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In the title compound, C21H21NO4, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031138/bt2155sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031138/bt2155Isup2.hkl
Contains datablock I

CCDC reference: 620678

Key indicators

  • Single-crystal X-ray study
  • T = 123 K
  • Mean [sigma](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

Computing details top

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-2H-1-benzopyran-3-yl)benzoate top
Crystal data top
C21H21NO4F(000) = 744.00
Mr = 351.40Dx = 1.358 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71070 Å
Hall symbol: P 2ac 2abCell parameters from 3599 reflections
a = 6.332 (2) Åθ = 3.2–27.5°
b = 12.103 (4) ŵ = 0.09 mm1
c = 22.424 (8) ÅT = 123 K
V = 1718.5 (10) Å3Platelet, yellow
Z = 40.12 × 0.12 × 0.03 mm
Data collection top
Rigaku Saturn
diffractometer
1207 reflections with F2 > 2σ(F2)
Detector resolution: 7.31 pixels mm-1Rint = 0.072
ω scansθmax = 27.5°
Absorption correction: multi-scan
(Jacobson, 1998)
h = 77
Tmin = 0.884, Tmax = 0.997k = 1515
14109 measured reflectionsl = 2929
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) = 0.135Δρmax = 0.34 e Å3
S = 1.01Δρmin = 0.41 e Å3
2249 reflectionsExtinction correction: Larson (1970), equation 22
236 parametersExtinction 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
xyzUiso*/Ueq
O10.2611 (4)0.2128 (2)0.71275 (12)0.0248 (7)
O20.5600 (4)0.2832 (2)0.74415 (12)0.0319 (8)
O31.2575 (4)0.0490 (2)0.94975 (14)0.0439 (9)
O41.2975 (4)0.1353 (2)0.95221 (12)0.0265 (7)
N10.3790 (5)0.0798 (2)0.62716 (14)0.0256 (9)
C10.4415 (5)0.2053 (3)0.74844 (18)0.0228 (10)
C20.4671 (5)0.1063 (3)0.78468 (17)0.0192 (9)
C30.3194 (5)0.0250 (3)0.77919 (16)0.0202 (9)
C40.1453 (5)0.0317 (3)0.73990 (16)0.0192 (9)
C50.0040 (5)0.0515 (3)0.73050 (16)0.0233 (10)
C60.1715 (5)0.0381 (3)0.69271 (16)0.0236 (10)
C70.2020 (5)0.0629 (3)0.66156 (17)0.0212 (9)
C80.0486 (5)0.1458 (3)0.66855 (17)0.0232 (10)
C90.1161 (5)0.1290 (3)0.70697 (17)0.0203 (9)
C100.6523 (5)0.0944 (3)0.82442 (16)0.0208 (9)
C110.7795 (6)0.1833 (3)0.84176 (17)0.0250 (10)
C120.9556 (6)0.1684 (3)0.87821 (17)0.0242 (10)
C131.0081 (5)0.0636 (3)0.89839 (16)0.0215 (9)
C140.8834 (6)0.0255 (3)0.88184 (17)0.0252 (10)
C150.7093 (5)0.0103 (3)0.84555 (16)0.0233 (9)
C161.1968 (6)0.0417 (3)0.93539 (17)0.0259 (10)
C171.4837 (5)0.1179 (3)0.98836 (18)0.0314 (11)
