Crystal structure and Hirshfeld surface analysis of 10-hy­droxy-2-(4-meth­oxy­phen­yl)-3-oxo-2,3,3a,4,10,10a-hexa­hydro-1H-9-thia-2-aza­cyclo­penta­[b]fluorene-4-carb­oxy­lic acid dimethyl sulfoxide-d₆ monosolvate

In the crystal, mol­ecules are connected by pairs of inter­molecular C—H...O hydrogen bonds, forming dimers with (8) motifs. These dimers form a three-dimensional network through O—H...O, O—H...S and C—H...O hydrogen bonds with each other directly and through solvent mol­ecules.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.049
• wR factor = 0.129
• Data-to-parameter ratio = 20.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT910_ALERT_3_B Missing # of FCF Reflection(s) Below Theta(Min).         18 Note

Author Response: This is probably due to beam-stop. By using Mo radiation and the geometry of our goniometer, this happens quite often.

Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.966 Check

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         12 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         12 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          3 Report
PLAT168_ALERT_4_G The CIF-Embedded .res File Contains EXYZ Records          1 Report
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          2 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          5 Report
PLAT230_ALERT_2_G Hirshfeld Test Diff for    O5A      --C4B      .        6.4 s.u.
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )         7% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  2  )       100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  3  )       100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  2  )       8.90 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  3  )       1.10 Check
PLAT367_ALERT_2_G Long?  C(sp?)-C(sp?) Bond  C3       - C3A      .       1.53 Ang.
PLAT367_ALERT_2_G Long?  C(sp?)-C(sp?) Bond  C3A      - C10A     .       1.52 Ang.
PLAT413_ALERT_2_G Short Inter XH3 .. XHn     H8A      ..D19E     .       2.04 Ang.
                                                    x,1+y,z  =      1_565 Check
PLAT415_ALERT_2_G Short Inter D-H..H-X       H17A     ..H5B      .       2.03 Ang.
                                             x,3/2-y,-1/2+z  =      4_575 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  S1B      ..C8       .       3.27 Ang.
                                            -x,-1/2+y,1/2-z  =      2_545 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  O5B      ..C18      .       2.92 Ang.
                                                1-x,1-y,1-z  =      3_666 Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          1 Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         15 Note
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          1 Note
PLAT967_ALERT_5_G Note: Two-Theta Cutoff Value in Embedded .res ..       60.0 Degree
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         17 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  25 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   9 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

---

Computing details

10-Hydroxy-2-(4-methoxyphenyl)-3-oxo-2,3,3a,4,10,10a-hexahydro-1H-9-thia-2-azacyclopenta[b]fluorene-4-carboxylic acid dimethyl sulfoxide-d₆ monosolvate

Crystal data

C22H19NO5S·C2D6OS	F(000) = 1024
Mr = 493.61	Dx = 1.460 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.3178 (4) Å	Cell parameters from 9765 reflections
b = 9.2747 (2) Å	θ = 2.6–30.1°
c = 14.8720 (4) Å	µ = 0.28 mm^−1
β = 93.771 (1)°	T = 100 K
V = 2245.89 (10) Å^3	Fragment, colourless
Z = 4	0.40 × 0.28 × 0.22 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer	5693 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.032
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θmax = 30.0°, θmin = 4.2°
Tmin = 0.847, Tmax = 0.941	h = −22→22
69078 measured reflections	k = −13→13
6531 independent reflections	l = −20→20

