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The majority of the title mol­ecule, C28H34ClN3O9S, is disordered over two closely spaced sets of sites; the site occupancy of the major component = 0.542 (3). The conformation of each component is approximately U-shaped with the chloro­benzene ring forming the base and the indolinyl and sulfamoyl groups the sides; an intra­molecular C—H...Cl hydrogen bond possibly contributes to the stabilization of the conformation. In the crystal, a corrugated layer structure parallel to the ab plane is formed by C—H...O and C—H...Cl hydrogen bonds together with C—H...π(ring) inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314623006995/tk4094sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314623006995/tk4094Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314623006995/tk4094Isup3.cml
Supplementary material

CCDC reference: 2280340

Key indicators

Structure: I
  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in main residue
  • R factor = 0.056
  • wR factor = 0.154
  • Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C NonSolvent Resd 1 C Ueq(max)/Ueq(min) Range 3.2 Ratio PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00633 Ang. PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 2 Report
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 58 Note PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ... 57 Report PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records 28 Report PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records 2 Report PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records 4 Report PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR Records 2 Report PLAT189_ALERT_3_G A Non-default SAME Restraint Value for First Par 0.0030 Report PLAT189_ALERT_3_G A Non-default SAME Restraint Value for First Par 0.0030 Report PLAT191_ALERT_3_G A Non-default SADI Restraint Value has been used 0.0030 Report PLAT191_ALERT_3_G A Non-default SADI Restraint Value has been used 0.0030 Report PLAT191_ALERT_3_G A Non-default SADI Restraint Value has been used 0.0030 Report PLAT191_ALERT_3_G A Non-default SADI Restraint Value has been used 0.0030 Report PLAT230_ALERT_2_G Hirshfeld Test Diff for N1 --N2 . 11.5 s.u. PLAT301_ALERT_3_G Main Residue Disorder ..............(Resd 1 ) 67% Note PLAT432_ALERT_2_G Short Inter X...Y Contact O5 ..C22 . 2.85 Ang. 1-x,1/2+y,1-z = 2_656 Check PLAT480_ALERT_4_G Long H...A H-Bond Reported H10A ..CL1 . 2.88 Ang. PLAT480_ALERT_4_G Long H...A H-Bond Reported H24A ..CL1 . 2.86 Ang. PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms .... ! Info PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 413 Note PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL 2019/3 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 31 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 10 Info PLAT992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by 2 Check
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 3 ALERT level C = Check. Ensure it is not caused by an omission or oversight 24 ALERT level G = General information/check it is not something unexpected 1 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 10 ALERT type 3 Indicator that the structure quality may be low 8 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX3 (Bruker, 2020); cell refinement: SAINT (Bruker, 2020); data reduction: SAINT (Bruker, 2020); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Diethyl 2,2'-[({2-chloro-5-[(2-ethoxy-2-oxoethyl)(2-methylindolin-1-yl)carbamoyl]phenyl}sulfonyl)azanediyl]diacetate top
