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In the crystal structures of the monohydrate and methanol solvate title compounds, the host mol­ecule adopts similar geometries with an alternating orientation of the substituents above and below the plane of the central arene ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989020012554/is5557sup1.cif
Contains datablocks 1a, 1b, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989020012554/is55571asup2.hkl
Contains datablock 1a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989020012554/is55571bsup3.hkl
Contains datablock 1b

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989020012554/is55571asup4.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989020012554/is55571bsup5.cml
Supplementary material

CCDC references: 2032104; 2032103

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.043
  • wR factor = 0.114
  • Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Datablock: 1a


Alert level C PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 35 Report
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 11 Note PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 6 Report PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 6 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 47 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ... 4 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 18 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 7 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 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Datablock: 1b
Alert level A PLAT601_ALERT_2_A Unit Cell Contains Solvent Accessible VOIDS of . 269 Ang   3
Author Response: The crystal structure <b>1b</b> contains highly disordered solvent molecules which could not be refined to an acceptable level. Thus, the SQUEEZE routine (Spek, 2015) of the PLATON program was used to generate a modified data set in which the contribution of the disordered molecules to the structure amplitudes is eliminated. These solvent molecules are not considered in the given chemical formula.

Alert level B PLAT919_ALERT_3_B Reflection # Likely Affected by the Beamstop ... 1 Check
Alert level C DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT097_ALERT_2_C Large Reported Max. (Positive) Residual Density 0.64 eA-3 PLAT213_ALERT_2_C Atom C17 has ADP max/min Ratio ..... 3.3 prolat PLAT213_ALERT_2_C Atom C19 has ADP max/min Ratio ..... 3.2 prolat PLAT220_ALERT_2_C NonSolvent Resd 1 C Ueq(max)/Ueq(min) Range 4.8 Ratio PLAT222_ALERT_3_C NonSolvent Resd 1 H Uiso(max)/Uiso(min) Range 5.1 Ratio PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00448 Ang. PLAT420_ALERT_2_C D-H Without Acceptor N3 --H3 . Please Check PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 20 Report PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) . 3 Check PLAT922_ALERT_1_C wR2 in the CIF and FCF Differ by ............... -0.0016 Check PLAT923_ALERT_1_C S Values in the CIF and FCF Differ by ....... -0.012 Check PLAT927_ALERT_1_C Reported and Calculated wR2 Differ by ......... -0.0017 Check PLAT934_ALERT_3_C Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers .. 1 Check PLAT977_ALERT_2_C Check Negative Difference Density on H27A -0.34 eA-3
Alert level G PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 2 Report PLAT012_ALERT_1_G N.O.K. _shelx_res_checksum Found in CIF ...... Please Check PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note) 0.002 Degree PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 2 Report PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 4 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 6 Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ... 6 Note PLAT961_ALERT_5_G Dataset Contains no Negative Intensities ....... Please Check PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 1 Info
1 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 15 ALERT level C = Check. Ensure it is not caused by an omission or oversight 10 ALERT level G = General information/check it is not something unexpected 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 9 ALERT type 2 Indicator that the structure model may be wrong or deficient 7 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check

Computing details top

For both structures, data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

{1-[(3,5-Bis{[(4,6-dimethylpyridin-2-yl)amino]methyl}-2,4,6-triethylbenzyl)amino]cyclopentyl}methanol monohydrate (1a) top
Crystal data top
C35H51N5O·H2OF(000) = 1256
Mr = 575.82Dx = 1.151 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.2239 (7) ÅCell parameters from 9674 reflections