C180.4021 (6)0.1798 (3)0.59127 (18)0.0303 (11)
C190.2763 (8)0.1774 (4)0.53361 (19)0.0431 (13)
C200.5304 (5)0.0096 (3)0.61685 (17)0.0272 (10)
C210.4579 (6)0.0970 (3)0.57260 (17)0.0300 (11)
H10.33350.03930.80310.024*
H20.01160.11980.75100.028*
H30.26870.09700.68720.028*
H40.05990.21300.64690.028*
H50.74580.25560.82830.030*
H61.03960.23010.88920.029*
H70.91840.09760.89530.030*
H80.62620.07240.83460.028*
H91.52170.18571.00690.038*
H101.45400.06421.01810.038*
H111.59720.09290.96410.038*
H120.54710.18900.58160.036*
H130.35580.24090.61440.036*
H140.13960.20710.54060.052*
H150.34650.22030.50420.052*
H160.26370.10330.52010.052*
H170.55630.04510.65390.033*
H180.65800.02170.60240.033*
H190.56940.14770.56510.036*
H200.41810.06210.53640.036*
H210.34010.13560.58860.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0228 (13)0.0182 (14)0.0335 (15)0.0003 (12)0.0022 (12)0.0018 (12)
O20.0290 (16)0.0197 (15)0.0470 (19)0.0040 (14)0.0062 (15)0.0054 (14)
O30.0392 (17)0.0280 (18)0.065 (2)0.0012 (16)0.0204 (17)0.0036 (17)
O40.0234 (13)0.0272 (16)0.0288 (15)0.0021 (12)0.0073 (12)0.0005 (13)
N10.0262 (16)0.0224 (19)0.0282 (18)0.0004 (16)0.0043 (14)0.0008 (16)
C10.0171 (19)0.020 (2)0.032 (2)0.0019 (18)0.0036 (19)0.0006 (19)
C20.0176 (16)0.0155 (19)0.0245 (19)0.0018 (16)0.0051 (16)0.0004 (17)
C30.0232 (18)0.018 (2)0.0189 (18)0.0020 (16)0.0061 (16)0.0001 (16)
C40.0224 (18)0.016 (2)0.0193 (18)0.0031 (17)0.0004 (15)0.0019 (17)
C50.0284 (19)0.021 (2)0.0207 (18)0.0016 (19)0.0033 (17)0.0020 (17)
C60.026 (2)0.022 (2)0.0232 (19)0.0032 (18)0.0031 (16)0.0034 (18)
C70.0206 (17)0.022 (2)0.0209 (18)0.0013 (18)0.0005 (16)0.0036 (17)
C80.0251 (19)0.020 (2)0.025 (2)0.0009 (18)0.0001 (17)0.0007 (17)
C90.0205 (17)0.0141 (19)0.026 (2)0.0026 (16)0.0032 (16)0.0042 (17)
C100.0217 (18)0.019 (2)0.0212 (19)0.0047 (18)0.0027 (15)0.0020 (17)
C110.031 (2)0.018 (2)0.026 (2)0.0036 (19)0.0001 (18)0.0002 (18)
C120.028 (2)0.021 (2)0.0239 (19)0.0007 (19)0.0002 (17)0.0019 (18)
C130.0202 (17)0.023 (2)0.0210 (18)0.0010 (17)0.0008 (15)0.0017 (17)
C140.030 (2)0.020 (2)0.025 (2)0.0038 (18)0.0003 (17)0.0033 (18)
C150.0249 (19)0.021 (2)0.0244 (19)0.0020 (19)0.0006 (17)0.0014 (17)
C160.030 (2)0.023 (2)0.025 (2)0.002 (2)0.0013 (18)0.0008 (18)
C170.0256 (19)0.041 (2)0.028 (2)0.002 (2)0.0057 (18)0.002 (2)
C180.032 (2)0.027 (2)0.033 (2)0.000 (2)0.0065 (19)0.003 (2)
C190.061 (3)0.030 (2)0.038 (2)0.002 (2)0.004 (2)0.003 (2)
