Download citation
Download citation
link to html
The title compound, C21H20N4O5S·C6H6, is a by-product of the synthesis of tazobactam. The crystal structure is stabilized by inter­molecular C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806036439/ez2032sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806036439/ez2032Isup2.hkl
Contains datablock I

CCDC reference: 624209

Key indicators

  • Single-crystal X-ray study
  • T = 113 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.032
  • wR factor = 0.083
  • Data-to-parameter ratio = 19.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - C1 .. 5.34 su PLAT230_ALERT_2_C Hirshfeld Test Diff for N2 - N3 .. 6.17 su PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 1 C5 -N2 -N3 -N4 18.00 0.00 1.555 1.555 1.555 1.555 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C6 H6
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 28.70 From the CIF: _reflns_number_total 6459 Count of symmetry unique reflns 3509 Completeness (_total/calc) 184.07% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2950 Fraction of Friedel pairs measured 0.841 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

Diphenylmethyl 3-azido-1,1-dioxocephalosporanate benzene solvate top
Crystal data top
C21H20N4O5S·C6H6F(000) = 544
Mr = 518.58Dx = 1.337 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71070 Å
Hall symbol: P 2ybCell parameters from 4488 reflections
a = 8.9971 (17) Åθ = 1.5–28.7°
b = 10.3052 (19) ŵ = 0.17 mm1
c = 13.954 (3) ÅT = 113 K
β = 95.374 (3)°Block, colorless
V = 1288.1 (4) Å30.32 × 0.20 × 0.14 mm
Z = 2
Data collection top
Rigaku Saturn
diffractometer
6459 independent reflections
Radiation source: rotating anode4755 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.045
Detector resolution: 7.31 pixels mm-1θmax = 28.7°, θmin = 1.5°
ω scansh = 1112
Absorption correction: multi-scan
(Jacobson, 1998)
k = 1313
Tmin = 0.947, Tmax = 0.971l = 1818
17106 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.032 w = 1/[σ2(Fo2) + (0.0416P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.083(Δ/σ)max = 0.001
S = 0.96Δρmax = 0.30 e Å3
6459 reflectionsΔρmin = 0.27 e Å3
337 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.067 (2)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983)
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.02 (5)
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
S10.35063 (5)0.34826 (4)0.60314 (3)0.01672 (11)
