2-{5-[N-(4-tert-Butyl­benz­yl)carbamo­yl]-3-phenyl-1H-pyrazol-1-yl}acetic acid

In the title compound, C₂₃H₂₅N₃O₃, all bond lengths and angles show normal values. The dihedral angles between the rings of the pyrazole and the unsubstituted and tert-butyl-substituted benzene rings are 8.6 (2) and 78.5 (3)°, respectively, while that between the two benzene rings is 76.6 (3)°.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.135
• Data-to-parameter ratio = 18.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C20

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.800     0.980
            Tmin(prime) and Tmax expected:      0.962     0.982
            RR(prime) =      0.834
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.83
PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) .....         20 Ang.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.25 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.77 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C20    -   C21     ..       6.82 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      56.00 A   3 

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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: APEX2 Software Suite (Bruker, 2005); cell refinement: APEX2 Software Suite; data reduction: APEX2 Software Suite; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

2-{5-[N-(4-tert-Butylbenzyl)carbamoyl]-3-phenyl-1H-pyrazol-1-yl}acetic acid

Crystal data

C23H25N3O3	Dx = 1.187 Mg m^−3
Mr = 391.46	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/a	Cell parameters from 7040 reflections
Hall symbol: -I 4ad	θ = 2.3–24.2°
a = 23.2759 (2) Å	µ = 0.08 mm^−1
c = 16.1785 (2) Å	T = 295 K
V = 8764.99 (15) Å^3	Block, colourless
Z = 16	0.48 × 0.37 × 0.23 mm
F(000) = 3328

Data collection

Bruker APEX II CCD area-detector diffractometer	5017 independent reflections
Radiation source: fine-focus sealed tube	3365 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 27.5°, θmin = 1.5°
Absorption correction: multi-scan (APEX2 Software Suite; Bruker, 2005)	h = −30→26
Tmin = 0.80, Tmax = 0.98	k = −25→30
29541 measured reflections	l = −20→20

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)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.136	w = 1/[σ^2(Fo^2) + (0.0565P)^2 + 3.9441P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
5017 reflections	Δρmax = 0.20 e Å^−3
267 parameters	Δρmin = −0.13 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: 0.00052 (13)

