In the title compound, C
21H
21NO
4, the non-fused benzene ring makes angles of 16.0 (1) and 5.6 (2)° with the coumarin ring and the methoxycarbonyl group, respectively. Intermolecular π–π, C—H
π and C—H
O interactions are observed in the crystal structure.
Supporting information
CCDC reference: 620678
Key indicators
- Single-crystal X-ray study
- T = 123 K
- Mean (C-C) = 0.005 Å
- R factor = 0.046
- wR factor = 0.135
- Data-to-parameter ratio = 9.5
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.884 0.997
Tmin(prime) and Tmax expected: 0.988 0.997
RR(prime) = 0.894
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.89
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT432_ALERT_2_C Short Inter X...Y Contact C5 .. C15 .. 3.19 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H17 .. C4 .. 2.86 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H20 .. C16 .. 2.88 Ang.
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 27.48
From the CIF: _reflns_number_total 2249
Count of symmetry unique reflns 2282
Completeness (_total/calc) 98.55%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Version 1.3; Macrae
et al., 2006); software used to prepare material for publication: CrystalStructure.
Methyl 4-(7-diethylamino-2-oxo-2
H-1-benzopyran-3-yl)benzoate
top
Crystal data top
C21H21NO4 | F(000) = 744.00 |
Mr = 351.40 | Dx = 1.358 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 3599 reflections |
a = 6.332 (2) Å | θ = 3.2–27.5° |
b = 12.103 (4) Å | µ = 0.09 mm−1 |
c = 22.424 (8) Å | T = 123 K |
V = 1718.5 (10) Å3 | Platelet, yellow |
Z = 4 | 0.12 × 0.12 × 0.03 mm |
Data collection top
Rigaku Saturn diffractometer | 1207 reflections with F2 > 2σ(F2) |
Detector resolution: 7.31 pixels mm-1 | Rint = 0.072 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (Jacobson, 1998) | h = −7→7 |
Tmin = 0.884, Tmax = 0.997 | k = −15→15 |
14109 measured reflections | l = −29→29 |
2249 independent reflections | |
Refinement top
Refinement on F2 | w = 1/[0.7250σ(Fo2)]/(4Fo2) |
R[F2 > 2σ(F2)] = 0.046 | (Δ/σ)max < 0.001 |
wR(F2) = 0.135 | Δρmax = 0.34 e Å−3 |
S = 1.01 | Δρmin = −0.41 e Å−3 |
2249 reflections | Extinction correction: Larson (1970), equation 22 |
236 parameters | Extinction coefficient: 111 (33) |
H-atom parameters constrained | |
Special details top
Refinement. Refinement using all reflections. The weighted R-factor (wR) and
goodness of fit (S) are based on F2. R-factor (gt) are
based on F. The threshold expression of F2 > 2.0
