Functionalized 3-(5-ar­yloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(4-substituted-phen­yl)prop-2-en-1-ones: synthetic pathway, and the structures of six examples

Two series of functionalized chalcones have been synthesized from a common family of precursors, and the structures of three examples from each series have been determined. The supra­molecular assembly, based upon C—H...O and C—H...π(arene) hydrogen bonds, is different in all of the examples examined.

Key indicators

Structure: Ib

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.058
• wR factor = 0.155
• Data-to-parameter ratio = 19.0

Structure: Ic

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.048
• wR factor = 0.125
• Data-to-parameter ratio = 15.7

Structure: Ie

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.070
• wR factor = 0.187
• Data-to-parameter ratio = 13.0

Structure: IIa

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.050
• wR factor = 0.148
• Data-to-parameter ratio = 13.5

Structure: IId

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.006 Å
• Disorder in main residue
• R factor = 0.086
• wR factor = 0.155
• Data-to-parameter ratio = 10.9

Structure: IIe

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.063
• wR factor = 0.154
• Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Datablock: Ib


Alert level B
PLAT910_ALERT_3_B Missing # of FCF Reflection(s) Below Theta(Min).         12 Note

Alert level C
PLAT242_ALERT_2_C Low    MainMol Ueq as Compared to Neighbors of       C311 Check
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.056 Report
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         11 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          8 Note

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)       0.02 Degree
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         18 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          5 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
   1 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: Ic


Alert level C
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          9 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         11 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          7 Note

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.004 Degree
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         37 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          9 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
   4 ALERT level G = General information/check it is not something unexpected

   1 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
   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




Datablock: Ie


Alert level B
PLAT097_ALERT_2_B Large Reported Max.  (Positive) Residual Density       0.85 eA-3
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C352     --C353     .       11.5 s.u.
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C359     --C360     .       12.5 s.u.
PLAT910_ALERT_3_B Missing # of FCF Reflection(s) Below Theta(Min).         12 Note

Alert level C
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.93 Report
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C351     --C360     .        6.5 s.u.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C355     --C359     .        6.0 s.u.
PLAT242_ALERT_2_C Low    MainMol Ueq as Compared to Neighbors of       C360 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00444 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.361 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.598         38 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          9 Note

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.003 Degree
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        48% Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          3 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
   4 ALERT level B = A potentially serious problem, consider carefully
   9 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: IIa



Alert level C
PLAT018_ALERT_1_C _diffrn_measured_fraction_theta_max .NE. *_full           ! Check
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .         64 Ang   3
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.855 Report
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          9 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.596         34 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          6 Note

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        42% Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: IId



Alert level C
PLAT242_ALERT_2_C Low    MainMol Ueq as Compared to Neighbors of        N15 Check
PLAT334_ALERT_2_C Small Aver. Benzene C-C Dist C11      -C16             1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00632 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     37.121 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      5.556 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.145 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          5 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.595         19 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         18 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         18 Report
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large      10.52 Why ?
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          1 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          1 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        26% Note
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        291 Note
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        55% Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          3 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
  10 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check




Datablock: IIe



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N14      --N15      .        5.3 s.u.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00567 Ang.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -4.542 Report
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.043 Report
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          7 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.597         13 Report

Alert level G
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 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
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   0 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

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Computing details

For all structures, data collection: APEX3 (Bruker, 2016). Cell refinement: APEX3/SAINT V8.37A (Bruker, 2016) for (Ib), (Ic), (Ie), (IIa); APEX3/SAINT (Bruker, 2016) for (IId), (IIe). For all structures, data reduction: SAINT/XPREP (Bruker, 2016); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2020).

3-[5-(2-Chlorophenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl]-1-[4-(prop-2-yn-1-yloxy)phenyl]prop-2-en-1-one (Ib)

Crystal data

C28H21ClN2O3	Z = 2
Mr = 468.92	F(000) = 488
Triclinic, P1	Dx = 1.338 Mg m^−3
a = 9.909 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.193 (6) Å	Cell parameters from 7088 reflections
c = 12.024 (8) Å	θ = 3.0–31.0°
α = 90.94 (2)°	µ = 0.20 mm^−1
β = 106.27 (2)°	T = 297 K
γ = 92.75 (2)°	Block, colourless
V = 1163.9 (13) Å^3	0.18 × 0.15 × 0.10 mm

Data collection

Bruker APEXII diffractometer	5884 independent reflections
Radiation source: fine focussealed tube	4402 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
φ and ω scans	θmax = 28.6°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −13→13
Tmin = 0.833, Tmax = 0.980	k = −13→13
43789 measured reflections	l = −16→16

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)] = 0.058	w = 1/[σ^2(Fo^2) + (0.0448P)^2 + 0.9732P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.155	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.43 e Å^−3
5884 reflections	Δρmin = −0.41 e Å^−3
309 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.154 (8)
Primary atom site location: dual

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
C1	0.9482 (2)	0.3833 (2)	0.72250 (19)	0.0464 (5)
O1	1.0416 (2)	0.45886 (19)	0.78220 (17)	0.0709 (6)
C2	0.8469 (2)	0.4294 (2)	0.6173 (2)	0.0478 (5)
H2	0.7655	0.3779	0.5825	0.057*
C3	0.8698 (2)	0.5434 (2)	0.57132 (18)	0.0405 (4)
H3	0.9508	0.5925	0.6116	0.049*
C11	0.9385 (2)	0.2433 (2)	0.75289 (18)	0.0417 (5)
C12	1.0483 (2)	0.1947 (2)	0.8398 (2)	0.0486 (5)
H12	1.1247	0.2507	0.8778	0.058*
C13	1.0451 (2)	0.0655 (2)	0.8700 (2)	0.0488 (5)
H13	1.1197	0.0347	0.9274	0.059*
C14	0.9314 (2)	−0.0192 (2)	0.8155 (2)	0.0446 (5)
C15	0.8204 (3)	0.0268 (2)	0.7302 (2)	0.0511 (6)
H15	0.7431	−0.0292	0.6939	0.061*
C16	0.8253 (2)	0.1567 (2)	0.6991 (2)	0.0496 (5)
H16	0.7511	0.1868	0.6410	0.060*
O14	0.94132 (19)	−0.14583 (16)	0.85166 (17)	0.0576 (5)
C17	0.8187 (3)	−0.2343 (3)	0.8139 (3)	0.0654 (7)
H17A	0.8452	−0.3230	0.8345	0.078*
H17B	0.7829	−0.2328	0.7301	0.078*
C18	0.7077 (3)	−0.2002 (3)	0.8653 (3)	0.0608 (7)
C19	0.6186 (4)	−0.1767 (4)	0.9061 (3)	0.0824 (10)
H19	0.5469	−0.1578	0.9390	0.099*
N31	0.62180 (18)	0.64397 (15)	0.30547 (16)	0.0394 (4)
N32	0.71026 (19)	0.75523 (16)	0.33267 (16)	0.0425 (4)
C33	0.8087 (2)	0.72855 (19)	0.42829 (19)	0.0394 (4)
C34	0.7862 (2)	0.60108 (18)	0.46748 (18)	0.0373 (4)
C35	0.6653 (2)	0.55241 (18)	0.38607 (18)	0.0368 (4)
C311	0.4990 (2)	0.6447 (2)	0.20822 (19)	0.0424 (5)
C312	0.4418 (4)	0.5309 (3)	0.1454 (3)	0.0775 (10)
H312	0.4841	0.4517	0.1647	0.093*
C313	0.3214 (4)	0.5351 (3)	0.0534 (3)	0.0871 (11)
H313	0.2826	0.4581	0.0117	0.104*
C314	0.2589 (3)	0.6505 (3)	0.0231 (2)	0.0684 (8)
H314	0.1766	0.6523	−0.0375	0.082*
C315	0.3188 (4)	0.7634 (3)	0.0829 (3)	0.0777 (9)
H315	0.2781	0.8428	0.0615	0.093*
C316	0.4393 (3)	0.7612 (3)	0.1752 (2)	0.0639 (7)
H316	0.4797	0.8390	0.2146	0.077*
C331	0.9235 (3)	0.8287 (2)	0.4843 (2)	0.0514 (6)
H33A	0.9224	0.9001	0.4330	0.077*
H33B	1.0128	0.7893	0.5005	0.077*
H33C	0.9093	0.8613	0.5553	0.077*
O351	0.58686 (15)	0.43808 (13)	0.38387 (13)	0.0395 (3)
C351	0.6396 (2)	0.32381 (17)	0.35285 (17)	0.0335 (4)
C352	0.5909 (2)	0.20629 (18)	0.38930 (17)	0.0358 (4)
Cl52	0.47497 (6)	0.21019 (6)	0.47407 (5)	0.05086 (19)
C353	0.6332 (2)	0.08826 (19)	0.35823 (19)	0.0431 (5)
H353	0.6008	0.0102	0.3832	0.052*
C354	0.7248 (3)	0.0858 (2)	0.2892 (2)	0.0478 (5)
H354	0.7528	0.0060	0.2671	0.057*
C355	0.7740 (2)	0.2023 (2)	0.2537 (2)	0.0455 (5)
H355	0.8358	0.2006	0.2081	0.055*
C356	0.7321 (2)	0.32177 (19)	0.28541 (18)	0.0396 (4)
H356	0.7659	0.3999	0.2616	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0496 (12)	0.0438 (12)	0.0403 (11)	−0.0114 (9)	0.0060 (9)	0.0047 (9)
O1	0.0757 (13)	0.0561 (11)	0.0594 (11)	−0.0278 (9)	−0.0116 (9)	0.0101 (9)
C2	0.0484 (12)	0.0413 (11)	0.0463 (12)	−0.0082 (9)	0.0027 (10)	0.0037 (9)
C3	0.0404 (10)	0.0360 (10)	0.0430 (11)	−0.0028 (8)	0.0092 (8)	−0.0004 (8)
C11	0.0438 (11)	0.0435 (11)	0.0346 (10)	−0.0065 (9)	0.0072 (8)	0.0038 (8)
C12	0.0434 (11)	0.0512 (13)	0.0443 (11)	−0.0071 (9)	0.0027 (9)	0.0045 (10)
C13	0.0434 (12)	0.0514 (13)	0.0478 (12)	0.0026 (10)	0.0060 (9)	0.0089 (10)
C14	0.0501 (12)	0.0399 (11)	0.0460 (11)	0.0008 (9)	0.0174 (10)	0.0028 (9)
C15	0.0495 (13)	0.0445 (12)	0.0525 (13)	−0.0089 (10)	0.0050 (10)	0.0025 (10)
C16	0.0462 (12)	0.0477 (12)	0.0466 (12)	−0.0074 (10)	0.0005 (10)	0.0091 (10)
O14	0.0601 (10)	0.0410 (9)	0.0728 (12)	0.0041 (7)	0.0196 (9)	0.0106 (8)
C17	0.0797 (19)	0.0404 (13)	0.0728 (18)	−0.0059 (12)	0.0178 (15)	0.0014 (12)
C18	0.0536 (15)	0.0500 (14)	0.0678 (17)	−0.0125 (11)	0.0010 (13)	0.0083 (12)
C19	0.0546 (17)	0.088 (2)	0.096 (2)	−0.0109 (16)	0.0100 (17)	0.0045 (19)
N31	0.0418 (9)	0.0256 (8)	0.0468 (9)	−0.0026 (6)	0.0067 (7)	0.0027 (7)
N32	0.0465 (10)	0.0249 (8)	0.0515 (10)	−0.0059 (7)	0.0079 (8)	0.0017 (7)
C33	0.0426 (11)	0.0283 (9)	0.0468 (11)	−0.0032 (8)	0.0127 (9)	−0.0023 (8)
C34	0.0393 (10)	0.0273 (9)	0.0443 (11)	−0.0002 (7)	0.0104 (8)	0.0000 (8)
C35	0.0401 (10)	0.0243 (8)	0.0460 (11)	−0.0019 (7)	0.0127 (8)	0.0007 (7)
C311	0.0429 (11)	0.0378 (10)	0.0443 (11)	−0.0002 (8)	0.0085 (9)	0.0063 (8)
C312	0.086 (2)	0.0420 (14)	0.0768 (19)	−0.0110 (13)	−0.0211 (16)	0.0075 (13)
C313	0.094 (2)	0.0627 (18)	0.074 (2)	−0.0247 (16)	−0.0216 (18)	0.0134 (15)
C314	0.0563 (15)	0.089 (2)	0.0507 (14)	−0.0010 (14)	0.0002 (12)	0.0174 (14)
C315	0.087 (2)	0.076 (2)	0.0599 (17)	0.0339 (17)	−0.0013 (15)	0.0082 (15)
C316	0.0765 (18)	0.0487 (14)	0.0565 (15)	0.0156 (13)	0.0005 (13)	−0.0013 (11)
C331	0.0540 (13)	0.0357 (11)	0.0585 (14)	−0.0118 (9)	0.0084 (11)	−0.0002 (10)
O351	0.0391 (7)	0.0245 (6)	0.0563 (9)	−0.0031 (5)	0.0164 (6)	0.0009 (6)
C351	0.0338 (9)	0.0260 (8)	0.0374 (9)	−0.0023 (7)	0.0055 (7)	0.0005 (7)
C352	0.0353 (9)	0.0307 (9)	0.0382 (10)	−0.0063 (7)	0.0063 (8)	0.0020 (7)
Cl52	0.0522 (3)	0.0465 (3)	0.0582 (4)	−0.0102 (2)	0.0248 (3)	0.0016 (2)
C353	0.0521 (12)	0.0265 (9)	0.0479 (11)	−0.0043 (8)	0.0106 (9)	0.0040 (8)
C354	0.0604 (14)	0.0322 (10)	0.0508 (12)	0.0068 (9)	0.0149 (11)	0.0003 (9)
C355	0.0481 (12)	0.0432 (11)	0.0486 (12)	0.0061 (9)	0.0187 (10)	0.0035 (9)
C356	0.0409 (10)	0.0322 (10)	0.0460 (11)	−0.0023 (8)	0.0129 (9)	0.0062 (8)

Geometric parameters (Å, º)