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
C1	0.57132 (9)	0.45207 (10)	0.28091 (13)	0.0717 (6)
H1	0.5936	0.4520	0.3286	0.086*
C2	0.52422 (9)	0.48689 (10)	0.27489 (11)	0.0675 (5)
H2	0.5148	0.5111	0.3186	0.081*
C3	0.49044 (8)	0.48665 (8)	0.20464 (11)	0.0555 (4)
H3	0.4587	0.5109	0.2015	0.067*
C4	0.50318 (7)	0.45089 (7)	0.13905 (10)	0.0446 (4)
C5	0.55138 (8)	0.41631 (10)	0.14546 (13)	0.0708 (6)
H5	0.5612	0.3921	0.1020	0.085*
C6	0.58507 (9)	0.41754 (11)	0.21612 (15)	0.0819 (7)
H6	0.6176	0.3944	0.2192	0.098*
C7	0.46496 (6)	0.44901 (6)	0.06628 (9)	0.0412 (4)
C8	0.41125 (7)	0.47522 (7)	0.05703 (9)	0.0439 (4)
H8	0.3928	0.4990	0.0949	0.053*
C9	0.39131 (6)	0.45881 (6)	−0.01917 (9)	0.0411 (4)
C10	0.43330 (7)	0.39683 (7)	−0.13314 (10)	0.0476 (4)
H10A	0.4724	0.3857	−0.1462	0.057*
H10B	0.4207	0.4239	−0.1750	0.057*
C11	0.39560 (7)	0.34452 (7)	−0.13632 (11)	0.0505 (4)
C12	0.33644 (7)	0.47111 (7)	−0.06170 (9)	0.0440 (4)
C13	0.24560 (7)	0.52334 (7)	−0.05446 (11)	0.0524 (4)
H13A	0.2502	0.5295	−0.1134	0.063*
H13B	0.2355	0.5600	−0.0298	0.063*
C14	0.19628 (7)	0.48217 (7)	−0.04130 (10)	0.0475 (4)
C15	0.14116 (8)	0.50024 (9)	−0.05850 (14)	0.0707 (6)
H15	0.1350	0.5379	−0.0758	0.085*
C16	0.09480 (9)	0.46350 (9)	−0.05055 (15)	0.0778 (6)
H16	0.0582	0.4772	−0.0624	0.093*
C17	0.10115 (8)	0.40713 (8)	−0.02550 (12)	0.0569 (5)
C18	0.15619 (8)	0.39042 (8)	−0.00577 (13)	0.0649 (5)
H18	0.1623	0.3533	0.0135	0.078*
C19	0.20273 (8)	0.42693 (8)	−0.01361 (12)	0.0600 (5)
H19	0.2392	0.4137	0.0002	0.072*
C20	0.05027 (9)	0.36542 (9)	−0.02292 (14)	0.0722 (6)
C21	−0.00417 (11)	0.39569 (13)	0.0052 (2)	0.1116 (10)
H21A	0.0027	0.4142	0.0573	0.167*
H21B	−0.0345	0.3681	0.0112	0.167*
H21C	−0.0150	0.4239	−0.0352	0.167*
C22	0.04223 (14)	0.34079 (16)	−0.1081 (2)	0.1332 (13)
H22A	0.0353	0.3714	−0.1466	0.200*
H22B	0.0100	0.3150	−0.1080	0.200*
H22C	0.0762	0.3203	−0.1241	0.200*
C23	0.06115 (13)	0.31710 (13)	0.0392 (2)	0.1335 (13)
H23A	0.0929	0.2941	0.0207	0.200*
H23B	0.0274	0.2935	0.0436	0.200*
H23C	0.0700	0.3333	0.0922	0.200*
N1	0.47765 (5)	0.41840 (5)	−0.00148 (8)	0.0429 (3)
N2	0.43254 (5)	0.42502 (5)	−0.05312 (8)	0.0414 (3)
N3	0.30037 (6)	0.50499 (6)	−0.02066 (9)	0.0509 (4)
H3A	0.3099	0.5165	0.0280	0.061*
O1	0.39529 (7)	0.32381 (6)	−0.21188 (8)	0.0822 (5)
H1A	0.3752	0.2949	−0.2135	0.123*