C200.0245 (19)0.032 (2)0.0252 (19)0.003 (2)0.0027 (17)0.0027 (19)
C210.034 (2)0.031 (2)0.025 (2)0.001 (2)0.0040 (18)0.0063 (19)
Geometric parameters (Å, º) top
O1—C11.398 (4)C14—C151.382 (5)
O1—C91.375 (4)C18—C191.519 (6)
O2—C11.209 (4)C20—C211.521 (5)
O3—C161.207 (5)C3—H10.950
O4—C161.353 (5)C5—H20.950
O4—C171.446 (4)C6—H30.950
N1—C71.376 (4)C8—H40.950
N1—C181.462 (5)C11—H50.950
N1—C201.464 (5)C12—H60.950
C1—C21.457 (5)C14—H70.950
C2—C31.363 (5)C15—H80.950
C2—C101.480 (5)C17—H90.950
C3—C41.413 (4)C17—H100.950
C4—C51.397 (5)C17—H110.950
C4—C91.402 (5)C18—H120.950
C5—C61.367 (5)C18—H130.950
C6—C71.421 (5)C19—H140.950
C7—C81.405 (5)C19—H150.950
C8—C91.368 (5)C19—H160.950
C10—C111.399 (5)C20—H170.950
C10—C151.400 (5)C20—H180.950
C11—C121.395 (5)C21—H190.950
C12—C131.386 (5)C21—H200.950
C13—C141.388 (5)C21—H210.950
C13—C161.479 (5)
O1···N1i3.387 (4)H3···H6iv3.069
O1···C5ii3.522 (4)H3···H8vi3.385
O1···C18i3.482 (4)H4···O2vi3.357
O2···C3iii3.070 (4)H4···C14iii3.417
O2···C4iii3.558 (4)H4···H2ii3.072
O2···C5iii3.497 (4)H4···H7iii2.636
O2···C6ii3.569 (4)H4···H12i3.574
O2···C7i3.579 (4)H4···H18i3.582
O2···C8i3.432 (4)H5···C5iii3.140
O3···C18iv3.529 (5)H5···C20ii3.383
O3···C19iv3.335 (5)H5···C21ii3.383
O4···C21iii3.441 (5)H5···H2iii2.791
O4···C21v3.482 (4)H5···H3ii3.525
N1···O1vi3.387 (4)H5···H17ii2.724
N1···C1vi3.316 (5)H5···H19ii2.887
C1···N1i3.316 (5)H5···H21ii3.437
C1···C7i3.444 (5)H6···C6iii3.456
C2···C6i3.542 (5)H6···C173.323
C2···C7i3.506 (5)H6···C21iii3.482
C3···O2iv3.070 (4)H6···H3iii3.069
C3···C13vi3.354 (5)H6···H9xi2.545
C3···C16vi3.593 (5)H6···H10xi3.287
C4···O2iv3.558 (4)H6···H19ii3.478
C4···C20i3.476 (5)H6···H21iii2.551
C5···O1vii3.522 (4)H7···O1iv3.525
C5···O2iv3.497 (4)H7···C8iv3.517
C5···C10vi3.506 (5)H7···C19v3.370
C5···C14vi3.482 (5)H7···H1i3.418
C5···C15vi3.194 (5)H7···H2i3.301
C6···O2vii3.569 (4)H7···H4iv2.636
C6···C2vi3.542 (5)H7···H11vi3.441
C6···C10vi3.541 (5)H7···H12vii3.531
C6···C15vi3.526 (5)H7···H13iv3.397
C7···O2vi3.579 (4)H7···H14iv3.101
C7···C1vi3.444 (5)H7···H15v2.894
C7···C2vi3.506 (5)H7···H16v2.964
C8···O2vi3.432 (4)H8···O1iv2.897
C9···C20i3.451 (5)H8···O2iv2.750
C10···C5i3.506 (5)H8···O3vi3.493
C10···C6i3.541 (5)H8···C1iv3.300
C13···C3i3.354 (5)H8···C5i3.316
C14···C5i3.482 (5)H8···C6i3.454
C15···C5i3.194 (5)H8···H2i3.130
C15···C6i3.526 (5)H8···H3i3.385
C16···C3i3.593 (5)H8···H11vi3.533
C16···C21v3.493 (5)H8···H12vii3.483