C1—O1	1.228 (3)	C33—C331	1.492 (3)
C1—C2	1.477 (3)	C34—C35	1.382 (3)
C1—C11	1.484 (3)	C35—O351	1.365 (2)
C2—C3	1.331 (3)	C311—C316	1.367 (3)
C2—H2	0.9300	C311—C312	1.380 (3)
C3—C34	1.443 (3)	C312—C313	1.384 (4)
C3—H3	0.9300	C312—H312	0.9300
C11—C16	1.391 (3)	C313—C314	1.363 (5)
C11—C12	1.398 (3)	C313—H313	0.9300
C12—C13	1.373 (3)	C314—C315	1.364 (5)
C12—H12	0.9300	C314—H314	0.9300
C13—C14	1.385 (3)	C315—C316	1.385 (4)
C13—H13	0.9300	C315—H315	0.9300
C14—O14	1.368 (3)	C316—H316	0.9300
C14—C15	1.384 (3)	C331—H33A	0.9600
C15—C16	1.384 (3)	C331—H33B	0.9600
C15—H15	0.9300	C331—H33C	0.9600
C16—H16	0.9300	O351—C351	1.387 (2)
O14—C17	1.438 (3)	C351—C356	1.384 (3)
C17—C18	1.458 (4)	C351—C352	1.393 (3)
C17—H17A	0.9700	C352—C353	1.373 (3)
C17—H17B	0.9700	C352—Cl52	1.737 (2)
C18—C19	1.157 (5)	C353—C354	1.391 (3)
C19—H19	0.9300	C353—H353	0.9300
N31—C35	1.353 (3)	C354—C355	1.382 (3)
N31—N32	1.376 (2)	C354—H354	0.9300
N31—C311	1.433 (3)	C355—C356	1.386 (3)
N32—C33	1.325 (3)	C355—H355	0.9300
C33—C34	1.418 (3)	C356—H356	0.9300
O1—C1—C2	120.4 (2)	N31—C35—O351	120.93 (18)
O1—C1—C11	120.4 (2)	N31—C35—C34	109.00 (17)
C2—C1—C11	119.14 (19)	O351—C35—C34	129.85 (19)
C3—C2—C1	121.3 (2)	C316—C311—C312	119.3 (2)
C3—C2—H2	119.3	C316—C311—N31	119.2 (2)
C1—C2—H2	119.3	C312—C311—N31	121.5 (2)
C2—C3—C34	128.8 (2)	C311—C312—C313	119.8 (3)
C2—C3—H3	115.6	C311—C312—H312	120.1
C34—C3—H3	115.6	C313—C312—H312	120.1
C16—C11—C12	117.7 (2)	C314—C313—C312	120.9 (3)
C16—C11—C1	123.4 (2)	C314—C313—H313	119.6
C12—C11—C1	118.86 (19)	C312—C313—H313	119.6
C13—C12—C11	121.1 (2)	C313—C314—C315	119.1 (3)
C13—C12—H12	119.5	C313—C314—H314	120.5
C11—C12—H12	119.5	C315—C314—H314	120.5
C12—C13—C14	120.4 (2)	C314—C315—C316	120.9 (3)
C12—C13—H13	119.8	C314—C315—H315	119.6
C14—C13—H13	119.8	C316—C315—H315	119.6
O14—C14—C15	125.2 (2)	C311—C316—C315	120.0 (3)
O14—C14—C13	115.0 (2)	C311—C316—H316	120.0
C15—C14—C13	119.8 (2)	C315—C316—H316	120.0
C16—C15—C14	119.5 (2)	C33—C331—H33A	109.5
C16—C15—H15	120.2	C33—C331—H33B	109.5
C14—C15—H15	120.2	H33A—C331—H33B	109.5
C15—C16—C11	121.6 (2)	C33—C331—H33C	109.5
C15—C16—H16	119.2	H33A—C331—H33C	109.5
C11—C16—H16	119.2	H33B—C331—H33C	109.5
C14—O14—C17	118.3 (2)	C35—O351—C351	117.09 (16)
O14—C17—C18	112.3 (2)	C356—C351—O351	123.40 (17)
O14—C17—H17A	109.1	C356—C351—C352	119.82 (18)
C18—C17—H17A	109.1	O351—C351—C352	116.73 (18)
O14—C17—H17B	109.1	C353—C352—C351	120.49 (19)
C18—C17—H17B	109.1	C353—C352—Cl52	120.13 (15)
H17A—C17—H17B	107.9	C351—C352—Cl52	119.38 (16)
C19—C18—C17	178.1 (3)	C352—C353—C354	119.80 (19)
C18—C19—H19	180.0	C352—C353—H353	120.1
C35—N31—N32	110.06 (17)	C354—C353—H353	120.1
C35—N31—C311	130.75 (17)	C355—C354—C353	119.8 (2)
N32—N31—C311	118.98 (16)	C355—C354—H354	120.1
C33—N32—N31	105.58 (16)	C353—C354—H354	120.1
N32—C33—C34	112.02 (18)	C354—C355—C356	120.6 (2)
N32—C33—C331	120.60 (19)	C354—C355—H355	119.7
C34—C33—C331	127.3 (2)	C356—C355—H355	119.7
C35—C34—C33	103.31 (18)	C351—C356—C355	119.51 (18)
C35—C34—C3	130.32 (19)	C351—C356—H356	120.2
C33—C34—C3	126.33 (19)	C355—C356—H356	120.2
O1—C1—C2—C3	13.8 (4)	C311—N31—C35—C34	−175.8 (2)
C11—C1—C2—C3	−164.2 (2)	C33—C34—C35—N31	0.5 (2)
C1—C2—C3—C34	177.4 (2)	C3—C34—C35—N31	178.0 (2)
O1—C1—C11—C16	171.0 (2)	C33—C34—C35—O351	−174.0 (2)
C2—C1—C11—C16	−11.1 (4)	C3—C34—C35—O351	3.5 (4)
O1—C1—C11—C12	−9.2 (4)	C35—N31—C311—C316	147.1 (3)
C2—C1—C11—C12	168.8 (2)	N32—N31—C311—C316	−27.1 (3)
C16—C11—C12—C13	0.7 (4)	C35—N31—C311—C312	−34.7 (4)
C1—C11—C12—C13	−179.2 (2)	N32—N31—C311—C312	151.1 (3)
C11—C12—C13—C14	−0.8 (4)	C316—C311—C312—C313	−3.1 (5)
C12—C13—C14—O14	179.0 (2)	N31—C311—C312—C313	178.7 (3)
C12—C13—C14—C15	−0.1 (4)	C311—C312—C313—C314	0.7 (6)
O14—C14—C15—C16	−178.1 (2)	C312—C313—C314—C315	1.7 (6)
C13—C14—C15—C16	0.9 (4)	C313—C314—C315—C316	−1.6 (5)
C14—C15—C16—C11	−1.0 (4)	C312—C311—C316—C315	3.1 (5)
C12—C11—C16—C15	0.1 (4)	N31—C311—C316—C315	−178.6 (3)
C1—C11—C16—C15	−180.0 (2)	C314—C315—C316—C311	−0.8 (5)
C15—C14—O14—C17	−11.2 (4)	N31—C35—O351—C351	109.4 (2)
C13—C14—O14—C17	169.8 (2)	C34—C35—O351—C351	−76.7 (3)
C14—O14—C17—C18	−68.7 (3)	C35—O351—C351—C356	−24.8 (3)
C35—N31—N32—C33	1.5 (2)	C35—O351—C351—C352	157.64 (18)
C311—N31—N32—C33	176.81 (18)	C356—C351—C352—C353	−0.4 (3)
N31—N32—C33—C34	−1.2 (2)	O351—C351—C352—C353	177.27 (18)
N31—N32—C33—C331	−179.43 (19)	C356—C351—C352—Cl52	179.92 (15)
N32—C33—C34—C35	0.5 (2)	O351—C351—C352—Cl52	−2.4 (2)
C331—C33—C34—C35	178.5 (2)	C351—C352—C353—C354	−0.4 (3)
N32—C33—C34—C3	−177.2 (2)	Cl52—C352—C353—C354	179.26 (17)
C331—C33—C34—C3	0.9 (4)	C352—C353—C354—C355	0.9 (3)
C2—C3—C34—C35	−3.3 (4)	C353—C354—C355—C356	−0.5 (4)
C2—C3—C34—C33	173.7 (2)	O351—C351—C356—C355	−176.76 (19)
N32—N31—C35—O351	173.80 (17)	C352—C351—C356—C355	0.8 (3)
C311—N31—C35—O351	−0.8 (3)	C354—C355—C356—C351	−0.3 (3)
N32—N31—C35—C34	−1.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C355—H355···O14^i	0.93	2.59	3.468 (4)	158
C356—H356···O1^ii	0.93	2.51	3.360 (4)	152

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

3-[5-(4-Chlorophenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl]-1-[4-(prop-2-yn-1-yloxy)phenyl]prop-2-en-1-one (Ic)

Crystal data

C28H21ClN2O3	Z = 2
Mr = 468.92	F(000) = 488
Triclinic, P1	Dx = 1.322 Mg m^−3
a = 8.9959 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.7380 (15) Å	Cell parameters from 4839 reflections
c = 13.637 (2) Å	θ = 2.9–26.5°
α = 95.901 (4)°	µ = 0.20 mm^−1
β = 94.122 (4)°	T = 297 K
γ = 95.959 (4)°	Block, brown
V = 1177.8 (3) Å^3	0.20 × 0.15 × 0.15 mm

Data collection

Bruker APEXII diffractometer	4837 independent reflections
Radiation source: fine focussealed tube	3930 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
φ and ω scans	θmax = 26.5°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −11→11
Tmin = 0.901, Tmax = 0.971	k = −12→12
49011 measured reflections	l = −17→17

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)] = 0.048	w = 1/[σ^2(Fo^2) + (0.0384P)^2 + 0.6832P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.125	(Δ/σ)max = 0.001
S = 1.15	Δρmax = 0.35 e Å^−3
4837 reflections	Δρmin = −0.45 e Å^−3
309 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.092 (6)
Primary atom site location: dual

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
C1	0.5453 (2)	0.2711 (2)	0.53901 (14)	0.0354 (4)
O1	0.49212 (18)	0.19336 (17)	0.46533 (11)	0.0535 (4)
C2	0.5001 (2)	0.2494 (2)	0.63858 (14)	0.0375 (4)
H2	0.5266	0.3202	0.6899	0.045*
C3	0.4233 (2)	0.1329 (2)	0.65779 (14)	0.0360 (4)
H3	0.3999	0.0635	0.6051	0.043*
C11	0.65551 (19)	0.39198 (18)	0.52879 (13)	0.0321 (4)
C12	0.6706 (2)	0.4355 (2)	0.43611 (13)	0.0366 (4)
H12	0.6103	0.3890	0.3821	0.044*
C13	0.7725 (2)	0.54596 (19)	0.42185 (14)	0.0373 (4)
H13	0.7803	0.5739	0.3591	0.045*
C14	0.8635 (2)	0.61513 (19)	0.50232 (14)	0.0351 (4)
C15	0.8509 (2)	0.5724 (2)	0.59521 (14)	0.0430 (5)
H15	0.9124	0.6180	0.6490	0.052*
C16	0.7477 (2)	0.4627 (2)	0.60857 (14)	0.0408 (5)
H16	0.7394	0.4355	0.6715	0.049*
O14	0.96866 (16)	0.72487 (15)	0.49739 (10)	0.0466 (4)
C17	0.9800 (2)	0.7763 (2)	0.40407 (16)	0.0456 (5)
H17A	0.8869	0.8110	0.3832	0.055*
H17B	0.9987	0.7023	0.3548	0.055*
C18	1.1030 (2)	0.8878 (2)	0.41364 (16)	0.0445 (5)
C19	1.2031 (3)	0.9760 (2)	0.41795 (18)	0.0541 (6)
H19	1.2825	1.0460	0.4214	0.065*
N31	0.32759 (17)	0.10603 (16)	0.91019 (11)	0.0359 (4)
N32	0.23589 (18)	−0.00607 (17)	0.86251 (12)	0.0387 (4)
C33	0.2648 (2)	−0.00897 (19)	0.76832 (14)	0.0350 (4)
C34	0.37180 (19)	0.10233 (19)	0.75252 (13)	0.0324 (4)
C35	0.4074 (2)	0.17216 (19)	0.84574 (13)	0.0333 (4)
C311	0.3251 (2)	0.14030 (19)	1.01431 (14)	0.0376 (4)
C312	0.4578 (3)	0.1772 (2)	1.07284 (16)	0.0498 (5)
H312	0.5492	0.1809	1.0449	0.060*
C313	0.4527 (3)	0.2086 (3)	1.17386 (18)	0.0639 (7)
H313	0.5415	0.2351	1.2136	0.077*
C314	0.3191 (4)	0.2013 (3)	1.21603 (18)	0.0660 (7)
H314	0.3172	0.2223	1.2840	0.079*
C315	0.1875 (3)	0.1625 (3)	1.15721 (19)	0.0633 (7)
H315	0.0966	0.1564	1.1858	0.076*
C316	0.1892 (3)	0.1326 (2)	1.05553 (16)	0.0478 (5)
H316	0.1001	0.1077	1.0158	0.057*
C331	0.1866 (3)	−0.1197 (2)	0.69277 (16)	0.0485 (5)
H33A	0.1505	−0.1984	0.7248	0.073*
H33B	0.2555	−0.1473	0.6458	0.073*
H33C	0.1037	−0.0845	0.6591	0.073*
O351	0.48920 (15)	0.29585 (13)	0.87828 (10)	0.0397 (3)
C351	0.6443 (2)	0.31066 (19)	0.87288 (13)	0.0335 (4)
C352	0.7128 (2)	0.4453 (2)	0.89176 (16)	0.0431 (5)
H352	0.6565	0.5182	0.9075	0.052*
C353	0.8669 (2)	0.4705 (2)	0.88698 (16)	0.0460 (5)
H353	0.9148	0.5607	0.8994	0.055*
C354	0.9481 (2)	0.3613 (2)	0.86373 (14)	0.0415 (5)
Cl54	1.14061 (6)	0.39375 (8)	0.85575 (5)	0.0630 (2)
C355	0.8803 (2)	0.2275 (2)	0.84574 (16)	0.0458 (5)
H355	0.9369	0.1547	0.8305	0.055*
C356	0.7260 (2)	0.2015 (2)	0.85043 (16)	0.0422 (5)
H356	0.6785	0.1112	0.8385	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0323 (9)	0.0385 (10)	0.0340 (9)	−0.0033 (7)	0.0052 (7)	0.0035 (8)
O1	0.0583 (9)	0.0560 (9)	0.0383 (8)	−0.0266 (7)	0.0049 (7)	0.0008 (7)
C2	0.0375 (10)	0.0407 (10)	0.0334 (9)	−0.0029 (8)	0.0059 (7)	0.0046 (8)
C3	0.0340 (9)	0.0396 (10)	0.0338 (9)	−0.0022 (8)	0.0067 (7)	0.0042 (8)
C11	0.0306 (9)	0.0326 (9)	0.0323 (9)	−0.0010 (7)	0.0053 (7)	0.0020 (7)
C12	0.0371 (10)	0.0393 (10)	0.0307 (9)	−0.0050 (8)	0.0015 (7)	0.0014 (7)
C13	0.0399 (10)	0.0376 (10)	0.0339 (9)	−0.0031 (8)	0.0041 (8)	0.0074 (8)
C14	0.0329 (9)	0.0306 (9)	0.0401 (10)	−0.0043 (7)	0.0071 (7)	0.0002 (7)
C15	0.0430 (11)	0.0469 (11)	0.0332 (10)	−0.0121 (9)	0.0010 (8)	−0.0040 (8)
C16	0.0433 (11)	0.0464 (11)	0.0300 (9)	−0.0092 (9)	0.0050 (8)	0.0045 (8)
O14	0.0492 (8)	0.0414 (8)	0.0439 (8)	−0.0179 (6)	0.0045 (6)	0.0028 (6)
C17	0.0423 (11)	0.0432 (11)	0.0492 (12)	−0.0097 (9)	0.0002 (9)	0.0125 (9)
C18	0.0425 (11)	0.0422 (11)	0.0486 (12)	−0.0027 (9)	0.0061 (9)	0.0095 (9)
C19	0.0508 (13)	0.0523 (13)	0.0564 (13)	−0.0144 (10)	0.0057 (10)	0.0119 (10)
N31	0.0378 (8)	0.0370 (8)	0.0320 (8)	−0.0017 (7)	0.0059 (6)	0.0035 (6)
N32	0.0384 (8)	0.0393 (9)	0.0370 (8)	−0.0047 (7)	0.0066 (7)	0.0040 (7)
C33	0.0336 (9)	0.0352 (9)	0.0357 (9)	−0.0014 (7)	0.0045 (7)	0.0059 (7)
C34	0.0305 (8)	0.0340 (9)	0.0330 (9)	0.0010 (7)	0.0051 (7)	0.0062 (7)
C35	0.0306 (9)	0.0330 (9)	0.0359 (9)	0.0003 (7)	0.0046 (7)	0.0033 (7)
C311	0.0488 (11)	0.0342 (9)	0.0317 (9)	0.0091 (8)	0.0076 (8)	0.0055 (7)
C312	0.0551 (13)	0.0560 (13)	0.0395 (11)	0.0168 (10)	0.0017 (9)	0.0015 (9)
C313	0.0885 (19)	0.0621 (15)	0.0411 (12)	0.0254 (14)	−0.0089 (12)	−0.0017 (11)
C314	0.111 (2)	0.0559 (15)	0.0355 (12)	0.0270 (15)	0.0143 (14)	0.0046 (10)
C315	0.0897 (19)	0.0548 (14)	0.0540 (14)	0.0181 (13)	0.0390 (14)	0.0136 (11)
C316	0.0553 (13)	0.0459 (12)	0.0455 (12)	0.0062 (10)	0.0177 (10)	0.0104 (9)
C331	0.0481 (12)	0.0482 (12)	0.0439 (11)	−0.0120 (9)	0.0045 (9)	−0.0027 (9)
O351	0.0352 (7)	0.0334 (7)	0.0484 (8)	−0.0014 (5)	0.0065 (6)	−0.0024 (6)
C351	0.0350 (9)	0.0334 (9)	0.0314 (9)	0.0010 (7)	0.0026 (7)	0.0027 (7)
C352	0.0432 (11)	0.0320 (10)	0.0518 (12)	0.0024 (8)	0.0019 (9)	−0.0028 (8)
C353	0.0460 (11)	0.0387 (11)	0.0490 (12)	−0.0073 (9)	−0.0020 (9)	0.0009 (9)
C354	0.0363 (10)	0.0530 (12)	0.0333 (10)	0.0000 (9)	0.0001 (8)	0.0024 (8)
Cl54	0.0371 (3)	0.0877 (5)	0.0605 (4)	−0.0021 (3)	0.0037 (2)	0.0001 (3)
C355	0.0422 (11)	0.0451 (11)	0.0500 (12)	0.0100 (9)	0.0022 (9)	0.0000 (9)
C356	0.0428 (11)	0.0324 (10)	0.0494 (11)	0.0010 (8)	0.0022 (9)	0.0002 (8)

