Diphenyl­methyl 3-azido-1,1-dioxocephalosporanate

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.

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

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

Crystal data

C21H20N4O5S	F(000) = 1840
Mr = 440.47	Dx = 1.375 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5653 reflections
a = 10.9030 (13) Å	θ = 2.4–21.8°
b = 11.3796 (14) Å	µ = 0.19 mm^−1
c = 34.293 (4) Å	T = 294 K
V = 4254.8 (9) Å^3	Block, colorless
Z = 8	0.24 × 0.22 × 0.18 mm

Data collection

Bruker SMART-1000 CCD area-detector diffractometer	7497 independent reflections
Radiation source: fine-focus sealed tube	5529 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→11
Tmin = 0.943, Tmax = 0.966	k = −9→13
20301 measured reflections	l = −40→40

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.092	w = 1/[σ^2(Fo^2) + (0.0408P)^2 + 0.1929P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
7497 reflections	Δρmax = 0.20 e Å^−3
561 parameters	Δρmin = −0.25 e Å^−3
18 restraints	Absolute structure: Flack (1983), 2607 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (6)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.89693 (6)	1.25811 (7)	0.94228 (2)	0.04747 (19)
S2	0.55483 (8)	−0.03894 (7)	0.81075 (2)	0.0574 (2)
O1	0.55441 (18)	0.93528 (15)	0.94762 (5)	0.0494 (5)
O2	0.7399 (2)	0.96878 (19)	0.92215 (7)	0.0768 (7)
O3	0.5002 (2)	1.35293 (18)	0.93499 (6)	0.0654 (6)
O4	1.00413 (17)	1.2272 (2)	0.92039 (6)	0.0680 (6)
O5	0.89415 (19)	1.36889 (17)	0.96202 (6)	0.0598 (5)
O6	0.77230 (18)	0.34298 (18)	0.76097 (6)	0.0633 (6)
O7	0.76923 (18)	0.23061 (17)	0.81479 (6)	0.0570 (5)
O8	0.3275 (2)	0.2679 (2)	0.78208 (9)	0.0982 (9)
O9	0.6129 (2)	−0.1087 (2)	0.84020 (7)	0.0894 (8)
O10	0.4463 (2)	−0.0812 (2)	0.79205 (8)	0.0855 (8)
N1	0.65556 (19)	1.21074 (18)	0.92983 (6)	0.0395 (5)
N2	0.6928 (2)	1.2520 (2)	1.00897 (6)	0.0454 (6)
N3	0.7504 (2)	1.2875 (2)	1.03751 (8)	0.0534 (6)
N4	0.7945 (3)	1.3314 (3)	1.06368 (9)	0.0885 (10)
N5	0.5199 (2)	0.18823 (19)	0.79781 (7)	0.0513 (6)
N6	0.5202 (3)	0.0705 (4)	0.72513 (9)	0.0992 (12)
N7	0.5239 (3)	0.0120 (3)	0.69639 (9)	0.0784 (9)
N8	0.5139 (4)	−0.0419 (4)	0.66900 (12)	0.1323 (16)
C1	0.5532 (3)	0.8129 (2)	0.93433 (8)	0.0462 (7)
H1	0.6199	0.8012	0.9156	0.055*
C2	0.5739 (3)	0.7347 (2)	0.96881 (8)	0.0464 (7)
C3	0.6661 (3)	0.6531 (3)	0.96900 (11)	0.0694 (10)
H3	0.7198	0.6488	0.9480	0.083*
C4	0.6804 (4)	0.5767 (3)	1.00012 (14)	0.0906 (13)
