Methyl 3-[3-tert-butyl-5-(6-chloro-1-oxybenzotriazol-2-yl)-4-hydroxy­phen­yl]propionate

In the title compound, C₂₀H₂₂ClN₃O₄, the dihedral angle between the benzotriazole plane and the benzene plane is 38.2 (7)°. Intra­molecular O—H...O and O—H...N hydrogen bonds are present.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.045
• wR factor = 0.129
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.640     1.000
            Tmin(prime) and Tmax expected:      0.943     0.970
            RR(prime) =      0.658
            Please check that your absorption correction is appropriate.
SYMMS02_ALERT_1_B  All angles should not be 90 for a monoclinic cell
  Cell       8.4380    9.7980   24.3750
  Angles    90.0000   90.0000   90.0000
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.66

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.97
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10

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

   1 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
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Methyl 3-[3-tert-butyl-5-(6-chloro-1-oxybenzotriazol-2-yl)-4-hydroxyphenyl]propionate

Crystal data

C20H22ClN3O4	F(000) = 848
Mr = 403.86	Dx = 1.334 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2655 reflections
a = 8.438 (6) Å	θ = 2.2–24.3°
b = 9.798 (7) Å	µ = 0.22 mm^−1
c = 24.375 (15) Å	T = 294 K
β = 90.00 (5)°	Block, yellow
V = 2015 (2) Å^3	0.26 × 0.18 × 0.14 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	3567 independent reflections
Radiation source: fine-focus sealed tube	2157 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→7
Tmin = 0.640, Tmax = 1.000	k = −11→11
10090 measured reflections	l = −26→28

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.129	w = 1/[σ^2(Fo^2) + (0.0608P)^2 + 0.5063P] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max = 0.030
3567 reflections	Δρmax = 0.29 e Å^−3
259 parameters	Δρmin = −0.26 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0212 (17)

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.

