1,3-Bis(5-methyl-3-phenyl­pyrazol-1-yl)propan-2-ol

Mol­ecules of the title compound, C₂₃H₂₄N₄O, are linked into chains by O—H...N hydrogen bonds and C—H...π inter­actions. Aromatic π–π stacking inter­actions exist between chains.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.058
• wR factor = 0.172
• Data-to-parameter ratio = 8.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N2     -   C9      ..       7.18 su

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C5
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C19
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.49
           From the CIF: _reflns_number_total               2162
           Count of symmetry unique reflns         2163
           Completeness (_total/calc)             99.95%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12    = .          S

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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

---

Computing details

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

1,3-Bis(5-methyl-3-phenylpyrazol-1-yl)propan-2-ol

Crystal data

C23H24N4O	F(000) = 792
Mr = 372.46	Dx = 1.212 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1717 reflections
a = 9.8322 (19) Å	θ = 2.4–18.4°
b = 12.109 (2) Å	µ = 0.08 mm^−1
c = 17.141 (3) Å	T = 293 K
V = 2040.8 (6) Å^3	Block, yellow
Z = 4	0.38 × 0.16 × 0.07 mm

Data collection

Bruker SMART CCD diffractometer	2162 independent reflections
Radiation source: fine-focus sealed tube	1437 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
φ and ω scans	θmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→10
Tmin = 0.972, Tmax = 0.995	k = −14→14
13935 measured reflections	l = −20→20

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.172	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.1034P)^2] where P = (Fo^2 + 2Fc^2)/3
2162 reflections	(Δ/σ)max < 0.001
259 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

Experimental. Elemental analysis Calculated for C₂₃H₂₄N₄O: C 74.17, H 6.49, N 15.04% Found: C 73.91, H 6.18, N 14.86%. Spectroscopic analysis IR (KBr, ν cm^-1):3175, 3020, 1605, 1511, 1552, 1445, 759, 692. ¹HNMR (300 MHz, CDCl₃, δ, p.p.m.): 2.18 (s, 6H), 4.0–4.2 (m, 4H), 4.4(m, 1H), 5.4(s, 1H), 6.2(s, 2H, 7.2(m, 2H), 7.3(m, 4H), 7.6(m,4H)

