Download citation
Download citation
link to html
Crystal structure analysis of N-[2-(4-fluoro-3-phen­oxy­benzo­yl)hydrazinecarbo­thio­yl]benzamide and its 4-meth­oxy derivative highlights the significance of strong and weak hydrogen bonds. The difference in the contributions of atom–atom contacts obtained from Hirshfeld surface analysis and fingerprint plots helps in distinguishing the variations in the crystal packing of the two compounds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989021001900/dj2021sup1.cif
Contains datablocks A1, A2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989021001900/dj2021A1sup2.hkl
Contains datablock A1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989021001900/dj2021A2sup3.hkl
Contains datablock A2

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989021001900/dj2021A1sup4.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989021001900/dj2021A2sup5.cml
Supplementary material

CCDC references: 2063226; 2063225

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.043
  • wR factor = 0.119
  • Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Datablock: A1


Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for F1 --C8 . 5.1 s.u. PLAT241_ALERT_2_C High 'MainMol' Ueq as Compared to Neighbors of O1 Check PLAT480_ALERT_4_C Long H...A H-Bond Reported H19 ..S1 . 2.98 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H20 ..O1 . 2.77 Ang. PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 8.421 Check
Alert level G PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 3 Report 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 53 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 5 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 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 2 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: A2
Alert level A THETM01_ALERT_3_A The value of sine(theta_max)/wavelength is less than 0.550 Calculated sin(theta_max)/wavelength = 0.5026
Author Response: The value of sine(theta_max)/wavelength is less due to weakly diffracting nature of the crystal.
PLAT023_ALERT_3_A Resolution (too) Low [sin(theta)/Lambda < 0.6]..      20.93 Ang-1
Author Response: This is on account of the weakly diffracting nature of the crystal.

Alert level B PLAT088_ALERT_3_B Poor Data / Parameter Ratio .................... 7.79 Note
Alert level C PLAT241_ALERT_2_C High 'MainMol' Ueq as Compared to Neighbors of O1 Check PLAT241_ALERT_2_C High 'MainMol' Ueq as Compared to Neighbors of C3 Check PLAT242_ALERT_2_C Low 'MainMol' Ueq as Compared to Neighbors of C1 Check PLAT242_ALERT_2_C Low 'MainMol' Ueq as Compared to Neighbors of C8 Check PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.007 Ang. PLAT414_ALERT_2_C Short Intra D-H..H-X H3N ..H17 1.98 Ang. x,y,z = 1_555 Check PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 2.492 Check PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.503 4 Report PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density. 0 Info
