Polymorphism in the structure of N-(5-methyl­thia­zol-2-yl)-4-oxo-4H-chromene-3-carboxamide

The new chromone–thia­zole hybrid presented here is a candidate as a selective ligand for adenosine receptors. Its structure shows packing polymorphism: the two polymorphs (one with space group P2₁/n and one with P2₁/c) show slightly different conformations and the major change induced by crystallization regards the intra­molecular contacts defining the supra­molecular structure.

Key indicators

Structure: 1_P2~1~_n

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.097
• wR factor = 0.223
• Data-to-parameter ratio = 16.2

Structure: 1_P2~1~_c

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.060
• wR factor = 0.153
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Datablock: 1_P2~1~_n



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.14 Report
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00692 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......     23.560 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      5.245 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.310 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          7 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          3 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          8 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          6 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Note

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check




Datablock: 1_P2~1~_c



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00421 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H28    ..  N133    ..       2.69 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H23B   ..  S131    ..       3.00 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.647 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         49 Report

Alert level G
PLAT432_ALERT_2_G Short Inter X...Y Contact  O14    ..  C22     ..       3.00 Ang.
PLAT432_ALERT_2_G Short Inter X...Y Contact  O24    ..  C12     ..       2.96 Ang.
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         67 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          6 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 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
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 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

For both structures, data collection: CrystalClear-SM Expert (Rigaku, 2012); cell refinement: CrystalClear-SM Expert (Rigaku, 2012); data reduction: CrystalClear-SM Expert (Rigaku, 2012). Program(s) used to solve structure: SHELXT (Sheldrick, 2015a) for 1_P2~1~_n; SHELXS (Sheldrick, 2008) for 1_P2~1~_c. Program(s) used to refine structure: OSCAIL (McArdle et al., 2004), ShelXle (Hübschle et al., 2011) and SHELXL2014 (Sheldrick, 2015b) for 1_P2~1~_n; OSCAIL (McArdle et al., 2004), ShelXle (Hübschle et al., 2011) SHELXL (Sheldrick, 2008) for 1_P2~1~_c. For both structures, molecular graphics: Mercury (Macrae et al., 2006). Software used to prepare material for publication: OSCAIL (McArdle et al., 2004), SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2009) for 1_P2~1~_n; OSCAIL (McArdle et al., 2004), SHELXL (Sheldrick, 2008) for 1_P2~1~_c.

N-(5-Methylthiazol-2-yl)-4-oxo-4H-chromene-3-carboxamide (1_P2~1~_n)

Crystal data

C14H10N2O3S	F(000) = 592
Mr = 286.30	Dx = 1.484 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 4.8722 (4) Å	Cell parameters from 3369 reflections
b = 12.0436 (10) Å	θ = 2.5–27.5°
c = 21.9803 (16) Å	µ = 0.26 mm^−1
β = 96.353 (8)°	T = 100 K
V = 1281.86 (18) Å^3	Needle, yellow
Z = 4	0.28 × 0.03 × 0.02 mm

Data collection

Rigaku Saturn724+ diffractometer	2944 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1980 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.084
profile data from ω–scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012)	h = −6→6
Tmin = 0.814, Tmax = 1.000	k = −15→15
13600 measured reflections	l = −28→28

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.097	H-atom parameters constrained
wR(F^2) = 0.223	w = 1/[σ^2(Fo^2) + (0.0714P)^2 + 3.9146P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max = 0.001
2944 reflections	Δρmax = 1.15 e Å^−3
182 parameters	Δρmin = −0.37 e Å^−3