b = 15.3576 (8) Åθ = 2.2–28.2°
c = 17.1061 (8) ŵ = 0.07 mm1
β = 107.0289 (17)°T = 100 K
V = 3321.7 (3) Å3Irregular, colourless
Z = 40.45 × 0.32 × 0.10 mm
Data collection top
Bruker X8 APEXII CCD
diffractometer
Rint = 0.034
phi and ω scansθmax = 27.4°, θmin = 2.1°
28794 measured reflectionsh = 1717
7467 independent reflectionsk = 1917
5791 reflections with I > 2σ(I)l = 2221
Refinement top
Refinement on F26 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.114 w = 1/[σ2(Fo2) + (0.0551P)2 + 0.8757P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
7467 reflectionsΔρmax = 0.27 e Å3
410 parametersΔρmin = 0.20 e Å3
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
O10.21807 (7)0.54810 (6)0.00959 (6)0.0238 (2)
N10.11044 (9)0.24557 (8)0.12255 (7)0.0218 (2)
H10.0834 (13)0.2969 (7)0.1039 (10)0.036 (5)*
N20.23912 (9)0.33295 (7)0.20586 (6)0.0198 (2)
N30.33881 (9)0.29584 (8)0.05481 (7)0.0223 (3)
H30.3046 (12)0.3464 (7)0.0466 (10)0.036 (5)*
N40.44662 (8)0.20100 (7)0.00817 (7)0.0201 (2)
N50.03784 (8)0.45806 (7)0.12196 (6)0.0176 (2)
H50.0752 (11)0.4402 (10)0.0720 (6)0.024 (4)*
C10.03521 (10)0.26699 (8)0.06516 (7)0.0163 (3)
C20.00019 (10)0.21235 (8)0.01228 (7)0.0161 (3)
C30.10826 (10)0.20103 (8)0.02240 (7)0.0167 (3)
C40.18206 (10)0.24315 (8)0.08766 (7)0.0169 (3)
C50.14833 (10)0.30214 (8)0.13754 (7)0.0172 (3)
C60.03906 (10)0.31377 (8)0.12622 (7)0.0166 (3)
C70.15304 (10)0.27362 (9)0.05636 (8)0.0197 (3)
H7A0.19360.26930.00220.024*
H7B0.16820.33110.07660.024*
C80.18900 (11)0.20182 (10)0.10409 (9)0.0264 (3)
H8A0.17530.14480.08350.040*
H8B0.26490.20800.09710.040*
H8C0.14990.20660.16220.040*
C90.14599 (11)0.14569 (9)0.03707 (8)0.0223 (3)
H9A0.21490.16840.03990.027*
H9B0.09490.15120.09220.027*
C100.15839 (13)0.04917 (10)0.01346 (10)0.0335 (4)
H10A0.20870.04310.04120.050*
H10B0.18470.01730.05320.050*
H10C0.08970.02540.01330.050*
C110.22863 (10)0.35482 (9)0.20189 (8)0.0215 (3)
H11A0.19920.41350.20520.026*
H11B0.29320.36200.18450.026*
C120.25915 (12)0.31327 (10)0.28712 (8)0.0288 (3)
H12A0.19500.30080.30280.043*
H12B0.30420.35350.32680.043*
H12C0.29770.25900.28630.043*
C130.08201 (10)0.17532 (9)0.06179 (8)0.0190 (3)
H13A0.05240.12510.08400.023*
H13B0.14510.15560.04680.023*
C140.21009 (10)0.25244 (9)0.17714 (7)0.0181 (3)
C150.27565 (10)0.17971 (9)0.20134 (8)0.0206 (3)
H150.25280.12380.17960.025*
C160.37413 (11)0.19050 (9)0.25737 (9)0.0246 (3)
C170.40303 (11)0.27384 (9)0.28877 (8)0.0237 (3)
H170.46960.28320.32820.028*
C180.33386 (10)0.34256 (9)0.26202 (8)0.0205 (3)
C190.44869 (13)0.11508 (11)0.28255 (12)0.0432 (4)
H19A0.40830.06070.27500.065*
H19B0.48930.12130.34020.065*
H19C0.49720.11400.24890.065*
C200.36075 (12)0.43342 (10)0.29491 (9)0.0282 (3)
H20A0.35850.47320.24970.042*
H20B0.43190.43380.33380.042*
H20C0.30940.45230.32270.042*
C210.29964 (10)0.22967 (9)0.09957 (8)0.0201 (3)
H21A0.33870.23320.15850.024*
H21B0.31150.17110.07970.024*
C220.40895 (10)0.28164 (9)0.01095 (8)0.0191 (3)
C230.44048 (11)0.35362 (9)0.02740 (8)0.0227 (3)
H230.41120.40960.02450.027*
C240.51400 (11)0.34216 (9)0.06903 (9)0.0249 (3)
C250.55286 (11)0.25789 (9)0.07272 (9)0.0241 (3)
H250.60340.24740.10130.029*
C260.51739 (10)0.19036 (9)0.03474 (8)0.0217 (3)
C270.55221 (14)0.41751 (11)0.10917 (11)0.0386 (4)
H27A0.52400.41220.16870.058*
H27B0.62970.41710.09350.058*
H27C0.52780.47230.09140.058*
C280.55646 (13)0.09887 (10)0.03838 (10)0.0306 (3)
H28A0.59310.07870.01700.046*
H28B0.60540.09780.07170.046*
H28C0.49630.06050.06290.046*
C290.00203 (10)0.38089 (8)0.17448 (8)0.0190 (3)
H29A0.06160.35630.19140.023*
H29B0.05470.39760.22430.023*
C300.10008 (10)0.52576 (8)0.14971 (8)0.0192 (3)
C310.02821 (11)0.57698 (9)0.22365 (8)0.0239 (3)
H31A0.04430.55260.24000.029*
H31B0.02450.63910.20940.029*
C320.07871 (14)0.56730 (11)0.29311 (9)0.0360 (4)
H32A0.04880.51670.32810.043*
H32B0.06770.62040.32740.043*
C330.19561 (13)0.55366 (10)0.24928 (10)0.0341 (4)
H33A0.23080.60940.22840.041*
H33B0.23230.52650.28590.041*
C340.19394 (11)0.49275 (9)0.17924 (8)0.0230 (3)
H34A0.26130.49620.13460.028*
H34B0.18230.43170.19850.028*
C350.14183 (11)0.58756 (9)0.07718 (8)0.0218 (3)
H35A0.17430.63880.09540.026*
H35B0.08160.60840.05890.026*
O1W0.12410 (8)0.54814 (6)0.08143 (6)0.0228 (2)
H1A0.1888 (14)0.5189 (11)0.0219 (10)0.053 (6)*
H1W0.1623 (13)0.5760 (11)0.1234 (8)0.049 (6)*
H2W0.0765 (13)0.5196 (12)0.0970 (12)0.056 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0248 (5)0.0247 (5)0.0211 (5)0.0028 (4)0.0057 (4)0.0022 (4)
N10.0216 (6)0.0227 (6)0.0174 (5)0.0049 (5)0.0001 (5)0.0022 (5)
N20.0228 (6)0.0218 (6)0.0145 (5)0.0014 (4)0.0050 (4)0.0001 (5)
N30.0219 (6)0.0215 (6)0.0262 (6)0.0011 (5)0.0114 (5)0.0022 (5)