H4	0.7422	0.5204	0.9995	0.109*
C5	0.6052 (4)	0.5833 (3)	1.03134 (12)	0.0791 (11)
H5	0.6154	0.5322	1.0522	0.095*
C6	0.5146 (4)	0.6651 (3)	1.03207 (10)	0.0834 (12)
H6	0.4631	0.6702	1.0536	0.100*
C7	0.4983 (3)	0.7410 (3)	1.00097 (9)	0.0702 (9)
H7	0.4359	0.7966	1.0018	0.084*
C8	0.4319 (3)	0.7911 (2)	0.91417 (7)	0.0458 (7)
C9	0.3937 (3)	0.6768 (3)	0.90808 (9)	0.0660 (9)
H9	0.4414	0.6145	0.9170	0.079*
C10	0.2839 (4)	0.6545 (3)	0.88866 (11)	0.0782 (11)
H10	0.2583	0.5774	0.8848	0.094*
C11	0.2145 (3)	0.7443 (3)	0.87541 (9)	0.0692 (10)
H11	0.1417	0.7289	0.8622	0.083*
C12	0.2508 (3)	0.8575 (3)	0.88133 (9)	0.0659 (9)
H12	0.2024	0.9191	0.8724	0.079*
C13	0.3590 (3)	0.8806 (3)	0.90055 (9)	0.0567 (8)
H13	0.3832	0.9582	0.9044	0.068*
C14	0.6523 (3)	0.9998 (2)	0.94046 (8)	0.0432 (7)
C15	0.6405 (2)	1.1210 (2)	0.95915 (7)	0.0380 (6)
H15	0.5577	1.1281	0.9700	0.046*
C16	0.5968 (3)	1.3166 (2)	0.92411 (8)	0.0452 (7)
C17	0.7028 (3)	1.3631 (3)	0.89984 (9)	0.0543 (8)
H17A	0.7423	1.4323	0.9106	0.065*
H17B	0.6841	1.3732	0.8724	0.065*
C18	0.7674 (2)	1.2465 (3)	0.90976 (7)	0.0454 (7)
H18	0.7849	1.1986	0.8867	0.055*
C19	0.8662 (3)	1.1452 (2)	0.97667 (8)	0.0450 (7)
H19A	0.8858	1.0704	0.9646	0.054*
H19B	0.9214	1.1554	0.9986	0.054*
C20	0.7339 (3)	1.1381 (2)	0.99267 (7)	0.0412 (7)
C21	0.7241 (3)	1.0402 (2)	1.02283 (8)	0.0568 (8)
H21A	0.6414	1.0360	1.0324	0.085*
H21B	0.7788	1.0562	1.0441	0.085*
H21C	0.7459	0.9666	1.0110	0.085*
C22	0.8926 (3)	0.3910 (3)	0.77155 (9)	0.0569 (8)
H22	0.9459	0.3259	0.7794	0.068*
C23	0.9408 (3)	0.4414 (3)	0.73362 (9)	0.0529 (8)
C24	1.0167 (3)	0.3747 (3)	0.71039 (12)	0.0749 (10)
H24	1.0407	0.3006	0.7189	0.090*
C25	1.0576 (4)	0.4144 (4)	0.67501 (12)	0.0857 (12)
H25	1.1097	0.3679	0.6601	0.103*
C26	1.0221 (4)	0.5222 (4)	0.66163 (12)	0.0803 (12)
H26	1.0481	0.5486	0.6373	0.096*
C27	0.9477 (4)	0.5914 (3)	0.68437 (11)	0.0774 (10)
H27	0.9244	0.6656	0.6757	0.093*
C28	0.9074 (3)	0.5506 (3)	0.72008 (10)	0.0678 (9)
H28	0.8567	0.5978	0.7353	0.081*
C29	0.8796 (3)	0.4736 (3)	0.80542 (10)	0.0631 (9)
C30	0.7869 (4)	0.5561 (3)	0.80758 (13)	0.0868 (12)
H30	0.7299	0.5605	0.7875	0.104*
C31	0.7765 (5)	0.6323 (4)	0.83875 (18)	0.1135 (17)
H31	0.7134	0.6871	0.8401	0.136*
C32	0.8619 (7)	0.6240 (5)	0.86739 (18)	0.130 (2)
H32	0.8569	0.6763	0.8882	0.156*
C33	0.9535 (5)	0.5447 (5)	0.86759 (15)	0.1164 (17)
H33	1.0084	0.5407	0.8883	0.140*
C34	0.9636 (4)	0.4677 (4)	0.83550 (12)	0.0852 (12)
