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The title compound, C21H20N4O5S, crystallizes with two mol­ecules in the asymmetric unit. The crystal structure is stabilized by a network of C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048835/lh2252sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048835/lh2252Isup2.hkl
Contains datablock I

CCDC reference: 630171

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.042
  • wR factor = 0.091
  • Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for N7
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.61 Ratio PLAT220_ALERT_2_C Large Non-Solvent N Ueq(max)/Ueq(min) ... 2.58 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for N2 - N3 .. 6.73 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C31 - C32 .. 5.14 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C4 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for N6 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C2 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 1 C20 -N2 -N3 -N4 18.00 0.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 2 C41 -N6 -N7 -N8 18.00 0.00 1.555 1.555 1.555 1.555
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 25.02 From the CIF: _reflns_number_total 7497 Count of symmetry unique reflns 4225 Completeness (_total/calc) 177.44% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3272 Fraction of Friedel pairs measured 0.774 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C18 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C20 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C36 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C39 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C41 = . S
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 7 ALERT level G = General alerts; check 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Diphenylmethyl 3-azido-1,1-dioxocephalosporanate top
Crystal data top
C21H20N4O5SF(000) = 1840
Mr = 440.47Dx = 1.375 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5653 reflections
a = 10.9030 (13) Åθ = 2.4–21.8°
b = 11.3796 (14) ŵ = 0.19 mm1
c = 34.293 (4) ÅT = 294 K
V = 4254.8 (9) Å3Block, colorless
Z = 80.24 × 0.22 × 0.18 mm
Data collection top
Bruker SMART-1000 CCD area-detector
diffractometer
7497 independent reflections
Radiation source: fine-focus sealed tube5529 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
φ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1211