N40.0202 (5)0.0211 (6)0.0181 (5)0.0012 (4)0.0044 (4)0.0001 (5)
N50.0225 (5)0.0153 (5)0.0154 (5)0.0005 (4)0.0063 (4)0.0017 (4)
C10.0194 (6)0.0137 (6)0.0158 (6)0.0003 (5)0.0052 (5)0.0049 (5)
C20.0203 (6)0.0123 (6)0.0143 (6)0.0016 (5)0.0031 (5)0.0026 (5)
C30.0225 (6)0.0141 (6)0.0145 (6)0.0010 (5)0.0069 (5)0.0029 (5)
C40.0181 (6)0.0172 (6)0.0150 (6)0.0002 (5)0.0045 (5)0.0045 (5)
C50.0207 (6)0.0165 (6)0.0135 (6)0.0013 (5)0.0036 (5)0.0025 (5)
C60.0213 (6)0.0145 (6)0.0145 (6)0.0000 (5)0.0060 (5)0.0016 (5)
C70.0196 (6)0.0179 (6)0.0214 (7)0.0000 (5)0.0058 (5)0.0004 (5)
C80.0254 (7)0.0261 (8)0.0303 (8)0.0017 (6)0.0121 (6)0.0027 (6)
C90.0238 (7)0.0241 (7)0.0199 (7)0.0007 (5)0.0079 (5)0.0034 (6)
C100.0371 (8)0.0227 (8)0.0425 (9)0.0041 (6)0.0144 (7)0.0069 (7)
C110.0207 (6)0.0236 (7)0.0189 (6)0.0018 (5)0.0037 (5)0.0033 (6)
C120.0301 (7)0.0345 (8)0.0177 (7)0.0014 (6)0.0004 (6)0.0021 (6)
C130.0215 (6)0.0177 (6)0.0160 (6)0.0013 (5)0.0029 (5)0.0004 (5)
C140.0196 (6)0.0229 (7)0.0126 (6)0.0000 (5)0.0059 (5)0.0015 (5)
C150.0232 (7)0.0178 (7)0.0198 (6)0.0012 (5)0.0045 (5)0.0040 (5)
C160.0238 (7)0.0239 (7)0.0235 (7)0.0014 (6)0.0028 (6)0.0058 (6)
C170.0199 (6)0.0283 (8)0.0197 (7)0.0018 (5)0.0009 (5)0.0020 (6)
C180.0229 (6)0.0239 (7)0.0153 (6)0.0018 (5)0.0068 (5)0.0001 (5)
C190.0332 (8)0.0283 (9)0.0527 (10)0.0068 (7)0.0115 (8)0.0018 (8)
C200.0313 (8)0.0271 (8)0.0244 (7)0.0014 (6)0.0052 (6)0.0053 (6)
C210.0192 (6)0.0227 (7)0.0180 (6)0.0015 (5)0.0048 (5)0.0018 (5)
C220.0169 (6)0.0230 (7)0.0160 (6)0.0008 (5)0.0024 (5)0.0014 (5)
C230.0255 (7)0.0195 (7)0.0238 (7)0.0014 (5)0.0084 (6)0.0003 (6)
C240.0278 (7)0.0245 (7)0.0241 (7)0.0009 (6)0.0101 (6)0.0014 (6)
C250.0244 (7)0.0266 (7)0.0239 (7)0.0020 (6)0.0113 (6)0.0018 (6)
C260.0232 (7)0.0229 (7)0.0183 (6)0.0009 (5)0.0048 (5)0.0025 (6)
C270.0504 (10)0.0276 (8)0.0482 (10)0.0014 (7)0.0308 (9)0.0057 (7)
C280.0370 (8)0.0240 (8)0.0341 (8)0.0038 (6)0.0158 (7)0.0005 (6)
C290.0222 (6)0.0186 (7)0.0161 (6)0.0013 (5)0.0056 (5)0.0007 (5)
C300.0229 (6)0.0160 (6)0.0200 (6)0.0002 (5)0.0081 (5)0.0019 (5)
C310.0301 (7)0.0187 (7)0.0226 (7)0.0014 (5)0.0073 (6)0.0044 (6)
C320.0512 (10)0.0353 (9)0.0255 (8)0.0077 (8)0.0172 (7)0.0105 (7)
C330.0475 (9)0.0234 (8)0.0418 (9)0.0019 (7)0.0294 (8)0.0045 (7)
C340.0253 (7)0.0215 (7)0.0252 (7)0.0002 (5)0.0119 (6)0.0005 (6)
C350.0258 (7)0.0175 (7)0.0227 (7)0.0005 (5)0.0080 (6)0.0011 (5)
O1W0.0275 (5)0.0216 (5)0.0202 (5)0.0052 (4)0.0084 (4)0.0029 (4)
Geometric parameters (Å, º) top
O1—C351.4275 (16)C15—H150.9500
O1—H1A0.874 (9)C16—C171.397 (2)
N1—C141.3779 (16)C16—C191.500 (2)
N1—C131.4685 (17)C17—C181.3837 (19)
N1—H10.885 (9)C17—H170.9500
N2—C141.3443 (17)C18—C201.5076 (19)
N2—C181.3451 (17)C19—H19A0.9800
N3—C221.3705 (17)C19—H19B0.9800
N3—C211.4558 (17)C19—H19C0.9800
N3—H30.889 (9)C20—H20A0.9800
N4—C221.3410 (17)C20—H20B0.9800
N4—C261.3578 (17)C20—H20C0.9800
N5—C291.4787 (16)C21—H21A0.9900
N5—C301.4876 (16)C21—H21B0.9900
N5—H50.896 (9)C22—C231.4093 (19)
C1—C61.4039 (17)C23—C241.3744 (19)
C1—C21.4080 (18)C23—H230.9500
C1—C71.5243 (17)C24—C251.401 (2)
C2—C31.4041 (17)C24—C271.506 (2)
C2—C131.5155 (17)C25—C261.377 (2)
C3—C41.4067 (18)C25—H250.9500
C3—C91.5177 (18)C26—C281.5046 (19)
C4—C51.4037 (18)C27—H27A0.9800
C4—C211.5219 (17)C27—H27B0.9800
C5—C61.4120 (17)C27—H27C0.9800
C5—C111.5197 (17)C28—H28A0.9800
C6—C291.5172 (18)C28—H28B0.9800
C7—C81.5284 (19)C28—H28C0.9800
C7—H7A0.9900C29—H29A0.9900
C7—H7B0.9900C29—H29B0.9900
C8—H8A0.9800C30—C351.5310 (18)
C8—H8B0.9800C30—C311.5548 (18)
C8—H8C0.9800C30—C341.5556 (18)
C9—C101.532 (2)C31—C321.531 (2)
C9—H9A0.9900C31—H31A0.9900
C9—H9B0.9900C31—H31B0.9900
C10—H10A0.9800C32—C331.522 (2)
C10—H10B0.9800C32—H32A0.9900
C10—H10C0.9800C32—H32B0.9900
C11—C121.5333 (19)C33—C341.525 (2)
C11—H11A0.9900C33—H33A0.9900
C11—H11B0.9900C33—H33B0.9900
C12—H12A0.9800C34—H34A0.9900
C12—H12B0.9800C34—H34B0.9900
C12—H12C0.9800C35—H35A0.9900
C13—H13A0.9900C35—H35B0.9900
C13—H13B0.9900O1W—H1W0.861 (9)
C14—C151.4001 (18)O1W—H2W0.871 (9)
C15—C161.3824 (18)
C35—O1—H1A112.5 (13)C16—C19—H19B109.5
C14—N1—C13122.12 (11)H19A—C19—H19B109.5
C14—N1—H1112.4 (11)C16—C19—H19C109.5
C13—N1—H1114.0 (11)H19A—C19—H19C109.5
C14—N2—C18117.94 (11)H19B—C19—H19C109.5
C22—N3—C21125.38 (12)C18—C20—H20A109.5
C22—N3—H3116.6 (11)C18—C20—H20B109.5
C21—N3—H3116.7 (11)H20A—C20—H20B109.5
C22—N4—C26116.90 (11)C18—C20—H20C109.5
C29—N5—C30118.35 (10)H20A—C20—H20C109.5
C29—N5—H5108.8 (10)H20B—C20—H20C109.5
C30—N5—H5108.4 (10)N3—C21—C4109.97 (10)
C6—C1—C2119.53 (11)N3—C21—H21A109.7
C6—C1—C7120.77 (11)C4—C21—H21A109.7
C2—C1—C7119.70 (11)N3—C21—H21B109.7
C3—C2—C1120.72 (11)C4—C21—H21B109.7
C3—C2—C13120.66 (11)H21A—C21—H21B108.2
