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
CCDC references: 2032104; 2032103
Key indicators
Structure: 1a
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.043
- wR factor = 0.114
- Data-to-parameter ratio = 18.2
Structure: 1b
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.005 Å
- R factor = 0.065
- wR factor = 0.184
- Data-to-parameter ratio = 18.7
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
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·H2O | F(000) = 1256 |
Mr = 575.82 | Dx = 1.151 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.2239 (7) Å | Cell parameters from 9674 reflections |
b = 15.3576 (8) Å | θ = 2.2–28.2° |
c = 17.1061 (8) Å | µ = 0.07 mm−1 |
β = 107.0289 (17)° | T = 100 K |
V = 3321.7 (3) Å3 | Irregular, colourless |
Z = 4 | 0.45 × 0.32 × 0.10 mm |
Data collection top
Bruker X8 APEXII CCD diffractometer | Rint = 0.034 |
phi and ω scans | θmax = 27.4°, θmin = 2.1° |
28794 measured reflections | h = −17→17 |
7467 independent reflections | k = −19→17 |
5791 reflections with I > 2σ(I) | l = −22→21 |
Refinement top
Refinement on F2 | 6 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.043 | H 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 reflections | Δρmax = 0.27 e Å−3 |
410 parameters | Δρmin = −0.20 e Å−3 |
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 | Uiso*/Ueq | |
O1 | −0.21807 (7) | 0.54810 (6) | 0.00959 (6) | 0.0238 (2) | |
N1 | −0.11044 (9) | 0.24557 (8) | −0.12255 (7) | 0.0218 (2) | |
H1 | −0.0834 (13) | 0.2969 (7) | −0.1039 (10) | 0.036 (5)* | |
N2 | −0.23912 (9) | 0.33295 (7) | −0.20586 (6) | 0.0198 (2) | |
N3 | 0.33881 (9) | 0.29584 (8) | 0.05481 (7) | 0.0223 (3) | |
H3 | 0.3046 (12) | 0.3464 (7) | 0.0466 (10) | 0.036 (5)* | |
N4 | 0.44662 (8) | 0.20100 (7) | 0.00817 (7) | 0.0201 (2) | |
N5 | −0.03784 (8) | 0.45806 (7) | 0.12196 (6) | 0.0176 (2) | |
H5 | −0.0752 (11) | 0.4402 (10) | 0.0720 (6) | 0.024 (4)* | |
C1 | −0.03521 (10) | 0.26699 (8) | 0.06516 (7) | 0.0163 (3) | |
C2 | −0.00019 (10) | 0.21235 (8) | 0.01228 (7) | 0.0161 (3) | |
C3 | 0.10826 (10) | 0.20103 (8) | 0.02240 (7) | 0.0167 (3) | |
C4 | 0.18206 (10) | 0.24315 (8) | 0.08766 (7) | 0.0169 (3) | |
C5 | 0.14833 (10) | 0.30214 (8) | 0.13754 (7) | 0.0172 (3) | |
C6 | 0.03906 (10) | 0.31377 (8) | 0.12622 (7) | 0.0166 (3) | |
C7 | −0.15304 (10) | 0.27362 (9) | 0.05636 (8) | 0.0197 (3) | |
H7A | −0.1936 | 0.2693 | −0.0022 | 0.024* | |
H7B | −0.1682 | 0.3311 | 0.0766 | 0.024* | |
C8 | −0.18900 (11) | 0.20182 (10) | 0.10409 (9) | 0.0264 (3) | |
H8A | −0.1753 | 0.1448 | 0.0835 | 0.040* | |
H8B | −0.2649 | 0.2080 | 0.0971 | 0.040* | |
H8C | −0.1499 | 0.2066 | 0.1622 | 0.040* | |
C9 | 0.14599 (11) | 0.14569 (9) | −0.03707 (8) | 0.0223 (3) | |
H9A | 0.2149 | 0.1684 | −0.0399 | 0.027* | |
H9B | 0.0949 | 0.1512 | −0.0922 | 0.027* | |
C10 | 0.15839 (13) | 0.04917 (10) | −0.01346 (10) | 0.0335 (4) | |
H10A | 0.2087 | 0.0431 | 0.0412 | 0.050* | |
H10B | 0.1847 | 0.0173 | −0.0532 | 0.050* | |
H10C | 0.0897 | 0.0254 | −0.0133 | 0.050* | |
C11 | 0.22863 (10) | 0.35482 (9) | 0.20189 (8) | 0.0215 (3) | |
H11A | 0.1992 | 0.4135 | 0.2052 | 0.026* | |
H11B | 0.2932 | 0.3620 | 0.1845 | 0.026* | |
C12 | 0.25915 (12) | 0.31327 (10) | 0.28712 (8) | 0.0288 (3) | |
H12A | 0.1950 | 0.3008 | 0.3028 | 0.043* | |
H12B | 0.3042 | 0.3535 | 0.3268 | 0.043* | |
H12C | 0.2977 | 0.2590 | 0.2863 | 0.043* | |
C13 | −0.08201 (10) | 0.17532 (9) | −0.06179 (8) | 0.0190 (3) | |
H13A | −0.0524 | 0.1251 | −0.0840 | 0.023* | |
H13B | −0.1451 | 0.1556 | −0.0468 | 0.023* | |
C14 | −0.21009 (10) | 0.25244 (9) | −0.17714 (7) | 0.0181 (3) | |
C15 | −0.27565 (10) | 0.17971 (9) | −0.20134 (8) | 0.0206 (3) | |
H15 | −0.2528 | 0.1238 | −0.1796 | 0.025* | |
C16 | −0.37413 (11) | 0.19050 (9) | −0.25737 (9) | 0.0246 (3) | |
C17 | −0.40303 (11) | 0.27384 (9) | −0.28877 (8) | 0.0237 (3) | |
H17 | −0.4696 | 0.2832 | −0.3282 | 0.028* | |
C18 | −0.33386 (10) | 0.34256 (9) | −0.26202 (8) | 0.0205 (3) | |
C19 | −0.44869 (13) | 0.11508 (11) | −0.28255 (12) | 0.0432 (4) | |
H19A | −0.4083 | 0.0607 | −0.2750 | 0.065* | |
H19B | −0.4893 | 0.1213 | −0.3402 | 0.065* | |
H19C | −0.4972 | 0.1140 | −0.2489 | 0.065* | |
C20 | −0.36075 (12) | 0.43342 (10) | −0.29491 (9) | 0.0282 (3) | |
H20A | −0.3585 | 0.4732 | −0.2497 | 0.042* | |
H20B | −0.4319 | 0.4338 | −0.3338 | 0.042* | |
H20C | −0.3094 | 0.4523 | −0.3227 | 0.042* | |
C21 | 0.29964 (10) | 0.22967 (9) | 0.09957 (8) | 0.0201 (3) | |
H21A | 0.3387 | 0.2332 | 0.1585 | 0.024* | |
H21B | 0.3115 | 0.1711 | 0.0797 | 0.024* | |
C22 | 0.40895 (10) | 0.28164 (9) | 0.01095 (8) | 0.0191 (3) | |
C23 | 0.44048 (11) | 0.35362 (9) | −0.02740 (8) | 0.0227 (3) | |
H23 | 0.4112 | 0.4096 | −0.0245 | 0.027* | |
C24 | 0.51400 (11) | 0.34216 (9) | −0.06903 (9) | 0.0249 (3) | |
C25 | 0.55286 (11) | 0.25789 (9) | −0.07272 (9) | 0.0241 (3) | |