Tmin = 0.943, Tmax = 0.966k = 913
20301 measured reflectionsl = 4040
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.092 w = 1/[σ2(Fo2) + (0.0408P)2 + 0.1929P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
7497 reflectionsΔρmax = 0.20 e Å3
561 parametersΔρmin = 0.25 e Å3
18 restraintsAbsolute structure: Flack (1983), 2607 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.04 (6)
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.89693 (6)1.25811 (7)0.94228 (2)0.04747 (19)
S20.55483 (8)0.03894 (7)0.81075 (2)0.0574 (2)
O10.55441 (18)0.93528 (15)0.94762 (5)0.0494 (5)
O20.7399 (2)0.96878 (19)0.92215 (7)0.0768 (7)
O30.5002 (2)1.35293 (18)0.93499 (6)0.0654 (6)
O41.00413 (17)1.2272 (2)0.92039 (6)0.0680 (6)
O50.89415 (19)1.36889 (17)0.96202 (6)0.0598 (5)
O60.77230 (18)0.34298 (18)0.76097 (6)0.0633 (6)
O70.76923 (18)0.23061 (17)0.81479 (6)0.0570 (5)
O80.3275 (2)0.2679 (2)0.78208 (9)0.0982 (9)
O90.6129 (2)0.1087 (2)0.84020 (7)0.0894 (8)
O100.4463 (2)0.0812 (2)0.79205 (8)0.0855 (8)
N10.65556 (19)1.21074 (18)0.92983 (6)0.0395 (5)
N20.6928 (2)1.2520 (2)1.00897 (6)0.0454 (6)
N30.7504 (2)1.2875 (2)1.03751 (8)0.0534 (6)
N40.7945 (3)1.3314 (3)1.06368 (9)0.0885 (10)
N50.5199 (2)0.18823 (19)0.79781 (7)0.0513 (6)
N60.5202 (3)0.0705 (4)0.72513 (9)0.0992 (12)
N70.5239 (3)0.0120 (3)0.69639 (9)0.0784 (9)
N80.5139 (4)0.0419 (4)0.66900 (12)0.1323 (16)
C10.5532 (3)0.8129 (2)0.93433 (8)0.0462 (7)
H10.61990.80120.91560.055*
C20.5739 (3)0.7347 (2)0.96881 (8)0.0464 (7)
C30.6661 (3)0.6531 (3)0.96900 (11)0.0694 (10)
H30.71980.64880.94800.083*
C40.6804 (4)0.5767 (3)1.00012 (14)0.0906 (13)
H40.74220.52040.99950.109*
C50.6052 (4)0.5833 (3)1.03134 (12)0.0791 (11)
H50.61540.53221.05220.095*
C60.5146 (4)0.6651 (3)1.03207 (10)0.0834 (12)
H60.46310.67021.05360.100*
C70.4983 (3)0.7410 (3)1.00097 (9)0.0702 (9)
H70.43590.79661.00180.084*
C80.4319 (3)0.7911 (2)0.91417 (7)0.0458 (7)
C90.3937 (3)0.6768 (3)0.90808 (9)0.0660 (9)
H90.44140.61450.91700.079*
C100.2839 (4)0.6545 (3)0.88866 (11)0.0782 (11)
H100.25830.57740.88480.094*
C110.2145 (3)0.7443 (3)0.87541 (9)0.0692 (10)
H110.14170.72890.86220.083*
C120.2508 (3)0.8575 (3)0.88133 (9)0.0659 (9)
H120.20240.91910.87240.079*
C130.3590 (3)0.8806 (3)0.90055 (9)0.0567 (8)
H130.38320.95820.90440.068*
C140.6523 (3)0.9998 (2)0.94046 (8)0.0432 (7)
C150.6405 (2)1.1210 (2)0.95915 (7)0.0380 (6)
H150.55771.12810.97000.046*
C160.5968 (3)1.3166 (2)0.92411 (8)0.0452 (7)