C1—C2—C13118.17 (11)N4—C22—N3118.97 (12)
C2—C3—C4119.15 (11)N4—C22—C23122.97 (12)
C2—C3—C9120.74 (11)N3—C22—C23118.03 (12)
C4—C3—C9120.10 (11)C24—C23—C22119.43 (13)
C5—C4—C3120.60 (11)C24—C23—H23120.3
C5—C4—C21120.03 (11)C22—C23—H23120.3
C3—C4—C21119.19 (11)C23—C24—C25117.79 (13)
C4—C5—C6119.53 (11)C23—C24—C27121.36 (13)
C4—C5—C11120.33 (11)C25—C24—C27120.85 (13)
C6—C5—C11120.12 (11)C26—C25—C24119.63 (12)
C1—C6—C5120.14 (11)C26—C25—H25120.2
C1—C6—C29117.93 (11)C24—C25—H25120.2
C5—C6—C29121.78 (11)N4—C26—C25123.26 (12)
C1—C7—C8111.59 (11)N4—C26—C28115.73 (12)
C1—C7—H7A109.3C25—C26—C28121.01 (12)
C8—C7—H7A109.3C24—C27—H27A109.5
C1—C7—H7B109.3C24—C27—H27B109.5
C8—C7—H7B109.3H27A—C27—H27B109.5
H7A—C7—H7B108.0C24—C27—H27C109.5
C7—C8—H8A109.5H27A—C27—H27C109.5
C7—C8—H8B109.5H27B—C27—H27C109.5
H8A—C8—H8B109.5C26—C28—H28A109.5
C7—C8—H8C109.5C26—C28—H28B109.5
H8A—C8—H8C109.5H28A—C28—H28B109.5
H8B—C8—H8C109.5C26—C28—H28C109.5
C3—C9—C10113.32 (11)H28A—C28—H28C109.5
C3—C9—H9A108.9H28B—C28—H28C109.5
C10—C9—H9A108.9N5—C29—C6108.41 (10)
C3—C9—H9B108.9N5—C29—H29A110.0
C10—C9—H9B108.9C6—C29—H29A110.0
H9A—C9—H9B107.7N5—C29—H29B110.0
C9—C10—H10A109.5C6—C29—H29B110.0
C9—C10—H10B109.5H29A—C29—H29B108.4
H10A—C10—H10B109.5N5—C30—C35106.05 (10)
C9—C10—H10C109.5N5—C30—C31110.47 (11)
H10A—C10—H10C109.5C35—C30—C31109.58 (11)
H10B—C10—H10C109.5N5—C30—C34116.39 (11)
C5—C11—C12113.62 (11)C35—C30—C34109.43 (11)
C5—C11—H11A108.8C31—C30—C34104.86 (10)
C12—C11—H11A108.8C32—C31—C30106.29 (11)
C5—C11—H11B108.8C32—C31—H31A110.5
C12—C11—H11B108.8C30—C31—H31A110.5
H11A—C11—H11B107.7C32—C31—H31B110.5
C11—C12—H12A109.5C30—C31—H31B110.5
C11—C12—H12B109.5H31A—C31—H31B108.7
H12A—C12—H12B109.5C33—C32—C31104.00 (12)
C11—C12—H12C109.5C33—C32—H32A111.0
H12A—C12—H12C109.5C31—C32—H32A111.0
H12B—C12—H12C109.5C33—C32—H32B111.0
N1—C13—C2106.75 (10)C31—C32—H32B111.0
N1—C13—H13A110.4H32A—C32—H32B109.0
C2—C13—H13A110.4C32—C33—C34103.01 (12)
N1—C13—H13B110.4C32—C33—H33A111.2
C2—C13—H13B110.4C34—C33—H33A111.2
H13A—C13—H13B108.6C32—C33—H33B111.2
N2—C14—N1115.60 (11)C34—C33—H33B111.2
N2—C14—C15122.67 (12)H33A—C33—H33B109.1
N1—C14—C15121.72 (12)C33—C34—C30104.58 (11)
C16—C15—C14119.04 (13)C33—C34—H34A110.8
C16—C15—H15120.5C30—C34—H34A110.8
C14—C15—H15120.5C33—C34—H34B110.8
C15—C16—C17118.19 (12)C30—C34—H34B110.8
C15—C16—C19120.87 (13)H34A—C34—H34B108.9
C17—C16—C19120.93 (13)O1—C35—C30113.25 (11)
C18—C17—C16119.44 (12)O1—C35—H35A108.9
C18—C17—H17120.3C30—C35—H35A108.9
C16—C17—H17120.3O1—C35—H35B108.9
N2—C18—C17122.67 (13)C30—C35—H35B108.9
N2—C18—C20115.89 (12)H35A—C35—H35B107.7
C17—C18—C20121.45 (12)H1W—O1W—H2W107.2 (18)
C16—C19—H19A109.5
C6—C1—C2—C33.01 (18)C15—C16—C17—C181.2 (2)
C7—C1—C2—C3176.05 (11)C19—C16—C17—C18177.68 (14)
C6—C1—C2—C13169.44 (11)C14—N2—C18—C172.26 (18)
C7—C1—C2—C1311.50 (17)C14—N2—C18—C20177.50 (11)
C1—C2—C3—C41.77 (18)C16—C17—C18—N20.6 (2)
C13—C2—C3—C4174.02 (11)C16—C17—C18—C20179.14 (13)
C1—C2—C3—C9176.97 (11)C22—N3—C21—C4139.10 (13)
C13—C2—C3—C94.72 (18)C5—C4—C21—N384.62 (14)
C2—C3—C4—C55.90 (18)C3—C4—C21—N390.57 (14)
C9—C3—C4—C5172.84 (11)C26—N4—C22—N3178.80 (11)
C2—C3—C4—C21178.94 (11)C26—N4—C22—C230.68 (18)
C9—C3—C4—C212.32 (18)C21—N3—C22—N40.42 (19)
C3—C4—C5—C65.22 (18)C21—N3—C22—C23178.64 (12)
C21—C4—C5—C6179.67 (11)N4—C22—C23—C240.8 (2)
C3—C4—C5—C11173.26 (11)N3—C22—C23—C24177.36 (12)
C21—C4—C5—C111.85 (18)C22—C23—C24—C251.3 (2)
C2—C1—C6—C53.71 (18)C22—C23—C24—C27178.42 (14)
C7—C1—C6—C5175.34 (11)C23—C24—C25—C260.4 (2)
C2—C1—C6—C29171.98 (11)C27—C24—C25—C26179.31 (14)
C7—C1—C6—C298.97 (17)C22—N4—C26—C251.63 (19)
C4—C5—C6—C10.36 (18)C22—N4—C26—C28178.68 (12)
C11—C5—C6—C1178.12 (11)C24—C25—C26—N41.1 (2)
C4—C5—C6—C29175.88 (11)C24—C25—C26—C28179.23 (13)
C11—C5—C6—C292.60 (18)C30—N5—C29—C6168.54 (10)
C6—C1—C7—C893.07 (14)C1—C6—C29—N574.81 (14)
C2—C1—C7—C885.97 (14)C5—C6—C29—N5100.80 (13)
C2—C3—C9—C1088.30 (15)C29—N5—C30—C35170.13 (10)
C4—C3—C9—C1092.98 (15)C29—N5—C30—C3171.21 (14)
C4—C5—C11—C1294.72 (14)C29—N5—C30—C3448.19 (15)
C6—C5—C11—C1286.81 (15)N5—C30—C31—C32122.98 (12)
C14—N1—C13—C2148.51 (12)C35—C30—C31—C32120.53 (13)
C3—C2—C13—N195.00 (13)C34—C30—C31—C323.17 (15)
C1—C2—C13—N177.45 (14)C30—C31—C32—C3327.13 (16)
C18—N2—C14—N1177.18 (11)C31—C32—C33—C3440.92 (15)
C18—N2—C14—C152.14 (18)C32—C33—C34—C3038.95 (15)
C13—N1—C14—N2154.81 (12)N5—C30—C34—C33144.32 (12)
C13—N1—C14—C1525.87 (18)C35—C30—C34—C3395.53 (13)
N2—C14—C15—C160.36 (19)C31—C30—C34—C3321.93 (14)
N1—C14—C15—C16178.91 (12)N5—C30—C35—O167.44 (13)
C14—C15—C16—C171.31 (19)C31—C30—C35—O1173.32 (11)
C14—C15—C16—C19177.57 (14)C34—C30—C35—O158.86 (14)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C1–C6 and C14–C18/N2 rings, respectively.