O10.24143 (14)0.75992 (13)0.55496 (10)0.0229 (3)
O20.33065 (15)0.23296 (13)0.65849 (10)0.0234 (3)
O30.28116 (12)0.35643 (14)0.50579 (8)0.0211 (3)
O40.57154 (14)0.51673 (13)0.80289 (9)0.0228 (3)
O50.73389 (13)0.66953 (12)0.76301 (8)0.0175 (3)
N10.37455 (15)0.60149 (14)0.64978 (10)0.0149 (3)
N20.51162 (16)0.56208 (14)0.48223 (10)0.0162 (3)
N30.53063 (16)0.49582 (15)0.41019 (11)0.0176 (3)
N40.5373 (2)0.44575 (17)0.33845 (12)0.0279 (4)
C10.25232 (18)0.66138 (19)0.60101 (13)0.0179 (4)
C20.1485 (2)0.55310 (18)0.62841 (13)0.0193 (4)
H2A0.09540.50750.57290.023*
H2B0.07930.57870.67620.023*
C30.29225 (18)0.48423 (17)0.67192 (13)0.0157 (4)
H30.29340.46620.74240.019*
C40.54544 (19)0.37798 (17)0.60084 (13)0.0163 (4)
H4A0.59570.35650.66500.020*
H4B0.58420.31750.55400.020*
C50.59091 (19)0.51705 (17)0.57485 (12)0.0148 (4)
C60.53447 (19)0.61664 (17)0.64678 (12)0.0147 (4)
H60.55600.70650.62480.018*
C70.61197 (19)0.59549 (17)0.74693 (12)0.0166 (4)
C80.76014 (18)0.52379 (19)0.57158 (13)0.0186 (4)
H8A0.78910.47050.51820.022*
H8B0.80980.49120.63230.022*
H8C0.79000.61400.56210.022*
C90.82478 (18)0.64436 (18)0.85411 (12)0.0160 (4)
H90.83700.54840.86200.019*
C100.74513 (18)0.69596 (18)0.93742 (13)0.0175 (4)
C110.7290 (2)0.61692 (19)1.01652 (13)0.0220 (4)
H110.76930.53161.01850.026*
C120.6544 (2)0.6619 (2)1.09244 (14)0.0290 (5)
H120.64500.60801.14670.035*
C130.5942 (2)0.7842 (2)1.08929 (15)0.0284 (5)
H130.54220.81441.14120.034*
C140.6087 (2)0.8637 (2)1.01117 (14)0.0292 (5)
H140.56570.94801.00900.035*
C150.6859 (2)0.82081 (19)0.93568 (14)0.0258 (5)
H150.69840.87660.88280.031*
C160.9761 (2)0.70315 (18)0.84453 (12)0.0174 (4)
C171.1029 (2)0.64149 (19)0.88763 (13)0.0213 (4)
H171.09290.56310.92230.026*
C181.2436 (2)0.6934 (2)0.88037 (13)0.0240 (4)
H181.32940.65070.91010.029*
C191.2592 (2)0.8073 (2)0.82982 (14)0.0249 (5)
H191.35560.84310.82530.030*
C201.1346 (2)0.8691 (2)0.78593 (14)0.0258 (4)
H201.14560.94670.75050.031*
C210.9927 (2)0.81767 (18)0.79348 (14)0.0248 (4)
H210.90720.86090.76370.030*
C221.0675 (2)0.7631 (2)0.14501 (17)0.0367 (5)
H221.02400.80650.08920.044*
C251.1926 (2)0.6362 (2)0.30754 (16)0.0336 (5)
H251.23560.59220.36320.040*
C231.2086 (2)0.7103 (2)0.14592 (15)0.0335 (5)
H231.26280.71770.09100.040*
C261.0521 (2)0.6900 (3)0.30656 (18)0.0405 (6)
H260.99830.68390.36180.049*
C241.2705 (2)0.6466 (2)0.22734 (15)0.0325 (5)
H241.36740.60970.22800.039*
C270.9901 (3)0.7525 (2)0.22512 (18)0.0418 (6)
