Structure Report
NS06252015A
Sample ID: NS06252015A
Crystal Data and Experimental
Experimental. Single green prism-shaped crystals of (NS06252015A) were recrystallised from a mixture of diethyl ether and acetonitrile by vapour diffusion. A suitable crystal (0.48×0.39×0.23 mm) was selected and mounted on a loop with paratone oil on a Bruker APEX-II CCD diffractometer. The crystal was cooled to T = 100(2) K during data collection. The structure was solved with the XT (Sheldrick, 2015) structure solution program, using direct and dual-space solution methods and by using Olex2 (Dolomanov et al., 2009), as the graphical interface. The structure was refined with version of ShelXL-97 (Sheldrick, 2008) using Least Squares minimisation.
Crystal Data. C24H26Cl2CuN4, Mr = 504.93, orthorhombic, Pbcn (No. 60), a = 15.410(3) Å, b = 8.1028(16) Å, c = 17.820(4) Å, a = b = g = 90°, V = 2225.1(8) Å3, T = 100(2) K, Z = 4, Z' = 0.5, m(MoKa) = 1.242, 17050 reflections measured, 3140 unique (Rint#= 0.0343) which were used in all calculations. The final wR2 was 0.1163 (all data) and R1 was 0.0414 (I > 2(I)).
Compound |
NS06252015A |
|
Formula |
C24H26Cl2CuN4 |
|
Dcalc./ g cm-3 |
1.507 |
|
m/mm-1 |
1.242 |
|
Formula Weight |
504.93 |
|
Colour |
green |
|
Shape |
prism |
|
Max Size/mm |
0.48 |
|
Mid Size/mm |
0.39 |
|
Min Size/mm |
0.23 |
|
T/K |
100(2) |
|
Crystal System |
orthorhombic |
|
Space Group |
Pbcn |
|
a/Å |
15.410(3) |
|
b/Å |
8.1028(16) |
|
c/Å |
17.820(4) |
|
α/° |
90 |
|
β/° |
90 |
|
γ/° |
90 |
|
V/Å3 |
2225.1(8) |
|
Z |
4 |
|
Z' |
0.5 |
|
Qmin/° |
2.286 |
|
Qmax/° |
29.695 |
|
Measured Refl. |
17050 |
|
Independent Refl. |
3140 |
|
Reflections Used |
2698 |
|
Rint |
0.0343 |
|
Parameters |
184 |
|
Restraints |
45 |
|
Largest Peak |
0.728 |
|
Deepest Hole |
-0.637 |
|
GooF |
1.064 |
|
wR2 (all data) |
0.1163 |
|
wR2 |
0.1086 |
|
R1 (all data) |
0.0494 |
|
R1 |
0.0414 |
Structure Quality Indicators
|
Refinement: |
Experimental Extended. A green prism-shaped crystal with dimensions 0.48×0.39×0.23 mm was mounted on a loop with paratone oil. Data were collected using a Bruker APEX-II CCD diffractometer equipped with an Oxford Cryosystems low-temperature apparatus operating at T = 100(2) K.
Data were measured using f and w scans scans of 1° per frame for 30 s using MoKa radiation (fine-focus sealed tube, 45 kV, 35 mA). The total number of runs and images was based on the strategy calculation using the program APEX2 (Bruker, 2014). The resolution that was achieved was θ = 29.695°.
Unit cell indexing was performed by using the APEX2 (Bruker, 2014) software and the cell parameters were refined using SAINT (Bruker, V8.34A, 2013) on 5921 reflections, 35% of the observed reflections.
Data reduction was performed using the SAINT (Bruker, V8.34A, 2013) software. The final completeness is 99.6% out to 29.695 in θ. The absorption coefficient (m) of this material is 1.242 mm-1 and the minimum and maximum transmissions are 0.5638 and 0.7459.
The structure was solved with the XT (Sheldrick, 2015) structure solution program, using direct and dual-space solution methods and by using Olex2 (Dolomanov et al., 2009), as the graphical interface and refined by Least Squares using version of ShelXL-97 (Sheldrick, 2008).