σ(F2) is used only for calculating R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.2611 (4) | 0.2128 (2) | 0.71275 (12) | 0.0248 (7) | |
O2 | 0.5600 (4) | 0.2832 (2) | 0.74415 (12) | 0.0319 (8) | |
O3 | 1.2575 (4) | −0.0490 (2) | 0.94975 (14) | 0.0439 (9) | |
O4 | 1.2975 (4) | 0.1353 (2) | 0.95221 (12) | 0.0265 (7) | |
N1 | −0.3790 (5) | 0.0798 (2) | 0.62716 (14) | 0.0256 (9) | |
C1 | 0.4415 (5) | 0.2053 (3) | 0.74844 (18) | 0.0228 (10) | |
C2 | 0.4671 (5) | 0.1063 (3) | 0.78468 (17) | 0.0192 (9) | |
C3 | 0.3194 (5) | 0.0250 (3) | 0.77919 (16) | 0.0202 (9) | |
C4 | 0.1453 (5) | 0.0317 (3) | 0.73990 (16) | 0.0192 (9) | |
C5 | −0.0040 (5) | −0.0515 (3) | 0.73050 (16) | 0.0233 (10) | |
C6 | −0.1715 (5) | −0.0381 (3) | 0.69271 (16) | 0.0236 (10) | |
C7 | −0.2020 (5) | 0.0629 (3) | 0.66156 (17) | 0.0212 (9) | |
C8 | −0.0486 (5) | 0.1458 (3) | 0.66855 (17) | 0.0232 (10) | |
C9 | 0.1161 (5) | 0.1290 (3) | 0.70697 (17) | 0.0203 (9) | |
C10 | 0.6523 (5) | 0.0944 (3) | 0.82442 (16) | 0.0208 (9) | |
C11 | 0.7795 (6) | 0.1833 (3) | 0.84176 (17) | 0.0250 (10) | |
C12 | 0.9556 (6) | 0.1684 (3) | 0.87821 (17) | 0.0242 (10) | |
C13 | 1.0081 (5) | 0.0636 (3) | 0.89839 (16) | 0.0215 (9) | |
C14 | 0.8834 (6) | −0.0255 (3) | 0.88184 (17) | 0.0252 (10) | |
C15 | 0.7093 (5) | −0.0103 (3) | 0.84555 (16) | 0.0233 (9) | |
C16 | 1.1968 (6) | 0.0417 (3) | 0.93539 (17) | 0.0259 (10) | |
C17 | 1.4837 (5) | 0.1179 (3) | 0.98836 (18) | 0.0314 (11) | |
C18 | −0.4021 (6) | 0.1798 (3) | 0.59127 (18) | 0.0303 (11) | |
C19 | −0.2763 (8) | 0.1774 (4) | 0.53361 (19) | 0.0431 (13) | |
C20 | −0.5304 (5) | −0.0096 (3) | 0.61685 (17) | 0.0272 (10) | |
C21 | −0.4579 (6) | −0.0970 (3) | 0.57260 (17) | 0.0300 (11) | |
H1 | 0.3335 | −0.0393 | 0.8031 | 0.024* | |
H2 | 0.0116 | −0.1198 | 0.7510 | 0.028* | |
H3 | −0.2687 | −0.0970 | 0.6872 | 0.028* | |
H4 | −0.0599 | 0.2130 | 0.6469 | 0.028* | |
H5 | 0.7458 | 0.2556 | 0.8283 | 0.030* | |
H6 | 1.0396 | 0.2301 | 0.8892 | 0.029* | |
H7 | 0.9184 | −0.0976 | 0.8953 | 0.030* | |
H8 | 0.6262 | −0.0724 | 0.8346 | 0.028* | |
H9 | 1.5217 | 0.1857 | 1.0069 | 0.038* | |
H10 | 1.4540 | 0.0642 | 1.0181 | 0.038* | |
H11 | 1.5972 | 0.0929 | 0.9641 | 0.038* | |
H12 | −0.5471 | 0.1890 | 0.5816 | 0.036* | |
H13 | −0.3558 | 0.2409 | 0.6144 | 0.036* | |
H14 | −0.1396 | 0.2071 | 0.5406 | 0.052* | |
H15 | −0.3465 | 0.2203 | 0.5042 | 0.052* | |
H16 | −0.2637 | 0.1033 | 0.5201 | 0.052* | |
H17 | −0.5563 | −0.0451 | 0.6539 | 0.033* | |
H18 | −0.6580 | 0.0217 | 0.6024 | 0.033* | |