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
O1	0.3713 (3)	0.2388 (3)	0.5456 (2)	0.0700 (9)
H1	0.413 (6)	0.174 (5)	0.548 (4)	0.12 (2)*
N1	0.3302 (4)	0.0723 (3)	0.3900 (2)	0.0612 (10)
N2	0.2493 (4)	0.0614 (3)	0.4521 (2)	0.0611 (10)
N3	0.0807 (3)	0.4164 (3)	0.47870 (18)	0.0477 (8)
N4	0.1628 (3)	0.4025 (3)	0.54120 (19)	0.0503 (8)
C1	0.4699 (4)	−0.0489 (3)	0.3101 (2)	0.0529 (10)
C2	0.5060 (6)	0.0341 (4)	0.2584 (3)	0.0748 (14)
H2A	0.4719	0.1050	0.2657	0.090*
C3	0.5914 (6)	0.0136 (6)	0.1964 (3)	0.0891 (17)
H3A	0.6142	0.0715	0.1632	0.107*
C4	0.6426 (6)	−0.0863 (6)	0.1822 (4)	0.0914 (18)
H4A	0.6993	−0.0985	0.1396	0.110*
C5	0.6097 (6)	−0.1699 (5)	0.2317 (4)	0.111 (2)
H5A	0.6446	−0.2401	0.2227	0.133*
C6	0.5259 (6)	−0.1527 (4)	0.2949 (4)	0.0913 (18)
H6A	0.5062	−0.2113	0.3281	0.110*
C7	0.3786 (4)	−0.0298 (4)	0.3768 (2)	0.0565 (11)
C8	0.3290 (5)	−0.1046 (4)	0.4304 (3)	0.0677 (13)
H8A	0.3480	−0.1797	0.4334	0.081*
C9	0.2450 (5)	−0.0438 (5)	0.4785 (3)	0.0724 (14)
C10	0.1584 (7)	−0.0814 (5)	0.5458 (3)	0.101 (2)
H10A	0.1809	−0.0393	0.5914	0.152*
H10B	0.1747	−0.1583	0.5556	0.152*
H10C	0.0642	−0.0706	0.5332	0.152*
C11	0.1774 (5)	0.1587 (4)	0.4818 (3)	0.0728 (14)
H11A	0.0836	0.1387	0.4923	0.087*
H11B	0.1771	0.2152	0.4417	0.087*
C12	0.2372 (4)	0.2047 (4)	0.5530 (3)	0.0636 (12)
H12A	0.2361	0.1459	0.5923	0.076*
C13	0.1556 (5)	0.3002 (3)	0.5863 (3)	0.0598 (12)
H13A	0.0611	0.2778	0.5901	0.072*
H13B	0.1876	0.3151	0.6388	0.072*
C14	0.2452 (5)	0.4899 (4)	0.5536 (3)	0.0562 (11)
C15	0.2147 (5)	0.5655 (4)	0.4972 (2)	0.0598 (12)
H15A	0.2538	0.6347	0.4905	0.072*
C16	0.1118 (4)	0.5170 (3)	0.4512 (2)	0.0513 (10)
C17	0.0439 (5)	0.5606 (4)	0.3814 (2)	0.0587 (11)
C18	0.0509 (7)	0.6728 (5)	0.3645 (3)	0.0935 (18)
H18A	0.0980	0.7201	0.3977	0.112*
C19	−0.0123 (8)	0.7145 (5)	0.2982 (4)	0.115 (2)
H19A	−0.0065	0.7894	0.2867	0.138*
C20	−0.0837 (7)	0.6446 (6)	0.2492 (3)	0.103 (2)
H20A	−0.1243	0.6723	0.2042	0.124*
C21	−0.0947 (6)	0.5349 (6)	0.2667 (3)	0.0886 (18)
H21A	−0.1454	0.4884	0.2348	0.106*
C22	−0.0298 (5)	0.4931 (5)	0.3324 (3)	0.0706 (13)
H22A	−0.0362	0.4181	0.3434	0.085*
C23	0.3464 (5)	0.4951 (5)	0.6195 (3)	0.0762 (14)
H23A	0.3958	0.4268	0.6221	0.114*
H23B	0.2993	0.5071	0.6678	0.114*
H23C	0.4087	0.5548	0.6105	0.114*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0468 (19)	0.0628 (19)	0.100 (2)	0.0060 (16)	0.0007 (18)	−0.0165 (19)
N1	0.053 (2)	0.066 (2)	0.064 (2)	0.0069 (19)	−0.002 (2)	−0.0177 (18)
N2	0.050 (2)	0.059 (2)	0.075 (2)	0.0015 (18)	−0.002 (2)	−0.013 (2)
N3	0.0416 (18)	0.0487 (19)	0.0527 (19)	0.0002 (16)	0.0028 (16)	−0.0075 (15)
N4	0.047 (2)	0.0542 (18)	0.0501 (18)	0.0045 (17)	0.0017 (18)	−0.0094 (16)
C1	0.045 (2)	0.054 (2)	0.059 (2)	−0.001 (2)	−0.003 (2)	−0.016 (2)
C2	0.077 (4)	0.072 (3)	0.075 (3)	0.014 (3)	−0.001 (3)	0.000 (3)
C3	0.085 (4)	0.122 (5)	0.061 (3)	−0.004 (4)	0.002 (3)	0.010 (3)
C4	0.077 (4)	0.099 (4)	0.098 (4)	−0.019 (4)	0.028 (3)	−0.032 (4)
C5	0.107 (5)	0.067 (3)	0.158 (6)	−0.006 (3)	0.068 (5)	−0.037 (4)
C6	0.093 (4)	0.050 (3)	0.131 (5)	−0.001 (3)	0.044 (4)	−0.005 (3)
C7	0.051 (3)	0.060 (3)	0.059 (2)	0.002 (2)	−0.006 (2)	−0.010 (2)
C8	0.062 (3)	0.062 (3)	0.079 (3)	−0.010 (3)	0.006 (3)	−0.016 (2)
C9	0.053 (3)	0.093 (4)	0.071 (3)	−0.011 (3)	0.014 (3)	−0.012 (3)
C10	0.100 (5)	0.106 (4)	0.097 (4)	−0.029 (4)	0.034 (4)	−0.018 (4)
C11	0.055 (3)	0.088 (3)	0.076 (3)	0.015 (3)	0.003 (3)	−0.015 (3)
C12	0.046 (3)	0.057 (2)	0.088 (3)	0.000 (2)	0.002 (3)	−0.008 (2)
C13	0.053 (3)	0.060 (3)	0.067 (3)	0.010 (2)	0.013 (2)	0.003 (2)
C14	0.050 (2)	0.058 (2)	0.061 (3)	−0.004 (2)	−0.003 (2)	−0.014 (2)
C15	0.059 (3)	0.059 (3)	0.061 (3)	−0.010 (2)	−0.006 (2)	−0.004 (2)
C16	0.047 (2)	0.056 (2)	0.051 (2)	0.004 (2)	0.002 (2)	−0.012 (2)
C17	0.056 (3)	0.063 (3)	0.058 (2)	0.004 (2)	0.003 (2)	−0.005 (2)
C18	0.129 (5)	0.074 (3)	0.078 (3)	0.000 (4)	−0.028 (4)	0.002 (3)
C19	0.172 (7)	0.076 (4)	0.098 (4)	0.046 (4)	−0.033 (5)	0.005 (3)
C20	0.117 (5)	0.121 (5)	0.072 (3)	0.043 (5)	−0.011 (4)	0.001 (4)
C21	0.067 (4)	0.131 (6)	0.068 (3)	0.012 (4)	−0.010 (3)	−0.010 (3)
C22	0.057 (3)	0.094 (4)	0.060 (3)	−0.001 (3)	−0.001 (2)	−0.006 (3)
C23	0.069 (3)	0.089 (3)	0.071 (3)	−0.007 (3)	−0.018 (3)	−0.009 (3)

