Six 1-aroyl-4-(4-meth­oxy­phen­yl)piperazines: similar mol­ecular structures but different patterns of supra­molecular assembly

Kiran Kumar, H.; Yathirajan, H.S.; Sagar, B.K.; Foro, S.; Glidewell, C.

doi:10.1107/S2056989019010491

Six 1-aroyl-4-(4-methoxyphenyl)piperazines: similar molecular structures but different patterns of supramolecular assembly

H. Kiran Kumar, H. S. Yathirajan, B. K. Sagar, S. Foro and C. Glidewell

Six new 1-aroyl-4-(4-methoxyphenyl)piperazines have similar molecular structures, but their supramolecular assembly ranges from simple chains, via a chain of rings, to complex sheets.

Keywords: piperazines; crystal structure; isomorphism; disorder; hydrogen bonding; supramolecular assembly.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019010491/zl2757sup1.cif Contains datablocks global, I, II, III, IV, V, VI
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019010491/zl2757Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019010491/zl2757IIsup3.hkl Contains datablock II
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019010491/zl2757IIIsup4.hkl Contains datablock III
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019010491/zl2757IVsup5.hkl Contains datablock IV
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019010491/zl2757Vsup6.hkl Contains datablock V
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019010491/zl2757VIsup7.hkl Contains datablock VI
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019010491/zl2757Isup8.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019010491/zl2757IIsup9.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019010491/zl2757IIIsup10.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019010491/zl2757Vsup11.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019010491/zl2757VIsup12.cml Supplementary material

CCDC references: 1942579; 1942578; 1942577; 1942576; 1942575; 1942574

checkCIF report

Key indicators

Structure: I

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.035
wR factor = 0.089
Data-to-parameter ratio = 10.6

Structure: II

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.070
wR factor = 0.190
Data-to-parameter ratio = 15.9

Structure: III

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R factor = 0.048
wR factor = 0.127
Data-to-parameter ratio = 15.0

Structure: IV

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.045
wR factor = 0.131
Data-to-parameter ratio = 20.4

Structure: V

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.012 Å
R factor = 0.068
wR factor = 0.146
Data-to-parameter ratio = 18.4

Structure: VI

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R factor = 0.041
wR factor = 0.100
Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level B
PLAT915_ALERT_3_B No Flack x Check Done: Low Friedel Pair Coverage         21 %

Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12      ..O17      .       2.61 Ang.

Alert level G
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT128_ALERT_4_G Alternate Setting for Input Space Group  Cc              Ia Note
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        119 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

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

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




Datablock: II


Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low .      0.977 Why?
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............      0.005 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     17.014 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.195 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         65 Report

Alert level G
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        241 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
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

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



Alert level C
PLAT334_ALERT_2_C Small Aver. Benzene C-C Dist C31      -C36             1.37 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3A      ..O17      .       2.61 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.933 Check

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 ...          2 Report
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          8 Report
PLAT174_ALERT_4_G The CIF-Embedded .res File Contains FLAT Records          2 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          1 Report
PLAT177_ALERT_4_G The CIF-Embedded .res File Contains DELU Records          1 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        39% Note
PLAT432_ALERT_2_G Short Inter X...Y Contact  Cl32     ..C5               3.22 Ang.
                                             3/2-x,-1/2+y,z  =      7_755 Check
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         26 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        292 Note
PLAT953_ALERT_1_G Reported (CIF) and Actual (FCF) Hmax Differ by .          1 Units
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 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
  16 ALERT level G = General information/check it is not something unexpected

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




Datablock: IV


Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.616 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         17 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          8 Note

Alert level G
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 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

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


Alert level C
PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0116 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     11.267 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.185 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          5 Report
PLAT972_ALERT_2_C Check Calcd Resid. Dens.  1.75A   From I12            -2.24 eA-3
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large      37.16 Why ?
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT431_ALERT_2_G Short Inter HL..A Contact  I12      ..O17      .       3.36 Ang.
                                              3/2-x,1/2+y,z  =      7_765 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        272 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          2 Note

   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
   8 ALERT level G = General information/check it is not something unexpected

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


Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.457 Check

Alert level G
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        234 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Info

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

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

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009) for (I), (II), (III), (V), (VI); APEX2 (Bruker, 2015) for (IV). Cell refinement: CrysAlis RED (Oxford Diffraction, 2009) for (I), (II), (III), (V), (VI); SAINT (Bruker, 2015) for (IV). Data reduction: CrysAlis RED (Oxford Diffraction, 2009) for (I), (II), (III), (V), (VI); SAINT (Bruker, 2015) for (IV). For all structures, 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).

1-Benzoyl-4-(4-methoxyphenyl)piperazine (I) top

Crystal data top

C₁₈H₂₀N₂O₂	F(000) = 632
M_r = 296.36	D_x = 1.246 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 29.403 (5) Å	Cell parameters from 2137 reflections
b = 7.9811 (14) Å	θ = 2.7–27.7°
c = 6.7898 (13) Å	µ = 0.08 mm⁻¹
β = 97.352 (12)°	T = 293 K
V = 1580.3 (5) Å³	Plate, colourless
Z = 4	0.48 × 0.48 × 0.28 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD	2137 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1766 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ω scans	θ_max = 27.7°, θ_min = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −37→37
T_min = 0.951, T_max = 0.977	k = −10→10
5476 measured reflections	l = −4→8

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.035	w = 1/[σ²(F_o²) + (0.0414P)² + 0.3311P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.089	(Δ/σ)_max < 0.001
S = 1.08	Δρ_max = 0.14 e Å⁻³
2137 reflections	Δρ_min = −0.13 e Å⁻³
201 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.0041 (8)
Primary atom site location: difference Fourier map

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.46344 (7)	0.2520 (2)	0.4700 (3)	0.0433 (5)
C2	0.41820 (8)	0.2497 (3)	0.5365 (3)	0.0439 (6)
H2A	0.4189	0.3164	0.6563	0.053*
H2B	0.4105	0.1356	0.5686	0.053*
C3	0.38166 (9)	0.3177 (3)	0.3801 (3)	0.0440 (6)
H3A	0.3518	0.3068	0.4254	0.053*
H3B	0.3872	0.4358	0.3589	0.053*
N4	0.38189 (7)	0.2271 (2)	0.1945 (3)	0.0391 (5)
C5	0.42693 (8)	0.2452 (3)	0.1240 (3)	0.0437 (6)
H5A	0.4329	0.3627	0.1012	0.052*
H5B	0.4268	0.1862	−0.0009	0.052*
C6	0.46440 (9)	0.1755 (3)	0.2747 (4)	0.0453 (6)
H6A	0.4606	0.0552	0.2850	0.054*
H6B	0.4940	0.1963	0.2304	0.054*
C17	0.50023 (9)	0.2585 (3)	0.6128 (4)	0.0458 (6)
O17	0.49611 (7)	0.2708 (3)	0.7894 (3)	0.0697 (6)
C11	0.54739 (9)	0.2548 (3)	0.5486 (4)	0.0479 (6)
C12	0.56066 (10)	0.3679 (4)	0.4144 (5)	0.0638 (8)
H12	0.5399	0.4469	0.3558	0.077*
C13	0.60510 (11)	0.3637 (5)	0.3668 (6)	0.0780 (10)
H13	0.6143	0.4415	0.2778	0.094*
C14	0.63520 (11)	0.2479 (5)	0.4481 (5)	0.0754 (10)
H14	0.6646	0.2443	0.4120	0.091*
C15	0.62257 (11)	0.1350 (5)	0.5841 (5)	0.0776 (10)
H15	0.6435	0.0561	0.6411	0.093*
C16	0.57874 (10)	0.1391 (4)	0.6357 (4)	0.0626 (8)
H16	0.5702	0.0641	0.7292	0.075*
C41	0.34279 (8)	0.2454 (3)	0.0494 (3)	0.0382 (6)
C42	0.30660 (8)	0.3523 (3)	0.0761 (4)	0.0454 (6)
H42	0.3089	0.4215	0.1870	0.055*
C43	0.26735 (9)	0.3569 (3)	−0.0600 (4)	0.0497 (7)
H43	0.2435	0.4282	−0.0379	0.060*
C44	0.26289 (8)	0.2581 (4)	−0.2277 (4)	0.0474 (6)
C45	0.29861 (9)	0.1527 (3)	−0.2590 (4)	0.0464 (6)
H45	0.2963	0.0857	−0.3719	0.056*
C46	0.33796 (9)	0.1470 (3)	−0.1215 (4)	0.0444 (6)
H46	0.3617	0.0754	−0.1443	0.053*
O44	0.22252 (7)	0.2728 (3)	−0.3541 (3)	0.0671 (6)
C441	0.21605 (15)	0.1672 (6)	−0.5223 (6)	0.0907 (12)
H41A	0.1855	0.1811	−0.5889	0.136*
H41B	0.2206	0.0527	−0.4811	0.136*
H41C	0.2377	0.1961	−0.6112	0.136*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0391 (11)	0.0513 (13)	0.0412 (11)	−0.0030 (10)	0.0121 (9)	−0.0049 (9)
C2	0.0445 (14)	0.0484 (14)	0.0410 (14)	−0.0017 (12)	0.0139 (11)	−0.0028 (11)
C3	0.0435 (13)	0.0484 (14)	0.0429 (14)	0.0032 (12)	0.0163 (11)	−0.0018 (11)
N4	0.0364 (11)	0.0447 (11)	0.0384 (11)	0.0040 (10)	0.0136 (9)	−0.0015 (9)
C5	0.0447 (14)	0.0510 (15)	0.0380 (13)	0.0017 (11)	0.0154 (11)	0.0001 (10)
C6	0.0413 (13)	0.0521 (14)	0.0442 (13)	0.0038 (12)	0.0124 (11)	−0.0035 (11)
C17	0.0454 (15)	0.0482 (15)	0.0448 (15)	−0.0057 (13)	0.0093 (12)	−0.0004 (11)
O17	0.0558 (11)	0.1098 (18)	0.0448 (11)	−0.0141 (12)	0.0117 (9)	−0.0072 (11)
C11	0.0444 (14)	0.0553 (16)	0.0440 (14)	−0.0069 (13)	0.0055 (11)	−0.0037 (12)
C12	0.0483 (16)	0.074 (2)	0.0703 (19)	−0.0011 (15)	0.0131 (14)	0.0196 (15)
C13	0.056 (2)	0.103 (3)	0.078 (2)	−0.0136 (18)	0.0197 (17)	0.020 (2)
C14	0.0406 (17)	0.110 (3)	0.078 (2)	−0.0040 (18)	0.0141 (16)	−0.005 (2)
C15	0.0518 (19)	0.093 (3)	0.085 (2)	0.0120 (18)	−0.0028 (16)	0.0019 (19)
C16	0.0510 (17)	0.074 (2)	0.0608 (18)	−0.0008 (15)	0.0009 (14)	0.0100 (15)
C41	0.0386 (13)	0.0376 (13)	0.0407 (13)	−0.0028 (11)	0.0144 (11)	0.0050 (10)
C42	0.0402 (14)	0.0471 (16)	0.0511 (15)	0.0014 (11)	0.0143 (11)	−0.0046 (11)
C43	0.0396 (14)	0.0489 (16)	0.0633 (17)	0.0069 (13)	0.0165 (13)	0.0004 (13)
C44	0.0371 (14)	0.0555 (16)	0.0504 (15)	−0.0032 (13)	0.0093 (11)	0.0081 (13)
C45	0.0504 (15)	0.0488 (16)	0.0413 (14)	−0.0014 (13)	0.0117 (11)	−0.0033 (11)
C46	0.0468 (14)	0.0449 (15)	0.0439 (14)	0.0085 (12)	0.0155 (11)	0.0000 (11)
O44	0.0461 (11)	0.0883 (16)	0.0651 (13)	0.0030 (11)	0.0007 (9)	−0.0011 (12)
C441	0.076 (2)	0.110 (3)	0.078 (3)	0.001 (2)	−0.0201 (18)	−0.015 (2)

