Crystal structure and Hirshfeld surface analysis of dimethyl 4-hy­droxy-5,4′-dimethyl-2′-(toluene-4-sulfonyl­amino)­biphenyl-2,3-di­carboxyl­ate

In the crystal, mol­ecules are connected by C—H...O and N—H...O hydrogen bonds, forming mol­ecular layers parallel to the (100) plane. These layers are connected to each other by C—H...π inter­actions.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.033
• wR factor = 0.088
• Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT142_ALERT_4_G s.u. on b - Axis Small or Missing ..............    0.00012 Ang.
PLAT143_ALERT_4_G s.u. on c - Axis Small or Missing ..............    0.00007 Ang.
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          2 Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         14 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         15 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Dimethyl 4-hydroxy-5,4'-dimethyl-2'-{[(4-methylphenyl)sulfonyl]amino}biphenyl-\ 2,3-dicarboxylate

Crystal data

C25H25NO7S	F(000) = 1016
Mr = 483.52	Dx = 1.354 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 12.52978 (9) Å	Cell parameters from 26913 reflections
b = 18.87277 (12) Å	θ = 4.4–77.8°
c = 10.63916 (7) Å	µ = 1.61 mm^−1
β = 109.4092 (8)°	T = 100 K
V = 2372.88 (3) Å^3	Prism, colourless
Z = 4	0.22 × 0.20 × 0.15 mm

Data collection

XtaLAB Synergy, Dualflex, HyPix diffractometer	4842 reflections with I > 2σ(I)
Radiation source: micro-focus sealed X-ray tube	Rint = 0.044
φ and ω scans	θmax = 77.8°, θmin = 3.7°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021)	h = −15→15
Tmin = 0.654, Tmax = 1.000	k = −22→23
37027 measured reflections	l = −13→13
5051 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.088	w = 1/[σ^2(Fo^2) + (0.0419P)^2 + 1.207P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
5051 reflections	Δρmax = 0.33 e Å^−3
321 parameters	Δρmin = −0.44 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: difference Fourier map	Extinction coefficient: 0.00097 (9)