C170.7028 (3)1.3631 (3)0.89984 (9)0.0543 (8)
H17A0.74231.43230.91060.065*
H17B0.68411.37320.87240.065*
C180.7674 (2)1.2465 (3)0.90976 (7)0.0454 (7)
H180.78491.19860.88670.055*
C190.8662 (3)1.1452 (2)0.97667 (8)0.0450 (7)
H19A0.88581.07040.96460.054*
H19B0.92141.15540.99860.054*
C200.7339 (3)1.1381 (2)0.99267 (7)0.0412 (7)
C210.7241 (3)1.0402 (2)1.02283 (8)0.0568 (8)
H21A0.64141.03601.03240.085*
H21B0.77881.05621.04410.085*
H21C0.74590.96661.01100.085*
C220.8926 (3)0.3910 (3)0.77155 (9)0.0569 (8)
H220.94590.32590.77940.068*
C230.9408 (3)0.4414 (3)0.73362 (9)0.0529 (8)
C241.0167 (3)0.3747 (3)0.71039 (12)0.0749 (10)
H241.04070.30060.71890.090*
C251.0576 (4)0.4144 (4)0.67501 (12)0.0857 (12)
H251.10970.36790.66010.103*
C261.0221 (4)0.5222 (4)0.66163 (12)0.0803 (12)
H261.04810.54860.63730.096*
C270.9477 (4)0.5914 (3)0.68437 (11)0.0774 (10)
H270.92440.66560.67570.093*
C280.9074 (3)0.5506 (3)0.72008 (10)0.0678 (9)
H280.85670.59780.73530.081*
C290.8796 (3)0.4736 (3)0.80542 (10)0.0631 (9)
C300.7869 (4)0.5561 (3)0.80758 (13)0.0868 (12)
H300.72990.56050.78750.104*
C310.7765 (5)0.6323 (4)0.83875 (18)0.1135 (17)
H310.71340.68710.84010.136*
C320.8619 (7)0.6240 (5)0.86739 (18)0.130 (2)
H320.85690.67630.88820.156*
C330.9535 (5)0.5447 (5)0.86759 (15)0.1164 (17)
H331.00840.54070.88830.140*
C340.9636 (4)0.4677 (4)0.83550 (12)0.0852 (12)
H341.02700.41310.83460.102*
C350.7251 (3)0.2616 (3)0.78476 (9)0.0505 (7)
C360.6096 (3)0.2096 (3)0.76752 (8)0.0540 (8)
H360.57510.26580.74880.065*
C370.3964 (3)0.2088 (3)0.80102 (10)0.0656 (9)
C380.3869 (3)0.1305 (3)0.83643 (9)0.0650 (9)
H38A0.33290.06350.83310.078*
H38B0.36980.17190.86050.078*
C390.5234 (3)0.1032 (2)0.82972 (8)0.0499 (7)
H390.57670.12630.85140.060*
C400.6661 (3)0.0055 (3)0.77482 (8)0.0561 (8)
H40A0.74180.01450.78810.067*
H40B0.68160.07640.75990.067*
C410.6375 (3)0.0933 (3)0.74590 (8)0.0616 (9)
C420.7454 (3)0.1063 (4)0.71787 (9)0.0867 (12)
H42A0.73080.17140.70070.130*
H42B0.75420.03570.70280.130*
H42C0.81920.12010.73250.130*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0375 (4)0.0612 (5)0.0438 (4)0.0068 (3)0.0020 (3)0.0025 (4)
S20.0614 (5)0.0450 (4)0.0659 (5)0.0074 (4)0.0016 (4)0.0008 (4)
O10.0512 (12)0.0344 (10)0.0627 (12)0.0080 (9)0.0087 (10)0.0023 (9)
O20.0607 (15)0.0714 (15)0.0984 (18)0.0189 (12)0.0257 (14)0.0375 (14)
O30.0494 (14)0.0668 (14)0.0799 (16)0.0125 (11)0.0106 (12)0.0185 (12)
O40.0384 (12)0.1104 (18)0.0552 (12)0.0008 (12)0.0058 (9)0.0059 (13)
