4,6-Diphenyl-1-(phenyl­sulfon­yl)-1H-furo[3,4-b]pyrrole

Moskalev, N.V.; Gribble, G.W.; Jasinski, J.P.

doi:10.1107/S1600536807005764

4,6-Diphenyl-1-(phenylsulfonyl)-1H-furo[3,4-b]pyrrole

N. V. Moskalev, G. W. Gribble and J. P. Jasinski

The title molecule, C₂₄H₁₇NO₃S, is the first example of the 1H-furo[3,4-b]pyrrole ring system to be described. It crystallizes with three molecules in the asymmetric unit. In each molecule, the fused heterocycle is planar and one of the two phenyl groups on the furan ring is only slightly out of planarity with the furan ring, while the other phenyl group is significantly twisted by 47.6 (4), 48.3 (3) and 54.1 (3)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807005764/bv2045sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807005764/bv2045Isup2.hkl Contains datablock I

CCDC reference: 640288

checkCIF report

Key indicators

Single-crystal X-ray study
T = 29 K
Mean (C-C) = 0.014 Å
R factor = 0.043
wR factor = 0.151
Data-to-parameter ratio = 9.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         36 Perc.
PLAT331_ALERT_2_B Small Average Phenyl C-C Dist.   C8A    -C13A          1.36 Ang.
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         14

Alert level C
PLAT030_ALERT_1_C _diffrn_reflns_number .LE.  _reflns_number_total          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.94 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.71 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.72 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C12A
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C16C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C24C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C8A
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C8C
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C8B    -C13B          1.37 Ang.
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C20B   -C25B          1.37 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C24 H17 N O3 S

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           27.50
           From the CIF: _reflns_number_total               7146
           Count of symmetry unique reflns         6811
           Completeness (_total/calc)            104.92%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       335
           Fraction of Friedel pairs measured     0.049
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
  14 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994)); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: CrystalStructure.

4,6-Diphenyl-1-(phenylsulfonyl)-1H-furo[3,4-b]pyrrole top

Crystal data top

C₂₄H₁₇NO₃S	Z = 3
M_r = 399.46	F(000) = 624
Triclinic, P1	D_x = 1.343 Mg m⁻³
a = 10.508 (3) Å	Mo Kα radiation, λ = 0.71069 Å
b = 11.713 (3) Å	Cell parameters from 20 reflections
c = 12.250 (2) Å	θ = 6.2–7.7°
α = 92.424 (19)°	µ = 0.19 mm⁻¹
β = 92.08 (2)°	T = 29 K
γ = 100.00 (3)°	Prism, yellow
V = 1482.0 (7) Å³	0.60 × 0.50 × 0.40 mm

Data collection top

Rigaku AFC-6S diffractometer	2604 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 27.5°, θ_min = 1.7°
ω/2θ scans	h = −13→13
Absorption correction: ψ scan (North et al., 1968)	k = 0→15
T_min = 0.895, T_max = 0.928	l = −15→15
7146 measured reflections	3 standard reflections every 150 reflections
7146 independent reflections	intensity decay: 6.1%

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.043	w = 1/[σ²(F_o²) + (0.0518P)² + 0.2771P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.151	(Δ/σ)_max < 0.001
S = 0.99	Δρ_max = 0.20 e Å⁻³
7146 reflections	Δρ_min = −0.20 e Å⁻³
786 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
3 restraints	Extinction coefficient: 0.0177 (13)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with how many Friedel pairs?
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.12 (11)

