Two isostructural 3-(5-ar­yloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(thio­phen-2-yl)prop-2-en-1-ones: disorder and supra­molecular assembly

In each of two isostructural 3-(5-ar­yloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(thio­phen-2-yl)prop-2-en-1-ones, the thio­phene unit is disordered over two sets of atomic sites and a combination of C—H...N and C—H...O hydrogen bonds link the mol­ecules into sheets.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.042
• wR factor = 0.117
• Data-to-parameter ratio = 13.9

Structure: II

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.045
• wR factor = 0.142
• Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -3.108 Report
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         10 Note
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          5 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          1 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        18% Note
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         10 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          7 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          5 Info

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: II


Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H25      ..N32      .       2.69 Ang.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -7.301 Report
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.457 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         10 Note
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          5 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          1 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        17% Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         10 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 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
   2 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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

For both structures, data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2017); data reduction: SAINT (Bruker, 2017); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2009).

3-(3-Methyl-5-phenoxy-1-phenyl-1H-pyrazol-4-yl)-1-(thiophen-2-yl)prop-2-en-1-one (I)

Crystal data

C23H18N2O2S	F(000) = 808
Mr = 386.45	Dx = 1.296 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.6158 (5) Å	Cell parameters from 3725 reflections
b = 19.8846 (11) Å	θ = 2.1–25.6°
c = 10.3773 (6) Å	µ = 0.18 mm^−1
β = 93.712 (2)°	T = 296 K
V = 1980.04 (19) Å^3	Block, colourless
Z = 4	0.20 × 0.20 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	3725 independent reflections
Radiation source: fine-focus sealed tube	2446 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
Detector resolution: 7.3910 pixels mm^-1	θmax = 25.6°, θmin = 2.1°
φ and ω scans	h = −10→11
Absorption correction: multi-scan (SADABS; Bruker, 2012)	k = −24→24
Tmin = 0.941, Tmax = 0.973	l = −12→12
31970 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.042	w = 1/[σ^2(Fo^2) + (0.0467P)^2 + 0.573P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.117	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.20 e Å^−3
3725 reflections	Δρmin = −0.14 e Å^−3
268 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
10 restraints	Extinction coefficient: 0.0059 (9)
Primary atom site location: difference Fourier map