O50.0644 (13)0.0586 (13)0.0564 (12)0.0186 (11)0.0054 (11)0.0044 (10)
O60.0481 (13)0.0656 (13)0.0763 (15)0.0155 (11)0.0167 (11)0.0289 (12)
O70.0631 (13)0.0605 (13)0.0474 (12)0.0075 (11)0.0154 (10)0.0099 (10)
O80.0546 (15)0.0974 (19)0.143 (2)0.0033 (14)0.0043 (15)0.0626 (19)
O90.0932 (18)0.0683 (16)0.1068 (19)0.0199 (14)0.0140 (16)0.0441 (14)
O100.0674 (15)0.0772 (16)0.1118 (19)0.0289 (13)0.0058 (15)0.0359 (14)
N10.0351 (13)0.0449 (13)0.0384 (12)0.0057 (11)0.0025 (10)0.0036 (10)
N20.0513 (15)0.0461 (14)0.0387 (13)0.0055 (12)0.0055 (11)0.0095 (12)
N30.0516 (16)0.0526 (16)0.0559 (16)0.0045 (13)0.0030 (14)0.0080 (13)
N40.097 (2)0.085 (2)0.083 (2)0.0178 (17)0.0390 (19)0.0403 (19)
N50.0500 (17)0.0450 (14)0.0590 (16)0.0056 (12)0.0007 (13)0.0151 (12)
N60.076 (2)0.166 (3)0.0555 (19)0.017 (2)0.0229 (17)0.025 (2)
N70.089 (2)0.089 (2)0.058 (2)0.0279 (18)0.0310 (18)0.0104 (17)
N80.165 (4)0.135 (3)0.097 (3)0.041 (3)0.050 (3)0.035 (3)
C10.0508 (17)0.0346 (15)0.0530 (17)0.0033 (13)0.0050 (15)0.0028 (13)
C20.0487 (18)0.0369 (15)0.0537 (17)0.0050 (14)0.0040 (14)0.0032 (14)
C30.067 (2)0.054 (2)0.087 (3)0.0108 (18)0.011 (2)0.0082 (19)
C40.083 (3)0.068 (3)0.121 (4)0.012 (2)0.016 (3)0.027 (3)
C50.096 (3)0.065 (2)0.076 (3)0.013 (2)0.027 (2)0.018 (2)
C60.113 (3)0.080 (3)0.057 (2)0.003 (2)0.006 (2)0.010 (2)
C70.082 (2)0.068 (2)0.061 (2)0.0154 (19)0.0052 (18)0.0082 (18)
C80.061 (2)0.0412 (16)0.0354 (15)0.0059 (15)0.0038 (13)0.0047 (12)
C90.085 (2)0.0463 (19)0.067 (2)0.0141 (17)0.020 (2)0.0019 (16)
C100.096 (3)0.061 (2)0.078 (3)0.029 (2)0.017 (2)0.005 (2)
C110.067 (2)0.089 (3)0.0509 (19)0.028 (2)0.0051 (16)0.003 (2)
C120.059 (2)0.074 (2)0.065 (2)0.0026 (19)0.0022 (19)0.0107 (18)
C130.060 (2)0.0471 (19)0.063 (2)0.0082 (16)0.0041 (17)0.0059 (15)
C140.0448 (18)0.0442 (16)0.0407 (16)0.0065 (14)0.0013 (14)0.0011 (13)
C150.0334 (16)0.0430 (16)0.0375 (14)0.0030 (12)0.0002 (12)0.0001 (12)
C160.0411 (18)0.0531 (18)0.0412 (16)0.0024 (15)0.0040 (15)0.0052 (13)
C170.0508 (19)0.0614 (19)0.0508 (18)0.0028 (15)0.0029 (15)0.0169 (15)
C180.0382 (16)0.0616 (18)0.0365 (14)0.0055 (15)0.0014 (12)0.0016 (14)
C190.0449 (18)0.0473 (17)0.0427 (16)0.0037 (13)0.0109 (13)0.0060 (13)
C200.0501 (18)0.0371 (16)0.0364 (15)0.0012 (13)0.0035 (13)0.0005 (12)
C210.070 (2)0.0520 (18)0.0485 (18)0.0001 (16)0.0055 (16)0.0117 (15)
C220.0404 (17)0.0537 (19)0.077 (2)0.0000 (15)0.0083 (16)0.0119 (17)
C230.0430 (18)0.0492 (19)0.066 (2)0.0100 (15)0.0042 (16)0.0068 (16)