The structure solution program confirmed that the space group is Pbcn (# 60). All non-hydrogen atoms were refined anisotropically.
The value of Z' is 0.5. This means that only half of the formula unit is present in the asymmetric unit, with the other atoms are generated by symmetry.
Data Plots: Diffraction Data
Data Plots: Refinement and Data
Reflection Statistics
|
Total reflections (after filtering) |
18365 |
Unique reflections |
3140 |
|
Completeness |
0.995 |
Mean I/s |
25.47 |
|
hklsub>max</sub> collected |
(21, 11, 23) |
hklsub>min</sub> collected |
(-17, -11, -24) |
|
hklmax used |
(21, 11, 24) |
hklmin used |
(0, 0, 0) |
|
Lim dmax collected |
100.0 |
Lim dmin collected |
0.36 |
|
dmax used |
17.82 |
dmin used |
0.72 |
|
Friedel pairs |
3806 |
Friedel pairs merged |
1 |
|
Inconsistent equivalents |
0 |
Rint |
0.0343 |
|
Rsigma |
0.025 |
Intensity transformed |
0 |
|
Omitted reflections |
0 |
Omitted by user (OMIT hkl) |
39 |
|
Multiplicity |
(11691, 3337) |
Maximum mulitplicity |
14 |
|
Removed systematic absences |
1276 |
Filtered off (Shel/OMIT) |
0 |
Images of the Crystal on the Diffractometer
Table 1: Fractional Atomic Coordinates (×10^4) and Equivalent Isotropic Displacement Parameters (Å^2×10^3) for NS06252015A. Ueq is defined as 1/3 of of the trace of the orthogonalised Uij.
|
Atom |
x |
y |
z |
Ueq |
|
Cu1 |
5000 |
2948.9(4) |
7500 |
12.00(12) |
|
Cl1 |
4207.8(3) |
928.9(6) |
8183.6(3) |
19.37(14) |
|
N1 |
3780.4(11) |
3207.0(19) |
6779.5(9) |
12.2(3) |
|
N2 |
4308.9(12) |
4906(2) |
8026.8(10) |
19.9(4) |
|
C5 |
3554.4(12) |
2599(2) |
6080.3(10) |
11.8(3) |
|
C1 |
3158.2(14) |
3914(2) |
7176.4(11) |
15.9(4) |
|
C4 |
2694.2(13) |
2703(2) |
5801.4(11) |
14.5(4) |
|
C7 |
3977.4(14) |
1214(2) |
4937.2(10) |
16.7(4) |
|
C2 |
2292.0(14) |
4071(3) |
6936.7(12) |
18.9(4) |
|
C3 |
2059.8(13) |
3457(3) |
6254.3(12) |
17.8(4) |
|
C6 |
4194.4(13) |
1841(2) |
5627.2(10) |
13.6(4) |
|
C9 |
2498.2(15) |
2051(2) |
5082.5(12) |
18.9(4) |
|
C8 |
3127.5(15) |
1312(3) |
4661.0(11) |
19.6(4) |
|
C10 |
3379.4(15) |
4539(3) |
7949.9(12) |