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
Cl1	0.10306 (11)	0.78330 (9)	1.15331 (3)	0.0773 (3)
O1	0.4173 (2)	0.60181 (19)	0.95762 (7)	0.0562 (5)
O2	0.3486 (3)	0.51621 (19)	0.86138 (7)	0.0575 (6)
H2	0.3626	0.5597	0.8897	0.086*
O3	0.7371 (2)	0.00855 (18)	0.96059 (7)	0.0507 (5)
O4	0.8943 (2)	−0.0936 (2)	0.89913 (7)	0.0551 (5)
N1	0.3167 (3)	0.5238 (2)	0.98298 (8)	0.0437 (6)
N2	0.1773 (2)	0.3326 (2)	0.99971 (8)	0.0451 (6)
N3	0.2807 (2)	0.3944 (2)	0.96644 (8)	0.0417 (5)
C1	0.2311 (3)	0.5474 (3)	1.02919 (10)	0.0420 (6)
C2	0.2232 (3)	0.6638 (3)	1.06303 (11)	0.0502 (7)
H2A	0.2801	0.7432	1.0560	0.060*
C3	0.1244 (3)	0.6496 (3)	1.10701 (11)	0.0499 (7)
C4	0.0356 (3)	0.5307 (3)	1.11761 (11)	0.0512 (7)
H4	−0.0306	0.5284	1.1481	0.061*
C5	0.0441 (3)	0.4196 (3)	1.08453 (11)	0.0507 (7)
H5	−0.0152	0.3416	1.0917	0.061*
C6	0.1467 (3)	0.4272 (3)	1.03880 (10)	0.0409 (6)
C7	0.3532 (3)	0.3210 (3)	0.92172 (9)	0.0399 (6)
C8	0.3808 (3)	0.3815 (3)	0.87067 (10)	0.0443 (7)
C9	0.4355 (3)	0.2990 (3)	0.82739 (10)	0.0453 (7)
C10	0.4668 (4)	0.3599 (3)	0.76978 (10)	0.0585 (8)
C11	0.5920 (4)	0.4729 (4)	0.77315 (13)	0.0794 (11)
H11A	0.5539	0.5452	0.7963	0.119*
H11B	0.6123	0.5080	0.7371	0.119*
H11C	0.6881	0.4364	0.7882	0.119*
C12	0.3116 (5)	0.4183 (4)	0.74618 (13)	0.0928 (13)
H12A	0.2337	0.3470	0.7439	0.139*
H12B	0.3310	0.4545	0.7102	0.139*
H12C	0.2733	0.4896	0.7697	0.139*
C13	0.5272 (5)	0.2502 (4)	0.72976 (12)	0.0897 (12)
H13A	0.6228	0.2105	0.7439	0.134*
H13B	0.5482	0.2911	0.6947	0.134*
H13C	0.4482	0.1804	0.7257	0.134*
C14	0.4594 (3)	0.1616 (3)	0.83815 (10)	0.0454 (7)
H14	0.4942	0.1065	0.8095	0.054*
C15	0.4345 (3)	0.1004 (3)	0.88936 (10)	0.0409 (6)
C16	0.3813 (3)	0.1833 (3)	0.93129 (10)	0.0407 (6)
H16	0.3642	0.1469	0.9660	0.049*
C17	0.4586 (3)	−0.0514 (3)	0.89814 (11)	0.0471 (7)
H17A	0.3794	−0.1001	0.8769	0.057*
H17B	0.4394	−0.0717	0.9365	0.057*
C18	0.6211 (3)	−0.1067 (3)	0.88279 (11)	0.0488 (7)
H18A	0.6183	−0.2056	0.8846	0.059*
H18B	0.6442	−0.0813	0.8452	0.059*
C19	0.7527 (3)	−0.0559 (3)	0.91911 (10)	0.0420 (6)
C20	1.0318 (4)	−0.0538 (4)	0.93083 (14)	0.0817 (11)
H20A	1.0297	0.0431	0.9368	0.123*
H20B	1.1263	−0.0778	0.9112	0.123*
H20C	1.0304	−0.1001	0.9655	0.123*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0957 (7)	0.0720 (6)	0.0642 (5)	−0.0010 (5)	0.0192 (5)	−0.0221 (4)
O1	0.0584 (12)	0.0566 (12)	0.0537 (11)	−0.0175 (10)	0.0165 (10)	0.0015 (9)
O2	0.0759 (15)	0.0535 (12)	0.0432 (10)	0.0047 (11)	0.0079 (10)	0.0109 (9)
O3	0.0574 (12)	0.0582 (12)	0.0364 (10)	0.0001 (9)	0.0061 (9)	−0.0058 (9)
O4	0.0424 (11)	0.0718 (13)	0.0512 (11)	−0.0012 (10)	0.0061 (9)	−0.0145 (10)
N1	0.0434 (13)	0.0462 (13)	0.0417 (12)	−0.0078 (11)	0.0066 (10)	0.0013 (10)
N2	0.0485 (14)	0.0484 (13)	0.0382 (12)	−0.0019 (11)	0.0116 (10)	0.0067 (10)
N3	0.0448 (13)	0.0445 (13)	0.0357 (11)	−0.0034 (10)	0.0067 (10)	0.0014 (10)
C1	0.0393 (15)	0.0507 (16)	0.0360 (14)	−0.0005 (13)	0.0043 (12)	0.0029 (12)
C2	0.0501 (17)	0.0503 (17)	0.0502 (16)	−0.0036 (14)	0.0044 (14)	−0.0053 (14)
C3	0.0528 (17)	0.0550 (17)	0.0420 (15)	0.0068 (15)	0.0024 (13)	−0.0022 (14)
C4	0.0523 (18)	0.0593 (18)	0.0420 (15)	0.0092 (15)	0.0132 (13)	0.0057 (14)
C5	0.0532 (18)	0.0510 (17)	0.0480 (16)	0.0004 (14)	0.0135 (14)	0.0078 (14)
C6	0.0424 (15)	0.0454 (15)	0.0348 (13)	0.0030 (13)	0.0069 (12)	0.0045 (12)
C7	0.0393 (15)	0.0472 (16)	0.0331 (13)	−0.0012 (12)	0.0048 (11)	0.0020 (12)
C8	0.0457 (16)	0.0496 (17)	0.0376 (14)	−0.0001 (13)	0.0012 (12)	0.0102 (12)
C9	0.0452 (16)	0.0591 (18)	0.0317 (13)	−0.0019 (14)	0.0039 (12)	0.0051 (13)
C10	0.072 (2)	0.072 (2)	0.0322 (14)	0.0033 (17)	0.0079 (14)	0.0123 (14)
C11	0.093 (3)	0.084 (2)	0.061 (2)	−0.010 (2)	0.0210 (19)	0.0272 (18)
C12	0.096 (3)	0.135 (3)	0.0471 (19)	0.019 (3)	−0.0108 (19)	0.025 (2)
C13	0.135 (4)	0.098 (3)	0.0359 (17)	0.008 (2)	0.030 (2)	0.0107 (17)
C14	0.0489 (17)	0.0550 (17)	0.0323 (13)	−0.0003 (14)	0.0052 (12)	−0.0008 (12)
C15	0.0378 (15)	0.0478 (15)	0.0372 (14)	−0.0026 (12)	0.0026 (12)	0.0017 (12)
C16	0.0403 (15)	0.0513 (16)	0.0305 (13)	−0.0040 (12)	0.0022 (11)	0.0083 (12)
C17	0.0427 (17)	0.0476 (16)	0.0510 (16)	−0.0044 (13)	0.0022 (13)	0.0028 (13)
C18	0.0522 (18)	0.0482 (16)	0.0461 (15)	−0.0006 (14)	0.0005 (13)	−0.0065 (13)
C19	0.0484 (17)	0.0432 (15)	0.0344 (14)	0.0012 (13)	0.0070 (13)	0.0037 (12)
C20	0.046 (2)	0.115 (3)	0.084 (2)	−0.0057 (19)	−0.0016 (18)	−0.032 (2)