C240.063 (2)0.060 (2)0.102 (3)0.0060 (18)0.006 (2)0.004 (2)
C250.071 (3)0.093 (3)0.093 (3)0.009 (2)0.022 (2)0.006 (2)
C260.075 (3)0.096 (3)0.070 (2)0.041 (2)0.004 (2)0.001 (2)
C270.085 (3)0.066 (2)0.081 (3)0.022 (2)0.002 (2)0.016 (2)
C280.066 (2)0.060 (2)0.078 (2)0.0051 (18)0.0057 (19)0.0063 (18)
C290.054 (2)0.061 (2)0.074 (2)0.0137 (18)0.0062 (19)0.0103 (18)
C300.095 (3)0.068 (2)0.098 (3)0.008 (2)0.031 (2)0.018 (2)
C310.132 (4)0.081 (3)0.128 (4)0.004 (3)0.060 (3)0.012 (3)
C320.170 (6)0.094 (4)0.126 (4)0.064 (4)0.065 (4)0.007 (3)
C330.117 (4)0.137 (4)0.095 (3)0.076 (4)0.002 (3)0.003 (3)
C340.078 (3)0.094 (3)0.083 (3)0.041 (2)0.004 (2)0.006 (2)
C350.0563 (19)0.0469 (17)0.0482 (18)0.0047 (15)0.0062 (15)0.0108 (15)
C360.0510 (19)0.063 (2)0.0484 (17)0.0134 (16)0.0089 (15)0.0188 (15)
C370.057 (2)0.054 (2)0.085 (2)0.0010 (17)0.0055 (19)0.0207 (18)
C380.069 (2)0.058 (2)0.068 (2)0.0003 (18)0.0150 (18)0.0084 (17)
C390.058 (2)0.0480 (18)0.0436 (16)0.0029 (15)0.0013 (15)0.0029 (14)
C400.055 (2)0.0579 (19)0.0551 (19)0.0047 (16)0.0062 (16)0.0167 (15)
C410.049 (2)0.102 (3)0.0337 (16)0.0139 (18)0.0089 (14)0.0023 (17)
C420.072 (3)0.142 (4)0.046 (2)0.018 (2)0.0099 (18)0.004 (2)
Geometric parameters (Å, º) top
S1—O51.431 (2)C15—C201.548 (4)
S1—O41.433 (2)C15—H150.9800
S1—C191.776 (3)C16—C171.519 (4)
S1—C181.804 (3)C17—C181.541 (4)
S2—O101.429 (2)C17—H17A0.9700
S2—O91.432 (2)C17—H17B0.9700
S2—C401.771 (3)C18—H180.9800
S2—C391.777 (3)C19—C201.546 (4)
O1—C141.318 (3)C19—H19A0.9700
O1—C11.466 (3)C19—H19B0.9700
O2—C141.196 (3)C20—C211.524 (4)
O3—C161.191 (3)C21—H21A0.9600
O6—C351.337 (3)C21—H21B0.9600
O6—C221.467 (3)C21—H21C0.9600
O7—C351.190 (3)C22—C291.500 (4)
O8—C371.198 (4)C22—C231.516 (4)
N1—C161.379 (3)C22—H220.9800
N1—C151.443 (3)C23—C281.375 (4)
N1—C181.458 (3)C23—C241.377 (4)
N2—N31.231 (3)C24—C251.369 (5)
N2—C201.481 (3)C24—H240.9300
N3—N41.134 (3)C25—C261.366 (5)
N5—C371.371 (4)C25—H250.9300
N5—C361.447 (4)C26—C271.373 (5)
N5—C391.461 (3)C26—H260.9300
N6—N71.190 (4)C27—C281.381 (4)
N6—C411.486 (4)C27—H270.9300
N7—N81.127 (4)C28—H280.9300
C1—C21.497 (4)C29—C341.381 (5)
C1—C81.513 (4)C29—C301.382 (5)
C1—H10.9800C30—C311.381 (6)
C2—C31.369 (4)C30—H300.9300
C2—C71.379 (4)C31—C321.357 (7)
C3—C41.385 (5)C31—H310.9300
C3—H30.9300C32—C331.345 (7)
C4—C51.351 (6)C32—H320.9300
C4—H40.9300C33—C341.411 (6)
C5—C61.357 (5)C33—H330.9300
C5—H50.9300C34—H340.9300
C6—C71.384 (5)C35—C361.512 (4)
C6—H60.9300C36—C411.547 (4)