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	Occ. (<1)
C1	0.6952 (2)	0.38677 (11)	0.5021 (2)	0.0485 (5)
O1	0.76942 (19)	0.43097 (8)	0.55125 (17)	0.0798 (6)
C2	0.5895 (2)	0.40140 (11)	0.3982 (2)	0.0480 (5)
H2	0.5376	0.3663	0.3604	0.058*
C3	0.5660 (2)	0.46399 (10)	0.35662 (19)	0.0451 (5)
H3	0.6175	0.4976	0.4000	0.054*
S11	0.82626 (11)	0.29817 (5)	0.67269 (8)	0.0664 (3)	0.844 (3)
C12	0.7111 (2)	0.31696 (10)	0.5460 (2)	0.0484 (5)	0.844 (3)
C13	0.6491 (14)	0.2615 (5)	0.5017 (13)	0.0930 (17)	0.844 (3)
H13	0.5837	0.2612	0.4316	0.112*	0.844 (3)
C14	0.6904 (13)	0.2030 (2)	0.5695 (15)	0.106 (3)	0.844 (3)
H14	0.6547	0.1605	0.5506	0.128*	0.844 (3)
C15	0.7865 (9)	0.2158 (3)	0.6639 (9)	0.080 (2)	0.844 (3)
H15	0.8270	0.1831	0.7185	0.096*	0.844 (3)
S21	0.614 (2)	0.2534 (7)	0.484 (2)	0.0930 (17)	0.156 (3)
C22	0.7111 (2)	0.31696 (10)	0.5460 (2)	0.0484 (5)	0.156 (3)
C23	0.813 (2)	0.2935 (10)	0.626 (2)	0.0664 (3)	0.156 (3)
H23	0.8837	0.3205	0.6635	0.080*	0.156 (3)
C24	0.805 (6)	0.2239 (12)	0.647 (6)	0.080 (2)	0.156 (3)
H24	0.8581	0.2009	0.7111	0.096*	0.156 (3)
C25	0.713 (8)	0.1950 (8)	0.564 (9)	0.106 (3)	0.156 (3)
H25	0.7042	0.1488	0.5511	0.128*	0.156 (3)
N31	0.31385 (16)	0.49026 (8)	0.08717 (15)	0.0417 (4)
N32	0.36763 (17)	0.55440 (8)	0.09923 (17)	0.0474 (4)
C33	0.4603 (2)	0.55130 (10)	0.1990 (2)	0.0444 (5)
C34	0.4706 (2)	0.48590 (10)	0.25279 (19)	0.0412 (5)
C35	0.3759 (2)	0.44920 (9)	0.17696 (18)	0.0397 (5)
C311	0.2118 (2)	0.47606 (10)	−0.01477 (19)	0.0400 (5)
C312	0.1122 (2)	0.42704 (10)	−0.0019 (2)	0.0480 (5)
H312	0.1113	0.4020	0.0737	0.058*
C313	0.0143 (2)	0.41552 (11)	−0.1021 (2)	0.0555 (6)
H313	−0.0532	0.3826	−0.0937	0.067*
C314	0.0151 (2)	0.45223 (12)	−0.2146 (2)	0.0609 (7)
H314	−0.0508	0.4439	−0.2822	0.073*
C315	0.1141 (3)	0.50138 (13)	−0.2260 (2)	0.0596 (6)
H315	0.1146	0.5266	−0.3015	0.071*
C316	0.2127 (2)	0.51353 (11)	−0.1264 (2)	0.0499 (5)
H316	0.2794	0.5468	−0.1345	0.060*
C331	0.5426 (2)	0.61231 (11)	0.2386 (2)	0.0609 (6)
H31A	0.6353	0.6082	0.2102	0.091*
H31B	0.5468	0.6165	0.3309	0.091*
H31C	0.4987	0.6514	0.2001	0.091*
O35	0.35064 (14)	0.38210 (6)	0.17345 (13)	0.0458 (4)
C351	0.2722 (2)	0.35338 (10)	0.2680 (2)	0.0445 (5)
C352	0.2634 (3)	0.28476 (12)	0.2623 (3)	0.0687 (7)
H352	0.3095	0.2609	0.2009	0.082*
C353	0.1856 (3)	0.25194 (15)	0.3483 (4)	0.0947 (10)
H353	0.1786	0.2053	0.3453	0.114*
C354	0.1183 (3)	0.28709 (17)	0.4383 (4)	0.0972 (11)
H354	0.0656	0.2644	0.4965	0.117*
C355	0.1281 (3)	0.35565 (16)	0.4432 (3)	0.0854 (9)
H355	0.0820	0.3793	0.5049	0.102*
C356	0.2065 (2)	0.39028 (12)	0.3568 (2)	0.0603 (6)