H25 | 0.6034 | 0.2474 | −0.1013 | 0.029* | |
C26 | 0.51739 (10) | 0.19036 (9) | −0.03474 (8) | 0.0217 (3) | |
C27 | 0.55221 (14) | 0.41751 (11) | −0.10917 (11) | 0.0386 (4) | |
H27A | 0.5240 | 0.4122 | −0.1687 | 0.058* | |
H27B | 0.6297 | 0.4171 | −0.0935 | 0.058* | |
H27C | 0.5278 | 0.4723 | −0.0914 | 0.058* | |
C28 | 0.55646 (13) | 0.09887 (10) | −0.03838 (10) | 0.0306 (3) | |
H28A | 0.5931 | 0.0787 | 0.0170 | 0.046* | |
H28B | 0.6054 | 0.0978 | −0.0717 | 0.046* | |
H28C | 0.4963 | 0.0605 | −0.0629 | 0.046* | |
C29 | −0.00203 (10) | 0.38089 (8) | 0.17448 (8) | 0.0190 (3) | |
H29A | −0.0616 | 0.3563 | 0.1914 | 0.023* | |
H29B | 0.0547 | 0.3976 | 0.2243 | 0.023* | |
C30 | −0.10008 (10) | 0.52576 (8) | 0.14971 (8) | 0.0192 (3) | |
C31 | −0.02821 (11) | 0.57698 (9) | 0.22365 (8) | 0.0239 (3) | |
H31A | 0.0443 | 0.5526 | 0.2400 | 0.029* | |
H31B | −0.0245 | 0.6391 | 0.2094 | 0.029* | |
C32 | −0.07871 (14) | 0.56730 (11) | 0.29311 (9) | 0.0360 (4) | |
H32A | −0.0488 | 0.5167 | 0.3281 | 0.043* | |
H32B | −0.0677 | 0.6204 | 0.3274 | 0.043* | |
C33 | −0.19561 (13) | 0.55366 (10) | 0.24928 (10) | 0.0341 (4) | |
H33A | −0.2308 | 0.6094 | 0.2284 | 0.041* | |
H33B | −0.2323 | 0.5265 | 0.2859 | 0.041* | |
C34 | −0.19394 (11) | 0.49275 (9) | 0.17924 (8) | 0.0230 (3) | |
H34A | −0.2613 | 0.4962 | 0.1346 | 0.028* | |
H34B | −0.1823 | 0.4317 | 0.1985 | 0.028* | |
C35 | −0.14183 (11) | 0.58756 (9) | 0.07718 (8) | 0.0218 (3) | |
H35A | −0.1743 | 0.6388 | 0.0954 | 0.026* | |
H35B | −0.0816 | 0.6084 | 0.0589 | 0.026* | |
O1W | 0.12410 (8) | 0.54814 (6) | 0.08143 (6) | 0.0228 (2) | |
H1A | −0.1888 (14) | 0.5189 (11) | −0.0219 (10) | 0.053 (6)* | |
H1W | 0.1623 (13) | 0.5760 (11) | 0.1234 (8) | 0.049 (6)* | |
H2W | 0.0765 (13) | 0.5196 (12) | 0.0970 (12) | 0.056 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0248 (5) | 0.0247 (5) | 0.0211 (5) | 0.0028 (4) | 0.0057 (4) | −0.0022 (4) |
N1 | 0.0216 (6) | 0.0227 (6) | 0.0174 (5) | −0.0049 (5) | 0.0001 (5) | 0.0022 (5) |
N2 | 0.0228 (6) | 0.0218 (6) | 0.0145 (5) | −0.0014 (4) | 0.0050 (4) | −0.0001 (5) |
N3 | 0.0219 (6) | 0.0215 (6) | 0.0262 (6) | 0.0011 (5) | 0.0114 (5) | 0.0022 (5) |
N4 | 0.0202 (5) | 0.0211 (6) | 0.0181 (5) | −0.0012 (4) | 0.0044 (4) | 0.0001 (5) |
N5 | 0.0225 (5) | 0.0153 (5) | 0.0154 (5) | 0.0005 (4) | 0.0063 (4) | −0.0017 (4) |
C1 | 0.0194 (6) | 0.0137 (6) | 0.0158 (6) | 0.0003 (5) | 0.0052 (5) | 0.0049 (5) |
C2 | 0.0203 (6) | 0.0123 (6) | 0.0143 (6) | −0.0016 (5) | 0.0031 (5) | 0.0026 (5) |
C3 | 0.0225 (6) | 0.0141 (6) | 0.0145 (6) | 0.0010 (5) | 0.0069 (5) | 0.0029 (5) |
C4 | 0.0181 (6) | 0.0172 (6) | 0.0150 (6) | 0.0002 (5) | 0.0045 (5) | 0.0045 (5) |
C5 | 0.0207 (6) | 0.0165 (6) | 0.0135 (6) | −0.0013 (5) | 0.0036 (5) | 0.0025 (5) |
C6 | 0.0213 (6) | 0.0145 (6) | 0.0145 (6) | 0.0000 (5) | 0.0060 (5) | 0.0016 (5) |
C7 | 0.0196 (6) | 0.0179 (6) | 0.0214 (7) | 0.0000 (5) | 0.0058 (5) | −0.0004 (5) |
C8 | 0.0254 (7) | 0.0261 (8) | 0.0303 (8) | −0.0017 (6) | 0.0121 (6) | 0.0027 (6) |
C9 | 0.0238 (7) | 0.0241 (7) | 0.0199 (7) | 0.0007 (5) | 0.0079 (5) | −0.0034 (6) |
C10 | 0.0371 (8) | 0.0227 (8) | 0.0425 (9) | 0.0041 (6) | 0.0144 (7) | −0.0069 (7) |
C11 | 0.0207 (6) | 0.0236 (7) | 0.0189 (6) | −0.0018 (5) | 0.0037 (5) | −0.0033 (6) |
C12 | 0.0301 (7) | 0.0345 (8) | 0.0177 (7) | −0.0014 (6) | 0.0004 (6) | −0.0021 (6) |
C13 | 0.0215 (6) | 0.0177 (6) | 0.0160 (6) | −0.0013 (5) | 0.0029 (5) | −0.0004 (5) |
C14 | 0.0196 (6) | 0.0229 (7) | 0.0126 (6) | 0.0000 (5) | 0.0059 (5) | −0.0015 (5) |
C15 | 0.0232 (7) | 0.0178 (7) | 0.0198 (6) | 0.0012 (5) | 0.0045 (5) | −0.0040 (5) |
C16 | 0.0238 (7) | 0.0239 (7) | 0.0235 (7) | −0.0014 (6) | 0.0028 (6) | −0.0058 (6) |
C17 | 0.0199 (6) | 0.0283 (8) | 0.0197 (7) | 0.0018 (5) | 0.0009 (5) | −0.0020 (6) |
C18 | 0.0229 (6) | 0.0239 (7) | 0.0153 (6) | 0.0018 (5) | 0.0068 (5) | −0.0001 (5) |
C19 | 0.0332 (8) | 0.0283 (9) | 0.0527 (10) | −0.0068 (7) | −0.0115 (8) | −0.0018 (8) |
C20 | 0.0313 (8) | 0.0271 (8) | 0.0244 (7) | 0.0014 (6) | 0.0052 (6) | 0.0053 (6) |
C21 | 0.0192 (6) | 0.0227 (7) | 0.0180 (6) | 0.0015 (5) | 0.0048 (5) | 0.0018 (5) |
C22 | 0.0169 (6) | 0.0230 (7) | 0.0160 (6) | −0.0008 (5) | 0.0024 (5) | −0.0014 (5) |
C23 | 0.0255 (7) | 0.0195 (7) | 0.0238 (7) | 0.0014 (5) | 0.0084 (6) | 0.0003 (6) |
C24 | 0.0278 (7) | 0.0245 (7) | 0.0241 (7) | −0.0009 (6) | 0.0101 (6) | 0.0014 (6) |
C25 | 0.0244 (7) | 0.0266 (7) | 0.0239 (7) | 0.0020 (6) | 0.0113 (6) | −0.0018 (6) |
C26 | 0.0232 (7) | 0.0229 (7) | 0.0183 (6) | 0.0009 (5) | 0.0048 (5) | −0.0025 (6) |
C27 | 0.0504 (10) | 0.0276 (8) | 0.0482 (10) | 0.0014 (7) | 0.0308 (9) | 0.0057 (7) |
C28 | 0.0370 (8) | 0.0240 (8) | 0.0341 (8) | 0.0038 (6) | 0.0158 (7) | 0.0005 (6) |
C29 | 0.0222 (6) | 0.0186 (7) | 0.0161 (6) | 0.0013 (5) | 0.0056 (5) | 0.0007 (5) |
C30 | 0.0229 (6) | 0.0160 (6) | 0.0200 (6) | 0.0002 (5) | 0.0081 (5) | −0.0019 (5) |