D—H···AD—HH···AD···AD—H···A
O1W—H2W···N50.87 (1)1.93 (1)2.8018 (14)175 (2)
O1W—H1W···N2i0.86 (1)2.03 (1)2.8780 (15)166 (2)
O1—H1A···O1Wi0.87 (1)1.83 (1)2.6993 (14)176 (2)
N5—H5···O1Wi0.90 (1)2.52 (1)3.3302 (14)151 (1)
N3—H3···O1i0.89 (1)2.05 (1)2.9115 (15)162 (2)
N1—H1···O1Wi0.89 (1)2.50 (1)3.2618 (16)145 (1)
C32—H32B···Cg1ii0.992.693.666 (2)169
C25—H25···Cg2iii0.952.843.728 (2)156
Symmetry codes: (i) x, y+1, z; (ii) x, y, z; (iii) x+1, y, z.
{1-[(3,5-Bis{[(4,6-dimethylpyridin-2-yl)amino]methyl}-2,4,6-triethylbenzyl)amino]cyclopentyl}methanol methanol monosolvate (1b) top
Crystal data top
C35H51N5O·CH4OZ = 2
Mr = 589.85F(000) = 644
Triclinic, P1Dx = 1.046 Mg m3
a = 12.1169 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.2380 (5) ÅCell parameters from 9915 reflections
c = 13.6258 (5) Åθ = 2.8–30.5°
α = 68.373 (2)°µ = 0.07 mm1
β = 79.379 (2)°T = 100 K
γ = 67.392 (2)°Irregular, colourless
V = 1873.32 (12) Å30.56 × 0.34 × 0.32 mm
Data collection top
Bruker X8 APEXII CCD
diffractometer
Rint = 0.022
phi and ω scansθmax = 26.4°, θmin = 1.8°
32191 measured reflectionsh = 1415
7654 independent reflectionsk = 1516
5160 reflections with I > 2σ(I)l = 017
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.065H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.184 w = 1/[σ2(Fo2) + (0.026P)2 + 3.8856P]
where P = (Fo2 + 2Fc2)/3
S = 1.21(Δ/σ)max < 0.001
7654 reflectionsΔρmax = 0.64 e Å3
410 parametersΔρmin = 0.39 e Å3
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
O11.27014 (18)0.57360 (19)0.78975 (18)0.0337 (5)
H1A1.33080.51590.78680.051*
N10.8131 (3)0.6398 (2)0.68505 (19)0.0298 (6)
H10.848 (3)0.588 (3)0.750 (3)0.030 (8)*
N20.7667 (3)0.6725 (3)0.5157 (2)0.0382 (7)
N30.6133 (2)0.73074 (19)1.09127 (18)0.0208 (5)
H30.656 (3)0.667 (3)1.081 (2)0.023 (8)*
N40.53696 (19)0.61277 (18)1.23326 (17)0.0182 (4)
N51.12190 (19)0.67304 (18)0.94010 (18)0.0190 (4)
H51.110 (3)0.628 (3)0.910 (3)0.027 (8)*
C10.9042 (2)0.7808 (2)0.78008 (19)0.0159 (5)
C20.7918 (2)0.7816 (2)0.76743 (19)0.0179 (5)
C30.6984 (2)0.7982 (2)0.8449 (2)0.0186 (5)
C40.7184 (2)0.8192 (2)0.93271 (19)0.0173 (5)
C50.8303 (2)0.8189 (2)0.94606 (19)0.0164 (5)
C60.9235 (2)0.7990 (2)0.86997 (19)0.0160 (5)
C71.0021 (2)0.7657 (2)0.6940 (2)0.0207 (5)
H7A0.99170.71670.65890.025*
H7B1.08090.72520.72640.025*
C81.0008 (3)0.8814 (2)0.6114 (2)0.0287 (6)
H8A0.92350.92120.57810.043*
H8B1.06520.86770.55750.043*
H8C1.01270.92960.64560.043*
C90.5782 (2)0.7944 (2)0.8331 (2)0.0249 (6)
H9A0.54170.76560.90430.030*
H9B0.59090.73890.79600.030*
C100.4912 (3)0.9125 (3)0.7722 (3)0.0349 (7)
H10A0.47980.96860.80750.052*
H10B0.41410.90560.77010.052*
H10C0.52410.93910.69990.052*
C110.8503 (2)0.8411 (2)1.0417 (2)0.0195 (5)
H11A0.93400.79591.06220.023*
H11B0.79710.81381.10160.023*
C120.8259 (3)0.9694 (2)1.0213 (2)0.0283 (6)
H12A0.87920.99670.96280.042*
H12B0.84060.97911.08510.042*
H12C0.74251.01441.00300.042*
C130.7709 (3)0.7627 (2)0.6698 (2)0.0240 (6)
H13A0.68440.79710.65650.029*
H13B0.81400.80160.60740.029*
C140.8157 (3)0.5977 (3)0.6068 (2)0.0301 (7)
C150.8695 (3)0.4779 (3)0.6252 (3)0.0351 (7)
H150.90320.42700.69100.042*
C160.8722 (3)0.4360 (4)0.5462 (3)0.0480 (10)
C170.8216 (4)0.5129 (4)0.4515 (3)0.0548 (12)
H170.82220.48540.39600.066*
C180.7710 (3)0.6284 (4)0.4385 (3)0.0516 (11)
C190.9332 (4)0.3088 (4)0.5622 (4)0.0662 (14)
H19A0.89310.28530.52250.099*
H19B0.92890.26460.63750.099*
H19C1.01720.29360.53680.099*
C200.7149 (5)0.7156 (5)0.3377 (3)0.0755 (16)
H20A0.62930.75310.35200.113*
H20B0.72520.67630.28630.113*
H20C0.75350.77410.30890.113*
C210.6162 (2)0.8401 (2)1.0146 (2)0.0200 (5)
H21A0.62670.88791.05100.024*
H21B0.53930.88280.97910.024*
C220.5286 (2)0.7214 (2)1.17214 (19)0.0168 (5)
C230.4398 (2)0.8186 (2)1.1916 (2)0.0183 (5)
H230.43440.89451.14600.022*