H356	0.2138	0.4369	0.3594	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0522 (13)	0.0469 (13)	0.0450 (12)	−0.0042 (10)	−0.0060 (10)	0.0003 (10)
O1	0.0919 (13)	0.0535 (10)	0.0872 (13)	−0.0176 (9)	−0.0475 (10)	0.0094 (9)
C2	0.0493 (12)	0.0441 (12)	0.0491 (12)	−0.0035 (10)	−0.0085 (10)	−0.0002 (10)
C3	0.0465 (12)	0.0443 (12)	0.0437 (12)	−0.0051 (9)	−0.0022 (10)	−0.0015 (9)
S11	0.0811 (6)	0.0537 (5)	0.0608 (6)	−0.0027 (4)	−0.0243 (5)	0.0092 (4)
C12	0.0550 (13)	0.0451 (13)	0.0442 (12)	0.0012 (10)	−0.0038 (10)	−0.0002 (10)
C13	0.138 (7)	0.048 (2)	0.086 (4)	−0.017 (2)	−0.050 (3)	−0.004 (2)
C14	0.167 (6)	0.0398 (17)	0.104 (3)	−0.009 (3)	−0.050 (5)	0.002 (3)
C15	0.113 (4)	0.055 (2)	0.070 (4)	0.007 (2)	−0.016 (3)	0.0186 (17)
S21	0.138 (7)	0.048 (2)	0.086 (4)	−0.017 (2)	−0.050 (3)	−0.004 (2)
C22	0.0550 (13)	0.0451 (13)	0.0442 (12)	0.0012 (10)	−0.0038 (10)	−0.0002 (10)
C23	0.0811 (6)	0.0537 (5)	0.0608 (6)	−0.0027 (4)	−0.0243 (5)	0.0092 (4)
C24	0.113 (4)	0.055 (2)	0.070 (4)	0.007 (2)	−0.016 (3)	0.0186 (17)
C25	0.167 (6)	0.0398 (17)	0.104 (3)	−0.009 (3)	−0.050 (5)	0.002 (3)
N31	0.0402 (9)	0.0369 (9)	0.0473 (10)	0.0007 (7)	−0.0034 (8)	0.0033 (8)
N32	0.0489 (10)	0.0350 (10)	0.0571 (11)	−0.0031 (8)	−0.0054 (9)	0.0051 (8)
C33	0.0428 (11)	0.0390 (12)	0.0509 (13)	−0.0024 (9)	−0.0002 (10)	0.0011 (10)
C34	0.0393 (11)	0.0401 (11)	0.0437 (11)	−0.0002 (9)	−0.0002 (9)	0.0016 (9)
C35	0.0393 (11)	0.0345 (11)	0.0450 (11)	0.0012 (9)	0.0016 (9)	0.0022 (9)
C311	0.0372 (11)	0.0397 (11)	0.0425 (11)	0.0050 (9)	−0.0028 (9)	−0.0025 (9)
C312	0.0471 (12)	0.0425 (12)	0.0534 (13)	0.0040 (10)	−0.0045 (10)	−0.0020 (10)
C313	0.0485 (13)	0.0508 (14)	0.0655 (15)	0.0010 (11)	−0.0082 (11)	−0.0108 (12)
C314	0.0554 (14)	0.0677 (16)	0.0570 (15)	0.0127 (13)	−0.0149 (11)	−0.0184 (13)
C315	0.0631 (15)	0.0706 (16)	0.0441 (13)	0.0090 (13)	−0.0037 (12)	0.0026 (11)
C316	0.0473 (12)	0.0552 (14)	0.0470 (13)	0.0025 (10)	0.0016 (10)	0.0025 (10)
C331	0.0622 (15)	0.0451 (13)	0.0738 (16)	−0.0077 (11)	−0.0082 (12)	0.0016 (12)
O35	0.0525 (9)	0.0332 (8)	0.0515 (9)	−0.0010 (6)	0.0036 (7)	0.0004 (6)
C351	0.0411 (11)	0.0398 (12)	0.0515 (13)	−0.0025 (9)	−0.0047 (10)	0.0105 (10)
C352	0.0714 (16)	0.0420 (14)	0.093 (2)	−0.0053 (12)	0.0095 (15)	0.0076 (13)
C353	0.094 (2)	0.0543 (17)	0.138 (3)	−0.0114 (16)	0.023 (2)	0.0266 (19)
C354	0.093 (2)	0.087 (2)	0.115 (3)	−0.0112 (18)	0.027 (2)	0.046 (2)
C355	0.086 (2)	0.095 (2)	0.0777 (19)	−0.0017 (17)	0.0287 (16)	0.0142 (17)
C356	0.0628 (15)	0.0546 (14)	0.0640 (15)	−0.0025 (12)	0.0093 (12)	0.0034 (12)