Alert level G PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 3 Report PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large 7.46 Why ? PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still 61% Note PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 3 Note
2 ALERT level A = Most likely a serious problem - resolve or explain 1 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 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 8 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Computing details top

For both structures, data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2020), WinGX (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).

N-[2-(4-Fluoro-3-phenoxybenzoyl)hydrazinecarbothioyl]benzamide (A1) top
Crystal data top
C21H16FN3O3SF(000) = 848
Mr = 409.43Dx = 1.401 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 18.3849 (13) ÅCell parameters from 10485 reflections
b = 7.7063 (6) Åθ = 2.2–28.6°
c = 13.9216 (10) ŵ = 0.20 mm1
β = 100.136 (5)°T = 298 K
V = 1941.6 (2) Å3Plates, colorless
Z = 40.27 × 0.20 × 0.14 mm
Data collection top
Bruker APEXII CCD
diffractometer
2753 reflections with I > 2σ(I)
φ and ω scansRint = 0.043
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
θmax = 27.7°, θmin = 2.3°
h = 2321
31160 measured reflectionsk = 1010
4460 independent reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.119 w = 1/[σ2(Fo2) + (0.0531P)2 + 0.1773P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
4460 reflectionsΔρmax = 0.15 e Å3
262 parametersΔρmin = 0.17 e Å3
0 restraints
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
xyzUiso*/Ueq
N20.35731 (8)0.0786 (2)0.88306 (10)0.0603 (4)
H2N0.3981460.1088840.8657930.072*
O20.35727 (7)0.08997 (19)0.69344 (9)0.0715 (4)
N10.30299 (8)0.0015 (2)0.81656 (10)0.0635 (4)
H10.2674950.0539980.8355840.076*
C150.47522 (9)0.2198 (2)1.01326 (12)0.0544 (4)
N30.40609 (7)0.18548 (18)1.03435 (9)0.0538 (4)
H3N0.3985700.2162291.0911720.065*
C190.63953 (10)0.4486 (3)1.22873 (13)0.0637 (5)
H190.6758150.5004991.2747310.076*
C130.30627 (10)0.0143 (2)0.72070 (12)0.0546 (4)
C110.24397 (10)0.0680 (2)0.65341 (12)0.0548 (4)
O30.48982 (7)0.18773 (19)0.93243 (8)0.0737 (4)
C120.23455 (10)0.0202 (2)0.55602 (12)0.0587 (5)
H120.2676550.0564220.5352420.070*
C180.58177 (10)0.3634 (3)1.25799 (13)0.0651 (5)
H180.5794760.3557761.3240570.078*
C160.53052 (9)0.2979 (2)1.09115 (11)0.0509 (4)
C70.17640 (11)0.0857 (3)0.48974 (13)0.0650 (5)
C170.52695 (10)0.2888 (2)1.19000 (12)0.0589 (5)
H170.4875720.2324361.2103290.071*
O10.16903 (8)0.0470 (2)0.39147 (9)0.0815 (4)
C200.64377 (11)0.4571 (3)1.13081 (13)0.0683 (5)
H200.6830890.5145031.1109430.082*
C140.34729 (9)0.1066 (2)0.97367 (11)0.0524 (4)
C10.13186 (10)0.1053 (3)0.35731 (13)0.0658 (5)
C100.19555 (10)0.1858 (3)0.68345 (14)0.0678 (5)
H100.2024400.2210530.7483150.081*
C210.59024 (10)0.3814 (3)1.06281 (12)0.0610 (5)
H210.5939400.3859980.9970840.073*
C80.12811 (11)0.1982 (3)0.52212 (15)0.0755 (6)