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

	x	y	z	U_iso*/U_eq
S1A	1.0996 (2)	0.96481 (19)	−0.17687 (17)	0.0620 (6)
S1B	0.49610 (19)	0.45616 (17)	0.73326 (15)	0.0541 (6)
S1C	0.7270 (2)	0.6587 (2)	0.09593 (19)	0.0721 (7)
O1A	1.2102 (6)	1.0087 (5)	−0.2349 (4)	0.0782 (19)
O1C	0.8314 (5)	0.7352 (5)	0.1507 (5)	0.0901 (19)
O1B	0.3825 (5)	0.4301 (5)	0.7911 (4)	0.0696 (16)
O2C	0.6949 (7)	0.6668 (6)	−0.0163 (5)	0.103 (2)
O2A	0.9745 (6)	0.9710 (5)	−0.2208 (5)	0.0828 (19)
O2B	0.6172 (5)	0.4376 (5)	0.7780 (4)	0.0692 (17)
O3A	1.3887 (5)	1.0523 (5)	0.1311 (4)	0.0589 (15)
O3B	0.1909 (4)	0.3693 (4)	0.4381 (4)	0.0516 (14)
O3C	0.8552 (4)	0.4046 (4)	0.3560 (4)	0.0533 (13)
N1A	1.1157 (6)	1.0407 (6)	−0.0597 (6)	0.060 (2)
N1C	0.7603 (6)	0.5262 (5)	0.1074 (5)	0.0621 (17)
N1B	0.4720 (6)	0.3753 (5)	0.6174 (5)	0.0516 (17)
C2A	1.0094 (9)	1.0335 (8)	0.0061 (9)	0.081 (3)
H1	0.9248	1.0259	−0.0221	0.097*
C2B	0.5777 (7)	0.3771 (7)	0.5463 (7)	0.053 (2)
H18	0.6634	0.3814	0.5706	0.063*
C2C	0.7017 (8)	0.4331 (9)	0.0374 (7)	0.075 (2)
H35	0.6659	0.4411	−0.0317	0.090*
C3B	0.5397 (7)	0.3721 (7)	0.4441 (7)	0.050 (2)
H19	0.5916	0.3691	0.3846	0.060*
C3C	0.7033 (8)	0.3298 (8)	0.0823 (7)	0.069 (2)
H36	0.6709	0.2565	0.0507	0.082*
C3A	1.0404 (9)	1.0387 (8)	0.1160 (9)	0.074 (3)
H2	0.9839	1.0373	0.1728	0.088*
C4B	0.4030 (7)	0.3721 (7)	0.4392 (6)	0.048 (2)
C4A	1.1777 (8)	1.0466 (7)	0.1252 (7)	0.056 (2)
C4C	0.7659 (7)	0.3571 (7)	0.1901 (7)	0.056 (2)
C5A	1.2830 (8)	1.0541 (7)	0.1944 (8)	0.062 (3)
C5C	0.8012 (7)	0.3105 (7)	0.2862 (6)	0.046 (2)
C5B	0.2930 (8)	0.3685 (7)	0.3735 (6)	0.047 (2)
C6B	0.2312 (7)	0.3701 (7)	0.5462 (6)	0.047 (2)
C6A	1.3511 (8)	1.0501 (7)	0.0208 (6)	0.052 (2)
C6C	0.8574 (7)	0.5077 (6)	0.3044 (6)	0.0522 (19)
C7A	1.2213 (7)	1.0457 (7)	0.0177 (7)	0.050 (2)
C7C	0.7994 (7)	0.4786 (7)	0.2052 (6)	0.051 (2)
C7B	0.3600 (7)	0.3754 (6)	0.5480 (6)	0.0417 (19)
C8C	0.5905 (8)	0.6602 (6)	0.1708 (8)	0.063 (2)
C8B	0.5146 (9)	0.5996 (7)	0.6931 (6)	0.059 (2)
C8A	1.1072 (8)	0.8237 (7)	−0.1471 (6)	0.057 (2)
C9A	1.2207 (10)	0.7880 (9)	−0.1438 (7)	0.081 (3)
H3	1.2959	0.8400	−0.1557	0.097*
C9C	0.6033 (9)	0.6730 (8)	0.2839 (8)	0.081 (3)
H37	0.6841	0.6807	0.3197	0.097*
C9B	0.4074 (10)	0.6457 (9)	0.6594 (7)	0.080 (3)
H20	0.3255	0.6000	0.6580	0.096*
C10B	0.4212 (15)	0.7581 (11)	0.6282 (9)	0.110 (4)
H21	0.3503	0.7893	0.6038	0.132*
C10A	1.2275 (15)	0.6762 (14)	−0.1232 (11)	0.126 (5)
H4	1.3061	0.6508	−0.1291	0.151*
C10C	0.4949 (13)	0.6740 (9)	0.3415 (10)	0.103 (3)
H38	0.5031	0.6808	0.4175	0.123*
C11B	0.5427 (16)	0.8222 (10)	0.6342 (9)	0.111 (4)
H22	0.5531	0.8990	0.6145	0.133*
C11C	0.3763 (14)	0.6656 (10)	0.2929 (13)	0.119 (4)
H39	0.3045	0.6679	0.3346	0.143*
C11A	1.126 (2)	0.6027 (14)	−0.0951 (10)	0.141 (7)
H5	1.1345	0.5287	−0.0750	0.169*
C12B	0.6459 (12)	0.7813 (10)	0.6663 (10)	0.110 (4)
H23	0.7264	0.8294	0.6694	0.132*
C12C	0.3630 (11)	0.6536 (10)	0.1811 (15)	0.125 (4)
H40	0.2815	0.6473	0.1467	0.150*
C12A	1.0083 (18)	0.6357 (11)	−0.0957 (11)	0.144 (6)