Special details

Experimental. CrysAlisPro 1.171.41.117a (Rigaku OD, 2021) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.47540 (2)	0.47876 (2)	0.28445 (3)	0.01572 (9)
O1	0.87334 (8)	0.69147 (5)	0.70753 (10)	0.0219 (2)
H1O	0.8780 (19)	0.6776 (12)	0.791 (2)	0.054 (6)*
O2	0.87491 (9)	0.61396 (5)	0.90556 (9)	0.0289 (2)
O3	0.83061 (9)	0.49945 (5)	0.87207 (9)	0.0254 (2)
O4	0.75736 (8)	0.38919 (5)	0.63886 (9)	0.0229 (2)
O5	0.94306 (8)	0.41300 (5)	0.73522 (9)	0.0245 (2)
O6	0.40571 (7)	0.48386 (5)	0.36703 (9)	0.01983 (19)
O7	0.43510 (7)	0.44113 (5)	0.16051 (8)	0.01987 (19)
N1	0.59121 (9)	0.43960 (5)	0.37778 (10)	0.0167 (2)
H1N	0.6110 (15)	0.4544 (9)	0.4562 (18)	0.028 (4)*
C1	0.85341 (10)	0.63093 (6)	0.63507 (12)	0.0172 (2)
C2	0.84786 (10)	0.56433 (6)	0.69114 (12)	0.0165 (2)
C3	0.82958 (10)	0.50356 (6)	0.60943 (12)	0.0155 (2)
C4	0.81082 (10)	0.51001 (6)	0.47363 (12)	0.0159 (2)
C5	0.81682 (10)	0.57750 (7)	0.42116 (12)	0.0181 (2)
H5	0.8049	0.5819	0.3285	0.022*
C6	0.83940 (10)	0.63786 (6)	0.49899 (12)	0.0188 (2)
C7	0.85359 (10)	0.56214 (7)	0.83223 (12)	0.0193 (2)
C8	0.82815 (14)	0.49568 (9)	1.00727 (14)	0.0332 (3)
H8A	0.7721	0.5293	1.0178	0.050*
H8B	0.9030	0.5076	1.0700	0.050*
H8C	0.8077	0.4476	1.0254	0.050*
C9	0.83582 (10)	0.42959 (6)	0.66379 (11)	0.0175 (2)
C10	0.95930 (14)	0.34207 (8)	0.78924 (16)	0.0360 (4)
H10A	0.9373	0.3076	0.7161	0.054*
H10B	0.9125	0.3352	0.8460	0.054*
H10C	1.0391	0.3352	0.8423	0.054*
C11	0.78777 (10)	0.44813 (6)	0.38084 (11)	0.0161 (2)
C12	0.67941 (10)	0.41792 (6)	0.32872 (11)	0.0160 (2)
C13	0.65792 (10)	0.36524 (6)	0.23203 (12)	0.0183 (2)
H13	0.5840	0.3457	0.1970	0.022*
C14	0.74280 (11)	0.34054 (7)	0.18550 (12)	0.0193 (2)
C15	0.85138 (11)	0.36831 (7)	0.24215 (13)	0.0210 (3)
H15	0.9113	0.3506	0.2151	0.025*
C16	0.87306 (10)	0.42142 (7)	0.33738 (12)	0.0201 (3)
H16	0.9475	0.4399	0.3737	0.024*
C17	0.51190 (10)	0.56517 (6)	0.25010 (12)	0.0178 (2)
C18	0.50126 (11)	0.62124 (7)	0.32991 (13)	0.0222 (3)
H18	0.4745	0.6133	0.4024	0.027*
C19	0.53028 (12)	0.68894 (7)	0.30225 (13)	0.0224 (3)
H19	0.5228	0.7273	0.3565	0.027*
C20	0.57021 (10)	0.70204 (7)	0.19664 (12)	0.0198 (2)
C21	0.58170 (11)	0.64480 (7)	0.11927 (12)	0.0211 (3)
H21	0.6100	0.6526	0.0480	0.025*
C22	0.55246 (11)	0.57649 (7)	0.14447 (12)	0.0197 (2)
H22	0.5600	0.5380	0.0904	0.024*
C23	0.59565 (12)	0.77675 (7)	0.16557 (13)	0.0250 (3)
H23A	0.5250	0.8006	0.1147	0.037*
H23B	0.6466	0.7758	0.1128	0.037*
H23C	0.6319	0.8025	0.2489	0.037*
C24	0.71670 (12)	0.28600 (7)	0.07589 (14)	0.0264 (3)
H24A	0.6916	0.2420	0.1064	0.040*
H24B	0.7849	0.2767	0.0528	0.040*
H24C	0.6566	0.3038	−0.0027	0.040*