F10.07018 (8)0.2577 (2)0.45739 (10)0.1157 (5)
C90.13740 (12)0.2507 (3)0.61757 (16)0.0828 (6)
H90.1047040.3293620.6375260.099*
C60.09068 (11)0.2008 (3)0.41052 (15)0.0756 (6)
H60.0861510.1669590.4733270.091*
C40.06114 (16)0.3971 (4)0.2770 (2)0.1119 (9)
H40.0364670.4953050.2493630.134*
C20.13978 (13)0.1537 (3)0.26449 (15)0.0849 (7)
H20.1690360.0893530.2294770.102*
C30.10316 (18)0.3001 (4)0.2249 (2)0.1101 (9)
H30.1070280.3336050.1618700.132*
C50.05585 (13)0.3485 (4)0.3694 (2)0.0958 (7)
H50.0283650.4157920.4054260.115*
S10.26986 (3)0.05350 (8)1.01272 (3)0.07183 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.0605 (9)0.0788 (10)0.0420 (8)0.0123 (8)0.0097 (7)0.0069 (7)
O20.0662 (8)0.0981 (10)0.0499 (7)0.0220 (7)0.0097 (6)0.0030 (7)
N10.0659 (10)0.0808 (11)0.0435 (8)0.0197 (8)0.0090 (7)0.0051 (8)
C150.0558 (10)0.0637 (11)0.0457 (9)0.0021 (8)0.0147 (8)0.0033 (8)
N30.0539 (8)0.0702 (10)0.0381 (7)0.0016 (7)0.0100 (6)0.0055 (7)
C190.0562 (11)0.0809 (13)0.0525 (10)0.0022 (10)0.0053 (8)0.0055 (10)
C130.0590 (11)0.0618 (11)0.0425 (9)0.0026 (9)0.0076 (8)0.0010 (8)
C110.0566 (10)0.0612 (11)0.0457 (9)0.0014 (9)0.0070 (8)0.0016 (8)
O30.0684 (8)0.1078 (11)0.0495 (7)0.0126 (7)0.0229 (6)0.0201 (7)
C120.0637 (11)0.0683 (12)0.0444 (9)0.0035 (9)0.0107 (8)0.0032 (8)
C180.0610 (11)0.0937 (14)0.0408 (9)0.0028 (10)0.0095 (8)0.0040 (9)
C160.0512 (10)0.0590 (10)0.0433 (8)0.0056 (8)0.0104 (7)0.0012 (8)
C70.0693 (12)0.0775 (13)0.0450 (10)0.0071 (10)0.0012 (9)0.0073 (9)
C170.0540 (10)0.0781 (12)0.0467 (9)0.0011 (9)0.0149 (8)0.0006 (9)
O10.0998 (11)0.0991 (11)0.0421 (7)0.0170 (9)0.0026 (7)0.0105 (7)
C200.0595 (11)0.0891 (14)0.0576 (11)0.0121 (10)0.0136 (9)0.0041 (10)
C140.0585 (11)0.0573 (10)0.0409 (8)0.0019 (8)0.0076 (8)0.0015 (8)
C10.0568 (11)0.0850 (14)0.0496 (10)0.0092 (10)0.0068 (9)0.0020 (10)
C100.0663 (12)0.0775 (13)0.0573 (11)0.0110 (10)0.0048 (9)0.0084 (10)
C210.0609 (11)0.0792 (13)0.0443 (9)0.0033 (10)0.0134 (8)0.0014 (9)
C80.0648 (13)0.0863 (15)0.0666 (13)0.0101 (11)0.0126 (10)0.0100 (11)
F10.0972 (10)0.1390 (12)0.0957 (9)0.0334 (9)0.0246 (8)0.0135 (9)
C90.0714 (13)0.0906 (15)0.0824 (15)0.0234 (12)0.0023 (11)0.0080 (13)
C60.0658 (13)0.0965 (17)0.0625 (12)0.0016 (11)0.0058 (10)0.0011 (12)
C40.101 (2)0.112 (2)0.116 (2)0.0046 (17)0.0013 (18)0.034 (2)
C20.0881 (16)0.1073 (18)0.0569 (12)0.0178 (14)0.0063 (11)0.0009 (13)
C30.128 (2)0.122 (2)0.0745 (16)0.0238 (19)0.0032 (16)0.0288 (17)
C50.0718 (15)0.1026 (19)0.111 (2)0.0045 (14)0.0110 (14)0.0038 (16)
S10.0630 (3)0.1025 (4)0.0515 (3)0.0143 (3)0.0141 (2)0.0031 (3)
Geometric parameters (Å, º) top
N2—C141.3242 (19)C7—O11.383 (2)
N2—N11.3718 (19)C17—H170.9300
N2—H2N0.8600O1—C11.399 (2)
O2—C131.220 (2)C20—C211.370 (3)
N1—C131.350 (2)C20—H200.9300
N1—H10.8600C14—S11.6617 (17)
C15—O31.2272 (18)C1—C61.364 (3)
C15—N31.379 (2)C1—C21.377 (3)
C15—C161.478 (2)C10—C91.374 (3)
N3—C141.389 (2)C10—H100.9300
N3—H3N0.8600C21—H210.9300
C19—C181.370 (3)C8—F11.349 (2)
C19—C201.381 (2)C8—C91.371 (3)
C19—H190.9300C9—H90.9300
