2-(Biphen­yl-4-yl)-3-(4-methoxy­phen­yl)-1,3-thia­zolidin-4-one

In the title mol­ecule, C₂₂H₁₉NO₂S, the thia­zolidinone ring exhibits a flattened envelope conformation. The methoxy­phen­yl and biphen­yl substituents are in pseudo-equatorial and pseudo-axial orientations, respectively, with respect to the thia­zolidinone ring.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.110
• Data-to-parameter ratio = 23.8

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.400
           From the CIF: _refine_ls_abs_structure_Flack_su    0.080
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero .......       0.40
PLAT128_ALERT_4_C Non-standard setting of Space group Pca21   ....    Pbc21
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        S14

Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
           From the CIF: _diffrn_reflns_theta_max           32.45
           From the CIF: _reflns_number_total               5640
           From the CIF: _diffrn_reflns_limit_ max hkl    9.   19.   27.
           From the CIF: _diffrn_reflns_limit_ min hkl   -9.  -19.  -27.
           TEST1: Expected hkl limits for theta max
           Calculated maximum hkl    9.   20.   33.
           Calculated minimum hkl   -9.  -20.  -33.
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           32.45
           From the CIF: _reflns_number_total               5640
           Count of symmetry unique reflns         3422
           Completeness (_total/calc)            164.82%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2218
           Fraction of Friedel pairs measured     0.648
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   2 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
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: Xpress (MacScience, 2002); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

2-(Biphenyl-4-yl)-3-(4-methoxyphenyl)-1,3-thiazolidin-4-one

Crystal data

C22H19NO2S	F(000) = 760
Mr = 361.44	Dx = 1.295 Mg m^−3
Orthorhombic, Pbc21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2b	Cell parameters from 5948 reflections
a = 6.2870 (5) Å	θ = 2.4–32.5°
b = 13.2480 (9) Å	µ = 0.19 mm^−1
c = 22.2500 (9) Å	T = 293 K
V = 1853.2 (2) Å^3	Block, pale yellow
Z = 4	0.35 × 0.2 × 0.2 mm

Data collection

DIPLabo 32001 diffractometer	4167 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.016
Graphite monochromator	θmax = 32.5°, θmin = 3.2°
Detector resolution: 10.0 pixels mm^-1	h = −9→9
IP scans	k = −19→19
5948 measured reflections	l = −27→27
5640 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.045	w = 1/[σ^2(Fo^2) + (0.0375P)^2 + 0.2616P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.110	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 0.19 e Å^−3
5640 reflections	Δρmin = −0.22 e Å^−3
237 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0111 (13)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2218 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.40 (8)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 (Ų)