23.5(4) |
|
C12 |
4521.5(18) |
6423(3) |
7600.2(15) |
27.9(5) |
|
C11 |
4501.5(18) |
5130(3) |
8831.3(14) |
31.3(5) |
Table 2: Anisotropic Displacement Parameters (×10^4) NS06252015A. The anisotropic displacement factor exponent takes the form: -2PI^2[a*^2 × U11 + ... 2hka* × b* × U12]
|
Atom |
U11 |
U22 |
U33 |
U23 |
U13 |
U12 |
|
Cu1 |
16.7(2) |
9.56(17) |
9.73(17) |
0 |
1.65(11) |
0 |
|
Cl1 |
25.4(3) |
21.3(2) |
11.5(2) |
5.46(16) |
-6.22(17) |
-12.56(18) |
|
N1 |
14.6(8) |
11.4(6) |
10.8(7) |
0.1(5) |
1.4(6) |
3.4(6) |
|
N2 |
25.3(9) |
15.9(7) |
18.5(8) |
-8.9(6) |
-3.4(6) |
7.4(6) |
|
C5 |
15.4(9) |
9.9(7) |
10.0(7) |
2.1(6) |
-0.2(6) |
2.1(6) |
|
C1 |
17.7(10) |
16.7(8) |
13.4(8) |
-0.6(7) |
2.7(7) |
5.1(7) |
|
C4 |
13.9(9) |
13.1(8) |
16.5(8) |
2.3(6) |
-2.0(7) |
1.5(6) |
|
C7 |
22.1(10) |
16.6(8) |
11.4(8) |
-0.3(7) |
-2.8(7) |
5.5(7) |
|
C2 |
16.1(10) |
19.6(9) |
21.0(9) |
0.8(7) |
4.8(8) |
5.5(7) |
|
C3 |
11.9(9) |
18.0(8) |
23.5(10) |
4.9(7) |
0.0(7) |
2.8(7) |
|
C6 |
14.4(9) |
15.5(8) |
10.8(8) |
0.5(6) |
-0.6(7) |
3.7(7) |
|
C9 |
18.3(10) |
18.6(8) |
20.0(9) |
1.5(7) |
-6.9(8) |
1.4(7) |
|
C8 |
25.3(11) |
19.0(9) |
14.3(9) |
-1.6(7) |
-7.6(8) |
3.6(8) |
|
C10 |
22.4(10) |
30.4(11) |
17.6(9) |
-9.5(8) |
1.9(8) |
12.5(8) |
|
C12 |
34.9(14) |
11.6(9) |
37.3(12) |
-4.7(8) |
-11.5(10) |
5.4(8) |
|
C11 |
35.9(13) |
35.0(12) |
22.9(10) |
-18.5(9) |
-6.2(9) |
14.2(11) |
Table 3: Bond Lengths in Å for NS06252015A.
|
Atom |
Atom |
Length/Å |
|
Cu1 |
Cl11 |
2.3777(6) |
|
Cu1 |
Cl1 |
2.3777(6) |
|
Cu1 |
N1 |
2.2857(17) |
|
Cu1 |
N11 |
2.2858(17) |
|
Cu1 |
N2 |
2.1284(17) |
|
Cu1 |
N21 |
2.1284(17) |
|
N1 |
C5 |
1.384(2) |
|
N1 |
C1 |
1.322(2) |
|
N2 |
C10 |
1.469(3) |
|
N2 |
C12 |
1.482(3) |
|
N2 |
C11 |
1.475(3) |
|
C5 |
C4 |
1.418(3) |
|
C5 |
C6 |
1.415(3) |
|
C1 |
C2 |
1.407(3) |
|
C1 |
C10 |
1.508(3) |
|
C4 |
C3 |
1.407(3) |
|
C4 |
C9 |
1.418(3) |
|
C7 |
C6 |
1.372(3) |
|
C7 |
C8 |
1.401(3) |
|
C2 |
C3 |
1.362(3) |
|
C9 |
C8 |
1.365(3) |
|
C12 |
C121 |
1.517(6) |
-------•
11-X,+Y,3/2-Z
Table 4: Bond Angles in ° for NS06252015A.