Geometric parameters (Å, º)

O1—C12	1.387 (5)	C10—H10C	0.960
O1—H1	0.89 (6)	C11—C12	1.465 (7)
N1—N2	1.336 (5)	C11—H11A	0.970
N1—C7	1.344 (5)	C11—H11B	0.970
N2—C9	1.352 (6)	C12—C13	1.519 (6)
N2—C11	1.465 (6)	C12—H12A	0.980
N3—C16	1.341 (5)	C13—H13A	0.970
N3—N4	1.352 (4)	C13—H13B	0.970
N4—C14	1.349 (5)	C14—C15	1.364 (6)
N4—C13	1.462 (5)	C14—C23	1.506 (6)
C1—C2	1.386 (7)	C15—C16	1.410 (6)
C1—C6	1.397 (6)	C15—H15A	0.930
C1—C7	1.471 (6)	C16—C17	1.468 (6)
C2—C3	1.378 (7)	C17—C22	1.379 (6)
C2—H2A	0.930	C17—C18	1.391 (7)
C3—C4	1.333 (8)	C18—C19	1.391 (7)
C3—H3A	0.930	C18—H18A	0.930
C4—C5	1.360 (8)	C19—C20	1.384 (8)
C4—H4A	0.930	C19—H19A	0.930
C5—C6	1.378 (7)	C20—C21	1.365 (8)
C5—H5A	0.930	C20—H20A	0.930
C6—H6A	0.930	C21—C22	1.389 (7)
C7—C8	1.379 (6)	C21—H21A	0.930
C8—C9	1.380 (6)	C22—H22A	0.930
C8—H8A	0.930	C23—H23A	0.960
C9—C10	1.504 (7)	C23—H23B	0.960
C10—H10A	0.960	C23—H23C	0.960
C10—H10B	0.960
C12—O1—H1	100 (4)	H11A—C11—H11B	107.7
N2—N1—C7	104.8 (4)	O1—C12—C11	114.7 (4)
N1—N2—C9	112.2 (3)	O1—C12—C13	108.1 (4)
N1—N2—C11	119.0 (4)	C11—C12—C13	113.0 (4)
C9—N2—C11	128.8 (4)	O1—C12—H12A	106.9
C16—N3—N4	104.8 (3)	C11—C12—H12A	106.9
C14—N4—N3	112.7 (3)	C13—C12—H12A	106.9
C14—N4—C13	127.6 (4)	N4—C13—C12	114.9 (3)
N3—N4—C13	119.7 (3)	N4—C13—H13A	108.6
C2—C1—C6	115.6 (4)	C12—C13—H13A	108.6
C2—C1—C7	122.6 (4)	N4—C13—H13B	108.6
C6—C1—C7	121.8 (4)	C12—C13—H13B	108.6
C3—C2—C1	121.3 (5)	H13A—C13—H13B	107.5
C3—C2—H2A	119.4	N4—C14—C15	106.4 (4)
C1—C2—H2A	119.4	N4—C14—C23	123.2 (4)
C4—C3—C2	122.3 (6)	C15—C14—C23	130.4 (4)
C4—C3—H3A	118.8	C14—C15—C16	106.0 (4)
C2—C3—H3A	118.8	C14—C15—H15A	127.0
C3—C4—C5	118.2 (5)	C16—C15—H15A	127.0
C3—C4—H4A	120.9	N3—C16—C15	110.1 (4)
C5—C4—H4A	120.9	N3—C16—C17	120.6 (4)
C4—C5—C6	121.4 (5)	C15—C16—C17	129.2 (4)
C4—C5—H5A	119.3	C22—C17—C18	118.6 (5)
C6—C5—H5A	119.3	C22—C17—C16	121.5 (4)
C5—C6—C1	121.2 (5)	C18—C17—C16	119.9 (4)
C5—C6—H6A	119.4	C17—C18—C19	120.1 (6)
C1—C6—H6A	119.4	C17—C18—H18A	119.9
N1—C7—C8	111.4 (4)	C19—C18—H18A	119.9
N1—C7—C1	119.4 (4)	C20—C19—C18	120.1 (6)
C8—C7—C1	129.1 (4)	C20—C19—H19A	120.0
C7—C8—C9	105.1 (4)	C18—C19—H19A	120.0