Special details

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
S31	0.9829 (3)	0.89007 (11)	0.43688 (5)	0.0282 (3)
O1	−0.0148 (6)	1.0107 (2)	0.21301 (14)	0.0251 (7)
O3	0.6328 (7)	0.9809 (3)	0.34453 (14)	0.0297 (8)
O4	0.1136 (6)	0.7088 (3)	0.29518 (14)	0.0252 (7)
N3	0.5557 (8)	0.7992 (3)	0.36084 (16)	0.0245 (9)
H3	0.4531	0.7413	0.3489	0.029*
N33	0.8145 (9)	0.6867 (4)	0.43227 (18)	0.0323 (10)
C2	0.1942 (10)	0.9927 (4)	0.2566 (2)	0.0245 (10)
H2	0.3134	1.0535	0.2678	0.029*
C3	0.2503 (9)	0.8961 (4)	0.28596 (19)	0.0221 (10)
C4	0.0784 (9)	0.7999 (4)	0.27017 (19)	0.0211 (9)
C5	−0.3234 (10)	0.7340 (4)	0.1989 (2)	0.0253 (10)
H5	−0.2989	0.6614	0.2154	0.030*
C4A	−0.1452 (9)	0.8189 (4)	0.22095 (19)	0.0213 (10)
C6	−0.5338 (10)	0.7543 (4)	0.1535 (2)	0.0274 (11)
H6	−0.6547	0.6959	0.1389	0.033*
C7	−0.5705 (10)	0.8606 (4)	0.1288 (2)	0.0272 (11)
H7	−0.7176	0.8742	0.0976	0.033*
C8	−0.3976 (10)	0.9455 (4)	0.1489 (2)	0.0264 (10)
H8	−0.4214	1.0179	0.1320	0.032*
C8A	−0.1864 (10)	0.9224 (4)	0.1947 (2)	0.0237 (10)
C31	0.4964 (9)	0.8976 (4)	0.33283 (19)	0.0224 (10)
C32	0.7694 (10)	0.7843 (4)	0.4073 (2)	0.0283 (11)
C34	1.0346 (11)	0.6953 (5)	0.4779 (2)	0.0357 (13)
H34	1.1015	0.6326	0.5012	0.043*
C35	1.1488 (10)	0.7959 (4)	0.4877 (2)	0.0304 (11)
C351	1.3848 (10)	0.8291 (5)	0.5342 (2)	0.0368 (13)
H35A	1.4522	0.7638	0.5579	0.055*
H35B	1.3213	0.8851	0.5618	0.055*
H35C	1.5347	0.8601	0.5131	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S31	0.0245 (7)	0.0323 (7)	0.0281 (6)	0.0009 (6)	0.0043 (5)	−0.0015 (5)
O1	0.0252 (19)	0.0153 (16)	0.0340 (17)	−0.0006 (14)	−0.0002 (14)	0.0028 (13)
O3	0.030 (2)	0.0216 (18)	0.0369 (18)	−0.0055 (15)	0.0001 (14)	−0.0001 (14)
O4	0.0245 (19)	0.0164 (16)	0.0349 (17)	0.0041 (14)	0.0040 (14)	0.0008 (13)
N3	0.024 (2)	0.020 (2)	0.0289 (19)	0.0002 (17)	0.0021 (16)	−0.0030 (15)
N33	0.035 (3)	0.029 (2)	0.032 (2)	0.006 (2)	−0.0008 (18)	−0.0040 (17)
C2	0.024 (3)	0.017 (2)	0.034 (2)	−0.002 (2)	0.007 (2)	−0.0012 (18)
C3	0.023 (3)	0.017 (2)	0.028 (2)	0.0020 (19)	0.0098 (18)	0.0005 (17)
C4	0.022 (2)	0.015 (2)	0.028 (2)	0.0033 (19)	0.0093 (18)	−0.0021 (17)
C5	0.026 (3)	0.020 (2)	0.031 (2)	0.001 (2)	0.009 (2)	0.0017 (18)
C4A	0.023 (3)	0.015 (2)	0.028 (2)	−0.0045 (19)	0.0098 (19)	−0.0027 (17)
C6	0.025 (3)	0.025 (3)	0.033 (2)	−0.003 (2)	0.005 (2)	−0.0058 (19)
C7	0.027 (3)	0.027 (3)	0.028 (2)	0.001 (2)	0.003 (2)	0.0012 (18)
C8	0.026 (3)	0.021 (2)	0.033 (2)	0.005 (2)	0.004 (2)	0.0036 (18)
C8A	0.024 (3)	0.017 (2)	0.032 (2)	−0.0016 (19)	0.010 (2)	−0.0032 (18)
C31	0.023 (3)	0.017 (2)	0.028 (2)	0.000 (2)	0.0077 (19)	−0.0023 (17)
C32	0.033 (3)	0.026 (3)	0.027 (2)	0.004 (2)	0.008 (2)	−0.0043 (18)
C34	0.037 (3)	0.042 (3)	0.026 (2)	0.020 (3)	0.000 (2)	−0.002 (2)
C35	0.025 (3)	0.039 (3)	0.028 (2)	0.007 (2)	0.006 (2)	−0.004 (2)
C351	0.027 (3)	0.048 (3)	0.034 (3)	0.004 (3)	0.001 (2)	−0.005 (2)

Geometric parameters (Å, º)