|
Atom |
Atom |
Atom |
Angle/° |
|
Cl1 |
Cu1 |
Cl11 |
92.99(3) |
|
N1 |
Cu1 |
Cl11 |
101.38(4) |
|
N11 |
Cu1 |
Cl11 |
85.90(4) |
|
N1 |
Cu1 |
Cl1 |
85.91(4) |
|
N11 |
Cu1 |
Cl1 |
101.38(4) |
|
N1 |
Cu1 |
N11 |
169.50(8) |
|
N21 |
Cu1 |
Cl11 |
91.72(6) |
|
N2 |
Cu1 |
Cl1 |
91.72(6) |
|
N2 |
Cu1 |
Cl11 |
174.73(5) |
|
N21 |
Cu1 |
Cl1 |
174.73(5) |
|
N2 |
Cu1 |
N11 |
95.48(7) |
|
N21 |
Cu1 |
N1 |
95.48(7) |
|
N2 |
Cu1 |
N1 |
76.59(6) |
|
N21 |
Cu1 |
N11 |
76.60(6) |
|
N21 |
Cu1 |
N2 |
83.67(11) |
|
C5 |
N1 |
Cu1 |
132.83(12) |
|
C1 |
N1 |
Cu1 |
109.60(13) |
|
C1 |
N1 |
C5 |
116.95(17) |
|
C10 |
N2 |
Cu1 |
107.21(12) |
|
C10 |
N2 |
C12 |
109.61(18) |
|
C10 |
N2 |
C11 |
108.16(18) |
|
C12 |
N2 |
Cu1 |
106.32(14) |
|
C11 |
N2 |
Cu1 |
114.82(14) |
|
C11 |
N2 |
C12 |
110.59(19) |
|
N1 |
C5 |
C4 |
121.96(17) |
|
N1 |
C5 |
C6 |
119.51(17) |
|
C6 |
C5 |
C4 |
118.53(17) |
|
N1 |
C1 |
C2 |
124.39(18) |
|
N1 |
C1 |
C10 |
118.08(18) |
|
C2 |
C1 |
C10 |
117.49(17) |
|
C5 |
C4 |
C9 |
119.56(18) |
|
C3 |
C4 |
C5 |
118.31(18) |
|
C3 |
C4 |
C9 |
122.13(19) |
|
C6 |
C7 |
C8 |
121.45(19) |
|
C3 |
C2 |
C1 |
119.16(18) |
|
C2 |
C3 |
C4 |
119.22(19) |
|
C7 |
C6 |
C5 |
120.14(18) |
|
C8 |
C9 |
C4 |
120.6(2) |
|
C9 |
C8 |
C7 |
119.70(18) |
|
N2 |
C10 |
C1 |
111.95(17) |
|
N2 |
C12 |
C121 |
109.61(16) |
-------•
11-X,+Y,3/2-Z
Table 5: Hydrogen Fractional Atomic Coordinates (×10^4) and Equivalent Isotropic Displacement Parameters (Å^2×10^3) for NS06252015A. Ueq is defined as 1/3 of of the trace of the orthogonalised Uij.
|
Atom |
x |
y |
z |
Ueq |
|
H6 |
4781(8) |
1760(40) |
5802(16) |
26(3) |
|
H3 |
1478(8) |
3520(40) |
6066(14) |
26(3) |
|
H7 |
4390(14) |
670(30) |
4620(13) |
26(3) |
|
H9 |
1915(8) |
2100(30) |
4897(15) |
26(3) |
|
H8 |
2972(18) |
810(30) |
4193(9) |
26(3) |
|
H2 |
1891(14) |
4680(30) |
7242(13) |
26(3) |
|
H11A |
5113(8) |
5440(40) |
8907(19) |
34(4) |
|
H12A |
4196(17) |
6460(40) |
7125(9) |
34(4) |
|
H12B |
4340(20) |
7380(30) |
7905(15) |
34(4) |
|
H10A |
3205(18) |
3670(30) |
8306(15) |
17(6) |
|
H11B |
4440(20) |
4090(20) |
9114(15) |
34(4) |
|
H10B |
3050(20) |
5520(40) |
8066(16) |
31(8) |
|
H11C |
4164(16) |
6050(30) |
9044(16) |
34(4) |
Citations
APEX2 suite for crystallographic software, Bruker axs, Madison, WI ().
L. Palatinus and G. Chapuis, Superflip •a computer program for the solution of crystal structures by charge flipping in arbitrary dimensions, J. Appl. Cryst., (2007), 40, 786-790.
O.V. Dolomanov and L.J. Bourhis and R.J. Gildea and J.A.K. Howard and H. Puschmann, Olex2: A complete structure solution, refinement and analysis program, J. Appl. Cryst., (2009), 42, 339-341.
SAINT-8.34A-2013 - Software for the Integration of CCD Detector System Bruker Analytical X-ray Systems, Bruker axs, Madison, WI (2013).