C13—C111.488 (2)C6—C51.380 (3)
C11—C121.386 (2)C6—H60.9300
C11—C101.387 (2)C4—C51.360 (4)
C12—C71.379 (3)C4—C31.370 (4)
C12—H120.9300C4—H40.9300
C18—C171.381 (2)C2—C31.378 (4)
C18—H180.9300C2—H20.9300
C16—C211.389 (2)C3—H30.9300
C16—C171.391 (2)C5—H50.9300
C7—C81.372 (3)
C14—N2—N1120.44 (14)C21—C20—C19120.23 (17)
C14—N2—H2N119.8C21—C20—H20119.9
N1—N2—H2N119.8C19—C20—H20119.9
C13—N1—N2118.79 (14)N2—C14—N3115.25 (14)
C13—N1—H1120.6N2—C14—S1122.85 (13)
N2—N1—H1120.6N3—C14—S1121.90 (12)
O3—C15—N3120.99 (16)C6—C1—C2121.6 (2)
O3—C15—C16121.44 (15)C6—C1—O1123.55 (18)
N3—C15—C16117.57 (13)C2—C1—O1114.8 (2)
C15—N3—C14127.02 (13)C9—C10—C11120.14 (18)
C15—N3—H3N116.5C9—C10—H10119.9
C14—N3—H3N116.5C11—C10—H10119.9
C18—C19—C20119.86 (17)C20—C21—C16120.58 (16)
C18—C19—H19120.1C20—C21—H21119.7
C20—C19—H19120.1C16—C21—H21119.7
O2—C13—N1120.86 (16)F1—C8—C9119.7 (2)
O2—C13—C11123.81 (15)F1—C8—C7118.42 (19)
N1—C13—C11115.33 (15)C9—C8—C7121.84 (18)
C12—C11—C10119.51 (17)C8—C9—C10119.28 (19)
C12—C11—C13116.91 (16)C8—C9—H9120.4
C10—C11—C13123.57 (16)C10—C9—H9120.4
C7—C12—C11120.40 (18)C1—C6—C5118.7 (2)
C7—C12—H12119.8C1—C6—H6120.6
C11—C12—H12119.8C5—C6—H6120.6
C19—C18—C17120.41 (16)C5—C4—C3119.4 (3)
C19—C18—H18119.8C5—C4—H4120.3
C17—C18—H18119.8C3—C4—H4120.3
C21—C16—C17118.81 (16)C1—C2—C3118.1 (2)
C21—C16—C15117.16 (14)C1—C2—H2120.9
C17—C16—C15124.01 (15)C3—C2—H2120.9
C8—C7—C12118.78 (17)C4—C3—C2121.1 (2)
C8—C7—O1120.31 (18)C4—C3—H3119.4
C12—C7—O1120.81 (18)C2—C3—H3119.4
C18—C17—C16120.09 (16)C4—C5—C6121.0 (3)
C18—C17—H17120.0C4—C5—H5119.5
C16—C17—H17120.0C6—C5—H5119.5
C7—O1—C1118.30 (15)
C14—N2—N1—C13163.27 (16)N1—N2—C14—S10.5 (2)
O3—C15—N3—C143.4 (3)C15—N3—C14—N27.4 (2)
C16—C15—N3—C14177.17 (15)C15—N3—C14—S1173.17 (14)
N2—N1—C13—O21.4 (3)C7—O1—C1—C612.8 (3)
N2—N1—C13—C11178.11 (15)C7—O1—C1—C2167.18 (18)
O2—C13—C11—C1215.9 (3)C12—C11—C10—C91.9 (3)
N1—C13—C11—C12163.59 (16)C13—C11—C10—C9177.23 (19)
O2—C13—C11—C10164.89 (19)C19—C20—C21—C161.1 (3)
N1—C13—C11—C1015.6 (3)C17—C16—C21—C201.5 (3)
C10—C11—C12—C71.7 (3)C15—C16—C21—C20179.92 (17)
C13—C11—C12—C7177.53 (17)C12—C7—C8—F1178.13 (18)
C20—C19—C18—C171.2 (3)O1—C7—C8—F15.5 (3)
O3—C15—C16—C2119.2 (3)C12—C7—C8—C91.9 (3)
N3—C15—C16—C21160.26 (15)O1—C7—C8—C9174.4 (2)
O3—C15—C16—C17159.26 (18)F1—C8—C9—C10178.4 (2)
N3—C15—C16—C1721.3 (3)C7—C8—C9—C101.7 (4)
C11—C12—C7—C80.2 (3)C11—C10—C9—C80.3 (3)
C11—C12—C7—O1176.13 (16)C2—C1—C6—C50.5 (3)
C19—C18—C17—C160.8 (3)O1—C1—C6—C5179.55 (18)
C21—C16—C17—C180.6 (3)C6—C1—C2—C31.7 (3)
C15—C16—C17—C18179.02 (17)O1—C1—C2—C3178.36 (19)
C8—C7—O1—C197.3 (2)C5—C4—C3—C20.4 (4)
C12—C7—O1—C186.4 (2)C1—C2—C3—C41.3 (4)
C18—C19—C20—C210.3 (3)C3—C4—C5—C61.6 (4)
N1—N2—C14—N3179.95 (15)C1—C6—C5—C41.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O30.861.882.555 (2)135
C18—H18···O3i0.932.453.218 (2)141
N3—H3N···O2i0.862.283.067 (2)152
C19—H19···S1ii0.932.983.778 (2)145
C20—H20···O1iii0.932.773.510 (3)138
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y+1/2, z+5/2; (iii) x+1, y+1/2, z+3/2.