Crystal data top
C28H34ClN3O9SF(000) = 656
Mr = 624.09Dx = 1.358 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 10.683 (2) ÅCell parameters from 8512 reflections
b = 11.347 (2) Åθ = 2.4–26.5°
c = 13.203 (3) ŵ = 0.25 mm1
β = 107.491 (3)°T = 150 K
V = 1526.4 (6) Å3Plate, colourless
Z = 20.36 × 0.26 × 0.06 mm
Data collection top
Bruker SMART APEX CCD Diffractometer5986 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.040
φ and ω scansθmax = 28.7°, θmin = 1.6°
Absorption correction: numerical
(SADABS; Krause et al., 2015)
h = 1414
Tmin = 0.92, Tmax = 0.98k = 1515
26691 measured reflectionsl = 1717
7798 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.154 w = 1/[σ2(Fo2) + (0.0951P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
7798 reflectionsΔρmax = 0.67 e Å3
448 parametersΔρmin = 0.45 e Å3
413 restraintsAbsolute structure: Flack x determined using 2312 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: dualAbsolute structure parameter: 0.07 (3)
Special details top

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5 deg. in omega, collected at phi = 0.00, 90.00 and 180.00 deg. and 2 sets of 800 frames, each of width 0.45 deg in phi, collected at omega = -30.00 and 210.00 deg. The scan time was 25 sec/frame.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 1.00 Å). All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. The ethyl 4-chlorobenzyl-N- (2-methylindolin-1-yl)glycinate portion of the molecule is disordered over two partially resolved sites in a 0.542 (3):0.458 (3) ratio. Also, the C23—C24 ethyl group is disordered over two sites in a 0.526 (12):0.474 (12) ratio. The two components of each disorder were refined with restraints that their geometries be comparable.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.60808 (8)0.54611 (11)0.44326 (6)0.0246 (2)
O40.7476 (2)0.5529 (3)0.47429 (18)0.0310 (5)
O50.5355 (3)0.6319 (2)0.4804 (2)0.0342 (7)
O60.6174 (3)0.1476 (3)0.3450 (3)0.0420 (7)
O70.4485 (3)0.2752 (3)0.3126 (2)0.0370 (7)
O80.6303 (3)0.3898 (4)0.6935 (3)0.0494 (8)
O90.4203 (3)0.3672 (3)0.6856 (2)0.0401 (7)
N30.5647 (3)0.4184 (3)0.4747 (3)0.0278 (7)
Cl10.2994 (7)0.5368 (15)0.2927 (7)0.0376 (19)0.542 (3)
O10.7150 (6)0.5773 (6)0.0047 (4)0.0422 (15)0.542 (3)
O20.9930 (6)0.7129 (5)0.1760 (5)0.0367 (12)0.542 (3)
O31.0605 (7)0.6851 (7)0.0338 (5)0.0565 (15)0.542 (3)
N10.8695 (6)0.3963 (4)0.2179 (4)0.0314 (9)0.542 (3)
N20.8544 (5)0.4813 (6)0.1379 (5)0.0395 (13)0.542 (3)
C10.9622 (11)0.4182 (5)0.3174 (6)0.0283 (10)0.542 (3)
C21.0092 (19)0.5264 (5)0.3612 (9)0.0316 (11)0.542 (3)
H20.9822570.5975470.3229250.038*0.542 (3)
C31.0976 (8)0.5272 (8)0.4634 (6)0.0342 (15)0.542 (3)
H31.1345390.5989900.4959180.041*0.542 (3)
C41.1314 (7)0.4175 (8)0.5180 (6)0.0369 (15)0.542 (3)
H41.1894070.4177080.5884560.044*0.542 (3)
C51.0830 (9)0.3126 (8)0.4724 (7)0.0425 (17)0.542 (3)
H51.1086530.2405730.5094590.051*0.542 (3)
C60.9974 (8)0.3133 (6)0.3727 (6)0.0314 (14)0.542 (3)