Geometric parameters (Å, º) top

N1—C17	1.358 (3)	C13—C14	1.348 (5)
N1—C2	1.458 (3)	C13—H13	0.9300
N1—C6	1.463 (3)	C14—C15	1.375 (5)
C2—C3	1.511 (4)	C14—H14	0.9300
C2—H2A	0.9700	C15—C16	1.378 (4)
C2—H2B	0.9700	C15—H15	0.9300
C3—N4	1.454 (3)	C16—H16	0.9300
C3—H3A	0.9700	C41—C46	1.393 (4)
C3—H3B	0.9700	C41—C42	1.394 (3)
N4—C41	1.422 (3)	C42—C43	1.384 (4)
N4—C5	1.472 (3)	C42—H42	0.9300
C5—C6	1.511 (4)	C43—C44	1.378 (4)
C5—H5A	0.9700	C43—H43	0.9300
C5—H5B	0.9700	C44—O44	1.378 (3)
C6—H6A	0.9700	C44—C45	1.383 (4)
C6—H6B	0.9700	C45—C46	1.391 (4)
C17—O17	1.225 (3)	C45—H45	0.9300
C17—C11	1.506 (3)	C46—H46	0.9300
C11—C12	1.374 (4)	O44—C441	1.412 (4)
C11—C16	1.383 (4)	C441—H41A	0.9600
C12—C13	1.386 (4)	C441—H41B	0.9600
C12—H12	0.9300	C441—H41C	0.9600

C17—N1—C2	117.04 (19)	C13—C12—H12	120.2
C17—N1—C6	123.82 (19)	C14—C13—C12	120.7 (3)
C2—N1—C6	113.5 (2)	C14—C13—H13	119.7
N1—C2—C3	111.88 (19)	C12—C13—H13	119.7
N1—C2—H2A	109.2	C13—C14—C15	120.3 (3)
C3—C2—H2A	109.2	C13—C14—H14	119.8
N1—C2—H2B	109.2	C15—C14—H14	119.8
C3—C2—H2B	109.2	C14—C15—C16	119.8 (3)
H2A—C2—H2B	107.9	C14—C15—H15	120.1
N4—C3—C2	110.4 (2)	C16—C15—H15	120.1
N4—C3—H3A	109.6	C15—C16—C11	120.1 (3)
C2—C3—H3A	109.6	C15—C16—H16	120.0
N4—C3—H3B	109.6	C11—C16—H16	120.0
C2—C3—H3B	109.6	C46—C41—C42	117.1 (2)
H3A—C3—H3B	108.1	C46—C41—N4	120.4 (2)
C41—N4—C3	117.17 (18)	C42—C41—N4	122.4 (2)
C41—N4—C5	116.48 (17)	C43—C42—C41	121.0 (2)
C3—N4—C5	109.71 (19)	C43—C42—H42	119.5
N4—C5—C6	110.63 (18)	C41—C42—H42	119.5
N4—C5—H5A	109.5	C44—C43—C42	121.3 (2)
C6—C5—H5A	109.5	C44—C43—H43	119.3
N4—C5—H5B	109.5	C42—C43—H43	119.3
C6—C5—H5B	109.5	C43—C44—O44	116.7 (2)
H5A—C5—H5B	108.1	C43—C44—C45	118.8 (2)
N1—C6—C5	111.3 (2)	O44—C44—C45	124.5 (3)
N1—C6—H6A	109.4	C44—C45—C46	120.0 (2)
C5—C6—H6A	109.4	C44—C45—H45	120.0
N1—C6—H6B	109.4	C46—C45—H45	120.0
C5—C6—H6B	109.4	C45—C46—C41	121.9 (2)
H6A—C6—H6B	108.0	C45—C46—H46	119.1
O17—C17—N1	122.2 (2)	C41—C46—H46	119.1
O17—C17—C11	119.7 (2)	C44—O44—C441	118.0 (3)
N1—C17—C11	118.1 (2)	O44—C441—H41A	109.5
C12—C11—C16	119.5 (3)	O44—C441—H41B	109.5
C12—C11—C17	122.0 (3)	H41A—C441—H41B	109.5
C16—C11—C17	118.5 (2)	O44—C441—H41C	109.5
C11—C12—C13	119.6 (3)	H41A—C441—H41C	109.5
C11—C12—H12	120.2	H41B—C441—H41C	109.5

C17—N1—C2—C3	154.8 (2)	C12—C13—C14—C15	−1.9 (6)
C6—N1—C2—C3	−50.5 (3)	C13—C14—C15—C16	0.8 (6)
N1—C2—C3—N4	55.1 (3)	C14—C15—C16—C11	1.0 (5)
C2—C3—N4—C41	164.3 (2)	C12—C11—C16—C15	−1.6 (4)
C2—C3—N4—C5	−59.9 (3)	C17—C11—C16—C15	−178.4 (3)
C41—N4—C5—C6	−163.8 (2)	C3—N4—C41—C46	−172.1 (2)
C3—N4—C5—C6	60.1 (3)	C5—N4—C41—C46	55.1 (3)
C17—N1—C6—C5	−157.0 (2)	C3—N4—C41—C42	3.6 (3)
C2—N1—C6—C5	50.3 (3)	C5—N4—C41—C42	−129.2 (2)
N4—C5—C6—N1	−54.7 (3)	C46—C41—C42—C43	1.3 (4)
C2—N1—C17—O17	−3.7 (4)	N4—C41—C42—C43	−174.5 (2)
C6—N1—C17—O17	−155.6 (3)	C41—C42—C43—C44	−0.9 (4)
C2—N1—C17—C11	177.9 (2)	C42—C43—C44—O44	−179.7 (2)
C6—N1—C17—C11	26.1 (3)	C42—C43—C44—C45	0.0 (4)
O17—C17—C11—C12	−123.5 (3)	C43—C44—C45—C46	0.5 (4)
N1—C17—C11—C12	54.9 (4)	O44—C44—C45—C46	−179.8 (2)
O17—C17—C11—C16	53.2 (4)	C44—C45—C46—C41	−0.1 (4)
N1—C17—C11—C16	−128.4 (3)	C42—C41—C46—C45	−0.8 (4)
C16—C11—C12—C13	0.6 (5)	N4—C41—C46—C45	175.1 (2)
C17—C11—C12—C13	177.2 (3)	C43—C44—O44—C441	−177.0 (3)
C11—C12—C13—C14	1.2 (6)	C45—C44—O44—C441	3.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O17ⁱ	0.93	2.61	3.497 (4)	160

Symmetry code: (i) x, −y+1, z−1/2.

1-(2-Fluorobenzoyl)-4-(4-methoxyphenyl)piperazine (II) top

Crystal data top

C₁₈H₁₉FN₂O₂	F(000) = 664
M_r = 314.35	D_x = 1.324 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.998 (2) Å	Cell parameters from 3334 reflections
b = 7.938 (2) Å	θ = 2.7–28.4°
c = 28.415 (6) Å	µ = 0.10 mm⁻¹
β = 92.20 (3)°	T = 293 K
V = 1577.3 (7) Å³	Block, colourless
Z = 4	0.48 × 0.36 × 0.32 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD	3315 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1863 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
ω scans	θ_max = 27.6°, θ_min = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −8→5
T_min = 0.931, T_max = 0.970	k = −10→5
6039 measured reflections	l = −36→28

Refinement top

Refinement on F²	Primary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.070	H-atom parameters constrained
wR(F²) = 0.190	w = 1/[σ²(F_o²) + (0.0566P)² + 1.2906P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
3315 reflections	Δρ_max = 0.21 e Å⁻³
208 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.7575 (4)	0.5325 (4)	0.41972 (9)	0.0547 (8)
C2	0.5981 (5)	0.4154 (5)	0.42224 (11)	0.0560 (9)
H2A	0.5401	0.4256	0.4526	0.067*
H2B	0.6439	0.3008	0.4191	0.067*
C3	0.4517 (5)	0.4532 (5)	0.38354 (11)	0.0541 (9)
H3A	0.3490	0.3714	0.3845	0.065*
H3B	0.3976	0.5639	0.3887	0.065*
N4	0.5348 (3)	0.4485 (3)	0.33706 (9)	0.0475 (7)
C5	0.6957 (5)	0.5657 (5)	0.33544 (11)	0.0567 (9)
H5A	0.6492	0.6801	0.3386	0.068*
H5B	0.7543	0.5563	0.3052	0.068*
C6	0.8428 (5)	0.5301 (5)	0.37396 (11)	0.0623 (10)
H6A	0.8999	0.4207	0.3688	0.075*
H6B	0.9433	0.6142	0.3733	0.075*
C17	0.7990 (4)	0.6422 (4)	0.45441 (11)	0.0464 (8)
O17	0.7152 (3)	0.6409 (3)	0.49118 (8)	0.0632 (7)
C11	0.9578 (4)	0.7658 (4)	0.44823 (10)	0.0436 (8)
C12	0.9203 (4)	0.9299 (5)	0.43559 (11)	0.0516 (8)
F12	0.7371 (3)	0.9715 (3)	0.42311 (8)	0.0805 (7)
C13	1.0575 (5)	1.0534 (5)	0.43537 (12)	0.0628 (10)
H13	1.0261	1.1635	0.4270	0.075*
C14	1.2416 (5)	1.0101 (5)	0.44775 (12)	0.0630 (10)
H14	1.3371	1.0916	0.4479	0.076*
C15	1.2868 (5)	0.8473 (6)	0.45996 (12)	0.0623 (10)
H15	1.4129	0.8190	0.4678	0.075*
C16	1.1467 (5)	0.7253 (5)	0.46063 (11)	0.0542 (9)
H16	1.1785	0.6156	0.4694	0.065*
C41	0.4022 (4)	0.4532 (4)	0.29834 (11)	0.0466 (8)
C42	0.2375 (5)	0.3540 (4)	0.29751 (11)	0.0516 (8)
H42	0.2144	0.2861	0.3234	0.062*
C43	0.1076 (5)	0.3529 (5)	0.25972 (11)	0.0545 (9)
H43	−0.0010	0.2857	0.2606	0.065*
C44	0.1383 (5)	0.4511 (5)	0.22074 (11)	0.0529 (9)
C45	0.3014 (5)	0.5483 (5)	0.22029 (12)	0.0567 (9)
H45	0.3256	0.6126	0.1938	0.068*
C46	0.4291 (5)	0.5518 (4)	0.25840 (11)	0.0538 (9)
H46	0.5358	0.6214	0.2575	0.065*
O44	0.0183 (4)	0.4587 (4)	0.18145 (8)	0.0718 (8)
C441	−0.1580 (5)	0.3703 (6)	0.18248 (13)	0.0756 (12)
H41A	−0.2281	0.3857	0.1531	0.113*
H41B	−0.1334	0.2525	0.1874	0.113*
H41C	−0.2317	0.4128	0.2077	0.113*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0531 (16)	0.062 (2)	0.0495 (15)	−0.0161 (15)	0.0145 (12)	−0.0028 (14)
C2	0.059 (2)	0.054 (2)	0.0556 (19)	−0.0119 (18)	0.0113 (16)	0.0044 (17)
C3	0.0531 (19)	0.058 (2)	0.0528 (19)	−0.0110 (18)	0.0184 (15)	0.0043 (16)
N4	0.0481 (14)	0.0478 (18)	0.0474 (14)	−0.0074 (13)	0.0150 (12)	−0.0020 (13)
C5	0.0568 (19)	0.065 (2)	0.0496 (18)	−0.0130 (19)	0.0224 (16)	−0.0017 (17)
C6	0.0518 (19)	0.081 (3)	0.056 (2)	−0.013 (2)	0.0173 (16)	−0.0064 (19)
C17	0.0458 (17)	0.046 (2)	0.0478 (18)	0.0034 (16)	0.0095 (14)	0.0067 (16)
O17	0.0736 (16)	0.0618 (17)	0.0561 (13)	−0.0101 (13)	0.0245 (12)	−0.0006 (12)
C11	0.0442 (17)	0.048 (2)	0.0396 (15)	0.0010 (15)	0.0066 (12)	0.0047 (14)
C12	0.0423 (17)	0.055 (2)	0.058 (2)	0.0062 (17)	0.0018 (14)	0.0089 (17)
F12	0.0519 (12)	0.0683 (16)	0.1207 (19)	0.0103 (11)	−0.0041 (11)	0.0252 (13)
C13	0.065 (2)	0.049 (2)	0.074 (2)	−0.003 (2)	0.0074 (18)	0.0086 (19)
C14	0.060 (2)	0.069 (3)	0.061 (2)	−0.017 (2)	0.0079 (17)	−0.009 (2)
C15	0.0420 (18)	0.089 (3)	0.056 (2)	−0.001 (2)	0.0027 (15)	−0.001 (2)
C16	0.0522 (19)	0.058 (2)	0.0523 (19)	0.0106 (18)	0.0058 (15)	0.0086 (17)
C41	0.0496 (18)	0.0407 (19)	0.0511 (18)	−0.0006 (16)	0.0218 (14)	−0.0056 (15)
C42	0.061 (2)	0.047 (2)	0.0485 (18)	−0.0089 (18)	0.0179 (15)	−0.0018 (16)
C43	0.0552 (19)	0.051 (2)	0.058 (2)	−0.0096 (18)	0.0163 (16)	−0.0074 (18)
C44	0.0569 (19)	0.055 (2)	0.0479 (18)	0.0019 (18)	0.0114 (16)	−0.0065 (17)
C45	0.064 (2)	0.053 (2)	0.054 (2)	−0.0051 (19)	0.0201 (17)	0.0065 (17)
C46	0.0523 (18)	0.053 (2)	0.057 (2)	−0.0109 (18)	0.0163 (16)	0.0021 (17)
O44	0.0685 (16)	0.087 (2)	0.0598 (15)	−0.0122 (15)	0.0054 (12)	0.0035 (14)
C441	0.063 (2)	0.097 (3)	0.067 (2)	−0.014 (2)	0.0057 (18)	−0.009 (2)

