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The crystal structure of the addition product of p-quinone­benzene­sulfon­imide and di­phenyl­diazo­methane, C31H24N2O4S2, confirms earlier spectroscopic evidence that it is not a substituted benzocyclopropene, as previously claimed, but contains instead a bicyclic three-membered ring fused to a six-membered ring incorporating only one double bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804010815/na6324sup1.cif
Contains datablocks global, 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804010815/na63242sup2.hkl
Contains datablock 2

CCDC reference: 242319

Key indicators

  • Single-crystal X-ray study
  • T = 110 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.032
  • wR factor = 0.087
  • Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
Alert level G ABSTY01_ALERT_1_G Extra text has been found in the _exptl_absorpt_correction_type field, which should be only a single keyword. A literature citation should be included in the _exptl_absorpt_process_details field.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: Apex2 (Bruker, 2003); cell refinement: Apex2; data reduction: SAINT-Plus (Bruker 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.

(2) top
Crystal data top
C31H24N2O4S2F(000) = 1152
Mr = 552.64Dx = 1.401 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 7.0546 (3) ÅCell parameters from 6775 reflections
b = 23.3933 (11) Åθ = 2.7–30.2°
c = 16.2515 (9) ŵ = 0.25 mm1
β = 102.405 (3)°T = 110 K
V = 2619.4 (2) Å3Block, colorless
Z = 40.26 × 0.22 × 0.15 mm
Data collection top
Bruker X8 APEX CCD area-detector
diffractometer
5352 independent reflections
Radiation source: fine-focus sealed tube4696 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
φ and ω scansθmax = 26.4°, θmin = 1.7°
Absorption correction: multi-scan; (bruker, 2000)
(SADABS; Sheldrick, 1996)
h = 88
Tmin = 0.900, Tmax = 0.964k = 2929
53078 measured reflectionsl = 2020
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.041P)2 + 1.5285P]
where P = (Fo2 + 2Fc2)/3
5352 reflections(Δ/σ)max = 0.001
352 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.43 e Å3
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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.71050 (18)0.22084 (6)0.43335 (8)0.0173 (3)
C20.6345 (2)0.25590 (6)0.49359 (9)0.0197 (3)
H20.60530.23830.54070.024*
C30.6051 (2)0.31231 (6)0.48375 (9)0.0203 (3)
H30.55410.33200.52370.024*
C40.64991 (19)0.34422 (6)0.41283 (9)0.0184 (3)
C50.75099 (19)0.31425 (6)0.35417 (9)0.0168 (3)
H50.72100.32800.29590.020*
C60.78275 (19)0.24985 (6)0.36497 (8)0.0168 (3)
H60.77050.22800.31260.020*
C70.95601 (19)0.29081 (6)0.38538 (8)0.0168 (3)