C17···C21viii3.556 (5)H8···H13vii3.057
C18···O1vi3.482 (4)H9···O4xii2.931
C18···O3iii3.529 (5)H9···C12xii3.152
C19···O3iii3.335 (5)H9···C21iii3.203
C20···C4vi3.476 (5)H9···C21viii3.309
C20···C9vi3.451 (5)H9···H6xii2.545
C21···O4iv3.441 (5)H9···H9xi3.542
C21···O4ix3.482 (4)H9···H9xii3.542
C21···C16ix3.493 (5)H9···H19iii2.601
C21···C17x3.556 (5)H9···H19v3.181
O1···H2ii2.784H9···H20iii3.270
O1···H3ii3.215H9···H20viii2.995
O1···H7iii3.525H9···H21iii3.254
O1···H8iii2.897H9···H21viii2.791
O1···H12i3.196H10···C19viii3.583
O1···H13i3.295H10···C20v3.540
O1···H17i3.581H10···C21v3.394
O1···H18i3.426H10···C21viii3.440
O2···H1iii2.488H10···H6xii3.287
O2···H2iii2.958H10···H14viii3.524
O2···H3ii2.807H10···H16viii2.821
O2···H4i3.357H10···H18v2.858
O2···H8iii2.750H10···H19v2.839
O2···H13i3.001H10···H20v3.418
O2···H17ii3.089H10···H20viii2.967
O3···H1i3.325H10···H21viii3.037
O3···H8i3.493H11···C10i3.153
O3···H13iv2.987H11···C11i3.172
O3···H14iv3.053H11···C12i3.114
O3···H15iv3.030H11···C13i3.011
O3···H15v3.544H11···C14i2.957
O3···H16v3.562H11···C15i3.023
O3···H18v3.495H11···C21viii3.336
O3···H20v3.193H11···H7i3.441
O4···H9xi2.931H11···H8i3.533
O4···H19iii3.165H11···H16viii2.885
O4···H19v2.919H11···H19iii3.212
O4···H20v3.181H11···H20viii2.625
O4···H21iii2.933H11···H21viii3.228
C1···H1iii3.594H12···O1vi3.196
C1···H2ii3.566H12···C19xiii3.375
C1···H3ii3.001H12···H4vi3.574
C1···H8iii3.300H12···H7ii3.531
C1···H13i3.296H12···H8ii3.483
C2···H17i3.461H12···H14xiii3.070
C3···H17i3.038H12···H15xiii2.915
C4···H17i2.855H13···O1vi3.295
C4···H18i3.328H13···O2vi3.001
C5···H5iv3.140H13···O3iii2.987
C5···H8vi3.316H13···C1vi3.296
C5···H17i3.315H13···H1ii3.242
C6···H6iv3.456H13···H7iii3.397
C6···H8vi3.454H13···H8ii3.057
C8···H2ii3.371H14···O3iii3.053
C8···H7iii3.517H14···C18xiv3.588
C8···H18i3.252H14···C19xiv3.165
C9···H2ii3.286H14···H7iii3.101
C9···H17i3.187H14···H10x3.524
C9···H18i3.038H14···H12xiv3.070
C10···H11vi3.153H14···H15xiv2.286
C11···H2iii3.428H14···H16xiv3.575
C11···H11vi3.172H15···O3iii3.030
C11···H17ii3.579H15···O3ix3.544
C11···H19ii3.212H15···C19xiii3.108
C12···H9xi3.152H15···H7ix2.894
C12···H11vi3.114H15···H12xiv2.915
C12···H19ii3.543H15···H14xiii2.286
C12···H21iii3.480H15···H15xiii3.252
C13···H1i3.219H15···H15xiv3.252
C13···H11vi3.011H15···H16xiii3.440
C13···H20v3.146H16···O3ix3.562
C14···H1i3.356H16···C14ix3.327
C14···H2i3.252H16···C17x3.289
C14···H4iv3.417H16···H7ix2.964
C14···H11vi2.957H16···H10x2.821