Geometric parameters (Å, º)

C1—O1	1.223 (2)	C35—O35	1.356 (2)
C1—C2	1.462 (3)	C311—C316	1.378 (3)
C1—C12	1.466 (3)	C311—C312	1.379 (3)
C2—C3	1.332 (3)	C312—C313	1.376 (3)
C2—H2	0.9300	C312—H312	0.9300
C3—C34	1.437 (3)	C313—C314	1.377 (3)
C3—H3	0.9300	C313—H313	0.9300
S11—C15	1.684 (5)	C314—C315	1.375 (3)
S11—C12	1.705 (2)	C314—H314	0.9300
C12—C13	1.322 (7)	C315—C316	1.378 (3)
C13—C14	1.402 (10)	C315—H315	0.9300
C13—H13	0.9300	C316—H316	0.9300
C14—C15	1.327 (5)	C331—H31A	0.9600
C14—H14	0.9300	C331—H31B	0.9600
C15—H15	0.9300	C331—H31C	0.9600
S21—C25	1.685 (12)	O35—C351	1.398 (2)
C23—C24	1.404 (14)	C351—C356	1.365 (3)
C23—H23	0.9300	C351—C352	1.368 (3)
C24—C25	1.329 (9)	C352—C353	1.366 (4)
C24—H24	0.9300	C352—H352	0.9300
C25—H25	0.9300	C353—C354	1.364 (4)
N31—C35	1.349 (2)	C353—H353	0.9300
N31—N32	1.379 (2)	C354—C355	1.367 (4)
N31—C311	1.424 (2)	C354—H354	0.9300
N32—C33	1.323 (3)	C355—C356	1.391 (3)
C33—C34	1.416 (3)	C355—H355	0.9300
C33—C331	1.492 (3)	C356—H356	0.9300
C34—C35	1.374 (3)
O1—C1—C2	121.57 (19)	C316—C311—N31	118.45 (18)
O1—C1—C12	120.34 (19)	C312—C311—N31	121.18 (18)
C2—C1—C12	118.09 (18)	C313—C312—C311	119.4 (2)
C3—C2—C1	121.35 (19)	C313—C312—H312	120.3
C3—C2—H2	119.3	C311—C312—H312	120.3
C1—C2—H2	119.3	C312—C313—C314	120.7 (2)
C2—C3—C34	127.83 (19)	C312—C313—H313	119.6
C2—C3—H3	116.1	C314—C313—H313	119.6
C34—C3—H3	116.1	C315—C314—C313	119.5 (2)
C15—S11—C12	92.15 (19)	C315—C314—H314	120.3
C13—C12—C1	130.3 (5)	C313—C314—H314	120.3
C13—C12—S11	110.0 (5)	C314—C315—C316	120.4 (2)
C1—C12—S11	119.77 (15)	C314—C315—H315	119.8
C12—C13—C14	114.2 (6)	C316—C315—H315	119.8
C12—C13—H13	122.9	C315—C316—C311	119.7 (2)
C14—C13—H13	122.9	C315—C316—H316	120.2
C15—C14—C13	111.9 (4)	C311—C316—H316	120.2
C15—C14—H14	124.0	C33—C331—H31A	109.5
C13—C14—H14	124.0	C33—C331—H31B	109.5
C14—C15—S11	111.7 (4)	H31A—C331—H31B	109.5
C14—C15—H15	124.1	C33—C331—H31C	109.5
S11—C15—H15	124.1	H31A—C331—H31C	109.5
C24—C23—H23	123.3	H31B—C331—H31C	109.5
C25—C24—C23	111.4 (14)	C35—O35—C351	119.13 (15)
C25—C24—H24	124.3	C356—C351—C352	122.3 (2)
C23—C24—H24	124.3	C356—C351—O35	123.30 (19)
C24—C25—S21	110.8 (12)	C352—C351—O35	114.3 (2)
C24—C25—H25	124.6	C353—C352—C351	118.9 (3)
S21—C25—H25	124.6	C353—C352—H352	120.5
C35—N31—N32	110.54 (15)	C351—C352—H352	120.5
C35—N31—C311	130.24 (16)	C354—C353—C352	120.4 (3)
N32—N31—C311	119.16 (15)	C354—C353—H353	119.8
C33—N32—N31	104.92 (15)	C352—C353—H353	119.8
N32—C33—C34	112.18 (17)	C353—C354—C355	120.1 (3)
N32—C33—C331	119.74 (18)	C353—C354—H354	119.9
C34—C33—C331	128.03 (19)	C355—C354—H354	119.9
C35—C34—C33	103.60 (17)	C354—C355—C356	120.6 (3)
C35—C34—C3	129.46 (18)	C354—C355—H355	119.7
C33—C34—C3	126.81 (18)	C356—C355—H355	119.7
N31—C35—O35	120.45 (17)	C351—C356—C355	117.6 (2)
N31—C35—C34	108.73 (17)	C351—C356—H356	121.2
O35—C35—C34	130.44 (17)	C355—C356—H356	121.2
C316—C311—C312	120.35 (19)
O1—C1—C2—C3	−2.8 (3)	C33—C34—C35—N31	−0.8 (2)
C12—C1—C2—C3	177.6 (2)	C3—C34—C35—N31	−176.83 (19)
C1—C2—C3—C34	177.2 (2)	C33—C34—C35—O35	172.0 (2)
O1—C1—C12—C13	−175.3 (10)	C3—C34—C35—O35	−4.1 (4)
C2—C1—C12—C13	4.3 (11)	C35—N31—C311—C316	−148.8 (2)
O1—C1—C12—S11	4.0 (3)	N32—N31—C311—C316	27.9 (3)
C2—C1—C12—S11	−176.40 (16)	C35—N31—C311—C312	32.6 (3)
C15—S11—C12—C13	−0.6 (9)	N32—N31—C311—C312	−150.69 (18)
C15—S11—C12—C1	180.0 (4)	C316—C311—C312—C313	0.5 (3)
C1—C12—C13—C14	−179.5 (10)	N31—C311—C312—C313	179.09 (18)
S11—C12—C13—C14	1.1 (17)	C311—C312—C313—C314	0.2 (3)
C12—C13—C14—C15	−1 (2)	C312—C313—C314—C315	−0.7 (3)
C13—C14—C15—S11	0.7 (17)	C313—C314—C315—C316	0.6 (3)
C12—S11—C15—C14	−0.1 (11)	C314—C315—C316—C311	0.1 (3)
C23—C24—C25—S21	−12 (9)	C312—C311—C316—C315	−0.6 (3)
C35—N31—N32—C33	−1.3 (2)	N31—C311—C316—C315	−179.25 (18)
C311—N31—N32—C33	−178.64 (17)	N31—C35—O35—C351	−109.5 (2)
N31—N32—C33—C34	0.8 (2)	C34—C35—O35—C351	78.5 (3)
N31—N32—C33—C331	178.55 (18)	C35—O35—C351—C356	7.1 (3)
N32—C33—C34—C35	0.0 (2)	C35—O35—C351—C352	−174.51 (18)
C331—C33—C34—C35	−177.6 (2)	C356—C351—C352—C353	0.2 (4)
N32—C33—C34—C3	176.16 (19)	O35—C351—C352—C353	−178.2 (2)
C331—C33—C34—C3	−1.4 (4)	C351—C352—C353—C354	−0.1 (5)
C2—C3—C34—C35	4.2 (4)	C352—C353—C354—C355	0.0 (5)
C2—C3—C34—C33	−171.0 (2)	C353—C354—C355—C356	0.0 (5)
N32—N31—C35—O35	−172.30 (16)	C352—C351—C356—C355	−0.2 (4)
C311—N31—C35—O35	4.7 (3)	O35—C351—C356—C355	178.1 (2)
N32—N31—C35—C34	1.3 (2)	C354—C355—C356—C351	0.0 (4)
C311—N31—C35—C34	178.29 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···N32^i	0.93	2.62	3.462 (9)	151
C25—H25···N32^i	0.93	2.51	3.33 (5)	148
C314—H314···O1^ii	0.93	2.38	3.305 (3)	175