Geometric parameters (Å, º)

C1—O1	1.229 (2)	C33—C331	1.493 (3)
C1—C2	1.474 (3)	C34—C35	1.378 (3)
C1—C11	1.483 (2)	C35—O351	1.360 (2)
C2—C3	1.327 (3)	C311—C316	1.380 (3)
C2—H2	0.9300	C311—C312	1.380 (3)
C3—C34	1.452 (2)	C312—C313	1.385 (3)
C3—H3	0.9300	C312—H312	0.9300
C11—C12	1.385 (3)	C313—C314	1.367 (4)
C11—C16	1.394 (3)	C313—H313	0.9300
C12—C13	1.378 (3)	C314—C315	1.377 (4)
C12—H12	0.9300	C314—H314	0.9300
C13—C14	1.390 (3)	C315—C316	1.389 (3)
C13—H13	0.9300	C315—H315	0.9300
C14—O14	1.362 (2)	C316—H316	0.9300
C14—C15	1.382 (3)	C331—H33A	0.9600
C15—C16	1.376 (3)	C331—H33B	0.9600
C15—H15	0.9300	C331—H33C	0.9600
C16—H16	0.9300	O351—C351	1.396 (2)
O14—C17	1.421 (2)	C351—C356	1.375 (3)
C17—C18	1.456 (3)	C351—C352	1.380 (3)
C17—H17A	0.9700	C352—C353	1.391 (3)
C17—H17B	0.9700	C352—H352	0.9300
C18—C19	1.172 (3)	C353—C354	1.374 (3)
C19—H19	0.9300	C353—H353	0.9300
N31—C35	1.347 (2)	C354—C355	1.370 (3)
N31—N32	1.373 (2)	C354—Cl54	1.741 (2)
N31—C311	1.427 (2)	C355—C356	1.393 (3)
N32—C33	1.327 (2)	C355—H355	0.9300
C33—C34	1.418 (2)	C356—H356	0.9300
O1—C1—C2	121.66 (17)	N31—C35—O351	118.65 (16)
O1—C1—C11	120.01 (16)	N31—C35—C34	108.52 (15)
C2—C1—C11	118.32 (16)	O351—C35—C34	132.30 (16)
C3—C2—C1	122.56 (18)	C316—C311—C312	120.78 (19)
C3—C2—H2	118.7	C316—C311—N31	119.17 (19)
C1—C2—H2	118.7	C312—C311—N31	120.03 (18)
C2—C3—C34	126.73 (18)	C311—C312—C313	119.0 (2)
C2—C3—H3	116.6	C311—C312—H312	120.5
C34—C3—H3	116.6	C313—C312—H312	120.5
C12—C11—C16	118.11 (16)	C314—C313—C312	121.0 (3)
C12—C11—C1	119.13 (16)	C314—C313—H313	119.5
C16—C11—C1	122.75 (16)	C312—C313—H313	119.5
C13—C12—C11	121.74 (17)	C313—C314—C315	119.5 (2)
C13—C12—H12	119.1	C313—C314—H314	120.2
C11—C12—H12	119.1	C315—C314—H314	120.2
C12—C13—C14	119.29 (17)	C314—C315—C316	120.6 (2)
C12—C13—H13	120.4	C314—C315—H315	119.7
C14—C13—H13	120.4	C316—C315—H315	119.7
O14—C14—C15	115.58 (16)	C311—C316—C315	119.0 (2)
O14—C14—C13	124.66 (17)	C311—C316—H316	120.5
C15—C14—C13	119.77 (16)	C315—C316—H316	120.5
C16—C15—C14	120.34 (17)	C33—C331—H33A	109.5
C16—C15—H15	119.8	C33—C331—H33B	109.5
C14—C15—H15	119.8	H33A—C331—H33B	109.5
C15—C16—C11	120.75 (17)	C33—C331—H33C	109.5
C15—C16—H16	119.6	H33A—C331—H33C	109.5
C11—C16—H16	119.6	H33B—C331—H33C	109.5
C14—O14—C17	117.27 (15)	C35—O351—C351	119.84 (14)
O14—C17—C18	108.51 (17)	C356—C351—C352	121.22 (18)
O14—C17—H17A	110.0	C356—C351—O351	123.80 (16)
C18—C17—H17A	110.0	C352—C351—O351	114.98 (16)
O14—C17—H17B	110.0	C351—C352—C353	119.14 (19)
C18—C17—H17B	110.0	C351—C352—H352	120.4
H17A—C17—H17B	108.4	C353—C352—H352	120.4
C19—C18—C17	177.6 (2)	C354—C353—C352	119.52 (19)
C18—C19—H19	180.0	C354—C353—H353	120.2
C35—N31—N32	110.96 (15)	C352—C353—H353	120.2
C35—N31—C311	129.06 (16)	C355—C354—C353	121.34 (19)
N32—N31—C311	119.96 (15)	C355—C354—Cl54	119.29 (17)
C33—N32—N31	104.91 (14)	C353—C354—Cl54	119.37 (16)
N32—C33—C34	112.02 (16)	C354—C355—C356	119.44 (19)
N32—C33—C331	120.58 (17)	C354—C355—H355	120.3
C34—C33—C331	127.39 (17)	C356—C355—H355	120.3
C35—C34—C33	103.56 (15)	C351—C356—C355	119.34 (18)
C35—C34—C3	130.35 (17)	C351—C356—H356	120.3
C33—C34—C3	126.06 (17)	C355—C356—H356	120.3
O1—C1—C2—C3	13.1 (3)	N32—N31—C35—C34	−1.2 (2)
C11—C1—C2—C3	−168.12 (19)	C311—N31—C35—C34	−179.14 (18)
C1—C2—C3—C34	−179.02 (18)	C33—C34—C35—N31	0.2 (2)
O1—C1—C11—C12	15.4 (3)	C3—C34—C35—N31	178.15 (19)
C2—C1—C11—C12	−163.41 (18)	C33—C34—C35—O351	−171.11 (19)
O1—C1—C11—C16	−163.3 (2)	C3—C34—C35—O351	6.8 (3)
C2—C1—C11—C16	17.9 (3)	C35—N31—C311—C316	136.4 (2)
C16—C11—C12—C13	−0.4 (3)	N32—N31—C311—C316	−41.4 (3)
C1—C11—C12—C13	−179.10 (18)	C35—N31—C311—C312	−45.3 (3)
C11—C12—C13—C14	0.4 (3)	N32—N31—C311—C312	137.0 (2)
C12—C13—C14—O14	179.64 (18)	C316—C311—C312—C313	−1.0 (3)
C12—C13—C14—C15	0.1 (3)	N31—C311—C312—C313	−179.3 (2)
O14—C14—C15—C16	179.76 (19)	C311—C312—C313—C314	1.1 (4)
C13—C14—C15—C16	−0.6 (3)	C312—C313—C314—C315	−0.2 (4)
C14—C15—C16—C11	0.7 (3)	C313—C314—C315—C316	−0.8 (4)
C12—C11—C16—C15	−0.2 (3)	C312—C311—C316—C315	0.0 (3)
C1—C11—C16—C15	178.48 (19)	N31—C311—C316—C315	178.35 (19)
C15—C14—O14—C17	−176.97 (19)	C314—C315—C316—C311	0.9 (3)
C13—C14—O14—C17	3.5 (3)	N31—C35—O351—C351	120.05 (18)
C14—O14—C17—C18	−177.14 (18)	C34—C35—O351—C351	−69.3 (3)
C35—N31—N32—C33	1.7 (2)	C35—O351—C351—C356	−10.4 (3)
C311—N31—N32—C33	179.86 (16)	C35—O351—C351—C352	169.43 (17)
N31—N32—C33—C34	−1.6 (2)	C356—C351—C352—C353	0.6 (3)
N31—N32—C33—C331	179.10 (18)	O351—C351—C352—C353	−179.26 (18)
N32—C33—C34—C35	0.9 (2)	C351—C352—C353—C354	−0.1 (3)
C331—C33—C34—C35	−179.9 (2)	C352—C353—C354—C355	−0.4 (3)
N32—C33—C34—C3	−177.16 (18)	C352—C353—C354—Cl54	178.92 (16)
C331—C33—C34—C3	2.1 (3)	C353—C354—C355—C356	0.4 (3)
C2—C3—C34—C35	−11.4 (3)	Cl54—C354—C355—C356	−178.93 (16)
C2—C3—C34—C33	166.1 (2)	C352—C351—C356—C355	−0.6 (3)
N32—N31—C35—O351	171.48 (15)	O351—C351—C356—C355	179.23 (18)
C311—N31—C35—O351	−6.4 (3)	C354—C355—C356—C351	0.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···O1^i	0.93	2.25	3.161 (3)	165
C16—H16···Cg2	0.93	2.98	3.882 (2)	165
C356—H356···Cg1^ii	0.93	2.88	3.685 (2)	146

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

3-[3-Methyl-5-(naphthalen-2-yloxy)-1-phenyl-1H-pyrazol-4-yl]-1-[4-(prop-2-ynyloxy)phenyl]prop-2-en-1-one (Ie)

Crystal data

C32H24N2O3	Z = 2
Mr = 484.53	F(000) = 508
Triclinic, P1	Dx = 1.307 Mg m^−3
a = 8.8615 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.4973 (7) Å	Cell parameters from 4376 reflections
c = 13.6588 (10) Å	θ = 3.0–25.2°
α = 79.006 (3)°	µ = 0.08 mm^−1
β = 89.412 (3)°	T = 297 K
γ = 80.971 (3)°	Block, brown
V = 1231.54 (15) Å^3	0.20 × 0.16 × 0.16 mm

Data collection

Bruker APEXII diffractometer	4373 independent reflections
Radiation source: fine focussealed tube	3474 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
φ and ω scans	θmax = 25.2°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −10→10
Tmin = 0.898, Tmax = 0.987	k = −12→12
30613 measured reflections	l = −16→16

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)] = 0.070	w = 1/[σ^2(Fo^2) + (0.0694P)^2 + 1.3194P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.187	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.85 e Å^−3
4373 reflections	Δρmin = −0.29 e Å^−3
336 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.114 (12)
Primary atom site location: dual