H19 | −0.5694 | −0.1477 | 0.5651 | 0.036* | |
H20 | −0.4181 | −0.0621 | 0.5364 | 0.036* | |
H21 | −0.3401 | −0.1356 | 0.5886 | 0.036* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0228 (13) | 0.0182 (14) | 0.0335 (15) | 0.0003 (12) | −0.0022 (12) | 0.0018 (12) |
O2 | 0.0290 (16) | 0.0197 (15) | 0.0470 (19) | −0.0040 (14) | −0.0062 (15) | 0.0054 (14) |
O3 | 0.0392 (17) | 0.0280 (18) | 0.065 (2) | 0.0012 (16) | −0.0204 (17) | 0.0036 (17) |
O4 | 0.0234 (13) | 0.0272 (16) | 0.0288 (15) | −0.0021 (12) | −0.0073 (12) | 0.0005 (13) |
N1 | 0.0262 (16) | 0.0224 (19) | 0.0282 (18) | −0.0004 (16) | −0.0043 (14) | 0.0008 (16) |
C1 | 0.0171 (19) | 0.020 (2) | 0.032 (2) | 0.0019 (18) | −0.0036 (19) | −0.0006 (19) |
C2 | 0.0176 (16) | 0.0155 (19) | 0.0245 (19) | 0.0018 (16) | 0.0051 (16) | −0.0004 (17) |
C3 | 0.0232 (18) | 0.018 (2) | 0.0189 (18) | 0.0020 (16) | 0.0061 (16) | −0.0001 (16) |
C4 | 0.0224 (18) | 0.016 (2) | 0.0193 (18) | 0.0031 (17) | 0.0004 (15) | −0.0019 (17) |
C5 | 0.0284 (19) | 0.021 (2) | 0.0207 (18) | 0.0016 (19) | 0.0033 (17) | −0.0020 (17) |
C6 | 0.026 (2) | 0.022 (2) | 0.0232 (19) | −0.0032 (18) | 0.0031 (16) | −0.0034 (18) |
C7 | 0.0206 (17) | 0.022 (2) | 0.0209 (18) | −0.0013 (18) | −0.0005 (16) | −0.0036 (17) |
C8 | 0.0251 (19) | 0.020 (2) | 0.025 (2) | 0.0009 (18) | 0.0001 (17) | 0.0007 (17) |
C9 | 0.0205 (17) | 0.0141 (19) | 0.026 (2) | −0.0026 (16) | 0.0032 (16) | −0.0042 (17) |
C10 | 0.0217 (18) | 0.019 (2) | 0.0212 (19) | 0.0047 (18) | 0.0027 (15) | −0.0020 (17) |
C11 | 0.031 (2) | 0.018 (2) | 0.026 (2) | 0.0036 (19) | −0.0001 (18) | 0.0002 (18) |
C12 | 0.028 (2) | 0.021 (2) | 0.0239 (19) | 0.0007 (19) | 0.0002 (17) | −0.0019 (18) |
C13 | 0.0202 (17) | 0.023 (2) | 0.0210 (18) | 0.0010 (17) | 0.0008 (15) | −0.0017 (17) |
C14 | 0.030 (2) | 0.020 (2) | 0.025 (2) | 0.0038 (18) | −0.0003 (17) | 0.0033 (18) |
C15 | 0.0249 (19) | 0.021 (2) | 0.0244 (19) | −0.0020 (19) | 0.0006 (17) | −0.0014 (17) |
C16 | 0.030 (2) | 0.023 (2) | 0.025 (2) | −0.002 (2) | 0.0013 (18) | −0.0008 (18) |
C17 | 0.0256 (19) | 0.041 (2) | 0.028 (2) | −0.002 (2) | −0.0057 (18) | −0.002 (2) |
C18 | 0.032 (2) | 0.027 (2) | 0.033 (2) | 0.000 (2) | −0.0065 (19) | 0.003 (2) |
C19 | 0.061 (3) | 0.030 (2) | 0.038 (2) | −0.002 (2) | 0.004 (2) | 0.003 (2) |
C20 | 0.0245 (19) | 0.032 (2) | 0.0252 (19) | −0.003 (2) | −0.0027 (17) | −0.0027 (19) |
C21 | 0.034 (2) | 0.031 (2) | 0.025 (2) | −0.001 (2) | −0.0040 (18) | −0.0063 (19) |
Geometric parameters (Å, º) top