H34	1.0270	0.4131	0.8346	0.102*
C35	0.7251 (3)	0.2616 (3)	0.78476 (9)	0.0505 (7)
C36	0.6096 (3)	0.2096 (3)	0.76752 (8)	0.0540 (8)
H36	0.5751	0.2658	0.7488	0.065*
C37	0.3964 (3)	0.2088 (3)	0.80102 (10)	0.0656 (9)
C38	0.3869 (3)	0.1305 (3)	0.83643 (9)	0.0650 (9)
H38A	0.3329	0.0635	0.8331	0.078*
H38B	0.3698	0.1719	0.8605	0.078*
C39	0.5234 (3)	0.1032 (2)	0.82972 (8)	0.0499 (7)
H39	0.5767	0.1263	0.8514	0.060*
C40	0.6661 (3)	−0.0055 (3)	0.77482 (8)	0.0561 (8)
H40A	0.7418	0.0145	0.7881	0.067*
H40B	0.6816	−0.0764	0.7599	0.067*
C41	0.6375 (3)	0.0933 (3)	0.74590 (8)	0.0616 (9)
C42	0.7454 (3)	0.1063 (4)	0.71787 (9)	0.0867 (12)
H42A	0.7308	0.1714	0.7007	0.130*
H42B	0.7542	0.0357	0.7028	0.130*
H42C	0.8192	0.1201	0.7325	0.130*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0375 (4)	0.0612 (5)	0.0438 (4)	−0.0068 (3)	−0.0020 (3)	−0.0025 (4)
S2	0.0614 (5)	0.0450 (4)	0.0659 (5)	−0.0074 (4)	0.0016 (4)	−0.0008 (4)
O1	0.0512 (12)	0.0344 (10)	0.0627 (12)	−0.0080 (9)	0.0087 (10)	−0.0023 (9)
O2	0.0607 (15)	0.0714 (15)	0.0984 (18)	−0.0189 (12)	0.0257 (14)	−0.0375 (14)
O3	0.0494 (14)	0.0668 (14)	0.0799 (16)	0.0125 (11)	0.0106 (12)	0.0185 (12)
O4	0.0384 (12)	0.1104 (18)	0.0552 (12)	−0.0008 (12)	0.0058 (9)	−0.0059 (13)
O5	0.0644 (13)	0.0586 (13)	0.0564 (12)	−0.0186 (11)	−0.0054 (11)	−0.0044 (10)
O6	0.0481 (13)	0.0656 (13)	0.0763 (15)	−0.0155 (11)	−0.0167 (11)	0.0289 (12)
O7	0.0631 (13)	0.0605 (13)	0.0474 (12)	−0.0075 (11)	−0.0154 (10)	0.0099 (10)
O8	0.0546 (15)	0.0974 (19)	0.143 (2)	0.0033 (14)	−0.0043 (15)	0.0626 (19)
O9	0.0932 (18)	0.0683 (16)	0.1068 (19)	0.0199 (14)	0.0140 (16)	0.0441 (14)
O10	0.0674 (15)	0.0772 (16)	0.1118 (19)	−0.0289 (13)	0.0058 (15)	−0.0359 (14)
N1	0.0351 (13)	0.0449 (13)	0.0384 (12)	−0.0057 (11)	−0.0025 (10)	0.0036 (10)
N2	0.0513 (15)	0.0461 (14)	0.0387 (13)	0.0055 (12)	−0.0055 (11)	−0.0095 (12)
N3	0.0516 (16)	0.0526 (16)	0.0559 (16)	0.0045 (13)	−0.0030 (14)	−0.0080 (13)
N4	0.097 (2)	0.085 (2)	0.083 (2)	0.0178 (17)	−0.0390 (19)	−0.0403 (19)
N5	0.0500 (17)	0.0450 (14)	0.0590 (16)	−0.0056 (12)	−0.0007 (13)	0.0151 (12)
N6	0.076 (2)	0.166 (3)	0.0555 (19)	−0.017 (2)	−0.0229 (17)	−0.025 (2)
N7	0.089 (2)	0.089 (2)	0.058 (2)	−0.0279 (18)	−0.0310 (18)	0.0104 (17)
N8	0.165 (4)	0.135 (3)	0.097 (3)	−0.041 (3)	−0.050 (3)	−0.035 (3)
C1	0.0508 (17)	0.0346 (15)	0.0530 (17)	−0.0033 (13)	0.0050 (15)	−0.0028 (13)
C2	0.0487 (18)	0.0369 (15)	0.0537 (17)	−0.0050 (14)	−0.0040 (14)	−0.0032 (14)