H270.89290.78880.22430.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0164 (2)0.0160 (2)0.0185 (2)0.00237 (19)0.00503 (16)0.00194 (19)
O10.0212 (7)0.0226 (8)0.0251 (7)0.0030 (6)0.0032 (6)0.0049 (6)
O20.0282 (7)0.0167 (7)0.0270 (7)0.0026 (6)0.0122 (6)0.0017 (6)
O30.0191 (6)0.0254 (7)0.0186 (6)0.0043 (6)0.0001 (5)0.0055 (6)
O40.0254 (7)0.0251 (8)0.0174 (6)0.0068 (6)0.0003 (5)0.0038 (6)
O50.0178 (6)0.0191 (7)0.0149 (6)0.0045 (5)0.0023 (5)0.0009 (5)
N10.0150 (8)0.0141 (8)0.0158 (7)0.0009 (6)0.0031 (6)0.0002 (6)
N20.0193 (7)0.0173 (8)0.0123 (7)0.0022 (6)0.0024 (6)0.0002 (6)
N30.0186 (8)0.0167 (8)0.0173 (8)0.0016 (6)0.0004 (6)0.0028 (6)
N40.0418 (11)0.0229 (10)0.0185 (8)0.0071 (8)0.0006 (8)0.0026 (7)
C10.0145 (8)0.0205 (10)0.0190 (9)0.0024 (8)0.0035 (7)0.0058 (8)
C20.0151 (9)0.0210 (10)0.0222 (9)0.0007 (7)0.0041 (7)0.0018 (8)
C30.0154 (9)0.0150 (9)0.0175 (9)0.0030 (7)0.0062 (7)0.0024 (7)
C40.0154 (8)0.0175 (10)0.0163 (8)0.0007 (7)0.0030 (7)0.0002 (7)
C50.0141 (8)0.0167 (9)0.0135 (8)0.0005 (7)0.0001 (7)0.0007 (7)
C60.0138 (8)0.0159 (9)0.0144 (8)0.0022 (7)0.0015 (7)0.0012 (7)
C70.0157 (9)0.0167 (9)0.0173 (9)0.0000 (7)0.0009 (7)0.0020 (7)
C80.0139 (9)0.0204 (10)0.0216 (9)0.0004 (7)0.0026 (7)0.0013 (8)
C90.0178 (9)0.0160 (9)0.0134 (8)0.0009 (7)0.0034 (7)0.0000 (7)
C100.0129 (8)0.0213 (10)0.0176 (9)0.0013 (7)0.0022 (7)0.0032 (7)
C110.0239 (10)0.0221 (11)0.0201 (9)0.0023 (8)0.0025 (8)0.0015 (8)
C120.0304 (11)0.0383 (13)0.0189 (9)0.0001 (10)0.0064 (8)0.0016 (9)
C130.0221 (10)0.0385 (13)0.0248 (10)0.0009 (9)0.0038 (8)0.0151 (9)
C140.0270 (10)0.0268 (12)0.0333 (11)0.0071 (10)0.0001 (8)0.0101 (10)
C150.0270 (10)0.0242 (12)0.0257 (10)0.0021 (8)0.0005 (8)0.0020 (8)
C160.0176 (9)0.0208 (10)0.0137 (9)0.0017 (7)0.0013 (7)0.0040 (7)
C170.0221 (9)0.0228 (11)0.0190 (9)0.0039 (8)0.0021 (8)0.0038 (8)
C180.0151 (9)0.0365 (12)0.0197 (9)0.0051 (8)0.0017 (7)0.0001 (9)
C190.0184 (10)0.0358 (12)0.0208 (9)0.0067 (8)0.0039 (8)0.0061 (8)
C200.0247 (10)0.0230 (11)0.0300 (10)0.0045 (9)0.0035 (8)0.0026 (9)
C210.0227 (10)0.0231 (12)0.0281 (10)0.0002 (8)0.0004 (8)0.0015 (8)
C220.0360 (13)0.0347 (13)0.0369 (13)0.0034 (10)0.0108 (10)0.0016 (10)
C250.0314 (12)0.0407 (14)0.0280 (11)0.0055 (10)0.0008 (9)0.0029 (10)
C230.0286 (11)0.0461 (14)0.0257 (11)0.0039 (10)0.0016 (9)0.0049 (10)
C260.0306 (12)0.0533 (16)0.0389 (13)0.0064 (11)0.0099 (10)0.0154 (12)
C240.0212 (10)0.0448 (13)0.0308 (11)0.0029 (10)0.0013 (9)0.0089 (10)
C270.0269 (12)0.0487 (16)0.0491 (15)0.0088 (11)0.0007 (11)0.0160 (12)
Geometric parameters (Å, º) top