Geometric parameters (Å, º)

Cl1—C3	1.739 (3)	C10—C11	1.532 (5)
O1—N1	1.299 (2)	C10—C13	1.539 (4)
O2—C8	1.367 (3)	C10—C12	1.541 (4)
O2—H2	0.8200	C11—H11A	0.9600
O3—C19	1.199 (3)	C11—H11B	0.9600
O4—C19	1.343 (3)	C11—H11C	0.9600
O4—C20	1.447 (3)	C12—H12A	0.9600
N1—C1	1.358 (3)	C12—H12B	0.9600
N1—N3	1.364 (3)	C12—H12C	0.9600
N2—N3	1.337 (3)	C13—H13A	0.9600
N2—C6	1.354 (3)	C13—H13B	0.9600
N3—C7	1.442 (3)	C13—H13C	0.9600
C1—C6	1.396 (4)	C14—C15	1.400 (3)
C1—C2	1.409 (4)	C14—H14	0.9300
C2—C3	1.365 (4)	C15—C16	1.380 (3)
C2—H2A	0.9300	C15—C17	1.517 (4)
C3—C4	1.408 (4)	C16—H16	0.9300
C4—C5	1.357 (4)	C17—C18	1.521 (4)
C4—H4	0.9300	C17—H17A	0.9700
C5—C6	1.413 (4)	C17—H17B	0.9700
C5—H5	0.9300	C18—C19	1.505 (4)
C7—C16	1.390 (4)	C18—H18A	0.9700
C7—C8	1.398 (3)	C18—H18B	0.9700
C8—C9	1.406 (4)	C20—H20A	0.9600
C9—C14	1.387 (4)	C20—H20B	0.9600
C9—C10	1.549 (3)	C20—H20C	0.9600
C8—O2—H2	109.5	C10—C11—H11C	109.5
C19—O4—C20	116.4 (2)	H11A—C11—H11C	109.5
O1—N1—C1	129.9 (2)	H11B—C11—H11C	109.5
O1—N1—N3	123.47 (19)	C10—C12—H12A	109.5
C1—N1—N3	106.6 (2)	C10—C12—H12B	109.5
N3—N2—C6	103.9 (2)	H12A—C12—H12B	109.5
N2—N3—N1	112.79 (19)	C10—C12—H12C	109.5
N2—N3—C7	120.6 (2)	H12A—C12—H12C	109.5
N1—N3—C7	126.4 (2)	H12B—C12—H12C	109.5
N1—C1—C6	105.5 (2)	C10—C13—H13A	109.5
N1—C1—C2	130.5 (2)	C10—C13—H13B	109.5
C6—C1—C2	124.1 (2)	H13A—C13—H13B	109.5
C3—C2—C1	113.9 (3)	C10—C13—H13C	109.5
C3—C2—H2A	123.0	H13A—C13—H13C	109.5
C1—C2—H2A	123.0	H13B—C13—H13C	109.5
C2—C3—C4	123.6 (3)	C9—C14—C15	124.2 (2)
C2—C3—Cl1	119.7 (2)	C9—C14—H14	117.9
C4—C3—Cl1	116.7 (2)	C15—C14—H14	117.9
C5—C4—C3	121.8 (2)	C16—C15—C14	117.2 (2)
C5—C4—H4	119.1	C16—C15—C17	121.1 (2)
C3—C4—H4	119.1	C14—C15—C17	121.7 (2)
C4—C5—C6	117.3 (3)	C15—C16—C7	120.2 (2)
C4—C5—H5	121.4	C15—C16—H16	119.9
C6—C5—H5	121.4	C7—C16—H16	119.9
N2—C6—C1	111.2 (2)	C15—C17—C18	115.8 (2)
N2—C6—C5	129.5 (2)	C15—C17—H17A	108.3
C1—C6—C5	119.3 (2)	C18—C17—H17A	108.3
C16—C7—C8	122.2 (2)	C15—C17—H17B	108.3
C16—C7—N3	115.5 (2)	C18—C17—H17B	108.3
C8—C7—N3	122.1 (2)	H17A—C17—H17B	107.4