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
C1	0.4597 (3)	0.2692 (3)	0.9522 (2)	0.0466 (6)
O1	0.5161 (3)	0.1921 (2)	1.02722 (15)	0.0682 (7)
C2	0.5008 (3)	0.2472 (3)	0.8514 (2)	0.0479 (7)
H2	0.4710	0.3145	0.7970	0.057*
C3	0.5789 (3)	0.1344 (3)	0.8354 (2)	0.0456 (6)
H3	0.6058	0.0694	0.8916	0.055*
C11	0.3503 (3)	0.3873 (3)	0.96264 (18)	0.0421 (6)
C12	0.3407 (3)	0.4290 (3)	1.0532 (2)	0.0491 (7)
H12	0.4032	0.3815	1.1063	0.059*
C13	0.2408 (3)	0.5392 (3)	1.0669 (2)	0.0501 (7)
H13	0.2376	0.5664	1.1279	0.060*
C14	0.1454 (3)	0.6086 (3)	0.9883 (2)	0.0463 (6)
C15	0.1510 (3)	0.5671 (3)	0.8978 (2)	0.0539 (7)
H15	0.0854	0.6126	0.8457	0.065*
C16	0.2528 (3)	0.4595 (3)	0.8848 (2)	0.0516 (7)
H16	0.2572	0.4340	0.8232	0.062*
O14	0.0419 (2)	0.7179 (2)	0.99303 (15)	0.0600 (6)
C17	0.0309 (4)	0.7627 (3)	1.0852 (2)	0.0584 (8)
H17A	0.1258	0.7910	1.0999	0.070*
H17B	0.0129	0.6918	1.1387	0.070*
C18	−0.0948 (4)	0.8721 (3)	1.0781 (2)	0.0584 (8)
C19	−0.1963 (4)	0.9573 (4)	1.0761 (3)	0.0695 (9)
H19	−0.2776	1.0256	1.0745	0.083*
N31	0.6678 (2)	0.0973 (2)	0.58075 (16)	0.0441 (5)
N32	0.7581 (3)	−0.0141 (2)	0.63236 (16)	0.0481 (6)
C33	0.7313 (3)	−0.0118 (3)	0.72742 (19)	0.0439 (6)
C34	0.6271 (3)	0.1007 (3)	0.74080 (19)	0.0415 (6)
C35	0.5907 (3)	0.1663 (2)	0.64457 (19)	0.0423 (6)
C311	0.6675 (3)	0.1256 (3)	0.47431 (19)	0.0435 (6)
C312	0.5324 (3)	0.1747 (3)	0.4211 (2)	0.0591 (8)
H312	0.4408	0.1889	0.4542	0.071*
C313	0.5349 (4)	0.2025 (4)	0.3179 (2)	0.0681 (9)
H313	0.4444	0.2372	0.2819	0.082*
C314	0.6679 (4)	0.1798 (3)	0.2679 (2)	0.0631 (9)
H314	0.6683	0.1990	0.1986	0.076*
C315	0.8004 (4)	0.1285 (3)	0.3216 (2)	0.0640 (9)
H315	0.8910	0.1114	0.2881	0.077*
C316	0.8019 (3)	0.1014 (3)	0.4253 (2)	0.0535 (7)
H316	0.8927	0.0674	0.4610	0.064*
C331	0.8082 (4)	−0.1185 (3)	0.8078 (2)	0.0595 (8)
H33A	0.8606	−0.1889	0.7786	0.089*
H33B	0.7331	−0.1508	0.8529	0.089*
H33C	0.8805	−0.0843	0.8435	0.089*
O351	0.5097 (2)	0.28760 (18)	0.60811 (15)	0.0528 (5)
C351	0.2781 (4)	0.4338 (3)	0.6115 (2)	0.0550 (7)
H351	0.3356	0.5017	0.5971	0.066*
C352	0.3475 (3)	0.3071 (3)	0.62206 (19)	0.0507 (7)
C353	0.2669 (4)	0.2018 (3)	0.6420 (2)	0.0595 (8)
H353	0.3175	0.1160	0.6483	0.071*
C354	0.1103 (4)	0.2270 (3)	0.6523 (3)	0.0669 (9)
H354	0.0553	0.1573	0.6654	0.080*
C355	−0.1287 (4)	0.3815 (4)	0.6550 (3)	0.0695 (10)
H355	−0.1864	0.3137	0.6686	0.083*
C356	−0.1961 (4)	0.5079 (4)	0.6457 (3)	0.0737 (10)
H356	−0.3013	0.5257	0.6533	0.088*
C357	−0.1145 (5)	0.6132 (4)	0.6250 (3)	0.0791 (11)
H357	−0.1648	0.6991	0.6188	0.095*
C358	0.0361 (4)	0.5891 (4)	0.6142 (3)	0.0722 (10)
H358	0.0898	0.6596	0.6005	0.087*
C359	0.0346 (4)	0.3537 (3)	0.6434 (2)	0.0589 (8)
C360	0.1159 (3)	0.4629 (3)	0.62260 (19)	0.0447 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0466 (15)	0.0465 (15)	0.0434 (15)	0.0048 (12)	−0.0025 (12)	−0.0100 (12)
O1	0.0799 (15)	0.0664 (14)	0.0440 (12)	0.0306 (12)	−0.0081 (10)	−0.0086 (10)
C2	0.0506 (16)	0.0482 (15)	0.0404 (14)	0.0053 (12)	−0.0009 (12)	−0.0081 (12)
C3	0.0443 (14)	0.0458 (15)	0.0430 (14)	0.0025 (12)	−0.0013 (11)	−0.0073 (11)
C11	0.0435 (14)	0.0418 (14)	0.0369 (13)	0.0038 (11)	−0.0001 (11)	−0.0057 (11)
C12	0.0500 (16)	0.0516 (16)	0.0394 (14)	0.0096 (13)	−0.0072 (12)	−0.0066 (12)
C13	0.0572 (17)	0.0491 (16)	0.0403 (14)	0.0077 (13)	−0.0031 (12)	−0.0125 (12)
C14	0.0474 (15)	0.0408 (14)	0.0455 (15)	0.0065 (11)	0.0018 (12)	−0.0064 (11)
C15	0.0555 (17)	0.0577 (17)	0.0395 (15)	0.0138 (14)	−0.0085 (12)	−0.0047 (12)
C16	0.0578 (17)	0.0541 (17)	0.0371 (14)	0.0104 (13)	−0.0051 (12)	−0.0098 (12)
O14	0.0669 (13)	0.0537 (12)	0.0499 (12)	0.0219 (10)	−0.0050 (10)	−0.0115 (9)
C17	0.0588 (18)	0.0567 (18)	0.0560 (18)	0.0116 (14)	−0.0046 (14)	−0.0186 (14)
C18	0.0595 (18)	0.0551 (18)	0.0574 (18)	0.0067 (15)	0.0010 (14)	−0.0154 (14)
C19	0.069 (2)	0.069 (2)	0.065 (2)	0.0181 (18)	0.0005 (16)	−0.0209 (17)
N31	0.0445 (12)	0.0460 (12)	0.0375 (12)	0.0039 (10)	−0.0017 (9)	−0.0063 (9)
N32	0.0472 (13)	0.0491 (13)	0.0411 (12)	0.0104 (10)	−0.0011 (10)	−0.0058 (10)
C33	0.0415 (14)	0.0466 (15)	0.0399 (14)	0.0034 (11)	−0.0016 (11)	−0.0070 (11)
C34	0.0405 (13)	0.0416 (14)	0.0402 (14)	0.0016 (11)	−0.0006 (11)	−0.0093 (11)
C35	0.0400 (13)	0.0393 (13)	0.0442 (14)	0.0031 (11)	−0.0019 (11)	−0.0073 (11)
C311	0.0474 (15)	0.0425 (14)	0.0391 (14)	−0.0045 (11)	−0.0006 (11)	−0.0063 (11)
C312	0.0474 (16)	0.080 (2)	0.0448 (16)	−0.0008 (15)	−0.0030 (13)	−0.0073 (15)
C313	0.068 (2)	0.082 (2)	0.0475 (18)	−0.0024 (18)	−0.0128 (15)	−0.0033 (16)
C314	0.088 (2)	0.0583 (19)	0.0422 (16)	−0.0131 (17)	0.0016 (16)	−0.0058 (14)
C315	0.071 (2)	0.064 (2)	0.0561 (19)	−0.0086 (16)	0.0194 (16)	−0.0115 (15)
C316	0.0483 (16)	0.0547 (17)	0.0538 (17)	0.0009 (13)	0.0028 (13)	−0.0084 (13)
C331	0.0629 (19)	0.0568 (18)	0.0476 (16)	0.0169 (15)	0.0012 (14)	−0.0034 (13)
O351	0.0560 (12)	0.0400 (10)	0.0550 (12)	0.0056 (9)	−0.0027 (9)	−0.0010 (8)
C351	0.0598 (18)	0.0475 (16)	0.0546 (17)	0.0006 (13)	−0.0104 (14)	−0.0086 (13)
C352	0.0560 (17)	0.0508 (16)	0.0369 (14)	0.0199 (13)	−0.0108 (12)	−0.0100 (12)
C353	0.0554 (18)	0.0525 (17)	0.067 (2)	−0.0013 (14)	−0.0014 (15)	−0.0078 (14)
C354	0.064 (2)	0.0564 (19)	0.078 (2)	−0.0105 (16)	−0.0048 (17)	−0.0048 (16)
C355	0.0440 (17)	0.097 (3)	0.064 (2)	−0.0023 (17)	−0.0037 (14)	−0.0123 (18)
C356	0.0541 (19)	0.099 (3)	0.061 (2)	0.009 (2)	−0.0034 (16)	−0.0163 (19)
C357	0.077 (3)	0.087 (3)	0.065 (2)	0.025 (2)	−0.0158 (18)	−0.0249 (19)
C358	0.084 (3)	0.062 (2)	0.065 (2)	0.0198 (18)	−0.0179 (18)	−0.0212 (16)
C359	0.0627 (19)	0.067 (2)	0.0421 (16)	0.0060 (15)	−0.0094 (13)	−0.0100 (14)
C360	0.0479 (15)	0.0489 (15)	0.0351 (13)	0.0018 (12)	−0.0072 (11)	−0.0094 (11)

Geometric parameters (Å, º)

C1—O1	1.233 (3)	C311—C312	1.382 (4)
C1—C2	1.472 (4)	C312—C313	1.384 (4)
C1—C11	1.478 (4)	C312—H312	0.9300
C2—C3	1.330 (4)	C313—C314	1.367 (5)
C2—H2	0.9300	C313—H313	0.9300
C3—C34	1.446 (4)	C314—C315	1.369 (5)
C3—H3	0.9300	C314—H314	0.9300
C11—C12	1.385 (4)	C315—C316	1.390 (4)
C11—C16	1.399 (4)	C315—H315	0.9300
C12—C13	1.384 (4)	C316—H316	0.9300
C12—H12	0.9300	C331—H33A	0.9600
C13—C14	1.387 (4)	C331—H33B	0.9600
C13—H13	0.9300	C331—H33C	0.9600
C14—O14	1.363 (3)	O351—C352	1.435 (3)
C14—C15	1.384 (4)	C351—C352	1.356 (4)
C15—C16	1.370 (4)	C351—C360	1.434 (4)
C15—H15	0.9300	C351—H351	0.9300
C16—H16	0.9300	C352—C353	1.391 (4)
O14—C17	1.423 (3)	C353—C354	1.382 (5)
C17—C18	1.459 (4)	C353—H353	0.9300
C17—H17A	0.9700	C354—C359	1.376 (5)
C17—H17B	0.9700	C354—H354	0.9300
C18—C19	1.161 (4)	C355—C356	1.350 (5)
C19—H19	0.9300	C355—C359	1.444 (4)
N31—C35	1.351 (3)	C355—H355	0.9300
N31—N32	1.382 (3)	C356—C357	1.397 (6)
N31—C311	1.427 (3)	C356—H356	0.9300
N32—C33	1.322 (3)	C357—C358	1.331 (5)
C33—C34	1.420 (4)	C357—H357	0.9300
C33—C331	1.494 (4)	C358—C360	1.385 (4)
C34—C35	1.378 (4)	C358—H358	0.9300
C35—O351	1.365 (3)	C359—C360	1.430 (4)
C311—C316	1.372 (4)
O1—C1—C2	121.3 (2)	C311—C312—C313	119.2 (3)
O1—C1—C11	120.0 (2)	C311—C312—H312	120.4
C2—C1—C11	118.8 (2)	C313—C312—H312	120.4
C3—C2—C1	122.2 (3)	C314—C313—C312	121.2 (3)
C3—C2—H2	118.9	C314—C313—H313	119.4
C1—C2—H2	118.9	C312—C313—H313	119.4
C2—C3—C34	127.7 (3)	C313—C314—C315	119.0 (3)
C2—C3—H3	116.2	C313—C314—H314	120.5
C34—C3—H3	116.2	C315—C314—H314	120.5
C12—C11—C16	117.6 (2)	C314—C315—C316	121.2 (3)
C12—C11—C1	119.5 (2)	C314—C315—H315	119.4
C16—C11—C1	122.8 (2)	C316—C315—H315	119.4
C13—C12—C11	121.9 (2)	C311—C316—C315	119.1 (3)
C13—C12—H12	119.0	C311—C316—H316	120.4
C11—C12—H12	119.0	C315—C316—H316	120.4
C12—C13—C14	119.1 (3)	C33—C331—H33A	109.5
C12—C13—H13	120.5	C33—C331—H33B	109.5
C14—C13—H13	120.5	H33A—C331—H33B	109.5
O14—C14—C15	115.7 (2)	C33—C331—H33C	109.5
O14—C14—C13	124.4 (2)	H33A—C331—H33C	109.5
C15—C14—C13	119.9 (2)	H33B—C331—H33C	109.5
C16—C15—C14	120.2 (2)	C35—O351—C352	118.0 (2)
C16—C15—H15	119.9	C352—C351—C360	119.9 (3)
C14—C15—H15	119.9	C352—C351—H351	120.0
C15—C16—C11	121.2 (3)	C360—C351—H351	120.0
C15—C16—H16	119.4	C351—C352—C353	122.5 (3)
C11—C16—H16	119.4	C351—C352—O351	116.0 (3)
C14—O14—C17	117.5 (2)	C353—C352—O351	121.5 (2)
O14—C17—C18	109.2 (2)	C354—C353—C352	118.9 (3)
O14—C17—H17A	109.8	C354—C353—H353	120.6
C18—C17—H17A	109.8	C352—C353—H353	120.6
O14—C17—H17B	109.8	C359—C354—C353	121.0 (3)
C18—C17—H17B	109.8	C359—C354—H354	119.5
H17A—C17—H17B	108.3	C353—C354—H354	119.5
C19—C18—C17	177.5 (4)	C356—C355—C359	118.8 (4)
C18—C19—H19	180.0	C356—C355—H355	120.6
C35—N31—N32	110.6 (2)	C359—C355—H355	120.6
C35—N31—C311	129.4 (2)	C355—C356—C357	122.7 (3)
N32—N31—C311	119.9 (2)	C355—C356—H356	118.6
C33—N32—N31	104.8 (2)	C357—C356—H356	118.6
N32—C33—C34	112.5 (2)	C358—C357—C356	119.3 (4)
N32—C33—C331	120.9 (2)	C358—C357—H357	120.4
C34—C33—C331	126.6 (2)	C356—C357—H357	120.4
C35—C34—C33	103.3 (2)	C357—C358—C360	122.4 (4)
C35—C34—C3	130.6 (2)	C357—C358—H358	118.8
C33—C34—C3	126.0 (2)	C360—C358—H358	118.8
N31—C35—O351	119.2 (2)	C354—C359—C360	120.8 (3)
N31—C35—C34	108.7 (2)	C354—C359—C355	121.6 (3)
O351—C35—C34	131.6 (2)	C360—C359—C355	117.6 (3)
C316—C311—C312	120.3 (3)	C358—C360—C359	119.3 (3)
C316—C311—N31	119.5 (2)	C358—C360—C351	123.7 (3)
C312—C311—N31	120.2 (2)	C359—C360—C351	117.0 (3)
O1—C1—C2—C3	11.5 (5)	C3—C34—C35—O351	6.6 (5)
C11—C1—C2—C3	−169.4 (3)	C35—N31—C311—C316	140.2 (3)
C1—C2—C3—C34	−179.5 (3)	N32—N31—C311—C316	−39.0 (4)
O1—C1—C11—C12	16.3 (4)	C35—N31—C311—C312	−40.9 (4)
C2—C1—C11—C12	−162.8 (3)	N32—N31—C311—C312	139.9 (3)
O1—C1—C11—C16	−162.8 (3)	C316—C311—C312—C313	−1.7 (5)
C2—C1—C11—C16	18.0 (4)	N31—C311—C312—C313	179.4 (3)
C16—C11—C12—C13	−1.1 (4)	C311—C312—C313—C314	1.3 (5)
C1—C11—C12—C13	179.7 (3)	C312—C313—C314—C315	0.1 (5)
C11—C12—C13—C14	1.3 (5)	C313—C314—C315—C316	−1.1 (5)
C12—C13—C14—O14	179.6 (3)	C312—C311—C316—C315	0.7 (4)
C12—C13—C14—C15	0.1 (5)	N31—C311—C316—C315	179.6 (3)
O14—C14—C15—C16	179.0 (3)	C314—C315—C316—C311	0.7 (5)
C13—C14—C15—C16	−1.5 (5)	N31—C35—O351—C352	118.5 (3)
C14—C15—C16—C11	1.6 (5)	C34—C35—O351—C352	−70.6 (4)
C12—C11—C16—C15	−0.3 (5)	C360—C351—C352—C353	1.1 (4)
C1—C11—C16—C15	178.8 (3)	C360—C351—C352—O351	179.0 (2)
C15—C14—O14—C17	179.1 (3)	C35—O351—C352—C351	161.8 (2)
C13—C14—O14—C17	−0.4 (4)	C35—O351—C352—C353	−20.2 (4)
C14—O14—C17—C18	−174.7 (3)	C351—C352—C353—C354	−0.5 (5)
C35—N31—N32—C33	1.2 (3)	O351—C352—C353—C354	−178.4 (3)
C311—N31—N32—C33	−179.5 (2)	C352—C353—C354—C359	−0.2 (5)
N31—N32—C33—C34	−1.3 (3)	C359—C355—C356—C357	0.2 (5)
N31—N32—C33—C331	179.5 (3)	C355—C356—C357—C358	−0.2 (6)
N32—C33—C34—C35	0.8 (3)	C356—C357—C358—C360	0.1 (5)
C331—C33—C34—C35	−180.0 (3)	C353—C354—C359—C360	0.5 (5)
N32—C33—C34—C3	−177.6 (3)	C353—C354—C359—C355	−179.4 (3)
C331—C33—C34—C3	1.6 (5)	C356—C355—C359—C354	179.8 (3)
C2—C3—C34—C35	−9.1 (5)	C356—C355—C359—C360	0.0 (5)
C2—C3—C34—C33	168.9 (3)	C357—C358—C360—C359	0.1 (5)
N32—N31—C35—O351	172.1 (2)	C357—C358—C360—C351	−179.9 (3)
C311—N31—C35—O351	−7.1 (4)	C354—C359—C360—C358	−180.0 (3)
N32—N31—C35—C34	−0.7 (3)	C355—C359—C360—C358	−0.2 (4)
C311—N31—C35—C34	−180.0 (3)	C354—C359—C360—C351	0.0 (4)
C33—C34—C35—N31	−0.1 (3)	C355—C359—C360—C351	179.9 (3)
C3—C34—C35—N31	178.3 (3)	C352—C351—C360—C358	179.2 (3)
C33—C34—C35—O351	−171.7 (3)	C352—C351—C360—C359	−0.8 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···O1^i	0.93	2.32	3.233 (5)	165
C353—H353···Cg1^ii	0.93	2.86	3.708 (3)	152

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

1-(4-Azidophenyl)-3-[3-methyl-5-(2-methylphenoxy)-1-phenyl-1H-pyrazol-4-yl]prop-2-en-1-one (IIa)

Crystal data

C26H21N5O2	Z = 2
Mr = 435.48	F(000) = 456
Triclinic, P1	Dx = 1.255 Mg m^−3
a = 9.8432 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.7441 (7) Å	Cell parameters from 4051 reflections
c = 12.3005 (7) Å	θ = 3.2–25.1°
α = 114.120 (2)°	µ = 0.08 mm^−1
β = 111.139 (2)°	T = 297 K
γ = 96.537 (2)°	Block, brown
V = 1152.06 (12) Å^3	0.20 × 0.20 × 0.18 mm

Data collection

Bruker APEXII diffractometer	4050 independent reflections
Radiation source: fine focussealed tube	2957 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
φ and ω scans	θmax = 25.1°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −11→11
Tmin = 0.868, Tmax = 0.985	k = −13→13
17379 measured reflections	l = −14→14

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)] = 0.050	w = 1/[σ^2(Fo^2) + (0.0547P)^2 + 0.4937P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.148	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.19 e Å^−3
4050 reflections	Δρmin = −0.21 e Å^−3
301 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.179 (14)
Primary atom site location: dual

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
C1	0.6025 (2)	0.4013 (2)	0.8884 (2)	0.0473 (5)
O1	0.66955 (18)	0.33036 (17)	0.9214 (2)	0.0733 (5)
C2	0.4353 (2)	0.3679 (2)	0.8333 (2)	0.0465 (5)
H2	0.3862	0.4229	0.8090	0.056*
C3	0.3533 (2)	0.2591 (2)	0.8180 (2)	0.0459 (5)
H3	0.4098	0.2111	0.8489	0.055*
C11	0.6922 (2)	0.52181 (19)	0.90264 (19)	0.0415 (5)
C12	0.8501 (2)	0.5646 (2)	0.9800 (2)	0.0462 (5)
H12	0.8940	0.5193	1.0229	0.055*
C13	0.9434 (2)	0.6725 (2)	0.9947 (2)	0.0471 (5)
H13	1.0487	0.6991	1.0463	0.057*
C14	0.8781 (2)	0.7402 (2)	0.9317 (2)	0.0480 (5)
C15	0.7212 (2)	0.7008 (2)	0.8556 (2)	0.0557 (6)
H15	0.6776	0.7473	0.8142	0.067*
C16	0.6292 (2)	0.5923 (2)	0.8413 (2)	0.0519 (5)
H16	0.5239	0.5662	0.7900	0.062*
N14	0.9637 (2)	0.85203 (19)	0.9401 (2)	0.0656 (6)
N15	1.1040 (3)	0.8907 (2)	1.0131 (2)	0.0693 (6)
N16	1.2312 (3)	0.9373 (3)	1.0751 (3)	0.1029 (10)
N31	−0.06215 (19)	0.16164 (16)	0.66089 (17)	0.0471 (4)
N32	−0.0398 (2)	0.05926 (17)	0.68563 (18)	0.0511 (5)
C33	0.1109 (2)	0.0864 (2)	0.7460 (2)	0.0469 (5)
C34	0.1897 (2)	0.20522 (19)	0.7604 (2)	0.0433 (5)
C35	0.0727 (2)	0.24912 (19)	0.7052 (2)	0.0442 (5)
C311	−0.2141 (2)	0.1559 (2)	0.5825 (2)	0.0471 (5)
C312	−0.2664 (3)	0.2627 (2)	0.6210 (3)	0.0611 (6)
H312	−0.2034	0.3406	0.6988	0.073*
C313	−0.4142 (3)	0.2524 (3)	0.5418 (3)	0.0711 (7)
H313	−0.4506	0.3239	0.5667	0.085*
C314	−0.5075 (3)	0.1371 (3)	0.4269 (3)	0.0735 (7)
H314	−0.6063	0.1312	0.3741	0.088*
C315	−0.4550 (3)	0.0308 (3)	0.3900 (3)	0.0719 (7)
H315	−0.5184	−0.0472	0.3124	0.086*
C316	−0.3082 (3)	0.0397 (2)	0.4679 (2)	0.0578 (6)
H316	−0.2728	−0.0324	0.4433	0.069*
C331	0.1796 (3)	−0.0017 (2)	0.7929 (3)	0.0645 (6)
H33A	0.1019	−0.0622	0.7896	0.097*
H33B	0.2587	0.0498	0.8829	0.097*
H33C	0.2225	−0.0495	0.7365	0.097*
O351	0.07382 (17)	0.36198 (13)	0.69897 (15)	0.0522 (4)
C351	0.1292 (2)	0.38472 (19)	0.6168 (2)	0.0434 (5)
C352	0.1738 (2)	0.5152 (2)	0.6479 (2)	0.0522 (5)
C353	0.2282 (3)	0.5403 (3)	0.5678 (3)	0.0690 (7)
H353	0.2599	0.6264	0.5855	0.083*
C354	0.2367 (3)	0.4418 (3)	0.4633 (3)	0.0780 (8)
H354	0.2741	0.4618	0.4116	0.094*
C355	0.1900 (3)	0.3135 (3)	0.4344 (3)	0.0699 (7)
H355	0.1952	0.2469	0.3630	0.084*
C356	0.1353 (3)	0.2839 (2)	0.5119 (2)	0.0547 (6)
H356	0.1032	0.1976	0.4934	0.066*
C357	0.1657 (4)	0.6222 (2)	0.7625 (3)	0.0777 (8)
H35A	0.1876	0.7031	0.7608	0.116*
H35B	0.2393	0.6314	0.8446	0.116*
H35C	0.0649	0.6010	0.7559	0.116*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0414 (11)	0.0494 (12)	0.0507 (12)	0.0123 (9)	0.0182 (9)	0.0266 (10)
O1	0.0471 (9)	0.0702 (11)	0.1105 (14)	0.0170 (8)	0.0231 (9)	0.0615 (11)
C2	0.0378 (11)	0.0456 (11)	0.0520 (12)	0.0110 (9)	0.0178 (9)	0.0227 (9)
C3	0.0441 (11)	0.0436 (11)	0.0474 (11)	0.0122 (9)	0.0214 (9)	0.0194 (9)
C11	0.0362 (10)	0.0439 (11)	0.0414 (10)	0.0110 (8)	0.0166 (8)	0.0192 (9)
C12	0.0382 (11)	0.0490 (12)	0.0531 (12)	0.0147 (9)	0.0193 (9)	0.0270 (10)
C13	0.0364 (10)	0.0470 (11)	0.0531 (12)	0.0111 (9)	0.0171 (9)	0.0231 (10)
C14	0.0467 (12)	0.0430 (11)	0.0500 (12)	0.0074 (9)	0.0213 (9)	0.0207 (9)
C15	0.0478 (12)	0.0569 (13)	0.0614 (13)	0.0119 (10)	0.0157 (10)	0.0366 (11)
C16	0.0375 (11)	0.0573 (13)	0.0544 (12)	0.0091 (9)	0.0127 (9)	0.0298 (11)
N14	0.0517 (12)	0.0558 (12)	0.0775 (14)	0.0002 (9)	0.0136 (10)	0.0397 (11)
N15	0.0585 (14)	0.0588 (13)	0.0799 (14)	0.0032 (10)	0.0187 (12)	0.0388 (11)
N16	0.0565 (15)	0.0956 (19)	0.130 (2)	−0.0054 (13)	0.0099 (15)	0.0668 (18)
N31	0.0417 (9)	0.0424 (9)	0.0551 (10)	0.0076 (7)	0.0203 (8)	0.0245 (8)
N32	0.0485 (11)	0.0443 (10)	0.0612 (11)	0.0080 (8)	0.0232 (9)	0.0291 (9)
C33	0.0492 (12)	0.0416 (11)	0.0514 (12)	0.0091 (9)	0.0252 (10)	0.0228 (9)
C34	0.0422 (11)	0.0403 (10)	0.0463 (11)	0.0090 (8)	0.0219 (9)	0.0191 (9)
C35	0.0463 (11)	0.0375 (10)	0.0512 (11)	0.0100 (9)	0.0256 (9)	0.0212 (9)
C311	0.0418 (11)	0.0519 (12)	0.0499 (11)	0.0116 (9)	0.0236 (9)	0.0246 (10)
C312	0.0542 (14)	0.0539 (14)	0.0674 (15)	0.0149 (11)	0.0269 (12)	0.0235 (12)
C313	0.0613 (16)	0.0702 (17)	0.0894 (19)	0.0309 (13)	0.0369 (15)	0.0399 (15)
C314	0.0505 (14)	0.090 (2)	0.0758 (17)	0.0230 (14)	0.0233 (13)	0.0408 (16)
C315	0.0518 (14)	0.0762 (18)	0.0609 (15)	0.0108 (13)	0.0165 (12)	0.0197 (13)
C316	0.0495 (13)	0.0558 (13)	0.0584 (13)	0.0142 (10)	0.0248 (11)	0.0193 (11)
C331	0.0663 (15)	0.0588 (14)	0.0765 (16)	0.0175 (12)	0.0304 (13)	0.0418 (13)
O351	0.0583 (9)	0.0427 (8)	0.0694 (10)	0.0185 (7)	0.0374 (8)	0.0310 (7)
C351	0.0370 (10)	0.0452 (11)	0.0485 (11)	0.0107 (8)	0.0155 (9)	0.0269 (9)
C352	0.0491 (12)	0.0476 (12)	0.0575 (13)	0.0125 (10)	0.0163 (10)	0.0307 (10)
C353	0.0742 (17)	0.0632 (16)	0.0749 (17)	0.0127 (13)	0.0264 (14)	0.0464 (14)
C354	0.089 (2)	0.091 (2)	0.0798 (18)	0.0248 (16)	0.0440 (16)	0.0589 (17)
C355	0.0818 (18)	0.0828 (18)	0.0608 (15)	0.0339 (15)	0.0380 (14)	0.0411 (14)
C356	0.0580 (13)	0.0497 (12)	0.0547 (13)	0.0166 (10)	0.0219 (11)	0.0267 (11)
C357	0.104 (2)	0.0467 (14)	0.0809 (18)	0.0248 (14)	0.0384 (16)	0.0318 (13)

Geometric parameters (Å, º)

C1—O1	1.226 (3)	C311—C316	1.380 (3)
C1—C2	1.468 (3)	C312—C313	1.386 (3)
C1—C11	1.488 (3)	C312—H312	0.9300
C2—C3	1.334 (3)	C313—C314	1.375 (4)
C2—H2	0.9300	C313—H313	0.9300
C3—C34	1.440 (3)	C314—C315	1.373 (4)
C3—H3	0.9300	C314—H314	0.9300
C11—C16	1.389 (3)	C315—C316	1.379 (3)
C11—C12	1.392 (3)	C315—H315	0.9300
C12—C13	1.382 (3)	C316—H316	0.9300
C12—H12	0.9300	C331—H33A	0.9600
C13—C14	1.380 (3)	C331—H33B	0.9600
C13—H13	0.9300	C331—H33C	0.9600
C14—C15	1.384 (3)	O351—C351	1.405 (2)
C14—N14	1.422 (3)	C351—C356	1.377 (3)
C15—C16	1.383 (3)	C351—C352	1.391 (3)
C15—H15	0.9300	C352—C353	1.389 (3)
C16—H16	0.9300	C352—C357	1.493 (3)
N14—N15	1.245 (3)	C353—C354	1.372 (4)
N15—N16	1.124 (3)	C353—H353	0.9300
N31—C35	1.351 (3)	C354—C355	1.377 (4)
N31—N32	1.378 (2)	C354—H354	0.9300
N31—C311	1.433 (3)	C355—C356	1.385 (3)
N32—C33	1.326 (3)	C355—H355	0.9300
C33—C34	1.426 (3)	C356—H356	0.9300
C33—C331	1.493 (3)	C357—H35A	0.9600
C34—C35	1.382 (3)	C357—H35B	0.9600
C35—O351	1.358 (2)	C357—H35C	0.9600
C311—C312	1.379 (3)
O1—C1—C2	120.91 (19)	C311—C312—H312	120.5
O1—C1—C11	119.34 (19)	C313—C312—H312	120.5
C2—C1—C11	119.74 (18)	C314—C313—C312	120.5 (2)
C3—C2—C1	120.4 (2)	C314—C313—H313	119.8
C3—C2—H2	119.8	C312—C313—H313	119.8
C1—C2—H2	119.8	C315—C314—C313	120.1 (2)
C2—C3—C34	129.2 (2)	C315—C314—H314	119.9
C2—C3—H3	115.4	C313—C314—H314	119.9
C34—C3—H3	115.4	C314—C315—C316	120.0 (2)
C16—C11—C12	118.03 (19)	C314—C315—H315	120.0
C16—C11—C1	124.29 (18)	C316—C315—H315	120.0
C12—C11—C1	117.66 (18)	C315—C316—C311	119.9 (2)
C13—C12—C11	121.75 (19)	C315—C316—H316	120.1
C13—C12—H12	119.1	C311—C316—H316	120.1
C11—C12—H12	119.1	C33—C331—H33A	109.5
C14—C13—C12	119.10 (19)	C33—C331—H33B	109.5
C14—C13—H13	120.5	H33A—C331—H33B	109.5
C12—C13—H13	120.5	C33—C331—H33C	109.5
C13—C14—C15	120.35 (19)	H33A—C331—H33C	109.5
C13—C14—N14	123.5 (2)	H33B—C331—H33C	109.5
C15—C14—N14	116.1 (2)	C35—O351—C351	119.16 (15)
C16—C15—C14	120.0 (2)	C356—C351—C352	123.0 (2)
C16—C15—H15	120.0	C356—C351—O351	121.83 (18)
C14—C15—H15	120.0	C352—C351—O351	115.11 (18)
C15—C16—C11	120.80 (19)	C353—C352—C351	116.3 (2)
C15—C16—H16	119.6	C353—C352—C357	122.0 (2)
C11—C16—H16	119.6	C351—C352—C357	121.7 (2)
N15—N14—C14	116.1 (2)	C354—C353—C352	121.9 (2)
N16—N15—N14	171.8 (3)	C354—C353—H353	119.1
C35—N31—N32	111.11 (17)	C352—C353—H353	119.1
C35—N31—C311	129.06 (18)	C353—C354—C355	120.3 (2)
N32—N31—C311	119.38 (16)	C353—C354—H354	119.8
C33—N32—N31	104.82 (16)	C355—C354—H354	119.8
N32—C33—C34	112.21 (18)	C354—C355—C356	119.8 (3)
N32—C33—C331	120.41 (18)	C354—C355—H355	120.1
C34—C33—C331	127.4 (2)	C356—C355—H355	120.1
C35—C34—C33	103.40 (17)	C351—C356—C355	118.7 (2)
C35—C34—C3	131.01 (19)	C351—C356—H356	120.7
C33—C34—C3	125.58 (19)	C355—C356—H356	120.7
N31—C35—O351	119.52 (18)	C352—C357—H35A	109.5
N31—C35—C34	108.45 (18)	C352—C357—H35B	109.5
O351—C35—C34	131.82 (18)	H35A—C357—H35B	109.5
C312—C311—C316	120.5 (2)	C352—C357—H35C	109.5
C312—C311—N31	121.14 (19)	H35A—C357—H35C	109.5
C316—C311—N31	118.35 (19)	H35B—C357—H35C	109.5
C311—C312—C313	119.0 (2)
O1—C1—C2—C3	−0.1 (3)	C311—N31—C35—C34	−171.57 (19)
C11—C1—C2—C3	178.86 (19)	C33—C34—C35—N31	−0.9 (2)
C1—C2—C3—C34	−176.53 (19)	C3—C34—C35—N31	178.1 (2)
O1—C1—C11—C16	164.2 (2)	C33—C34—C35—O351	173.7 (2)
C2—C1—C11—C16	−14.8 (3)	C3—C34—C35—O351	−7.3 (4)
O1—C1—C11—C12	−14.2 (3)	C35—N31—C311—C312	−53.4 (3)
C2—C1—C11—C12	166.82 (18)	N32—N31—C311—C312	135.1 (2)
C16—C11—C12—C13	−1.0 (3)	C35—N31—C311—C316	127.5 (2)
C1—C11—C12—C13	177.49 (19)	N32—N31—C311—C316	−44.0 (3)
C11—C12—C13—C14	0.4 (3)	C316—C311—C312—C313	−0.9 (4)
C12—C13—C14—C15	0.4 (3)	N31—C311—C312—C313	−180.0 (2)
C12—C13—C14—N14	−179.8 (2)	C311—C312—C313—C314	0.2 (4)
C13—C14—C15—C16	−0.7 (3)	C312—C313—C314—C315	0.4 (4)
N14—C14—C15—C16	179.5 (2)	C313—C314—C315—C316	−0.3 (4)
C14—C15—C16—C11	0.1 (4)	C314—C315—C316—C311	−0.4 (4)
C12—C11—C16—C15	0.7 (3)	C312—C311—C316—C315	1.0 (3)
C1—C11—C16—C15	−177.7 (2)	N31—C311—C316—C315	−179.9 (2)
C13—C14—N14—N15	−2.7 (3)	N31—C35—O351—C351	−115.8 (2)
C15—C14—N14—N15	177.1 (2)	C34—C35—O351—C351	70.1 (3)
C35—N31—N32—C33	0.1 (2)	C35—O351—C351—C356	21.6 (3)
C311—N31—N32—C33	173.08 (17)	C35—O351—C351—C352	−159.61 (18)
N31—N32—C33—C34	−0.7 (2)	C356—C351—C352—C353	−1.0 (3)
N31—N32—C33—C331	177.90 (19)	O351—C351—C352—C353	−179.69 (19)
N32—C33—C34—C35	1.0 (2)	C356—C351—C352—C357	180.0 (2)
C331—C33—C34—C35	−177.5 (2)	O351—C351—C352—C357	1.3 (3)
N32—C33—C34—C3	−178.03 (18)	C351—C352—C353—C354	0.4 (4)
C331—C33—C34—C3	3.5 (3)	C357—C352—C353—C354	179.4 (3)
C2—C3—C34—C35	0.2 (4)	C352—C353—C354—C355	0.3 (4)
C2—C3—C34—C33	179.0 (2)	C353—C354—C355—C356	−0.4 (4)
N32—N31—C35—O351	−174.87 (17)	C352—C351—C356—C355	0.8 (3)
C311—N31—C35—O351	13.1 (3)	O351—C351—C356—C355	179.5 (2)
N32—N31—C35—C34	0.5 (2)	C354—C355—C356—C351	−0.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C357—H35B···O1^i	0.96	2.51	3.396 (4)	154