C25	0.85016 (13)	0.70949 (7)	0.44329 (14)	0.0273 (3)
H25A	0.9281	0.7264	0.4826	0.041*
H25B	0.7985	0.7427	0.4645	0.041*
H25C	0.8308	0.7061	0.3463	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01611 (15)	0.01641 (15)	0.01492 (15)	−0.00118 (10)	0.00555 (11)	−0.00276 (10)
O1	0.0258 (5)	0.0150 (4)	0.0243 (5)	−0.0007 (3)	0.0075 (4)	−0.0048 (3)
O2	0.0414 (6)	0.0258 (5)	0.0193 (4)	−0.0024 (4)	0.0098 (4)	−0.0067 (4)
O3	0.0356 (5)	0.0253 (5)	0.0150 (4)	−0.0039 (4)	0.0081 (4)	0.0016 (4)
O4	0.0268 (5)	0.0180 (4)	0.0221 (4)	−0.0035 (4)	0.0057 (4)	0.0021 (3)
O5	0.0248 (5)	0.0180 (4)	0.0243 (5)	0.0032 (4)	−0.0005 (4)	0.0032 (4)
O6	0.0185 (4)	0.0218 (4)	0.0211 (4)	−0.0015 (3)	0.0091 (4)	−0.0028 (3)
O7	0.0205 (4)	0.0210 (4)	0.0166 (4)	−0.0011 (3)	0.0041 (3)	−0.0050 (3)
N1	0.0180 (5)	0.0184 (5)	0.0138 (5)	−0.0011 (4)	0.0056 (4)	−0.0025 (4)
C1	0.0146 (5)	0.0162 (6)	0.0198 (6)	0.0002 (4)	0.0043 (4)	−0.0032 (4)
C2	0.0148 (5)	0.0173 (6)	0.0166 (5)	0.0004 (4)	0.0043 (4)	−0.0011 (4)
C3	0.0139 (5)	0.0153 (6)	0.0166 (5)	0.0002 (4)	0.0042 (4)	0.0002 (4)
C4	0.0138 (5)	0.0169 (6)	0.0163 (5)	−0.0005 (4)	0.0041 (4)	−0.0002 (4)
C5	0.0176 (5)	0.0202 (6)	0.0148 (5)	−0.0012 (4)	0.0033 (4)	0.0009 (4)
C6	0.0176 (6)	0.0165 (6)	0.0202 (6)	−0.0004 (4)	0.0036 (5)	0.0026 (5)
C7	0.0182 (6)	0.0207 (6)	0.0178 (6)	0.0016 (5)	0.0042 (5)	−0.0006 (5)
C8	0.0423 (8)	0.0419 (9)	0.0158 (6)	−0.0051 (7)	0.0099 (6)	0.0034 (6)
C9	0.0223 (6)	0.0167 (6)	0.0125 (5)	0.0014 (5)	0.0044 (4)	−0.0001 (4)
C10	0.0417 (9)	0.0202 (7)	0.0336 (8)	0.0070 (6)	−0.0043 (6)	0.0068 (6)
C11	0.0179 (6)	0.0163 (6)	0.0130 (5)	−0.0001 (4)	0.0036 (4)	0.0005 (4)
C12	0.0178 (5)	0.0152 (5)	0.0153 (5)	0.0009 (4)	0.0059 (4)	0.0014 (4)
C13	0.0186 (6)	0.0170 (6)	0.0183 (6)	−0.0010 (4)	0.0045 (5)	−0.0016 (4)
C14	0.0223 (6)	0.0170 (6)	0.0169 (5)	0.0028 (5)	0.0043 (5)	−0.0011 (4)
C15	0.0199 (6)	0.0229 (6)	0.0206 (6)	0.0042 (5)	0.0074 (5)	−0.0020 (5)
C16	0.0175 (6)	0.0226 (6)	0.0193 (6)	−0.0008 (5)	0.0048 (5)	−0.0013 (5)
C17	0.0181 (6)	0.0178 (6)	0.0163 (5)	0.0003 (4)	0.0042 (4)	−0.0008 (4)
C18	0.0284 (7)	0.0220 (6)	0.0190 (6)	−0.0007 (5)	0.0114 (5)	−0.0021 (5)
C19	0.0293 (7)	0.0184 (6)	0.0203 (6)	0.0013 (5)	0.0094 (5)	−0.0023 (5)
C20	0.0199 (6)	0.0192 (6)	0.0177 (6)	0.0006 (5)	0.0029 (5)	0.0018 (5)
C21	0.0245 (6)	0.0244 (6)	0.0150 (5)	0.0001 (5)	0.0073 (5)	0.0006 (5)
C22	0.0230 (6)	0.0206 (6)	0.0161 (5)	0.0007 (5)	0.0072 (5)	−0.0027 (5)
C23	0.0301 (7)	0.0206 (6)	0.0233 (6)	−0.0013 (5)	0.0076 (5)	0.0032 (5)
C24	0.0261 (7)	0.0250 (7)	0.0262 (7)	0.0035 (5)	0.0062 (5)	−0.0093 (5)
C25	0.0354 (7)	0.0187 (6)	0.0243 (7)	−0.0053 (5)	0.0054 (6)	0.0031 (5)