N-[2-(4-Fluoro-3-phenoxybenzoyl)hydrazinecarbothioyl]-4-methoxybenzamide (A2) top
Crystal data top
C22H18FN3O4SF(000) = 1824
Mr = 439.45Dx = 1.412 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 47.298 (3) ÅCell parameters from 9864 reflections
b = 4.8054 (3) Åθ = 2.3–21.0°
c = 18.4939 (10) ŵ = 0.20 mm1
β = 100.429 (6)°T = 298 K
V = 4134.0 (4) Å3Plates, colorless
Z = 80.25 × 0.17 × 0.10 mm
Data collection top
Bruker APEXII CCD
diffractometer
1751 reflections with I > 2σ(I)
φ and ω scansRint = 0.062
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
θmax = 20.9°, θmin = 2.3°
h = 4638
9841 measured reflectionsk = 44
2188 independent reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.122 w = 1/[σ2(Fo2) + (0.0421P)2 + 7.4575P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
2188 reflectionsΔρmax = 0.20 e Å3
281 parametersΔρmin = 0.16 e Å3
0 restraints
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
xyzUiso*/Ueq
S10.46155 (2)0.5067 (2)0.20257 (5)0.0570 (4)
O30.48485 (5)0.1767 (5)0.05581 (13)0.0564 (7)
O20.40193 (5)0.2064 (6)0.06269 (16)0.0693 (8)
N30.49466 (6)0.1596 (6)0.14319 (15)0.0476 (8)
H3N0.5084580.2440090.1714250.057*
O40.61871 (6)0.3864 (7)0.15455 (17)0.0846 (9)
N20.44651 (6)0.1428 (6)0.09635 (17)0.0548 (8)
H2N0.4505100.0223830.0653140.066*
F10.28801 (5)0.3872 (7)0.11032 (16)0.1091 (10)
C160.53329 (7)0.1387 (7)0.11626 (18)0.0431 (9)
N10.41856 (7)0.2174 (7)0.09631 (18)0.0636 (9)
H10.4145880.3868400.1055550.076*
C130.39757 (8)0.0319 (9)0.0822 (2)0.0514 (10)
C110.36866 (8)0.1329 (8)0.0915 (2)0.0516 (10)
C140.46729 (8)0.2578 (7)0.14456 (18)0.0438 (9)
O10.29250 (6)0.0013 (8)0.01236 (19)0.1023 (12)
C210.54221 (8)0.3385 (8)0.0720 (2)0.0547 (10)
H210.5288670.4167110.0343490.066*
C150.50265 (8)0.0588 (7)0.10183 (19)0.0441 (9)
C190.59029 (8)0.3153 (9)0.1383 (2)0.0576 (10)
C200.57034 (9)0.4253 (8)0.0820 (2)0.0603 (11)
H200.5758940.5581200.0507370.072*
C170.55367 (9)0.0281 (8)0.1725 (2)0.0601 (11)
H170.5482500.1075880.2031900.072*
C120.34481 (8)0.0178 (9)0.0473 (2)0.0638 (11)
H120.3471920.1198510.0135480.077*
C180.58180 (9)0.1171 (10)0.1835 (2)0.0678 (12)
H180.5951470.0425430.2216740.081*