C240.3604 (2)0.8028 (2)1.2778 (2)0.0206 (5)
C250.3712 (2)0.6901 (2)1.3418 (2)0.0226 (5)
H250.31850.67671.40220.027*
C260.4592 (2)0.5973 (2)1.3170 (2)0.0211 (5)
C270.2644 (3)0.9050 (2)1.3014 (2)0.0293 (6)
H27A0.29000.97261.27160.044*
H27B0.25050.88731.37810.044*
H27C0.19020.92181.26980.044*
C280.4714 (3)0.4746 (2)1.3806 (2)0.0282 (6)
H28A0.44290.44191.34060.042*
H28B0.42360.47241.44720.042*
H28C0.55560.42911.39560.042*
C291.0471 (2)0.7940 (2)0.8843 (2)0.0191 (5)
H29A1.08580.82310.81440.023*
H29B1.03980.84420.92570.023*
C301.2540 (2)0.6488 (2)0.9314 (2)0.0212 (5)
C311.2823 (2)0.7329 (2)0.9663 (2)0.0277 (6)
H31A1.36540.73110.94410.033*
H31B1.22640.81300.93670.033*
C321.2660 (3)0.6884 (3)1.0860 (3)0.0313 (7)
H32A1.18010.70991.10900.038*
H32B1.30610.71921.11940.038*
C331.3256 (3)0.5566 (3)1.1131 (2)0.0308 (6)
H33A1.28570.51591.17700.037*
H33B1.41130.53181.12610.037*
C341.3113 (2)0.5300 (2)1.0158 (2)0.0265 (6)
H34A1.25900.48301.03460.032*
H34B1.39010.48680.98890.032*
C351.3038 (2)0.6496 (2)0.8197 (2)0.0270 (6)
H35A1.27280.72920.76940.032*
H35B1.39220.62490.81700.032*
O1A0.95054 (19)0.4462 (2)0.85754 (17)0.0358 (5)
H1AA0.93300.40310.91620.054*
C1A1.0583 (3)0.4590 (3)0.8631 (2)0.0296 (6)
H1A11.06270.53080.80870.044*
H1A21.12560.39290.85150.044*
H1A31.06230.46220.93310.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0203 (10)0.0337 (12)0.0483 (13)0.0011 (9)0.0023 (9)0.0275 (11)
N10.0507 (16)0.0266 (13)0.0192 (12)0.0167 (12)0.0054 (11)0.0102 (10)
N20.0466 (16)0.0630 (19)0.0195 (12)0.0329 (15)0.0007 (11)0.0154 (12)
N30.0201 (11)0.0157 (11)0.0223 (11)0.0041 (9)0.0068 (9)0.0074 (9)
N40.0167 (10)0.0180 (10)0.0200 (11)0.0060 (8)0.0019 (8)0.0075 (9)
N50.0153 (10)0.0168 (10)0.0252 (11)0.0034 (8)0.0012 (8)0.0094 (9)
C10.0184 (12)0.0112 (11)0.0143 (11)0.0024 (9)0.0019 (9)0.0041 (9)
C20.0222 (13)0.0144 (11)0.0149 (12)0.0045 (10)0.0027 (10)0.0035 (9)
C30.0196 (12)0.0133 (11)0.0198 (12)0.0042 (9)0.0008 (10)0.0036 (10)
C40.0175 (12)0.0149 (11)0.0170 (12)0.0053 (9)0.0017 (9)0.0039 (9)
C50.0186 (12)0.0140 (11)0.0151 (11)0.0034 (9)0.0004 (9)0.0061 (9)
C60.0150 (12)0.0119 (11)0.0194 (12)0.0028 (9)0.0002 (9)0.0058 (9)
C70.0214 (13)0.0223 (13)0.0177 (12)0.0066 (10)0.0038 (10)0.0090 (10)
C80.0338 (16)0.0219 (14)0.0242 (14)0.0081 (12)0.0097 (12)0.0076 (11)
C90.0213 (13)0.0315 (15)0.0254 (14)0.0139 (11)0.0010 (11)0.0082 (12)
C100.0247 (15)0.0402 (18)0.0346 (17)0.0095 (13)0.0074 (12)0.0057 (14)
C110.0220 (13)0.0199 (13)0.0175 (12)0.0054 (10)0.0007 (10)0.0097 (10)
C120.0347 (16)0.0196 (13)0.0317 (15)0.0048 (12)0.0030 (12)0.0140 (12)
C130.0304 (15)0.0230 (13)0.0194 (13)0.0114 (11)0.0015 (11)0.0056 (11)
C140.0360 (16)0.0473 (18)0.0230 (14)0.0286 (14)0.0079 (12)0.0184 (13)
C150.0389 (17)0.0447 (18)0.0386 (17)0.0292 (15)0.0183 (14)0.0265 (15)
C160.046 (2)0.077 (3)0.056 (2)0.045 (2)0.0341 (18)0.053 (2)
C170.060 (2)0.110 (4)0.044 (2)0.065 (3)0.0349 (18)0.060 (2)
C180.051 (2)0.110 (4)0.0274 (17)0.058 (2)0.0143 (15)0.037 (2)
C190.066 (3)0.088 (3)0.089 (3)0.052 (3)0.052 (2)0.078 (3)
C200.083 (3)0.142 (5)0.030 (2)0.066 (3)0.001 (2)0.033 (3)
C210.0188 (12)0.0170 (12)0.0203 (13)0.0051 (10)0.0046 (10)0.0059 (10)
C220.0153 (12)0.0199 (12)0.0182 (12)0.0060 (10)0.0002 (9)0.0098 (10)
C230.0166 (12)0.0162 (12)0.0192 (12)0.0034 (9)0.0013 (9)0.0061 (10)
C240.0185 (12)0.0226 (13)0.0210 (13)0.0063 (10)0.0041 (10)0.0110 (11)
C250.0180 (12)0.0250 (14)0.0232 (13)0.0073 (11)0.0057 (10)0.0092 (11)
C260.0188 (13)0.0207 (13)0.0228 (13)0.0074 (10)0.0020 (10)0.0069 (11)
C270.0268 (14)0.0202 (13)0.0314 (15)0.0023 (11)0.0117 (12)0.0106 (12)
C280.0314 (15)0.0211 (14)0.0270 (14)0.0098 (12)0.0087 (12)0.0064 (11)
C290.0200 (12)0.0168 (12)0.0214 (13)0.0070 (10)0.0031 (10)0.0085 (10)
C300.0147 (12)0.0198 (13)0.0309 (14)0.0070 (10)0.0028 (10)0.0111 (11)