C14···H16v3.327H16···H11x2.885
C15···H2i3.149H16···H14xiii3.575
C15···H11vi3.023H16···H15xiv3.440
C16···H1i3.242H17···O1vi3.581
C16···H19v3.280H17···O2vii3.089
C16···H20v2.882H17···C2vi3.461
C17···H6xii3.323H17···C3vi3.038
C17···H16viii3.289H17···C4vi2.855
C17···H19iii3.127H17···C5vi3.315
C17···H19v3.158H17···C9vi3.187
C17···H20viii3.030H17···C11vii3.579
C17···H21iii3.565H17···H1vi3.418
C17···H21viii3.192H17···H5vii2.724
C18···H14xiii3.588H18···O1vi3.426
C19···H7ix3.370H18···O3ix3.495
C19···H10x3.583H18···C4vi3.328
C19···H12xiv3.375H18···C8vi3.252
C19···H14xiii3.165H18···C9vi3.038
C19···H15xiv3.108H18···H4vi3.582
C20···H5vii3.383H18···H10ix2.858
C20···H10ix3.540H19···O4iv3.165
C21···H5vii3.383H19···O4ix2.919
C21···H6iv3.482H19···C11vii3.212
C21···H9iv3.203H19···C12vii3.543
C21···H9x3.309H19···C16ix3.280
C21···H10ix3.394H19···C17iv3.127
C21···H10x3.440H19···C17ix3.158
C21···H11x3.336H19···H5vii2.887
H1···O2iv2.488H19···H6vii3.478
H1···O3vi3.325H19···H9iv2.601
H1···C1iv3.594H19···H9ix3.181
H1···C13vi3.219H19···H10ix2.839
H1···C14vi3.356H19···H11iv3.212
H1···C16vi3.242H20···O3ix3.193
H1···H7vi3.418H20···O4ix3.181
H1···H13vii3.242H20···C13ix3.146
H1···H17i3.418H20···C16ix2.882
H2···O1vii2.784H20···C17x3.030
H2···O2iv2.958H20···H9iv3.270
H2···C1vii3.566H20···H9x2.995
H2···C8vii3.371H20···H10ix3.418
H2···C9vii3.286H20···H10x2.967
H2···C11iv3.428H20···H11x2.625
H2···C14vi3.252H21···O4iv2.933
H2···C15vi3.149H21···C12iv3.480
H2···H4vii3.072H21···C17iv3.565
H2···H5iv2.791H21···C17x3.192
H2···H7vi3.301H21···H5vii3.437
H2···H8vi3.130H21···H6iv2.551
H3···O1vii3.215H21···H9iv3.254
H3···O2vii2.807H21···H9x2.791
H3···C1vii3.001H21···H10x3.037
H3···H5vii3.525H21···H11x3.228
C1—O1—C9123.5 (3)C6—C5—H2118.9
C16—O4—C17114.8 (3)C5—C6—H3119.6
C7—N1—C18120.9 (3)C7—C6—H3119.6
C7—N1—C20120.8 (3)C7—C8—H4120.2
C18—N1—C20117.4 (3)C9—C8—H4120.4
O1—C1—O2114.3 (3)C10—C11—H5119.4
O1—C1—C2117.6 (3)C12—C11—H5119.1
O2—C1—C2128.1 (3)C11—C12—H6119.9
C1—C2—C3117.9 (3)C13—C12—H6120.0
C1—C2—C10120.2 (3)C13—C14—H7119.8
C3—C2—C10121.9 (3)C15—C14—H7119.7
C2—C3—C4123.4 (3)C10—C15—H8119.0
C3—C4—C5125.5 (3)C14—C15—H8119.2
C3—C4—C9118.6 (3)O4—C17—H9109.1
C5—C4—C9115.9 (3)O4—C17—H10109.3
C4—C5—C6122.2 (3)O4—C17—H11110.0
C5—C6—C7120.8 (3)H9—C17—H10109.5
N1—C7—C6120.9 (3)H9—C17—H11109.5
N1—C7—C8121.3 (3)H10—C17—H11109.5
C6—C7—C8117.8 (3)N1—C18—H12108.6
C7—C8—C9119.4 (3)N1—C18—H13108.2