S31—C32	1.726 (5)	C5—C6	1.371 (7)
S31—C35	1.728 (5)	C5—C4A	1.393 (6)
O1—C2	1.336 (6)	C5—H5	0.9500
O1—C8A	1.384 (5)	C4A—C8A	1.379 (6)
O3—C31	1.215 (5)	C6—C7	1.394 (7)
O4—C4	1.231 (5)	C6—H6	0.9500
N3—C31	1.353 (6)	C7—C8	1.367 (7)
N3—C32	1.387 (6)	C7—H7	0.9500
N3—H3	0.8800	C8—C8A	1.387 (7)
N33—C32	1.306 (6)	C8—H8	0.9500
N33—C34	1.388 (6)	C34—C35	1.341 (7)
C2—C3	1.344 (6)	C34—H34	0.9500
C2—H2	0.9500	C35—C351	1.506 (7)
C3—C4	1.449 (6)	C351—H35A	0.9800
C3—C31	1.492 (7)	C351—H35B	0.9800
C4—C4A	1.466 (6)	C351—H35C	0.9800
C32—S31—C35	88.8 (2)	C6—C7—H7	119.5
C2—O1—C8A	118.1 (4)	C7—C8—C8A	117.8 (4)
C31—N3—C32	123.6 (4)	C7—C8—H8	121.1
C31—N3—H3	118.2	C8A—C8—H8	121.1
C32—N3—H3	118.2	C4A—C8A—O1	121.2 (4)
C32—N33—C34	108.4 (4)	C4A—C8A—C8	123.2 (4)
O1—C2—C3	125.7 (4)	O1—C8A—C8	115.6 (4)
O1—C2—H2	117.2	O3—C31—N3	122.9 (4)
C3—C2—H2	117.2	O3—C31—C3	122.4 (4)
C2—C3—C4	119.7 (4)	N3—C31—C3	114.8 (4)
C2—C3—C31	115.2 (4)	N33—C32—N3	120.2 (4)
C4—C3—C31	125.0 (4)	N33—C32—S31	116.1 (4)
O4—C4—C3	123.9 (4)	N3—C32—S31	123.7 (4)
O4—C4—C4A	121.6 (4)	C35—C34—N33	117.2 (5)
C3—C4—C4A	114.5 (4)	C35—C34—H34	121.4
C6—C5—C4A	120.7 (4)	N33—C34—H34	121.4
C6—C5—H5	119.7	C34—C35—C351	128.4 (5)
C4A—C5—H5	119.7	C34—C35—S31	109.4 (4)
C8A—C4A—C5	117.5 (4)	C351—C35—S31	122.1 (4)
C8A—C4A—C4	120.7 (4)	C35—C351—H35A	109.5
C5—C4A—C4	121.8 (4)	C35—C351—H35B	109.5
C5—C6—C7	120.0 (5)	H35A—C351—H35B	109.5
C5—C6—H6	120.0	C35—C351—H35C	109.5
C7—C6—H6	120.0	H35A—C351—H35C	109.5
C8—C7—C6	120.9 (5)	H35B—C351—H35C	109.5
C8—C7—H7	119.5
C8A—O1—C2—C3	−1.8 (6)	C2—O1—C8A—C8	−179.3 (4)
O1—C2—C3—C4	0.9 (7)	C7—C8—C8A—C4A	−0.5 (7)
O1—C2—C3—C31	179.9 (4)	C7—C8—C8A—O1	179.3 (4)
C2—C3—C4—O4	−179.2 (4)	C32—N3—C31—O3	2.9 (7)
C31—C3—C4—O4	1.9 (7)	C32—N3—C31—C3	−177.4 (4)
C2—C3—C4—C4A	1.1 (6)	C2—C3—C31—O3	1.5 (6)
C31—C3—C4—C4A	−177.8 (4)	C4—C3—C31—O3	−179.6 (4)
C6—C5—C4A—C8A	−1.1 (6)	C2—C3—C31—N3	−178.2 (4)
C6—C5—C4A—C4	178.9 (4)	C4—C3—C31—N3	0.7 (6)
O4—C4—C4A—C8A	178.1 (4)	C34—N33—C32—N3	−178.9 (4)
C3—C4—C4A—C8A	−2.2 (6)	C34—N33—C32—S31	−0.4 (5)
O4—C4—C4A—C5	−1.9 (6)	C31—N3—C32—N33	180.0 (4)
C3—C4—C4A—C5	177.8 (4)	C31—N3—C32—S31	1.6 (6)
C4A—C5—C6—C7	0.2 (7)	C35—S31—C32—N33	−0.2 (4)
C5—C6—C7—C8	0.5 (7)	C35—S31—C32—N3	178.3 (4)
C6—C7—C8—C8A	−0.4 (7)	C32—N33—C34—C35	0.9 (6)
C5—C4A—C8A—O1	−178.5 (4)	N33—C34—C35—C351	179.2 (4)
C4—C4A—C8A—O1	1.5 (6)	N33—C34—C35—S31	−1.1 (6)
C5—C4A—C8A—C8	1.2 (7)	C32—S31—C35—C34	0.7 (4)
C4—C4A—C8A—C8	−178.8 (4)	C32—S31—C35—C351	−179.5 (4)
C2—O1—C8A—C4A	0.5 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O4	0.88	1.96	2.687 (5)	139
C2—H2···O4^i	0.95	2.38	3.030 (5)	126
C8—H8···N33^i	0.95	2.56	3.455 (6)	157