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

3-[3-Methyl-5-(2-methylphenoxy)-1-phenyl-1H-pyrazol-4-yl]-1-(thiophen-2-yl)prop-2-en-1-one (II)

Crystal data

C24H20N2O2S	F(000) = 840
Mr = 400.48	Dx = 1.294 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.4336 (4) Å	Cell parameters from 5216 reflections
b = 20.6071 (9) Å	θ = 2.0–28.6°
c = 10.5866 (4) Å	µ = 0.18 mm^−1
β = 93.106 (2)°	T = 296 K
V = 2055.00 (15) Å^3	Block, colourless
Z = 4	0.30 × 0.20 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	4735 independent reflections
Radiation source: fine-focus sealed tube	2877 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
Detector resolution: 7.3910 pixels mm^-1	θmax = 27.6°, θmin = 2.0°
φ and ω scans	h = −12→11
Absorption correction: multi-scan (SADABS; Bruker, 2012)	k = −26→26
Tmin = 0.926, Tmax = 0.973	l = −13→11
35938 measured reflections

Refinement

Refinement on F^2	Primary 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) = 0.142	w = 1/[σ^2(Fo^2) + (0.0624P)^2 + 0.5761P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
4735 reflections	Δρmax = 0.19 e Å^−3
277 parameters	Δρmin = −0.23 e Å^−3
10 restraints