C31 | 0.0301 (7) | 0.0187 (7) | 0.0226 (7) | −0.0014 (5) | 0.0073 (6) | −0.0044 (6) |
C32 | 0.0512 (10) | 0.0353 (9) | 0.0255 (8) | −0.0077 (8) | 0.0172 (7) | −0.0105 (7) |
C33 | 0.0475 (9) | 0.0234 (8) | 0.0418 (9) | −0.0019 (7) | 0.0294 (8) | −0.0045 (7) |
C34 | 0.0253 (7) | 0.0215 (7) | 0.0252 (7) | −0.0002 (5) | 0.0119 (6) | −0.0005 (6) |
C35 | 0.0258 (7) | 0.0175 (7) | 0.0227 (7) | 0.0005 (5) | 0.0080 (6) | −0.0011 (5) |
O1W | 0.0275 (5) | 0.0216 (5) | 0.0202 (5) | −0.0052 (4) | 0.0084 (4) | −0.0029 (4) |
Geometric parameters (Å, º) top
O1—C35 | 1.4275 (16) | C15—H15 | 0.9500 |
O1—H1A | 0.874 (9) | C16—C17 | 1.397 (2) |
N1—C14 | 1.3779 (16) | C16—C19 | 1.500 (2) |
N1—C13 | 1.4685 (17) | C17—C18 | 1.3837 (19) |
N1—H1 | 0.885 (9) | C17—H17 | 0.9500 |
N2—C14 | 1.3443 (17) | C18—C20 | 1.5076 (19) |
N2—C18 | 1.3451 (17) | C19—H19A | 0.9800 |
N3—C22 | 1.3705 (17) | C19—H19B | 0.9800 |
N3—C21 | 1.4558 (17) | C19—H19C | 0.9800 |
N3—H3 | 0.889 (9) | C20—H20A | 0.9800 |
N4—C22 | 1.3410 (17) | C20—H20B | 0.9800 |
N4—C26 | 1.3578 (17) | C20—H20C | 0.9800 |
N5—C29 | 1.4787 (16) | C21—H21A | 0.9900 |
N5—C30 | 1.4876 (16) | C21—H21B | 0.9900 |
N5—H5 | 0.896 (9) | C22—C23 | 1.4093 (19) |
C1—C6 | 1.4039 (17) | C23—C24 | 1.3744 (19) |
C1—C2 | 1.4080 (18) | C23—H23 | 0.9500 |
C1—C7 | 1.5243 (17) | C24—C25 | 1.401 (2) |
C2—C3 | 1.4041 (17) | C24—C27 | 1.506 (2) |
C2—C13 | 1.5155 (17) | C25—C26 | 1.377 (2) |
C3—C4 | 1.4067 (18) | C25—H25 | 0.9500 |
C3—C9 | 1.5177 (18) | C26—C28 | 1.5046 (19) |
C4—C5 | 1.4037 (18) | C27—H27A | 0.9800 |
C4—C21 | 1.5219 (17) | C27—H27B | 0.9800 |
C5—C6 | 1.4120 (17) | C27—H27C | 0.9800 |
C5—C11 | 1.5197 (17) | C28—H28A | 0.9800 |
C6—C29 | 1.5172 (18) | C28—H28B | 0.9800 |
C7—C8 | 1.5284 (19) | C28—H28C | 0.9800 |
C7—H7A | 0.9900 | C29—H29A | 0.9900 |
C7—H7B | 0.9900 | C29—H29B | 0.9900 |
C8—H8A | 0.9800 | C30—C35 | 1.5310 (18) |
C8—H8B | 0.9800 | C30—C31 | 1.5548 (18) |
C8—H8C | 0.9800 | C30—C34 | 1.5556 (18) |
C9—C10 | 1.532 (2) | C31—C32 | 1.531 (2) |
C9—H9A | 0.9900 | C31—H31A | 0.9900 |
C9—H9B | 0.9900 | C31—H31B | 0.9900 |
C10—H10A | 0.9800 | C32—C33 | 1.522 (2) |
C10—H10B | 0.9800 | C32—H32A | 0.9900 |
C10—H10C | 0.9800 | C32—H32B | 0.9900 |
C11—C12 | 1.5333 (19) | C33—C34 | 1.525 (2) |
C11—H11A | 0.9900 | C33—H33A | 0.9900 |
C11—H11B | 0.9900 | C33—H33B | 0.9900 |
C12—H12A | 0.9800 | C34—H34A | 0.9900 |
C12—H12B | 0.9800 | C34—H34B | 0.9900 |
C12—H12C | 0.9800 | C35—H35A | 0.9900 |
C13—H13A | 0.9900 | C35—H35B | 0.9900 |
C13—H13B | 0.9900 | O1W—H1W | 0.861 (9) |
C14—C15 | 1.4001 (18) | O1W—H2W | 0.871 (9) |
C15—C16 | 1.3824 (18) | | |
| | | |
C35—O1—H1A | 112.5 (13) | C16—C19—H19B | 109.5 |
C14—N1—C13 | 122.12 (11) | H19A—C19—H19B | 109.5 |
C14—N1—H1 | 112.4 (11) | C16—C19—H19C | 109.5 |
C13—N1—H1 | 114.0 (11) | H19A—C19—H19C | 109.5 |
C14—N2—C18 | 117.94 (11) | H19B—C19—H19C | 109.5 |
C22—N3—C21 | 125.38 (12) | C18—C20—H20A | 109.5 |
C22—N3—H3 | 116.6 (11) | C18—C20—H20B | 109.5 |
C21—N3—H3 | 116.7 (11) | H20A—C20—H20B | 109.5 |
C22—N4—C26 | 116.90 (11) | C18—C20—H20C | 109.5 |
C29—N5—C30 | 118.35 (10) | H20A—C20—H20C | 109.5 |
C29—N5—H5 | 108.8 (10) | H20B—C20—H20C | 109.5 |
C30—N5—H5 | 108.4 (10) | N3—C21—C4 | 109.97 (10) |
C6—C1—C2 | 119.53 (11) | N3—C21—H21A | 109.7 |
C6—C1—C7 | 120.77 (11) | C4—C21—H21A | 109.7 |
C2—C1—C7 | 119.70 (11) | N3—C21—H21B | 109.7 |
C3—C2—C1 | 120.72 (11) | C4—C21—H21B | 109.7 |
C3—C2—C13 | 120.66 (11) | H21A—C21—H21B | 108.2 |
C1—C2—C13 | 118.17 (11) | N4—C22—N3 | 118.97 (12) |
C2—C3—C4 | 119.15 (11) | N4—C22—C23 | 122.97 (12) |
C2—C3—C9 | 120.74 (11) | N3—C22—C23 | 118.03 (12) |
C4—C3—C9 | 120.10 (11) | C24—C23—C22 | 119.43 (13) |
C5—C4—C3 | 120.60 (11) | C24—C23—H23 | 120.3 |
C5—C4—C21 | 120.03 (11) | C22—C23—H23 | 120.3 |
C3—C4—C21 | 119.19 (11) | C23—C24—C25 | 117.79 (13) |
C4—C5—C6 | 119.53 (11) | C23—C24—C27 | 121.36 (13) |
C4—C5—C11 | 120.33 (11) | C25—C24—C27 | 120.85 (13) |
C6—C5—C11 | 120.12 (11) | C26—C25—C24 | 119.63 (12) |
C1—C6—C5 | 120.14 (11) | C26—C25—H25 | 120.2 |
C1—C6—C29 | 117.93 (11) | C24—C25—H25 | 120.2 |
C5—C6—C29 | 121.78 (11) | N4—C26—C25 | 123.26 (12) |
C1—C7—C8 | 111.59 (11) | N4—C26—C28 | 115.73 (12) |
C1—C7—H7A | 109.3 | C25—C26—C28 | 121.01 (12) |
C8—C7—H7A | 109.3 | C24—C27—H27A | 109.5 |
C1—C7—H7B | 109.3 | C24—C27—H27B | 109.5 |
C8—C7—H7B | 109.3 | H27A—C27—H27B | 109.5 |
H7A—C7—H7B | 108.0 | C24—C27—H27C | 109.5 |
C7—C8—H8A | 109.5 | H27A—C27—H27C | 109.5 |
C7—C8—H8B | 109.5 | H27B—C27—H27C | 109.5 |
H8A—C8—H8B | 109.5 | C26—C28—H28A | 109.5 |
C7—C8—H8C | 109.5 | C26—C28—H28B | 109.5 |
H8A—C8—H8C | 109.5 | H28A—C28—H28B | 109.5 |
H8B—C8—H8C | 109.5 | C26—C28—H28C | 109.5 |
C3—C9—C10 | 113.32 (11) | H28A—C28—H28C | 109.5 |
C3—C9—H9A | 108.9 | H28B—C28—H28C | 109.5 |
C10—C9—H9A | 108.9 | N5—C29—C6 | 108.41 (10) |
C3—C9—H9B | 108.9 | N5—C29—H29A | 110.0 |