H6	0.9353	0.5835	−0.0785	0.173*
C13B	0.6356 (10)	0.6678 (9)	0.6954 (9)	0.082 (3)
H24	0.7087	0.6379	0.7161	0.098*
C13C	0.4720 (11)	0.6508 (9)	0.1177 (9)	0.100 (3)
H41	0.4636	0.6428	0.0418	0.120*
C13A	0.9972 (11)	0.7503 (10)	−0.1226 (9)	0.103 (4)
H7	0.9176	0.7747	−0.1236	0.124*
C14A	1.3058 (9)	1.0617 (7)	0.3117 (7)	0.057 (2)
C14C	0.8002 (7)	0.1975 (7)	0.3240 (7)	0.058 (2)
C14B	0.2665 (8)	0.3594 (7)	0.2573 (7)	0.048 (2)
C15A	1.4279 (10)	1.0567 (9)	0.3586 (8)	0.076 (3)
H8	1.4953	1.0462	0.3142	0.091*
C15C	0.8489 (8)	0.1810 (7)	0.4290 (8)	0.075 (2)
H42	0.8825	0.2447	0.4756	0.090*
C15B	0.1442 (9)	0.3621 (8)	0.2117 (7)	0.066 (2)
H25	0.0765	0.3693	0.2568	0.079*
C16A	1.4483 (11)	1.0672 (9)	0.4710 (8)	0.087 (3)
H9	1.5301	1.0671	0.5026	0.104*
C16C	0.8469 (10)	0.0704 (10)	0.4632 (11)	0.104 (4)
H43	0.8800	0.0609	0.5331	0.125*
C16B	0.1230 (9)	0.3543 (8)	0.0997 (7)	0.073 (3)
H26	0.0401	0.3551	0.0708	0.088*
C17A	1.3460 (11)	1.0780 (8)	0.5354 (8)	0.079 (3)
H10	1.3580	1.0800	0.6111	0.095*
C17B	0.2194 (10)	0.3455 (8)	0.0296 (7)	0.067 (2)
H27	0.2025	0.3390	−0.0456	0.081*
C17C	0.7980 (10)	−0.0261 (10)	0.3982 (12)	0.102 (4)
H44	0.7955	−0.1003	0.4232	0.123*
C18A	1.2247 (10)	1.0861 (7)	0.4896 (8)	0.069 (3)
H11	1.1570	1.0968	0.5335	0.083*
C18C	0.7528 (10)	−0.0096 (8)	0.2949 (11)	0.090 (3)
H45	0.7215	−0.0739	0.2483	0.107*
C18B	0.3383 (9)	0.3463 (8)	0.0720 (7)	0.066 (2)
H28	0.4058	0.3443	0.0252	0.079*
C19A	1.2085 (9)	1.0778 (7)	0.3795 (7)	0.064 (2)
H12	1.1279	1.0832	0.3482	0.077*
C19C	0.7524 (8)	0.1002 (7)	0.2581 (8)	0.070 (3)
H46	0.7195	0.1086	0.1879	0.084*
C19B	0.3638 (8)	0.3500 (7)	0.1848 (7)	0.063 (2)
H29	0.4467	0.3463	0.2119	0.076*
C20B	0.1299 (7)	0.3650 (7)	0.6246 (6)	0.0414 (18)
C20A	1.4603 (7)	1.0526 (7)	−0.0523 (6)	0.052 (2)
C20C	0.9190 (7)	0.6118 (6)	0.3727 (7)	0.057 (2)
C21C	0.8845 (8)	0.6285 (7)	0.4777 (6)	0.065 (2)
H47	0.8170	0.5780	0.5064	0.078*
C21A	1.4770 (8)	1.1280 (7)	−0.1363 (7)	0.065 (2)
H13	1.4170	1.1761	−0.1493	0.078*
C21B	0.0391 (7)	0.4344 (8)	0.6130 (7)	0.057 (2)
H30	0.0467	0.4883	0.5590	0.069*
C22C	0.9520 (10)	0.7219 (8)	0.5409 (9)	0.084 (3)
H48	0.9290	0.7331	0.6126	0.100*
C22B	−0.0631 (9)	0.4255 (8)	0.6801 (7)	0.071 (3)
H31	−0.1242	0.4736	0.6719	0.086*
C22A	1.5829 (10)	1.1324 (9)	−0.2012 (8)	0.081 (3)
H14	1.5942	1.1844	−0.2568	0.098*
C23C	1.0493 (10)	0.7968 (8)	0.5022 (10)	0.091 (3)
H49	1.0939	0.8576	0.5474	0.109*
C23B	−0.0753 (8)	0.3463 (9)	0.7588 (7)	0.071 (3)
H32	−0.1455	0.3394	0.8036	0.085*
C23A	1.6715 (9)	1.0602 (10)	−0.1841 (9)	0.081 (3)
H15	1.7425	1.0629	−0.2276	0.098*
C24C	1.0830 (10)	0.7835 (8)	0.3948 (11)	0.100 (4)
H50	1.1476	0.8373	0.3665	0.120*
C24A	1.6529 (8)	0.9850 (9)	−0.1022 (9)	0.076 (3)
H16	1.7124	0.9362	−0.0901	0.091*
C24B	0.0153 (8)	0.2772 (8)	0.7720 (7)	0.061 (2)
H33	0.0073	0.2233	0.8260	0.073*
C25A	1.5483 (8)	0.9792 (8)	−0.0366 (7)	0.066 (2)
H17	1.5369	0.9260	0.0179	0.080*
C25B	0.1176 (8)	0.2871 (7)	0.7059 (6)	0.054 (2)
H34	0.1799	0.2406	0.7158	0.065*