C3	0.067 (2)	0.054 (2)	0.087 (3)	0.0108 (18)	0.011 (2)	0.0082 (19)
C4	0.083 (3)	0.068 (3)	0.121 (4)	0.012 (2)	−0.016 (3)	0.027 (3)
C5	0.096 (3)	0.065 (2)	0.076 (3)	−0.013 (2)	−0.027 (2)	0.018 (2)
C6	0.113 (3)	0.080 (3)	0.057 (2)	−0.003 (2)	0.006 (2)	0.010 (2)
C7	0.082 (2)	0.068 (2)	0.061 (2)	0.0154 (19)	0.0052 (18)	0.0082 (18)
C8	0.061 (2)	0.0412 (16)	0.0354 (15)	−0.0059 (15)	0.0038 (13)	0.0047 (12)
C9	0.085 (2)	0.0463 (19)	0.067 (2)	−0.0141 (17)	−0.020 (2)	0.0019 (16)
C10	0.096 (3)	0.061 (2)	0.078 (3)	−0.029 (2)	−0.017 (2)	−0.005 (2)
C11	0.067 (2)	0.089 (3)	0.0509 (19)	−0.028 (2)	−0.0051 (16)	0.003 (2)
C12	0.059 (2)	0.074 (2)	0.065 (2)	0.0026 (19)	0.0022 (19)	0.0107 (18)
C13	0.060 (2)	0.0471 (19)	0.063 (2)	−0.0082 (16)	0.0041 (17)	0.0059 (15)
C14	0.0448 (18)	0.0442 (16)	0.0407 (16)	−0.0065 (14)	−0.0013 (14)	−0.0011 (13)
C15	0.0334 (16)	0.0430 (16)	0.0375 (14)	−0.0030 (12)	0.0002 (12)	−0.0001 (12)
C16	0.0411 (18)	0.0531 (18)	0.0412 (16)	−0.0024 (15)	−0.0040 (15)	0.0052 (13)
C17	0.0508 (19)	0.0614 (19)	0.0508 (18)	−0.0028 (15)	−0.0029 (15)	0.0169 (15)
C18	0.0382 (16)	0.0616 (18)	0.0365 (14)	−0.0055 (15)	−0.0014 (12)	−0.0016 (14)
C19	0.0449 (18)	0.0473 (17)	0.0427 (16)	0.0037 (13)	−0.0109 (13)	−0.0060 (13)
C20	0.0501 (18)	0.0371 (16)	0.0364 (15)	0.0012 (13)	−0.0035 (13)	−0.0005 (12)
C21	0.070 (2)	0.0520 (18)	0.0485 (18)	0.0001 (16)	−0.0055 (16)	0.0117 (15)
C22	0.0404 (17)	0.0537 (19)	0.077 (2)	0.0000 (15)	−0.0083 (16)	0.0119 (17)
C23	0.0430 (18)	0.0492 (19)	0.066 (2)	−0.0100 (15)	−0.0042 (16)	0.0068 (16)
C24	0.063 (2)	0.060 (2)	0.102 (3)	0.0060 (18)	0.006 (2)	0.004 (2)
C25	0.071 (3)	0.093 (3)	0.093 (3)	−0.009 (2)	0.022 (2)	−0.006 (2)
C26	0.075 (3)	0.096 (3)	0.070 (2)	−0.041 (2)	0.004 (2)	−0.001 (2)
C27	0.085 (3)	0.066 (2)	0.081 (3)	−0.022 (2)	−0.002 (2)	0.016 (2)
C28	0.066 (2)	0.060 (2)	0.078 (2)	−0.0051 (18)	0.0057 (19)	0.0063 (18)
C29	0.054 (2)	0.061 (2)	0.074 (2)	−0.0137 (18)	0.0062 (19)	0.0103 (18)
C30	0.095 (3)	0.068 (2)	0.098 (3)	0.008 (2)	0.031 (2)	0.018 (2)
C31	0.132 (4)	0.081 (3)	0.128 (4)	0.004 (3)	0.060 (3)	0.012 (3)
C32	0.170 (6)	0.094 (4)	0.126 (4)	−0.064 (4)	0.065 (4)	−0.007 (3)
C33	0.117 (4)	0.137 (4)	0.095 (3)	−0.076 (4)	0.002 (3)	−0.003 (3)
C34	0.078 (3)	0.094 (3)	0.083 (3)	−0.041 (2)	−0.004 (2)	0.006 (2)
C35	0.0563 (19)	0.0469 (17)	0.0482 (18)	−0.0047 (15)	−0.0062 (15)	0.0108 (15)
C36	0.0510 (19)	0.063 (2)	0.0484 (17)	−0.0134 (16)	−0.0089 (15)	0.0188 (15)