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

(1_P2~1~_c)

Crystal data

C14H10N2O3S	F(000) = 1184
Mr = 286.30	Dx = 1.503 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
a = 7.4646 (5) Å	Cell parameters from 12722 reflections
b = 30.626 (2) Å	θ = 2.3–27.5°
c = 11.0869 (8) Å	µ = 0.26 mm^−1
β = 93.232 (2)°	T = 100 K
V = 2530.6 (3) Å^3	Plate, colourless
Z = 8	0.06 × 0.06 × 0.01 mm

Data collection

Rigaku Saturn724+ diffractometer	5716 independent reflections
Radiation source: Sealed Tube	3733 reflections with I > 2σ(I)
Graphite Monochromator monochromator	Rint = 0.090
Detector resolution: 28.5714 pixels mm^-1	θmax = 27.5°, θmin = 2.3°
profile data from ω–scans	h = −8→9
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012)	k = −37→39
Tmin = 0.538, Tmax = 1.000	l = −14→14
15726 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.060	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.153	w = 1/[σ^2(Fo^2) + (0.0558P)^2 + 1.3609P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
5716 reflections	Δρmax = 0.46 e Å^−3
371 parameters	Δρmin = −0.37 e Å^−3

Special details

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
S131	0.61048 (10)	0.46741 (2)	0.38319 (7)	0.01951 (19)
S231	0.12461 (10)	0.35373 (2)	0.43837 (8)	0.0231 (2)
O11	0.7012 (3)	0.25605 (6)	0.53314 (18)	0.0193 (5)
O14	0.4476 (3)	0.30431 (6)	0.22432 (19)	0.0210 (5)
O21	0.1940 (3)	0.13877 (6)	0.52234 (19)	0.0211 (5)
O24	−0.0676 (3)	0.19810 (6)	0.2322 (2)	0.0221 (5)
O131	0.6665 (3)	0.38847 (6)	0.49383 (19)	0.0213 (5)
O231	0.1912 (3)	0.27146 (7)	0.5128 (2)	0.0254 (5)
N13	0.5367 (3)	0.38401 (8)	0.3050 (2)	0.0187 (6)
N23	0.0312 (3)	0.27500 (8)	0.3342 (3)	0.0198 (6)
N133	0.4688 (4)	0.44311 (8)	0.1763 (2)	0.0259 (6)
N233	−0.0482 (3)	0.33985 (8)	0.2334 (2)	0.0232 (6)
C12	0.6872 (4)	0.29895 (9)	0.5127 (3)	0.0177 (6)
H12	0.7403	0.3180	0.5722	0.021*
C13	0.6033 (4)	0.31749 (9)	0.4141 (3)	0.0166 (6)
C14	0.5230 (4)	0.29002 (9)	0.3192 (3)	0.0161 (6)
C15	0.4645 (4)	0.21215 (9)	0.2591 (3)	0.0182 (6)
H15	0.4032	0.2216	0.1863	0.022*
C14A	0.5380 (4)	0.24282 (9)	0.3424 (3)	0.0170 (6)
C16	0.4824 (4)	0.16821 (9)	0.2840 (3)	0.0191 (7)
H16	0.4344	0.1474	0.2275	0.023*
C17	0.5706 (4)	0.15392 (9)	0.3917 (3)	0.0209 (7)
H17	0.5808	0.1235	0.4078	0.025*
C18	0.6425 (4)	0.18345 (9)	0.4745 (3)	0.0190 (6)
H18	0.7022	0.1739	0.5477	0.023*