C100.36521 (9)0.3291 (9)0.1432 (2)0.0663 (11)
H100.3811750.4057030.1734170.080*
C70.31751 (9)0.1059 (10)0.0528 (2)0.0710 (12)
C80.31463 (9)0.3024 (10)0.1041 (3)0.0714 (12)
C90.33763 (11)0.4125 (10)0.1500 (3)0.0804 (14)
H90.3349550.5420170.1855000.096*
C10.29108 (10)0.0900 (12)0.0591 (3)0.0824 (15)
C220.62909 (10)0.5808 (11)0.1078 (3)0.0994 (17)
H22A0.6196230.7563180.1103270.149*
H22B0.6494390.6042670.1233940.149*
H22C0.6252280.5132640.0581660.149*
C20.27240 (11)0.3041 (13)0.0798 (3)0.1014 (17)
H20.2629320.3863890.0453530.122*
C50.30114 (16)0.0664 (17)0.1801 (4)0.120 (2)
H50.3107760.0124040.2146590.144*
C40.28168 (18)0.2822 (19)0.1998 (4)0.128 (3)
H40.2782820.3485770.2478240.153*
C60.30602 (11)0.0306 (13)0.1075 (3)0.1001 (17)
H60.3190710.1731450.0925980.120*
C30.26762 (14)0.3964 (17)0.1492 (5)0.131 (2)
H30.2545530.5398960.1628680.157*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0682 (7)0.0481 (6)0.0553 (6)0.0142 (5)0.0124 (5)0.0014 (5)
O30.0554 (16)0.0545 (17)0.0589 (16)0.0012 (14)0.0092 (13)0.0131 (14)
O20.0576 (17)0.0393 (18)0.109 (2)0.0029 (14)0.0092 (15)0.0124 (16)
N30.0473 (19)0.0409 (18)0.0556 (18)0.0008 (16)0.0119 (14)0.0034 (16)
O40.0587 (19)0.094 (2)0.098 (2)0.0215 (18)0.0072 (16)0.0099 (19)
N20.047 (2)0.0453 (19)0.074 (2)0.0059 (17)0.0161 (17)0.0125 (17)
F10.0701 (18)0.141 (3)0.127 (2)0.0232 (18)0.0454 (15)0.0117 (19)
C160.051 (2)0.036 (2)0.045 (2)0.0000 (19)0.0154 (19)0.0032 (18)
N10.050 (2)0.036 (2)0.107 (3)0.0023 (18)0.0183 (18)0.0086 (18)
C130.052 (3)0.039 (3)0.062 (2)0.003 (2)0.0088 (19)0.003 (2)
C110.047 (2)0.044 (2)0.065 (2)0.001 (2)0.013 (2)0.002 (2)
C140.050 (2)0.036 (2)0.047 (2)0.000 (2)0.0138 (19)0.0088 (18)
O10.0447 (18)0.159 (3)0.104 (3)0.010 (2)0.0170 (17)0.039 (2)
C210.055 (3)0.053 (3)0.058 (2)0.001 (2)0.0142 (19)0.006 (2)
C150.052 (2)0.039 (2)0.045 (2)0.000 (2)0.018 (2)0.0040 (19)
C190.053 (3)0.057 (3)0.063 (3)0.008 (2)0.010 (2)0.005 (2)
C200.065 (3)0.052 (3)0.068 (3)0.007 (2)0.022 (2)0.011 (2)
C170.063 (3)0.060 (3)0.059 (2)0.005 (2)0.015 (2)0.011 (2)
C120.051 (3)0.064 (3)0.079 (3)0.003 (2)0.020 (2)0.014 (2)
C180.056 (3)0.080 (3)0.064 (3)0.008 (2)0.002 (2)0.013 (2)