C310.0189 (13)0.0237 (14)0.0447 (17)0.0077 (11)0.0020 (12)0.0152 (13)
C320.0240 (14)0.0360 (16)0.0426 (18)0.0095 (12)0.0047 (13)0.0219 (14)
C330.0241 (14)0.0330 (16)0.0354 (16)0.0110 (12)0.0023 (12)0.0097 (13)
C340.0197 (13)0.0242 (14)0.0348 (16)0.0058 (11)0.0008 (11)0.0116 (12)
C350.0168 (13)0.0254 (14)0.0356 (16)0.0063 (11)0.0066 (11)0.0114 (12)
O1A0.0292 (11)0.0375 (12)0.0312 (11)0.0152 (9)0.0019 (9)0.0033 (9)
C1A0.0297 (15)0.0257 (14)0.0330 (16)0.0124 (12)0.0041 (12)0.0089 (12)
Geometric parameters (Å, º) top
O1—C351.423 (4)C16—C171.386 (6)
O1—H1A0.8400C16—C191.503 (6)
N1—C141.364 (4)C17—C181.366 (6)
N1—C131.451 (4)C17—H170.9500
N1—H10.94 (3)C18—C201.501 (6)
N2—C141.337 (4)C19—H19A0.9800
N2—C181.363 (4)C19—H19B0.9800
N3—C221.365 (3)C19—H19C0.9800
N3—C211.448 (3)C20—H20A0.9800
N3—H30.85 (3)C20—H20B0.9800
N4—C221.345 (3)C20—H20C0.9800
N4—C261.346 (3)C21—H21A0.9900
N5—C291.485 (3)C21—H21B0.9900
N5—C301.497 (3)C22—C231.402 (3)
N5—H50.90 (3)C23—C241.381 (3)
C1—C21.400 (4)C23—H230.9500
C1—C61.407 (3)C24—C251.391 (4)
C1—C71.517 (3)C24—C271.503 (3)
C2—C31.408 (3)C25—C261.388 (4)
C2—C131.522 (3)C25—H250.9500
C3—C41.404 (4)C26—C281.495 (4)
C3—C91.517 (4)C27—H27A0.9800
C4—C51.398 (3)C27—H27B0.9800
C4—C211.520 (3)C27—H27C0.9800
C5—C61.401 (3)C28—H28A0.9800
C5—C111.515 (3)C28—H28B0.9800
C6—C291.518 (3)C28—H28C0.9800
C7—C81.526 (4)C29—H29A0.9900
C7—H7A0.9900C29—H29B0.9900
C7—H7B0.9900C30—C311.525 (4)
C8—H8A0.9800C30—C351.527 (4)
C8—H8B0.9800C30—C341.549 (4)
C8—H8C0.9800C31—C321.519 (4)
C9—C101.531 (4)C31—H31A0.9900
C9—H9A0.9900C31—H31B0.9900
C9—H9B0.9900C32—C331.536 (4)
C10—H10A0.9800C32—H32A0.9900
C10—H10B0.9800C32—H32B0.9900
C10—H10C0.9800C33—C341.545 (4)
C11—C121.531 (4)C33—H33A0.9900
C11—H11A0.9900C33—H33B0.9900
C11—H11B0.9900C34—H34A0.9900
C12—H12A0.9800C34—H34B0.9900
C12—H12B0.9800C35—H35A0.9900
C12—H12C0.9800C35—H35B0.9900
C13—H13A0.9900O1A—C1A1.399 (4)
C13—H13B0.9900O1A—H1AA0.8400
C14—C151.406 (5)C1A—H1A10.9800
C15—C161.371 (4)C1A—H1A20.9800
C15—H150.9500C1A—H1A30.9800
C35—O1—H1A109.5H19A—C19—H19C109.5
C14—N1—C13122.7 (3)H19B—C19—H19C109.5
C14—N1—H1119 (2)C18—C20—H20A109.5
C13—N1—H1118 (2)C18—C20—H20B109.5
C14—N2—C18117.3 (3)H20A—C20—H20B109.5
C22—N3—C21123.8 (2)C18—C20—H20C109.5
C22—N3—H3114 (2)H20A—C20—H20C109.5
C21—N3—H3121 (2)H20B—C20—H20C109.5
C22—N4—C26118.8 (2)N3—C21—C4110.2 (2)
C29—N5—C30115.6 (2)N3—C21—H21A109.6
C29—N5—H5106 (2)C4—C21—H21A109.6
C30—N5—H5106 (2)N3—C21—H21B109.6
C2—C1—C6119.8 (2)C4—C21—H21B109.6
C2—C1—C7119.4 (2)H21A—C21—H21B108.1
C6—C1—C7120.7 (2)N4—C22—N3115.6 (2)
C1—C2—C3120.5 (2)N4—C22—C23122.0 (2)
C1—C2—C13119.7 (2)N3—C22—C23122.3 (2)
C3—C2—C13119.8 (2)C24—C23—C22119.2 (2)
C4—C3—C2118.8 (2)C24—C23—H23120.4
C4—C3—C9120.7 (2)C22—C23—H23120.4
C2—C3—C9120.5 (2)C23—C24—C25118.4 (2)
C5—C4—C3121.1 (2)C23—C24—C27120.6 (2)
C5—C4—C21120.5 (2)C25—C24—C27121.0 (2)
C3—C4—C21118.4 (2)C26—C25—C24119.8 (2)
C4—C5—C6119.6 (2)C26—C25—H25120.1
C4—C5—C11120.3 (2)C24—C25—H25120.1
C6—C5—C11120.1 (2)N4—C26—C25121.9 (2)
C5—C6—C1120.1 (2)N4—C26—C28116.3 (2)
C5—C6—C29120.7 (2)C25—C26—C28121.8 (2)
C1—C6—C29119.2 (2)C24—C27—H27A109.5
C1—C7—C8112.1 (2)C24—C27—H27B109.5
C1—C7—H7A109.2H27A—C27—H27B109.5
C8—C7—H7A109.2C24—C27—H27C109.5
C1—C7—H7B109.2H27A—C27—H27C109.5
C8—C7—H7B109.2H27B—C27—H27C109.5
H7A—C7—H7B107.9C26—C28—H28A109.5
C7—C8—H8A109.5C26—C28—H28B109.5
C7—C8—H8B109.5H28A—C28—H28B109.5
H8A—C8—H8B109.5C26—C28—H28C109.5
C7—C8—H8C109.5H28A—C28—H28C109.5
H8A—C8—H8C109.5H28B—C28—H28C109.5
H8B—C8—H8C109.5N5—C29—C6110.1 (2)
C3—C9—C10113.1 (2)N5—C29—H29A109.6
C3—C9—H9A109.0C6—C29—H29A109.6
C10—C9—H9A109.0N5—C29—H29B109.6
C3—C9—H9B109.0C6—C29—H29B109.6
C10—C9—H9B109.0H29A—C29—H29B108.1
H9A—C9—H9B107.8N5—C30—C31110.6 (2)
C9—C10—H10A109.5N5—C30—C35110.3 (2)
C9—C10—H10B109.5C31—C30—C35113.0 (2)
H10A—C10—H10B109.5N5—C30—C34107.1 (2)