C18A	0.6252 (4)	0.22810 (9)	0.4478 (3)	0.0163 (6)
C22	0.1841 (4)	0.18235 (9)	0.5132 (3)	0.0204 (7)
H22	0.2399	0.1992	0.5768	0.024*
C23	0.1006 (4)	0.20402 (9)	0.4203 (3)	0.0171 (6)
C24	0.0102 (4)	0.18040 (10)	0.3211 (3)	0.0183 (6)
C25	−0.0718 (4)	0.10459 (9)	0.2489 (3)	0.0198 (6)
H25	−0.1343	0.1165	0.1795	0.024*
C24A	0.0162 (4)	0.13245 (9)	0.3338 (3)	0.0185 (6)
C26	−0.0676 (4)	0.06024 (10)	0.2662 (3)	0.0245 (7)
H26	−0.1286	0.0416	0.2090	0.029*
C27	0.0260 (4)	0.04218 (10)	0.3673 (3)	0.0268 (7)
H27	0.0280	0.0114	0.3784	0.032*
C28	0.1153 (4)	0.06891 (10)	0.4511 (3)	0.0240 (7)
H28	0.1811	0.0569	0.5190	0.029*
C28A	0.1069 (4)	0.11384 (9)	0.4338 (3)	0.0192 (6)
C132	0.5337 (4)	0.42830 (9)	0.2799 (3)	0.0189 (6)
C134	0.4804 (4)	0.48808 (10)	0.1767 (3)	0.0277 (8)
H134	0.4396	0.5048	0.1084	0.033*
C135	0.5518 (4)	0.50732 (9)	0.2774 (3)	0.0210 (7)
C136	0.5782 (4)	0.55514 (9)	0.3022 (3)	0.0264 (8)
H13A	0.5545	0.5717	0.2273	0.040*
H13B	0.7020	0.5603	0.3330	0.040*
H13C	0.4953	0.5646	0.3624	0.040*
C137	0.6058 (4)	0.36610 (9)	0.4097 (3)	0.0164 (6)
C232	0.0293 (4)	0.32010 (9)	0.3258 (3)	0.0190 (6)
C234	−0.0323 (4)	0.38469 (10)	0.2497 (3)	0.0255 (7)
H234	−0.0807	0.4047	0.1910	0.031*
C235	0.0546 (4)	0.39855 (10)	0.3522 (3)	0.0249 (7)
C236	0.0899 (4)	0.44428 (10)	0.3955 (3)	0.0302 (8)
H23A	0.0396	0.4650	0.3353	0.045*
H23B	0.2196	0.4490	0.4071	0.045*
H23C	0.0337	0.4488	0.4723	0.045*
C237	0.1123 (4)	0.25267 (10)	0.4275 (3)	0.0190 (6)
H13	0.499 (5)	0.3673 (12)	0.255 (3)	0.036 (11)*
H23	−0.012 (5)	0.2620 (11)	0.275 (3)	0.032 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S131	0.0231 (4)	0.0159 (3)	0.0195 (4)	0.0003 (3)	0.0008 (3)	−0.0002 (3)
S231	0.0199 (4)	0.0218 (4)	0.0277 (5)	0.0002 (3)	0.0006 (3)	−0.0048 (3)
O11	0.0246 (10)	0.0178 (10)	0.0152 (12)	−0.0001 (8)	−0.0014 (9)	0.0000 (9)
O14	0.0267 (11)	0.0184 (10)	0.0171 (12)	0.0018 (8)	−0.0062 (10)	0.0013 (9)
O21	0.0243 (11)	0.0237 (11)	0.0152 (12)	0.0017 (9)	−0.0007 (9)	0.0011 (9)
O24	0.0275 (11)	0.0217 (11)	0.0167 (12)	−0.0010 (9)	−0.0041 (10)	0.0007 (9)
O131	0.0270 (11)	0.0198 (10)	0.0167 (12)	−0.0008 (8)	−0.0016 (10)	−0.0025 (9)
O231	0.0274 (11)	0.0256 (11)	0.0224 (13)	0.0002 (9)	−0.0064 (10)	−0.0056 (10)
N13	0.0240 (14)	0.0158 (12)	0.0159 (14)	−0.0007 (10)	−0.0016 (12)	−0.0013 (11)
N23	0.0209 (13)	0.0196 (13)	0.0189 (15)	−0.0007 (10)	0.0010 (12)	−0.0030 (11)