Geometric parameters (Å, º)

S1—O6	1.4330 (9)	C11—C16	1.3922 (17)
S1—O7	1.4338 (9)	C11—C12	1.4056 (17)
S1—N1	1.6372 (11)	C12—C13	1.3911 (17)
S1—C17	1.7643 (13)	C13—C14	1.3940 (17)
O1—C1	1.3543 (14)	C13—H13	0.9500
O1—H1O	0.91 (2)	C14—C15	1.3942 (18)
O2—C7	1.2239 (16)	C14—C24	1.5076 (17)
O3—C7	1.3203 (16)	C15—C16	1.3864 (18)
O3—C8	1.4507 (16)	C15—H15	0.9500
O4—C9	1.2020 (16)	C16—H16	0.9500
O5—C9	1.3425 (15)	C17—C18	1.3907 (17)
O5—C10	1.4444 (16)	C17—C22	1.3952 (17)
N1—C12	1.4298 (15)	C18—C19	1.3864 (18)
N1—H1N	0.836 (18)	C18—H18	0.9500
C1—C2	1.4029 (17)	C19—C20	1.3955 (18)
C1—C6	1.4054 (17)	C19—H19	0.9500
C2—C3	1.4112 (16)	C20—C21	1.3943 (18)
C2—C7	1.4794 (17)	C20—C23	1.5064 (17)
C3—C4	1.3899 (16)	C21—C22	1.3904 (18)
C3—C9	1.5031 (16)	C21—H21	0.9500
C4—C5	1.4028 (17)	C22—H22	0.9500
C4—C11	1.4941 (16)	C23—H23A	0.9800
C5—C6	1.3811 (17)	C23—H23B	0.9800
C5—H5	0.9500	C23—H23C	0.9800
C6—C25	1.4999 (17)	C24—H24A	0.9800
C8—H8A	0.9800	C24—H24B	0.9800
C8—H8B	0.9800	C24—H24C	0.9800
C8—H8C	0.9800	C25—H25A	0.9800
C10—H10A	0.9800	C25—H25B	0.9800
C10—H10B	0.9800	C25—H25C	0.9800
C10—H10C	0.9800
O6—S1—O7	119.80 (5)	C13—C12—C11	120.39 (11)
O6—S1—N1	104.85 (5)	C13—C12—N1	119.43 (11)
O7—S1—N1	107.72 (5)	C11—C12—N1	120.16 (10)
O6—S1—C17	108.52 (6)	C12—C13—C14	121.23 (11)
O7—S1—C17	107.68 (6)	C12—C13—H13	119.4
N1—S1—C17	107.72 (6)	C14—C13—H13	119.4
C1—O1—H1O	104.7 (14)	C13—C14—C15	118.09 (11)
C7—O3—C8	116.17 (11)	C13—C14—C24	120.53 (11)
C9—O5—C10	115.05 (11)	C15—C14—C24	121.37 (11)
C12—N1—S1	123.00 (8)	C16—C15—C14	120.91 (11)
C12—N1—H1N	116.8 (12)	C16—C15—H15	119.5
S1—N1—H1N	111.3 (12)	C14—C15—H15	119.5
O1—C1—C2	122.66 (11)	C15—C16—C11	121.26 (11)
O1—C1—C6	116.37 (11)	C15—C16—H16	119.4
C2—C1—C6	120.97 (11)	C11—C16—H16	119.4
C1—C2—C3	119.15 (11)	C18—C17—C22	120.65 (12)
C1—C2—C7	117.65 (11)	C18—C17—S1	119.52 (10)
C3—C2—C7	123.06 (11)	C22—C17—S1	119.82 (9)
C4—C3—C2	120.39 (11)	C19—C18—C17	119.11 (12)
C4—C3—C9	116.77 (10)	C19—C18—H18	120.4
C2—C3—C9	122.74 (10)	C17—C18—H18	120.4
C3—C4—C5	118.70 (11)	C18—C19—C20	121.58 (12)
C3—C4—C11	123.18 (11)	C18—C19—H19	119.2
C5—C4—C11	118.10 (10)	C20—C19—H19	119.2
C6—C5—C4	122.53 (11)	C21—C20—C19	118.23 (12)
C6—C5—H5	118.7	C21—C20—C23	121.65 (12)
C4—C5—H5	118.7	C19—C20—C23	120.08 (12)
C5—C6—C1	118.13 (11)	C22—C21—C20	121.27 (11)
C5—C6—C25	122.27 (11)	C22—C21—H21	119.4
C1—C6—C25	119.60 (11)	C20—C21—H21	119.4
O2—C7—O3	122.41 (12)	C21—C22—C17	119.15 (11)
O2—C7—C2	123.45 (12)	C21—C22—H22	120.4
O3—C7—C2	114.12 (11)	C17—C22—H22	120.4
O3—C8—H8A	109.5	C20—C23—H23A	109.5
O3—C8—H8B	109.5	C20—C23—H23B	109.5
H8A—C8—H8B	109.5	H23A—C23—H23B	109.5
O3—C8—H8C	109.5	C20—C23—H23C	109.5
H8A—C8—H8C	109.5	H23A—C23—H23C	109.5
H8B—C8—H8C	109.5	H23B—C23—H23C	109.5
O4—C9—O5	124.64 (11)	C14—C24—H24A	109.5