C70.9270 (9)0.2123 (6)0.3051 (7)0.0381 (14)0.542 (3)
H7A0.8544040.1828720.3303330.046*0.542 (3)
H7B0.9881170.1465560.3055490.046*0.542 (3)
C80.8748 (7)0.2658 (6)0.1947 (6)0.0344 (14)0.542 (3)
H80.9414880.2533570.1564000.041*0.542 (3)
C90.7445 (9)0.2209 (8)0.1255 (7)0.0489 (17)0.542 (3)
H9A0.7188930.2644560.0583590.073*0.542 (3)
H9B0.6778990.2320900.1620470.073*0.542 (3)
H9C0.7518490.1368220.1112420.073*0.542 (3)
C100.9664 (7)0.5244 (8)0.0989 (6)0.0462 (19)0.542 (3)
H10A1.0465230.4850520.1440290.055*0.542 (3)
H10B0.9500320.4917600.0265780.055*0.542 (3)
C111.0005 (8)0.6456 (7)0.0928 (6)0.0353 (15)0.542 (3)
C121.0536 (11)0.8298 (9)0.1908 (8)0.0491 (19)0.542 (3)
H12A0.9993310.8857730.1381730.059*0.542 (3)
H12B1.1419810.8261420.1813130.059*0.542 (3)
C131.0631 (11)0.8686 (9)0.2997 (9)0.056 (2)0.542 (3)
H13A1.1186690.9389050.3173840.084*0.542 (3)
H13B1.1016800.8053860.3500350.084*0.542 (3)
H13C0.9752450.8871580.3040280.084*0.542 (3)
C140.7348 (5)0.5262 (7)0.0897 (4)0.0273 (13)0.542 (3)
C150.6294 (4)0.5271 (5)0.1450 (3)0.0241 (12)0.542 (3)
C160.6595 (4)0.5333 (6)0.2548 (3)0.0229 (12)0.542 (3)
H160.7485230.5352980.2977640.028*0.542 (3)
C170.5593 (5)0.5365 (6)0.30187 (19)0.0211 (11)0.542 (3)
C180.4290 (5)0.5335 (6)0.2390 (3)0.0276 (13)0.542 (3)
C190.3989 (4)0.5273 (6)0.1292 (3)0.0313 (14)0.542 (3)
H190.3099020.5253140.0862370.038*0.542 (3)
C200.4991 (4)0.5242 (5)0.08213 (19)0.0301 (13)0.542 (3)
H200.4785500.5199620.0070360.036*0.542 (3)
Cl1A0.2959 (9)0.5595 (18)0.2923 (8)0.0376 (19)0.458 (3)
O1A0.7240 (7)0.6425 (7)0.0167 (5)0.0422 (15)0.458 (3)
O2A0.9978 (7)0.6768 (6)0.1420 (6)0.0367 (12)0.458 (3)
O3A1.0740 (8)0.6132 (8)0.0093 (6)0.0565 (15)0.458 (3)
N1A0.8383 (6)0.4156 (5)0.2036 (4)0.0314 (9)0.458 (3)
N2A0.8422 (6)0.5135 (6)0.1379 (5)0.0395 (13)0.458 (3)
C1A0.9428 (13)0.4089 (5)0.2993 (7)0.0283 (10)0.458 (3)
C2A1.008 (2)0.5001 (6)0.3632 (11)0.0316 (11)0.458 (3)
H2A0.9929960.5796940.3405410.038*0.458 (3)
C3A1.0957 (10)0.4718 (9)0.4620 (7)0.0342 (15)0.458 (3)
H3A1.1406010.5316750.5093390.041*0.458 (3)
C4A1.1160 (10)0.3498 (9)0.4900 (7)0.0369 (15)0.458 (3)
H4A1.1772430.3290630.5561310.044*0.458 (3)
C5A1.0501 (10)0.2627 (8)0.4244 (8)0.0425 (17)0.458 (3)
H5A1.0625100.1825480.4459580.051*0.458 (3)
C6A0.9667 (9)0.2915 (6)0.3282 (7)0.0314 (14)0.458 (3)
C7A0.8798 (9)0.2147 (6)0.2421 (8)0.0381 (14)0.458 (3)
H7C0.8031120.1857590.2622880.046*0.458 (3)
H7D0.9289450.1463410.2269890.046*0.458 (3)
C8A0.8374 (8)0.2972 (7)0.1472 (7)0.0344 (14)0.458 (3)
H8A0.9059180.2979880.1096350.041*0.458 (3)
C9A0.7047 (9)0.2781 (9)0.0680 (8)0.0489 (17)0.458 (3)
H9D0.6879230.3398640.0136280.073*0.458 (3)
H9E0.6371450.2812230.1043190.073*0.458 (3)
H9F0.7024860.2008560.0343080.073*0.458 (3)
C10A0.9400 (9)0.4912 (8)0.0750 (7)0.0462 (19)0.458 (3)
H10C0.9975410.4240660.1068830.055*0.458 (3)
H10D0.8912100.4700550.0008400.055*0.458 (3)
C11A1.0188 (8)0.5934 (9)0.0752 (7)0.0353 (15)0.458 (3)
C12A1.0608 (11)0.7912 (9)0.1428 (10)0.0491 (19)0.458 (3)
H12C1.0210000.8330330.0749440.059*0.458 (3)
H12D1.1557070.7808180.1524510.059*0.458 (3)
C13A1.0410 (13)0.8592 (10)0.2321 (12)0.056 (2)0.458 (3)
H13D1.0737160.9396320.2306060.084*0.458 (3)
H13E1.0889380.8213640.2992940.084*0.458 (3)
H13F0.9472310.8615750.2256080.084*0.458 (3)
C14A0.7347 (6)0.5776 (9)0.0926 (5)0.0273 (13)0.458 (3)