O1—C1 | 1.398 (4) | C14—C15 | 1.382 (5) |
O1—C9 | 1.375 (4) | C18—C19 | 1.519 (6) |
O2—C1 | 1.209 (4) | C20—C21 | 1.521 (5) |
O3—C16 | 1.207 (5) | C3—H1 | 0.950 |
O4—C16 | 1.353 (5) | C5—H2 | 0.950 |
O4—C17 | 1.446 (4) | C6—H3 | 0.950 |
N1—C7 | 1.376 (4) | C8—H4 | 0.950 |
N1—C18 | 1.462 (5) | C11—H5 | 0.950 |
N1—C20 | 1.464 (5) | C12—H6 | 0.950 |
C1—C2 | 1.457 (5) | C14—H7 | 0.950 |
C2—C3 | 1.363 (5) | C15—H8 | 0.950 |
C2—C10 | 1.480 (5) | C17—H9 | 0.950 |
C3—C4 | 1.413 (4) | C17—H10 | 0.950 |
C4—C5 | 1.397 (5) | C17—H11 | 0.950 |
C4—C9 | 1.402 (5) | C18—H12 | 0.950 |
C5—C6 | 1.367 (5) | C18—H13 | 0.950 |
C6—C7 | 1.421 (5) | C19—H14 | 0.950 |
C7—C8 | 1.405 (5) | C19—H15 | 0.950 |
C8—C9 | 1.368 (5) | C19—H16 | 0.950 |
C10—C11 | 1.399 (5) | C20—H17 | 0.950 |
C10—C15 | 1.400 (5) | C20—H18 | 0.950 |
C11—C12 | 1.395 (5) | C21—H19 | 0.950 |
C12—C13 | 1.386 (5) | C21—H20 | 0.950 |
C13—C14 | 1.388 (5) | C21—H21 | 0.950 |
C13—C16 | 1.479 (5) | | |
| | | |
O1···N1i | 3.387 (4) | H3···H6iv | 3.069 |
O1···C5ii | 3.522 (4) | H3···H8vi | 3.385 |
O1···C18i | 3.482 (4) | H4···O2vi | 3.357 |
O2···C3iii | 3.070 (4) | H4···C14iii | 3.417 |
O2···C4iii | 3.558 (4) | H4···H2ii | 3.072 |
O2···C5iii | 3.497 (4) | H4···H7iii | 2.636 |
O2···C6ii | 3.569 (4) | H4···H12i | 3.574 |
O2···C7i | 3.579 (4) | H4···H18i | 3.582 |
O2···C8i | 3.432 (4) | H5···C5iii | 3.140 |
O3···C18iv | 3.529 (5) | H5···C20ii | 3.383 |
O3···C19iv | 3.335 (5) | H5···C21ii | 3.383 |
O4···C21iii | 3.441 (5) | H5···H2iii | 2.791 |
O4···C21v | 3.482 (4) | H5···H3ii | 3.525 |
N1···O1vi | 3.387 (4) | H5···H17ii | 2.724 |
N1···C1vi | 3.316 (5) | H5···H19ii | 2.887 |
C1···N1i | 3.316 (5) | H5···H21ii | 3.437 |
C1···C7i | 3.444 (5) | H6···C6iii | 3.456 |
C2···C6i | 3.542 (5) | H6···C17 | 3.323 |
C2···C7i | 3.506 (5) | H6···C21iii | 3.482 |
C3···O2iv | 3.070 (4) | H6···H3iii | 3.069 |
C3···C13vi | 3.354 (5) | H6···H9xi | 2.545 |
C3···C16vi | 3.593 (5) | H6···H10xi | 3.287 |
C4···O2iv | 3.558 (4) | H6···H19ii | 3.478 |
C4···C20i | 3.476 (5) | H6···H21iii | 2.551 |
C5···O1vii | 3.522 (4) | H7···O1iv | 3.525 |
C5···O2iv | 3.497 (4) | H7···C8iv | 3.517 |
C5···C10vi | 3.506 (5) | H7···C19v | 3.370 |
C5···C14vi | 3.482 (5) | H7···H1i | 3.418 |
C5···C15vi | 3.194 (5) | H7···H2i | 3.301 |
C6···O2vii | 3.569 (4) | H7···H4iv | 2.636 |
C6···C2vi | 3.542 (5) | H7···H11vi | 3.441 |
C6···C10vi | 3.541 (5) | H7···H12vii | 3.531 |
C6···C15vi | 3.526 (5) | H7···H13iv | 3.397 |
C7···O2vi | 3.579 (4) | H7···H14iv | 3.101 |
C7···C1vi | 3.444 (5) | H7···H15v | 2.894 |