O4—C9—C3	124.75 (11)	C14—C24—H24B	109.5
O5—C9—C3	110.41 (10)	H24A—C24—H24B	109.5
O5—C10—H10A	109.5	C14—C24—H24C	109.5
O5—C10—H10B	109.5	H24A—C24—H24C	109.5
H10A—C10—H10B	109.5	H24B—C24—H24C	109.5
O5—C10—H10C	109.5	C6—C25—H25A	109.5
H10A—C10—H10C	109.5	C6—C25—H25B	109.5
H10B—C10—H10C	109.5	H25A—C25—H25B	109.5
C16—C11—C12	118.01 (11)	C6—C25—H25C	109.5
C16—C11—C4	120.09 (11)	H25A—C25—H25C	109.5
C12—C11—C4	121.80 (11)	H25B—C25—H25C	109.5
O6—S1—N1—C12	173.68 (9)	C3—C4—C11—C16	−102.44 (14)
O7—S1—N1—C12	45.03 (11)	C5—C4—C11—C16	75.74 (15)
C17—S1—N1—C12	−70.86 (11)	C3—C4—C11—C12	81.40 (15)
O1—C1—C2—C3	−178.41 (11)	C5—C4—C11—C12	−100.42 (14)
C6—C1—C2—C3	0.95 (17)	C16—C11—C12—C13	−2.95 (17)
O1—C1—C2—C7	5.80 (17)	C4—C11—C12—C13	173.28 (11)
C6—C1—C2—C7	−174.84 (11)	C16—C11—C12—N1	175.10 (11)
C1—C2—C3—C4	−3.68 (17)	C4—C11—C12—N1	−8.66 (17)
C7—C2—C3—C4	171.87 (11)	S1—N1—C12—C13	−65.05 (14)
C1—C2—C3—C9	172.71 (11)	S1—N1—C12—C11	116.88 (11)
C7—C2—C3—C9	−11.74 (18)	C11—C12—C13—C14	0.72 (18)
C2—C3—C4—C5	3.56 (17)	N1—C12—C13—C14	−177.35 (11)
C9—C3—C4—C5	−173.04 (10)	C12—C13—C14—C15	2.31 (19)
C2—C3—C4—C11	−178.27 (11)	C12—C13—C14—C24	−176.98 (12)
C9—C3—C4—C11	5.13 (17)	C13—C14—C15—C16	−3.09 (19)
C3—C4—C5—C6	−0.73 (18)	C24—C14—C15—C16	176.20 (12)
C11—C4—C5—C6	−178.99 (11)	C14—C15—C16—C11	0.8 (2)
C4—C5—C6—C1	−1.93 (18)	C12—C11—C16—C15	2.20 (18)
C4—C5—C6—C25	177.57 (12)	C4—C11—C16—C15	−174.11 (11)
O1—C1—C6—C5	−178.81 (11)	O6—S1—C17—C18	18.25 (12)
C2—C1—C6—C5	1.80 (18)	O7—S1—C17—C18	149.32 (10)
O1—C1—C6—C25	1.68 (17)	N1—S1—C17—C18	−94.76 (11)
C2—C1—C6—C25	−177.72 (12)	O6—S1—C17—C22	−162.58 (10)
C8—O3—C7—O2	2.03 (19)	O7—S1—C17—C22	−31.51 (12)
C8—O3—C7—C2	−176.26 (11)	N1—S1—C17—C22	84.42 (11)
C1—C2—C7—O2	−8.10 (18)	C22—C17—C18—C19	0.8 (2)
C3—C2—C7—O2	176.29 (12)	S1—C17—C18—C19	179.92 (10)
C1—C2—C7—O3	170.16 (11)	C17—C18—C19—C20	−0.2 (2)
C3—C2—C7—O3	−5.45 (17)	C18—C19—C20—C21	−0.7 (2)
C10—O5—C9—O4	−3.35 (18)	C18—C19—C20—C23	177.09 (12)
C10—O5—C9—C3	−178.35 (11)	C19—C20—C21—C22	1.12 (19)
C4—C3—C9—O4	−68.07 (16)	C23—C20—C21—C22	−176.63 (12)
C2—C3—C9—O4	115.42 (14)	C20—C21—C22—C17	−0.61 (19)
C4—C3—C9—O5	106.91 (12)	C18—C17—C22—C21	−0.35 (19)
C2—C3—C9—O5	−69.60 (14)	S1—C17—C22—C21	−179.51 (9)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4	0.836 (18)	2.507 (18)	3.0185 (14)	120.5 (15)
N1—H1N···O6^i	0.836 (18)	2.280 (18)	3.0643 (14)	156.4 (18)
O1—H1O···O2	0.91 (2)	1.72 (2)	2.5596 (14)	152 (2)
C13—H13···O7	0.95	2.53	3.0022 (16)	111
C18—H18···O6	0.95	2.58	2.9370 (16)	103
C24—H24A···O4^ii	0.98	2.60	3.3784 (16)	137
C25—H25C···O1^iii	0.98	2.59	3.2177 (17)	122
C16—H16···Cg1^iv	0.95	2.61	3.4780 (14)	153

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+1/2, z−1/2; (iii) x, −y+3/2, z−1/2; (iv) −x+2, −y+1, −z+1.