C37	0.057 (2)	0.054 (2)	0.085 (2)	−0.0010 (17)	0.0055 (19)	0.0207 (18)
C38	0.069 (2)	0.058 (2)	0.068 (2)	−0.0003 (18)	0.0150 (18)	0.0084 (17)
C39	0.058 (2)	0.0480 (18)	0.0436 (16)	−0.0029 (15)	−0.0013 (15)	0.0029 (14)
C40	0.055 (2)	0.0579 (19)	0.0551 (19)	−0.0047 (16)	−0.0062 (16)	−0.0167 (15)
C41	0.049 (2)	0.102 (3)	0.0337 (16)	−0.0139 (18)	−0.0089 (14)	−0.0023 (17)
C42	0.072 (3)	0.142 (4)	0.046 (2)	−0.018 (2)	0.0099 (18)	−0.004 (2)

Geometric parameters (Å, º)

S1—O5	1.431 (2)	C15—C20	1.548 (4)
S1—O4	1.433 (2)	C15—H15	0.9800
S1—C19	1.776 (3)	C16—C17	1.519 (4)
S1—C18	1.804 (3)	C17—C18	1.541 (4)
S2—O10	1.429 (2)	C17—H17A	0.9700
S2—O9	1.432 (2)	C17—H17B	0.9700
S2—C40	1.771 (3)	C18—H18	0.9800
S2—C39	1.777 (3)	C19—C20	1.546 (4)
O1—C14	1.318 (3)	C19—H19A	0.9700
O1—C1	1.466 (3)	C19—H19B	0.9700
O2—C14	1.196 (3)	C20—C21	1.524 (4)
O3—C16	1.191 (3)	C21—H21A	0.9600
O6—C35	1.337 (3)	C21—H21B	0.9600
O6—C22	1.467 (3)	C21—H21C	0.9600
O7—C35	1.190 (3)	C22—C29	1.500 (4)
O8—C37	1.198 (4)	C22—C23	1.516 (4)
N1—C16	1.379 (3)	C22—H22	0.9800
N1—C15	1.443 (3)	C23—C28	1.375 (4)
N1—C18	1.458 (3)	C23—C24	1.377 (4)
N2—N3	1.231 (3)	C24—C25	1.369 (5)
N2—C20	1.481 (3)	C24—H24	0.9300
N3—N4	1.134 (3)	C25—C26	1.366 (5)
N5—C37	1.371 (4)	C25—H25	0.9300
N5—C36	1.447 (4)	C26—C27	1.373 (5)
N5—C39	1.461 (3)	C26—H26	0.9300
N6—N7	1.190 (4)	C27—C28	1.381 (4)
N6—C41	1.486 (4)	C27—H27	0.9300
N7—N8	1.127 (4)	C28—H28	0.9300
C1—C2	1.497 (4)	C29—C34	1.381 (5)
C1—C8	1.513 (4)	C29—C30	1.382 (5)
C1—H1	0.9800	C30—C31	1.381 (6)
C2—C3	1.369 (4)	C30—H30	0.9300
C2—C7	1.379 (4)	C31—C32	1.357 (7)
C3—C4	1.385 (5)	C31—H31	0.9300
C3—H3	0.9300	C32—C33	1.345 (7)
C4—C5	1.351 (6)	C32—H32	0.9300
C4—H4	0.9300	C33—C34	1.411 (6)
C5—C6	1.357 (5)	C33—H33	0.9300
C5—H5	0.9300	C34—H34	0.9300
C6—C7	1.384 (5)	C35—C36	1.512 (4)
C6—H6	0.9300	C36—C41	1.547 (4)
C7—H7	0.9300	C36—H36	0.9800
C8—C13	1.374 (4)	C37—C38	1.510 (4)
C8—C9	1.382 (4)	C38—C39	1.537 (4)
C9—C10	1.393 (5)	C38—H38A	0.9700
C9—H9	0.9300	C38—H38B	0.9700
C10—C11	1.351 (5)	C39—H39	0.9800
C10—H10	0.9300	C40—C41	1.531 (4)
C11—C12	1.362 (4)	C40—H40A	0.9700
C11—H11	0.9300	C40—H40B	0.9700
C12—C13	1.377 (4)	C41—C42	1.527 (4)
C12—H12	0.9300	C42—H42A	0.9600
C13—H13	0.9300	C42—H42B	0.9600
C14—C15	1.527 (4)	C42—H42C	0.9600
O5—S1—O4	118.78 (14)	N2—C20—C21	111.3 (2)
O5—S1—C19	108.60 (12)	N2—C20—C19	111.7 (2)
O4—S1—C19	108.91 (14)	C21—C20—C19	110.2 (2)
O5—S1—C18	109.91 (13)	N2—C20—C15	101.0 (2)