Geometric parameters (Å, º) top

N1—C17	1.338 (4)	C13—C14	1.367 (5)
N1—C6	1.452 (4)	C13—H13	0.9300
N1—C2	1.456 (4)	C14—C15	1.371 (5)
C2—C3	1.504 (4)	C14—H14	0.9300
C2—H2A	0.9700	C15—C16	1.379 (5)
C2—H2B	0.9700	C15—H15	0.9300
C3—N4	1.464 (4)	C16—H16	0.9300
C3—H3A	0.9700	C41—C42	1.396 (4)
C3—H3B	0.9700	C41—C46	1.397 (4)
N4—C41	1.412 (4)	C42—C43	1.380 (4)
N4—C5	1.462 (4)	C42—H42	0.9300
C5—C6	1.500 (5)	C43—C44	1.378 (4)
C5—H5A	0.9700	C43—H43	0.9300
C5—H5B	0.9700	C44—O44	1.373 (4)
C6—H6A	0.9700	C44—C45	1.378 (5)
C6—H6B	0.9700	C45—C46	1.378 (5)
C17—O17	1.218 (3)	C45—H45	0.9300
C17—C11	1.498 (4)	C46—H46	0.9300
C11—C12	1.374 (5)	O44—C441	1.421 (4)
C11—C16	1.393 (4)	C441—H41A	0.9600
C12—F12	1.358 (4)	C441—H41B	0.9600
C12—C13	1.372 (5)	C441—H41C	0.9600

C17—N1—C6	125.6 (3)	C13—C12—C11	123.5 (3)
C17—N1—C2	121.6 (3)	C14—C13—C12	118.2 (4)
C6—N1—C2	112.2 (3)	C14—C13—H13	120.9
N1—C2—C3	109.8 (3)	C12—C13—H13	120.9
N1—C2—H2A	109.7	C13—C14—C15	120.5 (4)
C3—C2—H2A	109.7	C13—C14—H14	119.7
N1—C2—H2B	109.7	C15—C14—H14	119.7
C3—C2—H2B	109.7	C14—C15—C16	120.6 (3)
H2A—C2—H2B	108.2	C14—C15—H15	119.7
N4—C3—C2	111.8 (3)	C16—C15—H15	119.7
N4—C3—H3A	109.2	C15—C16—C11	120.2 (3)
C2—C3—H3A	109.2	C15—C16—H16	119.9
N4—C3—H3B	109.2	C11—C16—H16	119.9
C2—C3—H3B	109.2	C42—C41—C46	116.1 (3)
H3A—C3—H3B	107.9	C42—C41—N4	121.0 (3)
C41—N4—C5	116.3 (2)	C46—C41—N4	122.8 (3)
C41—N4—C3	115.5 (2)	C43—C42—C41	122.4 (3)
C5—N4—C3	110.2 (2)	C43—C42—H42	118.8
N4—C5—C6	111.4 (3)	C41—C42—H42	118.8
N4—C5—H5A	109.3	C44—C43—C42	120.3 (3)
C6—C5—H5A	109.3	C44—C43—H43	119.9
N4—C5—H5B	109.3	C42—C43—H43	119.9
C6—C5—H5B	109.3	O44—C44—C45	116.7 (3)
H5A—C5—H5B	108.0	O44—C44—C43	124.7 (3)
N1—C6—C5	110.9 (3)	C45—C44—C43	118.6 (3)
N1—C6—H6A	109.5	C46—C45—C44	121.1 (3)
C5—C6—H6A	109.5	C46—C45—H45	119.5
N1—C6—H6B	109.5	C44—C45—H45	119.5
C5—C6—H6B	109.5	C45—C46—C41	121.6 (3)
H6A—C6—H6B	108.0	C45—C46—H46	119.2
O17—C17—N1	121.9 (3)	C41—C46—H46	119.2
O17—C17—C11	119.3 (3)	C44—O44—C441	117.8 (3)
N1—C17—C11	118.7 (2)	O44—C441—H41A	109.5
C12—C11—C16	117.0 (3)	O44—C441—H41B	109.5
C12—C11—C17	121.1 (3)	H41A—C441—H41B	109.5
C16—C11—C17	121.4 (3)	O44—C441—H41C	109.5
F12—C12—C13	118.6 (3)	H41A—C441—H41C	109.5
F12—C12—C11	117.9 (3)	H41B—C441—H41C	109.5

C17—N1—C2—C3	116.2 (3)	C11—C12—C13—C14	1.0 (5)
C6—N1—C2—C3	−55.9 (4)	C12—C13—C14—C15	0.1 (5)
N1—C2—C3—N4	56.2 (4)	C13—C14—C15—C16	−1.0 (5)
C2—C3—N4—C41	169.4 (3)	C14—C15—C16—C11	0.9 (5)
C2—C3—N4—C5	−56.4 (4)	C12—C11—C16—C15	0.1 (4)
C41—N4—C5—C6	−170.6 (3)	C17—C11—C16—C15	−172.2 (3)
C3—N4—C5—C6	55.5 (4)	C5—N4—C41—C42	−176.2 (3)
C17—N1—C6—C5	−115.8 (4)	C3—N4—C41—C42	−44.8 (4)
C2—N1—C6—C5	55.9 (4)	C5—N4—C41—C46	5.7 (4)
N4—C5—C6—N1	−55.4 (4)	C3—N4—C41—C46	137.2 (3)
C6—N1—C17—O17	176.7 (3)	C46—C41—C42—C43	−0.3 (5)
C2—N1—C17—O17	5.7 (5)	N4—C41—C42—C43	−178.4 (3)
C6—N1—C17—C11	−5.5 (5)	C41—C42—C43—C44	0.5 (5)
C2—N1—C17—C11	−176.4 (3)	C42—C43—C44—O44	179.9 (3)
O17—C17—C11—C12	−81.2 (4)	C42—C43—C44—C45	0.6 (5)
N1—C17—C11—C12	100.9 (4)	O44—C44—C45—C46	178.8 (3)
O17—C17—C11—C16	90.8 (4)	C43—C44—C45—C46	−1.8 (5)
N1—C17—C11—C16	−87.2 (4)	C44—C45—C46—C41	2.1 (5)
C16—C11—C12—F12	179.6 (3)	C42—C41—C46—C45	−1.0 (5)
C17—C11—C12—F12	−8.1 (4)	N4—C41—C46—C45	177.1 (3)
C16—C11—C12—C13	−1.0 (5)	C45—C44—O44—C441	−175.1 (3)
C17—C11—C12—C13	171.2 (3)	C43—C44—O44—C441	5.5 (5)
F12—C12—C13—C14	−179.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O17ⁱ	0.97	2.50	3.387 (4)	152
C16—H16···O17ⁱⁱ	0.93	2.43	3.340 (5)	167

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

1-(2-Chlorobenzoyl)-4-(4-methoxyphenyl)piperazine (III) top

Crystal data top

C₁₈H₁₉ClN₂O₂	D_x = 1.322 Mg m⁻³
M_r = 330.80	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 3642 reflections
a = 13.0320 (11) Å	θ = 2.6–27.8°
b = 13.2470 (13) Å	µ = 0.24 mm⁻¹
c = 19.258 (2) Å	T = 293 K
V = 3324.6 (6) Å³	Block, yellow
Z = 8	0.50 × 0.40 × 0.38 mm
F(000) = 1392

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD	3642 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2407 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ω scans	θ_max = 27.8°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −16→17
T_min = 0.862, T_max = 0.912	k = −16→17
13862 measured reflections	l = −12→25