C7—H70.9300C36—H360.9800
C8—C131.374 (4)C37—C381.510 (4)
C8—C91.382 (4)C38—C391.537 (4)
C9—C101.393 (5)C38—H38A0.9700
C9—H90.9300C38—H38B0.9700
C10—C111.351 (5)C39—H390.9800
C10—H100.9300C40—C411.531 (4)
C11—C121.362 (4)C40—H40A0.9700
C11—H110.9300C40—H40B0.9700
C12—C131.377 (4)C41—C421.527 (4)
C12—H120.9300C42—H42A0.9600
C13—H130.9300C42—H42B0.9600
C14—C151.527 (4)C42—H42C0.9600
O5—S1—O4118.78 (14)N2—C20—C21111.3 (2)
O5—S1—C19108.60 (12)N2—C20—C19111.7 (2)
O4—S1—C19108.91 (14)C21—C20—C19110.2 (2)
O5—S1—C18109.91 (13)N2—C20—C15101.0 (2)
O4—S1—C18107.25 (12)C21—C20—C15111.5 (2)
C19—S1—C18102.11 (13)C19—C20—C15110.9 (2)
O10—S2—O9119.75 (16)C20—C21—H21A109.5
O10—S2—C40109.10 (15)C20—C21—H21B109.5
O9—S2—C40107.88 (15)H21A—C21—H21B109.5
O10—S2—C39108.11 (15)C20—C21—H21C109.5
O9—S2—C39109.37 (15)H21A—C21—H21C109.5
C40—S2—C39101.02 (14)H21B—C21—H21C109.5
C14—O1—C1118.6 (2)O6—C22—C29109.9 (3)
C35—O6—C22116.8 (2)O6—C22—C23103.8 (2)
C16—N1—C15131.7 (2)C29—C22—C23117.4 (3)
C16—N1—C1894.5 (2)O6—C22—H22108.5
C15—N1—C18128.4 (2)C29—C22—H22108.5
N3—N2—C20115.6 (2)C23—C22—H22108.5
N4—N3—N2171.9 (3)C28—C23—C24117.5 (3)
C37—N5—C36133.8 (3)C28—C23—C22122.7 (3)
C37—N5—C3994.5 (2)C24—C23—C22119.7 (3)
C36—N5—C39129.2 (2)C25—C24—C23121.7 (4)
N7—N6—C41117.7 (3)C25—C24—H24119.1
N8—N7—N6172.5 (5)C23—C24—H24119.1
O1—C1—C2108.5 (2)C26—C25—C24120.1 (4)
O1—C1—C8107.8 (2)C26—C25—H25119.9
C2—C1—C8113.3 (2)C24—C25—H25119.9
O1—C1—H1109.0C25—C26—C27119.4 (4)
C2—C1—H1109.0C25—C26—H26120.3
C8—C1—H1109.0C27—C26—H26120.3
C3—C2—C7118.1 (3)C26—C27—C28119.9 (4)
C3—C2—C1121.2 (3)C26—C27—H27120.0
C7—C2—C1120.7 (3)C28—C27—H27120.0
C2—C3—C4120.8 (4)C23—C28—C27121.2 (3)
C2—C3—H3119.6C23—C28—H28119.4
C4—C3—H3119.6C27—C28—H28119.4
C5—C4—C3120.5 (4)C34—C29—C30118.5 (4)
C5—C4—H4119.8C34—C29—C22119.1 (3)
C3—C4—H4119.8C30—C29—C22122.4 (3)
C4—C5—C6119.6 (4)C31—C30—C29121.9 (5)
C4—C5—H5120.2C31—C30—H30119.1
C6—C5—H5120.2C29—C30—H30119.1
C5—C6—C7120.5 (4)C32—C31—C30117.4 (5)
C5—C6—H6119.8C32—C31—H31121.3
C7—C6—H6119.8C30—C31—H31121.3
C2—C7—C6120.5 (3)C33—C32—C31124.0 (6)
C2—C7—H7119.8C33—C32—H32118.0
C6—C7—H7119.8C31—C32—H32118.0
C13—C8—C9118.2 (3)C32—C33—C34118.1 (5)
C13—C8—C1122.6 (2)C32—C33—H33121.0
C9—C8—C1119.2 (3)C34—C33—H33121.0
C8—C9—C10120.2 (3)C29—C34—C33120.1 (4)
C8—C9—H9119.9C29—C34—H34120.0
C10—C9—H9119.9C33—C34—H34120.0
C11—C10—C9120.3 (3)O7—C35—O6125.3 (3)
C11—C10—H10119.8O7—C35—C36124.0 (3)
C9—C10—H10119.8O6—C35—C36110.7 (2)
C10—C11—C12120.1 (3)N5—C36—C35110.4 (2)