O4—S1—C18	107.25 (12)	C21—C20—C15	111.5 (2)
C19—S1—C18	102.11 (13)	C19—C20—C15	110.9 (2)
O10—S2—O9	119.75 (16)	C20—C21—H21A	109.5
O10—S2—C40	109.10 (15)	C20—C21—H21B	109.5
O9—S2—C40	107.88 (15)	H21A—C21—H21B	109.5
O10—S2—C39	108.11 (15)	C20—C21—H21C	109.5
O9—S2—C39	109.37 (15)	H21A—C21—H21C	109.5
C40—S2—C39	101.02 (14)	H21B—C21—H21C	109.5
C14—O1—C1	118.6 (2)	O6—C22—C29	109.9 (3)
C35—O6—C22	116.8 (2)	O6—C22—C23	103.8 (2)
C16—N1—C15	131.7 (2)	C29—C22—C23	117.4 (3)
C16—N1—C18	94.5 (2)	O6—C22—H22	108.5
C15—N1—C18	128.4 (2)	C29—C22—H22	108.5
N3—N2—C20	115.6 (2)	C23—C22—H22	108.5
N4—N3—N2	171.9 (3)	C28—C23—C24	117.5 (3)
C37—N5—C36	133.8 (3)	C28—C23—C22	122.7 (3)
C37—N5—C39	94.5 (2)	C24—C23—C22	119.7 (3)
C36—N5—C39	129.2 (2)	C25—C24—C23	121.7 (4)
N7—N6—C41	117.7 (3)	C25—C24—H24	119.1
N8—N7—N6	172.5 (5)	C23—C24—H24	119.1
O1—C1—C2	108.5 (2)	C26—C25—C24	120.1 (4)
O1—C1—C8	107.8 (2)	C26—C25—H25	119.9
C2—C1—C8	113.3 (2)	C24—C25—H25	119.9
O1—C1—H1	109.0	C25—C26—C27	119.4 (4)
C2—C1—H1	109.0	C25—C26—H26	120.3
C8—C1—H1	109.0	C27—C26—H26	120.3
C3—C2—C7	118.1 (3)	C26—C27—C28	119.9 (4)
C3—C2—C1	121.2 (3)	C26—C27—H27	120.0
C7—C2—C1	120.7 (3)	C28—C27—H27	120.0
C2—C3—C4	120.8 (4)	C23—C28—C27	121.2 (3)
C2—C3—H3	119.6	C23—C28—H28	119.4
C4—C3—H3	119.6	C27—C28—H28	119.4
C5—C4—C3	120.5 (4)	C34—C29—C30	118.5 (4)
C5—C4—H4	119.8	C34—C29—C22	119.1 (3)
C3—C4—H4	119.8	C30—C29—C22	122.4 (3)
C4—C5—C6	119.6 (4)	C31—C30—C29	121.9 (5)
C4—C5—H5	120.2	C31—C30—H30	119.1
C6—C5—H5	120.2	C29—C30—H30	119.1
C5—C6—C7	120.5 (4)	C32—C31—C30	117.4 (5)
C5—C6—H6	119.8	C32—C31—H31	121.3
C7—C6—H6	119.8	C30—C31—H31	121.3
C2—C7—C6	120.5 (3)	C33—C32—C31	124.0 (6)
C2—C7—H7	119.8	C33—C32—H32	118.0
C6—C7—H7	119.8	C31—C32—H32	118.0
C13—C8—C9	118.2 (3)	C32—C33—C34	118.1 (5)
C13—C8—C1	122.6 (2)	C32—C33—H33	121.0
C9—C8—C1	119.2 (3)	C34—C33—H33	121.0
C8—C9—C10	120.2 (3)	C29—C34—C33	120.1 (4)
C8—C9—H9	119.9	C29—C34—H34	120.0
C10—C9—H9	119.9	C33—C34—H34	120.0
C11—C10—C9	120.3 (3)	O7—C35—O6	125.3 (3)
C11—C10—H10	119.8	O7—C35—C36	124.0 (3)
C9—C10—H10	119.8	O6—C35—C36	110.7 (2)
C10—C11—C12	120.1 (3)	N5—C36—C35	110.4 (2)
C10—C11—H11	119.9	N5—C36—C41	109.5 (2)
C12—C11—H11	119.9	C35—C36—C41	111.0 (2)
C11—C12—C13	120.1 (3)	N5—C36—H36	108.7
C11—C12—H12	120.0	C35—C36—H36	108.7
C13—C12—H12	120.0	C41—C36—H36	108.7
C8—C13—C12	121.1 (3)	O8—C37—N5	131.9 (3)
C8—C13—H13	119.5	O8—C37—C38	136.4 (3)
C12—C13—H13	119.5	N5—C37—C38	91.7 (3)
O2—C14—O1	125.5 (2)	C37—C38—C39	86.1 (2)