C15A0.6263 (5)0.5714 (6)0.1452 (3)0.0241 (12)0.458 (3)
C16A0.6562 (5)0.5654 (7)0.2550 (3)0.0229 (12)0.458 (3)
H16A0.7452020.5634970.2980790.028*0.458 (3)
C17A0.5559 (6)0.5623 (8)0.3020 (2)0.0211 (11)0.458 (3)
C18A0.4257 (6)0.5651 (8)0.2390 (4)0.0276 (13)0.458 (3)
C19A0.3958 (4)0.5711 (7)0.1291 (3)0.0313 (14)0.458 (3)
H19A0.3067710.5730590.0860990.038*0.458 (3)
C20A0.4961 (5)0.5743 (7)0.0822 (2)0.0301 (13)0.458 (3)
H20A0.4756410.5783740.0071350.036*0.458 (3)
C210.6376 (4)0.3145 (3)0.4586 (3)0.0301 (8)
H21A0.6592980.2661330.5240550.036*
H21B0.7213460.3409760.4486560.036*
C220.5672 (4)0.2368 (3)0.3654 (3)0.0324 (9)
C230.3658 (10)0.1945 (11)0.2343 (10)0.040 (2)0.526 (12)
H23A0.3558840.1190070.2687140.048*0.526 (12)
H23B0.4066770.1779760.1776900.048*0.526 (12)
C240.2319 (10)0.2520 (12)0.1868 (11)0.058 (2)0.526 (12)
H24A0.2435200.3311570.1612300.088*0.526 (12)
H24B0.1868100.2577100.2412080.088*0.526 (12)
H24C0.1792780.2042170.1273700.088*0.526 (12)
C23A0.3757 (11)0.2112 (15)0.2169 (10)0.040 (2)0.474 (12)
H23C0.4172360.1343340.2117440.048*0.474 (12)
H23D0.3687400.2577690.1520710.048*0.474 (12)
C24A0.2418 (12)0.1949 (14)0.2341 (12)0.058 (2)0.474 (12)
H24D0.2066900.2719340.2453210.088*0.474 (12)
H24E0.2510910.1451210.2966190.088*0.474 (12)
H24F0.1817070.1571560.1714930.088*0.474 (12)
C250.4624 (4)0.4050 (3)0.5260 (3)0.0283 (8)
H25A0.4059250.3372900.4938720.034*
H25B0.4068430.4766230.5129480.034*
C260.5177 (4)0.3856 (4)0.6440 (3)0.0337 (9)
C270.4571 (5)0.3598 (6)0.8008 (4)0.0537 (13)
H27A0.5144940.4267120.8333850.064*
H27B0.5049020.2854210.8257270.064*
C280.3319 (6)0.3635 (6)0.8307 (5)0.0665 (18)
H28A0.2888180.4398910.8102040.100*
H28B0.3519270.3528550.9075600.100*
H28C0.2733080.3003240.7937140.100*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0278 (4)0.0230 (4)0.0258 (4)0.0039 (4)0.0123 (3)0.0033 (4)
O40.0294 (13)0.0345 (13)0.0293 (11)0.0110 (13)0.0093 (10)0.0042 (12)
O50.0490 (18)0.0239 (13)0.0383 (15)0.0003 (12)0.0263 (14)0.0012 (11)
O60.0490 (18)0.0275 (15)0.057 (2)0.0010 (13)0.0278 (15)0.0112 (13)
O70.0382 (17)0.0319 (15)0.0413 (16)0.0013 (12)0.0123 (13)0.0134 (12)
O80.0308 (18)0.079 (3)0.0393 (17)0.0068 (16)0.0117 (14)0.0076 (16)
O90.0353 (17)0.0540 (19)0.0361 (16)0.0125 (14)0.0186 (13)0.0095 (14)
N30.0320 (18)0.0217 (15)0.0363 (17)0.0046 (12)0.0202 (14)0.0060 (13)
Cl10.0236 (5)0.053 (6)0.0403 (5)0.0055 (13)0.0156 (4)0.0047 (14)
O10.037 (2)0.062 (4)0.029 (2)0.000 (3)0.0123 (17)0.004 (2)
O20.0313 (18)0.052 (3)0.034 (3)0.001 (2)0.020 (2)0.000 (2)
O30.052 (3)0.087 (4)0.047 (3)0.003 (3)0.039 (2)0.005 (3)
N10.0309 (10)0.0318 (10)0.0317 (10)0.0006 (4)0.0097 (5)0.0010 (4)
N20.025 (2)0.068 (3)0.0295 (17)0.0047 (19)0.0131 (15)0.008 (2)
C10.018 (3)0.035 (2)0.033 (2)0.0011 (16)0.0099 (19)0.0027 (17)
C20.0267 (19)0.036 (3)0.0322 (18)0.000 (3)0.0094 (16)0.002 (2)
C30.028 (2)0.040 (4)0.036 (2)0.001 (3)0.0118 (18)0.005 (3)
C40.027 (3)0.050 (3)0.033 (3)0.007 (3)0.007 (2)0.004 (2)
C50.038 (3)0.043 (3)0.048 (3)0.009 (3)0.014 (3)0.004 (2)
C60.029 (3)0.033 (3)0.035 (3)0.002 (2)0.013 (3)0.007 (2)
C70.039 (3)0.033 (2)0.044 (3)0.001 (2)0.015 (3)0.007 (3)
C80.031 (3)0.040 (3)0.032 (3)0.005 (2)0.010 (2)0.007 (2)
C90.048 (4)0.049 (4)0.048 (4)0.010 (3)0.012 (3)0.016 (3)
C100.032 (3)0.080 (4)0.028 (3)0.015 (3)0.010 (2)0.020 (3)