Symmetry code: (i) −x+1, −y+1, −z+2.

1-(4-Azidophenyl)-3-[5-(2,4-dichlorophenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl]prop-2-en-1-one (IId)

Crystal data

C25H17Cl2N5O2	F(000) = 2016
Mr = 490.33	Dx = 1.377 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 28.1916 (17) Å	Cell parameters from 4176 reflections
b = 8.0537 (5) Å	θ = 2.9–25.0°
c = 22.0446 (12) Å	µ = 0.31 mm^−1
β = 109.070 (1)°	T = 297 K
V = 4730.5 (5) Å^3	Block, colourless
Z = 8	0.18 × 0.15 × 0.15 mm

Data collection

Bruker APEXII diffractometer	4174 independent reflections
Radiation source: fine focussealed tube	3181 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
φ and ω scans	θmax = 25.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −33→33
Tmin = 0.881, Tmax = 0.955	k = −9→9
31508 measured reflections	l = −26→21

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)] = 0.086	w = 1/[σ^2(Fo^2) + (0.0265P)^2 + 10.5248P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.155	(Δ/σ)max < 0.001
S = 1.36	Δρmax = 0.21 e Å^−3
4174 reflections	Δρmin = −0.23 e Å^−3
382 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
291 restraints	Extinction coefficient: 0.0018 (3)
Primary atom site location: dual

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	0.42395 (14)	0.7441 (5)	0.5060 (2)	0.0497 (10)
O1	0.42708 (11)	0.8068 (4)	0.55744 (16)	0.0731 (10)
C2	0.46893 (14)	0.7129 (5)	0.48791 (19)	0.0509 (10)
H2	0.4658	0.6524	0.4509	0.061*
C3	0.51394 (14)	0.7686 (5)	0.52294 (19)	0.0505 (10)
H3	0.5154	0.8257	0.5602	0.061*
C11	0.37362 (14)	0.6992 (5)	0.45998 (19)	0.0472 (10)
C12	0.33110 (15)	0.7460 (6)	0.4740 (2)	0.0637 (12)
H12	0.3346	0.8036	0.5118	0.076*
C13	0.28398 (17)	0.7089 (7)	0.4332 (2)	0.0741 (14)
H13	0.2558	0.7415	0.4433	0.089*
C14	0.27855 (15)	0.6239 (6)	0.3778 (2)	0.0624 (12)
C15	0.31991 (16)	0.5748 (6)	0.3626 (2)	0.0665 (13)
H15	0.3162	0.5164	0.3250	0.080*
C16	0.36695 (15)	0.6129 (6)	0.4038 (2)	0.0616 (12)
H16	0.3950	0.5796	0.3935	0.074*
N14	0.22805 (15)	0.5915 (6)	0.3381 (2)	0.0911 (15)
N15	0.22323 (16)	0.4999 (7)	0.2916 (3)	0.0912 (15)
N16	0.2133 (2)	0.4157 (9)	0.2483 (3)	0.128 (2)
N31	0.61980 (11)	0.6957 (4)	0.46689 (15)	0.0498 (9)
N32	0.64431 (12)	0.7692 (5)	0.52519 (15)	0.0577 (10)
C33	0.60890 (15)	0.8028 (5)	0.55055 (19)	0.0539 (11)
C34	0.56086 (13)	0.7514 (5)	0.51031 (18)	0.0455 (9)
C35	0.56997 (13)	0.6852 (5)	0.45798 (18)	0.0449 (9)
C311	0.64806 (14)	0.6459 (5)	0.42690 (18)	0.0489 (10)
C312	0.63370 (15)	0.5118 (6)	0.3859 (2)	0.0576 (11)
H312	0.6047	0.4527	0.3832	0.069*
C313	0.66276 (18)	0.4666 (6)	0.3491 (2)	0.0702 (13)
H313	0.6530	0.3781	0.3207	0.084*
C314	0.70616 (19)	0.5516 (7)	0.3541 (2)	0.0782 (15)
H314	0.7257	0.5199	0.3293	0.094*
C315	0.72076 (17)	0.6827 (7)	0.3955 (3)	0.0784 (15)
H315	0.7505	0.7383	0.3993	0.094*
C316	0.69143 (16)	0.7326 (6)	0.4316 (2)	0.0672 (13)
H316	0.7008	0.8237	0.4588	0.081*
C331	0.62281 (17)	0.8821 (7)	0.6150 (2)	0.0720 (14)
H33A	0.6193	0.8029	0.6457	0.108*
H33B	0.6011	0.9752	0.6133	0.108*
H33C	0.6570	0.9194	0.6274	0.108*
O351	0.53813 (9)	0.6158 (3)	0.40327 (12)	0.0483 (7)	0.55 (4)
C351	0.5093 (7)	0.7253 (10)	0.3559 (10)	0.030 (5)	0.55 (4)
C352	0.4689 (8)	0.6575 (11)	0.3090 (11)	0.038 (5)	0.55 (4)
Cl52	0.4590 (5)	0.4465 (11)	0.3077 (7)	0.118 (4)	0.55 (4)
C353	0.4349 (9)	0.7567 (14)	0.2647 (12)	0.048 (6)	0.55 (4)
H353	0.4104	0.7108	0.2295	0.058*	0.55 (4)
C354	0.4384 (7)	0.9280 (13)	0.2743 (10)	0.039 (5)	0.55 (4)
Cl54	0.3988 (2)	1.0506 (7)	0.2131 (2)	0.067 (3)	0.55 (4)
C355	0.4787 (8)	0.9973 (14)	0.3206 (11)	0.043 (5)	0.55 (4)
H355	0.4832	1.1119	0.3225	0.051*	0.55 (4)
C356	0.5125 (8)	0.8960 (12)	0.3640 (12)	0.047 (6)	0.55 (4)
H356	0.5374	0.9420	0.3987	0.056*	0.55 (4)
O451	0.53813 (9)	0.6158 (3)	0.40327 (12)	0.0483 (7)	0.45 (4)
C451	0.5023 (8)	0.7239 (13)	0.3633 (11)	0.031 (5)	0.45 (4)
C452	0.4619 (10)	0.6533 (14)	0.3172 (14)	0.040 (7)	0.45 (4)
Cl62	0.4539 (3)	0.4410 (9)	0.3133 (5)	0.058 (3)	0.45 (4)
C453	0.4287 (11)	0.7504 (17)	0.2708 (15)	0.047 (6)	0.45 (4)
H453	0.3980	0.7085	0.2450	0.056*	0.45 (4)
C454	0.4429 (9)	0.913 (2)	0.2639 (13)	0.050 (7)	0.45 (4)
Cl64	0.3977 (4)	1.0402 (17)	0.2112 (5)	0.128 (6)	0.45 (4)
C455	0.4832 (9)	0.9854 (19)	0.3095 (14)	0.045 (6)	0.45 (4)
H455	0.4889	1.0989	0.3086	0.054*	0.45 (4)
C456	0.5150 (8)	0.8875 (16)	0.3564 (13)	0.036 (5)	0.45 (4)
H456	0.5450	0.9310	0.3835	0.043*	0.45 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.048 (2)	0.045 (2)	0.056 (3)	−0.0079 (19)	0.016 (2)	−0.003 (2)
O1	0.0606 (19)	0.091 (3)	0.072 (2)	−0.0197 (17)	0.0267 (16)	−0.0303 (19)
C2	0.048 (2)	0.056 (3)	0.047 (2)	−0.0035 (19)	0.0118 (19)	−0.003 (2)
C3	0.051 (2)	0.053 (2)	0.045 (2)	−0.004 (2)	0.0127 (19)	−0.0012 (19)
C11	0.048 (2)	0.043 (2)	0.051 (2)	0.0000 (18)	0.0167 (19)	0.0025 (19)
C12	0.051 (3)	0.079 (3)	0.061 (3)	0.006 (2)	0.018 (2)	−0.008 (2)
C13	0.049 (3)	0.100 (4)	0.071 (3)	0.011 (3)	0.017 (2)	−0.004 (3)
C14	0.045 (2)	0.069 (3)	0.065 (3)	−0.001 (2)	0.006 (2)	0.007 (2)
C15	0.051 (3)	0.079 (3)	0.063 (3)	−0.001 (2)	0.011 (2)	−0.016 (3)
C16	0.044 (2)	0.072 (3)	0.070 (3)	−0.002 (2)	0.019 (2)	−0.010 (3)
N14	0.053 (3)	0.113 (4)	0.091 (3)	0.001 (2)	0.003 (2)	−0.017 (3)
N15	0.061 (3)	0.122 (4)	0.077 (3)	−0.009 (3)	0.004 (3)	−0.003 (3)
N16	0.105 (4)	0.175 (6)	0.087 (4)	−0.023 (4)	0.009 (3)	−0.030 (4)
N31	0.0388 (18)	0.061 (2)	0.0452 (19)	−0.0027 (16)	0.0082 (15)	0.0027 (16)
N32	0.0398 (18)	0.081 (3)	0.044 (2)	−0.0093 (18)	0.0023 (15)	0.0002 (18)
C33	0.045 (2)	0.066 (3)	0.046 (2)	−0.008 (2)	0.0093 (19)	0.002 (2)
C34	0.038 (2)	0.049 (2)	0.044 (2)	−0.0037 (18)	0.0057 (17)	0.0053 (19)
C35	0.037 (2)	0.047 (2)	0.044 (2)	−0.0005 (17)	0.0041 (17)	0.0081 (19)
C311	0.038 (2)	0.057 (3)	0.046 (2)	0.0033 (19)	0.0063 (18)	0.012 (2)
C312	0.047 (2)	0.059 (3)	0.065 (3)	0.004 (2)	0.016 (2)	0.010 (2)
C313	0.063 (3)	0.074 (3)	0.072 (3)	0.015 (3)	0.020 (3)	−0.002 (3)
C314	0.065 (3)	0.103 (4)	0.073 (3)	0.016 (3)	0.032 (3)	0.006 (3)
C315	0.052 (3)	0.105 (4)	0.081 (4)	−0.010 (3)	0.025 (3)	0.006 (3)
C316	0.051 (3)	0.083 (3)	0.064 (3)	−0.007 (2)	0.015 (2)	−0.001 (3)
C331	0.057 (3)	0.103 (4)	0.050 (3)	−0.017 (3)	0.010 (2)	−0.012 (3)
O351	0.0413 (14)	0.0446 (15)	0.0480 (16)	−0.0012 (12)	−0.0005 (12)	−0.0026 (12)
C351	0.019 (5)	0.035 (6)	0.043 (8)	−0.004 (4)	0.018 (5)	−0.006 (4)
C352	0.035 (6)	0.041 (6)	0.043 (8)	0.001 (4)	0.017 (7)	−0.008 (5)
Cl52	0.132 (7)	0.064 (4)	0.115 (6)	−0.019 (4)	−0.018 (4)	−0.012 (4)
C353	0.035 (7)	0.067 (9)	0.039 (8)	−0.011 (6)	0.008 (6)	−0.013 (6)
C354	0.042 (6)	0.046 (6)	0.030 (7)	0.028 (5)	0.013 (6)	0.010 (5)
Cl54	0.058 (3)	0.068 (4)	0.051 (3)	0.033 (2)	−0.014 (3)	0.020 (2)
C355	0.046 (6)	0.045 (6)	0.039 (7)	0.009 (5)	0.017 (7)	−0.007 (5)
C356	0.052 (10)	0.049 (8)	0.035 (7)	0.000 (6)	0.010 (7)	−0.016 (6)
O451	0.0413 (14)	0.0446 (15)	0.0480 (16)	−0.0012 (12)	−0.0005 (12)	−0.0026 (12)
C451	0.026 (8)	0.057 (9)	0.018 (5)	0.000 (5)	0.017 (6)	0.000 (5)
C452	0.040 (9)	0.050 (8)	0.037 (8)	−0.011 (6)	0.021 (7)	−0.006 (6)
Cl62	0.052 (4)	0.036 (3)	0.073 (4)	−0.012 (2)	0.001 (2)	−0.013 (2)
C453	0.035 (8)	0.067 (10)	0.039 (8)	0.002 (7)	0.011 (8)	0.000 (7)
C454	0.042 (8)	0.077 (11)	0.036 (9)	0.005 (8)	0.020 (6)	−0.008 (7)
Cl64	0.103 (8)	0.150 (10)	0.130 (9)	0.036 (6)	0.037 (7)	0.023 (6)
C455	0.057 (9)	0.041 (8)	0.047 (10)	0.009 (6)	0.032 (7)	0.003 (7)
C456	0.020 (7)	0.047 (10)	0.043 (10)	−0.009 (7)	0.012 (6)	0.002 (8)