Refinement top

Refinement on F²	26 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.127	w = 1/[σ²(F_o²) + (0.0484P)² + 1.4776P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3642 reflections	Δρ_max = 0.23 e Å⁻³
243 parameters	Δρ_min = −0.45 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	0.68382 (12)	0.28146 (13)	0.41176 (9)	0.0526 (4)
C2	0.58246 (16)	0.25886 (18)	0.43972 (13)	0.0642 (6)
H2A	0.5883	0.2424	0.4886	0.077*
H2B	0.5542	0.2006	0.4160	0.077*
C3	0.51117 (15)	0.34757 (17)	0.43087 (11)	0.0560 (6)
H3A	0.4428	0.3292	0.4463	0.067*
H3B	0.5349	0.4035	0.4592	0.067*
N4	0.50753 (11)	0.37844 (12)	0.35839 (8)	0.0447 (4)
C5	0.60999 (14)	0.40544 (16)	0.33358 (10)	0.0488 (5)
H5A	0.6361	0.4619	0.3604	0.059*
H5B	0.6061	0.4261	0.2853	0.059*
C6	0.68172 (15)	0.31756 (17)	0.34028 (11)	0.0539 (5)
H6A	0.6595	0.2635	0.3098	0.065*
H6B	0.7502	0.3378	0.3263	0.065*
C17	0.76756 (19)	0.26749 (18)	0.45027 (14)	0.0534 (6)	0.942 (2)
O17	0.76535 (19)	0.2354 (2)	0.50989 (12)	0.0936 (9)	0.942 (2)
C11	0.86962 (18)	0.29271 (17)	0.41824 (14)	0.0470 (5)	0.942 (2)
C12	0.9128 (2)	0.38720 (18)	0.42449 (16)	0.0535 (6)	0.942 (2)
Cl12	0.84046 (7)	0.48603 (5)	0.46012 (3)	0.0799 (3)	0.942 (2)
C13	1.0112 (3)	0.4066 (3)	0.4020 (2)	0.0726 (8)	0.942 (2)
H13	1.0393	0.4707	0.4073	0.087*	0.942 (2)
C14	1.0670 (3)	0.3318 (4)	0.3718 (3)	0.0882 (11)	0.942 (2)
H14	1.1339	0.3446	0.3573	0.106*	0.942 (2)
C15	1.0253 (3)	0.2376 (3)	0.36267 (19)	0.0843 (11)	0.942 (2)
H15	1.0628	0.1871	0.3407	0.101*	0.942 (2)
C16	0.9270 (2)	0.2185 (2)	0.38639 (15)	0.0670 (7)	0.942 (2)
H16	0.8991	0.1544	0.3808	0.080*	0.942 (2)
C37	0.773 (2)	0.2975 (19)	0.454 (2)	0.0534 (6)	0.058 (2)
O37	0.777 (3)	0.285 (4)	0.517 (2)	0.0936 (9)	0.058 (2)
C31	0.871 (3)	0.3261 (14)	0.418 (2)	0.0470 (5)	0.058 (2)
C32	0.935 (2)	0.2481 (15)	0.3977 (18)	0.0670 (7)	0.058 (2)
Cl32	0.8826 (19)	0.1267 (11)	0.4022 (13)	0.162 (10)	0.058 (2)
C33	1.035 (3)	0.264 (3)	0.379 (3)	0.0843 (11)	0.058 (2)
H33	1.0769	0.2102	0.3661	0.101*	0.058 (2)
C34	1.073 (3)	0.360 (3)	0.381 (5)	0.0882 (11)	0.058 (2)
H34	1.1407	0.3717	0.3675	0.106*	0.058 (2)
C35	1.013 (4)	0.439 (3)	0.403 (4)	0.0726 (8)	0.058 (2)
H35	1.0396	0.5039	0.4036	0.087*	0.058 (2)
C36	0.913 (3)	0.4206 (16)	0.424 (3)	0.0535 (6)	0.058 (2)
H36	0.8746	0.4729	0.4429	0.064*	0.058 (2)
C41	0.42740 (14)	0.44424 (14)	0.33779 (10)	0.0415 (4)
C42	0.35531 (15)	0.48382 (16)	0.38335 (11)	0.0523 (5)
H42	0.3599	0.4687	0.4304	0.063*
C43	0.27626 (15)	0.54574 (17)	0.35992 (11)	0.0547 (5)
H43	0.2290	0.5716	0.3914	0.066*
C44	0.26749 (14)	0.56901 (15)	0.29086 (10)	0.0469 (5)
C45	0.33768 (16)	0.52910 (16)	0.24458 (11)	0.0527 (5)
H45	0.3323	0.5440	0.1975	0.063*
C46	0.41523 (16)	0.46762 (16)	0.26773 (10)	0.0519 (5)
H46	0.4611	0.4407	0.2357	0.062*
O44	0.19396 (11)	0.62997 (12)	0.26191 (8)	0.0676 (5)
C441	0.1267 (2)	0.6808 (2)	0.30737 (15)	0.0838 (8)
H41A	0.0850	0.7271	0.2814	0.126*
H41B	0.1658	0.7173	0.3413	0.126*
H41C	0.0834	0.6325	0.3303	0.126*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0402 (9)	0.0602 (11)	0.0574 (10)	0.0018 (8)	−0.0043 (8)	0.0178 (9)
C2	0.0463 (12)	0.0702 (15)	0.0760 (15)	−0.0061 (11)	−0.0039 (11)	0.0334 (12)
C3	0.0438 (11)	0.0697 (14)	0.0546 (12)	−0.0020 (10)	0.0042 (9)	0.0198 (11)
N4	0.0396 (8)	0.0489 (9)	0.0455 (9)	0.0011 (7)	0.0009 (7)	0.0096 (7)
C5	0.0410 (10)	0.0582 (12)	0.0472 (11)	0.0023 (10)	0.0022 (8)	0.0129 (9)
C6	0.0442 (11)	0.0664 (14)	0.0510 (12)	0.0062 (10)	−0.0026 (9)	0.0051 (10)
C17	0.0481 (12)	0.0511 (14)	0.0610 (14)	0.0011 (12)	−0.0065 (10)	0.0135 (12)
O17	0.0598 (12)	0.147 (2)	0.0735 (12)	−0.0024 (16)	−0.0080 (9)	0.0564 (16)
C11	0.0435 (11)	0.0495 (13)	0.0482 (11)	0.0035 (12)	−0.0107 (9)	0.0073 (12)
C12	0.0615 (13)	0.0566 (15)	0.0424 (11)	−0.0085 (15)	−0.0129 (10)	0.0079 (13)
Cl12	0.1176 (7)	0.0594 (4)	0.0626 (4)	−0.0059 (4)	−0.0025 (4)	−0.0119 (3)
C13	0.0680 (16)	0.092 (2)	0.0575 (14)	−0.0303 (18)	−0.0207 (12)	0.024 (2)
C14	0.0466 (14)	0.143 (3)	0.075 (3)	0.000 (2)	−0.0060 (14)	0.041 (2)
C15	0.0634 (17)	0.113 (3)	0.076 (3)	0.0371 (19)	0.0043 (16)	0.0098 (19)
C16	0.0605 (15)	0.0611 (17)	0.0794 (18)	0.0121 (14)	−0.0092 (13)	−0.0010 (14)
C37	0.0481 (12)	0.0511 (14)	0.0610 (14)	0.0011 (12)	−0.0065 (10)	0.0135 (12)
O37	0.0598 (12)	0.147 (2)	0.0735 (12)	−0.0024 (16)	−0.0080 (9)	0.0564 (16)
C31	0.0435 (11)	0.0495 (13)	0.0482 (11)	0.0035 (12)	−0.0107 (9)	0.0073 (12)
C32	0.0605 (15)	0.0611 (17)	0.0794 (18)	0.0121 (14)	−0.0092 (13)	−0.0010 (14)
Cl32	0.22 (2)	0.072 (9)	0.19 (2)	0.000 (11)	−0.011 (17)	−0.030 (11)
C33	0.0634 (17)	0.113 (3)	0.076 (3)	0.0371 (19)	0.0043 (16)	0.0098 (19)
C34	0.0466 (14)	0.143 (3)	0.075 (3)	0.000 (2)	−0.0060 (14)	0.041 (2)
C35	0.0680 (16)	0.092 (2)	0.0575 (14)	−0.0303 (18)	−0.0207 (12)	0.024 (2)
C36	0.0615 (13)	0.0566 (15)	0.0424 (11)	−0.0085 (15)	−0.0129 (10)	0.0079 (13)
C41	0.0383 (9)	0.0408 (10)	0.0454 (10)	−0.0011 (8)	0.0000 (8)	0.0008 (8)
C42	0.0483 (11)	0.0649 (13)	0.0436 (11)	0.0045 (10)	0.0057 (9)	0.0076 (10)
C43	0.0422 (11)	0.0633 (14)	0.0586 (13)	0.0070 (10)	0.0122 (9)	0.0011 (10)
C44	0.0411 (10)	0.0433 (11)	0.0563 (12)	0.0035 (9)	−0.0017 (9)	−0.0012 (9)
C45	0.0588 (12)	0.0577 (12)	0.0417 (10)	0.0126 (11)	−0.0039 (9)	−0.0020 (9)
C46	0.0523 (12)	0.0603 (13)	0.0431 (11)	0.0163 (10)	0.0025 (9)	−0.0064 (9)
O44	0.0592 (9)	0.0722 (10)	0.0715 (10)	0.0277 (8)	−0.0029 (8)	0.0013 (8)
C441	0.0720 (16)	0.0823 (18)	0.097 (2)	0.0365 (15)	0.0069 (15)	0.0016 (16)

Geometric parameters (Å, º) top

N1—C17	1.332 (3)	C16—H16	0.9300
N1—C37	1.43 (4)	C37—O37	1.222 (10)
N1—C2	1.458 (3)	C37—C31	1.508 (9)
N1—C6	1.458 (3)	C31—C36	1.372 (10)
C2—C3	1.508 (3)	C31—C32	1.381 (9)
C2—H2A	0.9700	C32—C33	1.371 (10)
C2—H2B	0.9700	C32—Cl32	1.749 (10)
C3—N4	1.455 (2)	C33—C34	1.362 (10)
C3—H3A	0.9700	C33—H33	0.9300
C3—H3B	0.9700	C34—C35	1.372 (11)
N4—C41	1.417 (2)	C34—H34	0.9300
N4—C5	1.463 (2)	C35—C36	1.385 (10)
C5—C6	1.499 (3)	C35—H35	0.9300
C5—H5A	0.9700	C36—H36	0.9300
C5—H5B	0.9700	C41—C42	1.388 (3)
C6—H6A	0.9700	C41—C46	1.393 (3)
C6—H6B	0.9700	C42—C43	1.392 (3)
C17—O17	1.225 (3)	C42—H42	0.9300
C17—C11	1.504 (3)	C43—C44	1.370 (3)
C11—C12	1.378 (3)	C43—H43	0.9300
C11—C16	1.379 (3)	C44—O44	1.372 (2)
C12—C13	1.378 (4)	C44—C45	1.382 (3)
C12—Cl12	1.753 (3)	C45—C46	1.372 (3)
C13—C14	1.359 (4)	C45—H45	0.9300
C13—H13	0.9300	C46—H46	0.9300
C14—C15	1.373 (5)	O44—C441	1.410 (3)
C14—H14	0.9300	C441—H41A	0.9600
C15—C16	1.384 (4)	C441—H41B	0.9600
C15—H15	0.9300	C441—H41C	0.9600

C17—N1—C2	120.55 (18)	C11—C16—C15	121.2 (3)
C37—N1—C2	123.8 (13)	C11—C16—H16	119.4
C17—N1—C6	125.92 (18)	C15—C16—H16	119.4
C37—N1—C6	120.1 (13)	O37—C37—N1	125 (3)
C2—N1—C6	113.53 (16)	O37—C37—C31	116.5 (17)
N1—C2—C3	110.89 (17)	N1—C37—C31	118 (3)
N1—C2—H2A	109.5	C36—C31—C32	117.9 (11)
C3—C2—H2A	109.5	C36—C31—C37	122.0 (14)
N1—C2—H2B	109.5	C32—C31—C37	116.9 (12)
C3—C2—H2B	109.5	C33—C32—C31	122.1 (11)
H2A—C2—H2B	108.0	C33—C32—Cl32	121.7 (12)
N4—C3—C2	110.33 (18)	C31—C32—Cl32	116.1 (11)
N4—C3—H3A	109.6	C34—C33—C32	118.9 (13)
C2—C3—H3A	109.6	C34—C33—H33	120.6
N4—C3—H3B	109.6	C32—C33—H33	120.6
C2—C3—H3B	109.6	C33—C34—C35	120.7 (13)
H3A—C3—H3B	108.1	C33—C34—H34	119.7
C41—N4—C3	117.74 (15)	C35—C34—H34	119.7
C41—N4—C5	115.52 (14)	C34—C35—C36	119.6 (13)
C3—N4—C5	110.63 (15)	C34—C35—H35	120.2
N4—C5—C6	110.57 (17)	C36—C35—H35	120.2
N4—C5—H5A	109.5	C31—C36—C35	120.5 (13)
C6—C5—H5A	109.5	C31—C36—H36	119.8
N4—C5—H5B	109.5	C35—C36—H36	119.8
C6—C5—H5B	109.5	C42—C41—C46	116.81 (17)
H5A—C5—H5B	108.1	C42—C41—N4	123.64 (17)
N1—C6—C5	110.36 (17)	C46—C41—N4	119.46 (16)
N1—C6—H6A	109.6	C41—C42—C43	121.23 (19)
C5—C6—H6A	109.6	C41—C42—H42	119.4
N1—C6—H6B	109.6	C43—C42—H42	119.4
C5—C6—H6B	109.6	C44—C43—C42	120.60 (18)
H6A—C6—H6B	108.1	C44—C43—H43	119.7
O17—C17—N1	123.4 (2)	C42—C43—H43	119.7
O17—C17—C11	118.9 (2)	C43—C44—O44	125.84 (18)
N1—C17—C11	117.7 (2)	C43—C44—C45	118.99 (18)
C12—C11—C16	117.7 (2)	O44—C44—C45	115.18 (18)
C12—C11—C17	121.8 (2)	C46—C45—C44	120.32 (19)
C16—C11—C17	120.2 (2)	C46—C45—H45	119.8
C13—C12—C11	121.5 (3)	C44—C45—H45	119.8
C13—C12—Cl12	119.0 (2)	C45—C46—C41	122.02 (18)
C11—C12—Cl12	119.53 (19)	C45—C46—H46	119.0
C14—C13—C12	119.8 (3)	C41—C46—H46	119.0
C14—C13—H13	120.1	C44—O44—C441	117.58 (18)
C12—C13—H13	120.1	O44—C441—H41A	109.5
C13—C14—C15	120.4 (3)	O44—C441—H41B	109.5
C13—C14—H14	119.8	H41A—C441—H41B	109.5
C15—C14—H14	119.8	O44—C441—H41C	109.5
C14—C15—C16	119.4 (3)	H41A—C441—H41C	109.5
C14—C15—H15	120.3	H41B—C441—H41C	109.5
C16—C15—H15	120.3