Sheldrick, G.M., A short history of ShelX, Acta Cryst., (2008), A64, 339-341.
Sheldrick, G. M., SHELXT - Integrated space-group and crystal-structure determination, Acta Cryst., (2015). A71, 3-8.
#==============================================================================#
# PLATON/CHECK-(270106) versus check.def version of 310314 for entry: ns0625201
# Data From: NS06252015A.cif •Data Type: CIF Bond Precision C-C = 0.0031 A
#
# Cell 15.410(3) 8.1028(16) 17.820(4) 90 90 90
# WaveLength 0.71073 Volume Reported 2225.1(8) Calculated 2225.1(8)
# SpaceGroup from Symmetry P b c n Hall: -P 2n 2ab
# Reported P b c n -P 2n 2ab
# MoietyFormula C24 H26 Cl2 Cu N4
# Reported C24 H26 Cl2 Cu N4
# SumFormula C24 H26 Cl2 Cu N4
# Reported C24 H26 Cl2 Cu N4
# Mr = 504.94[Calc], 504.93[Rep]
# Dx,gcm-3 = 1.507[Calc], 1.507[Rep]
# Z = 4[Calc], 4[Rep]
# Mu (mm-1) = 1.242[Calc], 1.242[Rep]
# F000 = 1044.0[Calc], 1044.0[Rep] or F000' = 1046.68[Calc]
# Reported T limits: Tmin=0.564 Tmax=0.746 'MULTI-SCAN'
# Calculated T limits: Tmin=0.564 Tmin'=0.559 Tmax=0.750
# Reported Hmax= 21, Kmax= 11, Lmax= 24, Nref= 3140 , Th(max)= 29.69
# Calculated Hmax= 21, Kmax= 11, Lmax= 24, Nref= 3156 , Ratio = 0.99
# rho(min) = -0.64, rho(max) = 0.73 e/Ang^3
# R= 0.0414( 2698), wR2= 0.1163( 3140), S = 1.064, Npar= 184
#===============================================================================
>>> The Following ALERTS were generated <<<
------------------------------------------• Format: alert-number_ALERT_alert-type_alert-level text
_ALERT_3_B Low Bond Precision on C-C Bonds ............... 3.00 Ang.
_ALERT_4_B C-Atom in CIF Coordinate List out of Sequence .. C1 Note
#===============================================================================
_ALERT_4_G Nr. of Refined C-H H-Atoms in Heavy-Atom Struct. 13 Note
_ALERT_1_G Bond Calc 0.96(2), Rep 0.958(8) ...... 3 su-Rat
C7 -H7 1.555 1.555
_ALERT_1_G Bond Calc 0.96(2), Rep 0.959(8) ...... 3 su-Rat
C2 -H2 1.555 1.555
_ALERT_1_G Bond Calc 0.958(19), Rep 0.958(8) ...... 2 su-Rat
C8 -H8 1.555 1.555
_ALERT_1_G Bond Calc 0.985(19), Rep 0.985(8) ...... 2 su-Rat
C12 -H12A 1.555 1.555
_ALERT_1_G Bond Calc 0.99(3), Rep 0.985(8) ...... 4 su-Rat
C12 -H12B 1.555 1.555
_ALERT_1_G Bond Calc 0.99(2), Rep 0.985(8) ...... 3 su-Rat
C11 -H11B 1.555 1.555
_ALERT_1_G Bond Calc 0.99(3), Rep 0.985(8) ...... 4 su-Rat
C11 -H11C 1.555 1.555
_ALERT_4_G CIF Input Record(s) with more than 80 Characters !
#===============================================================================
ALERT_Level and ALERT_Type Summary
==================================
2 ALERT_Level_A = In General: Serious Problem
9 ALERT_Level_C = Check & Explain
7 ALERT_Type_1 CIF Construction/Syntax Error, Inconsistent or Missing Data.
1 ALERT_Type_3 Indicator that the Structure Quality may be Low.
3 ALERT_Type_4 Improvement, Methodology, Query or Suggestion.
#===============================================================================