C100.060 (3)0.066 (3)0.075 (3)0.004 (2)0.017 (2)0.010 (3)
C70.059 (3)0.082 (3)0.074 (3)0.001 (3)0.017 (2)0.003 (3)
C80.053 (3)0.084 (3)0.084 (3)0.012 (3)0.031 (3)0.001 (3)
C90.089 (4)0.073 (3)0.088 (3)0.003 (3)0.039 (3)0.017 (3)
C10.050 (3)0.104 (4)0.088 (4)0.017 (3)0.000 (3)0.024 (3)
C220.077 (3)0.097 (4)0.129 (4)0.028 (3)0.031 (3)0.010 (4)
C20.073 (3)0.121 (5)0.106 (4)0.014 (4)0.005 (3)0.023 (4)
C50.118 (5)0.142 (6)0.099 (5)0.046 (5)0.015 (4)0.027 (5)
C40.128 (6)0.151 (7)0.091 (5)0.056 (5)0.015 (5)0.018 (5)
C60.082 (4)0.117 (5)0.101 (4)0.013 (3)0.015 (3)0.001 (4)
C30.100 (5)0.158 (7)0.125 (6)0.022 (5)0.006 (5)0.039 (6)
Geometric parameters (Å, º) top
S1—C141.661 (4)C20—H200.9300
O3—C151.223 (4)C17—C181.377 (5)
O2—C131.229 (4)C17—H170.9300
N3—C141.383 (4)C12—C71.380 (5)
N3—C151.391 (4)C12—H120.9300
N3—H3N0.8600C18—H180.9300
O4—C191.367 (4)C10—C91.392 (6)
O4—C221.419 (5)C10—H100.9300
N2—C141.322 (4)C7—C81.362 (6)
N2—N11.369 (4)C8—C91.360 (6)
N2—H2N0.8600C9—H90.9300
F1—C81.348 (4)C1—C21.365 (7)
C16—C211.377 (5)C1—C61.365 (7)
C16—C171.390 (5)C22—H22A0.9600
C16—C151.476 (5)C22—H22B0.9600
N1—C131.325 (5)C22—H22C0.9600
N1—H10.8600C2—C31.338 (8)
C13—C111.490 (5)C2—H20.9300
C11—C101.373 (5)C5—C41.390 (9)
C11—C121.383 (5)C5—C61.401 (8)
O1—C71.375 (5)C5—H50.9300
O1—C11.383 (5)C4—C31.359 (9)
C21—C201.374 (5)C4—H40.9300
C21—H210.9300C6—H60.9300
C19—C181.374 (5)C3—H30.9300
C19—C201.378 (5)
C14—N3—C15128.0 (3)C11—C12—H12119.8
C14—N3—H3N116.0C19—C18—C17120.5 (4)
C15—N3—H3N116.0C19—C18—H18119.8
C19—O4—C22117.7 (3)C17—C18—H18119.8
C14—N2—N1119.4 (3)C11—C10—C9119.4 (4)
C14—N2—H2N120.3C11—C10—H10120.3
N1—N2—H2N120.3C9—C10—H10120.3
C21—C16—C17117.8 (3)C8—C7—O1116.6 (4)
C21—C16—C15118.1 (3)C8—C7—C12118.5 (4)
C17—C16—C15124.1 (3)O1—C7—C12124.9 (4)
C13—N1—N2120.9 (3)F1—C8—C9118.9 (4)
C13—N1—H1119.6F1—C8—C7118.8 (4)
N2—N1—H1119.6C9—C8—C7122.3 (4)
O2—C13—N1121.7 (3)C8—C9—C10119.3 (4)
O2—C13—C11122.9 (4)C8—C9—H9120.4
N1—C13—C11115.4 (4)C10—C9—H9120.4
C10—C11—C12120.0 (4)C2—C1—C6121.5 (5)
C10—C11—C13122.1 (4)C2—C1—O1115.1 (5)
C12—C11—C13117.9 (4)C6—C1—O1123.4 (5)
N2—C14—N3115.4 (3)O4—C22—H22A109.5
N2—C14—S1123.2 (3)O4—C22—H22B109.5