N133	0.0344 (15)	0.0225 (13)	0.0202 (15)	0.0010 (11)	−0.0038 (13)	0.0032 (11)
N233	0.0266 (13)	0.0237 (13)	0.0197 (15)	0.0002 (11)	0.0040 (12)	0.0020 (11)
C12	0.0201 (14)	0.0166 (13)	0.0164 (16)	−0.0023 (11)	0.0006 (13)	−0.0027 (12)
C13	0.0156 (13)	0.0220 (14)	0.0125 (15)	−0.0005 (11)	0.0027 (12)	0.0000 (12)
C14	0.0154 (13)	0.0192 (14)	0.0138 (16)	0.0025 (11)	0.0015 (12)	−0.0011 (12)
C15	0.0179 (14)	0.0220 (14)	0.0149 (16)	−0.0012 (11)	0.0027 (13)	−0.0023 (12)
C14A	0.0153 (14)	0.0210 (14)	0.0151 (16)	0.0006 (11)	0.0053 (12)	−0.0003 (12)
C16	0.0210 (14)	0.0176 (14)	0.0191 (17)	−0.0033 (11)	0.0044 (13)	−0.0069 (12)
C17	0.0229 (15)	0.0171 (14)	0.0232 (18)	0.0006 (11)	0.0061 (14)	−0.0005 (13)
C18	0.0207 (14)	0.0199 (14)	0.0168 (16)	0.0004 (11)	0.0040 (13)	0.0032 (12)
C18A	0.0153 (13)	0.0241 (14)	0.0096 (15)	−0.0015 (11)	0.0011 (12)	−0.0043 (12)
C22	0.0193 (14)	0.0230 (15)	0.0189 (17)	−0.0013 (12)	0.0014 (13)	−0.0008 (13)
C23	0.0141 (13)	0.0235 (15)	0.0138 (16)	0.0002 (11)	0.0023 (12)	0.0005 (12)
C24	0.0170 (14)	0.0251 (15)	0.0128 (15)	−0.0011 (12)	0.0016 (12)	0.0020 (12)
C25	0.0190 (14)	0.0238 (14)	0.0163 (17)	−0.0013 (12)	−0.0013 (13)	−0.0008 (13)
C24A	0.0183 (14)	0.0230 (15)	0.0145 (16)	0.0020 (11)	0.0037 (13)	0.0009 (12)
C26	0.0276 (16)	0.0228 (15)	0.0231 (18)	−0.0022 (13)	0.0018 (15)	−0.0024 (14)
C27	0.0302 (17)	0.0193 (15)	0.031 (2)	0.0003 (13)	0.0061 (16)	0.0029 (14)
C28	0.0240 (15)	0.0268 (16)	0.0215 (18)	0.0046 (13)	0.0023 (14)	0.0058 (14)
C28A	0.0198 (14)	0.0219 (14)	0.0163 (16)	−0.0002 (11)	0.0043 (13)	−0.0002 (13)
C132	0.0188 (14)	0.0189 (14)	0.0190 (17)	−0.0004 (11)	0.0015 (13)	−0.0015 (13)
C134	0.0374 (18)	0.0185 (15)	0.027 (2)	0.0024 (13)	−0.0001 (16)	0.0053 (14)
C135	0.0196 (14)	0.0195 (14)	0.0242 (18)	0.0015 (12)	0.0047 (14)	0.0040 (13)
C136	0.0325 (17)	0.0174 (15)	0.030 (2)	−0.0011 (13)	0.0071 (16)	0.0035 (14)
C137	0.0128 (13)	0.0199 (14)	0.0162 (17)	−0.0013 (11)	−0.0011 (12)	−0.0006 (12)
C232	0.0187 (14)	0.0212 (14)	0.0172 (16)	−0.0003 (11)	0.0023 (13)	−0.0006 (13)
C234	0.0291 (17)	0.0229 (15)	0.0255 (19)	0.0014 (13)	0.0096 (15)	0.0009 (14)
C235	0.0200 (15)	0.0202 (15)	0.035 (2)	−0.0018 (12)	0.0093 (15)	−0.0016 (14)
C236	0.0242 (16)	0.0253 (16)	0.041 (2)	−0.0004 (13)	0.0024 (16)	−0.0040 (16)
C237	0.0158 (13)	0.0240 (15)	0.0172 (16)	0.0012 (11)	0.0010 (13)	−0.0035 (13)

Geometric parameters (Å, º)

S131—C132	1.732 (3)	C16—H16	0.9500
S131—C135	1.733 (3)	C17—C18	1.376 (4)
S231—C235	1.736 (3)	C17—H17	0.9500
S231—C232	1.739 (3)	C18—C18A	1.404 (4)
O11—C12	1.336 (3)	C18—H18	0.9500
O11—C18A	1.374 (3)	C22—C23	1.348 (4)
O14—C14	1.244 (4)	C22—H22	0.9500
O21—C22	1.340 (3)	C23—C24	1.450 (4)
O21—C28A	1.377 (4)	C23—C237	1.495 (4)
O24—C24	1.241 (4)	C24—C24A	1.476 (4)
O131—C137	1.223 (3)	C25—C26	1.372 (4)
O231—C237	1.229 (4)	C25—C24A	1.405 (4)
N13—C137	1.359 (4)	C25—H25	0.9500
N13—C132	1.385 (4)	C24A—C28A	1.389 (4)
N13—H13	0.80 (4)	C26—C27	1.401 (5)
N23—C237	1.354 (4)	C26—H26	0.9500
N23—C232	1.384 (4)	C27—C28	1.381 (4)
N23—H23	0.82 (4)	C27—H27	0.9500
N133—C132	1.302 (4)	C28—C28A	1.390 (4)
N133—C134	1.380 (4)	C28—H28	0.9500
N233—C232	1.297 (4)	C134—C135	1.345 (5)
N233—C234	1.389 (4)	C134—H134	0.9500
C12—C13	1.354 (4)	C135—C136	1.501 (4)
C12—H12	0.9500	C136—H13A	0.9800
C13—C14	1.451 (4)	C136—H13B	0.9800
C13—C137	1.490 (4)	C136—H13C	0.9800
C14—C14A	1.472 (4)	C234—C235	1.346 (5)
C15—C16	1.379 (4)	C234—H234	0.9500
C15—C14A	1.407 (4)	C235—C236	1.499 (4)
C15—H15	0.9500	C236—H23A	0.9800
C14A—C18A	1.381 (4)	C236—H23B	0.9800
C16—C17	1.401 (4)	C236—H23C	0.9800
C132—S131—C135	88.76 (15)	C28A—C24A—C25	118.3 (3)
C235—S231—C232	88.58 (16)	C28A—C24A—C24	119.7 (3)
C12—O11—C18A	118.0 (2)	C25—C24A—C24	122.0 (3)
C22—O21—C28A	118.4 (2)	C25—C26—C27	120.6 (3)
C137—N13—C132	124.6 (3)	C25—C26—H26	119.7
C137—N13—H13	116 (3)	C27—C26—H26	119.7
C132—N13—H13	119 (3)	C28—C27—C26	120.3 (3)
C237—N23—C232	123.9 (3)	C28—C27—H27	119.9
C237—N23—H23	120 (3)	C26—C27—H27	119.9
C232—N23—H23	116 (3)	C27—C28—C28A	118.6 (3)
C132—N133—C134	109.0 (3)	C27—C28—H28	120.7
C232—N233—C234	109.1 (3)	C28A—C28—H28	120.7
O11—C12—C13	125.3 (3)	O21—C28A—C24A	122.1 (3)
O11—C12—H12	117.3	O21—C28A—C28	115.8 (3)
C13—C12—H12	117.3	C24A—C28A—C28	122.1 (3)
C12—C13—C14	119.7 (3)	N133—C132—N13	121.3 (3)
C12—C13—C137	116.1 (3)	N133—C132—S131	115.8 (2)
C14—C13—C137	124.1 (3)	N13—C132—S131	122.9 (2)
O14—C14—C13	123.9 (3)	C135—C134—N133	117.5 (3)
O14—C14—C14A	121.3 (3)	C135—C134—H134	121.3
C13—C14—C14A	114.7 (3)	N133—C134—H134	121.3
C16—C15—C14A	119.3 (3)	C134—C135—C136	128.4 (3)
C16—C15—H15	120.3	C134—C135—S131	109.0 (2)
C14A—C15—H15	120.3	C136—C135—S131	122.6 (3)
C18A—C14A—C15	119.0 (3)	C135—C136—H13A	109.5
C18A—C14A—C14	119.8 (3)	C135—C136—H13B	109.5
C15—C14A—C14	121.2 (3)	H13A—C136—H13B	109.5
C15—C16—C17	120.8 (3)	C135—C136—H13C	109.5
C15—C16—H16	119.6	H13A—C136—H13C	109.5
C17—C16—H16	119.6	H13B—C136—H13C	109.5
C18—C17—C16	120.7 (3)	O131—C137—N13	122.1 (3)
C18—C17—H17	119.7	O131—C137—C13	122.6 (3)
C16—C17—H17	119.7	N13—C137—C13	115.2 (3)
C17—C18—C18A	118.1 (3)	N233—C232—N23	121.4 (3)
C17—C18—H18	120.9	N233—C232—S231	115.9 (2)
C18A—C18—H18	120.9	N23—C232—S231	122.7 (2)
O11—C18A—C14A	122.4 (3)	C235—C234—N233	117.1 (3)
O11—C18A—C18	115.6 (3)	C235—C234—H234	121.5
C14A—C18A—C18	122.0 (3)	N233—C234—H234	121.5
O21—C22—C23	124.7 (3)	C234—C235—C236	129.3 (3)
O21—C22—H22	117.7	C234—C235—S231	109.3 (2)
C23—C22—H22	117.7	C236—C235—S231	121.4 (3)
C22—C23—C24	120.6 (3)	C235—C236—H23A	109.5
C22—C23—C237	115.3 (3)	C235—C236—H23B	109.5
C24—C23—C237	124.1 (3)	H23A—C236—H23B	109.5
O24—C24—C23	124.2 (3)	C235—C236—H23C	109.5
O24—C24—C24A	121.4 (3)	H23A—C236—H23C	109.5
C23—C24—C24A	114.5 (3)	H23B—C236—H23C	109.5
C26—C25—C24A	120.1 (3)	O231—C237—N23	121.7 (3)
C26—C25—H25	119.9	O231—C237—C23	122.1 (3)
C24A—C25—H25	119.9	N23—C237—C23	116.1 (3)
C18A—O11—C12—C13	0.1 (4)	C22—O21—C28A—C28	−177.2 (2)
O11—C12—C13—C14	−1.3 (4)	C25—C24A—C28A—O21	−178.9 (2)
O11—C12—C13—C137	−179.4 (2)	C24—C24A—C28A—O21	−0.6 (4)
C12—C13—C14—O14	−178.1 (3)	C25—C24A—C28A—C28	1.0 (4)
C137—C13—C14—O14	−0.1 (4)	C24—C24A—C28A—C28	179.3 (2)
C12—C13—C14—C14A	1.5 (4)	C27—C28—C28A—O21	178.0 (2)
C137—C13—C14—C14A	179.4 (2)	C27—C28—C28A—C24A	−1.8 (4)
C16—C15—C14A—C18A	−0.5 (4)	C134—N133—C132—N13	179.2 (2)
C16—C15—C14A—C14	179.7 (2)	C134—N133—C132—S131	0.4 (3)
O14—C14—C14A—C18A	178.9 (2)	C137—N13—C132—N133	178.4 (3)
C13—C14—C14A—C18A	−0.6 (4)	C137—N13—C132—S131	−2.9 (4)
O14—C14—C14A—C15	−1.2 (4)	C135—S131—C132—N133	−0.5 (2)
C13—C14—C14A—C15	179.2 (2)	C135—S131—C132—N13	−179.2 (2)
C14A—C15—C16—C17	0.8 (4)	C132—N133—C134—C135	−0.1 (4)
C15—C16—C17—C18	−0.5 (4)	N133—C134—C135—C136	−179.3 (3)
C16—C17—C18—C18A	−0.1 (4)	N133—C134—C135—S131	−0.3 (4)
C12—O11—C18A—C14A	0.8 (4)	C132—S131—C135—C134	0.4 (2)
C12—O11—C18A—C18	−179.4 (2)	C132—S131—C135—C136	179.5 (2)
C15—C14A—C18A—O11	179.6 (2)	C132—N13—C137—O131	2.8 (4)
C14—C14A—C18A—O11	−0.5 (4)	C132—N13—C137—C13	−176.9 (2)
C15—C14A—C18A—C18	−0.1 (4)	C12—C13—C137—O131	−5.8 (4)
C14—C14A—C18A—C18	179.7 (2)	C14—C13—C137—O131	176.1 (3)
C17—C18—C18A—O11	−179.3 (2)	C12—C13—C137—N13	173.8 (2)
C17—C18—C18A—C14A	0.4 (4)	C14—C13—C137—N13	−4.2 (4)
C28A—O21—C22—C23	−2.9 (4)	C234—N233—C232—N23	179.0 (2)
O21—C22—C23—C24	1.0 (4)	C234—N233—C232—S231	0.5 (3)
O21—C22—C23—C237	−178.0 (2)	C237—N23—C232—N233	179.0 (3)
C22—C23—C24—O24	−179.2 (3)	C237—N23—C232—S231	−2.6 (4)
C237—C23—C24—O24	−0.3 (4)	C235—S231—C232—N233	−0.4 (2)
C22—C23—C24—C24A	1.2 (4)	C235—S231—C232—N23	−178.9 (2)
C237—C23—C24—C24A	−180.0 (2)	C232—N233—C234—C235	−0.3 (4)
C26—C25—C24A—C28A	0.3 (4)	N233—C234—C235—C236	−178.9 (3)
C26—C25—C24A—C24	−177.9 (3)	N233—C234—C235—S231	0.0 (3)
O24—C24—C24A—C28A	179.0 (3)	C232—S231—C235—C234	0.2 (2)
C23—C24—C24A—C28A	−1.3 (4)	C232—S231—C235—C236	179.2 (2)
O24—C24—C24A—C25	−2.8 (4)	C232—N23—C237—O231	0.0 (4)
C23—C24—C24A—C25	176.9 (2)	C232—N23—C237—C23	−179.7 (2)
C24A—C25—C26—C27	−0.8 (4)	C22—C23—C237—O231	−0.6 (4)
C25—C26—C27—C28	0.0 (4)	C24—C23—C237—O231	−179.5 (3)
C26—C27—C28—C28A	1.3 (4)	C22—C23—C237—N23	179.2 (2)
C22—O21—C28A—C24A	2.7 (4)	C24—C23—C237—N23	0.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N13—H13···O14	0.80 (4)	1.99 (4)	2.671 (3)	143 (4)
C12—H12···O24^i	0.95	2.27	2.963 (4)	129
C15—H15···O23^ii	0.95	2.43	3.353 (4)	164
C136—H13C···O13^iii	0.98	2.51	3.449 (4)	162
N23—H23···O24	0.82 (4)	2.05 (3)	2.697 (3)	136 (3)
C22—H22···O14^ii	0.95	2.19	2.999 (4)	142
C25—H25···O13^iv	0.95	2.48	3.352 (4)	153

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