C25C	1.0200 (8)	0.6898 (8)	0.3300 (8)	0.080 (3)
H51	1.0443	0.6783	0.2586	0.096*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1A	0.0645 (16)	0.0614 (15)	0.0588 (14)	0.0089 (12)	−0.0068 (13)	0.0067 (12)
S1B	0.0574 (14)	0.0593 (14)	0.0456 (12)	0.0122 (11)	−0.0051 (11)	0.0015 (11)
S1C	0.0837 (17)	0.0683 (15)	0.0666 (15)	0.0147 (13)	0.0055 (12)	0.0228 (12)
O1A	0.082 (4)	0.092 (5)	0.053 (3)	−0.009 (4)	0.011 (3)	0.013 (3)
O1C	0.082 (4)	0.065 (4)	0.118 (5)	−0.007 (3)	0.008 (4)	0.024 (4)
O1B	0.069 (4)	0.086 (4)	0.052 (3)	0.010 (3)	0.009 (3)	−0.001 (3)
O2C	0.132 (6)	0.112 (6)	0.072 (5)	0.033 (5)	0.013 (4)	0.046 (4)
O2A	0.080 (5)	0.074 (5)	0.093 (5)	0.018 (3)	−0.032 (4)	0.002 (4)
O2B	0.065 (4)	0.074 (4)	0.067 (4)	0.014 (3)	−0.021 (3)	0.008 (3)
O3A	0.056 (4)	0.067 (4)	0.052 (4)	0.008 (3)	−0.002 (3)	0.004 (3)
O3B	0.044 (3)	0.072 (4)	0.039 (3)	0.009 (3)	0.008 (3)	0.007 (3)
O3C	0.050 (3)	0.047 (3)	0.063 (3)	0.008 (2)	−0.003 (2)	0.007 (3)
N1A	0.039 (4)	0.065 (5)	0.077 (5)	0.017 (3)	−0.002 (4)	0.002 (4)
N1C	0.077 (4)	0.058 (4)	0.054 (4)	0.020 (4)	−0.001 (3)	0.001 (3)
N1B	0.050 (4)	0.047 (4)	0.059 (4)	0.010 (3)	0.003 (4)	0.002 (3)
C2A	0.053 (6)	0.081 (7)	0.106 (9)	0.008 (5)	−0.004 (6)	−0.014 (6)
C2B	0.036 (5)	0.073 (6)	0.051 (5)	0.015 (4)	0.005 (4)	−0.001 (4)
C2C	0.079 (6)	0.088 (7)	0.060 (5)	0.024 (5)	−0.004 (5)	−0.005 (5)
C3B	0.041 (5)	0.060 (5)	0.050 (5)	0.010 (4)	0.014 (4)	−0.008 (4)
C3C	0.069 (6)	0.066 (6)	0.068 (6)	0.012 (5)	−0.007 (5)	−0.018 (5)
C3A	0.062 (6)	0.067 (6)	0.091 (8)	0.004 (5)	0.024 (6)	0.000 (6)
C4B	0.053 (5)	0.052 (5)	0.039 (5)	0.007 (4)	0.003 (4)	0.007 (4)
C4A	0.042 (6)	0.057 (6)	0.068 (7)	0.007 (4)	0.011 (5)	−0.006 (5)
C4C	0.043 (5)	0.046 (5)	0.077 (6)	0.007 (4)	0.008 (4)	−0.003 (4)
C5A	0.046 (5)	0.055 (6)	0.087 (7)	0.005 (4)	0.030 (6)	0.006 (5)
C5C	0.040 (4)	0.039 (5)	0.059 (5)	0.006 (4)	0.003 (4)	−0.003 (4)
C5B	0.062 (5)	0.053 (5)	0.027 (4)	0.012 (4)	0.006 (4)	0.007 (4)
C6B	0.044 (5)	0.065 (5)	0.034 (5)	0.017 (4)	−0.001 (4)	0.003 (4)
C6A	0.057 (6)	0.047 (5)	0.050 (5)	0.001 (4)	−0.003 (5)	0.002 (4)
C6C	0.050 (5)	0.046 (5)	0.062 (5)	0.012 (4)	0.001 (4)	0.006 (4)
C7A	0.031 (5)	0.046 (5)	0.071 (6)	0.006 (4)	0.006 (5)	0.002 (4)
C7C	0.052 (5)	0.045 (5)	0.061 (5)	0.019 (4)	0.009 (4)	0.007 (4)
C7B	0.051 (5)	0.039 (5)	0.034 (5)	0.005 (4)	−0.003 (4)	0.004 (3)
C8C	0.067 (6)	0.046 (5)	0.080 (7)	0.019 (4)	−0.004 (5)	0.007 (4)
C8B	0.075 (6)	0.060 (6)	0.045 (5)	0.022 (5)	0.000 (4)	−0.008 (4)
C8A	0.061 (5)	0.055 (5)	0.057 (5)	0.020 (5)	−0.002 (4)	−0.003 (4)
C9A	0.103 (8)	0.062 (6)	0.084 (7)	0.039 (5)	−0.007 (6)	−0.009 (5)
C9C	0.082 (7)	0.084 (7)	0.083 (7)	0.030 (5)	0.007 (6)	0.001 (5)
C9B	0.090 (7)	0.077 (7)	0.073 (6)	0.024 (6)	−0.016 (5)	−0.008 (5)
C10B	0.174 (13)	0.073 (8)	0.088 (8)	0.047 (8)	−0.037 (8)	−0.017 (6)
C10A	0.154 (13)	0.142 (14)	0.101 (10)	0.083 (11)	0.018 (9)	−0.011 (9)
C10C	0.114 (9)	0.101 (8)	0.100 (8)	0.035 (7)	0.026 (8)	−0.008 (6)
C11B	0.178 (14)	0.063 (8)	0.094 (8)	0.035 (9)	−0.016 (9)	0.003 (6)