C81.08361 (19)0.29257 (6)0.32126 (8)0.0178 (3)
C91.1868 (2)0.24404 (6)0.30670 (9)0.0220 (3)
H91.17570.21040.33570.026*
C101.3065 (2)0.24592 (7)0.24875 (10)0.0262 (3)
H101.37420.21340.23890.031*
C111.3248 (2)0.29624 (7)0.20575 (9)0.0276 (3)
H111.40440.29740.16700.033*
C121.2245 (2)0.34486 (8)0.22065 (10)0.0297 (4)
H121.23760.37860.19220.036*
C131.1036 (2)0.34302 (7)0.27841 (9)0.0244 (3)
H131.03620.37560.28830.029*
C141.06556 (19)0.30019 (6)0.47480 (8)0.0180 (3)
C151.1034 (2)0.35587 (6)0.50514 (9)0.0218 (3)
H151.05360.38680.47140.026*
C161.2153 (2)0.36514 (7)0.58563 (10)0.0262 (3)
H161.23880.40220.60590.031*
C171.2921 (2)0.31891 (7)0.63587 (9)0.0267 (3)
H171.36760.32510.68950.032*
C181.2560 (2)0.26352 (7)0.60593 (9)0.0253 (3)
H181.30730.23270.63960.030*
C191.1429 (2)0.25400 (6)0.52549 (9)0.0209 (3)
H191.11900.21680.50560.025*
C200.7410 (2)0.05486 (6)0.42213 (9)0.0205 (3)
C210.7919 (2)0.04525 (7)0.50878 (10)0.0242 (3)
H210.84150.07470.54560.029*
C220.7669 (2)0.00920 (7)0.53884 (10)0.0292 (3)
H220.79790.01630.59650.035*
C230.6960 (2)0.05302 (7)0.48319 (11)0.0309 (4)
H230.67990.08940.50380.037*
C240.6492 (2)0.04316 (7)0.39739 (11)0.0303 (4)
H240.60390.07300.36060.036*
C250.6696 (2)0.01135 (6)0.36579 (10)0.0251 (3)
H250.63610.01840.30820.030*
C260.4632 (2)0.49457 (6)0.33871 (9)0.0206 (3)
C270.3518 (2)0.49614 (6)0.39992 (10)0.0262 (3)
H270.36630.46820.44150.031*
C280.2187 (2)0.54023 (7)0.39761 (10)0.0269 (3)
H280.14350.54190.43800.032*
C290.1974 (2)0.58164 (7)0.33557 (10)0.0259 (3)
H290.10850.61110.33470.031*
C300.3081 (2)0.57947 (7)0.27458 (10)0.0290 (3)
H300.29210.60720.23270.035*
C310.4428 (2)0.53597 (7)0.27600 (9)0.0249 (3)
H310.51820.53450.23560.030*
N10.70278 (17)0.16598 (5)0.44514 (7)0.0192 (2)
N20.59438 (18)0.39709 (5)0.40807 (8)0.0226 (3)
O10.66538 (17)0.12614 (4)0.29626 (7)0.0286 (2)
O20.99008 (15)0.13034 (4)0.39007 (7)0.0272 (2)
O30.83147 (17)0.46701 (5)0.37479 (10)0.0450 (3)
O40.6184 (2)0.42025 (5)0.25395 (8)0.0386 (3)
S10.78370 (5)0.121888 (14)0.37991 (2)0.01941 (9)
S20.64494 (5)0.442814 (15)0.33813 (3)0.02583 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0118 (6)0.0229 (7)0.0168 (6)0.0004 (5)0.0019 (5)0.0002 (5)
C20.0171 (7)0.0260 (7)0.0175 (7)0.0011 (5)0.0071 (5)0.0015 (5)
C30.0170 (7)0.0256 (7)0.0199 (7)0.0018 (5)0.0079 (5)0.0016 (6)
C40.0130 (6)0.0222 (7)0.0202 (7)0.0001 (5)0.0039 (5)0.0007 (5)
C50.0146 (6)0.0186 (7)0.0176 (6)0.0001 (5)0.0046 (5)0.0008 (5)
C60.0154 (6)0.0192 (7)0.0163 (6)0.0006 (5)0.0043 (5)0.0010 (5)
C70.0141 (6)0.0196 (7)0.0175 (6)0.0003 (5)0.0055 (5)0.0007 (5)
C80.0129 (6)0.0258 (7)0.0147 (6)0.0014 (5)0.0030 (5)0.0023 (5)
C90.0182 (7)0.0250 (7)0.0235 (7)0.0016 (6)0.0064 (6)0.0040 (6)
