4 | 119.6 (3) | C17—C16—H16 | 120.2 |
O1—C7—C8 | 120.9 (3) | C16—C17—C12 | 121.6 (3) |
C4—C7—C8 | 119.4 (3) | C16—C17—H17 | 119.2 |
C7—C8—C9 | 114.1 (2) | C12—C17—H17 | 119.2 |
C7—C8—H8A | 108.7 | C19—C18—C22 | 116.1 (2) |
C9—C8—H8A | 108.7 | C19—C18—C9 | 121.3 (3) |
C7—C8—H8B | 108.7 | C22—C18—C9 | 122.7 (3) |
C9—C8—H8B | 108.7 | C20—C19—C18 | 120.0 (3) |
H8A—C8—H8B | 107.6 | C20—C19—H19 | 120.0 |
C10—C9—C8 | 109.9 (2) | C18—C19—H19 | 120.0 |
C10—C9—C18 | 111.7 (2) | N1—C20—C19 | 125.1 (3) |
C8—C9—C18 | 110.4 (2) | N1—C20—H20 | 117.5 |
C10—C9—H9A | 108.3 | C19—C20—H20 | 117.5 |
C8—C9—H9A | 108.3 | N1—C21—C22 | 124.5 (3) |
C18—C9—H9A | 108.3 | N1—C21—H21 | 117.8 |
C11—C10—C9 | 114.8 (2) | C22—C21—H21 | 117.8 |
C11—C10—H10A | 108.6 | C18—C22—C21 | 119.6 (3) |
C9—C10—H10A | 108.6 | C18—C22—H22 | 120.2 |
C11—C10—H10B | 108.6 | C21—C22—H22 | 120.2 |
C9—C10—H10B | 108.6 | C21—N1—C20 | 114.8 (3) |
C6—C1—C2—C3 | −0.8 (4) | O2—C11—C12—C13 | 8.8 (4) |
Cl1—C1—C2—C3 | −179.6 (2) | C10—C11—C12—C13 | −172.7 (2) |
C1—C2—C3—C4 | 0.6 (4) | C17—C12—C13—C14 | 1.5 (4) |
C2—C3—C4—C5 | −0.5 (4) | C11—C12—C13—C14 | 179.9 (2) |
C2—C3—C4—C7 | 178.5 (2) | C12—C13—C14—C15 | −0.7 (4) |
C3—C4—C5—C6 | 0.5 (4) | C13—C14—C15—C16 | 0.4 (4) |
C7—C4—C5—C6 | −178.3 (2) | C13—C14—C15—Cl2 | −180.0 (2) |
C2—C1—C6—C5 | 0.9 (4) | C14—C15—C16—C17 | −0.9 (4) |
Cl1—C1—C6—C5 | 179.6 (2) | Cl2—C15—C16—C17 | 179.4 (2) |
C4—C5—C6—C1 | −0.7 (4) | C15—C16—C17—C12 | 1.8 (4) |
C5—C4—C7—O1 | −174.0 (2) | C13—C12—C17—C16 | −2.0 (4) |
C3—C4—C7—O1 | 7.1 (4) | C11—C12—C17—C16 | 179.6 (2) |
C5—C4—C7—C8 | 9.8 (4) | C10—C9—C18—C19 | 127.3 (3) |
C3—C4—C7—C8 | −169.1 (2) | C8—C9—C18—C19 | −110.1 (3) |
O1—C7—C8—C9 | −3.8 (4) | C10—C9—C18—C22 | −53.7 (4) |
C4—C7—C8—C9 | 172.3 (2) | C8—C9—C18—C22 | 68.9 (3) |
C7—C8—C9—C10 | −163.3 (2) | C22—C18—C19—C20 | −0.3 (4) |
C7—C8—C9—C18 | 73.1 (3) | C9—C18—C19—C20 | 178.7 (2) |
C8—C9—C10—C11 | 170.2 (2) | C18—C19—C20—N1 | −0.4 (5) |
C18—C9—C10—C11 | −66.9 (3) | C19—C18—C22—C21 | 0.5 (4) |
C9—C10—C11—O2 | −14.0 (4) | C9—C18—C22—C21 | −178.5 (3) |
C9—C10—C11—C12 | 167.5 (2) | N1—C21—C22—C18 | 0.0 (4) |
O2—C11—C12—C17 | −172.9 (3) | C22—C21—N1—C20 | −0.6 (4) |
C10—C11—C12—C17 | 5.6 (4) | C19—C20—N1—C21 | 0.9 (4) |