	x	y	z	Uiso*/Ueq
S14	0.47430 (12)	0.84944 (4)	0.06480 (4)	0.0789 (2)
O17	0.0947 (2)	0.75915 (12)	0.18922 (8)	0.0709 (6)
O25	0.4577 (3)	0.36236 (13)	0.28651 (10)	0.0860 (7)
N18	0.3991 (2)	0.70609 (11)	0.14324 (7)	0.0513 (5)
C1	1.1412 (5)	0.3062 (2)	−0.08604 (14)	0.0916 (11)
C2	1.0788 (4)	0.30694 (19)	−0.14545 (12)	0.0767 (9)
C3	0.9339 (4)	0.37670 (18)	−0.16394 (12)	0.0725 (8)
C4	0.8498 (4)	0.44579 (16)	−0.12432 (9)	0.0626 (7)
C5	0.9093 (3)	0.44590 (14)	−0.06383 (9)	0.0541 (6)
C6	1.0576 (4)	0.3749 (2)	−0.04596 (12)	0.0821 (9)
C7	0.8203 (3)	0.52020 (13)	−0.02102 (9)	0.0504 (5)
C8	0.6089 (3)	0.55222 (14)	−0.02406 (9)	0.0551 (6)
C9	0.5297 (3)	0.62208 (15)	0.01663 (10)	0.0557 (6)
C10	0.6571 (3)	0.66175 (12)	0.06182 (10)	0.0511 (5)
C11	0.8650 (3)	0.63026 (14)	0.06461 (11)	0.0601 (6)
C12	0.9455 (3)	0.56024 (16)	0.02415 (10)	0.0597 (6)
C13	0.5765 (3)	0.74020 (13)	0.10568 (9)	0.0554 (6)
C15	0.2631 (4)	0.86795 (15)	0.11680 (11)	0.0711 (8)
C16	0.2412 (3)	0.77328 (13)	0.15415 (9)	0.0561 (6)
C19	0.4225 (3)	0.61685 (12)	0.17974 (8)	0.0472 (5)
C20	0.2706 (3)	0.54170 (14)	0.17699 (9)	0.0566 (6)
C21	0.2869 (3)	0.45739 (15)	0.21370 (10)	0.0616 (7)
C22	0.4570 (3)	0.44766 (14)	0.25192 (9)	0.0587 (6)
C23	0.6111 (4)	0.52147 (16)	0.25374 (10)	0.0644 (7)
C24	0.5933 (3)	0.60657 (15)	0.21775 (10)	0.0587 (6)
C26	0.6373 (5)	0.3434 (2)	0.32296 (14)	0.0990 (11)
H1	1.24100	0.25650	−0.07220	0.1100*
H2	1.13210	0.25670	−0.17270	0.0920*
H3	0.88860	0.37780	−0.20510	0.0870*
H4	0.75140	0.49470	−0.13980	0.0750*
H6	1.11050	0.37740	−0.00550	0.0990*
H8	0.51800	0.52410	−0.05440	0.0660*
H9	0.38430	0.64300	0.01220	0.0670*
H11	0.95900	0.65640	0.09490	0.0720*
H12	1.09110	0.53970	0.02850	0.0720*
H16A	0.13260	0.88280	0.09620	0.0850*
H16B	0.29920	0.92320	0.14280	0.0850*
H17	0.69580	0.75760	0.13060	0.0670*
H19	0.15580	0.54630	0.14870	0.0680*
H20	0.17630	0.40750	0.21230	0.0740*
H22	0.73370	0.51250	0.27890	0.0770*
H23	0.69930	0.65860	0.21970	0.0700*
H25A	0.60730	0.28160	0.34380	0.1190*
H25B	0.66380	0.39610	0.35160	0.1190*