O2—C14—C15	123.6 (3)	C37—C38—H38A	114.3
O1—C14—C15	110.9 (2)	C39—C38—H38A	114.3
N1—C15—C14	109.7 (2)	C37—C38—H38B	114.3
N1—C15—C20	110.7 (2)	C39—C38—H38B	114.3
C14—C15—C20	111.7 (2)	H38A—C38—H38B	111.4
N1—C15—H15	108.2	N5—C39—C38	87.3 (2)
C14—C15—H15	108.2	N5—C39—S2	109.48 (19)
C20—C15—H15	108.2	C38—C39—S2	115.1 (2)
O3—C16—N1	132.0 (3)	N5—C39—H39	114.0
O3—C16—C17	136.3 (3)	C38—C39—H39	114.0
N1—C16—C17	91.6 (2)	S2—C39—H39	114.0
C16—C17—C18	85.8 (2)	C41—C40—S2	118.0 (2)
C16—C17—H17A	114.3	C41—C40—H40A	107.8
C18—C17—H17A	114.3	S2—C40—H40A	107.8
C16—C17—H17B	114.3	C41—C40—H40B	107.8
C18—C17—H17B	114.3	S2—C40—H40B	107.8
H17A—C17—H17B	111.5	H40A—C40—H40B	107.1
N1—C18—C17	87.8 (2)	N6—C41—C42	112.2 (2)
N1—C18—S1	112.54 (17)	N6—C41—C40	111.0 (3)
C17—C18—S1	115.5 (2)	C42—C41—C40	108.8 (3)
N1—C18—H18	112.9	N6—C41—C36	102.1 (3)
C17—C18—H18	112.9	C42—C41—C36	111.7 (3)
S1—C18—H18	112.9	C40—C41—C36	111.0 (2)
C20—C19—S1	116.75 (19)	C41—C42—H42A	109.5
C20—C19—H19A	108.1	C41—C42—H42B	109.5
S1—C19—H19A	108.1	H42A—C42—H42B	109.5
C20—C19—H19B	108.1	C41—C42—H42C	109.5
S1—C19—H19B	108.1	H42A—C42—H42C	109.5
H19A—C19—H19B	107.3	H42B—C42—H42C	109.5
C20—N2—N3—N4	180 (100)	C14—C15—C20—C19	68.9 (3)
C41—N6—N7—N8	179 (100)	C35—O6—C22—C29	−74.2 (3)
C14—O1—C1—C2	104.2 (3)	C35—O6—C22—C23	159.4 (3)
C14—O1—C1—C8	−132.8 (2)	O6—C22—C23—C28	82.1 (3)
O1—C1—C2—C3	−125.6 (3)	C29—C22—C23—C28	−39.4 (4)
C8—C1—C2—C3	114.7 (3)	O6—C22—C23—C24	−94.8 (3)
O1—C1—C2—C7	56.1 (4)	C29—C22—C23—C24	143.7 (3)
C8—C1—C2—C7	−63.7 (3)	C28—C23—C24—C25	−0.2 (5)
C7—C2—C3—C4	2.0 (5)	C22—C23—C24—C25	176.8 (3)
C1—C2—C3—C4	−176.4 (3)	C23—C24—C25—C26	−0.9 (6)
C2—C3—C4—C5	−1.6 (6)	C24—C25—C26—C27	1.6 (6)
C3—C4—C5—C6	0.4 (6)	C25—C26—C27—C28	−1.3 (5)
C4—C5—C6—C7	0.5 (6)	C24—C23—C28—C27	0.5 (5)
C3—C2—C7—C6	−1.1 (5)	C22—C23—C28—C27	−176.4 (3)
C1—C2—C7—C6	177.2 (3)	C26—C27—C28—C23	0.3 (5)
C5—C6—C7—C2	−0.1 (6)	O6—C22—C29—C34	136.3 (3)
O1—C1—C8—C13	18.8 (3)	C23—C22—C29—C34	−105.4 (3)
C2—C1—C8—C13	138.9 (3)	O6—C22—C29—C30	−44.1 (4)
O1—C1—C8—C9	−163.0 (3)	C23—C22—C29—C30	74.2 (4)
C2—C1—C8—C9	−42.9 (4)	C34—C29—C30—C31	0.1 (5)
C13—C8—C9—C10	−0.1 (5)	C22—C29—C30—C31	−179.5 (3)
C1—C8—C9—C10	−178.3 (3)	C29—C30—C31—C32	0.6 (6)
C8—C9—C10—C11	0.5 (5)	C30—C31—C32—C33	−1.7 (8)
C9—C10—C11—C12	−0.7 (5)	C31—C32—C33—C34	2.0 (7)
C10—C11—C12—C13	0.6 (5)	C30—C29—C34—C33	0.2 (5)
C9—C8—C13—C12	0.0 (4)	C22—C29—C34—C33	179.8 (3)
C1—C8—C13—C12	178.1 (3)	C32—C33—C34—C29	−1.3 (6)