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	Occ. (<1)
C1	0.6834 (2)	0.38495 (10)	0.49061 (18)	0.0484 (5)
O1	0.75006 (19)	0.42752 (8)	0.54834 (16)	0.0747 (5)
C2	0.5798 (2)	0.39981 (10)	0.38620 (18)	0.0484 (5)
H2	0.5302	0.3661	0.3455	0.058*
C3	0.5555 (2)	0.46061 (10)	0.34871 (18)	0.0464 (5)
H3	0.6047	0.4926	0.3949	0.056*
S11	0.81442 (11)	0.29803 (4)	0.65506 (8)	0.0669 (3)	0.883 (2)
C12	0.7062 (2)	0.31666 (10)	0.52477 (17)	0.0456 (5)	0.883 (2)
C13	0.6609 (8)	0.2617 (3)	0.4682 (5)	0.0603 (9)	0.883 (2)
H13	0.6001	0.2616	0.3961	0.072*	0.883 (2)
C14	0.7118 (5)	0.20428 (17)	0.5259 (4)	0.0643 (12)	0.883 (2)
H14	0.6912	0.1627	0.4961	0.077*	0.883 (2)
C15	0.7941 (9)	0.21758 (17)	0.6295 (6)	0.0671 (16)	0.883 (2)
H15	0.8357	0.1859	0.6819	0.080*	0.883 (2)
S21	0.6339 (18)	0.2553 (6)	0.4380 (13)	0.0603 (9)	0.117 (2)
C22	0.7062 (2)	0.31666 (10)	0.52477 (17)	0.0456 (5)	0.117 (2)
C23	0.784 (3)	0.2933 (10)	0.623 (2)	0.0669 (3)	0.117 (2)
H23	0.8396	0.3195	0.6777	0.080*	0.117 (2)
C24	0.775 (8)	0.2255 (11)	0.638 (5)	0.0671 (16)	0.117 (2)
H24	0.8252	0.2018	0.7011	0.080*	0.117 (2)
C25	0.685 (5)	0.2001 (8)	0.550 (3)	0.0643 (12)	0.117 (2)
H25	0.6544	0.1573	0.5494	0.077*	0.117 (2)
N31	0.30777 (16)	0.48865 (7)	0.08120 (15)	0.0431 (4)
N32	0.36119 (18)	0.55036 (8)	0.09699 (16)	0.0492 (4)
C33	0.4529 (2)	0.54660 (9)	0.19571 (19)	0.0469 (5)
C34	0.4627 (2)	0.48304 (9)	0.24567 (18)	0.0430 (4)
C35	0.36867 (19)	0.44824 (9)	0.16871 (17)	0.0405 (4)
C311	0.20793 (19)	0.47603 (9)	−0.02174 (18)	0.0419 (4)
C312	0.1090 (2)	0.42664 (10)	−0.0158 (2)	0.0495 (5)
H312	0.1062	0.4009	0.0562	0.059*
C313	0.0145 (2)	0.41597 (11)	−0.1180 (2)	0.0580 (6)
H313	−0.0515	0.3826	−0.1147	0.070*
C314	0.0169 (2)	0.45393 (12)	−0.2241 (2)	0.0624 (6)
H314	−0.0469	0.4462	−0.2926	0.075*
C315	0.1140 (2)	0.50340 (13)	−0.2289 (2)	0.0621 (6)
H315	0.1154	0.5294	−0.3006	0.075*
C316	0.2098 (2)	0.51483 (11)	−0.12766 (19)	0.0506 (5)
H316	0.2751	0.5485	−0.1311	0.061*
C331	0.5357 (3)	0.60493 (10)	0.2386 (2)	0.0625 (6)
H31A	0.6318	0.6008	0.2142	0.094*
H31B	0.5349	0.6085	0.3290	0.094*
H31C	0.4936	0.6430	0.2003	0.094*
O35	0.34553 (14)	0.38351 (6)	0.16246 (12)	0.0470 (3)
C351	0.2552 (2)	0.35450 (10)	0.24627 (19)	0.0488 (5)
C352	0.2429 (2)	0.28766 (11)	0.2301 (2)	0.0614 (6)
C353	0.1516 (3)	0.25613 (15)	0.3056 (3)	0.0874 (10)
H353	0.1404	0.2114	0.2977	0.105*
C354	0.0766 (3)	0.28876 (19)	0.3921 (3)	0.0949 (11)
H354	0.0143	0.2661	0.4410	0.114*
C355	0.0918 (3)	0.35466 (17)	0.4081 (3)	0.0862 (9)
H355	0.0411	0.3763	0.4681	0.103*
C356	0.1842 (2)	0.38895 (13)	0.3332 (2)	0.0656 (6)
H356	0.1968	0.4335	0.3424	0.079*
C357	0.3278 (3)	0.25326 (12)	0.1355 (3)	0.0832 (9)
H35A	0.4265	0.2546	0.1625	0.125*