Refinement

Refinement on F^2	15 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.129	w = 1/[σ^2(Fo^2) + (0.0518P)^2 + 1.8241P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max = 0.001
6531 reflections	Δρmax = 0.54 e Å^−3
324 parameters	Δρmin = −0.47 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1A	0.06873 (3)	0.67027 (5)	0.20351 (4)	0.03201 (16)	0.8903 (18)
S1B	−0.0094 (3)	0.7350 (5)	0.2022 (3)	0.0386 (13)*	0.1097 (18)
S5	0.21789 (3)	1.16195 (5)	0.65744 (3)	0.03355 (13)
O1	0.36715 (8)	0.72156 (13)	0.33936 (8)	0.0253 (3)
O2	0.14801 (9)	0.83115 (17)	0.39946 (10)	0.0367 (3)
O3	0.20598 (9)	0.93552 (15)	0.28380 (8)	0.0338 (3)
H3	0.165707	0.899140	0.253855	0.041*
O4	0.47133 (8)	0.05607 (13)	0.38739 (8)	0.0275 (3)
O5A	0.25163 (15)	0.8579 (2)	0.70428 (13)	0.0338 (6)	0.637 (4)
H5A	0.283755	0.813423	0.741012	0.041*	0.637 (4)
O5B	0.3604 (2)	0.9025 (4)	0.6728 (2)	0.0282 (9)	0.363 (4)
H5B	0.358402	0.867406	0.724666	0.034*	0.363 (4)
O6A	0.08659 (10)	0.82728 (16)	0.18542 (11)	0.0337 (4)	0.8903 (18)
O6B	0.0447 (10)	0.8676 (13)	0.2106 (10)	0.044 (3)*	0.1097 (18)
N2	0.35684 (8)	0.60178 (14)	0.47516 (9)	0.0193 (3)
C1	0.35193 (10)	0.71814 (17)	0.41916 (10)	0.0193 (3)
C3A	0.29022 (10)	0.77925 (18)	0.55483 (10)	0.0218 (3)
H3AA	0.232017	0.752657	0.536985	0.026*
C3	0.34047 (11)	0.64061 (18)	0.56878 (10)	0.0231 (3)
H3A	0.392113	0.658285	0.605867	0.028*
H3B	0.308591	0.564525	0.597492	0.028*
C4B	0.29054 (12)	0.8898 (2)	0.63036 (11)	0.0302 (4)	0.637 (4)
H4A	0.349158	0.910797	0.649808	0.036*	0.637 (4)
C4C	0.29054 (12)	0.8898 (2)	0.63036 (11)	0.0302 (4)	0.363 (4)
H4B	0.251734	0.853878	0.674610	0.036*	0.363 (4)
C4A	0.25370 (11)	1.02578 (19)	0.58966 (11)	0.0258 (3)
C5A	0.19138 (11)	1.26951 (19)	0.56388 (11)	0.0264 (3)
C6	0.15675 (13)	1.4072 (2)	0.56345 (14)	0.0338 (4)
H6A	0.143922	1.452519	0.618055	0.041*
C7	0.14169 (12)	1.4755 (2)	0.48199 (14)	0.0331 (4)
H7A	0.117404	1.568665	0.480419	0.040*
C8	0.16150 (12)	1.41029 (19)	0.40123 (13)	0.0295 (4)
H8A	0.151707	1.460284	0.345810	0.035*
C9B	0.24595 (10)	1.06021 (17)	0.50055 (10)	0.0204 (3)
C9A	0.21054 (10)	1.20072 (17)	0.48381 (11)	0.0213 (3)
C9	0.19531 (10)	1.27320 (18)	0.40184 (11)	0.0238 (3)