C10—C9—H9B | 108.9 | C6—C29—H29A | 110.0 |
H9A—C9—H9B | 107.7 | N5—C29—H29B | 110.0 |
C9—C10—H10A | 109.5 | C6—C29—H29B | 110.0 |
C9—C10—H10B | 109.5 | H29A—C29—H29B | 108.4 |
H10A—C10—H10B | 109.5 | N5—C30—C35 | 106.05 (10) |
C9—C10—H10C | 109.5 | N5—C30—C31 | 110.47 (11) |
H10A—C10—H10C | 109.5 | C35—C30—C31 | 109.58 (11) |
H10B—C10—H10C | 109.5 | N5—C30—C34 | 116.39 (11) |
C5—C11—C12 | 113.62 (11) | C35—C30—C34 | 109.43 (11) |
C5—C11—H11A | 108.8 | C31—C30—C34 | 104.86 (10) |
C12—C11—H11A | 108.8 | C32—C31—C30 | 106.29 (11) |
C5—C11—H11B | 108.8 | C32—C31—H31A | 110.5 |
C12—C11—H11B | 108.8 | C30—C31—H31A | 110.5 |
H11A—C11—H11B | 107.7 | C32—C31—H31B | 110.5 |
C11—C12—H12A | 109.5 | C30—C31—H31B | 110.5 |
C11—C12—H12B | 109.5 | H31A—C31—H31B | 108.7 |
H12A—C12—H12B | 109.5 | C33—C32—C31 | 104.00 (12) |
C11—C12—H12C | 109.5 | C33—C32—H32A | 111.0 |
H12A—C12—H12C | 109.5 | C31—C32—H32A | 111.0 |
H12B—C12—H12C | 109.5 | C33—C32—H32B | 111.0 |
N1—C13—C2 | 106.75 (10) | C31—C32—H32B | 111.0 |
N1—C13—H13A | 110.4 | H32A—C32—H32B | 109.0 |
C2—C13—H13A | 110.4 | C32—C33—C34 | 103.01 (12) |
N1—C13—H13B | 110.4 | C32—C33—H33A | 111.2 |
C2—C13—H13B | 110.4 | C34—C33—H33A | 111.2 |
H13A—C13—H13B | 108.6 | C32—C33—H33B | 111.2 |
N2—C14—N1 | 115.60 (11) | C34—C33—H33B | 111.2 |
N2—C14—C15 | 122.67 (12) | H33A—C33—H33B | 109.1 |
N1—C14—C15 | 121.72 (12) | C33—C34—C30 | 104.58 (11) |
C16—C15—C14 | 119.04 (13) | C33—C34—H34A | 110.8 |
C16—C15—H15 | 120.5 | C30—C34—H34A | 110.8 |
C14—C15—H15 | 120.5 | C33—C34—H34B | 110.8 |
C15—C16—C17 | 118.19 (12) | C30—C34—H34B | 110.8 |
C15—C16—C19 | 120.87 (13) | H34A—C34—H34B | 108.9 |
C17—C16—C19 | 120.93 (13) | O1—C35—C30 | 113.25 (11) |
C18—C17—C16 | 119.44 (12) | O1—C35—H35A | 108.9 |
C18—C17—H17 | 120.3 | C30—C35—H35A | 108.9 |
C16—C17—H17 | 120.3 | O1—C35—H35B | 108.9 |
N2—C18—C17 | 122.67 (13) | C30—C35—H35B | 108.9 |
N2—C18—C20 | 115.89 (12) | H35A—C35—H35B | 107.7 |
C17—C18—C20 | 121.45 (12) | H1W—O1W—H2W | 107.2 (18) |
C16—C19—H19A | 109.5 | | |
| | | |
C6—C1—C2—C3 | 3.01 (18) | C15—C16—C17—C18 | −1.2 (2) |
C7—C1—C2—C3 | −176.05 (11) | C19—C16—C17—C18 | 177.68 (14) |
C6—C1—C2—C13 | −169.44 (11) | C14—N2—C18—C17 | 2.26 (18) |
C7—C1—C2—C13 | 11.50 (17) | C14—N2—C18—C20 | −177.50 (11) |
C1—C2—C3—C4 | 1.77 (18) | C16—C17—C18—N2 | −0.6 (2) |
C13—C2—C3—C4 | 174.02 (11) | C16—C17—C18—C20 | 179.14 (13) |
C1—C2—C3—C9 | −176.97 (11) | C22—N3—C21—C4 | −139.10 (13) |
C13—C2—C3—C9 | −4.72 (18) | C5—C4—C21—N3 | −84.62 (14) |
C2—C3—C4—C5 | −5.90 (18) | C3—C4—C21—N3 | 90.57 (14) |
C9—C3—C4—C5 | 172.84 (11) | C26—N4—C22—N3 | −178.80 (11) |
C2—C3—C4—C21 | 178.94 (11) | C26—N4—C22—C23 | −0.68 (18) |
C9—C3—C4—C21 | −2.32 (18) | C21—N3—C22—N4 | −0.42 (19) |
C3—C4—C5—C6 | 5.22 (18) | C21—N3—C22—C23 | −178.64 (12) |
C21—C4—C5—C6 | −179.67 (11) | N4—C22—C23—C24 | −0.8 (2) |
C3—C4—C5—C11 | −173.26 (11) | N3—C22—C23—C24 | 177.36 (12) |
C21—C4—C5—C11 | 1.85 (18) | C22—C23—C24—C25 | 1.3 (2) |
C2—C1—C6—C5 | −3.71 (18) | C22—C23—C24—C27 | −178.42 (14) |
C7—C1—C6—C5 | 175.34 (11) | C23—C24—C25—C26 | −0.4 (2) |
C2—C1—C6—C29 | 171.98 (11) | C27—C24—C25—C26 | 179.31 (14) |
C7—C1—C6—C29 | −8.97 (17) | C22—N4—C26—C25 | 1.63 (19) |
C4—C5—C6—C1 | −0.36 (18) | C22—N4—C26—C28 | −178.68 (12) |
C11—C5—C6—C1 | 178.12 (11) | C24—C25—C26—N4 | −1.1 (2) |
C4—C5—C6—C29 | −175.88 (11) | C24—C25—C26—C28 | 179.23 (13) |
C11—C5—C6—C29 | 2.60 (18) | C30—N5—C29—C6 | 168.54 (10) |
C6—C1—C7—C8 | −93.07 (14) | C1—C6—C29—N5 | −74.81 (14) |
C2—C1—C7—C8 | 85.97 (14) | C5—C6—C29—N5 | 100.80 (13) |
C2—C3—C9—C10 | −88.30 (15) | C29—N5—C30—C35 | −170.13 (10) |
C4—C3—C9—C10 | 92.98 (15) | C29—N5—C30—C31 | 71.21 (14) |
C4—C5—C11—C12 | −94.72 (14) | C29—N5—C30—C34 | −48.19 (15) |
C6—C5—C11—C12 | 86.81 (15) | N5—C30—C31—C32 | −122.98 (12) |
C14—N1—C13—C2 | −148.51 (12) | C35—C30—C31—C32 | 120.53 (13) |
C3—C2—C13—N1 | −95.00 (13) | C34—C30—C31—C32 | 3.17 (15) |
C1—C2—C13—N1 | 77.45 (14) | C30—C31—C32—C33 | −27.13 (16) |
C18—N2—C14—N1 | 177.18 (11) | C31—C32—C33—C34 | 40.92 (15) |
C18—N2—C14—C15 | −2.14 (18) | C32—C33—C34—C30 | −38.95 (15) |
C13—N1—C14—N2 | 154.81 (12) | N5—C30—C34—C33 | 144.32 (12) |
C13—N1—C14—C15 | −25.87 (18) | C35—C30—C34—C33 | −95.53 (13) |
N2—C14—C15—C16 | 0.36 (19) | C31—C30—C34—C33 | 21.93 (14) |
N1—C14—C15—C16 | −178.91 (12) | N5—C30—C35—O1 | 67.44 (13) |
C14—C15—C16—C17 | 1.31 (19) | C31—C30—C35—O1 | −173.32 (11) |
C14—C15—C16—C19 | −177.57 (14) | C34—C30—C35—O1 | −58.86 (14) |
Hydrogen-bond geometry (Å, º) topCg1 and Cg2 are the centroids of the C1–C6
and C14–C18/N2 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H2W···N5 | 0.87 (1) | 1.93 (1) | 2.8018 (14) | 175 (2) |
O1W—H1W···N2i | 0.86 (1) | 2.03 (1) | 2.8780 (15) | 166 (2) |
O1—H1A···O1Wi | 0.87 (1) | 1.83 (1) | 2.6993 (14) | 176 (2) |
N5—H5···O1Wi | 0.90 (1) | 2.52 (1) | 3.3302 (14) | 151 (1) |
N3—H3···O1i | 0.89 (1) | 2.05 (1) | 2.9115 (15) | 162 (2) |
N1—H1···O1Wi | 0.89 (1) | 2.50 (1) | 3.2618 (16) | 145 (1) |
C32—H32B···Cg1ii | 0.99 | 2.69 | 3.666 (2) | 169 |
C25—H25···Cg2iii | 0.95 | 2.84 | 3.728 (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·CH4O | Z = 2 |
Mr = 589.85 | F(000) = 644 |
Triclinic, P1 | Dx = 1.046 Mg m−3 |
a = 12.1169 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.2380 (5) Å | Cell parameters from 9915 reflections |
c = 13.6258 (5) Å | θ = 2.8–30.5° |
α = 68.373 (2)° | µ = 0.07 mm−1 |
β = 79.379 (2)° | T = 100 K |
γ = 67.392 (2)° | Irregular, colourless |
V = 1873.32 (12) Å3 | 0.56 × 0.34 × 0.32 mm |
Data collection top
Bruker X8 APEXII CCD diffractometer | Rint = 0.022 |
phi and ω scans | θmax = 26.4°, θmin = 1.8° |
32191 measured reflections | h = −14→15 |
7654 independent reflections | k = −15→16 |
5160 reflections with I > 2σ(I) | l = 0→17 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.065 | H 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 reflections | Δρmax = 0.64 e Å−3 |
410 parameters | Δρmin = −0.39 e Å−3 |
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 | Uiso*/Ueq | |
O1 | 1.27014 (18) | 0.57360 (19) | 0.78975 (18) | 0.0337 (5) | |
H1A | 1.3308 | 0.5159 | 0.7868 | 0.051* | |
N1 | 0.8131 (3) | 0.6398 (2) | 0.68505 (19) | 0.0298 (6) | |
H1 | 0.848 (3) | 0.588 (3) | 0.750 (3) | 0.030 (8)* | |
N2 | 0.7667 (3) | 0.6725 (3) | 0.5157 (2) | 0.0382 (7) | |
N3 | 0.6133 (2) | 0.73074 (19) | 1.09127 (18) | 0.0208 (5) | |
H3 | 0.656 (3) | 0.667 (3) | 1.081 (2) | 0.023 (8)* | |
N4 | 0.53696 (19) | 0.61277 (18) | 1.23326 (17) | 0.0182 (4) | |
N5 | 1.12190 (19) | 0.67304 (18) | 0.94010 (18) | 0.0190 (4) | |
H5 | 1.110 (3) | 0.628 (3) | 0.910 (3) | 0.027 (8)* | |
C1 | 0.9042 (2) | 0.7808 (2) | 0.78008 (19) | 0.0159 (5) | |
C2 | 0.7918 (2) | 0.7816 (2) | 0.76743 (19) | 0.0179 (5) | |
C3 | 0.6984 (2) | 0.7982 (2) | 0.8449 (2) | 0.0186 (5) | |
C4 | 0.7184 (2) | 0.8192 (2) | 0.93271 (19) | 0.0173 (5) | |
C5 | 0.8303 (2) | 0.8189 (2) | 0.94606 (19) | 0.0164 (5) | |
C6 | 0.9235 (2) | 0.7990 (2) | 0.86997 (19) | 0.0160 (5) | |
C7 | 1.0021 (2) | 0.7657 (2) | 0.6940 (2) | 0.0207 (5) | |
H7A | 0.9917 | 0.7167 | 0.6589 | 0.025* | |
H7B | 1.0809 | 0.7252 | 0.7264 | 0.025* | |
C8 | 1.0008 (3) | 0.8814 (2) | 0.6114 (2) | 0.0287 (6) | |
H8A | 0.9235 | 0.9212 | 0.5781 | 0.043* | |
H8B | 1.0652 | 0.8677 | 0.5575 | 0.043* | |
H8C | 1.0127 | 0.9296 | 0.6456 | 0.043* | |
C9 | 0.5782 (2) | 0.7944 (2) | 0.8331 (2) | 0.0249 (6) | |
H9A | 0.5417 | 0.7656 | 0.9043 | 0.030* | |
H9B | 0.5909 | 0.7389 | 0.7960 | 0.030* | |
C10 | 0.4912 (3) | 0.9125 (3) | 0.7722 (3) | 0.0349 (7) | |
H10A | 0.4798 | 0.9686 | 0.8075 | 0.052* | |
H10B | 0.4141 | 0.9056 | 0.7701 | 0.052* | |
H10C | 0.5241 | 0.9391 | 0.6999 | 0.052* | |
C11 | 0.8503 (2) | 0.8411 (2) | 1.0417 (2) | 0.0195 (5) | |
H11A | 0.9340 | 0.7959 | 1.0622 | 0.023* | |
H11B | 0.7971 | 0.8138 | 1.1016 | 0.023* | |
C12 | 0.8259 (3) | 0.9694 (2) | 1.0213 (2) | 0.0283 (6) | |
H12A | 0.8792 | 0.9967 | 0.9628 | 0.042* | |
H12B | 0.8406 | 0.9791 | 1.0851 | 0.042* | |
H12C | 0.7425 | 1.0144 | 1.0030 | 0.042* | |
C13 | 0.7709 (3) | 0.7627 (2) | 0.6698 (2) | 0.0240 (6) | |
H13A | 0.6844 | 0.7971 | 0.6565 | 0.029* | |
H13B | 0.8140 | 0.8016 | 0.6074 | 0.029* | |
C14 | 0.8157 (3) | 0.5977 (3) | 0.6068 (2) | 0.0301 (7) | |
C15 | 0.8695 (3) | 0.4779 (3) | 0.6252 (3) | 0.0351 (7) | |
H15 | 0.9032 | 0.4270 | 0.6910 | 0.042* | |
C16 | 0.8722 (3) | 0.4360 (4) | 0.5462 (3) | 0.0480 (10) | |
C17 | 0.8216 (4) | 0.5129 (4) | 0.4515 (3) | 0.0548 (12) | |
H17 | 0.8222 | 0.4854 | 0.3960 | 0.066* | |
C18 | 0.7710 (3) | 0.6284 (4) | 0.4385 (3) | 0.0516 (11) | |
C19 | 0.9332 (4) | 0.3088 (4) | 0.5622 (4) | 0.0662 (14) | |
H19A | 0.8931 | 0.2853 | 0.5225 | 0.099* | |
H19B | 0.9289 | 0.2646 | 0.6375 | 0.099* | |
H19C | 1.0172 | 0.2936 | 0.5368 | 0.099* | |
C20 | 0.7149 (5) | 0.7156 (5) | 0.3377 (3) | 0.0755 (16) | |
H20A | 0.6293 | 0.7531 | 0.3520 | 0.113* | |
H20B | 0.7252 | 0.6763 | 0.2863 | 0.113* | |
H20C | 0.7535 | 0.7741 | 0.3089 | 0.113* | |
C21 | 0.6162 (2) | 0.8401 (2) | 1.0146 (2) | 0.0200 (5) | |
H21A | 0.6267 | 0.8879 | 1.0510 | 0.024* | |
H21B | 0.5393 | 0.8828 | 0.9791 | 0.024* | |
C22 | 0.5286 (2) | 0.7214 (2) | 1.17214 (19) | 0.0168 (5) | |
C23 | 0.4398 (2) | 0.8186 (2) | 1.1916 (2) | 0.0183 (5) | |
H23 | 0.4344 | 0.8945 | 1.1460 | 0.022* | |
C24 | 0.3604 (2) | 0.8028 (2) | 1.2778 (2) | 0.0206 (5) | |
C25 | 0.3712 (2) | 0.6901 (2) | 1.3418 (2) | 0.0226 (5) | |
H25 | 0.3185 | 0.6767 | 1.4022 | 0.027* | |
C26 | 0.4592 (2) | 0.5973 (2) | 1.3170 (2) | 0.0211 (5) | |
C27 | 0.2644 (3) | 0.9050 (2) | 1.3014 (2) | 0.0293 (6) | |
H27A | 0.2900 | 0.9726 | 1.2716 | 0.044* | |
H27B | 0.2505 | 0.8873 | 1.3781 | 0.044* | |
H27C | 0.1902 | 0.9218 | 1.2698 | 0.044* | |