S1—O21.4377 (14)C10—C151.392 (3)
S1—O31.4437 (12)C11—C121.386 (3)
S1—C41.7825 (18)C11—H110.9500
S1—C31.8041 (18)C12—C131.371 (3)
O1—C11.201 (2)C12—H120.9500
O4—C71.206 (2)C13—C141.379 (3)
O5—C71.338 (2)C13—H130.9500
O5—C91.469 (2)C14—C151.388 (3)
N1—C11.383 (2)C14—H140.9500
N1—C61.452 (2)C15—H150.9500
N1—C31.465 (2)C16—C171.392 (3)
N2—N31.240 (2)C16—C211.394 (3)
N2—C51.491 (2)C17—C181.387 (3)
N3—N41.133 (2)C17—H170.9500
C1—C21.527 (3)C18—C191.383 (3)
C2—C31.549 (3)C18—H180.9500
C2—H2A0.9900C19—C201.381 (3)
C2—H2B0.9900C19—H190.9500
C3—H31.0000C20—C211.395 (3)
C4—C51.543 (2)C20—H200.9500
C4—H4A0.9900C21—H210.9500
C4—H4B0.9900C22—C271.376 (3)
C5—C81.529 (2)C22—C231.379 (3)
C5—C61.554 (2)C22—H220.9500
C6—C71.518 (2)C25—C241.379 (3)
C6—H61.0000C25—C261.379 (3)
C8—H8A0.9800C25—H250.9500
C8—H8B0.9800C23—C241.384 (3)
C8—H8C0.9800C23—H230.9500
C9—C161.507 (2)C26—C271.378 (4)
C9—C101.518 (2)C26—H260.9500
C9—H91.0000C24—H240.9500
C10—C111.390 (3)C27—H270.9500
O2—S1—O3119.27 (8)O5—C9—H9108.5
O2—S1—C4108.93 (8)C16—C9—H9108.5
O3—S1—C4108.23 (7)C10—C9—H9108.5
O2—S1—C3107.39 (8)C11—C10—C15119.15 (17)
O3—S1—C3109.47 (8)C11—C10—C9119.65 (16)
C4—S1—C3102.23 (8)C15—C10—C9121.19 (17)
C7—O5—C9115.20 (13)C12—C11—C10120.32 (19)
C1—N1—C6133.03 (15)C12—C11—H11119.8
C1—N1—C394.44 (13)C10—C11—H11119.8
C6—N1—C3128.06 (13)C13—C12—C11120.1 (2)
N3—N2—C5116.12 (14)C13—C12—H12120.0
N4—N3—N2171.79 (19)C11—C12—H12120.0
O1—C1—N1131.44 (16)C12—C13—C14120.31 (19)
O1—C1—C2136.96 (16)C12—C13—H13119.8
N1—C1—C291.59 (14)C14—C13—H13119.8
C1—C2—C385.69 (13)C13—C14—C15120.1 (2)
C1—C2—H2A114.4C13—C14—H14119.9
C3—C2—H2A114.4C15—C14—H14119.9
C1—C2—H2B114.4C14—C15—C10119.96 (19)
C3—C2—H2B114.4C14—C15—H15120.0
H2A—C2—H2B111.5C10—C15—H15120.0
N1—C3—C287.68 (13)C17—C16—C21118.96 (17)
N1—C3—S1110.51 (11)C17—C16—C9119.24 (17)
C2—C3—S1114.93 (13)C21—C16—C9121.80 (17)
N1—C3—H3113.7C18—C17—C16120.60 (18)
C2—C3—H3113.7C18—C17—H17119.7
S1—C3—H3113.7C16—C17—H17119.7
C5—C4—S1116.53 (12)C19—C18—C17120.08 (18)
C5—C4—H4A108.2C19—C18—H18120.0
S1—C4—H4A108.2C17—C18—H18120.0
C5—C4—H4B108.2C20—C19—C18120.03 (18)
S1—C4—H4B108.2C20—C19—H19120.0
H4A—C4—H4B107.3C18—C19—H19120.0
N2—C5—C8110.92 (13)C19—C20—C21120.13 (19)
N2—C5—C4112.15 (14)C19—C20—H20119.9
C8—C5—C4109.63 (14)C21—C20—H20119.9
N2—C5—C6101.28 (13)C16—C21—C20120.20 (18)
C8—C5—C6112.08 (14)C16—C21—H21119.9
C4—C5—C6110.60 (13)C20—C21—H21119.9
N1—C6—C7109.22 (14)C27—C22—C23119.8 (2)
N1—C6—C5109.41 (13)C27—C22—H22120.1