C110.031 (3)0.049 (3)0.032 (3)0.016 (2)0.018 (2)0.005 (3)
C120.048 (3)0.058 (3)0.048 (4)0.007 (3)0.024 (3)0.002 (3)
C130.044 (4)0.056 (4)0.066 (5)0.014 (3)0.014 (4)0.010 (4)
C140.0283 (19)0.030 (3)0.0235 (17)0.001 (3)0.0083 (15)0.004 (3)
C150.0245 (18)0.022 (3)0.0281 (16)0.001 (2)0.0110 (14)0.004 (2)
C160.0214 (16)0.021 (3)0.0282 (15)0.002 (2)0.0106 (13)0.003 (2)
C170.0230 (16)0.017 (3)0.0243 (14)0.0040 (19)0.0084 (12)0.0019 (17)
C180.0267 (17)0.025 (3)0.0336 (16)0.004 (2)0.0128 (14)0.002 (2)
C190.0247 (18)0.035 (4)0.0331 (18)0.002 (3)0.0071 (15)0.000 (3)
C200.032 (2)0.032 (3)0.0252 (17)0.001 (3)0.0074 (16)0.002 (3)
Cl1A0.0236 (5)0.053 (6)0.0403 (5)0.0055 (13)0.0156 (4)0.0047 (14)
O1A0.037 (2)0.062 (4)0.029 (2)0.000 (3)0.0123 (17)0.004 (2)
O2A0.0313 (18)0.052 (3)0.034 (3)0.001 (2)0.020 (2)0.000 (2)
O3A0.052 (3)0.087 (4)0.047 (3)0.003 (3)0.039 (2)0.005 (3)
N1A0.0309 (10)0.0318 (10)0.0317 (10)0.0006 (4)0.0097 (5)0.0010 (4)
N2A0.025 (2)0.068 (3)0.0295 (17)0.0047 (19)0.0131 (15)0.008 (2)
C1A0.018 (3)0.035 (2)0.033 (2)0.0011 (16)0.0099 (19)0.0027 (17)
C2A0.0267 (19)0.036 (3)0.0322 (18)0.000 (3)0.0094 (16)0.002 (2)
C3A0.028 (2)0.040 (4)0.036 (2)0.001 (3)0.0118 (18)0.005 (3)
C4A0.027 (3)0.050 (3)0.033 (3)0.007 (3)0.007 (2)0.004 (2)
C5A0.038 (3)0.043 (3)0.048 (3)0.009 (3)0.014 (3)0.004 (2)
C6A0.029 (3)0.033 (3)0.035 (3)0.002 (2)0.013 (3)0.007 (2)
C7A0.039 (3)0.033 (2)0.044 (3)0.001 (2)0.015 (3)0.007 (3)
C8A0.031 (3)0.040 (3)0.032 (3)0.005 (2)0.010 (2)0.007 (2)
C9A0.048 (4)0.049 (4)0.048 (4)0.010 (3)0.012 (3)0.016 (3)
C10A0.032 (3)0.080 (4)0.028 (3)0.015 (3)0.010 (2)0.020 (3)
C11A0.031 (3)0.049 (3)0.032 (3)0.016 (2)0.018 (2)0.005 (3)
C12A0.048 (3)0.058 (3)0.048 (4)0.007 (3)0.024 (3)0.002 (3)
C13A0.044 (4)0.056 (4)0.066 (5)0.014 (3)0.014 (4)0.010 (4)
C14A0.0283 (19)0.030 (3)0.0235 (17)0.001 (3)0.0083 (15)0.004 (3)
C15A0.0245 (18)0.022 (3)0.0281 (16)0.001 (2)0.0110 (14)0.004 (2)
C16A0.0214 (16)0.021 (3)0.0282 (15)0.002 (2)0.0106 (13)0.003 (2)
C17A0.0230 (16)0.017 (3)0.0243 (14)0.0040 (19)0.0084 (12)0.0019 (17)
C18A0.0267 (17)0.025 (3)0.0336 (16)0.004 (2)0.0128 (14)0.002 (2)
C19A0.0247 (18)0.035 (4)0.0331 (18)0.002 (3)0.0071 (15)0.000 (3)
C20A0.032 (2)0.032 (3)0.0252 (17)0.001 (3)0.0074 (16)0.002 (3)
C210.031 (2)0.0236 (17)0.038 (2)0.0001 (14)0.0149 (16)0.0050 (14)
C220.035 (2)0.0268 (18)0.043 (2)0.0036 (15)0.0227 (18)0.0041 (15)
C230.044 (3)0.039 (3)0.038 (3)0.005 (2)0.013 (2)0.010 (3)
C240.041 (3)0.064 (5)0.065 (5)0.004 (4)0.008 (4)0.025 (4)
C23A0.044 (3)0.039 (3)0.038 (3)0.005 (2)0.013 (2)0.010 (3)
C24A0.041 (3)0.064 (5)0.065 (5)0.004 (4)0.008 (4)0.025 (4)
C250.027 (2)0.0231 (18)0.040 (2)0.0057 (14)0.0179 (16)0.0044 (14)
C260.033 (2)0.033 (2)0.040 (2)0.0060 (17)0.0172 (18)0.0073 (16)
C270.055 (3)0.075 (4)0.038 (2)0.025 (3)0.025 (2)0.018 (2)
C280.079 (4)0.083 (4)0.057 (3)0.031 (3)0.049 (3)0.029 (3)
Geometric parameters (Å, º) top
S1—O51.421 (3)N1A—C1A1.414 (7)
S1—O41.424 (3)N1A—N2A1.418 (7)
S1—N31.613 (3)N1A—C8A1.535 (7)
S1—C171.784 (3)N2A—C14A1.339 (7)
S1—C17A1.789 (3)N2A—C10A1.538 (7)
O6—C221.213 (5)C1A—C2A1.382 (7)
O7—C221.324 (5)C1A—C6A1.388 (7)
O7—C23A1.462 (6)C2A—C3A1.397 (7)
O7—C231.462 (6)C2A—H2A0.9500
O8—C261.184 (5)C3A—C4A1.432 (12)
O9—C261.331 (5)C3A—H3A0.9500
O9—C271.454 (6)C4A—C5A1.363 (12)
N3—C251.457 (5)C4A—H4A0.9500
N3—C211.463 (5)C5A—C6A1.355 (11)
Cl1—C181.735 (3)C5A—H5A0.9500
O1—C141.223 (7)C6A—C7A1.510 (10)
O2—C111.361 (9)C7A—C8A1.520 (11)
O2—C121.463 (10)C7A—H7C0.9900
O3—C111.233 (7)C7A—H7D0.9900
N1—N21.403 (6)C8A—C9A1.503 (10)
N1—C11.410 (6)C8A—H8A1.0000
N1—C81.517 (7)C9A—H9D0.9800
N2—C141.344 (7)C9A—H9E0.9800
N2—C101.518 (7)C9A—H9F0.9800
C1—C21.384 (7)C10A—C11A1.433 (11)
C1—C61.388 (7)C10A—H10C0.9900
C2—C31.395 (7)C10A—H10D0.9900
C2—H20.9500C12A—C13A1.475 (12)
C3—C41.429 (11)C12A—H12C0.9900
C3—H30.9500C12A—H12D0.9900
C4—C51.364 (12)C13A—H13D0.9800
C4—H40.9500C13A—H13E0.9800
C5—C61.358 (11)C13A—H13F0.9800
C5—H50.9500C14A—C15A1.520 (5)
C6—C71.508 (10)C15A—C16A1.3900
C7—C81.522 (11)C15A—C20A1.3900
C7—H7A0.9900C16A—C17A1.3900
C7—H7B0.9900C16A—H16A0.9500
C8—C91.505 (10)C17A—C18A1.3900
C8—H81.0000C18A—C19A1.3900
C9—H9A0.9800C19A—C20A1.3900
C9—H9B0.9800C19A—H19A0.9500
C9—H9C0.9800C20A—H20A0.9500
C10—C111.431 (11)C21—C221.517 (5)
C10—H10A0.9900C21—H21A0.9900
C10—H10B0.9900C21—H21B0.9900
C12—C131.478 (12)C23—C241.526 (11)
C12—H12A0.9900C23—H23A0.9900
C12—H12B0.9900C23—H23B0.9900
C13—H13A0.9800C24—H24A0.9800
C13—H13B0.9800C24—H24B0.9800
C13—H13C0.9800C24—H24C0.9800
C14—C151.515 (5)C23A—C24A1.525 (11)
C15—C161.3900C23A—H23C0.9900
C15—C201.3900C23A—H23D0.9900
C16—C171.3900C24A—H24D0.9800
C16—H160.9500C24A—H24E0.9800
C17—C181.3900C24A—H24F0.9800
C18—C191.3900C25—C261.508 (6)
C19—C201.3900C25—H25A0.9900
C19—H190.9500C25—H25B0.9900
C20—H200.9500C27—C281.505 (7)
Cl1A—C18A1.735 (3)C27—H27A0.9900
O1A—C14A1.221 (7)C27—H27B0.9900
O2A—C11A1.357 (9)C28—H28A0.9800
O2A—C12A1.461 (10)C28—H28B0.9800
O3A—C11A1.211 (7)C28—H28C0.9800
O5—S1—O4119.78 (18)C6A—C5A—H5A120.4
O5—S1—N3107.34 (17)C4A—C5A—H5A120.4
O4—S1—N3109.32 (18)C5A—C6A—C1A120.3 (7)
O5—S1—C17112.6 (2)C5A—C6A—C7A130.4 (7)
O4—S1—C17104.8 (2)C1A—C6A—C7A109.1 (6)
N3—S1—C17101.4 (3)C6A—C7A—C8A103.2 (5)
O5—S1—C17A105.0 (3)C6A—C7A—H7C111.1
O4—S1—C17A105.4 (2)C8A—C7A—H7C111.1
N3—S1—C17A109.7 (3)C6A—C7A—H7D111.1
C22—O7—C23A117.9 (7)C8A—C7A—H7D111.1
C22—O7—C23116.5 (6)H7C—C7A—H7D109.1
C26—O9—C27116.2 (3)C9A—C8A—C7A118.0 (7)
C25—N3—C21119.3 (3)C9A—C8A—N1A109.3 (6)
C25—N3—S1121.8 (3)C7A—C8A—N1A100.5 (5)
C21—N3—S1118.7 (2)C9A—C8A—H8A109.5
C11—O2—C12119.0 (6)C7A—C8A—H8A109.5
N2—N1—C1118.0 (4)N1A—C8A—H8A109.5
N2—N1—C8121.5 (5)C8A—C9A—H9D109.5
C1—N1—C8107.6 (5)C8A—C9A—H9E109.5
C14—N2—N1119.6 (5)H9D—C9A—H9E109.5
C14—N2—C10116.8 (5)C8A—C9A—H9F109.5
N1—N2—C10123.5 (5)H9D—C9A—H9F109.5
C2—C1—C6122.3 (5)H9E—C9A—H9F109.5
C2—C1—N1127.6 (4)C11A—C10A—N2A111.1 (6)
C6—C1—N1110.0 (5)C11A—C10A—H10C109.4
C1—C2—C3117.6 (6)N2A—C10A—H10C109.4
C1—C2—H2121.2C11A—C10A—H10D109.4
C3—C2—H2121.2N2A—C10A—H10D109.4
C2—C3—C4118.5 (7)H10C—C10A—H10D108.0
C2—C3—H3120.7O3A—C11A—O2A123.3 (9)
C4—C3—H3120.7O3A—C11A—C10A124.2 (9)
C5—C4—C3122.1 (6)O2A—C11A—C10A110.7 (5)
C5—C4—H4118.9O2A—C12A—C13A107.1 (7)
C3—C4—H4118.9O2A—C12A—H12C110.3
C6—C5—C4118.6 (7)C13A—C12A—H12C110.3
C6—C5—H5120.7O2A—C12A—H12D110.3
C4—C5—H5120.7C13A—C12A—H12D110.3
C5—C6—C1120.8 (7)H12C—C12A—H12D108.6
C5—C6—C7129.8 (6)C12A—C13A—H13D109.5
C1—C6—C7109.4 (6)C12A—C13A—H13E109.5
C6—C7—C8103.8 (5)H13D—C13A—H13E109.5
C6—C7—H7A111.0C12A—C13A—H13F109.5
C8—C7—H7A111.0H13D—C13A—H13F109.5
C6—C7—H7B111.0H13E—C13A—H13F109.5
C8—C7—H7B111.0O1A—C14A—N2A123.3 (5)
H7A—C7—H7B109.0O1A—C14A—C15A120.4 (6)