H25C	0.76050	0.33450	0.29800	0.1190*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S14	0.1188 (5)	0.0443 (2)	0.0737 (3)	0.0094 (3)	0.0027 (4)	0.0155 (2)
O17	0.0682 (9)	0.0671 (9)	0.0773 (11)	0.0151 (7)	0.0001 (8)	−0.0061 (8)
O25	0.0953 (12)	0.0628 (9)	0.0998 (14)	0.0157 (8)	0.0109 (10)	0.0366 (9)
N18	0.0607 (9)	0.0398 (7)	0.0534 (9)	0.0053 (6)	−0.0037 (7)	0.0043 (6)
C1	0.103 (2)	0.0875 (18)	0.0843 (18)	0.0421 (16)	0.0040 (15)	0.0059 (14)
C2	0.0861 (16)	0.0649 (14)	0.0791 (16)	0.0041 (11)	0.0145 (13)	−0.0056 (11)
C3	0.0879 (16)	0.0680 (13)	0.0616 (14)	−0.0038 (11)	−0.0008 (11)	−0.0044 (10)
C4	0.0714 (13)	0.0589 (11)	0.0576 (12)	0.0032 (9)	−0.0093 (9)	0.0015 (8)
C5	0.0582 (10)	0.0503 (10)	0.0539 (11)	−0.0006 (8)	−0.0014 (8)	0.0083 (7)
C6	0.0983 (18)	0.0859 (16)	0.0622 (14)	0.0363 (14)	−0.0043 (12)	0.0052 (11)
C7	0.0533 (9)	0.0454 (8)	0.0524 (10)	−0.0034 (7)	−0.0042 (8)	0.0076 (7)
C8	0.0537 (10)	0.0539 (10)	0.0577 (11)	−0.0039 (8)	−0.0072 (8)	0.0006 (8)
C9	0.0465 (9)	0.0538 (10)	0.0668 (13)	−0.0020 (7)	−0.0038 (8)	0.0024 (8)
C10	0.0572 (10)	0.0430 (7)	0.0532 (9)	−0.0067 (7)	−0.0034 (8)	0.0069 (8)
C11	0.0607 (11)	0.0565 (10)	0.0632 (11)	−0.0026 (8)	−0.0161 (10)	0.0004 (10)
C12	0.0513 (10)	0.0617 (11)	0.0660 (12)	0.0024 (8)	−0.0084 (8)	0.0015 (9)
C13	0.0674 (11)	0.0419 (8)	0.0570 (11)	−0.0054 (8)	−0.0064 (8)	0.0056 (7)
C15	0.0930 (17)	0.0452 (9)	0.0750 (15)	0.0165 (10)	−0.0168 (11)	−0.0007 (9)
C16	0.0649 (11)	0.0430 (9)	0.0605 (11)	0.0083 (8)	−0.0153 (9)	−0.0066 (8)
C19	0.0542 (9)	0.0386 (7)	0.0489 (9)	0.0036 (6)	−0.0009 (8)	0.0011 (6)
C20	0.0570 (11)	0.0498 (9)	0.0630 (11)	−0.0012 (8)	−0.0066 (9)	0.0013 (8)
C21	0.0627 (12)	0.0469 (10)	0.0752 (13)	−0.0034 (8)	0.0048 (10)	0.0035 (8)
C22	0.0679 (12)	0.0448 (9)	0.0635 (12)	0.0101 (8)	0.0102 (9)	0.0114 (8)
C23	0.0687 (13)	0.0611 (11)	0.0635 (13)	0.0056 (9)	−0.0133 (10)	0.0105 (9)
C24	0.0617 (11)	0.0512 (9)	0.0633 (12)	−0.0043 (8)	−0.0125 (9)	0.0058 (8)
C26	0.113 (2)	0.097 (2)	0.0870 (18)	0.0434 (17)	0.0121 (16)	0.0399 (15)