C10—C11—H11119.9N5—C36—C41109.5 (2)
C12—C11—H11119.9C35—C36—C41111.0 (2)
C11—C12—C13120.1 (3)N5—C36—H36108.7
C11—C12—H12120.0C35—C36—H36108.7
C13—C12—H12120.0C41—C36—H36108.7
C8—C13—C12121.1 (3)O8—C37—N5131.9 (3)
C8—C13—H13119.5O8—C37—C38136.4 (3)
C12—C13—H13119.5N5—C37—C3891.7 (3)
O2—C14—O1125.5 (2)C37—C38—C3986.1 (2)
O2—C14—C15123.6 (3)C37—C38—H38A114.3
O1—C14—C15110.9 (2)C39—C38—H38A114.3
N1—C15—C14109.7 (2)C37—C38—H38B114.3
N1—C15—C20110.7 (2)C39—C38—H38B114.3
C14—C15—C20111.7 (2)H38A—C38—H38B111.4
N1—C15—H15108.2N5—C39—C3887.3 (2)
C14—C15—H15108.2N5—C39—S2109.48 (19)
C20—C15—H15108.2C38—C39—S2115.1 (2)
O3—C16—N1132.0 (3)N5—C39—H39114.0
O3—C16—C17136.3 (3)C38—C39—H39114.0
N1—C16—C1791.6 (2)S2—C39—H39114.0
C16—C17—C1885.8 (2)C41—C40—S2118.0 (2)
C16—C17—H17A114.3C41—C40—H40A107.8
C18—C17—H17A114.3S2—C40—H40A107.8
C16—C17—H17B114.3C41—C40—H40B107.8
C18—C17—H17B114.3S2—C40—H40B107.8
H17A—C17—H17B111.5H40A—C40—H40B107.1
N1—C18—C1787.8 (2)N6—C41—C42112.2 (2)
N1—C18—S1112.54 (17)N6—C41—C40111.0 (3)
C17—C18—S1115.5 (2)C42—C41—C40108.8 (3)
N1—C18—H18112.9N6—C41—C36102.1 (3)
C17—C18—H18112.9C42—C41—C36111.7 (3)
S1—C18—H18112.9C40—C41—C36111.0 (2)
C20—C19—S1116.75 (19)C41—C42—H42A109.5
C20—C19—H19A108.1C41—C42—H42B109.5
S1—C19—H19A108.1H42A—C42—H42B109.5
C20—C19—H19B108.1C41—C42—H42C109.5
S1—C19—H19B108.1H42A—C42—H42C109.5
H19A—C19—H19B107.3H42B—C42—H42C109.5
C20—N2—N3—N4180 (100)C14—C15—C20—C1968.9 (3)
C41—N6—N7—N8179 (100)C35—O6—C22—C2974.2 (3)
C14—O1—C1—C2104.2 (3)C35—O6—C22—C23159.4 (3)
C14—O1—C1—C8132.8 (2)O6—C22—C23—C2882.1 (3)
O1—C1—C2—C3125.6 (3)C29—C22—C23—C2839.4 (4)
C8—C1—C2—C3114.7 (3)O6—C22—C23—C2494.8 (3)
O1—C1—C2—C756.1 (4)C29—C22—C23—C24143.7 (3)
C8—C1—C2—C763.7 (3)C28—C23—C24—C250.2 (5)
C7—C2—C3—C42.0 (5)C22—C23—C24—C25176.8 (3)
C1—C2—C3—C4176.4 (3)C23—C24—C25—C260.9 (6)
C2—C3—C4—C51.6 (6)C24—C25—C26—C271.6 (6)
C3—C4—C5—C60.4 (6)C25—C26—C27—C281.3 (5)
C4—C5—C6—C70.5 (6)C24—C23—C28—C270.5 (5)
C3—C2—C7—C61.1 (5)C22—C23—C28—C27176.4 (3)
C1—C2—C7—C6177.2 (3)C26—C27—C28—C230.3 (5)
C5—C6—C7—C20.1 (6)O6—C22—C29—C34136.3 (3)
O1—C1—C8—C1318.8 (3)C23—C22—C29—C34105.4 (3)
C2—C1—C8—C13138.9 (3)O6—C22—C29—C3044.1 (4)
O1—C1—C8—C9163.0 (3)C23—C22—C29—C3074.2 (4)
C2—C1—C8—C942.9 (4)C34—C29—C30—C310.1 (5)
C13—C8—C9—C100.1 (5)C22—C29—C30—C31179.5 (3)
C1—C8—C9—C10178.3 (3)C29—C30—C31—C320.6 (6)
C8—C9—C10—C110.5 (5)C30—C31—C32—C331.7 (8)
C9—C10—C11—C120.7 (5)C31—C32—C33—C342.0 (7)