N3—C14—S1121.4 (3)H22A—C22—H22B109.5
C7—O1—C1121.6 (4)O4—C22—H22C109.5
C20—C21—C16121.7 (4)H22A—C22—H22C109.5
C20—C21—H21119.2H22B—C22—H22C109.5
C16—C21—H21119.2C3—C2—C1120.4 (7)
O3—C15—N3120.7 (3)C3—C2—H2119.8
O3—C15—C16122.3 (3)C1—C2—H2119.8
N3—C15—C16116.9 (3)C4—C5—C6119.0 (7)
O4—C19—C18115.0 (4)C4—C5—H5120.5
O4—C19—C20125.6 (4)C6—C5—H5120.5
C18—C19—C20119.3 (4)C3—C4—C5120.3 (7)
C21—C20—C19119.9 (4)C3—C4—H4119.9
C21—C20—H20120.0C5—C4—H4119.9
C19—C20—H20120.0C1—C6—C5118.2 (6)
C18—C17—C16120.8 (4)C1—C6—H6120.9
C18—C17—H17119.6C5—C6—H6120.9
C16—C17—H17119.6C2—C3—C4120.6 (7)
C7—C12—C11120.5 (4)C2—C3—H3119.7
C7—C12—H12119.8C4—C3—H3119.7
C14—N2—N1—C13143.5 (4)C13—C11—C12—C7179.2 (4)
N2—N1—C13—O26.2 (6)O4—C19—C18—C17180.0 (4)
N2—N1—C13—C11173.9 (3)C20—C19—C18—C170.2 (6)
O2—C13—C11—C10147.9 (4)C16—C17—C18—C190.7 (6)
N1—C13—C11—C1032.2 (5)C12—C11—C10—C90.6 (6)
O2—C13—C11—C1230.6 (5)C13—C11—C10—C9179.1 (4)
N1—C13—C11—C12149.3 (4)C1—O1—C7—C8149.6 (5)
N1—N2—C14—N3176.7 (3)C1—O1—C7—C1233.4 (7)
N1—N2—C14—S14.1 (5)C11—C12—C7—C81.8 (6)
C15—N3—C14—N25.7 (5)C11—C12—C7—O1178.8 (4)
C15—N3—C14—S1175.2 (3)O1—C7—C8—F12.0 (6)
C17—C16—C21—C200.7 (5)C12—C7—C8—F1179.3 (4)
C15—C16—C21—C20179.7 (3)O1—C7—C8—C9176.8 (4)
C14—N3—C15—O35.9 (5)C12—C7—C8—C90.4 (7)
C14—N3—C15—C16174.1 (3)F1—C8—C9—C10179.1 (4)
C21—C16—C15—O35.2 (5)C7—C8—C9—C102.1 (7)
C17—C16—C15—O3173.8 (3)C11—C10—C9—C81.5 (7)
C21—C16—C15—N3174.7 (3)C7—O1—C1—C2148.1 (4)
C17—C16—C15—N36.3 (5)C7—O1—C1—C634.9 (7)
C22—O4—C19—C18177.2 (4)C6—C1—C2—C32.0 (8)
C22—O4—C19—C203.0 (6)O1—C1—C2—C3175.1 (5)
C16—C21—C20—C191.2 (6)C6—C5—C4—C30.1 (9)
O4—C19—C20—C21179.1 (4)C2—C1—C6—C51.7 (8)
C18—C19—C20—C210.7 (6)O1—C1—C6—C5175.1 (4)
C21—C16—C17—C180.2 (6)C4—C5—C6—C10.7 (8)
C15—C16—C17—C18178.8 (3)C1—C2—C3—C41.3 (9)
C10—C11—C12—C72.3 (6)C5—C4—C3—C20.4 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O30.861.922.589 (4)134
N3—H3N···S1i0.862.803.615 (3)159
C17—H17···S1i0.932.693.614 (4)174
N1—H1···O2ii0.862.152.915 (4)148
C21—H21···O3iii0.932.573.399 (4)148
Symmetry codes: (i) x+1, y, z+1/2; (ii) x, y+1, z; (iii) x+1, y1, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds