


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314619012094/hb4316sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2414314619012094/hb4316Isup2.hkl |
![]() | MDL mol file https://doi.org/10.1107/S2414314619012094/hb4316Isup3.mol |
![]() | MDL mol file https://doi.org/10.1107/S2414314619012094/hb4316Isup4.mol |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314619012094/hb4316Isup5.cml |
CCDC reference: 1950911
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.049
- wR factor = 0.129
- Data-to-parameter ratio = 21.5
checkCIF/PLATON results
No syntax errors found
Alert level C CRYSC01_ALERT_1_C The word below has not been recognised as a standard identifier. off PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.4 Note
Alert level G PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd. # 2 Note C7 H9 N O2 PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 5 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 19 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 3 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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
Data collection: SAINT (Bruker, 2014); cell refinement: APEX2 (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015b); program(s) used to refine structure: SHELXL (Sheldrick, 2015a); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
C7H9NO2·C7H11NO | Z = 4 |
Mr = 264.32 | F(000) = 568 |
Triclinic, P1 | Dx = 1.260 Mg m−3 |
a = 10.2673 (17) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.885 (2) Å | Cell parameters from 4195 reflections |
c = 12.839 (2) Å | θ = 2.2–30.4° |
α = 90.601 (3)° | µ = 0.09 mm−1 |
β = 108.694 (2)° | T = 100 K |
γ = 108.797 (2)° | Block, off-white |
V = 1393.6 (4) Å3 | 0.5 × 0.4 × 0.4 mm |
Bruker APEXII CCD diffractometer | 5738 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.042 |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | θmax = 29.6°, θmin = 1.7° |
Tmin = 0.638, Tmax = 0.746 | h = −14→14 |
22087 measured reflections | k = −16→16 |
7807 independent reflections | l = −17→17 |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.129 | w = 1/[σ2(Fo2) + (0.0602P)2 + 0.2427P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
7807 reflections | Δρmax = 0.47 e Å−3 |
363 parameters | Δρmin = −0.31 e Å−3 |
0 restraints |
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. |
Refinement. 1. Fixed Uiso At 1.2 times of: All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C4(H4A,H4B), C5(H5A,H5B), C19(H19A,H19B), C12(H12A,H12B), C11(H11A,H11B), C26(H26A,H26B) 2.b Idealised Me refined as rotating group: C6(H6A,H6B,H6C), C21(H21A,H21B,H21C), C28(H28A,H28B,H28C), C14(H14A,H14B, H14C), C7(H7A,H7B,H7C), C13(H13A,H13B,H13C), C20(H20A,H20B,H20C), C27(H27A, H27B,H27C) The coordinates of the four hydrogen atoms (H1–H4) engaged in hydrogen bonds were refined while all others were treated with a riding model. |
x | y | z | Uiso*/Ueq | ||
O2 | 0.21235 (10) | 0.36055 (8) | 0.67113 (8) | 0.0189 (2) | |
O6 | 0.01203 (11) | 0.43139 (9) | 0.40166 (8) | 0.0204 (2) | |
O4 | 0.75738 (11) | 0.53952 (9) | 1.01712 (8) | 0.0227 (2) | |
O1 | 0.56722 (10) | 0.62186 (9) | 0.75879 (8) | 0.0200 (2) | |
N1 | 0.38644 (12) | 0.55072 (10) | 0.58794 (9) | 0.0167 (2) | |
H1 | 0.3252 (18) | 0.4919 (15) | 0.6090 (13) | 0.020* | |
N3 | 0.83545 (13) | 0.71001 (10) | 0.93659 (10) | 0.0184 (2) | |
H3 | 0.7591 (19) | 0.6936 (14) | 0.8759 (14) | 0.022* | |
N2 | 0.41748 (13) | 0.39669 (10) | 0.82662 (9) | 0.0173 (2) | |
H2 | 0.4672 (18) | 0.4676 (15) | 0.8144 (13) | 0.021* | |
N4 | −0.07317 (13) | 0.28418 (11) | 0.50433 (10) | 0.0179 (2) | |
H4 | 0.0032 (19) | 0.3029 (14) | 0.5626 (14) | 0.021* | |
C17 | 1.05941 (14) | 0.79960 (12) | 1.07610 (10) | 0.0150 (3) | |
C22 | −0.08165 (14) | 0.34340 (12) | 0.41122 (11) | 0.0155 (3) | |
C15 | 0.84850 (15) | 0.63481 (12) | 1.01803 (11) | 0.0161 (3) | |
C16 | 0.99545 (14) | 0.69420 (11) | 1.10621 (10) | 0.0148 (3) | |
C4 | 0.35382 (14) | 0.58429 (12) | 0.47670 (10) | 0.0160 (3) | |
H4A | 0.261465 | 0.601924 | 0.452921 | 0.019* | |
H4B | 0.346318 | 0.520259 | 0.422851 | 0.019* | |
C25 | −0.19971 (14) | 0.18630 (12) | 0.48532 (11) | 0.0165 (3) | |
C8 | 0.28393 (14) | 0.33068 (11) | 0.75769 (10) | 0.0145 (3) | |
C2 | 0.57626 (14) | 0.71910 (11) | 0.59323 (11) | 0.0143 (3) | |
C9 | 0.23720 (14) | 0.21533 (11) | 0.80256 (10) | 0.0145 (3) | |
C1 | 0.51327 (14) | 0.62710 (11) | 0.65760 (11) | 0.0146 (3) | |
C3 | 0.48329 (14) | 0.69498 (12) | 0.48829 (11) | 0.0160 (3) | |
C18 | 0.95907 (15) | 0.81199 (12) | 0.96574 (11) | 0.0158 (3) | |
C23 | −0.22806 (14) | 0.27622 (12) | 0.32497 (11) | 0.0158 (3) | |
C5 | 0.72351 (14) | 0.81347 (12) | 0.64460 (11) | 0.0166 (3) | |
H5A | 0.735531 | 0.842900 | 0.720704 | 0.020* | |
H5B | 0.731364 | 0.881951 | 0.600889 | 0.020* | |
C10 | 0.34397 (15) | 0.21846 (12) | 0.89684 (11) | 0.0181 (3) | |
C24 | −0.29647 (14) | 0.18262 (12) | 0.36832 (11) | 0.0160 (3) | |
C19 | 1.04928 (15) | 0.63491 (12) | 1.20459 (11) | 0.0179 (3) | |
H19A | 0.967578 | 0.594456 | 1.231284 | 0.022* | |
H19B | 1.126080 | 0.696203 | 1.265012 | 0.022* | |
C12 | 0.09622 (15) | 0.11766 (12) | 0.74122 (11) | 0.0166 (3) | |
H12A | 0.016830 | 0.151805 | 0.716328 | 0.020* | |
H12B | 0.071684 | 0.058196 | 0.791571 | 0.020* | |
C11 | 0.46781 (15) | 0.33592 (12) | 0.92045 (11) | 0.0200 (3) | |
H11A | 0.483313 | 0.381371 | 0.991025 | 0.024* | |
H11B | 0.559978 | 0.323772 | 0.923819 | 0.024* | |
C6 | 0.84446 (15) | 0.76321 (13) | 0.64858 (13) | 0.0217 (3) | |
H6A | 0.837583 | 0.740555 | 0.572885 | 0.033* | |
H6B | 0.833063 | 0.692535 | 0.688108 | 0.033* | |
H6C | 0.940213 | 0.824333 | 0.687316 | 0.033* | |
C26 | −0.27140 (16) | 0.31362 (13) | 0.21204 (11) | 0.0205 (3) | |
H26A | −0.232183 | 0.402105 | 0.217677 | 0.025* | |
H26B | −0.379499 | 0.287546 | 0.180019 | 0.025* | |
C21 | 1.20247 (15) | 0.89522 (12) | 1.13460 (12) | 0.0212 (3) | |
H21A | 1.239559 | 0.881228 | 1.211939 | 0.032* | |
H21B | 1.189481 | 0.973418 | 1.132249 | 0.032* | |
H21C | 1.272630 | 0.894004 | 1.098176 | 0.032* | |
C28 | −0.44102 (15) | 0.08562 (13) | 0.31799 (12) | 0.0227 (3) | |
H28A | −0.426890 | 0.014964 | 0.290058 | 0.034* | |
H28B | −0.503616 | 0.113395 | 0.256625 | 0.034* | |
H28C | −0.487704 | 0.064646 | 0.374165 | 0.034* | |
C14 | 0.34989 (17) | 0.12475 (13) | 0.97320 (12) | 0.0267 (3) | |
H14A | 0.365796 | 0.158789 | 1.047956 | 0.040* | |
H14B | 0.430505 | 0.096871 | 0.974960 | 0.040* | |
H14C | 0.257235 | 0.057154 | 0.946743 | 0.040* | |
C7 | 0.49576 (17) | 0.76137 (14) | 0.39212 (12) | 0.0251 (3) | |
H7A | 0.490389 | 0.706904 | 0.331831 | 0.038* | |
H7B | 0.589613 | 0.827669 | 0.414715 | 0.038* | |
H7C | 0.415465 | 0.793187 | 0.366574 | 0.038* | |
C13 | 0.10590 (18) | 0.05544 (14) | 0.64105 (12) | 0.0279 (3) | |
H13A | 0.138738 | 0.115245 | 0.594465 | 0.042* | |
H13B | 0.009283 | −0.002138 | 0.598084 | 0.042* | |
H13C | 0.175899 | 0.013167 | 0.666147 | 0.042* | |
C20 | 1.11168 (19) | 0.54321 (14) | 1.17583 (12) | 0.0281 (3) | |
H20A | 1.037566 | 0.485350 | 1.112993 | 0.042* | |
H20B | 1.139336 | 0.501084 | 1.239994 | 0.042* | |
H20C | 1.198210 | 0.584309 | 1.156019 | 0.042* | |
C27 | −0.21402 (19) | 0.25974 (17) | 0.13569 (13) | 0.0326 (4) | |
H27A | −0.238918 | 0.289768 | 0.063739 | 0.049* | |
H27B | −0.258790 | 0.172231 | 0.125321 | 0.049* | |
H27C | −0.107419 | 0.282525 | 0.168859 | 0.049* | |
O3 | 0.98077 (11) | 0.89459 (9) | 0.91156 (8) | 0.0225 (2) | |
O5 | −0.22727 (11) | 0.11830 (9) | 0.55131 (8) | 0.0247 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.0159 (5) | 0.0195 (5) | 0.0151 (5) | 0.0016 (4) | 0.0015 (4) | 0.0072 (4) |
O6 | 0.0182 (5) | 0.0173 (5) | 0.0219 (5) | 0.0000 (4) | 0.0078 (4) | 0.0008 (4) |
O4 | 0.0206 (5) | 0.0181 (5) | 0.0217 (5) | −0.0031 (4) | 0.0070 (4) | 0.0010 (4) |
O1 | 0.0163 (5) | 0.0203 (5) | 0.0155 (5) | 0.0006 (4) | 0.0005 (4) | 0.0057 (4) |
N1 | 0.0146 (5) | 0.0142 (5) | 0.0148 (5) | −0.0004 (4) | 0.0019 (4) | 0.0046 (4) |
N3 | 0.0154 (6) | 0.0178 (6) | 0.0132 (5) | 0.0001 (5) | −0.0008 (5) | 0.0016 (4) |
N2 | 0.0161 (6) | 0.0133 (5) | 0.0152 (5) | −0.0011 (5) | 0.0018 (4) | 0.0050 (4) |
N4 | 0.0130 (5) | 0.0202 (6) | 0.0131 (5) | 0.0005 (5) | 0.0000 (4) | 0.0009 (4) |
C17 | 0.0151 (6) | 0.0147 (6) | 0.0118 (6) | 0.0023 (5) | 0.0030 (5) | −0.0002 (5) |
C22 | 0.0156 (6) | 0.0157 (6) | 0.0155 (6) | 0.0053 (5) | 0.0056 (5) | −0.0001 (5) |
C15 | 0.0166 (6) | 0.0165 (6) | 0.0130 (6) | 0.0023 (5) | 0.0056 (5) | 0.0006 (5) |
C16 | 0.0157 (6) | 0.0146 (6) | 0.0117 (6) | 0.0030 (5) | 0.0038 (5) | −0.0002 (5) |
C4 | 0.0142 (6) | 0.0169 (6) | 0.0128 (6) | 0.0029 (5) | 0.0019 (5) | 0.0022 (5) |
C25 | 0.0138 (6) | 0.0158 (6) | 0.0178 (6) | 0.0043 (5) | 0.0038 (5) | 0.0007 (5) |
C8 | 0.0150 (6) | 0.0137 (6) | 0.0124 (6) | 0.0018 (5) | 0.0048 (5) | 0.0021 (5) |
C2 | 0.0127 (6) | 0.0117 (6) | 0.0179 (6) | 0.0034 (5) | 0.0052 (5) | 0.0037 (5) |
C9 | 0.0156 (6) | 0.0113 (6) | 0.0130 (6) | 0.0003 (5) | 0.0044 (5) | 0.0007 (5) |
C1 | 0.0129 (6) | 0.0127 (6) | 0.0169 (6) | 0.0039 (5) | 0.0037 (5) | 0.0037 (5) |
C3 | 0.0148 (6) | 0.0158 (6) | 0.0177 (6) | 0.0049 (5) | 0.0065 (5) | 0.0045 (5) |
C18 | 0.0151 (6) | 0.0161 (6) | 0.0134 (6) | 0.0034 (5) | 0.0031 (5) | 0.0004 (5) |
C23 | 0.0132 (6) | 0.0149 (6) | 0.0171 (6) | 0.0049 (5) | 0.0022 (5) | −0.0012 (5) |
C5 | 0.0136 (6) | 0.0117 (6) | 0.0198 (7) | 0.0005 (5) | 0.0032 (5) | 0.0031 (5) |
C10 | 0.0179 (7) | 0.0144 (6) | 0.0158 (6) | 0.0006 (5) | 0.0025 (5) | 0.0032 (5) |
C24 | 0.0134 (6) | 0.0143 (6) | 0.0182 (6) | 0.0051 (5) | 0.0024 (5) | −0.0001 (5) |
C19 | 0.0213 (7) | 0.0182 (7) | 0.0116 (6) | 0.0042 (5) | 0.0048 (5) | 0.0042 (5) |
C12 | 0.0157 (6) | 0.0153 (6) | 0.0133 (6) | −0.0003 (5) | 0.0034 (5) | 0.0030 (5) |
C11 | 0.0173 (7) | 0.0168 (7) | 0.0169 (7) | 0.0002 (5) | −0.0003 (5) | 0.0051 (5) |
C6 | 0.0156 (7) | 0.0205 (7) | 0.0268 (7) | 0.0044 (6) | 0.0062 (6) | 0.0049 (6) |
C26 | 0.0186 (7) | 0.0218 (7) | 0.0179 (7) | 0.0061 (6) | 0.0027 (5) | 0.0043 (5) |
C21 | 0.0181 (7) | 0.0175 (7) | 0.0185 (7) | −0.0013 (5) | 0.0014 (5) | 0.0030 (5) |
C28 | 0.0170 (7) | 0.0171 (7) | 0.0256 (7) | 0.0021 (5) | 0.0002 (6) | 0.0015 (6) |
C14 | 0.0234 (8) | 0.0197 (7) | 0.0240 (8) | 0.0009 (6) | −0.0026 (6) | 0.0101 (6) |
C7 | 0.0218 (7) | 0.0309 (8) | 0.0195 (7) | 0.0049 (6) | 0.0070 (6) | 0.0109 (6) |
C13 | 0.0292 (8) | 0.0215 (7) | 0.0223 (7) | −0.0047 (6) | 0.0086 (6) | −0.0056 (6) |
C20 | 0.0371 (9) | 0.0300 (8) | 0.0190 (7) | 0.0177 (7) | 0.0059 (7) | 0.0050 (6) |
C27 | 0.0367 (9) | 0.0478 (10) | 0.0173 (7) | 0.0218 (8) | 0.0071 (7) | 0.0050 (7) |
O3 | 0.0255 (5) | 0.0181 (5) | 0.0179 (5) | 0.0032 (4) | 0.0036 (4) | 0.0060 (4) |
O5 | 0.0225 (5) | 0.0241 (5) | 0.0230 (5) | 0.0039 (4) | 0.0061 (4) | 0.0090 (4) |
O2—C8 | 1.2467 (15) | C5—C6 | 1.530 (2) |
O6—C22 | 1.2100 (16) | C10—C11 | 1.5026 (19) |
O4—C15 | 1.2115 (16) | C10—C14 | 1.4945 (18) |
O1—C1 | 1.2495 (15) | C24—C28 | 1.4887 (19) |
N1—H1 | 0.887 (16) | C19—H19A | 0.9900 |
N1—C4 | 1.4500 (16) | C19—H19B | 0.9900 |
N1—C1 | 1.3395 (17) | C19—C20 | 1.526 (2) |
N3—H3 | 0.875 (17) | C12—H12A | 0.9900 |
N3—C15 | 1.3846 (17) | C12—H12B | 0.9900 |
N3—C18 | 1.3838 (17) | C12—C13 | 1.523 (2) |
N2—H2 | 0.879 (16) | C11—H11A | 0.9900 |
N2—C8 | 1.3391 (17) | C11—H11B | 0.9900 |
N2—C11 | 1.4491 (17) | C6—H6A | 0.9800 |
N4—H4 | 0.856 (17) | C6—H6B | 0.9800 |
N4—C22 | 1.3865 (17) | C6—H6C | 0.9800 |
N4—C25 | 1.3848 (17) | C26—H26A | 0.9900 |
C17—C16 | 1.3389 (18) | C26—H26B | 0.9900 |
C17—C18 | 1.5023 (18) | C26—C27 | 1.523 (2) |
C17—C21 | 1.4874 (18) | C21—H21A | 0.9800 |
C22—C23 | 1.5047 (18) | C21—H21B | 0.9800 |
C15—C16 | 1.5028 (18) | C21—H21C | 0.9800 |
C16—C19 | 1.4899 (18) | C28—H28A | 0.9800 |
C4—H4A | 0.9900 | C28—H28B | 0.9800 |
C4—H4B | 0.9900 | C28—H28C | 0.9800 |
C4—C3 | 1.5040 (18) | C14—H14A | 0.9800 |
C25—C24 | 1.5031 (18) | C14—H14B | 0.9800 |
C25—O5 | 1.2132 (16) | C14—H14C | 0.9800 |
C8—C9 | 1.4871 (17) | C7—H7A | 0.9800 |
C2—C1 | 1.4842 (17) | C7—H7B | 0.9800 |
C2—C3 | 1.3415 (18) | C7—H7C | 0.9800 |
C2—C5 | 1.4936 (18) | C13—H13A | 0.9800 |
C9—C10 | 1.3380 (19) | C13—H13B | 0.9800 |
C9—C12 | 1.4934 (18) | C13—H13C | 0.9800 |
C3—C7 | 1.4900 (18) | C20—H20A | 0.9800 |
C18—O3 | 1.2124 (16) | C20—H20B | 0.9800 |
C23—C24 | 1.3419 (18) | C20—H20C | 0.9800 |
C23—C26 | 1.4918 (18) | C27—H27A | 0.9800 |
C5—H5A | 0.9900 | C27—H27B | 0.9800 |
C5—H5B | 0.9900 | C27—H27C | 0.9800 |
C4—N1—H1 | 124.0 (10) | H19A—C19—H19B | 108.0 |
C1—N1—H1 | 123.9 (10) | C20—C19—H19A | 109.4 |
C1—N1—C4 | 111.72 (11) | C20—C19—H19B | 109.4 |
C15—N3—H3 | 123.6 (11) | C9—C12—H12A | 109.4 |
C18—N3—H3 | 126.2 (11) | C9—C12—H12B | 109.4 |
C18—N3—C15 | 110.15 (11) | C9—C12—C13 | 111.30 (11) |
C8—N2—H2 | 122.8 (10) | H12A—C12—H12B | 108.0 |
C8—N2—C11 | 111.70 (11) | C13—C12—H12A | 109.4 |
C11—N2—H2 | 125.5 (10) | C13—C12—H12B | 109.4 |
C22—N4—H4 | 123.8 (11) | N2—C11—C10 | 102.71 (11) |
C25—N4—H4 | 125.6 (11) | N2—C11—H11A | 111.2 |
C25—N4—C22 | 110.40 (11) | N2—C11—H11B | 111.2 |
C16—C17—C18 | 108.26 (11) | C10—C11—H11A | 111.2 |
C16—C17—C21 | 130.11 (12) | C10—C11—H11B | 111.2 |
C21—C17—C18 | 121.63 (11) | H11A—C11—H11B | 109.1 |
O6—C22—N4 | 126.14 (12) | C5—C6—H6A | 109.5 |
O6—C22—C23 | 127.07 (12) | C5—C6—H6B | 109.5 |
N4—C22—C23 | 106.79 (11) | C5—C6—H6C | 109.5 |
O4—C15—N3 | 125.76 (13) | H6A—C6—H6B | 109.5 |
O4—C15—C16 | 127.26 (12) | H6A—C6—H6C | 109.5 |
N3—C15—C16 | 106.98 (11) | H6B—C6—H6C | 109.5 |
C17—C16—C15 | 107.82 (11) | C23—C26—H26A | 109.4 |
C17—C16—C19 | 130.63 (12) | C23—C26—H26B | 109.4 |
C19—C16—C15 | 121.53 (11) | C23—C26—C27 | 111.36 (12) |
N1—C4—H4A | 111.2 | H26A—C26—H26B | 108.0 |
N1—C4—H4B | 111.2 | C27—C26—H26A | 109.4 |
N1—C4—C3 | 102.76 (10) | C27—C26—H26B | 109.4 |
H4A—C4—H4B | 109.1 | C17—C21—H21A | 109.5 |
C3—C4—H4A | 111.2 | C17—C21—H21B | 109.5 |
C3—C4—H4B | 111.2 | C17—C21—H21C | 109.5 |
N4—C25—C24 | 106.64 (11) | H21A—C21—H21B | 109.5 |
O5—C25—N4 | 126.34 (13) | H21A—C21—H21C | 109.5 |
O5—C25—C24 | 127.01 (12) | H21B—C21—H21C | 109.5 |
O2—C8—N2 | 125.99 (12) | C24—C28—H28A | 109.5 |
O2—C8—C9 | 126.30 (12) | C24—C28—H28B | 109.5 |
N2—C8—C9 | 107.71 (11) | C24—C28—H28C | 109.5 |
C1—C2—C5 | 121.51 (11) | H28A—C28—H28B | 109.5 |
C3—C2—C1 | 108.08 (11) | H28A—C28—H28C | 109.5 |
C3—C2—C5 | 130.31 (12) | H28B—C28—H28C | 109.5 |
C8—C9—C12 | 121.34 (11) | C10—C14—H14A | 109.5 |
C10—C9—C8 | 107.89 (11) | C10—C14—H14B | 109.5 |
C10—C9—C12 | 130.69 (12) | C10—C14—H14C | 109.5 |
O1—C1—N1 | 125.75 (12) | H14A—C14—H14B | 109.5 |
O1—C1—C2 | 126.53 (12) | H14A—C14—H14C | 109.5 |
N1—C1—C2 | 107.71 (11) | H14B—C14—H14C | 109.5 |
C2—C3—C4 | 109.72 (11) | C3—C7—H7A | 109.5 |
C2—C3—C7 | 128.87 (13) | C3—C7—H7B | 109.5 |
C7—C3—C4 | 121.41 (12) | C3—C7—H7C | 109.5 |
N3—C18—C17 | 106.77 (11) | H7A—C7—H7B | 109.5 |
O3—C18—N3 | 125.96 (12) | H7A—C7—H7C | 109.5 |
O3—C18—C17 | 127.27 (12) | H7B—C7—H7C | 109.5 |
C24—C23—C22 | 107.84 (11) | C12—C13—H13A | 109.5 |
C24—C23—C26 | 131.04 (12) | C12—C13—H13B | 109.5 |
C26—C23—C22 | 121.03 (12) | C12—C13—H13C | 109.5 |
C2—C5—H5A | 109.6 | H13A—C13—H13B | 109.5 |
C2—C5—H5B | 109.6 | H13A—C13—H13C | 109.5 |
C2—C5—C6 | 110.49 (11) | H13B—C13—H13C | 109.5 |
H5A—C5—H5B | 108.1 | C19—C20—H20A | 109.5 |
C6—C5—H5A | 109.6 | C19—C20—H20B | 109.5 |
C6—C5—H5B | 109.6 | C19—C20—H20C | 109.5 |
C9—C10—C11 | 109.98 (11) | H20A—C20—H20B | 109.5 |
C9—C10—C14 | 128.69 (13) | H20A—C20—H20C | 109.5 |
C14—C10—C11 | 121.33 (12) | H20B—C20—H20C | 109.5 |
C23—C24—C25 | 108.31 (11) | C26—C27—H27A | 109.5 |
C23—C24—C28 | 130.25 (12) | C26—C27—H27B | 109.5 |
C28—C24—C25 | 121.43 (12) | C26—C27—H27C | 109.5 |
C16—C19—H19A | 109.4 | H27A—C27—H27B | 109.5 |
C16—C19—H19B | 109.4 | H27A—C27—H27C | 109.5 |
C16—C19—C20 | 110.95 (11) | H27B—C27—H27C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.89 (2) | 1.97 (2) | 2.8487 (15) | 173 (2) |
N2—H2···O1 | 0.88 (2) | 2.05 (2) | 2.9222 (15) | 171 (2) |
N3—H3···O1 | 0.88 (2) | 1.97 (2) | 2.8202 (15) | 165 (2) |
N4—H4···O2 | 0.86 (2) | 2.03 (2) | 2.8677 (15) | 165 (2) |