O2	0.36976 (6)	0.32464 (6)	−0.07940 (8)	0.0716 (4)
O3	0.32525 (5)	0.45049 (5)	−0.12998 (7)	0.0595 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0603 (12)	0.0991 (16)	0.0559 (12)	−0.0177 (12)	−0.0171 (9)	0.0082 (11)
C2	0.0647 (12)	0.0893 (15)	0.0485 (10)	−0.0149 (11)	−0.0046 (9)	−0.0090 (10)
C3	0.0514 (10)	0.0644 (11)	0.0507 (10)	−0.0043 (8)	−0.0033 (8)	−0.0064 (8)
C4	0.0408 (8)	0.0464 (9)	0.0466 (9)	−0.0065 (7)	−0.0029 (7)	0.0010 (7)
C5	0.0621 (12)	0.0822 (14)	0.0681 (13)	0.0168 (11)	−0.0168 (10)	−0.0151 (11)
C6	0.0640 (13)	0.0957 (17)	0.0861 (16)	0.0141 (12)	−0.0259 (11)	−0.0015 (13)
C7	0.0405 (8)	0.0407 (8)	0.0423 (8)	−0.0057 (6)	0.0009 (6)	−0.0025 (6)
C8	0.0443 (9)	0.0456 (8)	0.0418 (8)	0.0020 (7)	−0.0010 (7)	−0.0078 (7)
C9	0.0416 (8)	0.0401 (8)	0.0415 (8)	−0.0022 (6)	0.0009 (6)	−0.0052 (6)
C10	0.0458 (9)	0.0535 (10)	0.0435 (9)	−0.0046 (7)	0.0044 (7)	−0.0116 (7)
C11	0.0544 (10)	0.0496 (10)	0.0473 (10)	−0.0029 (8)	−0.0025 (8)	−0.0090 (8)
C12	0.0461 (9)	0.0439 (8)	0.0419 (8)	−0.0016 (7)	−0.0048 (7)	−0.0063 (7)
C13	0.0496 (9)	0.0501 (9)	0.0576 (10)	0.0091 (8)	−0.0073 (8)	−0.0059 (8)
C14	0.0471 (9)	0.0498 (9)	0.0455 (9)	0.0076 (7)	−0.0042 (7)	−0.0062 (7)
C15	0.0562 (11)	0.0551 (11)	0.1009 (16)	0.0074 (9)	−0.0167 (11)	0.0153 (11)
C16	0.0471 (11)	0.0721 (14)	0.1141 (18)	0.0064 (10)	−0.0184 (11)	0.0165 (12)
C17	0.0529 (10)	0.0575 (11)	0.0604 (11)	0.0016 (8)	0.0020 (8)	−0.0030 (8)
C18	0.0611 (12)	0.0492 (10)	0.0842 (14)	0.0098 (9)	0.0059 (10)	0.0074 (9)
C19	0.0479 (10)	0.0565 (11)	0.0757 (13)	0.0140 (8)	−0.0013 (9)	0.0035 (9)
C20	0.0596 (12)	0.0699 (13)	0.0870 (15)	−0.0074 (10)	0.0040 (11)	−0.0026 (11)
C21	0.0689 (15)	0.113 (2)	0.153 (3)	−0.0150 (15)	0.0232 (16)	−0.0058 (19)
C22	0.118 (2)	0.157 (3)	0.125 (3)	−0.064 (2)	0.0124 (19)	−0.052 (2)
C23	0.103 (2)	0.104 (2)	0.194 (4)	−0.0355 (18)	−0.010 (2)	0.059 (2)
N1	0.0369 (7)	0.0458 (7)	0.0459 (7)	−0.0044 (5)	0.0003 (5)	−0.0048 (6)
N2	0.0388 (7)	0.0443 (7)	0.0409 (7)	−0.0043 (6)	0.0003 (5)	−0.0080 (5)
N3	0.0463 (8)	0.0582 (9)	0.0482 (8)	0.0081 (6)	−0.0090 (6)	−0.0155 (6)
O1	0.1122 (12)	0.0807 (10)	0.0539 (8)	−0.0426 (9)	0.0077 (7)	−0.0236 (7)
O2	0.0952 (10)	0.0618 (8)	0.0577 (8)	−0.0282 (7)	0.0091 (7)	−0.0070 (6)
O3	0.0597 (7)	0.0710 (8)	0.0479 (7)	0.0111 (6)	−0.0138 (5)	−0.0189 (6)