Geometric parameters (Å, º)

S14—C13	1.8261 (19)	C19—C24	1.374 (3)
S14—C15	1.778 (3)	C20—C21	1.388 (3)
O17—C16	1.222 (2)	C21—C22	1.372 (3)
O25—C22	1.367 (3)	C22—C23	1.377 (3)
O25—C26	1.413 (4)	C23—C24	1.387 (3)
N18—C13	1.465 (2)	C1—H1	0.9602
N18—C16	1.355 (2)	C2—H2	0.9607
N18—C19	1.442 (2)	C3—H3	0.9592
C1—C2	1.379 (4)	C4—H4	0.9598
C1—C6	1.378 (4)	C6—H6	0.9603
C2—C3	1.361 (4)	C8—H8	0.9597
C3—C4	1.376 (3)	C9—H9	0.9603
C4—C5	1.397 (3)	C11—H11	0.9609
C5—C6	1.383 (3)	C12—H12	0.9599
C5—C7	1.480 (3)	C13—H17	0.9608
C7—C8	1.397 (3)	C15—H16A	0.9602
C7—C12	1.382 (3)	C15—H16B	0.9602
C8—C9	1.387 (3)	C20—H19	0.9596
C9—C10	1.389 (3)	C21—H20	0.9599
C10—C11	1.373 (3)	C23—H22	0.9600
C10—C13	1.513 (3)	C24—H23	0.9598
C11—C12	1.388 (3)	C26—H25A	0.9596
C15—C16	1.511 (3)	C26—H25B	0.9598
C19—C20	1.381 (3)	C26—H25C	0.9603
C13—S14—C15	92.75 (10)	C2—C1—H1	119.88
C22—O25—C26	118.21 (19)	C6—C1—H1	119.63
C13—N18—C16	117.21 (15)	C1—C2—H2	120.06
C13—N18—C19	119.77 (14)	C3—C2—H2	120.87
C16—N18—C19	120.82 (15)	C2—C3—H3	119.84
C2—C1—C6	120.5 (3)	C4—C3—H3	119.17
C1—C2—C3	119.0 (2)	C3—C4—H4	117.82
C2—C3—C4	121.0 (2)	C5—C4—H4	121.17
C3—C4—C5	121.0 (2)	C1—C6—H6	119.82
C4—C5—C6	117.2 (2)	C5—C6—H6	118.66
C4—C5—C7	121.31 (18)	C7—C8—H8	118.87
C6—C5—C7	121.49 (19)	C9—C8—H8	120.29
C1—C6—C5	121.3 (2)	C8—C9—H9	117.86
C5—C7—C8	122.05 (17)	C10—C9—H9	120.94
C5—C7—C12	120.53 (17)	C10—C11—H11	120.50
C8—C7—C12	117.42 (17)	C12—C11—H11	118.13
C7—C8—C9	120.84 (18)	C7—C12—H12	120.50
C8—C9—C10	121.20 (18)	C11—C12—H12	118.15
C9—C10—C11	117.82 (18)	S14—C13—H17	111.84
C9—C10—C13	122.26 (17)	N18—C13—H17	109.82
C11—C10—C13	119.88 (18)	C10—C13—H17	106.00
C10—C11—C12	121.4 (2)	S14—C15—H16A	110.84
C7—C12—C11	121.35 (18)	S14—C15—H16B	108.70
S14—C13—N18	105.11 (12)	C16—C15—H16A	110.78
S14—C13—C10	109.94 (14)	C16—C15—H16B	108.84
N18—C13—C10	114.27 (14)	H16A—C15—H16B	109.48
S14—C15—C16	108.15 (15)	C19—C20—H19	120.23
O17—C16—N18	124.48 (17)	C21—C20—H19	119.53
O17—C16—C15	123.18 (18)	C20—C21—H20	118.80
N18—C16—C15	112.33 (17)	C22—C21—H20	121.33
N18—C19—C20	119.71 (16)	C22—C23—H22	119.61
N18—C19—C24	120.52 (16)	C24—C23—H22	120.13
C20—C19—C24	119.76 (17)	C19—C24—H23	119.96
C19—C20—C21	120.21 (18)	C23—C24—H23	120.10
C20—C21—C22	119.86 (18)	O25—C26—H25A	105.78
O25—C22—C21	115.40 (18)	O25—C26—H25B	112.99
O25—C22—C23	124.62 (19)	O25—C26—H25C	109.54
C21—C22—C23	119.98 (19)	H25A—C26—H25B	109.51
C22—C23—C24	120.2 (2)	H25A—C26—H25C	109.46
C19—C24—C23	119.93 (18)	H25B—C26—H25C	109.47
C13—S14—C15—C16	−15.47 (16)	C4—C5—C7—C8	37.2 (3)
C15—S14—C13—C10	142.82 (14)	C5—C7—C12—C11	179.79 (19)
C15—S14—C13—N18	19.40 (14)	C8—C7—C12—C11	−0.6 (3)
C26—O25—C22—C23	−5.9 (3)	C12—C7—C8—C9	0.5 (3)
C26—O25—C22—C21	174.6 (2)	C5—C7—C8—C9	−179.92 (19)
C19—N18—C13—C10	56.4 (2)	C7—C8—C9—C10	−0.5 (3)
C13—N18—C19—C20	−129.29 (18)	C8—C9—C10—C13	178.24 (18)
C13—N18—C19—C24	51.5 (2)	C8—C9—C10—C11	0.6 (3)
C19—N18—C16—C15	171.95 (16)	C9—C10—C13—S14	−55.9 (2)
C16—N18—C13—C10	−140.33 (17)	C11—C10—C13—S14	121.69 (18)
C13—N18—C16—C15	8.8 (2)	C11—C10—C13—N18	−120.42 (19)
C16—N18—C19—C20	68.0 (2)	C9—C10—C13—N18	62.0 (2)
C13—N18—C16—O17	−172.44 (18)	C13—C10—C11—C12	−178.42 (19)
C19—N18—C16—O17	−9.3 (3)	C9—C10—C11—C12	−0.7 (3)
C19—N18—C13—S14	176.98 (13)	C10—C11—C12—C7	0.7 (3)
C16—N18—C13—S14	−19.72 (19)	S14—C15—C16—N18	7.0 (2)
C16—N18—C19—C24	−111.2 (2)	S14—C15—C16—O17	−171.74 (17)
C2—C1—C6—C5	0.2 (4)	C20—C19—C24—C23	−0.8 (3)
C6—C1—C2—C3	0.2 (4)	C24—C19—C20—C21	1.8 (3)
C1—C2—C3—C4	0.0 (4)	N18—C19—C20—C21	−177.36 (17)
C2—C3—C4—C5	−0.5 (4)	N18—C19—C24—C23	178.38 (18)
C3—C4—C5—C7	179.7 (2)	C19—C20—C21—C22	−1.4 (3)
C3—C4—C5—C6	0.9 (3)	C20—C21—C22—C23	0.0 (3)
C6—C5—C7—C12	35.6 (3)	C20—C21—C22—O25	179.53 (19)
C7—C5—C6—C1	−179.6 (2)	C21—C22—C23—C24	1.1 (3)
C4—C5—C7—C12	−143.2 (2)	O25—C22—C23—C24	−178.5 (2)
C6—C5—C7—C8	−144.0 (2)	C22—C23—C24—C19	−0.6 (3)
C4—C5—C6—C1	−0.7 (4)