C7—C6—C5110.50 (14)C23—C22—H22120.1
N1—C6—H6109.2C24—C25—C26119.7 (2)
C7—C6—H6109.2C24—C25—H25120.1
C5—C6—H6109.2C26—C25—H25120.1
O4—C7—O5124.59 (16)C22—C23—C24119.6 (2)
O4—C7—C6123.53 (16)C22—C23—H23120.2
O5—C7—C6111.79 (15)C24—C23—H23120.2
C5—C8—H8A109.5C27—C26—C25119.7 (2)
C5—C8—H8B109.5C27—C26—H26120.1
H8A—C8—H8B109.5C25—C26—H26120.1
C5—C8—H8C109.5C25—C24—C23120.4 (2)
H8A—C8—H8C109.5C25—C24—H24119.8
H8B—C8—H8C109.5C23—C24—H24119.8
O5—C9—C16106.65 (13)C22—C27—C26120.7 (2)
O5—C9—C10109.67 (13)C22—C27—H27119.7
C16—C9—C10114.97 (14)C26—C27—H27119.7
C5—N2—N3—N4179 (100)C9—O5—C7—O43.3 (2)
C6—N1—C1—O116.1 (3)C9—O5—C7—C6173.41 (13)
C3—N1—C1—O1172.8 (2)N1—C6—C7—O436.5 (2)
C6—N1—C1—C2162.85 (17)C5—C6—C7—O483.9 (2)
C3—N1—C1—C26.15 (13)N1—C6—C7—O5146.79 (14)
O1—C1—C2—C3173.0 (2)C5—C6—C7—O592.81 (17)
N1—C1—C2—C35.81 (13)C7—O5—C9—C16162.23 (15)
C1—N1—C3—C26.06 (13)C7—O5—C9—C1072.69 (18)
C6—N1—C3—C2164.52 (16)O5—C9—C10—C11130.64 (17)
C1—N1—C3—S1109.74 (13)C16—C9—C10—C11109.23 (19)
C6—N1—C3—S148.7 (2)O5—C9—C10—C1548.5 (2)
C1—C2—C3—N15.49 (12)C16—C9—C10—C1571.6 (2)
C1—C2—C3—S1106.09 (13)C15—C10—C11—C120.2 (3)
O2—S1—C3—N1150.94 (12)C9—C10—C11—C12178.96 (16)
O3—S1—C3—N178.21 (13)C10—C11—C12—C131.0 (3)
C4—S1—C3—N136.38 (14)C11—C12—C13—C140.7 (3)
O2—S1—C3—C2111.81 (13)C12—C13—C14—C150.7 (3)
O3—S1—C3—C219.04 (15)C13—C14—C15—C101.9 (3)
C4—S1—C3—C2133.63 (13)C11—C10—C15—C141.6 (3)
O2—S1—C4—C5160.62 (12)C9—C10—C15—C14177.52 (17)
O3—S1—C4—C568.31 (15)O5—C9—C16—C17144.64 (16)
C3—S1—C4—C547.19 (14)C10—C9—C16—C1793.6 (2)
N3—N2—C5—C863.9 (2)O5—C9—C16—C2135.2 (2)
N3—N2—C5—C459.10 (19)C10—C9—C16—C2186.5 (2)
N3—N2—C5—C6177.03 (14)C21—C16—C17—C180.3 (3)
S1—C4—C5—N253.68 (17)C9—C16—C17—C18179.79 (16)
S1—C4—C5—C8177.35 (12)C16—C17—C18—C190.1 (3)
S1—C4—C5—C658.57 (17)C17—C18—C19—C200.5 (3)
C1—N1—C6—C7145.36 (18)C18—C19—C20—C210.8 (3)
C3—N1—C6—C764.7 (2)C17—C16—C21—C200.1 (3)
C1—N1—C6—C593.6 (2)C9—C16—C21—C20179.83 (17)
C3—N1—C6—C556.4 (2)C19—C20—C21—C160.6 (3)
N2—C5—C6—N164.26 (16)C27—C22—C23—C240.4 (4)
C8—C5—C6—N1177.47 (14)C24—C25—C26—C270.6 (3)
C4—C5—C6—N154.80 (17)C26—C25—C24—C230.1 (3)
N2—C5—C6—C7175.46 (14)C22—C23—C24—C250.4 (3)
C8—C5—C6—C757.18 (18)C23—C22—C27—C260.1 (4)
C4—C5—C6—C765.48 (17)C25—C26—C27—C220.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4B···O1i0.992.363.266 (2)152
C8—H8A···O1i0.982.403.242 (2)143
C13—H13···O4ii0.952.483.263 (2)140
Symmetry codes: (i) x+1, y1/2, z+1; (ii) x+1, y+1/2, z+2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds