Indomethacin tert-butanol solvate at 120 K

Crystals of the title compound, C₁₉H₁₆ClNO₄·C₄H₁₀O, contain O—H...O, C—H...O and C—H...π interactions.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.036
• wR factor = 0.091
• Data-to-parameter ratio = 17.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2002); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I)

Crystal data

C19H16ClNO4·C4H10O	F(000) = 912
Mr = 431.9	Dx = 1.321 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 27193 reflections
a = 11.9806 (1) Å	θ = 2.9–27.5°
b = 12.2749 (1) Å	µ = 0.21 mm^−1
c = 14.7679 (2) Å	T = 120 K
β = 91.561 (4)°	Prism, colourless
V = 2170.97 (4) Å^3	0.56 × 0.4 × 0.24 mm
Z = 4

Data collection

Nonius KappaCCD area-detector diffractometer	4405 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.047
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	θmax = 27.5°, θmin = 3.2°
Tmin = 0.877, Tmax = 0.957	h = −15→14
26128 measured reflections	k = −15→15
4955 independent reflections	l = −19→17

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.036	w = 1/[σ^2(Fo^2) + (0.0405P)^2 + 0.9973P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.092	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.27 e Å^−3
4955 reflections	Δρmin = −0.31 e Å^−3
282 parameters

Special details

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.

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

	x	y	z	Uiso*/Ueq
Cl1	0.53744 (3)	0.11454 (2)	0.05621 (2)	0.02768 (10)
O1	0.39237 (9)	0.49721 (8)	0.34830 (6)	0.0305 (2)
O2	0.80140 (7)	0.81999 (8)	0.06995 (6)	0.0254 (2)
O3	0.50660 (7)	0.99582 (7)	0.33048 (6)	0.0236 (2)
O4	0.32713 (8)	0.97083 (9)	0.36370 (7)	0.0299 (2)
H4	0.3480 (14)	1.0012 (15)	0.4161 (12)	0.036*
N1	0.45321 (8)	0.61486 (8)	0.24050 (7)	0.0174 (2)
C2	0.38544 (10)	0.70631 (10)	0.25850 (8)	0.0175 (2)
C3	0.43169 (9)	0.79601 (9)	0.22054 (8)	0.0164 (2)
C4	0.53547 (9)	0.76410 (9)	0.18074 (7)	0.0158 (2)
C5	0.61917 (10)	0.82526 (10)	0.14003 (8)	0.0170 (2)
H5A	0.6115	0.9017	0.1319	0.02*
C6	0.71351 (10)	0.77079 (10)	0.11206 (8)	0.0188 (2)
C7	0.72567 (10)	0.65809 (10)	0.12564 (9)	0.0216 (3)
H7	0.7916	0.6229	0.1064	0.026*
C8	0.64368 (10)	0.59707 (10)	0.16644 (8)	0.0203 (2)
H8	0.6527	0.521	0.1762	0.024*
C9	0.54714 (10)	0.65136 (10)	0.19282 (8)	0.0166 (2)
C10	0.43581 (10)	0.51033 (10)	0.27556 (8)	0.0196 (2)
C11	0.46740 (10)	0.41597 (9)	0.21822 (8)	0.0175 (2)
C12	0.44942 (10)	0.41659 (10)	0.12441 (8)	0.0185 (2)
H12	0.4234	0.4809	0.0949	0.022*
C13	0.46952 (10)	0.32326 (10)	0.07407 (8)	0.0192 (2)
H13	0.4563	0.3225	0.0104	0.023*
C14	0.50936 (10)	0.23112 (9)	0.11890 (8)	0.0188 (2)
C15	0.52904 (10)	0.22873 (10)	0.21180 (8)	0.0203 (2)
H15	0.5572	0.1649	0.2408	0.024*
C16	0.50667 (10)	0.32171 (10)	0.26147 (8)	0.0199 (2)
H16	0.5181	0.3213	0.3254	0.024*
C17	0.27818 (10)	0.69725 (11)	0.30715 (9)	0.0232 (3)
H17A	0.294	0.6882	0.3722	0.03*
H17B	0.2361	0.6341	0.2842	0.03*
H17C	0.234	0.7635	0.297	0.03*
C18	0.38432 (10)	0.90966 (10)	0.22037 (8)	0.0191 (2)
H18A	0.3022	0.9066	0.211	0.025*
H18B	0.4158	0.9522	0.1701	0.025*
C19	0.41293 (10)	0.96445 (9)	0.30993 (8)	0.0179 (2)
C20	0.79578 (12)	0.93475 (12)	0.05756 (11)	0.0326 (3)
H20A	0.7296	0.953	0.0201	0.042*
H20B	0.863	0.9599	0.0274	0.042*
H20C	0.7909	0.9705	0.1166	0.042*
O5	0.36383 (9)	0.06827 (8)	0.51688 (6)	0.0293 (2)
H51	0.4084 (15)	0.0423 (15)	0.5603 (12)	0.035*
C21	0.35108 (11)	0.18542 (10)	0.52502 (8)	0.0216 (3)
C22	0.27654 (13)	0.22029 (13)	0.44516 (9)	0.0341 (3)
H22A	0.2052	0.1815	0.4472	0.044*
H22B	0.3133	0.2029	0.3885	0.044*
H22C	0.2631	0.2989	0.4484	0.044*
C23	0.46498 (14)	0.23816 (15)	0.52097 (13)	0.0466 (4)
H23A	0.5015	0.2151	0.4656	0.061*
H23B	0.5106	0.216	0.5739	0.061*
H23C	0.4566	0.3176	0.5208	0.061*
C24	0.29574 (13)	0.20767 (14)	0.61433 (9)	0.0367 (4)
H24A	0.3426	0.1788	0.6642	0.048*
H24B	0.2224	0.1722	0.6144	0.048*
H24C	0.2864	0.2864	0.6221	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.03772 (19)	0.01558 (15)	0.02960 (17)	0.00434 (12)	−0.00167 (13)	−0.00534 (11)
O1	0.0437 (6)	0.0250 (5)	0.0232 (5)	0.0010 (4)	0.0110 (4)	0.0006 (4)
O2	0.0198 (4)	0.0242 (5)	0.0325 (5)	0.0000 (3)	0.0081 (4)	0.0018 (4)
O3	0.0219 (4)	0.0217 (5)	0.0270 (5)	−0.0018 (3)	−0.0032 (4)	0.0007 (4)
O4	0.0229 (5)	0.0408 (6)	0.0262 (5)	−0.0010 (4)	0.0035 (4)	−0.0159 (4)
N1	0.0181 (5)	0.0148 (5)	0.0195 (5)	0.0008 (4)	0.0020 (4)	−0.0034 (4)
C2	0.0174 (6)	0.0179 (6)	0.0170 (5)	0.0019 (4)	−0.0010 (4)	−0.0046 (4)
C3	0.0167 (5)	0.0174 (6)	0.0149 (5)	0.0030 (4)	−0.0016 (4)	−0.0037 (4)
C4	0.0168 (5)	0.0172 (6)	0.0131 (5)	0.0025 (4)	−0.0019 (4)	−0.0031 (4)
C5	0.0190 (6)	0.0157 (5)	0.0161 (5)	0.0016 (4)	−0.0014 (4)	−0.0013 (4)
C6	0.0163 (5)	0.0218 (6)	0.0183 (5)	−0.0011 (4)	0.0002 (4)	−0.0016 (4)
C7	0.0169 (6)	0.0212 (6)	0.0269 (6)	0.0044 (5)	0.0021 (5)	−0.0045 (5)
C8	0.0201 (6)	0.0155 (6)	0.0253 (6)	0.0030 (4)	−0.0001 (5)	−0.0032 (5)
C9	0.0166 (5)	0.0170 (5)	0.0161 (5)	−0.0004 (4)	−0.0005 (4)	−0.0027 (4)
C10	0.0211 (6)	0.0182 (6)	0.0195 (6)	−0.0006 (4)	−0.0007 (4)	−0.0012 (4)
C11	0.0178 (5)	0.0147 (5)	0.0200 (6)	−0.0021 (4)	0.0008 (4)	−0.0012 (4)
C12	0.0194 (6)	0.0145 (5)	0.0215 (6)	0.0005 (4)	−0.0015 (4)	0.0016 (4)
C13	0.0202 (6)	0.0186 (6)	0.0186 (6)	−0.0007 (4)	−0.0025 (4)	−0.0007 (4)
C14	0.0185 (6)	0.0134 (5)	0.0245 (6)	−0.0011 (4)	0.0010 (4)	−0.0028 (4)
C15	0.0209 (6)	0.0153 (6)	0.0246 (6)	−0.0001 (4)	−0.0013 (5)	0.0047 (5)
C16	0.0220 (6)	0.0195 (6)	0.0180 (5)	−0.0023 (5)	−0.0010 (4)	0.0027 (4)
C17	0.0194 (6)	0.0240 (6)	0.0264 (6)	0.0002 (5)	0.0045 (5)	−0.0034 (5)
C18	0.0200 (6)	0.0178 (6)	0.0194 (6)	0.0056 (4)	−0.0013 (4)	−0.0014 (4)
C19	0.0214 (6)	0.0112 (5)	0.0211 (6)	0.0041 (4)	−0.0004 (4)	0.0002 (4)
C20	0.0321 (7)	0.0255 (7)	0.0408 (8)	−0.0015 (6)	0.0133 (6)	0.0051 (6)
O5	0.0399 (6)	0.0255 (5)	0.0221 (5)	0.0055 (4)	−0.0078 (4)	−0.0054 (4)
C21	0.0226 (6)	0.0227 (6)	0.0194 (6)	0.0010 (5)	−0.0030 (5)	0.0000 (5)
C22	0.0388 (8)	0.0385 (8)	0.0244 (7)	0.0064 (6)	−0.0090 (6)	0.0018 (6)
C23	0.0343 (8)	0.0483 (10)	0.0565 (10)	−0.0150 (7)	−0.0096 (7)	0.0267 (8)
C24	0.0398 (8)	0.0480 (9)	0.0223 (7)	0.0174 (7)	−0.0018 (6)	−0.0065 (6)

Geometric parameters (Å, º)

Cl1—C14	1.7422 (12)	C13—H13	0.95
O1—C10	1.2169 (15)	C14—C15	1.3860 (17)
O2—C6	1.3769 (14)	C15—C16	1.3868 (17)
O2—C20	1.4219 (17)	C15—H15	0.95
O3—C19	1.2170 (15)	C16—H16	0.95
O4—C19	1.3183 (15)	C17—H17A	0.98
O4—H4	0.889 (18)	C17—H17B	0.98
N1—C10	1.4014 (15)	C17—H17C	0.98
N1—C2	1.4148 (14)	C18—C19	1.5146 (16)
N1—C9	1.4164 (15)	C18—H18A	0.99
C2—C3	1.3604 (17)	C18—H18B	0.99
C2—C17	1.4934 (16)	C20—H20A	0.98
C3—C4	1.4438 (15)	C20—H20B	0.98
C3—C18	1.5061 (16)	C20—H20C	0.98
C4—C5	1.4013 (16)	O5—C21	1.4514 (16)
C4—C9	1.4019 (16)	O5—H51	0.883 (18)
C5—C6	1.3859 (16)	C21—C23	1.5130 (19)
C5—H5A	0.95	C21—C24	1.5170 (18)
C6—C7	1.4049 (18)	C21—C22	1.5213 (17)
C7—C8	1.3861 (18)	C22—H22A	0.98
C7—H7	0.95	C22—H22B	0.98
C8—C9	1.3992 (16)	C22—H22C	0.98
C8—H8	0.95	C23—H23A	0.98
C10—C11	1.4898 (16)	C23—H23B	0.98
C11—C12	1.3963 (17)	C23—H23C	0.98
C11—C16	1.3970 (17)	C24—H24A	0.98
C12—C13	1.3903 (17)	C24—H24B	0.98
C12—H12	0.95	C24—H24C	0.98
C13—C14	1.3886 (17)
C6—O2—C20	117.29 (10)	C15—C16—H16	119.8
C19—O4—H4	110.2 (11)	C11—C16—H16	119.8
C10—N1—C2	124.41 (10)	C2—C17—H17A	109.5
C10—N1—C9	126.97 (10)	C2—C17—H17B	109.5
C2—N1—C9	108.08 (9)	H17A—C17—H17B	109.5
C3—C2—N1	108.81 (10)	C2—C17—H17C	109.5
C3—C2—C17	128.62 (11)	H17A—C17—H17C	109.5
N1—C2—C17	122.48 (11)	H17B—C17—H17C	109.5
C2—C3—C4	108.25 (10)	C3—C18—C19	109.48 (9)
C2—C3—C18	126.35 (11)	C3—C18—H18A	109.8
C4—C3—C18	125.40 (11)	C19—C18—H18A	109.8
C5—C4—C9	120.89 (10)	C3—C18—H18B	109.8
C5—C4—C3	131.57 (11)	C19—C18—H18B	109.8
C9—C4—C3	107.46 (10)	H18A—C18—H18B	108.2
C6—C5—C4	117.93 (11)	O3—C19—O4	124.04 (11)
C6—C5—H5A	121	O3—C19—C18	122.92 (11)
C4—C5—H5A	121	O4—C19—C18	113.00 (10)
O2—C6—C5	124.26 (11)	O2—C20—H20A	109.5
O2—C6—C7	114.75 (10)	O2—C20—H20B	109.5
C5—C6—C7	120.99 (11)	H20A—C20—H20B	109.5
C8—C7—C6	121.48 (11)	O2—C20—H20C	109.5
C8—C7—H7	119.3	H20A—C20—H20C	109.5
C6—C7—H7	119.3	H20B—C20—H20C	109.5
C7—C8—C9	117.69 (11)	C21—O5—H51	111.2 (12)
C7—C8—H8	121.2	O5—C21—C23	108.88 (12)
C9—C8—H8	121.2	O5—C21—C24	107.45 (11)
C8—C9—C4	121.00 (11)	C23—C21—C24	111.93 (13)
C8—C9—N1	131.44 (11)	O5—C21—C22	105.99 (11)
C4—C9—N1	107.31 (10)	C23—C21—C22	111.10 (12)
O1—C10—N1	121.25 (11)	C24—C21—C22	111.23 (11)
O1—C10—C11	121.34 (11)	C21—C22—H22A	109.5
N1—C10—C11	117.33 (10)	C21—C22—H22B	109.5
C12—C11—C16	119.94 (11)	H22A—C22—H22B	109.5
C12—C11—C10	121.67 (11)	C21—C22—H22C	109.5
C16—C11—C10	118.14 (11)	H22A—C22—H22C	109.5
C13—C12—C11	120.12 (11)	H22B—C22—H22C	109.5
C13—C12—H12	119.9	C21—C23—H23A	109.5
C11—C12—H12	119.9	C21—C23—H23B	109.5
C14—C13—C12	118.59 (11)	H23A—C23—H23B	109.5
C14—C13—H13	120.7	C21—C23—H23C	109.5
C12—C13—H13	120.7	H23A—C23—H23C	109.5
C15—C14—C13	122.43 (11)	H23B—C23—H23C	109.5
C15—C14—Cl1	118.59 (9)	C21—C24—H24A	109.5
C13—C14—Cl1	118.98 (9)	C21—C24—H24B	109.5
C14—C15—C16	118.42 (11)	H24A—C24—H24B	109.5
C14—C15—H15	120.8	C21—C24—H24C	109.5
C16—C15—H15	120.8	H24A—C24—H24C	109.5
C15—C16—C11	120.49 (11)	H24B—C24—H24C	109.5
C10—N1—C2—C3	174.62 (11)	C10—N1—C9—C8	1.4 (2)
C9—N1—C2—C3	2.52 (13)	C2—N1—C9—C8	173.20 (12)
C10—N1—C2—C17	−8.62 (18)	C10—N1—C9—C4	−172.74 (11)
C9—N1—C2—C17	179.28 (10)	C2—N1—C9—C4	−0.90 (12)
N1—C2—C3—C4	−3.09 (13)	C2—N1—C10—O1	−29.24 (18)
C17—C2—C3—C4	−179.59 (11)	C9—N1—C10—O1	141.34 (13)
N1—C2—C3—C18	177.48 (10)	C2—N1—C10—C11	147.80 (11)
C17—C2—C3—C18	1.0 (2)	C9—N1—C10—C11	−41.62 (16)
C2—C3—C4—C5	−174.29 (12)	O1—C10—C11—C12	138.60 (13)
C18—C3—C4—C5	5.2 (2)	N1—C10—C11—C12	−38.43 (16)
C2—C3—C4—C9	2.52 (13)	O1—C10—C11—C16	−35.68 (18)
C18—C3—C4—C9	−178.04 (11)	N1—C10—C11—C16	147.28 (11)
C9—C4—C5—C6	0.09 (16)	C16—C11—C12—C13	0.61 (18)
C3—C4—C5—C6	176.55 (11)	C10—C11—C12—C13	−173.58 (11)
C20—O2—C6—C5	2.28 (18)	C11—C12—C13—C14	−1.11 (18)
C20—O2—C6—C7	−177.61 (12)	C12—C13—C14—C15	0.42 (18)
C4—C5—C6—O2	178.98 (11)	C12—C13—C14—Cl1	−178.76 (9)
C4—C5—C6—C7	−1.14 (17)	C13—C14—C15—C16	0.78 (18)
O2—C6—C7—C8	−179.40 (11)	Cl1—C14—C15—C16	179.95 (9)
C5—C6—C7—C8	0.70 (19)	C14—C15—C16—C11	−1.28 (18)
C6—C7—C8—C9	0.80 (18)	C12—C11—C16—C15	0.61 (18)
C7—C8—C9—C4	−1.85 (18)	C10—C11—C16—C15	175.00 (11)
C7—C8—C9—N1	−175.28 (12)	C2—C3—C18—C19	81.43 (14)
C5—C4—C9—C8	1.43 (17)	C4—C3—C18—C19	−97.92 (13)
C3—C4—C9—C8	−175.79 (10)	C3—C18—C19—O3	72.84 (15)
C5—C4—C9—N1	176.28 (10)	C3—C18—C19—O4	−104.93 (12)
C3—C4—C9—N1	−0.94 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O5^i	0.89 (2)	1.71 (2)	2.586 (1)	170 (2)
O5—H51···O3^ii	0.88 (2)	1.94 (2)	2.814 (1)	170 (2)
C15—H15···O3^iii	0.95	2.54	3.368 (1)	145

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