C17—N1—C2—C3	127.9 (2)	C6—N1—C37—O37	168 (2)
C37—N1—C2—C3	108.7 (12)	C17—N1—C37—C31	99 (5)
C6—N1—C2—C3	−52.9 (3)	C2—N1—C37—C31	−176.6 (10)
N1—C2—C3—N4	54.7 (3)	C6—N1—C37—C31	−16 (2)
C2—C3—N4—C41	165.51 (16)	O37—C37—C31—C36	−73 (4)
C2—C3—N4—C5	−58.6 (2)	N1—C37—C31—C36	110 (3)
C41—N4—C5—C6	−163.56 (16)	O37—C37—C31—C32	86 (3)
C3—N4—C5—C6	59.5 (2)	N1—C37—C31—C32	−90 (3)
C17—N1—C6—C5	−127.5 (2)	C36—C31—C32—C33	−5 (2)
C37—N1—C6—C5	−109.0 (12)	C37—C31—C32—C33	−165 (3)
C2—N1—C6—C5	53.4 (2)	C36—C31—C32—Cl32	171 (3)
N4—C5—C6—N1	−55.8 (2)	C37—C31—C32—Cl32	11 (4)
C37—N1—C17—O17	107 (5)	C31—C32—C33—C34	0 (3)
C2—N1—C17—O17	0.2 (4)	Cl32—C32—C33—C34	−176 (4)
C6—N1—C17—O17	−178.8 (2)	C32—C33—C34—C35	2 (6)
C37—N1—C17—C11	−73 (5)	C33—C34—C35—C36	1 (8)
C2—N1—C17—C11	−179.8 (2)	C32—C31—C36—C35	8 (5)
C6—N1—C17—C11	1.2 (3)	C37—C31—C36—C35	167 (5)
O17—C17—C11—C12	−89.1 (3)	C34—C35—C36—C31	−6 (8)
N1—C17—C11—C12	90.9 (3)	C3—N4—C41—C42	2.8 (3)
O17—C17—C11—C16	85.4 (3)	C5—N4—C41—C42	−131.0 (2)
N1—C17—C11—C16	−94.6 (3)	C3—N4—C41—C46	−173.72 (19)
C16—C11—C12—C13	−2.1 (4)	C5—N4—C41—C46	52.5 (2)
C17—C11—C12—C13	172.5 (3)	C46—C41—C42—C43	−1.4 (3)
C16—C11—C12—Cl12	176.4 (2)	N4—C41—C42—C43	−178.03 (18)
C17—C11—C12—Cl12	−8.9 (3)	C41—C42—C43—C44	0.2 (3)
C11—C12—C13—C14	1.0 (5)	C42—C43—C44—O44	−179.13 (19)
Cl12—C12—C13—C14	−177.5 (3)	C42—C43—C44—C45	0.7 (3)
C12—C13—C14—C15	1.1 (5)	C43—C44—C45—C46	−0.4 (3)
C13—C14—C15—C16	−2.1 (5)	O44—C44—C45—C46	179.50 (19)
C12—C11—C16—C15	1.2 (4)	C44—C45—C46—C41	−0.9 (3)
C17—C11—C16—C15	−173.6 (3)	C42—C41—C46—C45	1.8 (3)
C14—C15—C16—C11	0.9 (4)	N4—C41—C46—C45	178.55 (19)
C17—N1—C37—O37	−76 (5)	C43—C44—O44—C441	6.1 (3)
C2—N1—C37—O37	7 (3)	C45—C44—O44—C441	−173.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O17ⁱ	0.97	2.61	3.574 (3)	175
C2—H2A···Cg1ⁱ	0.97	2.84	3.648 (3)	142
C15—H15···Cg2ⁱⁱ	0.93	2.72	3.610 (4)	161

Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) −x+3/2, y−1/2, z.

1-(2-Bromoobenzoyl)-4-(4-methoxyphenyl)piperazine (IV) top

Crystal data top

C₁₈H₁₉BrN₂O₂	D_x = 1.481 Mg m⁻³
M_r = 375.26	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 10112 reflections
a = 12.9119 (14) Å	θ = 2.2–30.6°
b = 13.3664 (16) Å	µ = 2.45 mm⁻¹
c = 19.5019 (19) Å	T = 293 K
V = 3365.7 (6) Å³	Block, colourless
Z = 8	0.22 × 0.21 × 0.18 mm
F(000) = 1536

Data collection top

Bruker D8 Quest diffractometer	4262 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3135 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
φ and ω scans	θ_max = 28.6°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2015	h = −17→17
T_min = 0.538, T_max = 0.643	k = −17→17
47663 measured reflections	l = −25→26

Refinement top

Refinement on F²	Primary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.131	w = 1/[σ²(F_o²) + (0.0626P)² + 2.0275P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
4262 reflections	Δρ_max = 0.54 e Å⁻³
209 parameters	Δρ_min = −0.64 e Å⁻³
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.68078 (15)	0.28092 (16)	0.41388 (11)	0.0487 (5)
C2	0.57868 (19)	0.2622 (2)	0.44328 (15)	0.0590 (7)
H2A	0.5856	0.2493	0.4920	0.071*
H2B	0.5487	0.2032	0.4221	0.071*
C3	0.50766 (18)	0.3504 (2)	0.43240 (12)	0.0519 (6)
H3A	0.4388	0.3340	0.4487	0.062*
H3B	0.5328	0.4072	0.4584	0.062*
N4	0.50316 (13)	0.37615 (15)	0.35983 (9)	0.0419 (4)
C5	0.60654 (17)	0.4002 (2)	0.33390 (12)	0.0473 (5)
H5A	0.6341	0.4572	0.3587	0.057*
H5B	0.6021	0.4180	0.2858	0.057*
C6	0.67798 (19)	0.3122 (2)	0.34234 (12)	0.0521 (6)
H6A	0.6541	0.2572	0.3140	0.062*
H6B	0.7471	0.3304	0.3274	0.062*
C17	0.76628 (19)	0.2666 (2)	0.45102 (13)	0.0512 (6)
O17	0.76512 (15)	0.2365 (2)	0.50994 (12)	0.0946 (9)
C11	0.86917 (17)	0.28780 (19)	0.41712 (12)	0.0454 (5)
C12	0.91561 (19)	0.3799 (2)	0.42084 (11)	0.0497 (6)
Br12	0.84357 (3)	0.49042 (2)	0.45966 (2)	0.07101 (15)
C13	1.0151 (2)	0.3952 (3)	0.39598 (13)	0.0650 (8)
H13	1.0461	0.4579	0.3993	0.078*
C14	1.0668 (2)	0.3174 (4)	0.36663 (16)	0.0789 (11)
H14	1.1339	0.3267	0.3504	0.095*
C15	1.0212 (3)	0.2262 (3)	0.36096 (17)	0.0798 (10)
H15	1.0563	0.1741	0.3396	0.096*
C16	0.9229 (2)	0.2107 (2)	0.38671 (15)	0.0650 (7)
H16	0.8928	0.1477	0.3835	0.078*
C41	0.42268 (16)	0.44128 (16)	0.33883 (11)	0.0390 (5)
C42	0.35098 (18)	0.4829 (2)	0.38304 (13)	0.0491 (6)
H42	0.3559	0.4695	0.4297	0.059*
C43	0.27162 (18)	0.5446 (2)	0.35948 (13)	0.0527 (6)
H43	0.2243	0.5715	0.3903	0.063*
C44	0.26318 (17)	0.56563 (19)	0.29071 (11)	0.0450 (5)
C45	0.3328 (2)	0.5236 (2)	0.24572 (13)	0.0527 (6)
H45	0.3271	0.5368	0.1990	0.063*
C46	0.41060 (19)	0.4627 (2)	0.26907 (12)	0.0498 (6)
H46	0.4565	0.4348	0.2377	0.060*
O44	0.18982 (15)	0.62631 (15)	0.26166 (10)	0.0658 (5)
C441	0.1221 (3)	0.6779 (3)	0.30621 (19)	0.0798 (10)
H41A	0.0799	0.7232	0.2801	0.120*
H41B	0.1618	0.7148	0.3392	0.120*
H41C	0.0785	0.6307	0.3295	0.120*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0384 (10)	0.0551 (12)	0.0527 (11)	0.0020 (9)	−0.0042 (8)	0.0126 (9)
C2	0.0415 (13)	0.0652 (17)	0.0704 (16)	−0.0037 (12)	−0.0026 (12)	0.0291 (14)
C3	0.0411 (12)	0.0667 (16)	0.0478 (12)	0.0014 (12)	0.0032 (10)	0.0187 (12)
N4	0.0346 (9)	0.0492 (11)	0.0420 (9)	0.0031 (8)	−0.0005 (7)	0.0078 (8)
C5	0.0384 (11)	0.0606 (15)	0.0429 (11)	0.0028 (11)	0.0015 (9)	0.0121 (11)
C6	0.0410 (12)	0.0690 (17)	0.0462 (12)	0.0091 (12)	−0.0034 (10)	0.0019 (12)
C17	0.0444 (13)	0.0526 (14)	0.0566 (14)	0.0029 (11)	−0.0065 (10)	0.0121 (11)
O17	0.0535 (11)	0.158 (3)	0.0728 (14)	0.0043 (14)	−0.0081 (10)	0.0598 (15)
C11	0.0395 (11)	0.0524 (14)	0.0442 (12)	0.0042 (10)	−0.0099 (9)	0.0036 (10)
C12	0.0519 (13)	0.0615 (15)	0.0357 (11)	−0.0014 (12)	−0.0091 (9)	0.0028 (10)
Br12	0.1004 (3)	0.0570 (2)	0.0557 (2)	−0.00293 (15)	−0.00205 (15)	−0.01036 (12)
C13	0.0542 (15)	0.091 (2)	0.0494 (14)	−0.0214 (16)	−0.0125 (12)	0.0166 (14)
C14	0.0434 (15)	0.134 (3)	0.0594 (17)	0.0089 (19)	−0.0024 (13)	0.025 (2)
C15	0.0631 (19)	0.107 (3)	0.070 (2)	0.034 (2)	−0.0001 (15)	0.0001 (19)
C16	0.0592 (16)	0.0640 (17)	0.0720 (18)	0.0157 (14)	−0.0086 (13)	−0.0041 (14)
C41	0.0361 (10)	0.0400 (11)	0.0409 (11)	−0.0010 (9)	−0.0020 (8)	0.0017 (9)
C42	0.0418 (12)	0.0658 (16)	0.0398 (12)	0.0062 (11)	0.0061 (9)	0.0092 (11)
C43	0.0413 (13)	0.0646 (16)	0.0520 (13)	0.0094 (12)	0.0085 (10)	0.0035 (12)
C44	0.0380 (11)	0.0454 (13)	0.0514 (12)	0.0051 (10)	−0.0051 (9)	−0.0012 (10)
C45	0.0575 (15)	0.0621 (15)	0.0386 (11)	0.0137 (12)	−0.0058 (10)	−0.0035 (11)
C46	0.0512 (13)	0.0608 (15)	0.0373 (11)	0.0171 (12)	−0.0018 (10)	−0.0071 (10)
O44	0.0611 (11)	0.0735 (13)	0.0629 (11)	0.0303 (10)	−0.0045 (9)	0.0034 (10)
C441	0.0693 (19)	0.081 (2)	0.089 (2)	0.0359 (18)	0.0017 (17)	−0.0007 (18)

Geometric parameters (Å, º) top

N1—C17	1.334 (3)	C13—C14	1.363 (5)
N1—C6	1.457 (3)	C13—H13	0.9300
N1—C2	1.459 (3)	C14—C15	1.358 (5)
C2—C3	1.508 (4)	C14—H14	0.9300
C2—H2A	0.9700	C15—C16	1.381 (5)
C2—H2B	0.9700	C15—H15	0.9300
C3—N4	1.458 (3)	C16—H16	0.9300
C3—H3A	0.9700	C41—C42	1.382 (3)
C3—H3B	0.9700	C41—C46	1.399 (3)
N4—C41	1.416 (3)	C42—C43	1.393 (3)
N4—C5	1.463 (3)	C42—H42	0.9300
C5—C6	1.504 (3)	C43—C44	1.375 (3)
C5—H5A	0.9700	C43—H43	0.9300
C5—H5B	0.9700	C44—O44	1.370 (3)
C6—H6A	0.9700	C44—C45	1.376 (3)
C6—H6B	0.9700	C45—C46	1.371 (4)
C17—O17	1.218 (3)	C45—H45	0.9300
C17—C11	1.511 (3)	C46—H46	0.9300
C11—C12	1.371 (4)	O44—C441	1.413 (4)
C11—C16	1.377 (4)	C441—H41A	0.9600
C12—C13	1.389 (4)	C441—H41B	0.9600
C12—Br12	1.903 (3)	C441—H41C	0.9600