C11C	0.122 (12)	0.102 (9)	0.141 (12)	0.033 (8)	0.033 (10)	−0.001 (9)
C11A	0.25 (2)	0.118 (14)	0.088 (9)	0.114 (15)	0.033 (12)	0.035 (9)
C12B	0.122 (10)	0.057 (8)	0.146 (11)	0.002 (7)	0.007 (8)	0.002 (7)
C12C	0.072 (8)	0.109 (10)	0.192 (15)	0.015 (6)	0.004 (9)	−0.001 (10)
C12A	0.233 (19)	0.058 (9)	0.135 (12)	−0.011 (9)	0.085 (12)	0.016 (8)
C13B	0.070 (6)	0.063 (6)	0.111 (8)	0.010 (5)	0.005 (5)	−0.008 (6)
C13C	0.108 (9)	0.097 (8)	0.096 (8)	0.021 (7)	−0.015 (7)	0.008 (6)
C13A	0.110 (9)	0.068 (8)	0.132 (10)	0.010 (7)	0.037 (7)	0.008 (7)
C14A	0.063 (6)	0.057 (6)	0.049 (5)	−0.003 (4)	0.014 (5)	0.013 (4)
C14C	0.041 (4)	0.044 (5)	0.090 (7)	0.006 (4)	0.010 (5)	0.007 (5)
C14B	0.048 (5)	0.049 (5)	0.047 (5)	0.008 (4)	0.004 (4)	−0.001 (4)
C15A	0.069 (6)	0.101 (8)	0.062 (7)	0.022 (6)	0.020 (5)	0.018 (6)
C15C	0.069 (6)	0.047 (5)	0.105 (7)	0.000 (4)	−0.010 (5)	0.015 (5)
C15B	0.067 (6)	0.088 (7)	0.046 (5)	0.016 (5)	0.002 (5)	0.012 (5)
C16A	0.093 (8)	0.117 (9)	0.047 (6)	0.013 (7)	−0.011 (6)	0.009 (6)
C16C	0.084 (8)	0.071 (8)	0.154 (11)	0.004 (6)	−0.018 (7)	0.026 (8)
C16B	0.068 (6)	0.093 (8)	0.058 (6)	0.014 (5)	−0.004 (5)	0.006 (5)
C17A	0.098 (8)	0.077 (7)	0.056 (6)	−0.001 (6)	0.006 (6)	0.004 (5)
C17B	0.082 (7)	0.074 (7)	0.047 (5)	0.017 (5)	0.001 (5)	0.009 (5)
C17C	0.079 (8)	0.074 (9)	0.161 (13)	0.023 (6)	0.019 (8)	0.036 (9)
C18A	0.088 (7)	0.051 (5)	0.064 (7)	−0.002 (5)	0.027 (6)	0.003 (5)
C18C	0.087 (7)	0.033 (6)	0.151 (10)	0.013 (5)	0.038 (7)	0.001 (6)
C18B	0.059 (6)	0.091 (7)	0.049 (6)	0.013 (5)	0.013 (5)	−0.002 (5)
C19A	0.073 (6)	0.059 (6)	0.059 (6)	0.006 (4)	0.018 (5)	−0.004 (5)
C19C	0.057 (6)	0.048 (6)	0.101 (7)	0.001 (4)	0.016 (5)	−0.011 (5)
C19B	0.059 (5)	0.064 (6)	0.062 (6)	0.001 (4)	−0.003 (5)	0.005 (5)
C20B	0.031 (4)	0.052 (5)	0.040 (4)	0.007 (4)	−0.001 (4)	−0.003 (4)
C20A	0.046 (5)	0.056 (5)	0.050 (5)	0.002 (4)	0.004 (4)	0.001 (4)
C20C	0.052 (5)	0.037 (4)	0.079 (6)	0.000 (4)	−0.013 (4)	0.002 (4)
C21C	0.084 (6)	0.057 (5)	0.051 (5)	0.002 (4)	−0.005 (4)	0.000 (4)
C21A	0.067 (6)	0.067 (6)	0.060 (6)	0.010 (5)	0.001 (5)	0.002 (5)
C21B	0.041 (5)	0.081 (6)	0.053 (5)	0.017 (5)	0.006 (4)	0.017 (4)
C22C	0.099 (8)	0.051 (6)	0.094 (7)	0.004 (6)	−0.027 (6)	−0.014 (6)
C22B	0.066 (6)	0.089 (7)	0.065 (6)	0.030 (5)	0.006 (5)	0.003 (5)
C22A	0.074 (7)	0.086 (8)	0.080 (7)	−0.003 (6)	0.028 (6)	0.014 (6)
C23C	0.089 (7)	0.055 (6)	0.122 (9)	0.013 (6)	−0.035 (7)	−0.029 (6)
C23B	0.049 (6)	0.091 (7)	0.071 (6)	0.008 (5)	0.031 (5)	−0.006 (6)
C23A	0.062 (7)	0.092 (8)	0.083 (8)	−0.006 (6)	0.015 (6)	−0.005 (6)
C24C	0.089 (8)	0.050 (6)	0.155 (11)	−0.006 (5)	0.010 (8)	−0.014 (7)
C24A	0.043 (6)	0.092 (8)	0.093 (8)	0.018 (5)	0.001 (5)	−0.013 (6)
C24B	0.069 (6)	0.060 (6)	0.051 (5)	0.002 (5)	0.008 (5)	0.011 (4)
C25A	0.057 (6)	0.067 (6)	0.075 (6)	0.012 (5)	0.000 (5)	−0.001 (5)
C25B	0.052 (5)	0.068 (6)	0.046 (5)	0.017 (4)	0.014 (4)	0.009 (4)
C25C	0.070 (6)	0.074 (7)	0.094 (7)	0.006 (5)	0.023 (5)	0.006 (5)