C7···C2vi | 3.506 (5) | H7···H16v | 2.964 |
C8···O2vi | 3.432 (4) | H8···O1iv | 2.897 |
C9···C20i | 3.451 (5) | H8···O2iv | 2.750 |
C10···C5i | 3.506 (5) | H8···O3vi | 3.493 |
C10···C6i | 3.541 (5) | H8···C1iv | 3.300 |
C13···C3i | 3.354 (5) | H8···C5i | 3.316 |
C14···C5i | 3.482 (5) | H8···C6i | 3.454 |
C15···C5i | 3.194 (5) | H8···H2i | 3.130 |
C15···C6i | 3.526 (5) | H8···H3i | 3.385 |
C16···C3i | 3.593 (5) | H8···H11vi | 3.533 |
C16···C21v | 3.493 (5) | H8···H12vii | 3.483 |
C17···C21viii | 3.556 (5) | H8···H13vii | 3.057 |
C18···O1vi | 3.482 (4) | H9···O4xii | 2.931 |
C18···O3iii | 3.529 (5) | H9···C12xii | 3.152 |
C19···O3iii | 3.335 (5) | H9···C21iii | 3.203 |
C20···C4vi | 3.476 (5) | H9···C21viii | 3.309 |
C20···C9vi | 3.451 (5) | H9···H6xii | 2.545 |
C21···O4iv | 3.441 (5) | H9···H9xi | 3.542 |
C21···O4ix | 3.482 (4) | H9···H9xii | 3.542 |
C21···C16ix | 3.493 (5) | H9···H19iii | 2.601 |
C21···C17x | 3.556 (5) | H9···H19v | 3.181 |
O1···H2ii | 2.784 | H9···H20iii | 3.270 |
O1···H3ii | 3.215 | H9···H20viii | 2.995 |
O1···H7iii | 3.525 | H9···H21iii | 3.254 |
O1···H8iii | 2.897 | H9···H21viii | 2.791 |
O1···H12i | 3.196 | H10···C19viii | 3.583 |
O1···H13i | 3.295 | H10···C20v | 3.540 |
O1···H17i | 3.581 | H10···C21v | 3.394 |
O1···H18i | 3.426 | H10···C21viii | 3.440 |
O2···H1iii | 2.488 | H10···H6xii | 3.287 |
O2···H2iii | 2.958 | H10···H14viii | 3.524 |
O2···H3ii | 2.807 | H10···H16viii | 2.821 |
O2···H4i | 3.357 | H10···H18v | 2.858 |
O2···H8iii | 2.750 | H10···H19v | 2.839 |
O2···H13i | 3.001 | H10···H20v | 3.418 |
O2···H17ii | 3.089 | H10···H20viii | 2.967 |
O3···H1i | 3.325 | H10···H21viii | 3.037 |
O3···H8i | 3.493 | H11···C10i | 3.153 |
O3···H13iv | 2.987 | H11···C11i | 3.172 |
O3···H14iv | 3.053 | H11···C12i | 3.114 |
O3···H15iv | 3.030 | H11···C13i | 3.011 |
O3···H15v | 3.544 | H11···C14i | 2.957 |
O3···H16v | 3.562 | H11···C15i | 3.023 |
O3···H18v | 3.495 | H11···C21viii | 3.336 |
O3···H20v | 3.193 | H11···H7i | 3.441 |
O4···H9xi | 2.931 | H11···H8i | 3.533 |
O4···H19iii | 3.165 | H11···H16viii | 2.885 |
O4···H19v | 2.919 | H11···H19iii | 3.212 |
O4···H20v | 3.181 | H11···H20viii | 2.625 |
O4···H21iii | 2.933 | H11···H21viii | 3.228 |
C1···H1iii | 3.594 | H12···O1vi | 3.196 |
C1···H2ii | 3.566 | H12···C19xiii | 3.375 |
C1···H3ii | 3.001 | H12···H4vi | 3.574 |
C1···H8iii | 3.300 | H12···H7ii | 3.531 |
C1···H13i | 3.296 | H12···H8ii | 3.483 |
C2···H17i | 3.461 | H12···H14xiii | 3.070 |
C3···H17i | 3.038 | H12···H15xiii | 2.915 |