C17—N1—C6	125.6 (2)	C13—C12—Br12	118.4 (2)
C17—N1—C2	120.6 (2)	C14—C13—C12	119.2 (3)
C6—N1—C2	113.77 (19)	C14—C13—H13	120.4
N1—C2—C3	111.1 (2)	C12—C13—H13	120.4
N1—C2—H2A	109.4	C15—C14—C13	120.4 (3)
C3—C2—H2A	109.4	C15—C14—H14	119.8
N1—C2—H2B	109.4	C13—C14—H14	119.8
C3—C2—H2B	109.4	C14—C15—C16	120.3 (3)
H2A—C2—H2B	108.0	C14—C15—H15	119.9
N4—C3—C2	110.2 (2)	C16—C15—H15	119.9
N4—C3—H3A	109.6	C11—C16—C15	120.5 (3)
C2—C3—H3A	109.6	C11—C16—H16	119.8
N4—C3—H3B	109.6	C15—C16—H16	119.8
C2—C3—H3B	109.6	C42—C41—C46	116.7 (2)
H3A—C3—H3B	108.1	C42—C41—N4	124.0 (2)
C41—N4—C3	117.09 (18)	C46—C41—N4	119.25 (19)
C41—N4—C5	115.76 (18)	C41—C42—C43	121.7 (2)
C3—N4—C5	110.56 (17)	C41—C42—H42	119.2
N4—C5—C6	110.5 (2)	C43—C42—H42	119.2
N4—C5—H5A	109.6	C44—C43—C42	120.1 (2)
C6—C5—H5A	109.6	C44—C43—H43	120.0
N4—C5—H5B	109.6	C42—C43—H43	120.0
C6—C5—H5B	109.6	O44—C44—C43	125.4 (2)
H5A—C5—H5B	108.1	O44—C44—C45	115.4 (2)
N1—C6—C5	110.1 (2)	C43—C44—C45	119.1 (2)
N1—C6—H6A	109.6	C46—C45—C44	120.6 (2)
C5—C6—H6A	109.6	C46—C45—H45	119.7
N1—C6—H6B	109.6	C44—C45—H45	119.7
C5—C6—H6B	109.6	C45—C46—C41	121.7 (2)
H6A—C6—H6B	108.1	C45—C46—H46	119.1
O17—C17—N1	123.3 (2)	C41—C46—H46	119.1
O17—C17—C11	119.1 (2)	C44—O44—C441	117.6 (2)
N1—C17—C11	117.6 (2)	O44—C441—H41A	109.5
C12—C11—C16	118.3 (2)	O44—C441—H41B	109.5
C12—C11—C17	122.0 (2)	H41A—C441—H41B	109.5
C16—C11—C17	119.4 (2)	O44—C441—H41C	109.5
C11—C12—C13	121.3 (3)	H41A—C441—H41C	109.5
C11—C12—Br12	120.29 (19)	H41B—C441—H41C	109.5

C17—N1—C2—C3	129.3 (3)	Br12—C12—C13—C14	−178.5 (2)
C6—N1—C2—C3	−52.6 (3)	C12—C13—C14—C15	0.8 (4)
N1—C2—C3—N4	54.3 (3)	C13—C14—C15—C16	−1.9 (5)
C2—C3—N4—C41	165.8 (2)	C12—C11—C16—C15	0.2 (4)
C2—C3—N4—C5	−58.7 (3)	C17—C11—C16—C15	−174.1 (3)
C41—N4—C5—C6	−163.87 (19)	C14—C15—C16—C11	1.4 (5)
C3—N4—C5—C6	60.0 (3)	C3—N4—C41—C42	1.7 (3)
C17—N1—C6—C5	−128.8 (3)	C5—N4—C41—C42	−131.6 (2)
C2—N1—C6—C5	53.1 (3)	C3—N4—C41—C46	−175.5 (2)
N4—C5—C6—N1	−56.0 (3)	C5—N4—C41—C46	51.3 (3)
C6—N1—C17—O17	−176.9 (3)	C46—C41—C42—C43	−1.1 (4)
C2—N1—C17—O17	1.1 (4)	N4—C41—C42—C43	−178.3 (2)
C6—N1—C17—C11	2.2 (4)	C41—C42—C43—C44	−0.2 (4)
C2—N1—C17—C11	−179.9 (2)	C42—C43—C44—O44	−178.8 (2)
O17—C17—C11—C12	−89.6 (3)	C42—C43—C44—C45	1.2 (4)
N1—C17—C11—C12	91.3 (3)	O44—C44—C45—C46	179.1 (3)
O17—C17—C11—C16	84.4 (4)	C43—C44—C45—C46	−0.9 (4)
N1—C17—C11—C16	−94.7 (3)	C44—C45—C46—C41	−0.4 (4)
C16—C11—C12—C13	−1.3 (4)	C42—C41—C46—C45	1.4 (4)
C17—C11—C12—C13	172.8 (2)	N4—C41—C46—C45	178.7 (2)
C16—C11—C12—Br12	178.01 (19)	C43—C44—O44—C441	5.3 (4)
C17—C11—C12—Br12	−7.9 (3)	C45—C44—O44—C441	−174.7 (3)
C11—C12—C13—C14	0.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O17ⁱ	0.97	2.56	3.524 (3)	171
C2—H2A···Cg1ⁱ	0.97	2.82	3.630 (3)	142
C15—H15···Cg2ⁱⁱ	0.93	2.68	3.579 (4)	164

Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) −x+3/2, y−1/2, z.

1-(2-Iodobenzoyl)-4-(4-methoxyphenyl)piperazine (V) top

Crystal data top

C₁₈H₁₉IN₂O₂	D_x = 1.602 Mg m⁻³
M_r = 422.25	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 3838 reflections
a = 12.7671 (13) Å	θ = 2.6–27.7°
b = 13.5429 (12) Å	µ = 1.84 mm⁻¹
c = 20.2542 (16) Å	T = 293 K
V = 3502.0 (5) Å³	Block, orange
Z = 8	0.48 × 0.42 × 0.38 mm
F(000) = 1680

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD	3838 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3062 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω scans	θ_max = 27.7°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −16→9
T_min = 0.408, T_max = 0.497	k = −17→12
14215 measured reflections	l = −25→26

Refinement top

Refinement on F²	Primary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.068	H-atom parameters constrained
wR(F²) = 0.146	w = 1/[σ²(F_o²) + 37.1584P] where P = (F_o² + 2F_c²)/3
S = 1.18	(Δ/σ)_max < 0.001
3838 reflections	Δρ_max = 1.27 e Å⁻³
209 parameters	Δρ_min = −2.19 e Å⁻³
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.6767 (5)	0.2532 (5)	0.4083 (3)	0.0444 (15)
C2	0.5718 (6)	0.2371 (7)	0.4337 (5)	0.061 (3)
H2A	0.5755	0.2250	0.4808	0.073*
H2B	0.5421	0.1789	0.4130	0.073*
C3	0.5017 (6)	0.3231 (7)	0.4213 (4)	0.052 (2)
H3A	0.4312	0.3075	0.4358	0.062*
H3B	0.5261	0.3796	0.4465	0.062*
N4	0.5006 (4)	0.3478 (4)	0.3506 (3)	0.0390 (14)
C5	0.6074 (5)	0.3718 (6)	0.3295 (4)	0.0445 (18)
H5A	0.6329	0.4278	0.3545	0.053*
H5B	0.6070	0.3899	0.2831	0.053*
C6	0.6796 (6)	0.2846 (6)	0.3397 (4)	0.0453 (18)
H6A	0.6582	0.2305	0.3114	0.054*
H6B	0.7506	0.3030	0.3279	0.054*
C17	0.7611 (6)	0.2329 (6)	0.4454 (4)	0.0467 (18)
O17	0.7546 (5)	0.1949 (5)	0.5001 (3)	0.0697 (19)
C11	0.8673 (5)	0.2557 (6)	0.4170 (4)	0.0386 (15)
C12	0.9137 (6)	0.3478 (5)	0.4227 (3)	0.0397 (16)
I12	0.83463 (5)	0.46721 (5)	0.46533 (3)	0.0580 (2)
C13	1.0151 (6)	0.3627 (6)	0.4001 (4)	0.0489 (19)
H13	1.0461	0.4246	0.4041	0.059*
C14	1.0693 (7)	0.2870 (8)	0.3723 (5)	0.064 (3)
H14	1.1371	0.2976	0.3571	0.077*
C15	1.0243 (8)	0.1942 (9)	0.3665 (5)	0.075 (3)
H15	1.0614	0.1423	0.3476	0.090*
C16	0.9247 (7)	0.1806 (7)	0.3889 (5)	0.063 (2)
H16	0.8945	0.1184	0.3851	0.076*
C41	0.4211 (5)	0.4122 (5)	0.3293 (3)	0.0362 (15)
C42	0.3441 (6)	0.4490 (6)	0.3699 (4)	0.0471 (19)
H42	0.3446	0.4326	0.4145	0.057*
C43	0.2655 (6)	0.5101 (6)	0.3459 (4)	0.0446 (18)
H43	0.2138	0.5329	0.3744	0.053*
C44	0.2632 (6)	0.5375 (6)	0.2800 (4)	0.0427 (16)
C45	0.3388 (6)	0.5001 (6)	0.2392 (3)	0.0473 (19)
H45	0.3379	0.5169	0.1947	0.057*
C46	0.4155 (6)	0.4388 (6)	0.2622 (4)	0.0471 (19)
H46	0.4651	0.4141	0.2329	0.056*
O44	0.1910 (5)	0.5988 (5)	0.2516 (3)	0.0615 (16)
C441	0.1209 (8)	0.6484 (8)	0.2934 (5)	0.078 (3)
H41A	0.0746	0.6886	0.2674	0.117*
H41B	0.1595	0.6896	0.3234	0.117*
H41C	0.0807	0.6011	0.3179	0.117*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.036 (3)	0.044 (3)	0.053 (4)	0.000 (3)	−0.004 (3)	0.022 (3)
C2	0.037 (4)	0.076 (6)	0.070 (6)	−0.001 (4)	−0.004 (4)	0.037 (5)
C3	0.037 (4)	0.071 (6)	0.048 (4)	−0.001 (4)	0.006 (3)	0.029 (4)
N4	0.030 (3)	0.045 (3)	0.042 (3)	0.000 (3)	0.000 (2)	0.013 (3)
C5	0.034 (4)	0.060 (5)	0.040 (4)	0.002 (3)	0.000 (3)	0.017 (4)
C6	0.037 (4)	0.055 (5)	0.044 (4)	0.005 (3)	−0.001 (3)	0.010 (4)
C17	0.037 (4)	0.046 (4)	0.057 (5)	−0.006 (3)	−0.009 (4)	0.012 (4)
O17	0.048 (3)	0.094 (5)	0.067 (4)	−0.001 (3)	−0.008 (3)	0.039 (4)
C11	0.034 (3)	0.041 (4)	0.041 (4)	0.000 (3)	−0.008 (3)	0.003 (3)
C12	0.041 (4)	0.042 (4)	0.036 (4)	0.003 (3)	−0.009 (3)	−0.001 (3)
I12	0.0702 (4)	0.0501 (3)	0.0538 (3)	0.0045 (3)	−0.0031 (3)	−0.0162 (3)
C13	0.047 (4)	0.056 (5)	0.044 (4)	−0.012 (4)	−0.007 (4)	−0.001 (4)
C14	0.036 (4)	0.098 (8)	0.059 (5)	0.005 (5)	0.003 (4)	0.001 (5)
C15	0.056 (6)	0.088 (8)	0.081 (7)	0.036 (6)	−0.007 (5)	−0.017 (6)
C16	0.055 (5)	0.057 (6)	0.077 (6)	0.004 (4)	−0.012 (5)	−0.008 (5)
C41	0.031 (3)	0.038 (4)	0.040 (4)	−0.002 (3)	−0.002 (3)	0.000 (3)
C42	0.041 (4)	0.061 (5)	0.039 (4)	0.003 (4)	0.008 (3)	0.015 (4)
C43	0.036 (4)	0.044 (4)	0.053 (4)	0.003 (3)	0.010 (3)	0.006 (3)
C44	0.036 (4)	0.043 (4)	0.049 (4)	0.003 (3)	−0.005 (3)	0.002 (3)
C45	0.059 (5)	0.054 (5)	0.030 (3)	0.012 (4)	−0.006 (3)	0.002 (3)
C46	0.048 (4)	0.055 (5)	0.038 (4)	0.017 (4)	0.002 (3)	−0.003 (3)
O44	0.057 (4)	0.066 (4)	0.062 (4)	0.026 (3)	−0.004 (3)	0.008 (3)
C441	0.062 (6)	0.084 (7)	0.089 (7)	0.032 (6)	−0.001 (6)	−0.001 (6)