C9—C8—N1111.7 (6)N2A—C14A—C15A116.1 (5)
C9—C8—C7116.8 (7)C16A—C15A—C20A120.0
N1—C8—C7102.8 (5)C16A—C15A—C14A120.7 (3)
C9—C8—H8108.4C20A—C15A—C14A119.2 (3)
N1—C8—H8108.4C15A—C16A—C17A120.0
C7—C8—H8108.4C15A—C16A—H16A120.0
C8—C9—H9A109.5C17A—C16A—H16A120.0
C8—C9—H9B109.5C16A—C17A—C18A120.0
H9A—C9—H9B109.5C16A—C17A—S1115.3 (3)
C8—C9—H9C109.5C18A—C17A—S1124.6 (3)
H9A—C9—H9C109.5C19A—C18A—C17A120.0
H9B—C9—H9C109.5C19A—C18A—Cl1A117.7 (3)
C11—C10—N2124.7 (7)C17A—C18A—Cl1A122.3 (3)
C11—C10—H10A106.2C18A—C19A—C20A120.0
N2—C10—H10A106.2C18A—C19A—H19A120.0
C11—C10—H10B106.2C20A—C19A—H19A120.0
N2—C10—H10B106.2C19A—C20A—C15A120.0
H10A—C10—H10B106.4C19A—C20A—H20A120.0
O3—C11—O2118.3 (7)C15A—C20A—H20A120.0
O3—C11—C10125.2 (8)N3—C21—C22115.5 (3)
O2—C11—C10114.5 (5)N3—C21—H21A108.4
O2—C12—C13107.3 (7)C22—C21—H21A108.4
O2—C12—H12A110.3N3—C21—H21B108.4
C13—C12—H12A110.3C22—C21—H21B108.4
O2—C12—H12B110.3H21A—C21—H21B107.5
C13—C12—H12B110.3O6—C22—O7125.1 (4)
H12A—C12—H12B108.5O6—C22—C21121.4 (4)
C12—C13—H13A109.5O7—C22—C21113.5 (3)
C12—C13—H13B109.5O7—C23—C24108.4 (8)
H13A—C13—H13B109.5O7—C23—H23A110.0
C12—C13—H13C109.5C24—C23—H23A110.0
H13A—C13—H13C109.5O7—C23—H23B110.0
H13B—C13—H13C109.5C24—C23—H23B110.0
O1—C14—N2119.5 (5)H23A—C23—H23B108.4
O1—C14—C15119.3 (5)C23—C24—H24A109.5
N2—C14—C15120.8 (5)C23—C24—H24B109.5
C16—C15—C20120.0H24A—C24—H24B109.5
C16—C15—C14122.1 (3)C23—C24—H24C109.5
C20—C15—C14117.9 (3)H24A—C24—H24C109.5
C17—C16—C15120.0H24B—C24—H24C109.5
C17—C16—H16120.0O7—C23A—C24A102.2 (8)
C15—C16—H16120.0O7—C23A—H23C111.3
C16—C17—C18120.0C24A—C23A—H23C111.3
C16—C17—S1116.6 (3)O7—C23A—H23D111.3
C18—C17—S1123.4 (3)C24A—C23A—H23D111.3
C17—C18—C19120.0H23C—C23A—H23D109.2
C17—C18—Cl1122.3 (2)C23A—C24A—H24D109.5
C19—C18—Cl1117.7 (2)C23A—C24A—H24E109.5
C20—C19—C18120.0H24D—C24A—H24E109.5
C20—C19—H19120.0C23A—C24A—H24F109.5
C18—C19—H19120.0H24D—C24A—H24F109.5
C19—C20—C15120.0H24E—C24A—H24F109.5
C19—C20—H20120.0N3—C25—C26112.3 (3)
C15—C20—H20120.0N3—C25—H25A109.1
C11A—O2A—C12A117.3 (7)C26—C25—H25A109.1
C1A—N1A—N2A115.3 (5)N3—C25—H25B109.1
C1A—N1A—C8A105.9 (5)C26—C25—H25B109.1
N2A—N1A—C8A112.7 (5)H25A—C25—H25B107.9
C14A—N2A—N1A121.3 (5)O8—C26—O9124.6 (4)
C14A—N2A—C10A118.6 (5)O8—C26—C25125.6 (4)
N1A—N2A—C10A110.5 (5)O9—C26—C25109.7 (3)
C2A—C1A—C6A122.2 (6)O9—C27—C28106.9 (4)
C2A—C1A—N1A128.4 (5)O9—C27—H27A110.3
C6A—C1A—N1A109.1 (5)C28—C27—H27A110.3
C1A—C2A—C3A118.1 (6)O9—C27—H27B110.3
C1A—C2A—H2A120.9C28—C27—H27B110.3
C3A—C2A—H2A120.9H27A—C27—H27B108.6
C2A—C3A—C4A118.1 (7)C27—C28—H28A109.5
C2A—C3A—H3A121.0C27—C28—H28B109.5
C4A—C3A—H3A121.0H28A—C28—H28B109.5
C5A—C4A—C3A121.9 (7)C27—C28—H28C109.5
C5A—C4A—H4A119.1H28A—C28—H28C109.5
C3A—C4A—H4A119.1H28B—C28—H28C109.5
C6A—C5A—C4A119.3 (7)
O5—S1—N3—C253.4 (3)C8A—N1A—C1A—C2A160 (2)
O4—S1—N3—C25134.7 (3)N2A—N1A—C1A—C6A150.5 (9)
C17—S1—N3—C25114.9 (3)C8A—N1A—C1A—C6A25.1 (12)
C17A—S1—N3—C25110.1 (4)C6A—C1A—C2A—C3A3 (3)
O5—S1—N3—C21171.8 (3)N1A—C1A—C2A—C3A171.0 (16)
O4—S1—N3—C2140.4 (3)C1A—C2A—C3A—C4A2 (3)
C17—S1—N3—C2169.9 (4)C2A—C3A—C4A—C5A2 (2)
C17A—S1—N3—C2174.7 (4)C3A—C4A—C5A—C6A2.7 (18)
C1—N1—N2—C14125.3 (8)C4A—C5A—C6A—C1A3.8 (17)
C8—N1—N2—C1498.0 (8)C4A—C5A—C6A—C7A178.2 (10)
C1—N1—N2—C1056.6 (11)C2A—C1A—C6A—C5A4 (2)
C8—N1—N2—C1080.0 (9)N1A—C1A—C6A—C5A171.0 (10)