H9A	0.208082	1.228670	0.346961	0.029*
C10A	0.32805 (9)	0.84675 (16)	0.47404 (10)	0.0187 (3)
H10A	0.380248	0.894315	0.497193	0.022*
C10	0.27474 (9)	0.96355 (16)	0.42751 (10)	0.0184 (3)
H10B	0.309492	1.021507	0.387981	0.022*
C11	0.20217 (10)	0.90191 (17)	0.36979 (11)	0.0216 (3)
C12	0.38481 (9)	0.46286 (16)	0.45148 (10)	0.0189 (3)
C13	0.42078 (10)	0.37136 (18)	0.51699 (11)	0.0218 (3)
H13A	0.426719	0.402232	0.577975	0.026*
C14	0.44797 (10)	0.23566 (18)	0.49391 (11)	0.0224 (3)
H14A	0.471177	0.173102	0.539320	0.027*
C15	0.44140 (10)	0.19057 (16)	0.40438 (11)	0.0206 (3)
C16	0.40420 (10)	0.28012 (17)	0.33900 (11)	0.0227 (3)
H16A	0.398353	0.249190	0.278021	0.027*
C17	0.37553 (10)	0.41479 (17)	0.36268 (10)	0.0214 (3)
H17A	0.349271	0.474921	0.317799	0.026*
C18	0.46796 (13)	0.0111 (2)	0.29506 (13)	0.0319 (4)
H18A	0.490909	−0.086181	0.291209	0.048*
H18B	0.410733	0.010725	0.270532	0.048*
H18C	0.499947	0.078007	0.260286	0.048*
C19A	0.02185 (17)	0.6061 (3)	0.0999 (2)	0.0471 (7)	0.8903 (18)
D19A	0.008139	0.503811	0.105923	0.071*	0.8903 (18)
D19B	−0.028387	0.661165	0.084572	0.071*	0.8903 (18)
D19C	0.059929	0.617892	0.052192	0.071*	0.8903 (18)
C20A	−0.01808 (16)	0.6679 (3)	0.26878 (19)	0.0470 (6)	0.8903 (18)
D20A	−0.032251	0.567942	0.282401	0.070*	0.8903 (18)
D20B	−0.005525	0.720540	0.325154	0.070*	0.8903 (18)
D20C	−0.064553	0.713967	0.234952	0.070*	0.8903 (18)
C19B	0.0423 (13)	0.6018 (18)	0.2686 (12)	0.049 (4)*	0.1097 (18)
D19D	0.010074	0.512543	0.265939	0.074*	0.1097 (18)
D19E	0.096287	0.583660	0.245646	0.074*	0.1097 (18)
D19F	0.049335	0.635024	0.331200	0.074*	0.1097 (18)
C20B	0.0041 (16)	0.666 (2)	0.0930 (9)	0.049 (4)*	0.1097 (18)
D20D	−0.029537	0.579159	0.082990	0.074*	0.1097 (18)
D20E	−0.012775	0.738825	0.047762	0.074*	0.1097 (18)
D20F	0.062047	0.641717	0.087819	0.074*	0.1097 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0229 (2)	0.0222 (2)	0.0503 (3)	−0.00093 (17)	−0.0028 (2)	0.0081 (2)
S5	0.0489 (3)	0.0338 (2)	0.01792 (19)	0.0139 (2)	0.00149 (17)	−0.00626 (16)
O1	0.0395 (7)	0.0201 (5)	0.0168 (5)	0.0014 (5)	0.0053 (5)	−0.0001 (4)
O2	0.0332 (7)	0.0444 (8)	0.0314 (7)	−0.0135 (6)	−0.0070 (6)	0.0084 (6)
O3	0.0458 (8)	0.0352 (7)	0.0188 (6)	−0.0119 (6)	−0.0097 (5)	0.0031 (5)