H35B	0.3141	0.2742	0.0547	0.125*
H35C	0.2971	0.2089	0.1285	0.125*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0519 (12)	0.0483 (12)	0.0442 (11)	−0.0032 (10)	−0.0045 (9)	0.0023 (9)
O1	0.0920 (12)	0.0541 (9)	0.0734 (10)	−0.0092 (9)	−0.0381 (9)	0.0023 (8)
C2	0.0481 (11)	0.0482 (12)	0.0476 (11)	−0.0023 (9)	−0.0087 (9)	0.0021 (9)
C3	0.0468 (11)	0.0481 (12)	0.0437 (11)	−0.0023 (9)	−0.0039 (9)	−0.0007 (9)
S11	0.0885 (6)	0.0555 (4)	0.0533 (5)	0.0004 (4)	−0.0283 (3)	0.0057 (3)
C12	0.0471 (11)	0.0492 (11)	0.0399 (10)	0.0002 (9)	−0.0036 (8)	0.0023 (9)
C13	0.071 (3)	0.0556 (17)	0.051 (3)	−0.0026 (16)	−0.0199 (18)	−0.0051 (17)
C14	0.079 (3)	0.0449 (13)	0.068 (2)	−0.0014 (13)	−0.004 (2)	−0.0002 (12)
C15	0.081 (3)	0.0560 (16)	0.0624 (19)	0.0084 (19)	−0.008 (2)	0.0112 (16)
S21	0.071 (3)	0.0556 (17)	0.051 (3)	−0.0026 (16)	−0.0199 (18)	−0.0051 (17)
C22	0.0471 (11)	0.0492 (11)	0.0399 (10)	0.0002 (9)	−0.0036 (8)	0.0023 (9)
C23	0.0885 (6)	0.0555 (4)	0.0533 (5)	0.0004 (4)	−0.0283 (3)	0.0057 (3)
C24	0.081 (3)	0.0560 (16)	0.0624 (19)	0.0084 (19)	−0.008 (2)	0.0112 (16)
C25	0.079 (3)	0.0449 (13)	0.068 (2)	−0.0014 (13)	−0.004 (2)	−0.0002 (12)
N31	0.0448 (9)	0.0350 (8)	0.0485 (9)	−0.0001 (7)	−0.0054 (7)	0.0033 (7)
N32	0.0528 (10)	0.0345 (9)	0.0591 (10)	−0.0033 (7)	−0.0083 (8)	0.0040 (8)
C33	0.0475 (11)	0.0377 (10)	0.0548 (12)	−0.0009 (9)	−0.0022 (9)	0.0005 (9)
C34	0.0422 (10)	0.0387 (10)	0.0477 (11)	0.0013 (8)	−0.0024 (8)	0.0012 (8)
C35	0.0413 (10)	0.0335 (10)	0.0467 (11)	0.0003 (8)	0.0008 (8)	0.0030 (8)
C311	0.0391 (10)	0.0402 (10)	0.0458 (11)	0.0067 (8)	−0.0027 (8)	−0.0022 (8)
C312	0.0479 (11)	0.0452 (11)	0.0546 (12)	0.0027 (9)	−0.0042 (9)	0.0008 (9)
C313	0.0506 (12)	0.0577 (13)	0.0643 (14)	0.0000 (11)	−0.0091 (10)	−0.0109 (11)
C314	0.0555 (13)	0.0760 (16)	0.0541 (14)	0.0087 (12)	−0.0130 (10)	−0.0127 (12)
C315	0.0601 (14)	0.0776 (16)	0.0479 (12)	0.0094 (12)	−0.0039 (10)	0.0072 (11)
C316	0.0470 (11)	0.0542 (13)	0.0505 (12)	0.0032 (10)	0.0008 (9)	0.0051 (10)
C331	0.0679 (15)	0.0413 (12)	0.0766 (15)	−0.0052 (10)	−0.0124 (12)	−0.0050 (11)
O35	0.0492 (8)	0.0340 (7)	0.0575 (8)	−0.0018 (6)	0.0006 (6)	0.0031 (6)
C351	0.0394 (10)	0.0485 (12)	0.0570 (12)	−0.0034 (9)	−0.0099 (9)	0.0174 (10)
C352	0.0555 (13)	0.0484 (13)	0.0770 (15)	−0.0111 (11)	−0.0283 (12)	0.0223 (12)
C353	0.0746 (18)	0.0729 (19)	0.111 (2)	−0.0286 (15)	−0.0290 (18)	0.0405 (18)
C354	0.0654 (18)	0.108 (3)	0.111 (3)	−0.0234 (18)	−0.0064 (17)	0.059 (2)
C355	0.0606 (16)	0.116 (3)	0.0831 (19)	0.0065 (16)	0.0130 (14)	0.0311 (18)
C356	0.0562 (14)	0.0687 (16)	0.0725 (15)	0.0046 (12)	0.0073 (12)	0.0193 (13)
C357	0.108 (2)	0.0412 (13)	0.097 (2)	−0.0010 (14)	−0.0277 (18)	−0.0037 (13)