Geometric parameters (Å, º) top

S1A—O1A	1.416 (6)	C12B—C13B	1.378 (14)
S1A—O2A	1.416 (6)	C12B—H23	0.9300
S1A—N1A	1.644 (7)	C12C—C13C	1.412 (15)
S1A—C8A	1.722 (9)	C12C—H40	0.9300
S1B—O1B	1.405 (5)	C12A—C13A	1.419 (16)
S1B—O2B	1.422 (5)	C12A—H6	0.9300
S1B—N1B	1.658 (7)	C13B—H24	0.9300
S1B—C8B	1.751 (9)	C13C—H41	0.9300
S1C—O2C	1.415 (6)	C13A—H7	0.9300
S1C—O1C	1.418 (6)	C14A—C19A	1.373 (11)
S1C—N1C	1.659 (6)	C14A—C15A	1.399 (11)
S1C—C8C	1.732 (8)	C14C—C19C	1.377 (10)
O3A—C5A	1.380 (9)	C14C—C15C	1.401 (10)
O3A—C6A	1.393 (8)	C14B—C15B	1.388 (10)
O3B—C5B	1.356 (8)	C14B—C19B	1.394 (10)
O3B—C6B	1.375 (8)	C15A—C16A	1.383 (12)
O3C—C6C	1.384 (8)	C15A—H8	0.9300
O3C—C5C	1.391 (8)	C15C—C16C	1.375 (13)
N1A—C2A	1.395 (10)	C15C—H42	0.9300
N1A—C7A	1.425 (9)	C15B—C16B	1.378 (11)
N1C—C2C	1.398 (10)	C15B—H25	0.9300
N1C—C7C	1.419 (9)	C16A—C17A	1.377 (13)
N1B—C7B	1.428 (9)	C16A—H9	0.9300
N1B—C2B	1.435 (9)	C16C—C17C	1.367 (14)
C2A—C3A	1.369 (13)	C16C—H43	0.9300
C2A—H1	0.9300	C16B—C17B	1.365 (12)
C2B—C3B	1.296 (10)	C16B—H26	0.9300
C2B—H18	0.9300	C17A—C18A	1.393 (12)
C2C—C3C	1.352 (12)	C17A—H10	0.9300
C2C—H35	0.9300	C17B—C18B	1.334 (11)
C3B—C4B	1.435 (10)	C17B—H27	0.9300
C3B—H19	0.9300	C17C—C18C	1.369 (14)
C3C—C4C	1.451 (11)	C17C—H44	0.9300
C3C—H36	0.9300	C18A—C19A	1.351 (11)
C3A—C4A	1.430 (11)	C18A—H11	0.9300
C3A—H2	0.9300	C18C—C19C	1.381 (12)
C4B—C5B	1.377 (10)	C18C—H45	0.9300
C4B—C7B	1.424 (9)	C18B—C19B	1.396 (11)
C4A—C5A	1.357 (11)	C18B—H28	0.9300
C4A—C7A	1.410 (10)	C19A—H12	0.9300
C4C—C5C	1.384 (10)	C19C—H46	0.9300
C4C—C7C	1.408 (10)	C19B—H29	0.9300
C5A—C14A	1.444 (12)	C20B—C21B	1.364 (10)
C5C—C14C	1.418 (10)	C20B—C25B	1.373 (10)
C5B—C14B	1.437 (10)	C20A—C21A	1.380 (11)
C6B—C7B	1.343 (10)	C20A—C25A	1.382 (11)
C6B—C20B	1.455 (10)	C20C—C21C	1.365 (10)
C6A—C7A	1.355 (10)	C20C—C25C	1.407 (11)
C6A—C20A	1.478 (10)	C21C—C22C	1.385 (11)
C6C—C7C	1.343 (10)	C21C—H47	0.9300
C6C—C20C	1.485 (10)	C21A—C22A	1.386 (12)
C8C—C13C	1.368 (12)	C21A—H13	0.9300
C8C—C9C	1.387 (11)	C21B—C22B	1.368 (11)
C8B—C13B	1.377 (12)	C21B—H30	0.9300
C8B—C9B	1.389 (11)	C22C—C23C	1.341 (13)
C8A—C9A	1.331 (11)	C22C—H48	0.9300
C8A—C13A	1.366 (12)	C22B—C23B	1.359 (12)
C9A—C10A	1.358 (16)	C22B—H31	0.9300
C9A—H3	0.9300	C22A—C23A	1.378 (13)
C9C—C10C	1.363 (13)	C22A—H14	0.9300
C9C—H37	0.9300	C23C—C24C	1.385 (14)
C9B—C10B	1.371 (15)	C23C—H49	0.9300
C9B—H20	0.9300	C23B—C24B	1.363 (11)
C10B—C11B	1.362 (15)	C23B—H32	0.9300
C10B—H21	0.9300	C23A—C24A	1.360 (13)
C10A—C11A	1.316 (19)	C23A—H15	0.9300
C10A—H4	0.9300	C24C—C25C	1.382 (12)
C10C—C11C	1.348 (15)	C24C—H50	0.9300
C10C—H38	0.9300	C24A—C25A	1.379 (12)
C11B—C12B	1.313 (15)	C24A—H16	0.9300
C11B—H22	0.9300	C24B—C25B	1.361 (10)
C11C—C12C	1.370 (16)	C24B—H33	0.9300
C11C—H39	0.9300	C25A—H17	0.9300
C11A—C12A	1.36 (2)	C25B—H34	0.9300
C11A—H5	0.9300	C25C—H51	0.9300