O4	0.0368 (7)	0.0202 (6)	0.0260 (6)	0.0073 (5)	0.0066 (5)	0.0023 (4)
O5A	0.0472 (13)	0.0372 (12)	0.0179 (9)	0.0081 (9)	0.0094 (8)	0.0081 (8)
O5B	0.0288 (18)	0.036 (2)	0.0193 (16)	−0.0038 (14)	−0.0041 (12)	−0.0009 (13)
O6A	0.0408 (9)	0.0232 (7)	0.0346 (8)	−0.0094 (6)	−0.0158 (7)	0.0074 (6)
N2	0.0236 (6)	0.0192 (6)	0.0149 (5)	0.0026 (5)	−0.0004 (5)	0.0004 (5)
C1	0.0218 (7)	0.0183 (7)	0.0174 (6)	0.0003 (5)	−0.0009 (5)	−0.0003 (5)
C3A	0.0264 (7)	0.0258 (7)	0.0131 (6)	0.0056 (6)	0.0004 (5)	0.0014 (5)
C3	0.0288 (8)	0.0258 (8)	0.0146 (6)	0.0067 (6)	0.0007 (6)	0.0018 (6)
C4B	0.0406 (10)	0.0370 (9)	0.0127 (7)	0.0155 (8)	−0.0008 (6)	−0.0016 (6)
C4C	0.0406 (10)	0.0370 (9)	0.0127 (7)	0.0155 (8)	−0.0008 (6)	−0.0016 (6)
C4A	0.0320 (8)	0.0278 (8)	0.0172 (7)	0.0080 (7)	−0.0010 (6)	−0.0045 (6)
C5A	0.0312 (8)	0.0256 (8)	0.0222 (7)	0.0038 (7)	0.0006 (6)	−0.0037 (6)
C6	0.0391 (10)	0.0281 (9)	0.0345 (10)	0.0060 (8)	0.0054 (8)	−0.0086 (7)
C7	0.0355 (9)	0.0217 (8)	0.0424 (11)	0.0042 (7)	0.0044 (8)	−0.0021 (7)
C8	0.0324 (9)	0.0221 (8)	0.0337 (9)	0.0021 (7)	0.0005 (7)	0.0032 (7)
C9B	0.0212 (7)	0.0220 (7)	0.0179 (7)	0.0023 (6)	−0.0005 (5)	−0.0041 (5)
C9A	0.0196 (7)	0.0221 (7)	0.0218 (7)	0.0002 (5)	−0.0009 (5)	−0.0037 (6)
C9	0.0249 (7)	0.0215 (7)	0.0249 (8)	0.0006 (6)	0.0014 (6)	−0.0008 (6)
C10A	0.0212 (7)	0.0193 (7)	0.0153 (6)	0.0022 (5)	−0.0004 (5)	−0.0011 (5)
C10	0.0213 (7)	0.0192 (7)	0.0144 (6)	0.0011 (5)	−0.0015 (5)	−0.0012 (5)
C11	0.0248 (7)	0.0186 (7)	0.0205 (7)	0.0014 (6)	−0.0047 (6)	−0.0001 (5)
C12	0.0187 (6)	0.0182 (7)	0.0196 (7)	0.0002 (5)	−0.0009 (5)	0.0014 (5)
C13	0.0233 (7)	0.0239 (7)	0.0177 (7)	0.0020 (6)	−0.0023 (5)	0.0015 (6)
C14	0.0217 (7)	0.0228 (7)	0.0224 (7)	0.0036 (6)	−0.0015 (6)	0.0049 (6)
C15	0.0197 (7)	0.0176 (7)	0.0248 (7)	0.0006 (5)	0.0033 (6)	0.0018 (6)
C16	0.0289 (8)	0.0196 (7)	0.0195 (7)	−0.0010 (6)	0.0013 (6)	0.0004 (6)
C17	0.0261 (7)	0.0186 (7)	0.0188 (7)	0.0000 (6)	−0.0026 (6)	0.0018 (5)
C18	0.0453 (11)	0.0226 (8)	0.0289 (9)	0.0050 (7)	0.0111 (8)	−0.0007 (7)
C19A	0.0414 (14)	0.0399 (14)	0.0605 (17)	−0.0108 (11)	0.0066 (12)	−0.0198 (12)
C20A	0.0358 (12)	0.0560 (16)	0.0497 (15)	−0.0034 (11)	0.0075 (11)	0.0072 (12)