O2—C8—C7	121.6 (2)	C19—C18—C17	113.8 (2)
O2—C8—C9	119.7 (2)	C19—C18—H18A	108.8
C7—C8—C9	118.6 (2)	C17—C18—H18A	108.8
C14—C9—C8	117.6 (2)	C19—C18—H18B	108.8
C14—C9—C10	121.4 (2)	C17—C18—H18B	108.8
C8—C9—C10	121.0 (2)	H18A—C18—H18B	107.7
C11—C10—C13	108.1 (3)	O3—C19—O4	123.3 (2)
C11—C10—C12	109.8 (3)	O3—C19—C18	126.1 (2)
C13—C10—C12	107.7 (3)	O4—C19—C18	110.6 (2)
C11—C10—C9	110.4 (2)	O4—C20—H20A	109.5
C13—C10—C9	111.2 (2)	O4—C20—H20B	109.5
C12—C10—C9	109.6 (2)	H20A—C20—H20B	109.5
C10—C11—H11A	109.5	O4—C20—H20C	109.5
C10—C11—H11B	109.5	H20A—C20—H20C	109.5
H11A—C11—H11B	109.5	H20B—C20—H20C	109.5
C6—N2—N3—N1	0.1 (3)	C16—C7—C8—O2	178.2 (2)
C6—N2—N3—C7	174.5 (2)	N3—C7—C8—O2	3.7 (4)
O1—N1—N3—N2	178.3 (2)	C16—C7—C8—C9	1.5 (4)
C1—N1—N3—N2	−0.5 (3)	N3—C7—C8—C9	−173.0 (2)
O1—N1—N3—C7	4.3 (4)	O2—C8—C9—C14	−177.0 (2)
C1—N1—N3—C7	−174.5 (2)	C7—C8—C9—C14	−0.3 (4)
O1—N1—C1—C6	−178.1 (2)	O2—C8—C9—C10	2.7 (4)
N3—N1—C1—C6	0.6 (3)	C7—C8—C9—C10	179.5 (2)
O1—N1—C1—C2	1.2 (5)	C14—C9—C10—C11	−120.8 (3)
N3—N1—C1—C2	179.9 (3)	C8—C9—C10—C11	59.5 (4)
N1—C1—C2—C3	−179.1 (3)	C14—C9—C10—C13	−0.8 (4)
C6—C1—C2—C3	0.1 (4)	C8—C9—C10—C13	179.5 (3)
C1—C2—C3—C4	−1.0 (4)	C14—C9—C10—C12	118.2 (3)
C1—C2—C3—Cl1	179.24 (19)	C8—C9—C10—C12	−61.5 (4)
C2—C3—C4—C5	0.9 (4)	C8—C9—C14—C15	−0.8 (4)
Cl1—C3—C4—C5	−179.4 (2)	C10—C9—C14—C15	179.5 (2)
C3—C4—C5—C6	0.3 (4)	C9—C14—C15—C16	0.7 (4)
N3—N2—C6—C1	0.3 (3)	C9—C14—C15—C17	178.3 (3)
N3—N2—C6—C5	179.2 (3)	C14—C15—C16—C7	0.6 (4)
N1—C1—C6—N2	−0.6 (3)	C17—C15—C16—C7	−177.1 (2)
C2—C1—C6—N2	−180.0 (2)	C8—C7—C16—C15	−1.7 (4)
N1—C1—C6—C5	−179.6 (2)	N3—C7—C16—C15	173.1 (2)
C2—C1—C6—C5	1.0 (4)	C16—C15—C17—C18	−126.7 (3)
C4—C5—C6—N2	−180.0 (3)	C14—C15—C17—C18	55.8 (3)
C4—C5—C6—C1	−1.2 (4)	C15—C17—C18—C19	67.3 (3)
N2—N3—C7—C16	−33.3 (3)	C20—O4—C19—O3	0.7 (4)
N1—N3—C7—C16	140.3 (2)	C20—O4—C19—C18	−178.7 (2)
N2—N3—C7—C8	141.5 (3)	C17—C18—C19—O3	8.7 (4)
N1—N3—C7—C8	−44.9 (4)	C17—C18—C19—O4	−171.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	1.77	2.558 (3)	161
O2—H2···N1	0.82	2.33	2.978 (3)	136