C4···H17i | 2.855 | H13···O1vi | 3.295 |
C4···H18i | 3.328 | H13···O2vi | 3.001 |
C5···H5iv | 3.140 | H13···O3iii | 2.987 |
C5···H8vi | 3.316 | H13···C1vi | 3.296 |
C5···H17i | 3.315 | H13···H1ii | 3.242 |
C6···H6iv | 3.456 | H13···H7iii | 3.397 |
C6···H8vi | 3.454 | H13···H8ii | 3.057 |
C8···H2ii | 3.371 | H14···O3iii | 3.053 |
C8···H7iii | 3.517 | H14···C18xiv | 3.588 |
C8···H18i | 3.252 | H14···C19xiv | 3.165 |
C9···H2ii | 3.286 | H14···H7iii | 3.101 |
C9···H17i | 3.187 | H14···H10x | 3.524 |
C9···H18i | 3.038 | H14···H12xiv | 3.070 |
C10···H11vi | 3.153 | H14···H15xiv | 2.286 |
C11···H2iii | 3.428 | H14···H16xiv | 3.575 |
C11···H11vi | 3.172 | H15···O3iii | 3.030 |
C11···H17ii | 3.579 | H15···O3ix | 3.544 |
C11···H19ii | 3.212 | H15···C19xiii | 3.108 |
C12···H9xi | 3.152 | H15···H7ix | 2.894 |
C12···H11vi | 3.114 | H15···H12xiv | 2.915 |
C12···H19ii | 3.543 | H15···H14xiii | 2.286 |
C12···H21iii | 3.480 | H15···H15xiii | 3.252 |
C13···H1i | 3.219 | H15···H15xiv | 3.252 |
C13···H11vi | 3.011 | H15···H16xiii | 3.440 |
C13···H20v | 3.146 | H16···O3ix | 3.562 |
C14···H1i | 3.356 | H16···C14ix | 3.327 |
C14···H2i | 3.252 | H16···C17x | 3.289 |
C14···H4iv | 3.417 | H16···H7ix | 2.964 |
C14···H11vi | 2.957 | H16···H10x | 2.821 |
C14···H16v | 3.327 | H16···H11x | 2.885 |
C15···H2i | 3.149 | H16···H14xiii | 3.575 |
C15···H11vi | 3.023 | H16···H15xiv | 3.440 |
C16···H1i | 3.242 | H17···O1vi | 3.581 |
C16···H19v | 3.280 | H17···O2vii | 3.089 |
C16···H20v | 2.882 | H17···C2vi | 3.461 |
C17···H6xii | 3.323 | H17···C3vi | 3.038 |
C17···H16viii | 3.289 | H17···C4vi | 2.855 |
C17···H19iii | 3.127 | H17···C5vi | 3.315 |
C17···H19v | 3.158 | H17···C9vi | 3.187 |
C17···H20viii | 3.030 | H17···C11vii | 3.579 |
C17···H21iii | 3.565 | H17···H1vi | 3.418 |
C17···H21viii | 3.192 | H17···H5vii | 2.724 |
C18···H14xiii | 3.588 | H18···O1vi | 3.426 |
C19···H7ix | 3.370 | H18···O3ix | 3.495 |
C19···H10x | 3.583 | H18···C4vi | 3.328 |
C19···H12xiv | 3.375 | H18···C8vi | 3.252 |
C19···H14xiii | 3.165 | H18···C9vi | 3.038 |
C19···H15xiv | 3.108 | H18···H4vi | 3.582 |
C20···H5vii | 3.383 | H18···H10ix | 2.858 |
C20···H10ix | 3.540 | H19···O4iv | 3.165 |
C21···H5vii | 3.383 | H19···O4ix | 2.919 |
C21···H6iv | 3.482 | H19···C11vii | 3.212 |
C21···H9iv | 3.203 | H19···C12vii | 3.543 |
C21···H9x | 3.309 | H19···C16ix | 3.280 |
C21···H10ix | 3.394 | H19···C17iv | 3.127 |
C21···H10x | 3.440 | H19···C17ix | 3.158 |
C21···H11x | 3.336 | H19···H5vii | 2.887 |
H1···O2iv | 2.488 | H19···H6vii | 3.478 |