O1A—S1A—O2A	120.0 (4)	C11C—C12C—C13C	120.5 (12)
O1A—S1A—N1A	105.5 (4)	C11C—C12C—H40	119.8
O2A—S1A—N1A	106.0 (4)	C13C—C12C—H40	119.8
O1A—S1A—C8A	108.2 (4)	C11A—C12A—C13A	119.6 (13)
O2A—S1A—C8A	109.6 (4)	C11A—C12A—H6	120.2
N1A—S1A—C8A	106.8 (4)	C13A—C12A—H6	120.2
O1B—S1B—O2B	121.3 (4)	C12B—C13B—C8B	118.6 (10)
O1B—S1B—N1B	106.7 (3)	C12B—C13B—H24	120.7
O2B—S1B—N1B	105.1 (3)	C8B—C13B—H24	120.7
O1B—S1B—C8B	109.4 (4)	C8C—C13C—C12C	118.3 (11)
O2B—S1B—C8B	108.2 (4)	C8C—C13C—H41	120.8
N1B—S1B—C8B	104.9 (4)	C12C—C13C—H41	120.8
O2C—S1C—O1C	122.0 (4)	C8A—C13A—C12A	118.0 (11)
O2C—S1C—N1C	105.5 (4)	C8A—C13A—H7	121.0
O1C—S1C—N1C	105.9 (4)	C12A—C13A—H7	121.0
O2C—S1C—C8C	109.4 (4)	C19A—C14A—C15A	118.6 (9)
O1C—S1C—C8C	108.0 (4)	C19A—C14A—C5A	120.4 (9)
N1C—S1C—C8C	104.8 (3)	C15A—C14A—C5A	121.0 (8)
C5A—O3A—C6A	109.9 (6)	C19C—C14C—C15C	117.7 (8)
C5B—O3B—C6B	109.8 (5)	C19C—C14C—C5C	121.0 (8)
C6C—O3C—C5C	110.7 (5)	C15C—C14C—C5C	121.2 (8)
C2A—N1A—C7A	103.0 (7)	C15B—C14B—C19B	116.8 (8)
C2A—N1A—S1A	118.5 (6)	C15B—C14B—C5B	121.9 (8)
C7A—N1A—S1A	124.5 (6)	C19B—C14B—C5B	121.3 (7)
C2C—N1C—C7C	107.0 (6)	C16A—C15A—C14A	119.9 (9)
C2C—N1C—S1C	121.8 (6)	C16A—C15A—H8	120.0
C7C—N1C—S1C	126.1 (5)	C14A—C15A—H8	120.0
C7B—N1B—C2B	106.0 (6)	C16C—C15C—C14C	119.9 (9)
C7B—N1B—S1B	120.7 (5)	C16C—C15C—H42	120.0
C2B—N1B—S1B	118.5 (5)	C14C—C15C—H42	120.0
C3A—C2A—N1A	114.1 (8)	C16B—C15B—C14B	120.1 (8)
C3A—C2A—H1	123.0	C16B—C15B—H25	119.9
N1A—C2A—H1	123.0	C14B—C15B—H25	119.9
C3B—C2B—N1B	112.0 (7)	C17A—C16A—C15A	119.1 (9)
C3B—C2B—H18	124.0	C17A—C16A—H9	120.5
N1B—C2B—H18	124.0	C15A—C16A—H9	120.5
C3C—C2C—N1C	111.9 (8)	C17C—C16C—C15C	122.3 (11)
C3C—C2C—H35	124.0	C17C—C16C—H43	118.9
N1C—C2C—H35	124.0	C15C—C16C—H43	118.9
C2B—C3B—C4B	107.8 (7)	C17B—C16B—C15B	122.4 (9)
C2B—C3B—H19	126.1	C17B—C16B—H26	118.8
C4B—C3B—H19	126.1	C15B—C16B—H26	118.8
C2C—C3C—C4C	105.8 (8)	C16A—C17A—C18A	121.4 (9)
C2C—C3C—H36	127.1	C16A—C17A—H10	119.3
C4C—C3C—H36	127.1	C18A—C17A—H10	119.3
C2A—C3A—C4A	105.7 (8)	C18B—C17B—C16B	118.3 (9)
C2A—C3A—H2	127.1	C18B—C17B—H27	120.9
C4A—C3A—H2	127.1	C16B—C17B—H27	120.9
C5B—C4B—C7B	104.8 (6)	C16C—C17C—C18C	117.6 (11)
C5B—C4B—C3B	146.8 (7)	C16C—C17C—H44	121.2
C7B—C4B—C3B	108.5 (7)	C18C—C17C—H44	121.2
C5A—C4A—C7A	107.4 (7)	C19A—C18A—C17A	118.0 (9)
C5A—C4A—C3A	145.9 (9)	C19A—C18A—H11	121.0
C7A—C4A—C3A	106.7 (8)	C17A—C18A—H11	121.0
C5C—C4C—C7C	107.1 (7)	C17C—C18C—C19C	121.7 (11)
C5C—C4C—C3C	144.4 (8)	C17C—C18C—H45	119.2
C7C—C4C—C3C	108.4 (7)	C19C—C18C—H45	119.2
C4A—C5A—O3A	107.3 (8)	C17B—C18B—C19B	121.5 (8)
C4A—C5A—C14A	135.5 (8)	C17B—C18B—H28	119.3
O3A—C5A—C14A	117.3 (8)	C19B—C18B—H28	119.3
C4C—C5C—O3C	105.8 (6)	C18A—C19A—C14A	122.9 (9)
C4C—C5C—C14C	136.3 (8)	C18A—C19A—H12	118.5
O3C—C5C—C14C	117.8 (7)	C14A—C19A—H12	118.5
O3B—C5B—C4B	108.8 (6)	C14C—C19C—C18C	120.8 (10)
O3B—C5B—C14B	117.2 (7)	C14C—C19C—H46	119.6