Geometric parameters (Å, º)

C1—O1	1.223 (2)	C311—C316	1.378 (3)
C1—C12	1.466 (3)	C311—C312	1.385 (3)
C1—C2	1.468 (3)	C312—C313	1.382 (3)
C2—C3	1.330 (3)	C312—H312	0.9300
C2—H2	0.9300	C313—C314	1.371 (3)
C3—C34	1.437 (3)	C313—H313	0.9300
C3—H3	0.9300	C314—C315	1.373 (3)
S11—C15	1.689 (4)	C314—H314	0.9300
S11—C12	1.7146 (19)	C315—C316	1.384 (3)
C12—C13	1.340 (5)	C315—H315	0.9300
C13—C14	1.404 (6)	C316—H316	0.9300
C13—H13	0.9300	C331—H31A	0.9600
C14—C15	1.337 (3)	C331—H31B	0.9600
C14—H14	0.9300	C331—H31C	0.9600
C15—H15	0.9300	O35—C351	1.397 (2)
S21—C25	1.692 (11)	C351—C356	1.367 (3)
C23—C24	1.408 (11)	C351—C352	1.392 (3)
C23—H23	0.9300	C352—C353	1.370 (4)
C24—C25	1.340 (9)	C352—C357	1.495 (4)
C24—H24	0.9300	C353—C354	1.364 (5)
C25—H25	0.9300	C353—H353	0.9300
N31—C35	1.351 (2)	C354—C355	1.375 (4)
N31—N32	1.375 (2)	C354—H354	0.9300
N31—C311	1.425 (2)	C355—C356	1.400 (3)
N32—C33	1.322 (2)	C355—H355	0.9300
C33—C34	1.414 (3)	C356—H356	0.9300
C33—C331	1.491 (3)	C357—H35A	0.9600
C34—C35	1.373 (3)	C357—H35B	0.9600
C35—O35	1.353 (2)	C357—H35C	0.9600
O1—C1—C12	120.05 (18)	C313—C312—H312	120.4
O1—C1—C2	121.99 (19)	C311—C312—H312	120.4
C12—C1—C2	117.96 (17)	C314—C313—C312	120.9 (2)
C3—C2—C1	121.21 (18)	C314—C313—H313	119.6
C3—C2—H2	119.4	C312—C313—H313	119.6
C1—C2—H2	119.4	C313—C314—C315	119.6 (2)
C2—C3—C34	128.12 (19)	C313—C314—H314	120.2
C2—C3—H3	115.9	C315—C314—H314	120.2
C34—C3—H3	115.9	C314—C315—C316	120.4 (2)
C15—S11—C12	91.91 (14)	C314—C315—H315	119.8
C13—C12—C1	131.5 (3)	C316—C315—H315	119.8
C13—C12—S11	109.4 (3)	C311—C316—C315	119.7 (2)
C1—C12—S11	119.10 (15)	C311—C316—H316	120.2
C12—C13—C14	115.1 (3)	C315—C316—H316	120.2
C12—C13—H13	122.4	C33—C331—H31A	109.5
C14—C13—H13	122.4	C33—C331—H31B	109.5
C15—C14—C13	110.7 (3)	H31A—C331—H31B	109.5
C15—C14—H14	124.6	C33—C331—H31C	109.5
C13—C14—H14	124.6	H31A—C331—H31C	109.5
C14—C15—S11	112.9 (3)	H31B—C331—H31C	109.5
C14—C15—H15	123.6	C35—O35—C351	119.55 (16)
S11—C15—H15	123.6	C356—C351—C352	123.8 (2)
C24—C23—H23	122.8	C356—C351—O35	122.94 (19)
C25—C24—C23	110.3 (12)	C352—C351—O35	113.3 (2)
C25—C24—H24	124.9	C353—C352—C351	116.7 (3)
C23—C24—H24	124.9	C353—C352—C357	122.8 (3)
C24—C25—S21	112.0 (11)	C351—C352—C357	120.5 (2)
C24—C25—H25	124.0	C354—C353—C352	121.5 (3)
S21—C25—H25	124.0	C354—C353—H353	119.2
C35—N31—N32	110.33 (15)	C352—C353—H353	119.2
C35—N31—C311	130.62 (16)	C353—C354—C355	121.0 (3)
N32—N31—C311	118.98 (15)	C353—C354—H354	119.5
C33—N32—N31	105.17 (15)	C355—C354—H354	119.5
N32—C33—C34	112.14 (17)	C354—C355—C356	119.5 (3)
N32—C33—C331	120.20 (18)	C354—C355—H355	120.2
C34—C33—C331	127.61 (18)	C356—C355—H355	120.2
C35—C34—C33	103.57 (16)	C351—C356—C355	117.5 (3)
C35—C34—C3	129.00 (18)	C351—C356—H356	121.2
C33—C34—C3	127.36 (18)	C355—C356—H356	121.2
N31—C35—O35	120.86 (16)	C352—C357—H35A	109.5
N31—C35—C34	108.79 (16)	C352—C357—H35B	109.5
O35—C35—C34	129.88 (17)	H35A—C357—H35B	109.5
C316—C311—C312	120.13 (18)	C352—C357—H35C	109.5
C316—C311—N31	118.65 (18)	H35A—C357—H35C	109.5
C312—C311—N31	121.21 (17)	H35B—C357—H35C	109.5
C313—C312—C311	119.3 (2)
O1—C1—C2—C3	1.0 (3)	C3—C34—C35—N31	−177.55 (18)
C12—C1—C2—C3	−178.86 (19)	C33—C34—C35—O35	171.48 (19)
C1—C2—C3—C34	177.23 (19)	C3—C34—C35—O35	−5.6 (3)
O1—C1—C12—C13	−170.9 (5)	C35—N31—C311—C316	−150.6 (2)
C2—C1—C12—C13	9.0 (6)	N32—N31—C311—C316	25.9 (3)
O1—C1—C12—S11	6.0 (3)	C35—N31—C311—C312	30.5 (3)
C2—C1—C12—S11	−174.22 (15)	N32—N31—C311—C312	−153.05 (18)
C15—S11—C12—C13	−0.3 (5)	C316—C311—C312—C313	1.3 (3)
C15—S11—C12—C1	−177.8 (4)	N31—C311—C312—C313	−179.78 (18)
C1—C12—C13—C14	176.4 (4)	C311—C312—C313—C314	−0.6 (3)
S11—C12—C13—C14	−0.6 (7)	C312—C313—C314—C315	−0.3 (3)
C12—C13—C14—C15	1.6 (9)	C313—C314—C315—C316	0.4 (3)
C13—C14—C15—S11	−1.8 (9)	C312—C311—C316—C315	−1.2 (3)
C12—S11—C15—C14	1.3 (7)	N31—C311—C316—C315	179.88 (18)
C23—C24—C25—S21	9 (8)	C314—C315—C316—C311	0.3 (3)
C35—N31—N32—C33	−0.9 (2)	N31—C35—O35—C351	−105.1 (2)
C311—N31—N32—C33	−178.00 (16)	C34—C35—O35—C351	83.7 (2)
N31—N32—C33—C34	0.6 (2)	C35—O35—C351—C356	2.2 (3)
N31—N32—C33—C331	178.19 (19)	C35—O35—C351—C352	−179.18 (16)
N32—C33—C34—C35	0.0 (2)	C356—C351—C352—C353	1.2 (3)
C331—C33—C34—C35	−177.5 (2)	O35—C351—C352—C353	−177.45 (18)
N32—C33—C34—C3	177.07 (18)	C356—C351—C352—C357	−178.1 (2)
C331—C33—C34—C3	−0.4 (4)	O35—C351—C352—C357	3.3 (3)
C2—C3—C34—C35	6.2 (4)	C351—C352—C353—C354	0.0 (4)
C2—C3—C34—C33	−170.2 (2)	C357—C352—C353—C354	179.3 (2)
N32—N31—C35—O35	−171.96 (16)	C352—C353—C354—C355	−1.0 (4)
C311—N31—C35—O35	4.7 (3)	C353—C354—C355—C356	0.9 (4)
N32—N31—C35—C34	0.9 (2)	C352—C351—C356—C355	−1.3 (3)
C311—N31—C35—C34	177.56 (18)	O35—C351—C356—C355	177.17 (19)
C33—C34—C35—N31	−0.5 (2)	C354—C355—C356—C351	0.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···N32^i	0.93	2.55	3.483 (4)	177
C25—H25···N32^i	0.93	2.69	3.47 (2)	142
C314—H314···O1^ii	0.93	2.51	3.432 (3)	171

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