N2—N1—C1—C224 (2)C2A—C1A—C6A—C7A179.6 (19)
C8—N1—C1—C2166.5 (17)N1A—C1A—C6A—C7A4.6 (14)
N2—N1—C1—C6159.4 (8)C5A—C6A—C7A—C8A167.4 (10)
C8—N1—C1—C617.3 (11)C1A—C6A—C7A—C8A17.7 (12)
C6—C1—C2—C32 (3)C6A—C7A—C8A—C9A149.1 (7)
N1—C1—C2—C3177.6 (14)C6A—C7A—C8A—N1A30.5 (8)
C1—C2—C3—C42 (3)C1A—N1A—C8A—C9A159.4 (9)
C2—C3—C4—C51.9 (18)N2A—N1A—C8A—C9A73.6 (8)
C3—C4—C5—C61.7 (14)C1A—N1A—C8A—C7A34.5 (8)
C4—C5—C6—C11.5 (15)N2A—N1A—C8A—C7A161.6 (6)
C4—C5—C6—C7178.3 (8)C14A—N2A—C10A—C11A76.9 (10)
C2—C1—C6—C52 (2)N1A—N2A—C10A—C11A136.3 (7)
N1—C1—C6—C5178.1 (9)C12A—O2A—C11A—O3A8.4 (14)
C2—C1—C6—C7178.3 (16)C12A—O2A—C11A—C10A173.8 (9)
N1—C1—C6—C71.8 (12)N2A—C10A—C11A—O3A157.4 (9)
C5—C6—C7—C8166.1 (9)N2A—C10A—C11A—O2A7.9 (11)
C1—C6—C7—C814.1 (10)C11A—O2A—C12A—C13A171.3 (10)
N2—N1—C8—C968.4 (8)N1A—N2A—C14A—O1A161.4 (9)
C1—N1—C8—C9151.1 (8)C10A—N2A—C14A—O1A18.3 (13)
N2—N1—C8—C7165.6 (6)N1A—N2A—C14A—C15A22.1 (11)
C1—N1—C8—C725.1 (8)C10A—N2A—C14A—C15A165.3 (7)
C6—C7—C8—C9145.6 (7)O1A—C14A—C15A—C16A139.4 (8)
C6—C7—C8—N122.9 (7)N2A—C14A—C15A—C16A37.2 (10)
C14—N2—C10—C1154.6 (11)O1A—C14A—C15A—C20A39.4 (11)
N1—N2—C10—C11127.3 (7)N2A—C14A—C15A—C20A144.1 (6)
C12—O2—C11—O31.3 (12)C20A—C15A—C16A—C17A0.0
C12—O2—C11—C10166.1 (8)C14A—C15A—C16A—C17A178.7 (7)
N2—C10—C11—O3156.4 (8)C15A—C16A—C17A—C18A0.0
N2—C10—C11—O240.0 (10)C15A—C16A—C17A—S1176.6 (6)
C11—O2—C12—C13164.7 (8)O5—S1—C17A—C16A133.4 (4)
N1—N2—C14—O1162.5 (7)O4—S1—C17A—C16A6.0 (5)
C10—N2—C14—O115.7 (11)N3—S1—C17A—C16A111.6 (4)
N1—N2—C14—C1524.8 (10)O5—S1—C17A—C18A50.2 (5)
C10—N2—C14—C15157.0 (7)O4—S1—C17A—C18A177.6 (4)
O1—C14—C15—C16143.7 (6)N3—S1—C17A—C18A64.8 (5)
N2—C14—C15—C1629.1 (9)C16A—C17A—C18A—C19A0.0
O1—C14—C15—C2035.0 (9)S1—C17A—C18A—C19A176.2 (6)
N2—C14—C15—C20152.3 (6)C16A—C17A—C18A—Cl1A179.1 (10)
C20—C15—C16—C170.0S1—C17A—C18A—Cl1A2.9 (10)
C14—C15—C16—C17178.6 (6)C17A—C18A—C19A—C20A0.0
C15—C16—C17—C180.0Cl1A—C18A—C19A—C20A179.2 (10)
C15—C16—C17—S1179.3 (5)C18A—C19A—C20A—C15A0.0
O5—S1—C17—C16134.0 (3)C16A—C15A—C20A—C19A0.0
O4—S1—C17—C162.2 (4)C14A—C15A—C20A—C19A178.7 (7)
N3—S1—C17—C16111.6 (3)C25—N3—C21—C2278.8 (4)
O5—S1—C17—C1845.2 (4)S1—N3—C21—C22105.9 (4)
O4—S1—C17—C18177.1 (3)C23A—O7—C22—O65.5 (10)
N3—S1—C17—C1869.2 (4)C23—O7—C22—O69.4 (9)
C16—C17—C18—C190.0C23A—O7—C22—C21176.0 (9)
S1—C17—C18—C19179.2 (5)C23—O7—C22—C21169.2 (8)
C16—C17—C18—Cl1179.8 (8)N3—C21—C22—O6179.2 (4)
S1—C17—C18—Cl11.0 (8)N3—C21—C22—O70.5 (5)
C17—C18—C19—C200.0C22—O7—C23—C24177.1 (10)
Cl1—C18—C19—C20179.8 (8)C22—O7—C23A—C24A131.8 (11)
C18—C19—C20—C150.0C21—N3—C25—C2674.6 (4)
C16—C15—C20—C190.0S1—N3—C25—C26100.5 (3)
C14—C15—C20—C19178.7 (6)C27—O9—C26—O84.1 (7)
C1A—N1A—N2A—C14A135.0 (9)C27—O9—C26—C25173.5 (4)
C8A—N1A—N2A—C14A103.1 (8)N3—C25—C26—O85.9 (6)
C1A—N1A—N2A—C10A79.2 (10)N3—C25—C26—O9176.5 (3)
C8A—N1A—N2A—C10A42.7 (8)C26—O9—C27—C28168.9 (4)
N2A—N1A—C1A—C2A35 (2)
Hydrogen-bond geometry (Å, º) top
Cg4 is the centroid of the major orientation of the C15–C20 benzene ring.
D—H···AD—HH···AD···AD—H···A
C2—H2···O20.952.373.198 (13)145
C4—H4···O9i0.952.483.262 (8)139
C10—H10A···Cl1i0.992.883.708 (11)141
C24—H24A···Cl10.982.863.51 (2)124
C25—H25A···O5ii0.992.413.100 (5)126
C27—H27B···Cg4ii0.992.923.742 (7)141
Symmetry codes: (i) x+1, y, z; (ii) x+1, y1/2, z+1.
 

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