Geometric parameters (Å, º) top

N1—C17	1.342 (9)	C13—C14	1.358 (12)
N1—C2	1.452 (9)	C13—H13	0.9300
N1—C6	1.453 (9)	C14—C15	1.387 (14)
C2—C3	1.490 (11)	C14—H14	0.9300
C2—H2A	0.9700	C15—C16	1.362 (13)
C2—H2B	0.9700	C15—H15	0.9300
C3—N4	1.471 (9)	C16—H16	0.9300
C3—H3A	0.9700	C41—C42	1.375 (10)
C3—H3B	0.9700	C41—C46	1.407 (10)
N4—C41	1.406 (9)	C42—C43	1.388 (10)
N4—C5	1.464 (8)	C42—H42	0.9300
C5—C6	1.512 (10)	C43—C44	1.386 (10)
C5—H5A	0.9700	C43—H43	0.9300
C5—H5B	0.9700	C44—O44	1.368 (9)
C6—H6A	0.9700	C44—C45	1.368 (10)
C6—H6B	0.9700	C45—C46	1.365 (10)
C17—O17	1.224 (9)	C45—H45	0.9300
C17—C11	1.505 (10)	C46—H46	0.9300
C11—C16	1.377 (11)	O44—C441	1.403 (10)
C11—C12	1.385 (10)	C441—H41A	0.9600
C12—C13	1.389 (10)	C441—H41B	0.9600
C12—I12	2.093 (7)	C441—H41C	0.9600

C17—N1—C2	120.8 (6)	C13—C12—I12	118.2 (6)
C17—N1—C6	125.0 (6)	C14—C13—C12	120.1 (8)
C2—N1—C6	114.0 (6)	C14—C13—H13	119.9
N1—C2—C3	112.1 (7)	C12—C13—H13	119.9
N1—C2—H2A	109.2	C13—C14—C15	120.5 (8)
C3—C2—H2A	109.2	C13—C14—H14	119.7
N1—C2—H2B	109.2	C15—C14—H14	119.7
C3—C2—H2B	109.2	C16—C15—C14	118.7 (9)
H2A—C2—H2B	107.9	C16—C15—H15	120.6
N4—C3—C2	110.3 (7)	C14—C15—H15	120.6
N4—C3—H3A	109.6	C15—C16—C11	122.3 (9)
C2—C3—H3A	109.6	C15—C16—H16	118.8
N4—C3—H3B	109.6	C11—C16—H16	118.8
C2—C3—H3B	109.6	C42—C41—N4	123.9 (6)
H3A—C3—H3B	108.1	C42—C41—C46	116.6 (7)
C41—N4—C5	116.5 (6)	N4—C41—C46	119.4 (6)
C41—N4—C3	116.5 (6)	C41—C42—C43	121.6 (7)
C5—N4—C3	109.0 (6)	C41—C42—H42	119.2
N4—C5—C6	110.8 (6)	C43—C42—H42	119.2
N4—C5—H5A	109.5	C44—C43—C42	120.8 (7)
C6—C5—H5A	109.5	C44—C43—H43	119.6
N4—C5—H5B	109.5	C42—C43—H43	119.6
C6—C5—H5B	109.5	O44—C44—C45	116.5 (7)
H5A—C5—H5B	108.1	O44—C44—C43	125.6 (7)
N1—C6—C5	110.1 (6)	C45—C44—C43	117.9 (7)
N1—C6—H6A	109.6	C46—C45—C44	121.7 (7)
C5—C6—H6A	109.6	C46—C45—H45	119.2
N1—C6—H6B	109.6	C44—C45—H45	119.2
C5—C6—H6B	109.6	C45—C46—C41	121.4 (7)
H6A—C6—H6B	108.2	C45—C46—H46	119.3
O17—C17—N1	122.6 (7)	C41—C46—H46	119.3
O17—C17—C11	119.6 (7)	C44—O44—C441	117.8 (7)
N1—C17—C11	117.8 (6)	O44—C441—H41A	109.5
C16—C11—C12	118.2 (7)	O44—C441—H41B	109.5
C16—C11—C17	119.1 (7)	H41A—C441—H41B	109.5
C12—C11—C17	122.6 (7)	O44—C441—H41C	109.5
C11—C12—C13	120.1 (7)	H41A—C441—H41C	109.5
C11—C12—I12	121.6 (5)	H41B—C441—H41C	109.5

C17—N1—C2—C3	133.1 (8)	I12—C12—C13—C14	179.8 (6)
C6—N1—C2—C3	−51.4 (11)	C12—C13—C14—C15	−0.3 (13)
N1—C2—C3—N4	54.7 (10)	C13—C14—C15—C16	0.3 (15)
C2—C3—N4—C41	166.2 (6)	C14—C15—C16—C11	0.1 (15)
C2—C3—N4—C5	−59.6 (9)	C12—C11—C16—C15	−0.4 (13)
C41—N4—C5—C6	−165.0 (6)	C17—C11—C16—C15	−175.2 (8)
C3—N4—C5—C6	60.7 (8)	C5—N4—C41—C42	−133.4 (8)
C17—N1—C6—C5	−133.5 (8)	C3—N4—C41—C42	−2.6 (10)
C2—N1—C6—C5	51.2 (9)	C5—N4—C41—C46	49.2 (10)
N4—C5—C6—N1	−56.1 (8)	C3—N4—C41—C46	−180.0 (7)
C2—N1—C17—O17	4.4 (13)	N4—C41—C42—C43	−178.1 (7)
C6—N1—C17—O17	−170.6 (8)	C46—C41—C42—C43	−0.6 (12)
C2—N1—C17—C11	−177.2 (8)	C41—C42—C43—C44	−1.1 (12)
C6—N1—C17—C11	7.8 (12)	C42—C43—C44—O44	−178.5 (7)
O17—C17—C11—C16	79.4 (11)	C42—C43—C44—C45	1.9 (12)
N1—C17—C11—C16	−99.0 (9)	O44—C44—C45—C46	179.5 (7)
O17—C17—C11—C12	−95.1 (10)	C43—C44—C45—C46	−0.9 (12)
N1—C17—C11—C12	86.5 (9)	C44—C45—C46—C41	−0.8 (13)
C16—C11—C12—C13	0.4 (11)	C42—C41—C46—C45	1.6 (12)
C17—C11—C12—C13	174.9 (7)	N4—C41—C46—C45	179.2 (7)
C16—C11—C12—I12	−179.4 (6)	C45—C44—O44—C441	−171.8 (8)
C17—C11—C12—I12	−4.9 (9)	C43—C44—O44—C441	8.6 (13)
C11—C12—C13—C14	0.0 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O17ⁱ	0.97	2.60	3.542 (10)	164
C2—H2A···Cg1ⁱ	0.97	2.87	3.719 (11)	147
C15—H15···Cg2ⁱⁱ	0.93	2.73	3.656 (12)	172

Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) −x+3/2, y−1/2, z.

1-(2-Hydroxybenzoyl)-4-(4-methoxyphenyl)piperazine (VI) top

Crystal data top

C₁₈H₂₀N₂O₃	D_x = 1.329 Mg m⁻³
M_r = 312.36	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 3474 reflections
a = 9.7265 (6) Å	θ = 2.7–27.9°
b = 12.9084 (9) Å	µ = 0.09 mm⁻¹
c = 24.861 (1) Å	T = 293 K
V = 3121.4 (3) Å³	Plate, yellow
Z = 8	0.50 × 0.40 × 0.16 mm
F(000) = 1328

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD	3474 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2492 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω scans	θ_max = 27.9°, θ_min = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −12→5
T_min = 0.917, T_max = 0.986	k = −13→16
11981 measured reflections	l = −31→31

Refinement top

Refinement on F²	Primary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.038P)² + 0.9467P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3474 reflections	Δρ_max = 0.16 e Å⁻³
212 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.65619 (12)	0.42451 (10)	0.35751 (5)	0.0368 (3)
C2	0.64088 (15)	0.36047 (14)	0.40542 (6)	0.0448 (4)
H2A	0.5498	0.3298	0.4057	0.054*
H2B	0.6498	0.4035	0.4372	0.054*
C3	0.74781 (15)	0.27547 (13)	0.40711 (6)	0.0432 (4)
H3A	0.7390	0.2367	0.4404	0.052*
H3B	0.7334	0.2281	0.3774	0.052*
N4	0.88519 (12)	0.32027 (10)	0.40359 (5)	0.0384 (3)
C5	0.89929 (15)	0.38044 (13)	0.35376 (6)	0.0429 (4)
H5A	0.8865	0.3351	0.3230	0.051*
H5B	0.9912	0.4094	0.3517	0.051*
C6	0.79474 (14)	0.46694 (12)	0.35178 (6)	0.0401 (4)
H6A	0.8126	0.5159	0.3806	0.048*
H6B	0.8023	0.5035	0.3178	0.048*
C17	0.54733 (14)	0.44756 (11)	0.32643 (5)	0.0324 (3)
O17	0.43132 (10)	0.41265 (8)	0.33693 (4)	0.0404 (3)
C11	0.56584 (14)	0.52022 (11)	0.28009 (6)	0.0329 (3)
C12	0.64738 (14)	0.49883 (11)	0.23528 (6)	0.0349 (3)
O12	0.71754 (12)	0.40749 (9)	0.23434 (4)	0.0461 (3)
H12	0.789 (2)	0.4130 (15)	0.2100 (8)	0.069*
C13	0.65334 (16)	0.56961 (12)	0.19321 (6)	0.0412 (4)
H13	0.7060	0.5548	0.1629	0.049*
C14	0.58174 (17)	0.66145 (13)	0.19606 (6)	0.0471 (4)
H14	0.5888	0.7092	0.1682	0.057*
C15	0.49942 (17)	0.68344 (13)	0.23996 (7)	0.0483 (4)
H15	0.4501	0.7451	0.2415	0.058*
C16	0.49147 (15)	0.61263 (12)	0.28139 (6)	0.0408 (4)
H16	0.4354	0.6268	0.3108	0.049*
C41	0.99766 (14)	0.25442 (12)	0.41654 (6)	0.0355 (3)
C42	0.98274 (16)	0.15034 (13)	0.42966 (6)	0.0419 (4)
H42	0.8956	0.1207	0.4291	0.050*
C43	1.09521 (16)	0.08983 (13)	0.44351 (6)	0.0450 (4)
H43	1.0825	0.0204	0.4523	0.054*
C44	1.22554 (15)	0.13157 (13)	0.44442 (6)	0.0407 (4)
C45	1.24231 (15)	0.23528 (13)	0.43236 (7)	0.0451 (4)
H45	1.3295	0.2648	0.4335	0.054*
C46	1.13003 (15)	0.29544 (13)	0.41862 (7)	0.0446 (4)
H46	1.1432	0.3651	0.4106	0.054*
O44	1.33074 (12)	0.06448 (10)	0.45724 (5)	0.0569 (3)
C441	1.46702 (17)	0.10399 (16)	0.45482 (7)	0.0576 (5)
H41A	1.5311	0.0492	0.4622	0.086*
H41B	1.4778	0.1579	0.4811	0.086*
H41C	1.4842	0.1315	0.4196	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0309 (6)	0.0442 (7)	0.0354 (6)	−0.0022 (5)	−0.0010 (5)	0.0077 (6)
C2	0.0336 (8)	0.0634 (11)	0.0374 (8)	0.0013 (7)	0.0034 (6)	0.0138 (8)
C3	0.0354 (8)	0.0504 (10)	0.0437 (8)	−0.0035 (7)	0.0016 (7)	0.0152 (7)
N4	0.0308 (6)	0.0418 (7)	0.0425 (7)	−0.0002 (5)	0.0028 (5)	0.0091 (6)
C5	0.0340 (7)	0.0480 (10)	0.0466 (9)	−0.0019 (7)	0.0044 (6)	0.0096 (7)
C6	0.0340 (8)	0.0407 (9)	0.0454 (8)	−0.0053 (6)	−0.0044 (6)	0.0076 (7)
C17	0.0336 (7)	0.0309 (8)	0.0327 (7)	0.0007 (6)	0.0008 (6)	−0.0043 (6)
O17	0.0318 (5)	0.0467 (6)	0.0428 (6)	−0.0038 (4)	−0.0005 (4)	0.0058 (5)
C11	0.0317 (7)	0.0342 (8)	0.0328 (7)	−0.0023 (6)	−0.0033 (6)	0.0008 (6)
C12	0.0340 (7)	0.0356 (8)	0.0352 (8)	−0.0029 (6)	−0.0019 (6)	−0.0021 (6)
O12	0.0488 (7)	0.0439 (7)	0.0456 (6)	0.0073 (5)	0.0128 (5)	0.0021 (5)
C13	0.0437 (9)	0.0464 (9)	0.0334 (8)	−0.0071 (7)	0.0001 (6)	0.0016 (7)
C14	0.0597 (10)	0.0429 (9)	0.0388 (8)	−0.0052 (8)	−0.0061 (7)	0.0100 (7)
C15	0.0574 (10)	0.0369 (9)	0.0507 (10)	0.0068 (7)	−0.0067 (8)	0.0035 (7)
C16	0.0414 (8)	0.0408 (9)	0.0402 (8)	0.0029 (7)	0.0008 (7)	−0.0020 (7)
C41	0.0339 (7)	0.0398 (8)	0.0328 (7)	0.0008 (6)	0.0017 (6)	−0.0008 (6)
C42	0.0386 (8)	0.0441 (9)	0.0430 (8)	−0.0059 (7)	−0.0040 (7)	0.0038 (7)
C43	0.0512 (9)	0.0375 (9)	0.0464 (9)	−0.0011 (7)	−0.0037 (7)	0.0073 (7)
C44	0.0407 (8)	0.0472 (10)	0.0343 (7)	0.0075 (7)	0.0020 (6)	0.0006 (7)
C45	0.0316 (7)	0.0491 (10)	0.0545 (10)	−0.0004 (7)	0.0036 (7)	0.0016 (8)
C46	0.0390 (8)	0.0359 (8)	0.0589 (10)	−0.0003 (7)	0.0040 (7)	0.0032 (8)
O44	0.0447 (7)	0.0560 (8)	0.0700 (8)	0.0120 (6)	−0.0018 (6)	0.0148 (6)
C441	0.0427 (10)	0.0790 (14)	0.0509 (10)	0.0160 (9)	0.0008 (7)	0.0129 (9)