C7—C8—H8A	127.4	C21—C20—C19	120.1 (6)
C9—C8—H8A	127.4	C21—C20—H20A	120.0
N2—C9—C8	106.5 (4)	C19—C20—H20A	120.0
N2—C9—C10	124.0 (5)	C20—C21—C22	119.8 (6)
C8—C9—C10	129.5 (5)	C20—C21—H21A	120.1
C9—C10—H10A	109.5	C22—C21—H21A	120.1
C9—C10—H10B	109.5	C17—C22—C21	121.2 (5)
H10A—C10—H10B	109.5	C17—C22—H22A	119.4
C9—C10—H10C	109.5	C21—C22—H22A	119.4
H10A—C10—H10C	109.5	C14—C23—H23A	109.5
H10B—C10—H10C	109.5	C14—C23—H23B	109.5
N2—C11—C12	113.7 (4)	H23A—C23—H23B	109.5
N2—C11—H11A	108.8	C14—C23—H23C	109.5
C12—C11—H11A	108.8	H23A—C23—H23C	109.5
N2—C11—H11B	108.8	H23B—C23—H23C	109.5
C12—C11—H11B	108.8
C7—N1—N2—C9	0.0 (5)	N2—C11—C12—O1	59.7 (6)
C7—N1—N2—C11	−179.1 (4)	N2—C11—C12—C13	−175.8 (4)
C16—N3—N4—C14	−0.6 (4)	C14—N4—C13—C12	−96.6 (5)
C16—N3—N4—C13	179.7 (3)	N3—N4—C13—C12	83.0 (5)
C6—C1—C2—C3	0.2 (8)	O1—C12—C13—N4	56.4 (5)
C7—C1—C2—C3	−179.8 (4)	C11—C12—C13—N4	−71.6 (5)
C1—C2—C3—C4	0.7 (9)	N3—N4—C14—C15	0.8 (5)
C2—C3—C4—C5	−0.8 (9)	C13—N4—C14—C15	−179.6 (4)
C3—C4—C5—C6	0.0 (10)	N3—N4—C14—C23	−179.9 (4)
C4—C5—C6—C1	0.8 (9)	C13—N4—C14—C23	−0.3 (6)
C2—C1—C6—C5	−0.9 (8)	N4—C14—C15—C16	−0.6 (5)
C7—C1—C6—C5	179.1 (5)	C23—C14—C15—C16	−179.8 (4)
N2—N1—C7—C8	−0.2 (5)	N4—N3—C16—C15	0.2 (4)
N2—N1—C7—C1	178.4 (3)	N4—N3—C16—C17	178.8 (3)
C2—C1—C7—N1	−1.7 (6)	C14—C15—C16—N3	0.2 (5)
C6—C1—C7—N1	178.3 (5)	C14—C15—C16—C17	−178.2 (4)
C2—C1—C7—C8	176.6 (5)	N3—C16—C17—C22	−14.5 (6)
C6—C1—C7—C8	−3.4 (7)	C15—C16—C17—C22	163.7 (4)
N1—C7—C8—C9	0.3 (5)	N3—C16—C17—C18	164.2 (5)
C1—C7—C8—C9	−178.1 (4)	C15—C16—C17—C18	−17.5 (7)
N1—N2—C9—C8	0.2 (5)	C22—C17—C18—C19	−1.8 (9)
C11—N2—C9—C8	179.2 (4)	C16—C17—C18—C19	179.5 (5)
N1—N2—C9—C10	−177.6 (5)	C17—C18—C19—C20	0.7 (11)
C11—N2—C9—C10	1.3 (8)	C18—C19—C20—C21	1.3 (11)
C7—C8—C9—N2	−0.3 (5)	C19—C20—C21—C22	−2.3 (10)
C7—C8—C9—C10	177.4 (5)	C18—C17—C22—C21	0.8 (7)
N1—N2—C11—C12	−103.9 (5)	C16—C17—C22—C21	179.5 (4)
C9—N2—C11—C12	77.2 (6)	C20—C21—C22—C17	1.3 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3^i	0.89 (6)	2.03 (7)	2.819 (5)	147 (6)
C10—H10A···Cg2^i	0.96	3.43	3.959	117
C23—H23B···Cg1^ii	0.96	2.90	3.768	151

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