C4B—C5B—C14B	133.9 (7)	C18C—C19C—H46	119.6
C7B—C6B—O3B	106.5 (6)	C14B—C19B—C18B	120.8 (8)
C7B—C6B—C20B	137.8 (7)	C14B—C19B—H29	119.6
O3B—C6B—C20B	115.7 (6)	C18B—C19B—H29	119.6
C7A—C6A—O3A	105.7 (7)	C21B—C20B—C25B	118.6 (7)
C7A—C6A—C20A	141.2 (8)	C21B—C20B—C6B	119.1 (7)
O3A—C6A—C20A	113.1 (7)	C25B—C20B—C6B	122.1 (7)
C7C—C6C—O3C	106.0 (6)	C21A—C20A—C25A	118.9 (8)
C7C—C6C—C20C	140.4 (7)	C21A—C20A—C6A	121.1 (8)
O3C—C6C—C20C	113.6 (6)	C25A—C20A—C6A	120.0 (8)
C6A—C7A—C4A	109.6 (7)	C21C—C20C—C25C	120.0 (7)
C6A—C7A—N1A	139.9 (8)	C21C—C20C—C6C	120.9 (7)
C4A—C7A—N1A	110.5 (6)	C25C—C20C—C6C	118.9 (8)
C6C—C7C—C4C	110.3 (7)	C20C—C21C—C22C	118.7 (8)
C6C—C7C—N1C	142.8 (7)	C20C—C21C—H47	120.7
C4C—C7C—N1C	106.9 (7)	C22C—C21C—H47	120.7
C6B—C7B—C4B	110.0 (7)	C20A—C21A—C22A	120.3 (9)
C6B—C7B—N1B	144.1 (7)	C20A—C21A—H13	119.9
C4B—C7B—N1B	105.7 (6)	C22A—C21A—H13	119.9
C13C—C8C—C9C	120.9 (9)	C20B—C21B—C22B	120.7 (8)
C13C—C8C—S1C	119.8 (8)	C20B—C21B—H30	119.7
C9C—C8C—S1C	119.4 (7)	C22B—C21B—H30	119.7
C13B—C8B—C9B	119.5 (9)	C23C—C22C—C21C	122.4 (10)
C13B—C8B—S1B	120.3 (7)	C23C—C22C—H48	118.8
C9B—C8B—S1B	120.2 (8)	C21C—C22C—H48	118.8
C9A—C8A—C13A	120.3 (9)	C23B—C22B—C21B	120.0 (9)
C9A—C8A—S1A	119.9 (7)	C23B—C22B—H31	120.0
C13A—C8A—S1A	119.7 (7)	C21B—C22B—H31	120.0
C8A—C9A—C10A	120.5 (11)	C23A—C22A—C21A	120.5 (10)
C8A—C9A—H3	119.8	C23A—C22A—H14	119.7
C10A—C9A—H3	119.8	C21A—C22A—H14	119.7
C10C—C9C—C8C	118.6 (10)	C22C—C23C—C24C	119.8 (9)
C10C—C9C—H37	120.7	C22C—C23C—H49	120.1
C8C—C9C—H37	120.7	C24C—C23C—H49	120.1
C10B—C9B—C8B	120.5 (11)	C22B—C23B—C24B	120.0 (8)
C10B—C9B—H20	119.7	C22B—C23B—H32	120.0
C8B—C9B—H20	119.7	C24B—C23B—H32	120.0
C11B—C10B—C9B	117.4 (12)	C24A—C23A—C22A	118.6 (10)
C11B—C10B—H21	121.3	C24A—C23A—H15	120.7
C9B—C10B—H21	121.3	C22A—C23A—H15	120.7
C11A—C10A—C9A	121.8 (14)	C25C—C24C—C23C	119.5 (10)
C11A—C10A—H4	119.1	C25C—C24C—H50	120.2
C9A—C10A—H4	119.1	C23C—C24C—H50	120.2
C11C—C10C—C9C	122.6 (12)	C23A—C24A—C25A	121.8 (10)
C11C—C10C—H38	118.7	C23A—C24A—H16	119.1
C9C—C10C—H38	118.7	C25A—C24A—H16	119.1
C12B—C11B—C10B	123.5 (12)	C25B—C24B—C23B	119.9 (8)
C12B—C11B—H22	118.3	C25B—C24B—H33	120.1
C10B—C11B—H22	118.3	C23B—C24B—H33	120.1
C10C—C11C—C12C	119.1 (12)	C24A—C25A—C20A	119.8 (9)
C10C—C11C—H39	120.5	C24A—C25A—H17	120.1
C12C—C11C—H39	120.5	C20A—C25A—H17	120.1
C10A—C11A—C12A	119.6 (14)	C24B—C25B—C20B	120.9 (8)
C10A—C11A—H5	120.2	C24B—C25B—H34	119.6
C12A—C11A—H5	120.2	C20B—C25B—H34	119.6
C11B—C12B—C13B	120.5 (11)	C24C—C25C—C20C	119.5 (9)
C11B—C12B—H23	119.8	C24C—C25C—H51	120.2
C13B—C12B—H23	119.8	C20C—C25C—H51	120.2

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4,6-Diphenyl-1-(phenyl­sulfon­yl)-1H-furo[3,4-b]pyrrole

Supporting information

Key indicators

checkCIF/PLATON results

4,6-Diphenyl-1-(phenylsulfonyl)-1H-furo[3,4-b]pyrrole