Geometric parameters (Å, º)

C1—O1	1.218 (5)	C313—H313	0.9300
C1—C2	1.470 (5)	C314—C315	1.367 (7)
C1—C11	1.494 (5)	C314—H314	0.9300
C2—C3	1.329 (5)	C315—C316	1.382 (6)
C2—H2	0.9300	C315—H315	0.9300
C3—C34	1.445 (5)	C316—H316	0.9300
C3—H3	0.9300	C331—H33A	0.9600
C11—C16	1.378 (6)	C331—H33B	0.9600
C11—C12	1.385 (5)	C331—H33C	0.9600
C12—C13	1.372 (6)	O351—C351	1.405 (7)
C12—H12	0.9300	C351—C352	1.377 (7)
C13—C14	1.365 (6)	C351—C356	1.385 (11)
C13—H13	0.9300	C352—C353	1.377 (8)
C14—C15	1.372 (6)	C352—Cl52	1.721 (7)
C14—N14	1.431 (6)	C353—C354	1.395 (13)
C15—C16	1.375 (6)	C353—H353	0.9300
C15—H15	0.9300	C354—C355	1.374 (8)
C16—H16	0.9300	C354—Cl54	1.748 (6)
N14—N15	1.233 (7)	C355—C356	1.375 (8)
N15—N16	1.128 (7)	C355—H355	0.9300
N31—C35	1.356 (5)	C356—H356	0.9300
N31—N32	1.378 (4)	C451—C452	1.378 (8)
N31—C311	1.425 (5)	C451—C456	1.387 (12)
N32—C33	1.322 (5)	C452—C453	1.381 (8)
C33—C34	1.417 (5)	C452—Cl62	1.723 (7)
C33—C331	1.488 (6)	C453—C454	1.394 (15)
C34—C35	1.369 (5)	C453—H453	0.9300
C35—O351	1.366 (4)	C454—C455	1.376 (9)
C311—C312	1.381 (6)	C454—Cl64	1.746 (8)
C311—C316	1.382 (6)	C455—C456	1.373 (8)
C312—C313	1.378 (6)	C455—H455	0.9300
C312—H312	0.9300	C456—H456	0.9300
C313—C314	1.374 (7)
O1—C1—C2	121.1 (4)	C315—C314—C313	120.3 (5)
O1—C1—C11	119.8 (4)	C315—C314—H314	119.8
C2—C1—C11	119.1 (4)	C313—C314—H314	119.8
C3—C2—C1	121.9 (4)	C314—C315—C316	120.1 (5)
C3—C2—H2	119.0	C314—C315—H315	119.9
C1—C2—H2	119.0	C316—C315—H315	119.9
C2—C3—C34	128.0 (4)	C315—C316—C311	119.4 (5)
C2—C3—H3	116.0	C315—C316—H316	120.3
C34—C3—H3	116.0	C311—C316—H316	120.3
C16—C11—C12	117.7 (4)	C33—C331—H33A	109.5
C16—C11—C1	123.5 (4)	C33—C331—H33B	109.5
C12—C11—C1	118.8 (4)	H33A—C331—H33B	109.5
C13—C12—C11	121.2 (4)	C33—C331—H33C	109.5
C13—C12—H12	119.4	H33A—C331—H33C	109.5
C11—C12—H12	119.4	H33B—C331—H33C	109.5
C14—C13—C12	119.8 (4)	C35—O351—C351	117.0 (5)
C14—C13—H13	120.1	C352—C351—C356	119.5 (7)
C12—C13—H13	120.1	C352—C351—O351	116.5 (6)
C13—C14—C15	120.5 (4)	C356—C351—O351	122.0 (9)
C13—C14—N14	115.9 (4)	C351—C352—C353	121.1 (6)
C15—C14—N14	123.6 (5)	C351—C352—Cl52	119.6 (6)
C14—C15—C16	119.2 (4)	C353—C352—Cl52	119.3 (6)
C14—C15—H15	120.4	C352—C353—C354	117.9 (8)
C16—C15—H15	120.4	C352—C353—H353	121.1
C15—C16—C11	121.6 (4)	C354—C353—H353	121.1
C15—C16—H16	119.2	C355—C354—C353	121.0 (8)
C11—C16—H16	119.2	C355—C354—Cl54	120.5 (6)
N15—N14—C14	115.8 (5)	C353—C354—Cl54	116.5 (8)
N16—N15—N14	172.3 (6)	C354—C355—C356	119.5 (7)
C35—N31—N32	110.0 (3)	C354—C355—H355	120.3
C35—N31—C311	130.9 (3)	C356—C355—H355	120.3
N32—N31—C311	119.1 (3)	C355—C356—C351	119.9 (8)
C33—N32—N31	105.3 (3)	C355—C356—H356	120.0
N32—C33—C34	112.0 (4)	C351—C356—H356	120.0
N32—C33—C331	119.4 (4)	C452—C451—C456	119.5 (9)
C34—C33—C331	128.5 (4)	C451—C452—C453	120.6 (8)
C35—C34—C33	103.7 (3)	C451—C452—Cl62	120.6 (7)
C35—C34—C3	129.5 (3)	C453—C452—Cl62	118.6 (7)
C33—C34—C3	126.8 (4)	C452—C453—C454	117.7 (11)
N31—C35—O351	120.3 (3)	C452—C453—H453	121.1
N31—C35—C34	108.9 (3)	C454—C453—H453	121.1
O351—C35—C34	130.8 (3)	C455—C454—C453	121.0 (10)
C312—C311—C316	120.5 (4)	C455—C454—Cl64	119.3 (9)
C312—C311—N31	121.4 (4)	C453—C454—Cl64	116.8 (11)
C316—C311—N31	118.1 (4)	C456—C455—C454	119.2 (8)
C313—C312—C311	119.2 (4)	C456—C455—H455	120.4
C313—C312—H312	120.4	C454—C455—H455	120.4
C311—C312—H312	120.4	C455—C456—C451	120.0 (9)
C314—C313—C312	120.4 (5)	C455—C456—H456	120.0
C314—C313—H313	119.8	C451—C456—H456	120.0
C312—C313—H313	119.8
O1—C1—C2—C3	−8.0 (6)	N32—N31—C311—C312	149.6 (4)
C11—C1—C2—C3	171.4 (4)	C35—N31—C311—C316	151.0 (4)
C1—C2—C3—C34	−178.2 (4)	N32—N31—C311—C316	−28.4 (5)
O1—C1—C11—C16	−173.2 (4)	C316—C311—C312—C313	−0.9 (6)
C2—C1—C11—C16	7.4 (6)	N31—C311—C312—C313	−178.8 (4)
O1—C1—C11—C12	6.7 (6)	C311—C312—C313—C314	1.5 (7)
C2—C1—C11—C12	−172.7 (4)	C312—C313—C314—C315	−0.4 (8)
C16—C11—C12—C13	−0.5 (7)	C313—C314—C315—C316	−1.3 (8)
C1—C11—C12—C13	179.6 (4)	C314—C315—C316—C311	1.9 (7)
C11—C12—C13—C14	0.2 (8)	C312—C311—C316—C315	−0.8 (7)
C12—C13—C14—C15	0.2 (8)	N31—C311—C316—C315	177.2 (4)
C12—C13—C14—N14	−179.7 (5)	N31—C35—O351—C351	−102.1 (15)
C13—C14—C15—C16	−0.3 (8)	C34—C35—O351—C351	78.3 (16)
N14—C14—C15—C16	179.6 (5)	C35—O351—C351—C352	−164 (2)
C14—C15—C16—C11	0.0 (7)	C35—O351—C351—C356	0 (4)
C12—C11—C16—C15	0.4 (7)	C356—C351—C352—C353	8 (5)
C1—C11—C16—C15	−179.7 (4)	O351—C351—C352—C353	172 (3)
C13—C14—N14—N15	−172.6 (5)	C356—C351—C352—Cl52	−169 (3)
C15—C14—N14—N15	7.5 (8)	O351—C351—C352—Cl52	−4 (4)
C35—N31—N32—C33	−0.3 (4)	C351—C352—C353—C354	−9 (5)
C311—N31—N32—C33	179.3 (4)	Cl52—C352—C353—C354	168 (3)
N31—N32—C33—C34	0.6 (5)	C352—C353—C354—C355	10 (5)
N31—N32—C33—C331	179.2 (4)	C352—C353—C354—Cl54	174 (3)
N32—C33—C34—C35	−0.6 (5)	C353—C354—C355—C356	−9 (5)
C331—C33—C34—C35	−179.1 (5)	Cl54—C354—C355—C356	−173 (3)
N32—C33—C34—C3	180.0 (4)	C354—C355—C356—C351	8 (5)
C331—C33—C34—C3	1.5 (7)	C352—C351—C356—C355	−8 (5)
C2—C3—C34—C35	5.1 (7)	O351—C351—C356—C355	−171 (3)
C2—C3—C34—C33	−175.7 (4)	C456—C451—C452—C453	−11 (6)
N32—N31—C35—O351	−179.8 (3)	C456—C451—C452—Cl62	164 (3)
C311—N31—C35—O351	0.7 (6)	C451—C452—C453—C454	13 (6)
N32—N31—C35—C34	−0.1 (5)	Cl62—C452—C453—C454	−163 (4)
C311—N31—C35—C34	−179.6 (4)	C452—C453—C454—C455	−13 (6)
C33—C34—C35—N31	0.4 (4)	C452—C453—C454—Cl64	−173 (3)
C3—C34—C35—N31	179.8 (4)	C453—C454—C455—C456	11 (6)
C33—C34—C35—O351	−179.9 (4)	Cl64—C454—C455—C456	171 (3)
C3—C34—C35—O351	−0.5 (7)	C454—C455—C456—C451	−10 (6)
C35—N31—C311—C312	−31.0 (6)	C452—C451—C456—C455	10 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C356—H356···O1^i	0.93	2.32	3.115 (18)	143
C456—H456···O1^i	0.93	2.47	3.21 (2)	137

Symmetry code: (i) −x+1, −y+2, −z+1.

1-(4-Azidophenyl)-3-[3-methyl-5-(naphthalen-2-yloxy)-1-phenyl-1H-pyrazol-4-yl]prop-2-en-1-on (IIe)

Crystal data

C29H21N5O2	F(000) = 984
Mr = 471.51	Dx = 1.324 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.8460 (8) Å	Cell parameters from 4197 reflections
b = 22.4303 (18) Å	θ = 3.1–25.1°
c = 11.0490 (9) Å	µ = 0.09 mm^−1
β = 104.157 (2)°	T = 297 K
V = 2366.0 (3) Å^3	Block, orange
Z = 4	0.22 × 0.21 × 0.16 mm

Data collection

Bruker APEXII diffractometer	4196 independent reflections
Radiation source: fine focussealed tube	2463 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.092
φ and ω scans	θmax = 25.1°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −11→11
Tmin = 0.930, Tmax = 0.986	k = −26→26
43217 measured reflections	l = −12→13

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)] = 0.063	w = 1/[σ^2(Fo^2) + (0.0268P)^2 + 3.4386P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.154	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.23 e Å^−3
4196 reflections	Δρmin = −0.27 e Å^−3
327 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0143 (9)
Primary atom site location: dual