H1···O3vi | 3.325 | H19···H9iv | 2.601 |
H1···C1iv | 3.594 | H19···H9ix | 3.181 |
H1···C13vi | 3.219 | H19···H10ix | 2.839 |
H1···C14vi | 3.356 | H19···H11iv | 3.212 |
H1···C16vi | 3.242 | H20···O3ix | 3.193 |
H1···H7vi | 3.418 | H20···O4ix | 3.181 |
H1···H13vii | 3.242 | H20···C13ix | 3.146 |
H1···H17i | 3.418 | H20···C16ix | 2.882 |
H2···O1vii | 2.784 | H20···C17x | 3.030 |
H2···O2iv | 2.958 | H20···H9iv | 3.270 |
H2···C1vii | 3.566 | H20···H9x | 2.995 |
H2···C8vii | 3.371 | H20···H10ix | 3.418 |
H2···C9vii | 3.286 | H20···H10x | 2.967 |
H2···C11iv | 3.428 | H20···H11x | 2.625 |
H2···C14vi | 3.252 | H21···O4iv | 2.933 |
H2···C15vi | 3.149 | H21···C12iv | 3.480 |
H2···H4vii | 3.072 | H21···C17iv | 3.565 |
H2···H5iv | 2.791 | H21···C17x | 3.192 |
H2···H7vi | 3.301 | H21···H5vii | 3.437 |
H2···H8vi | 3.130 | H21···H6iv | 2.551 |
H3···O1vii | 3.215 | H21···H9iv | 3.254 |
H3···O2vii | 2.807 | H21···H9x | 2.791 |
H3···C1vii | 3.001 | H21···H10x | 3.037 |
H3···H5vii | 3.525 | H21···H11x | 3.228 |
| | | |
C1—O1—C9 | 123.5 (3) | C6—C5—H2 | 118.9 |
C16—O4—C17 | 114.8 (3) | C5—C6—H3 | 119.6 |
C7—N1—C18 | 120.9 (3) | C7—C6—H3 | 119.6 |
C7—N1—C20 | 120.8 (3) | C7—C8—H4 | 120.2 |
C18—N1—C20 | 117.4 (3) | C9—C8—H4 | 120.4 |
O1—C1—O2 | 114.3 (3) | C10—C11—H5 | 119.4 |
O1—C1—C2 | 117.6 (3) | C12—C11—H5 | 119.1 |
O2—C1—C2 | 128.1 (3) | C11—C12—H6 | 119.9 |
C1—C2—C3 | 117.9 (3) | C13—C12—H6 | 120.0 |
C1—C2—C10 | 120.2 (3) | C13—C14—H7 | 119.8 |
C3—C2—C10 | 121.9 (3) | C15—C14—H7 | 119.7 |
C2—C3—C4 | 123.4 (3) | C10—C15—H8 | 119.0 |
C3—C4—C5 | 125.5 (3) | C14—C15—H8 | 119.2 |
C3—C4—C9 | 118.6 (3) | O4—C17—H9 | 109.1 |
C5—C4—C9 | 115.9 (3) | O4—C17—H10 | 109.3 |
C4—C5—C6 | 122.2 (3) | O4—C17—H11 | 110.0 |
C5—C6—C7 | 120.8 (3) | H9—C17—H10 | 109.5 |
N1—C7—C6 | 120.9 (3) | H9—C17—H11 | 109.5 |
N1—C7—C8 | 121.3 (3) | H10—C17—H11 | 109.5 |
C6—C7—C8 | 117.8 (3) | N1—C18—H12 | 108.6 |
C7—C8—C9 | 119.4 (3) | N1—C18—H13 | 108.2 |
O1—C9—C4 | 118.8 (3) | C19—C18—H12 | 108.3 |
O1—C9—C8 | 117.3 (3) | C19—C18—H13 | 108.6 |
C4—C9—C8 | 123.9 (3) | H12—C18—H13 | 109.5 |
C2—C10—C11 | 123.3 (3) | C18—C19—H14 | 109.3 |
C2—C10—C15 | 119.7 (3) | C18—C19—H15 | 109.5 |
C11—C10—C15 | 117.0 (3) | C18—C19—H16 | 109.6 |
C10—C11—C12 | 121.5 (3) | H14—C19—H15 | 109.5 |
C11—C12—C13 | 120.1 (3) | H14—C19—H16 | 109.5 |
C12—C13—C14 | 119.2 (3) | H15—C19—H16 | 109.5 |
C12—C13—C16 | 122.7 (3) | N1—C20—H17 | 108.0 |
C14—C13—C16 | 118.1 (3) | N1—C20—H18 | 108.4 |
C13—C14—C15 | 120.5 (3) | C21—C20—H17 | 108.0 |