C28 | 0.4714 (3) | 0.4746 (2) | 1.3806 (2) | 0.0282 (6) | |
H28A | 0.4429 | 0.4419 | 1.3406 | 0.042* | |
H28B | 0.4236 | 0.4724 | 1.4472 | 0.042* | |
H28C | 0.5556 | 0.4291 | 1.3956 | 0.042* | |
C29 | 1.0471 (2) | 0.7940 (2) | 0.8843 (2) | 0.0191 (5) | |
H29A | 1.0858 | 0.8231 | 0.8144 | 0.023* | |
H29B | 1.0398 | 0.8442 | 0.9257 | 0.023* | |
C30 | 1.2540 (2) | 0.6488 (2) | 0.9314 (2) | 0.0212 (5) | |
C31 | 1.2823 (2) | 0.7329 (2) | 0.9663 (2) | 0.0277 (6) | |
H31A | 1.3654 | 0.7311 | 0.9441 | 0.033* | |
H31B | 1.2264 | 0.8130 | 0.9367 | 0.033* | |
C32 | 1.2660 (3) | 0.6884 (3) | 1.0860 (3) | 0.0313 (7) | |
H32A | 1.1801 | 0.7099 | 1.1090 | 0.038* | |
H32B | 1.3061 | 0.7192 | 1.1194 | 0.038* | |
C33 | 1.3256 (3) | 0.5566 (3) | 1.1131 (2) | 0.0308 (6) | |
H33A | 1.2857 | 0.5159 | 1.1770 | 0.037* | |
H33B | 1.4113 | 0.5318 | 1.1261 | 0.037* | |
C34 | 1.3113 (2) | 0.5300 (2) | 1.0158 (2) | 0.0265 (6) | |
H34A | 1.2590 | 0.4830 | 1.0346 | 0.032* | |
H34B | 1.3901 | 0.4868 | 0.9889 | 0.032* | |
C35 | 1.3038 (2) | 0.6496 (2) | 0.8197 (2) | 0.0270 (6) | |
H35A | 1.2728 | 0.7292 | 0.7694 | 0.032* | |
H35B | 1.3922 | 0.6249 | 0.8170 | 0.032* | |
O1A | 0.95054 (19) | 0.4462 (2) | 0.85754 (17) | 0.0358 (5) | |
H1AA | 0.9330 | 0.4031 | 0.9162 | 0.054* | |
C1A | 1.0583 (3) | 0.4590 (3) | 0.8631 (2) | 0.0296 (6) | |
H1A1 | 1.0627 | 0.5308 | 0.8087 | 0.044* | |
H1A2 | 1.1256 | 0.3929 | 0.8515 | 0.044* | |
H1A3 | 1.0623 | 0.4622 | 0.9331 | 0.044* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0203 (10) | 0.0337 (12) | 0.0483 (13) | 0.0011 (9) | 0.0023 (9) | −0.0275 (11) |
N1 | 0.0507 (16) | 0.0266 (13) | 0.0192 (12) | −0.0167 (12) | −0.0054 (11) | −0.0102 (10) |
N2 | 0.0466 (16) | 0.0630 (19) | 0.0195 (12) | −0.0329 (15) | −0.0007 (11) | −0.0154 (12) |
N3 | 0.0201 (11) | 0.0157 (11) | 0.0223 (11) | −0.0041 (9) | 0.0068 (9) | −0.0074 (9) |
N4 | 0.0167 (10) | 0.0180 (10) | 0.0200 (11) | −0.0060 (8) | 0.0019 (8) | −0.0075 (9) |
N5 | 0.0153 (10) | 0.0168 (10) | 0.0252 (11) | −0.0034 (8) | −0.0012 (8) | −0.0094 (9) |
C1 | 0.0184 (12) | 0.0112 (11) | 0.0143 (11) | −0.0024 (9) | 0.0019 (9) | −0.0041 (9) |
C2 | 0.0222 (13) | 0.0144 (11) | 0.0149 (12) | −0.0045 (10) | −0.0027 (10) | −0.0035 (9) |
C3 | 0.0196 (12) | 0.0133 (11) | 0.0198 (12) | −0.0042 (9) | −0.0008 (10) | −0.0036 (10) |
C4 | 0.0175 (12) | 0.0149 (11) | 0.0170 (12) | −0.0053 (9) | 0.0017 (9) | −0.0039 (9) |
C5 | 0.0186 (12) | 0.0140 (11) | 0.0151 (11) | −0.0034 (9) | 0.0004 (9) | −0.0061 (9) |
C6 | 0.0150 (12) | 0.0119 (11) | 0.0194 (12) | −0.0028 (9) | −0.0002 (9) | −0.0058 (9) |
C7 | 0.0214 (13) | 0.0223 (13) | 0.0177 (12) | −0.0066 (10) | 0.0038 (10) | −0.0090 (10) |
C8 | 0.0338 (16) | 0.0219 (14) | 0.0242 (14) | −0.0081 (12) | 0.0097 (12) | −0.0076 (11) |
C9 | 0.0213 (13) | 0.0315 (15) | 0.0254 (14) | −0.0139 (11) | −0.0010 (11) | −0.0082 (12) |
C10 | 0.0247 (15) | 0.0402 (18) | 0.0346 (17) | −0.0095 (13) | −0.0074 (12) | −0.0057 (14) |
C11 | 0.0220 (13) | 0.0199 (13) | 0.0175 (12) | −0.0054 (10) | 0.0007 (10) | −0.0097 (10) |
C12 | 0.0347 (16) | 0.0196 (13) | 0.0317 (15) | −0.0048 (12) | −0.0030 (12) | −0.0140 (12) |
C13 | 0.0304 (15) | 0.0230 (13) | 0.0194 (13) | −0.0114 (11) | −0.0015 (11) | −0.0056 (11) |
C14 | 0.0360 (16) | 0.0473 (18) | 0.0230 (14) | −0.0286 (14) | 0.0079 (12) | −0.0184 (13) |
C15 | 0.0389 (17) | 0.0447 (18) | 0.0386 (17) | −0.0292 (15) | 0.0183 (14) | −0.0265 (15) |
C16 | 0.046 (2) | 0.077 (3) | 0.056 (2) | −0.045 (2) | 0.0341 (18) | −0.053 (2) |
C17 | 0.060 (2) | 0.110 (4) | 0.044 (2) | −0.065 (3) | 0.0349 (18) | −0.060 (2) |
C18 | 0.051 (2) | 0.110 (4) | 0.0274 (17) | −0.058 (2) | 0.0143 (15) | −0.037 (2) |
C19 | 0.066 (3) | 0.088 (3) | 0.089 (3) | −0.052 (3) | 0.052 (2) | −0.078 (3) |
C20 | 0.083 (3) | 0.142 (5) | 0.030 (2) | −0.066 (3) | 0.001 (2) | −0.033 (3) |
C21 | 0.0188 (12) | 0.0170 (12) | 0.0203 (13) | −0.0051 (10) | 0.0046 (10) | −0.0059 (10) |
C22 | 0.0153 (12) | 0.0199 (12) | 0.0182 (12) | −0.0060 (10) | −0.0002 (9) | −0.0098 (10) |
C23 | 0.0166 (12) | 0.0162 (12) | 0.0192 (12) | −0.0034 (9) | 0.0013 (9) | −0.0061 (10) |
C24 | 0.0185 (12) | 0.0226 (13) | 0.0210 (13) | −0.0063 (10) | 0.0041 (10) | −0.0110 (11) |
C25 | 0.0180 (12) | 0.0250 (14) | 0.0232 (13) | −0.0073 (11) | 0.0057 (10) | −0.0092 (11) |
C26 | 0.0188 (13) | 0.0207 (13) | 0.0228 (13) | −0.0074 (10) | 0.0020 (10) | −0.0069 (11) |
C27 | 0.0268 (14) | 0.0202 (13) | 0.0314 (15) | −0.0023 (11) | 0.0117 (12) | −0.0106 (12) |
C28 | 0.0314 (15) | 0.0211 (14) | 0.0270 (14) | −0.0098 (12) | 0.0087 (12) | −0.0064 (11) |
C29 | 0.0200 (12) | 0.0168 (12) | 0.0214 (13) | −0.0070 (10) | 0.0031 (10) | −0.0085 (10) |
C30 | 0.0147 (12) | 0.0198 (13) | 0.0309 (14) | −0.0070 (10) | 0.0028 (10) | −0.0111 (11) |
C31 | 0.0189 (13) | 0.0237 (14) | 0.0447 (17) | −0.0077 (11) | −0.0020 (12) | −0.0152 (13) |
C32 | 0.0240 (14) | 0.0360 (16) | 0.0426 (18) | −0.0095 (12) | −0.0047 (13) | −0.0219 (14) |
C33 | 0.0241 (14) | 0.0330 (16) | 0.0354 (16) | −0.0110 (12) | −0.0023 (12) | −0.0097 (13) |
C34 | 0.0197 (13) | 0.0242 (14) | 0.0348 (16) | −0.0058 (11) | 0.0008 (11) | −0.0116 (12) |
C35 | 0.0168 (13) | 0.0254 (14) | 0.0356 (16) | −0.0063 (11) | 0.0066 (11) | −0.0114 (12) |
O1A | 0.0292 (11) | 0.0375 (12) | 0.0312 (11) | −0.0152 (9) | −0.0019 (9) | 0.0033 (9) |
C1A | 0.0297 (15) | 0.0257 (14) | 0.0330 (16) | −0.0124 (12) | 0.0041 (12) | −0.0089 (12) |
Geometric parameters (Å, º) top
O1—C35 | 1.423 (4) | C16—C17 | 1.386 (6) |
O1—H1A | 0.8400 | C16—C19 | 1.503 (6) |
N1—C14 | 1.364 (4) | C17—C18 | 1.366 (6) |
N1—C13 | 1.451 (4) | C17—H17 | 0.9500 |
N1—H1 | 0.94 (3) | C18—C20 | 1.501 (6) |
N2—C14 | 1.337 (4) | C19—H19A | 0.9800 |
N2—C18 | 1.363 (4) | C19—H19B | 0.9800 |
N3—C22 | 1.365 (3) | C19—H19C | 0.9800 |
N3—C21 | 1.448 (3) | C20—H20A | 0.9800 |
N3—H3 | 0.85 (3) | C20—H20B | 0.9800 |
N4—C22 | 1.345 (3) | C20—H20C | 0.9800 |
N4—C26 | 1.346 (3) | C21—H21A | 0.9900 |
N5—C29 | 1.485 (3) | C21—H21B | 0.9900 |
N5—C30 | 1.497 (3) | C22—C23 | 1.402 (3) |
N5—H5 | 0.90 (3) | C23—C24 | 1.381 (3) |
C1—C2 | 1.400 (4) | C23—H23 | 0.9500 |
C1—C6 | 1.407 (3) | C24—C25 | 1.391 (4) |
C1—C7 | 1.517 (3) | C24—C27 | 1.503 (3) |
C2—C3 | 1.408 (3) | C25—C26 | 1.388 (4) |
C2—C13 | 1.522 (3) | C25—H25 | 0.9500 |
C3—C4 | 1.404 (4) | C26—C28 | 1.495 (4) |
C3—C9 | 1.517 (4) | C27—H27A | 0.9800 |
C4—C5 | 1.398 (3) | C27—H27B | 0.9800 |
C4—C21 | 1.520 (3) | C27—H27C | 0.9800 |
C5—C6 | 1.401 (3) | C28—H28A | 0.9800 |
C5—C11 | 1.515 (3) | C28—H28B | 0.9800 |
C6—C29 | 1.518 (3) | C28—H28C | 0.9800 |
C7—C8 | 1.526 (4) | C29—H29A | 0.9900 |
C7—H7A | 0.9900 | C29—H29B | 0.9900 |
C7—H7B | 0.9900 | C30—C31 | 1.525 (4) |
C8—H8A | 0.9800 | C30—C35 | 1.527 (4) |
C8—H8B | 0.9800 | C30—C34 | 1.549 (4) |
C8—H8C | 0.9800 | C31—C32 | 1.519 (4) |
C9—C10 | 1.531 (4) | C31—H31A | 0.9900 |
C9—H9A | 0.9900 | C31—H31B | 0.9900 |
C9—H9B | 0.9900 | C32—C33 | 1.536 (4) |
C10—H10A | 0.9800 | C32—H32A | 0.9900 |
C10—H10B | 0.9800 | C32—H32B | 0.9900 |
C10—H10C | 0.9800 | C33—C34 | 1.545 (4) |
C11—C12 | 1.531 (4) | C33—H33A | 0.9900 |
C11—H11A | 0.9900 | C33—H33B | 0.9900 |
C11—H11B | 0.9900 | C34—H34A | 0.9900 |
C12—H12A | 0.9800 | C34—H34B | 0.9900 |
C12—H12B | 0.9800 | C35—H35A | 0.9900 |
C12—H12C | 0.9800 | C35—H35B | 0.9900 |
C13—H13A | 0.9900 | O1A—C1A | 1.399 (4) |
C13—H13B | 0.9900 | O1A—H1AA | 0.8400 |
C14—C15 | 1.406 (5) | C1A—H1A1 | 0.9800 |
C15—C16 | 1.371 (4) | C1A—H1A2 | 0.9800 |
C15—H15 | 0.9500 | C1A—H1A3 | 0.9800 |
| | | |
C35—O1—H1A | 109.5 | H19A—C19—H19C | 109.5 |
C14—N1—C13 | 122.7 (3) | H19B—C19—H19C | 109.5 |
C14—N1—H1 | 119 (2) | C18—C20—H20A | 109.5 |
C13—N1—H1 | 118 (2) | C18—C20—H20B | 109.5 |
C14—N2—C18 | 117.3 (3) | H20A—C20—H20B | 109.5 |
C22—N3—C21 | 123.8 (2) | C18—C20—H20C | 109.5 |
C22—N3—H3 | 114 (2) | H20A—C20—H20C | 109.5 |
C21—N3—H3 | 121 (2) | H20B—C20—H20C | 109.5 |
C22—N4—C26 | 118.8 (2) | N3—C21—C4 | 110.2 (2) |
C29—N5—C30 | 115.6 (2) | N3—C21—H21A | 109.6 |
C29—N5—H5 | 106 (2) | C4—C21—H21A | 109.6 |
C30—N5—H5 | 106 (2) | N3—C21—H21B | 109.6 |
C2—C1—C6 | 119.8 (2) | C4—C21—H21B | 109.6 |
C2—C1—C7 | 119.4 (2) | H21A—C21—H21B | 108.1 |
C6—C1—C7 | 120.7 (2) | N4—C22—N3 | 115.6 (2) |
C1—C2—C3 | 120.5 (2) | N4—C22—C23 | 122.0 (2) |
C1—C2—C13 | 119.7 (2) | N3—C22—C23 | 122.3 (2) |
C3—C2—C13 | 119.8 (2) | C24—C23—C22 | 119.2 (2) |
C4—C3—C2 | 118.8 (2) | C24—C23—H23 | 120.4 |
C4—C3—C9 | 120.7 (2) | C22—C23—H23 | 120.4 |
C2—C3—C9 | 120.5 (2) | C23—C24—C25 | 118.4 (2) |
C5—C4—C3 | 121.1 (2) | C23—C24—C27 | 120.6 (2) |
C5—C4—C21 | 120.5 (2) | C25—C24—C27 | 121.0 (2) |
C3—C4—C21 | 118.4 (2) | C26—C25—C24 | 119.8 (2) |
C4—C5—C6 | 119.6 (2) | C26—C25—H25 | 120.1 |
C4—C5—C11 | 120.3 (2) | C24—C25—H25 | 120.1 |
C6—C5—C11 | 120.1 (2) | N4—C26—C25 | 121.9 (2) |
C5—C6—C1 | 120.1 (2) | N4—C26—C28 | 116.3 (2) |
C5—C6—C29 | 120.7 (2) | C25—C26—C28 | 121.8 (2) |
C1—C6—C29 | 119.2 (2) | C24—C27—H27A | 109.5 |
C1—C7—C8 | 112.1 (2) | C24—C27—H27B | 109.5 |
C1—C7—H7A | 109.2 | H27A—C27—H27B | 109.5 |
C8—C7—H7A | 109.2 | C24—C27—H27C | 109.5 |
C1—C7—H7B | 109.2 | H27A—C27—H27C | 109.5 |
C8—C7—H7B | 109.2 | H27B—C27—H27C | 109.5 |
H7A—C7—H7B | 107.9 | C26—C28—H28A | 109.5 |
C7—C8—H8A | 109.5 | C26—C28—H28B | 109.5 |
C7—C8—H8B | 109.5 | H28A—C28—H28B | 109.5 |
H8A—C8—H8B | 109.5 | C26—C28—H28C | 109.5 |
C7—C8—H8C | 109.5 | H28A—C28—H28C | 109.5 |
H8A—C8—H8C | 109.5 | H28B—C28—H28C | 109.5 |
H8B—C8—H8C | 109.5 | N5—C29—C6 | 110.1 (2) |
C3—C9—C10 | 113.1 (2) | N5—C29—H29A | 109.6 |
C3—C9—H9A | 109.0 | C6—C29—H29A | 109.6 |
C10—C9—H9A | 109.0 | N5—C29—H29B | 109.6 |
C3—C9—H9B | 109.0 | C6—C29—H29B | 109.6 |
C10—C9—H9B | 109.0 | H29A—C29—H29B | 108.1 |
H9A—C9—H9B | 107.8 | N5—C30—C31 | 110.6 (2) |
C9—C10—H10A | 109.5 | N5—C30—C35 | 110.3 (2) |
C9—C10—H10B | 109.5 | C31—C30—C35 | 113.0 (2) |
H10A—C10—H10B | 109.5 | N5—C30—C34 | 107.1 (2) |
C9—C10—H10C | 109.5 | C31—C30—C34 | 103.3 (2) |
H10A—C10—H10C | 109.5 | C35—C30—C34 | 112.1 (2) |
H10B—C10—H10C | 109.5 | C32—C31—C30 | 103.5 (2) |
C5—C11—C12 | 112.6 (2) | C32—C31—H31A | 111.1 |
C5—C11—H11A | 109.1 | C30—C31—H31A | 111.1 |
C12—C11—H11A | 109.1 | C32—C31—H31B | 111.1 |
C5—C11—H11B | 109.1 | C30—C31—H31B | 111.1 |
C12—C11—H11B | 109.1 | H31A—C31—H31B | 109.0 |
H11A—C11—H11B | 107.8 | C31—C32—C33 | 103.2 (2) |
C11—C12—H12A | 109.5 | C31—C32—H32A | 111.1 |
C11—C12—H12B | 109.5 | C33—C32—H32A | 111.1 |
H12A—C12—H12B | 109.5 | C31—C32—H32B | 111.1 |
C11—C12—H12C | 109.5 | C33—C32—H32B | 111.1 |
H12A—C12—H12C | 109.5 | H32A—C32—H32B | 109.1 |
H12B—C12—H12C | 109.5 | C32—C33—C34 | 105.5 (2) |
N1—C13—C2 | 109.9 (2) | C32—C33—H33A | 110.6 |
N1—C13—H13A | 109.7 | C34—C33—H33A | 110.6 |
C2—C13—H13A | 109.7 | C32—C33—H33B | 110.6 |
N1—C13—H13B | 109.7 | C34—C33—H33B | 110.6 |
C2—C13—H13B | 109.7 | H33A—C33—H33B | 108.8 |
H13A—C13—H13B | 108.2 | C33—C34—C30 | 106.2 (2) |
N2—C14—N1 | 118.4 (3) | C33—C34—H34A | 110.5 |
N2—C14—C15 | 122.8 (3) | C30—C34—H34A | 110.5 |
N1—C14—C15 | 118.8 (3) | C33—C34—H34B | 110.5 |
C16—C15—C14 | 118.6 (4) | C30—C34—H34B | 110.5 |
C16—C15—H15 | 120.7 | H34A—C34—H34B | 108.7 |
C14—C15—H15 | 120.7 | O1—C35—C30 | 110.5 (2) |
C15—C16—C17 | 119.0 (4) | O1—C35—H35A | 109.5 |
C15—C16—C19 | 119.8 (4) | C30—C35—H35A | 109.5 |
C17—C16—C19 | 121.2 (3) | O1—C35—H35B | 109.5 |
C18—C17—C16 | 119.6 (3) | C30—C35—H35B | 109.5 |
C18—C17—H17 | 120.2 | H35A—C35—H35B | 108.1 |
C16—C17—H17 | 120.2 | C1A—O1A—H1AA | 109.5 |
N2—C18—C17 | 122.7 (4) | O1A—C1A—H1A1 | 109.5 |
N2—C18—C20 | 115.5 (4) | O1A—C1A—H1A2 | 109.5 |
C17—C18—C20 | 121.8 (4) | H1A1—C1A—H1A2 | 109.5 |
C16—C19—H19A | 109.5 | O1A—C1A—H1A3 | 109.5 |
C16—C19—H19B | 109.5 | H1A1—C1A—H1A3 | 109.5 |
H19A—C19—H19B | 109.5 | H1A2—C1A—H1A3 | 109.5 |
C16—C19—H19C | 109.5 | | |
| | | |
C6—C1—C2—C3 | −1.2 (4) | C15—C16—C17—C18 | 0.4 (5) |
C7—C1—C2—C3 | −178.5 (2) | C19—C16—C17—C18 | −177.6 (3) |
C6—C1—C2—C13 | 179.5 (2) | C14—N2—C18—C17 | 0.6 (5) |
C7—C1—C2—C13 | 2.3 (3) | C14—N2—C18—C20 | 180.0 (3) |
C1—C2—C3—C4 | 2.8 (4) | C16—C17—C18—N2 | −0.6 (5) |
C13—C2—C3—C4 | −177.9 (2) | C16—C17—C18—C20 | −180.0 (3) |
C1—C2—C3—C9 | −177.7 (2) | C22—N3—C21—C4 | −177.5 (2) |
C13—C2—C3—C9 | 1.6 (4) | C5—C4—C21—N3 | −93.1 (3) |
C2—C3—C4—C5 | −2.7 (4) | C3—C4—C21—N3 | 85.7 (3) |
C9—C3—C4—C5 | 177.8 (2) | C26—N4—C22—N3 | 177.4 (2) |
C2—C3—C4—C21 | 178.5 (2) | C26—N4—C22—C23 | −1.5 (4) |
C9—C3—C4—C21 | −1.0 (3) | C21—N3—C22—N4 | 177.4 (2) |
C3—C4—C5—C6 | 1.0 (4) | C21—N3—C22—C23 | −3.7 (4) |
C21—C4—C5—C6 | 179.7 (2) | N4—C22—C23—C24 | 1.8 (4) |
C3—C4—C5—C11 | −179.6 (2) | N3—C22—C23—C24 | −177.0 (2) |
C21—C4—C5—C11 | −0.9 (3) | C22—C23—C24—C25 | −0.5 (4) |
C4—C5—C6—C1 | 0.7 (4) | C22—C23—C24—C27 | 179.7 (3) |
C11—C5—C6—C1 | −178.7 (2) | C23—C24—C25—C26 | −0.9 (4) |
C4—C5—C6—C29 | −177.8 (2) | C27—C24—C25—C26 | 178.8 (3) |
C11—C5—C6—C29 | 2.8 (3) | C22—N4—C26—C25 | 0.0 (4) |
C2—C1—C6—C5 | −0.6 (3) | C22—N4—C26—C28 | 178.8 (2) |
C7—C1—C6—C5 | 176.6 (2) | C24—C25—C26—N4 | 1.3 (4) |
C2—C1—C6—C29 | 178.0 (2) | C24—C25—C26—C28 | −177.5 (3) |
C7—C1—C6—C29 | −4.8 (3) | C30—N5—C29—C6 | 162.4 (2) |
C2—C1—C7—C8 | 89.8 (3) | C5—C6—C29—N5 | 90.9 (3) |
C6—C1—C7—C8 | −87.4 (3) | C1—C6—C29—N5 | −87.6 (3) |
C4—C3—C9—C10 | 90.5 (3) | C29—N5—C30—C31 | 54.1 (3) |
C2—C3—C9—C10 | −89.0 (3) | C29—N5—C30—C35 | −71.7 (3) |
C4—C5—C11—C12 | −91.6 (3) | C29—N5—C30—C34 | 166.1 (2) |
C6—C5—C11—C12 | 87.8 (3) | N5—C30—C31—C32 | 75.2 (3) |
C14—N1—C13—C2 | −173.9 (3) | C35—C30—C31—C32 | −160.5 (2) |
C1—C2—C13—N1 | 83.0 (3) | C34—C30—C31—C32 | −39.2 (3) |
C3—C2—C13—N1 | −96.2 (3) | C30—C31—C32—C33 | 42.6 (3) |
C18—N2—C14—N1 | 179.7 (3) | C31—C32—C33—C34 | −29.1 (3) |
C18—N2—C14—C15 | −0.4 (4) | C32—C33—C34—C30 | 5.1 (3) |
C13—N1—C14—N2 | −6.6 (4) | N5—C30—C34—C33 | −96.1 (2) |
C13—N1—C14—C15 | 173.5 (3) | C31—C30—C34—C33 | 20.7 (3) |
N2—C14—C15—C16 | 0.3 (4) | C35—C30—C34—C33 | 142.8 (2) |
N1—C14—C15—C16 | −179.8 (3) | N5—C30—C35—O1 | −52.9 (3) |
C14—C15—C16—C17 | −0.3 (4) | C31—C30—C35—O1 | −177.4 (2) |
C14—C15—C16—C19 | 177.8 (3) | C34—C30—C35—O1 | 66.3 (3) |
Hydrogen-bond geometry (Å, º) topCg1 and Cg3 are the centroids of the C1–C6
and C22–C26/N4 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1A | 0.94 (3) | 2.01 (3) | 2.930 (3) | 162 (2) |
C15—H15···O1A | 0.95 | 2.56 | 3.318 (3) | 137 |
N5—H5···O1 | 0.90 (3) | 2.36 (3) | 2.823 (3) | 112 (2) |
O1—H1A···N4i | 0.84 | 1.90 | 2.741 (3) | 174 |
O1A—H1AA···N5i | 0.84 | 1.97 | 2.798 (3) | 170 |
C27—H27A···Cg1ii | 0.98 | 2.67 | 3.541 (3) | 148 |
C32—H32B···Cg3iii | 0.98 | 2.69 | 3.614 (3) | 156 |
Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+1, −y+2, −z+2; (iii) x+1, y, z. |