C100.0171 (7)0.0353 (8)0.0277 (8)0.0008 (6)0.0083 (6)0.0106 (6)
C110.0163 (7)0.0492 (10)0.0191 (7)0.0028 (6)0.0078 (6)0.0027 (7)
C120.0231 (8)0.0414 (9)0.0269 (8)0.0006 (7)0.0100 (6)0.0103 (7)
C130.0196 (7)0.0301 (8)0.0253 (7)0.0033 (6)0.0092 (6)0.0046 (6)
C140.0119 (6)0.0268 (7)0.0167 (7)0.0000 (5)0.0062 (5)0.0026 (5)
C150.0162 (7)0.0266 (7)0.0238 (7)0.0012 (6)0.0069 (6)0.0029 (6)
C160.0192 (7)0.0342 (8)0.0265 (8)0.0018 (6)0.0079 (6)0.0114 (6)
C170.0169 (7)0.0483 (10)0.0157 (7)0.0007 (6)0.0052 (5)0.0057 (6)
C180.0182 (7)0.0404 (9)0.0185 (7)0.0027 (6)0.0064 (6)0.0051 (6)
C190.0161 (6)0.0270 (7)0.0211 (7)0.0006 (5)0.0071 (5)0.0004 (6)
C200.0182 (7)0.0203 (7)0.0257 (7)0.0020 (5)0.0110 (6)0.0041 (6)
C210.0219 (7)0.0270 (8)0.0256 (7)0.0040 (6)0.0093 (6)0.0031 (6)
C220.0247 (8)0.0352 (9)0.0309 (8)0.0086 (6)0.0129 (6)0.0135 (7)
C230.0236 (8)0.0240 (8)0.0494 (10)0.0034 (6)0.0171 (7)0.0120 (7)
C240.0258 (8)0.0233 (8)0.0449 (10)0.0030 (6)0.0144 (7)0.0003 (7)
C250.0243 (7)0.0254 (7)0.0279 (8)0.0009 (6)0.0110 (6)0.0005 (6)
C260.0176 (7)0.0187 (7)0.0263 (7)0.0008 (5)0.0061 (6)0.0026 (6)
C270.0278 (8)0.0224 (7)0.0318 (8)0.0016 (6)0.0140 (6)0.0044 (6)
C280.0254 (8)0.0275 (8)0.0309 (8)0.0015 (6)0.0127 (6)0.0020 (6)
C290.0226 (7)0.0238 (7)0.0308 (8)0.0045 (6)0.0047 (6)0.0020 (6)
C300.0307 (8)0.0295 (8)0.0270 (8)0.0059 (7)0.0065 (6)0.0063 (6)
C310.0241 (7)0.0283 (8)0.0233 (7)0.0007 (6)0.0076 (6)0.0003 (6)
N10.0179 (6)0.0214 (6)0.0194 (6)0.0015 (5)0.0066 (5)0.0001 (5)
N20.0208 (6)0.0216 (6)0.0275 (6)0.0019 (5)0.0101 (5)0.0017 (5)
O10.0423 (7)0.0236 (5)0.0201 (5)0.0021 (5)0.0072 (5)0.0009 (4)
O20.0243 (6)0.0231 (5)0.0390 (6)0.0013 (4)0.0176 (5)0.0024 (5)
O30.0211 (6)0.0341 (7)0.0816 (10)0.0001 (5)0.0147 (6)0.0164 (7)
O40.0622 (8)0.0256 (6)0.0388 (7)0.0105 (6)0.0350 (6)0.0075 (5)
S10.02285 (19)0.01826 (17)0.01941 (18)0.00026 (13)0.00960 (14)0.00110 (13)
S20.02355 (19)0.02030 (18)0.0386 (2)0.00311 (14)0.01777 (16)0.00574 (15)
Geometric parameters (Å, º) top
C1—N11.3006 (18)C17—H170.9300
C1—C21.4645 (19)C18—C191.395 (2)
C1—C61.4827 (19)C18—H180.9300
C2—C31.340 (2)C19—H190.9300
C2—H20.9300C20—C251.389 (2)
C3—C41.4635 (19)C20—C211.395 (2)
C3—H30.9300C20—S11.7632 (14)
C4—N21.2947 (18)C21—C221.389 (2)
C4—C51.4835 (18)C21—H210.9300
C5—C61.5278 (19)C22—C231.387 (2)
C5—C71.5281 (18)C22—H220.9300
C5—H50.9800C23—C241.382 (2)
C6—C71.5323 (18)C23—H230.9300
C6—H60.9800C24—C251.394 (2)
C7—C141.5082 (19)C24—H240.9300
C7—C81.5168 (18)C25—H250.9300
C8—C131.393 (2)C26—C311.391 (2)
C8—C91.396 (2)C26—C271.394 (2)
C9—C101.394 (2)C26—S21.7652 (14)
C9—H90.9300C27—C281.390 (2)
C10—C111.389 (2)C27—H270.9300
C10—H100.9300C28—C291.383 (2)