C10—C15—C14 | 121.7 (3) | C21—C20—H18 | 108.2 |
O3—C16—O4 | 122.5 (3) | H17—C20—H18 | 109.5 |
O3—C16—C13 | 124.7 (3) | C20—C21—H19 | 109.9 |
O4—C16—C13 | 112.8 (3) | C20—C21—H20 | 109.2 |
N1—C18—C19 | 113.6 (3) | C20—C21—H21 | 109.4 |
N1—C20—C21 | 114.8 (3) | H19—C21—H20 | 109.5 |
C2—C3—H1 | 118.5 | H19—C21—H21 | 109.5 |
C4—C3—H1 | 118.2 | H20—C21—H21 | 109.5 |
C4—C5—H2 | 118.9 | | |
| | | |
C1—O1—C9—C4 | 2.2 (5) | C3—C4—C9—O1 | 1.9 (5) |
C1—O1—C9—C8 | −177.3 (3) | C3—C4—C9—C8 | −178.6 (3) |
C9—O1—C1—O2 | 174.0 (3) | C5—C4—C9—O1 | −178.0 (3) |
C9—O1—C1—C2 | −4.8 (5) | C5—C4—C9—C8 | 1.4 (5) |
C17—O4—C16—O3 | 0.3 (5) | C9—C4—C5—C6 | −1.6 (5) |
C17—O4—C16—C13 | −179.8 (3) | C4—C5—C6—C7 | −0.7 (5) |
C7—N1—C18—C19 | 78.4 (4) | C5—C6—C7—N1 | −174.9 (3) |
C18—N1—C7—C6 | −174.9 (3) | C5—C6—C7—C8 | 3.3 (5) |
C18—N1—C7—C8 | 7.0 (5) | N1—C7—C8—C9 | 174.7 (3) |
C7—N1—C20—C21 | −75.3 (4) | C6—C7—C8—C9 | −3.4 (5) |
C20—N1—C7—C6 | −6.2 (5) | C7—C8—C9—O1 | −179.4 (3) |
C20—N1—C7—C8 | 175.8 (3) | C7—C8—C9—C4 | 1.1 (5) |
C18—N1—C20—C21 | 93.9 (4) | C2—C10—C11—C12 | −178.5 (3) |
C20—N1—C18—C19 | −90.7 (4) | C2—C10—C15—C14 | 178.8 (3) |
O1—C1—C2—C3 | 3.3 (5) | C11—C10—C15—C14 | −0.1 (4) |
O1—C1—C2—C10 | −178.7 (3) | C15—C10—C11—C12 | 0.3 (5) |
O2—C1—C2—C3 | −175.3 (3) | C10—C11—C12—C13 | −0.3 (5) |
O2—C1—C2—C10 | 2.7 (6) | C11—C12—C13—C14 | 0.0 (5) |
C1—C2—C3—C4 | 0.7 (5) | C11—C12—C13—C16 | 177.8 (3) |
C1—C2—C10—C11 | 17.1 (5) | C12—C13—C14—C15 | 0.2 (4) |
C1—C2—C10—C15 | −161.6 (3) | C12—C13—C16—O3 | −173.6 (3) |
C3—C2—C10—C11 | −164.9 (3) | C12—C13—C16—O4 | 6.5 (5) |
C3—C2—C10—C15 | 16.3 (5) | C14—C13—C16—O3 | 4.2 (5) |
C10—C2—C3—C4 | −177.4 (3) | C14—C13—C16—O4 | −175.7 (3) |
C2—C3—C4—C5 | 176.6 (3) | C16—C13—C14—C15 | −177.7 (3) |
C2—C3—C4—C9 | −3.3 (5) | C13—C14—C15—C10 | −0.2 (4) |
C3—C4—C5—C6 | 178.4 (3) | | |
Symmetry codes: (i) x+1, y, z; (ii) −x, y+1/2, −z+3/2; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+1, y−1/2, −z+3/2; (v) −x+1/2, −y, z+1/2; (vi) x−1, y, z; (vii) −x, y−1/2, −z+3/2; (viii) −x+3/2, −y, z+1/2; (ix) −x+1/2, −y, z−1/2; (x) −x+3/2, −y, z−1/2; (xi) x−1/2, −y+1/2, −z+2; (xii) x+1/2, −y+1/2, −z+2; (xiii) x−1/2, −y+1/2, −z+1; (xiv) x+1/2, −y+1/2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H1···O2iv | 0.95 | 2.49 | 3.070 (4) | 120 (1) |
C20—H17···C4vi | 0.95 | 2.86 | 3.476 (5) | 124 (1) |
C21—H20···C16ix | 0.95 | 2.88 | 3.493 (5) | 123 (1) |
Symmetry codes: (iv) −x+1, y−1/2, −z+3/2; (vi) x−1, y, z; (ix) −x+1/2, −y, z−1/2. |