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
C1	0.3799 (4)	0.50783 (16)	0.2247 (3)	0.0478 (9)
O1	0.2646 (3)	0.49934 (13)	0.1526 (2)	0.0673 (8)
C2	0.5060 (4)	0.47779 (16)	0.2070 (3)	0.0489 (9)
H2	0.5904	0.4830	0.2662	0.059*
C3	0.5026 (4)	0.44316 (15)	0.1078 (3)	0.0465 (9)
H3	0.4164	0.4406	0.0502	0.056*
C11	0.3908 (3)	0.54796 (15)	0.3332 (3)	0.0433 (8)
C12	0.2693 (4)	0.56999 (17)	0.3595 (4)	0.0543 (10)
H12	0.1831	0.5588	0.3088	0.065*
C13	0.2725 (4)	0.60784 (17)	0.4580 (4)	0.0552 (10)
H13	0.1896	0.6212	0.4748	0.066*
C14	0.3990 (4)	0.62554 (16)	0.5309 (3)	0.0486 (9)
C15	0.5220 (4)	0.6051 (2)	0.5074 (4)	0.0656 (12)
H15	0.6078	0.6174	0.5572	0.079*
C16	0.5169 (4)	0.56643 (19)	0.4095 (4)	0.0595 (11)
H16	0.6001	0.5524	0.3944	0.071*
N14	0.4149 (4)	0.66594 (16)	0.6335 (3)	0.0655 (10)
N15	0.3037 (4)	0.68821 (16)	0.6481 (3)	0.0621 (9)
N16	0.2126 (4)	0.71190 (18)	0.6714 (4)	0.0877 (13)
N31	0.8165 (3)	0.36482 (13)	0.0799 (3)	0.0495 (8)
N32	0.7208 (3)	0.33982 (14)	−0.0191 (3)	0.0551 (8)
C33	0.6012 (4)	0.36732 (16)	−0.0196 (3)	0.0487 (9)
C34	0.6151 (4)	0.40921 (15)	0.0783 (3)	0.0444 (9)
C35	0.7544 (4)	0.40565 (15)	0.1390 (3)	0.0446 (9)
C311	0.9557 (4)	0.34178 (17)	0.1152 (3)	0.0491 (9)
C312	1.0685 (4)	0.37933 (18)	0.1521 (3)	0.0530 (10)
H312	1.0555	0.4204	0.1536	0.064*
C313	1.2010 (4)	0.3553 (2)	0.1870 (4)	0.0634 (11)
H313	1.2778	0.3805	0.2116	0.076*
C314	1.2215 (5)	0.2949 (2)	0.1861 (4)	0.0762 (13)
H314	1.3115	0.2792	0.2102	0.091*
C315	1.1087 (5)	0.2577 (2)	0.1496 (5)	0.0831 (15)
H315	1.1227	0.2167	0.1496	0.100*
C316	0.9736 (4)	0.28021 (19)	0.1125 (4)	0.0704 (13)
H316	0.8971	0.2549	0.0866	0.084*
C331	0.4703 (4)	0.35114 (19)	−0.1150 (4)	0.0665 (12)
H33A	0.4924	0.3233	−0.1734	0.100*
H33B	0.4298	0.3864	−0.1585	0.100*
H33C	0.4047	0.3333	−0.0743	0.100*
O351	0.8283 (2)	0.42967 (10)	0.2482 (2)	0.0485 (6)
C351	0.8655 (3)	0.51795 (16)	0.3666 (3)	0.0455 (9)
H351	0.8589	0.4953	0.4355	0.055*
C352	0.8523 (3)	0.49169 (15)	0.2527 (3)	0.0423 (8)
C353	0.8651 (4)	0.52368 (17)	0.1473 (3)	0.0498 (9)
H353	0.8558	0.5046	0.0709	0.060*
C354	0.8917 (4)	0.58332 (18)	0.1585 (3)	0.0551 (10)
H354	0.9021	0.6047	0.0893	0.066*
C355	0.9276 (4)	0.67581 (18)	0.2850 (4)	0.0664 (12)
H355	0.9410	0.6977	0.2175	0.080*
C356	0.9309 (5)	0.7037 (2)	0.3951 (5)	0.0732 (13)
H356	0.9446	0.7447	0.4017	0.088*
C357	0.9139 (4)	0.6714 (2)	0.4975 (4)	0.0685 (12)
H357	0.9152	0.6913	0.5716	0.082*
C358	0.8951 (4)	0.61082 (19)	0.4919 (4)	0.0570 (10)
H358	0.8862	0.5897	0.5620	0.068*
C359	0.9037 (4)	0.61317 (16)	0.2727 (3)	0.0498 (9)
C360	0.8896 (3)	0.58065 (16)	0.3779 (3)	0.0437 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.042 (2)	0.052 (2)	0.048 (2)	0.0016 (18)	0.0093 (17)	0.0008 (18)
O1	0.0452 (16)	0.089 (2)	0.0630 (17)	0.0038 (15)	0.0042 (14)	−0.0216 (16)
C2	0.037 (2)	0.058 (2)	0.050 (2)	0.0027 (17)	0.0077 (16)	−0.0056 (19)
C3	0.041 (2)	0.051 (2)	0.047 (2)	0.0013 (17)	0.0080 (16)	0.0021 (18)
C11	0.0349 (19)	0.048 (2)	0.046 (2)	0.0009 (16)	0.0098 (16)	−0.0019 (17)
C12	0.036 (2)	0.064 (3)	0.062 (2)	−0.0024 (18)	0.0092 (18)	−0.011 (2)
C13	0.042 (2)	0.063 (3)	0.061 (2)	−0.0017 (19)	0.0130 (18)	−0.014 (2)
C14	0.048 (2)	0.051 (2)	0.045 (2)	−0.0011 (18)	0.0082 (17)	−0.0036 (18)
C15	0.037 (2)	0.093 (3)	0.061 (3)	0.002 (2)	0.0013 (19)	−0.019 (2)
C16	0.039 (2)	0.082 (3)	0.056 (2)	0.007 (2)	0.0096 (18)	−0.013 (2)
N14	0.054 (2)	0.078 (2)	0.064 (2)	0.0027 (19)	0.0129 (17)	−0.0171 (19)
N15	0.066 (2)	0.058 (2)	0.061 (2)	−0.0092 (19)	0.0140 (19)	−0.0108 (18)
N16	0.076 (3)	0.085 (3)	0.107 (3)	0.002 (2)	0.032 (2)	−0.036 (2)
N31	0.0454 (18)	0.0521 (19)	0.0493 (18)	0.0013 (15)	0.0080 (15)	−0.0150 (15)
N32	0.0519 (19)	0.057 (2)	0.0527 (19)	−0.0057 (16)	0.0061 (15)	−0.0154 (16)
C33	0.048 (2)	0.049 (2)	0.047 (2)	−0.0067 (18)	0.0065 (17)	−0.0048 (18)
C34	0.045 (2)	0.045 (2)	0.042 (2)	−0.0008 (17)	0.0099 (16)	−0.0052 (17)
C35	0.046 (2)	0.044 (2)	0.042 (2)	−0.0012 (17)	0.0079 (17)	−0.0064 (17)
C311	0.046 (2)	0.056 (2)	0.047 (2)	0.0025 (19)	0.0137 (17)	−0.0074 (19)
C312	0.050 (2)	0.056 (2)	0.053 (2)	0.000 (2)	0.0148 (18)	−0.0016 (19)
C313	0.048 (2)	0.084 (3)	0.058 (3)	0.001 (2)	0.0133 (19)	−0.006 (2)
C314	0.054 (3)	0.089 (4)	0.086 (3)	0.017 (3)	0.018 (2)	−0.013 (3)
C315	0.072 (3)	0.069 (3)	0.109 (4)	0.019 (3)	0.024 (3)	−0.021 (3)
C316	0.062 (3)	0.059 (3)	0.093 (3)	0.003 (2)	0.023 (2)	−0.023 (2)
C331	0.060 (3)	0.068 (3)	0.066 (3)	−0.009 (2)	0.004 (2)	−0.014 (2)
O351	0.0554 (15)	0.0442 (14)	0.0417 (14)	−0.0010 (12)	0.0042 (11)	−0.0085 (12)
C351	0.040 (2)	0.053 (2)	0.040 (2)	−0.0020 (17)	0.0057 (16)	−0.0060 (18)
C352	0.0357 (19)	0.043 (2)	0.044 (2)	−0.0003 (16)	0.0026 (15)	−0.0079 (18)
C353	0.052 (2)	0.056 (3)	0.040 (2)	0.0036 (18)	0.0078 (17)	−0.0031 (18)
C354	0.058 (2)	0.060 (3)	0.045 (2)	0.005 (2)	0.0081 (18)	0.005 (2)
C355	0.070 (3)	0.053 (3)	0.071 (3)	0.002 (2)	0.007 (2)	−0.001 (2)
C356	0.074 (3)	0.055 (3)	0.083 (3)	0.006 (2)	0.005 (3)	−0.014 (3)
C357	0.056 (3)	0.072 (3)	0.072 (3)	0.000 (2)	0.007 (2)	−0.029 (3)
C358	0.050 (2)	0.070 (3)	0.049 (2)	−0.003 (2)	0.0093 (18)	−0.018 (2)
C359	0.045 (2)	0.052 (2)	0.047 (2)	0.0021 (18)	0.0028 (17)	−0.0025 (19)
C360	0.0306 (18)	0.055 (2)	0.042 (2)	0.0002 (16)	0.0034 (15)	−0.0121 (18)

Geometric parameters (Å, º)

C1—O1	1.232 (4)	C312—H312	0.9300
C1—C2	1.467 (5)	C313—C314	1.371 (6)
C1—C11	1.482 (5)	C313—H313	0.9300
C2—C3	1.337 (5)	C314—C315	1.368 (6)
C2—H2	0.9300	C314—H314	0.9300
C3—C34	1.446 (5)	C315—C316	1.387 (6)
C3—H3	0.9300	C315—H315	0.9300
C11—C16	1.382 (5)	C316—H316	0.9300
C11—C12	1.389 (5)	C331—H33A	0.9600
C12—C13	1.375 (5)	C331—H33B	0.9600
C12—H12	0.9300	C331—H33C	0.9600
C13—C14	1.367 (5)	O351—C352	1.410 (4)
C13—H13	0.9300	C351—C352	1.367 (5)
C14—C15	1.377 (5)	C351—C360	1.427 (5)
C14—N14	1.430 (5)	C351—H351	0.9300
C15—C16	1.378 (5)	C352—C353	1.400 (5)
C15—H15	0.9300	C353—C354	1.363 (5)
C16—H16	0.9300	C353—H353	0.9300
N14—N15	1.249 (5)	C354—C359	1.407 (5)
N15—N16	1.126 (5)	C354—H354	0.9300
N31—C35	1.353 (4)	C355—C356	1.360 (6)
N31—N32	1.376 (4)	C355—C359	1.426 (5)
N31—C311	1.427 (4)	C355—H355	0.9300
N32—C33	1.327 (4)	C356—C357	1.388 (6)
C33—C34	1.414 (5)	C356—H356	0.9300
C33—C331	1.497 (5)	C357—C358	1.371 (6)
C34—C35	1.374 (5)	C357—H357	0.9300
C35—O351	1.359 (4)	C358—C360	1.419 (5)
C311—C312	1.374 (5)	C358—H358	0.9300
C311—C316	1.394 (5)	C359—C360	1.408 (5)
C312—C313	1.377 (5)
O1—C1—C2	121.3 (3)	C314—C313—H313	119.5
O1—C1—C11	119.3 (3)	C312—C313—H313	119.5
C2—C1—C11	119.4 (3)	C315—C314—C313	119.6 (4)
C3—C2—C1	121.6 (3)	C315—C314—H314	120.2
C3—C2—H2	119.2	C313—C314—H314	120.2
C1—C2—H2	119.2	C314—C315—C316	121.0 (4)
C2—C3—C34	128.6 (3)	C314—C315—H315	119.5
C2—C3—H3	115.7	C316—C315—H315	119.5
C34—C3—H3	115.7	C315—C316—C311	118.2 (4)
C16—C11—C12	117.2 (3)	C315—C316—H316	120.9
C16—C11—C1	123.5 (3)	C311—C316—H316	120.9
C12—C11—C1	119.3 (3)	C33—C331—H33A	109.5
C13—C12—C11	122.1 (3)	C33—C331—H33B	109.5
C13—C12—H12	119.0	H33A—C331—H33B	109.5
C11—C12—H12	119.0	C33—C331—H33C	109.5
C14—C13—C12	119.2 (3)	H33A—C331—H33C	109.5
C14—C13—H13	120.4	H33B—C331—H33C	109.5
C12—C13—H13	120.4	C35—O351—C352	118.1 (3)
C13—C14—C15	120.6 (4)	C352—C351—C360	118.8 (3)
C13—C14—N14	124.0 (3)	C352—C351—H351	120.6
C15—C14—N14	115.5 (3)	C360—C351—H351	120.6
C14—C15—C16	119.5 (3)	C351—C352—C353	122.5 (3)
C14—C15—H15	120.2	C351—C352—O351	115.8 (3)
C16—C15—H15	120.2	C353—C352—O351	121.7 (3)
C15—C16—C11	121.5 (3)	C354—C353—C352	118.8 (3)
C15—C16—H16	119.3	C354—C353—H353	120.6
C11—C16—H16	119.3	C352—C353—H353	120.6
N15—N14—C14	115.2 (3)	C353—C354—C359	121.4 (4)
N16—N15—N14	172.4 (4)	C353—C354—H354	119.3
C35—N31—N32	110.9 (3)	C359—C354—H354	119.3
C35—N31—C311	129.0 (3)	C356—C355—C359	120.4 (4)
N32—N31—C311	119.6 (3)	C356—C355—H355	119.8
C33—N32—N31	104.3 (3)	C359—C355—H355	119.8
N32—C33—C34	112.7 (3)	C355—C356—C357	120.5 (4)
N32—C33—C331	120.0 (3)	C355—C356—H356	119.7
C34—C33—C331	127.2 (3)	C357—C356—H356	119.7
C35—C34—C33	103.4 (3)	C358—C357—C356	121.5 (4)
C35—C34—C3	130.5 (3)	C358—C357—H357	119.3
C33—C34—C3	126.0 (3)	C356—C357—H357	119.3
N31—C35—O351	119.3 (3)	C357—C358—C360	119.2 (4)
N31—C35—C34	108.6 (3)	C357—C358—H358	120.4
O351—C35—C34	131.6 (3)	C360—C358—H358	120.4
C312—C311—C316	121.1 (4)	C354—C359—C360	119.4 (3)
C312—C311—N31	120.8 (3)	C354—C359—C355	122.0 (4)
C316—C311—N31	118.1 (3)	C360—C359—C355	118.6 (4)
C311—C312—C313	119.0 (4)	C359—C360—C358	119.7 (3)
C311—C312—H312	120.5	C359—C360—C351	119.1 (3)
C313—C312—H312	120.5	C358—C360—C351	121.2 (4)
C314—C313—C312	121.1 (4)
O1—C1—C2—C3	4.4 (6)	C35—N31—C311—C312	−47.2 (5)
C11—C1—C2—C3	−177.2 (3)	N32—N31—C311—C312	140.9 (3)
C1—C2—C3—C34	−178.0 (3)	C35—N31—C311—C316	132.0 (4)
O1—C1—C11—C16	−171.1 (4)	N32—N31—C311—C316	−39.9 (5)
C2—C1—C11—C16	10.4 (5)	C316—C311—C312—C313	0.0 (6)
O1—C1—C11—C12	7.1 (5)	N31—C311—C312—C313	179.2 (3)
C2—C1—C11—C12	−171.4 (3)	C311—C312—C313—C314	−0.5 (6)
C16—C11—C12—C13	−1.0 (6)	C312—C313—C314—C315	0.3 (7)
C1—C11—C12—C13	−179.3 (4)	C313—C314—C315—C316	0.4 (7)
C11—C12—C13—C14	1.5 (6)	C314—C315—C316—C311	−0.9 (7)
C12—C13—C14—C15	−0.9 (6)	C312—C311—C316—C315	0.7 (6)
C12—C13—C14—N14	178.3 (4)	N31—C311—C316—C315	−178.5 (4)
C13—C14—C15—C16	−0.1 (6)	N31—C35—O351—C352	118.1 (3)
N14—C14—C15—C16	−179.4 (4)	C34—C35—O351—C352	−71.1 (5)
C14—C15—C16—C11	0.6 (7)	C360—C351—C352—C353	1.7 (5)
C12—C11—C16—C15	−0.1 (6)	C360—C351—C352—O351	−179.8 (3)
C1—C11—C16—C15	178.2 (4)	C35—O351—C352—C351	150.9 (3)
C13—C14—N14—N15	−5.0 (6)	C35—O351—C352—C353	−30.7 (4)
C15—C14—N14—N15	174.2 (4)	C351—C352—C353—C354	−0.1 (5)
C35—N31—N32—C33	1.2 (4)	O351—C352—C353—C354	−178.4 (3)
C311—N31—N32—C33	174.5 (3)	C352—C353—C354—C359	−1.2 (5)
N31—N32—C33—C34	−1.1 (4)	C359—C355—C356—C357	1.3 (6)
N31—N32—C33—C331	−179.2 (3)	C355—C356—C357—C358	0.8 (7)
N32—C33—C34—C35	0.5 (4)	C356—C357—C358—C360	−1.6 (6)
C331—C33—C34—C35	178.6 (4)	C353—C354—C359—C360	0.7 (5)
N32—C33—C34—C3	−175.5 (3)	C353—C354—C359—C355	−178.2 (4)
C331—C33—C34—C3	2.5 (6)	C356—C355—C359—C354	176.3 (4)
C2—C3—C34—C35	−3.7 (7)	C356—C355—C359—C360	−2.6 (6)
C2—C3—C34—C33	171.2 (4)	C354—C359—C360—C358	−177.1 (3)
N32—N31—C35—O351	171.8 (3)	C355—C359—C360—C358	1.8 (5)
C311—N31—C35—O351	−0.6 (6)	C354—C359—C360—C351	0.9 (5)
N32—N31—C35—C34	−0.9 (4)	C355—C359—C360—C351	179.9 (3)
C311—N31—C35—C34	−173.4 (3)	C357—C358—C360—C359	0.2 (5)
C33—C34—C35—N31	0.2 (4)	C357—C358—C360—C351	−177.8 (3)
C3—C34—C35—N31	176.0 (3)	C352—C351—C360—C359	−2.1 (5)
C33—C34—C35—O351	−171.3 (4)	C352—C351—C360—C358	175.9 (3)
C3—C34—C35—O351	4.4 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C353—H353···O1^i	0.93	2.47	3.288 (4)	147
C12—H12···Cg3^ii	0.93	2.93	3.761 (4)	150
C13—H13···Cg4^ii	0.93	2.73	3.547 (4)	148

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