C10—C11—C12—C130.6 (5)C30—C29—C34—C330.2 (5)
C9—C8—C13—C120.0 (4)C22—C29—C34—C33179.8 (3)
C1—C8—C13—C12178.1 (3)C32—C33—C34—C291.3 (6)
C11—C12—C13—C80.2 (5)C22—O6—C35—O74.8 (4)
C1—O1—C14—O23.7 (4)C22—O6—C35—C36172.8 (2)
C1—O1—C14—C15175.6 (2)C37—N5—C36—C35135.1 (3)
C16—N1—C15—C14140.8 (3)C39—N5—C36—C3567.7 (4)
C18—N1—C15—C1472.1 (3)C37—N5—C36—C41102.5 (4)
C16—N1—C15—C2095.4 (3)C39—N5—C36—C4154.7 (4)
C18—N1—C15—C2051.6 (3)O7—C35—C36—N540.3 (4)
O2—C14—C15—N156.3 (4)O6—C35—C36—N5142.0 (2)
O1—C14—C15—N1124.3 (2)O7—C35—C36—C4181.2 (4)
O2—C14—C15—C2066.9 (3)O6—C35—C36—C4196.5 (3)
O1—C14—C15—C20112.5 (2)C36—N5—C37—O813.7 (6)
C15—N1—C16—O320.8 (5)C39—N5—C37—O8176.1 (4)
C18—N1—C16—O3175.5 (3)C36—N5—C37—C38166.5 (3)
C15—N1—C16—C17158.7 (3)C39—N5—C37—C384.1 (2)
C18—N1—C16—C174.0 (2)O8—C37—C38—C39176.3 (4)
O3—C16—C17—C18175.7 (4)N5—C37—C38—C393.9 (2)
N1—C16—C17—C183.8 (2)C37—N5—C39—C384.0 (2)
C16—N1—C18—C174.0 (2)C36—N5—C39—C38167.7 (3)
C15—N1—C18—C17159.9 (2)C37—N5—C39—S2111.8 (2)
C16—N1—C18—S1112.9 (2)C36—N5—C39—S251.9 (3)
C15—N1—C18—S143.1 (3)C37—C38—C39—N53.6 (2)
C16—C17—C18—N13.60 (19)C37—C38—C39—S2106.7 (2)
C16—C17—C18—S1110.4 (2)O10—S2—C39—N574.5 (2)
O5—S1—C18—N181.7 (2)O9—S2—C39—N5153.5 (2)
O4—S1—C18—N1147.9 (2)C40—S2—C39—N539.9 (2)
C19—S1—C18—N133.5 (2)O10—S2—C39—C3821.9 (3)
O5—S1—C18—C1717.1 (2)O9—S2—C39—C38110.1 (2)
O4—S1—C18—C17113.3 (2)C40—S2—C39—C38136.3 (2)
C19—S1—C18—C17132.2 (2)O10—S2—C40—C4164.0 (2)
O5—S1—C19—C2070.3 (2)O9—S2—C40—C41164.5 (2)
O4—S1—C19—C20158.96 (19)C39—S2—C40—C4149.8 (2)
C18—S1—C19—C2045.8 (2)N7—N6—C41—C4235.3 (5)
N3—N2—C20—C2159.9 (3)N7—N6—C41—C4086.7 (4)
N3—N2—C20—C1963.7 (3)N7—N6—C41—C36155.0 (3)
N3—N2—C20—C15178.4 (2)S2—C40—C41—N656.0 (3)
S1—C19—C20—N253.6 (3)S2—C40—C41—C42179.9 (2)
S1—C19—C20—C21177.84 (19)S2—C40—C41—C3656.8 (3)
S1—C19—C20—C1558.2 (3)N5—C36—C41—N668.6 (3)
N1—C15—C20—N264.9 (2)C35—C36—C41—N6169.3 (2)
C14—C15—C20—N2172.5 (2)N5—C36—C41—C42171.3 (2)
N1—C15—C20—C21176.8 (2)C35—C36—C41—C4249.2 (3)
C14—C15—C20—C2154.2 (3)N5—C36—C41—C4049.7 (3)
N1—C15—C20—C1953.7 (3)C35—C36—C41—C4072.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19—H19B···O3i0.972.443.364 (3)160
C31—H31···O9ii0.932.573.446 (6)157
C36—H36···O10iii0.982.253.196 (4)162
C40—H40B···O8iv0.972.293.235 (4)166
C18—H18···O7ii0.982.503.262 (3)135
Symmetry codes: (i) x+1/2, y+5/2, z+2; (ii) x, y+1, z; (iii) x+1, y+1/2, z+3/2; (iv) x+1, y1/2, z+3/2.
 

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