Geometric parameters (Å, º) top

N1—C17	1.3440 (18)	C13—C14	1.377 (2)
N1—C2	1.4575 (18)	C13—H13	0.9300
N1—C6	1.4616 (18)	C14—C15	1.383 (2)
C2—C3	1.512 (2)	C14—H14	0.9300
C2—H2A	0.9700	C15—C16	1.379 (2)
C2—H2B	0.9700	C15—H15	0.9300
C3—N4	1.4587 (18)	C16—H16	0.9300
C3—H3A	0.9700	C41—C42	1.390 (2)
C3—H3B	0.9700	C41—C46	1.393 (2)
N4—C41	1.4222 (18)	C42—C43	1.388 (2)
N4—C5	1.4686 (19)	C42—H42	0.9300
C5—C6	1.511 (2)	C43—C44	1.378 (2)
C5—H5A	0.9700	C43—H43	0.9300
C5—H5B	0.9700	C44—O44	1.3779 (18)
C6—H6A	0.9700	C44—C45	1.382 (2)
C6—H6B	0.9700	C45—C46	1.383 (2)
C17—O17	1.2428 (16)	C45—H45	0.9300
C17—C11	1.496 (2)	C46—H46	0.9300
C11—C12	1.395 (2)	O44—C441	1.422 (2)
C11—C16	1.395 (2)	C441—H41A	0.9600
C12—O12	1.3625 (18)	C441—H41B	0.9600
C12—C13	1.390 (2)	C441—H41C	0.9600
O12—H12	0.92 (2)

C17—N1—C2	120.99 (12)	C12—O12—H12	108.7 (12)
C17—N1—C6	125.97 (12)	C14—C13—C12	120.40 (14)
C2—N1—C6	112.73 (11)	C14—C13—H13	119.8
N1—C2—C3	111.34 (12)	C12—C13—H13	119.8
N1—C2—H2A	109.4	C13—C14—C15	120.69 (15)
C3—C2—H2A	109.4	C13—C14—H14	119.7
N1—C2—H2B	109.4	C15—C14—H14	119.7
C3—C2—H2B	109.4	C16—C15—C14	119.06 (15)
H2A—C2—H2B	108.0	C16—C15—H15	120.5
N4—C3—C2	109.92 (13)	C14—C15—H15	120.5
N4—C3—H3A	109.7	C15—C16—C11	121.35 (14)
C2—C3—H3A	109.7	C15—C16—H16	119.3
N4—C3—H3B	109.7	C11—C16—H16	119.3
C2—C3—H3B	109.7	C42—C41—C46	117.07 (14)
H3A—C3—H3B	108.2	C42—C41—N4	123.40 (13)
C41—N4—C3	117.01 (12)	C46—C41—N4	119.48 (14)
C41—N4—C5	115.80 (11)	C43—C42—C41	121.33 (14)
C3—N4—C5	110.23 (11)	C43—C42—H42	119.3
N4—C5—C6	110.83 (12)	C41—C42—H42	119.3
N4—C5—H5A	109.5	C44—C43—C42	120.62 (15)
C6—C5—H5A	109.5	C44—C43—H43	119.7
N4—C5—H5B	109.5	C42—C43—H43	119.7
C6—C5—H5B	109.5	C43—C44—O44	116.19 (15)
H5A—C5—H5B	108.1	C43—C44—C45	118.95 (14)
N1—C6—C5	109.90 (13)	O44—C44—C45	124.86 (14)
N1—C6—H6A	109.7	C44—C45—C46	120.29 (15)
C5—C6—H6A	109.7	C44—C45—H45	119.9
N1—C6—H6B	109.7	C46—C45—H45	119.9
C5—C6—H6B	109.7	C45—C46—C41	121.71 (15)
H6A—C6—H6B	108.2	C45—C46—H46	119.1
O17—C17—N1	120.95 (13)	C41—C46—H46	119.1
O17—C17—C11	119.87 (12)	C44—O44—C441	117.20 (14)
N1—C17—C11	119.11 (12)	O44—C441—H41A	109.5
C12—C11—C16	118.83 (13)	O44—C441—H41B	109.5
C12—C11—C17	123.99 (13)	H41A—C441—H41B	109.5
C16—C11—C17	117.11 (12)	O44—C441—H41C	109.5
O12—C12—C13	122.33 (13)	H41A—C441—H41C	109.5
O12—C12—C11	118.02 (13)	H41B—C441—H41C	109.5
C13—C12—C11	119.64 (14)

C17—N1—C2—C3	131.68 (15)	C11—C12—C13—C14	1.4 (2)
C6—N1—C2—C3	−54.39 (18)	C12—C13—C14—C15	−2.0 (2)
N1—C2—C3—N4	55.85 (17)	C13—C14—C15—C16	0.9 (2)
C2—C3—N4—C41	166.38 (12)	C14—C15—C16—C11	0.7 (2)
C2—C3—N4—C5	−58.51 (16)	C12—C11—C16—C15	−1.3 (2)
C41—N4—C5—C6	−164.75 (13)	C17—C11—C16—C15	−178.57 (14)
C3—N4—C5—C6	59.54 (17)	C3—N4—C41—C42	3.0 (2)
C17—N1—C6—C5	−132.34 (15)	C5—N4—C41—C42	−129.62 (15)
C2—N1—C6—C5	54.10 (17)	C3—N4—C41—C46	−174.21 (14)
N4—C5—C6—N1	−56.31 (17)	C5—N4—C41—C46	53.14 (19)
C2—N1—C17—O17	−1.9 (2)	C46—C41—C42—C43	−0.8 (2)
C6—N1—C17—O17	−174.98 (14)	N4—C41—C42—C43	−178.14 (14)
C2—N1—C17—C11	175.29 (13)	C41—C42—C43—C44	−0.2 (2)
C6—N1—C17—C11	2.2 (2)	C42—C43—C44—O44	−178.28 (14)
O17—C17—C11—C12	−117.64 (16)	C42—C43—C44—C45	1.3 (2)
N1—C17—C11—C12	65.13 (19)	C43—C44—C45—C46	−1.2 (2)
O17—C17—C11—C16	59.44 (18)	O44—C44—C45—C46	178.31 (15)
N1—C17—C11—C16	−117.79 (15)	C44—C45—C46—C41	0.1 (2)
C16—C11—C12—O12	−178.98 (13)	C42—C41—C46—C45	0.9 (2)
C17—C11—C12—O12	−1.9 (2)	N4—C41—C46—C45	178.32 (14)
C16—C11—C12—C13	0.2 (2)	C43—C44—O44—C441	175.77 (14)
C17—C11—C12—C13	177.27 (13)	C45—C44—O44—C441	−3.8 (2)
O12—C12—C13—C14	−179.40 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O12—H12···O17ⁱ	0.92 (2)	1.81 (2)	2.7327 (15)	175.4 (18)

Symmetry code: (i) x+1/2, y, −z+1/2.

Hydrogen bonds and short intermolecular contacts (Å, °) in compounds (I)–(VI) top

Cg1 and Cg2 are the centroids of the C11–C16 and C41–C46 rings, respectively.

Compound	D—H···A	D—H	H···A	D···A	D—H···A
(I)	C12—H12···O17ⁱ	0.93	2.61	3.497 (4)	160
(II)	C2—H2A···O17ⁱⁱ	0.97	2.50	3.387 (4)	152
	C16—H16···O17ⁱⁱⁱ	0.93	2.43	3.340 (5)	167
(III)	C3—H3A···O17^iv	0.97	2.61	3.574 (3)	175
	C2—HA···Cg1^iv	0.97	2.84	3.648 (3)	142
	C15—H15···Cg2^v	0.93	2.72	3.610 (4)	162
(IV)	C3—H3A···O17^iv	0.97	2.56	3.524 (3)	171
	C2—HA···Cg1^iv	0.97	2.82	3.630 (3)	142
	C15—H15···Cg2^v	0.93	2.68	3.579 (4)	164
(V)	C3—H3A···O17^iv	0.97	2.60	3.542 (10)	164
	C2—HA···Cg1^iv	0.97	2.87	3.719 (11)	147
	C15—H15···Cg2^v	0.93	2.73	3.656 (12)	172
(VI)	O12—H12···O17^vi	0.92 (2)	1.81 (2)	3.7327 (15)	175.4 (18)

Symmetry codes: (i) x, 1 - y, -1/2 + z; (ii) 1 - x, 1 - y, 1 - z; (iii) 2 - x, 1 - y, 1 - z; (iv) -1/2 + x, 1/2 - y, 1 - z; (v) 3/2 - x, -1/2 + y, z; (vi) -1/2 + x, y, 1/2 - z.

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Six 1-aroyl-4-(4-meth­oxy­phen­yl)piperazines: similar mol­ecular structures but different patterns of supra­molecular assembly

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checkCIF/PLATON results

Six 1-aroyl-4-(4-methoxyphenyl)piperazines: similar molecular structures but different patterns of supramolecular assembly