O1—C9—C4118.8 (3)C19—C18—H12108.3
O1—C9—C8117.3 (3)C19—C18—H13108.6
C4—C9—C8123.9 (3)H12—C18—H13109.5
C2—C10—C11123.3 (3)C18—C19—H14109.3
C2—C10—C15119.7 (3)C18—C19—H15109.5
C11—C10—C15117.0 (3)C18—C19—H16109.6
C10—C11—C12121.5 (3)H14—C19—H15109.5
C11—C12—C13120.1 (3)H14—C19—H16109.5
C12—C13—C14119.2 (3)H15—C19—H16109.5
C12—C13—C16122.7 (3)N1—C20—H17108.0
C14—C13—C16118.1 (3)N1—C20—H18108.4
C13—C14—C15120.5 (3)C21—C20—H17108.0
C10—C15—C14121.7 (3)C21—C20—H18108.2
O3—C16—O4122.5 (3)H17—C20—H18109.5
O3—C16—C13124.7 (3)C20—C21—H19109.9
O4—C16—C13112.8 (3)C20—C21—H20109.2
N1—C18—C19113.6 (3)C20—C21—H21109.4
N1—C20—C21114.8 (3)H19—C21—H20109.5
C2—C3—H1118.5H19—C21—H21109.5
C4—C3—H1118.2H20—C21—H21109.5
C4—C5—H2118.9
C1—O1—C9—C42.2 (5)C3—C4—C9—O11.9 (5)
C1—O1—C9—C8177.3 (3)C3—C4—C9—C8178.6 (3)
C9—O1—C1—O2174.0 (3)C5—C4—C9—O1178.0 (3)
C9—O1—C1—C24.8 (5)C5—C4—C9—C81.4 (5)
C17—O4—C16—O30.3 (5)C9—C4—C5—C61.6 (5)
C17—O4—C16—C13179.8 (3)C4—C5—C6—C70.7 (5)
C7—N1—C18—C1978.4 (4)C5—C6—C7—N1174.9 (3)
C18—N1—C7—C6174.9 (3)C5—C6—C7—C83.3 (5)
C18—N1—C7—C87.0 (5)N1—C7—C8—C9174.7 (3)
C7—N1—C20—C2175.3 (4)C6—C7—C8—C93.4 (5)
C20—N1—C7—C66.2 (5)C7—C8—C9—O1179.4 (3)
C20—N1—C7—C8175.8 (3)C7—C8—C9—C41.1 (5)
C18—N1—C20—C2193.9 (4)C2—C10—C11—C12178.5 (3)
C20—N1—C18—C1990.7 (4)C2—C10—C15—C14178.8 (3)
O1—C1—C2—C33.3 (5)C11—C10—C15—C140.1 (4)
O1—C1—C2—C10178.7 (3)C15—C10—C11—C120.3 (5)
O2—C1—C2—C3175.3 (3)C10—C11—C12—C130.3 (5)
O2—C1—C2—C102.7 (6)C11—C12—C13—C140.0 (5)
C1—C2—C3—C40.7 (5)C11—C12—C13—C16177.8 (3)
C1—C2—C10—C1117.1 (5)C12—C13—C14—C150.2 (4)
C1—C2—C10—C15161.6 (3)C12—C13—C16—O3173.6 (3)
C3—C2—C10—C11164.9 (3)C12—C13—C16—O46.5 (5)
C3—C2—C10—C1516.3 (5)C14—C13—C16—O34.2 (5)
C10—C2—C3—C4177.4 (3)C14—C13—C16—O4175.7 (3)
C2—C3—C4—C5176.6 (3)C16—C13—C14—C15177.7 (3)
C2—C3—C4—C93.3 (5)C13—C14—C15—C100.2 (4)
C3—C4—C5—C6178.4 (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, y1/2, z+3/2; (v) x+1/2, y, z+1/2; (vi) x1, y, z; (vii) x, y1/2, z+3/2; (viii) x+3/2, y, z+1/2; (ix) x+1/2, y, z1/2; (x) x+3/2, y, z1/2; (xi) x1/2, y+1/2, z+2; (xii) x+1/2, y+1/2, z+2; (xiii) x1/2, y+1/2, z+1; (xiv) x+1/2, y+1/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H1···O2iv0.952.493.070 (4)120 (1)
C20—H17···C4vi0.952.863.476 (5)124 (1)
C21—H20···C16ix0.952.883.493 (5)123 (1)
Symmetry codes: (iv) x+1, y1/2, z+3/2; (vi) x1, y, z; (ix) x+1/2, y, z1/2.
 

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