C11—C12—C13—C8	−0.2 (5)	C22—O6—C35—O7	4.8 (4)
C1—O1—C14—O2	3.7 (4)	C22—O6—C35—C36	−172.8 (2)
C1—O1—C14—C15	−175.6 (2)	C37—N5—C36—C35	135.1 (3)
C16—N1—C15—C14	140.8 (3)	C39—N5—C36—C35	−67.7 (4)
C18—N1—C15—C14	−72.1 (3)	C37—N5—C36—C41	−102.5 (4)
C16—N1—C15—C20	−95.4 (3)	C39—N5—C36—C41	54.7 (4)
C18—N1—C15—C20	51.6 (3)	O7—C35—C36—N5	40.3 (4)
O2—C14—C15—N1	56.3 (4)	O6—C35—C36—N5	−142.0 (2)
O1—C14—C15—N1	−124.3 (2)	O7—C35—C36—C41	−81.2 (4)
O2—C14—C15—C20	−66.9 (3)	O6—C35—C36—C41	96.5 (3)
O1—C14—C15—C20	112.5 (2)	C36—N5—C37—O8	−13.7 (6)
C15—N1—C16—O3	−20.8 (5)	C39—N5—C37—O8	−176.1 (4)
C18—N1—C16—O3	−175.5 (3)	C36—N5—C37—C38	166.5 (3)
C15—N1—C16—C17	158.7 (3)	C39—N5—C37—C38	4.1 (2)
C18—N1—C16—C17	4.0 (2)	O8—C37—C38—C39	176.3 (4)
O3—C16—C17—C18	175.7 (4)	N5—C37—C38—C39	−3.9 (2)
N1—C16—C17—C18	−3.8 (2)	C37—N5—C39—C38	−4.0 (2)
C16—N1—C18—C17	−4.0 (2)	C36—N5—C39—C38	−167.7 (3)
C15—N1—C18—C17	−159.9 (2)	C37—N5—C39—S2	111.8 (2)
C16—N1—C18—S1	112.9 (2)	C36—N5—C39—S2	−51.9 (3)
C15—N1—C18—S1	−43.1 (3)	C37—C38—C39—N5	3.6 (2)
C16—C17—C18—N1	3.60 (19)	C37—C38—C39—S2	−106.7 (2)
C16—C17—C18—S1	−110.4 (2)	O10—S2—C39—N5	−74.5 (2)
O5—S1—C18—N1	−81.7 (2)	O9—S2—C39—N5	153.5 (2)
O4—S1—C18—N1	147.9 (2)	C40—S2—C39—N5	39.9 (2)
C19—S1—C18—N1	33.5 (2)	O10—S2—C39—C38	21.9 (3)
O5—S1—C18—C17	17.1 (2)	O9—S2—C39—C38	−110.1 (2)
O4—S1—C18—C17	−113.3 (2)	C40—S2—C39—C38	136.3 (2)
C19—S1—C18—C17	132.2 (2)	O10—S2—C40—C41	64.0 (2)
O5—S1—C19—C20	70.3 (2)	O9—S2—C40—C41	−164.5 (2)
O4—S1—C19—C20	−158.96 (19)	C39—S2—C40—C41	−49.8 (2)
C18—S1—C19—C20	−45.8 (2)	N7—N6—C41—C42	35.3 (5)
N3—N2—C20—C21	59.9 (3)	N7—N6—C41—C40	−86.7 (4)
N3—N2—C20—C19	−63.7 (3)	N7—N6—C41—C36	155.0 (3)
N3—N2—C20—C15	178.4 (2)	S2—C40—C41—N6	−56.0 (3)
S1—C19—C20—N2	−53.6 (3)	S2—C40—C41—C42	−179.9 (2)
S1—C19—C20—C21	−177.84 (19)	S2—C40—C41—C36	56.8 (3)
S1—C19—C20—C15	58.2 (3)	N5—C36—C41—N6	68.6 (3)
N1—C15—C20—N2	64.9 (2)	C35—C36—C41—N6	−169.3 (2)
C14—C15—C20—N2	−172.5 (2)	N5—C36—C41—C42	−171.3 (2)
N1—C15—C20—C21	−176.8 (2)	C35—C36—C41—C42	−49.2 (3)
C14—C15—C20—C21	−54.2 (3)	N5—C36—C41—C40	−49.7 (3)
N1—C15—C20—C19	−53.7 (3)	C35—C36—C41—C40	72.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19B···O3^i	0.97	2.44	3.364 (3)	160
C31—H31···O9^ii	0.93	2.57	3.446 (6)	157
C36—H36···O10^iii	0.98	2.25	3.196 (4)	162
C40—H40B···O8^iv	0.97	2.29	3.235 (4)	166
C18—H18···O7^ii	0.98	2.50	3.262 (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, y−1/2, −z+3/2.