C9—C10—H10C109.5C31—C30—C34103.3 (2)
H10A—C10—H10C109.5C35—C30—C34112.1 (2)
H10B—C10—H10C109.5C32—C31—C30103.5 (2)
C5—C11—C12112.6 (2)C32—C31—H31A111.1
C5—C11—H11A109.1C30—C31—H31A111.1
C12—C11—H11A109.1C32—C31—H31B111.1
C5—C11—H11B109.1C30—C31—H31B111.1
C12—C11—H11B109.1H31A—C31—H31B109.0
H11A—C11—H11B107.8C31—C32—C33103.2 (2)
C11—C12—H12A109.5C31—C32—H32A111.1
C11—C12—H12B109.5C33—C32—H32A111.1
H12A—C12—H12B109.5C31—C32—H32B111.1
C11—C12—H12C109.5C33—C32—H32B111.1
H12A—C12—H12C109.5H32A—C32—H32B109.1
H12B—C12—H12C109.5C32—C33—C34105.5 (2)
N1—C13—C2109.9 (2)C32—C33—H33A110.6
N1—C13—H13A109.7C34—C33—H33A110.6
C2—C13—H13A109.7C32—C33—H33B110.6
N1—C13—H13B109.7C34—C33—H33B110.6
C2—C13—H13B109.7H33A—C33—H33B108.8
H13A—C13—H13B108.2C33—C34—C30106.2 (2)
N2—C14—N1118.4 (3)C33—C34—H34A110.5
N2—C14—C15122.8 (3)C30—C34—H34A110.5
N1—C14—C15118.8 (3)C33—C34—H34B110.5
C16—C15—C14118.6 (4)C30—C34—H34B110.5
C16—C15—H15120.7H34A—C34—H34B108.7
C14—C15—H15120.7O1—C35—C30110.5 (2)
C15—C16—C17119.0 (4)O1—C35—H35A109.5
C15—C16—C19119.8 (4)C30—C35—H35A109.5
C17—C16—C19121.2 (3)O1—C35—H35B109.5
C18—C17—C16119.6 (3)C30—C35—H35B109.5
C18—C17—H17120.2H35A—C35—H35B108.1
C16—C17—H17120.2C1A—O1A—H1AA109.5
N2—C18—C17122.7 (4)O1A—C1A—H1A1109.5
N2—C18—C20115.5 (4)O1A—C1A—H1A2109.5
C17—C18—C20121.8 (4)H1A1—C1A—H1A2109.5
C16—C19—H19A109.5O1A—C1A—H1A3109.5
C16—C19—H19B109.5H1A1—C1A—H1A3109.5
H19A—C19—H19B109.5H1A2—C1A—H1A3109.5
C16—C19—H19C109.5
C6—C1—C2—C31.2 (4)C15—C16—C17—C180.4 (5)
C7—C1—C2—C3178.5 (2)C19—C16—C17—C18177.6 (3)
C6—C1—C2—C13179.5 (2)C14—N2—C18—C170.6 (5)
C7—C1—C2—C132.3 (3)C14—N2—C18—C20180.0 (3)
C1—C2—C3—C42.8 (4)C16—C17—C18—N20.6 (5)
C13—C2—C3—C4177.9 (2)C16—C17—C18—C20180.0 (3)
C1—C2—C3—C9177.7 (2)C22—N3—C21—C4177.5 (2)
C13—C2—C3—C91.6 (4)C5—C4—C21—N393.1 (3)
C2—C3—C4—C52.7 (4)C3—C4—C21—N385.7 (3)
C9—C3—C4—C5177.8 (2)C26—N4—C22—N3177.4 (2)
C2—C3—C4—C21178.5 (2)C26—N4—C22—C231.5 (4)
C9—C3—C4—C211.0 (3)C21—N3—C22—N4177.4 (2)
C3—C4—C5—C61.0 (4)C21—N3—C22—C233.7 (4)
C21—C4—C5—C6179.7 (2)N4—C22—C23—C241.8 (4)
C3—C4—C5—C11179.6 (2)N3—C22—C23—C24177.0 (2)
C21—C4—C5—C110.9 (3)C22—C23—C24—C250.5 (4)
C4—C5—C6—C10.7 (4)C22—C23—C24—C27179.7 (3)
C11—C5—C6—C1178.7 (2)C23—C24—C25—C260.9 (4)
C4—C5—C6—C29177.8 (2)C27—C24—C25—C26178.8 (3)
C11—C5—C6—C292.8 (3)C22—N4—C26—C250.0 (4)
C2—C1—C6—C50.6 (3)C22—N4—C26—C28178.8 (2)
C7—C1—C6—C5176.6 (2)C24—C25—C26—N41.3 (4)
C2—C1—C6—C29178.0 (2)C24—C25—C26—C28177.5 (3)
C7—C1—C6—C294.8 (3)C30—N5—C29—C6162.4 (2)
C2—C1—C7—C889.8 (3)C5—C6—C29—N590.9 (3)
C6—C1—C7—C887.4 (3)C1—C6—C29—N587.6 (3)
C4—C3—C9—C1090.5 (3)C29—N5—C30—C3154.1 (3)
C2—C3—C9—C1089.0 (3)C29—N5—C30—C3571.7 (3)
C4—C5—C11—C1291.6 (3)C29—N5—C30—C34166.1 (2)
C6—C5—C11—C1287.8 (3)N5—C30—C31—C3275.2 (3)
C14—N1—C13—C2173.9 (3)C35—C30—C31—C32160.5 (2)
C1—C2—C13—N183.0 (3)C34—C30—C31—C3239.2 (3)
C3—C2—C13—N196.2 (3)C30—C31—C32—C3342.6 (3)
C18—N2—C14—N1179.7 (3)C31—C32—C33—C3429.1 (3)
C18—N2—C14—C150.4 (4)C32—C33—C34—C305.1 (3)
C13—N1—C14—N26.6 (4)N5—C30—C34—C3396.1 (2)
C13—N1—C14—C15173.5 (3)C31—C30—C34—C3320.7 (3)
N2—C14—C15—C160.3 (4)C35—C30—C34—C33142.8 (2)
N1—C14—C15—C16179.8 (3)N5—C30—C35—O152.9 (3)
C14—C15—C16—C170.3 (4)C31—C30—C35—O1177.4 (2)
C14—C15—C16—C19177.8 (3)C34—C30—C35—O166.3 (3)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg3 are the centroids of the C1–C6 and C22–C26/N4 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1···O1A0.94 (3)2.01 (3)2.930 (3)162 (2)
C15—H15···O1A0.952.563.318 (3)137
N5—H5···O10.90 (3)2.36 (3)2.823 (3)112 (2)
O1—H1A···N4i0.841.902.741 (3)174
O1A—H1AA···N5i0.841.972.798 (3)170
C27—H27A···Cg1ii0.982.673.541 (3)148
C32—H32B···Cg3iii0.982.693.614 (3)156
Symmetry codes: (i) x+2, y+1, z+2; (ii) x+1, y+2, z+2; (iii) x+1, y, z.
 

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