Geometric parameters (Å, º)

C1—C6	1.359 (3)	C13—H13A	0.9700
C1—C2	1.367 (3)	C13—H13B	0.9700
C1—H1	0.9300	C14—C19	1.370 (2)
C2—C3	1.382 (2)	C14—C15	1.379 (2)
C2—H2	0.9300	C15—C16	1.383 (3)
C3—C4	1.381 (2)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.381 (3)
C4—C5	1.385 (2)	C16—H16	0.9300
C4—C7	1.476 (2)	C17—C18	1.376 (3)
C5—C6	1.386 (3)	C17—C20	1.532 (3)
C5—H5	0.9300	C18—C19	1.383 (3)
C6—H6	0.9300	C18—H18	0.9300
C7—N1	1.3404 (19)	C19—H19	0.9300
C7—C8	1.399 (2)	C20—C22	1.504 (4)
C8—C9	1.372 (2)	C20—C21	1.520 (3)
C8—H8	0.9300	C20—C23	1.529 (4)
C9—N2	1.3568 (19)	C21—H21A	0.9600
C9—C12	1.479 (2)	C21—H21B	0.9600
C10—N2	1.4514 (19)	C21—H21C	0.9600
C10—C11	1.502 (2)	C22—H22A	0.9600
C10—H10A	0.9700	C22—H22B	0.9600
C10—H10B	0.9700	C22—H22C	0.9600
C11—O2	1.193 (2)	C23—H23A	0.9600
C11—O1	1.314 (2)	C23—H23B	0.9600
C12—O3	1.2322 (18)	C23—H23C	0.9600
C12—N3	1.330 (2)	N1—N2	1.3508 (17)
C13—N3	1.451 (2)	N3—H3A	0.8600
C13—C14	1.510 (2)	O1—H1A	0.8200
C6—C1—C2	118.98 (18)	C14—C15—C16	121.24 (18)
C6—C1—H1	120.5	C14—C15—H15	119.4
C2—C1—H1	120.5	C16—C15—H15	119.4
C1—C2—C3	120.84 (19)	C17—C16—C15	122.10 (18)
C1—C2—H2	119.6	C17—C16—H16	119.0
C3—C2—H2	119.6	C15—C16—H16	119.0
C4—C3—C2	120.81 (18)	C18—C17—C16	115.85 (17)
C4—C3—H3	119.6	C18—C17—C20	122.29 (17)
C2—C3—H3	119.6	C16—C17—C20	121.82 (17)
C3—C4—C5	117.82 (16)	C17—C18—C19	122.30 (17)
C3—C4—C7	120.09 (15)	C17—C18—H18	118.9
C5—C4—C7	122.06 (15)	C19—C18—H18	118.9
C4—C5—C6	120.53 (19)	C14—C19—C18	121.40 (17)
C4—C5—H5	119.7	C14—C19—H19	119.3
C6—C5—H5	119.7	C18—C19—H19	119.3
C1—C6—C5	121.0 (2)	C22—C20—C21	110.3 (2)
C1—C6—H6	119.5	C22—C20—C23	110.0 (3)
C5—C6—H6	119.5	C21—C20—C23	106.4 (2)
N1—C7—C8	109.95 (13)	C22—C20—C17	108.22 (19)
N1—C7—C4	122.36 (14)	C21—C20—C17	111.03 (19)
C8—C7—C4	127.65 (14)	C23—C20—C17	110.85 (19)
C9—C8—C7	106.09 (13)	C20—C21—H21A	109.5
C9—C8—H8	127.0	C20—C21—H21B	109.5
C7—C8—H8	127.0	H21A—C21—H21B	109.5
N2—C9—C8	106.62 (13)	C20—C21—H21C	109.5
N2—C9—C12	122.33 (13)	H21A—C21—H21C	109.5
C8—C9—C12	131.04 (14)	H21B—C21—H21C	109.5
N2—C10—C11	112.95 (13)	C20—C22—H22A	109.5
N2—C10—H10A	109.0	C20—C22—H22B	109.5
C11—C10—H10A	109.0	H22A—C22—H22B	109.5
N2—C10—H10B	109.0	C20—C22—H22C	109.5
C11—C10—H10B	109.0	H22A—C22—H22C	109.5
H10A—C10—H10B	107.8	H22B—C22—H22C	109.5
O2—C11—O1	124.95 (16)	C20—C23—H23A	109.5
O2—C11—C10	125.63 (15)	C20—C23—H23B	109.5
O1—C11—C10	109.42 (15)	H23A—C23—H23B	109.5
O3—C12—N3	123.05 (15)	C20—C23—H23C	109.5
O3—C12—C9	121.61 (14)	H23A—C23—H23C	109.5
N3—C12—C9	115.33 (13)	H23B—C23—H23C	109.5
N3—C13—C14	115.33 (14)	C7—N1—N2	105.90 (12)
N3—C13—H13A	108.4	N1—N2—C9	111.44 (12)
C14—C13—H13A	108.4	N1—N2—C10	119.39 (12)
N3—C13—H13B	108.4	C9—N2—C10	129.17 (13)
C14—C13—H13B	108.4	C12—N3—C13	122.75 (14)
H13A—C13—H13B	107.5	C12—N3—H3A	118.6
C19—C14—C15	117.03 (17)	C13—N3—H3A	118.6
C19—C14—C13	123.93 (15)	C11—O1—H1A	109.5
C15—C14—C13	119.04 (15)
C6—C1—C2—C3	0.9 (3)	C15—C16—C17—C18	2.5 (3)
C1—C2—C3—C4	0.5 (3)	C15—C16—C17—C20	−175.4 (2)
C2—C3—C4—C5	−1.3 (3)	C16—C17—C18—C19	−2.5 (3)
C2—C3—C4—C7	176.86 (16)	C20—C17—C18—C19	175.39 (19)
C3—C4—C5—C6	0.6 (3)	C15—C14—C19—C18	2.0 (3)
C7—C4—C5—C6	−177.44 (19)	C13—C14—C19—C18	−177.44 (18)
C2—C1—C6—C5	−1.5 (4)	C17—C18—C19—C14	0.3 (3)
C4—C5—C6—C1	0.7 (4)	C18—C17—C20—C22	−93.8 (3)
C3—C4—C7—N1	174.81 (15)	C16—C17—C20—C22	83.9 (3)
C5—C4—C7—N1	−7.1 (2)	C18—C17—C20—C21	145.0 (2)
C3—C4—C7—C8	−7.8 (2)	C16—C17—C20—C21	−37.3 (3)
C5—C4—C7—C8	170.21 (18)	C18—C17—C20—C23	26.9 (3)
N1—C7—C8—C9	0.60 (18)	C16—C17—C20—C23	−155.3 (2)
C4—C7—C8—C9	−177.02 (15)	C8—C7—N1—N2	−0.07 (16)
C7—C8—C9—N2	−0.88 (17)	C4—C7—N1—N2	177.71 (13)
C7—C8—C9—C12	177.53 (16)	C7—N1—N2—C9	−0.52 (16)
N2—C10—C11—O2	−4.4 (3)	C7—N1—N2—C10	179.84 (13)
N2—C10—C11—O1	175.55 (15)	C8—C9—N2—N1	0.90 (17)
N2—C9—C12—O3	0.9 (2)	C12—C9—N2—N1	−177.69 (13)
C8—C9—C12—O3	−177.26 (17)	C8—C9—N2—C10	−179.51 (15)
N2—C9—C12—N3	−179.91 (14)	C12—C9—N2—C10	1.9 (2)
C8—C9—C12—N3	1.9 (3)	C11—C10—N2—N1	103.82 (16)
N3—C13—C14—C19	−11.6 (2)	C11—C10—N2—C9	−75.7 (2)
N3—C13—C14—C15	168.96 (16)	O3—C12—N3—C13	−3.4 (3)
C19—C14—C15—C16	−2.0 (3)	C9—C12—N3—C13	177.51 (14)
C13—C14—C15—C16	177.5 (2)	C14—C13—N3—C12	85.7 (2)
C14—C15—C16—C17	−0.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O3^i	0.86	2.04	2.8027 (17)	148
O1—H1A···N1^ii	0.82	1.95	2.7493 (18)	165

Symmetry codes: (i) −y+3/4, x+1/4, z+1/4; (ii) −y+3/4, x−1/4, −z−1/4.