C11—C121.388 (2)C28—H280.9300
C11—H110.9300C29—C301.388 (2)
C12—C131.398 (2)C29—H290.9300
C12—H120.9300C30—C311.389 (2)
C13—H130.9300C30—H300.9300
C14—C191.397 (2)C31—H310.9300
C14—C151.398 (2)N1—S11.6653 (12)
C15—C161.392 (2)N2—S21.6545 (13)
C15—H150.9300O1—S11.4378 (11)
C16—C171.393 (2)O2—S11.4433 (11)
C16—H160.9300O3—S21.4388 (13)
C17—C181.388 (2)O4—S21.4406 (13)
N1—C1—C2114.91 (12)C18—C17—H17120.0
N1—C1—C6126.45 (12)C16—C17—H17120.0
C2—C1—C6118.62 (12)C17—C18—C19120.15 (14)
C3—C2—C1122.76 (13)C17—C18—H18119.9
C3—C2—H2118.6C19—C18—H18119.9
C1—C2—H2118.6C18—C19—C14120.09 (14)
C2—C3—C4122.84 (13)C18—C19—H19120.0
C2—C3—H3118.6C14—C19—H19120.0
C4—C3—H3118.6C25—C20—C21121.71 (14)
N2—C4—C3114.87 (12)C25—C20—S1117.59 (11)
N2—C4—C5126.45 (13)C21—C20—S1120.52 (12)
C3—C4—C5118.68 (12)C22—C21—C20118.58 (15)
C4—C5—C6118.10 (11)C22—C21—H21120.7
C4—C5—C7120.51 (12)C20—C21—H21120.7
C6—C5—C760.19 (9)C23—C22—C21120.23 (15)
C4—C5—H5115.6C23—C22—H22119.9
C6—C5—H5115.6C21—C22—H22119.9
C7—C5—H5115.6C24—C23—C22120.60 (14)
C1—C6—C5118.16 (11)C24—C23—H23119.7
C1—C6—C7120.70 (11)C22—C23—H23119.7
C5—C6—C759.91 (8)C23—C24—C25120.24 (16)
C1—C6—H6115.6C23—C24—H24119.9
C5—C6—H6115.6C25—C24—H24119.9
C7—C6—H6115.6C20—C25—C24118.62 (15)
C14—C7—C8113.64 (11)C20—C25—H25120.7
C14—C7—C5121.35 (11)C24—C25—H25120.7
C8—C7—C5114.92 (11)C31—C26—C27121.27 (13)
C14—C7—C6121.29 (11)C31—C26—S2115.75 (11)
C8—C7—C6115.58 (11)C27—C26—S2122.91 (12)
C5—C7—C659.90 (9)C28—C27—C26118.77 (14)
C13—C8—C9119.47 (13)C28—C27—H27120.6
C13—C8—C7120.35 (12)C26—C27—H27120.6
C9—C8—C7120.16 (13)C29—C28—C27120.42 (14)
C10—C9—C8120.16 (14)C29—C28—H28119.8
C10—C9—H9119.9C27—C28—H28119.8
C8—C9—H9119.9C28—C29—C30120.36 (14)
C11—C10—C9120.14 (14)C28—C29—H29119.8
C11—C10—H10119.9C30—C29—H29119.8
C9—C10—H10119.9C29—C30—C31120.16 (14)
C12—C11—C10120.03 (14)C29—C30—H30119.9
C12—C11—H11120.0C31—C30—H30119.9
C10—C11—H11120.0C30—C31—C26119.01 (14)
C11—C12—C13119.96 (15)C30—C31—H31120.5
C11—C12—H12120.0C26—C31—H31120.5
C13—C12—H12120.0C1—N1—S1119.11 (10)
C8—C13—C12120.24 (14)C4—N2—S2123.46 (10)
C8—C13—H13119.9O1—S1—O2117.72 (7)
C12—C13—H13119.9O1—S1—N1110.51 (6)
C19—C14—C15119.47 (13)O2—S1—N1108.52 (6)
C19—C14—C7120.68 (13)O1—S1—C20108.45 (7)
C15—C14—C7119.66 (13)O2—S1—C20109.27 (7)
C16—C15—C14120.22 (14)N1—S1—C20101.09 (6)
C16—C15—H15119.9O3—S2—O4117.26 (8)
C14—C15—H15119.9O3—S2—N2106.42 (7)
C15—C16—C17120.04 (14)O4—S2—N2114.35 (7)
C15—C16—H16120.0O3—S2—C26109.20 (7)
C17—C16—H16120.0O4—S2—C26108.07 (7)
C18—C17—C16120.02 (14)N2—S2—C26100.11 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O40.982.333.004 (2)125
C6—H6···O10.982.493.148 (2)124
 

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