Geometric parameters (Å, º)

S1A—O6A	1.5127 (15)	C7—C8	1.401 (3)
S1A—C20A	1.769 (3)	C7—H7A	0.9500
S1A—C19A	1.777 (3)	C8—C9	1.386 (2)
S1B—O6B	1.515 (12)	C8—H8A	0.9500
S1B—C19B	1.762 (12)	C9B—C9A	1.441 (2)
S1B—C20B	1.774 (13)	C9B—C10	1.507 (2)
S5—C4A	1.7407 (17)	C9A—C9	1.400 (2)
S5—C5A	1.7434 (18)	C9—H9A	0.9500
O1—C1	1.2288 (19)	C10A—C10	1.526 (2)
O2—C11	1.207 (2)	C10A—H10A	1.0000
O3—C11	1.322 (2)	C10—C11	1.527 (2)
O3—H3	0.8400	C10—H10B	1.0000
O4—C15	1.3692 (19)	C12—C13	1.392 (2)
O4—C18	1.433 (2)	C12—C17	1.393 (2)
O5A—C4B	1.338 (3)	C13—C14	1.385 (2)
O5A—H5A	0.8400	C13—H13A	0.9500
O5B—C4C	1.271 (4)	C14—C15	1.393 (2)
O5B—H5B	0.8400	C14—H14A	0.9500
N2—C1	1.362 (2)	C15—C16	1.388 (2)
N2—C12	1.419 (2)	C16—C17	1.387 (2)
N2—C3	1.479 (2)	C16—H16A	0.9500
C1—C10A	1.511 (2)	C17—H17A	0.9500
C3A—C4C	1.521 (2)	C18—H18A	0.9800
C3A—C4B	1.521 (2)	C18—H18B	0.9800
C3A—C10A	1.521 (2)	C18—H18C	0.9800
C3A—C3	1.532 (2)	C19A—D19A	0.9800
C3A—H3AA	1.0000	C19A—D19B	0.9800
C3—H3A	0.9900	C19A—D19C	0.9800
C3—H3B	0.9900	C20A—D20A	0.9800
C4B—C4A	1.507 (2)	C20A—D20B	0.9800
C4B—H4A	1.0000	C20A—D20C	0.9800
C4C—C4A	1.507 (2)	C19B—D19D	0.9800
C4C—H4B	1.0000	C19B—D19E	0.9800
C4A—C9B	1.361 (2)	C19B—D19F	0.9800
C5A—C6	1.396 (3)	C20B—D20D	0.9800
C5A—C9A	1.404 (2)	C20B—D20E	0.9800
C6—C7	1.375 (3)	C20B—D20F	0.9800
C6—H6A	0.9500
O6A—S1A—C20A	106.26 (13)	C8—C9—C9A	119.61 (16)
O6A—S1A—C19A	104.20 (12)	C8—C9—H9A	120.2
C20A—S1A—C19A	99.03 (13)	C9A—C9—H9A	120.2
O6B—S1B—C19B	105.6 (8)	C1—C10A—C3A	103.55 (12)
O6B—S1B—C20B	105.2 (8)	C1—C10A—C10	118.36 (12)
C19B—S1B—C20B	100.2 (9)	C3A—C10A—C10	113.66 (13)
C4A—S5—C5A	91.61 (8)	C1—C10A—H10A	106.9
C11—O3—H3	109.5	C3A—C10A—H10A	106.9
C15—O4—C18	116.77 (13)	C10—C10A—H10A	106.9
C4B—O5A—H5A	109.5	C9B—C10—C10A	106.90 (12)
C4C—O5B—H5B	109.5	C9B—C10—C11	111.15 (13)
C1—N2—C12	125.06 (13)	C10A—C10—C11	112.76 (13)
C1—N2—C3	112.06 (13)	C9B—C10—H10B	108.6
C12—N2—C3	122.38 (13)	C10A—C10—H10B	108.6
O1—C1—N2	127.11 (15)	C11—C10—H10B	108.6
O1—C1—C10A	125.25 (14)	O2—C11—O3	124.33 (15)
N2—C1—C10A	107.58 (13)	O2—C11—C10	123.87 (15)
C4C—C3A—C10A	108.91 (14)	O3—C11—C10	111.81 (14)
C4B—C3A—C10A	108.91 (14)	C13—C12—C17	118.87 (14)
C4C—C3A—C3	119.35 (13)	C13—C12—N2	120.50 (14)
C4B—C3A—C3	119.35 (13)	C17—C12—N2	120.62 (13)
C10A—C3A—C3	102.18 (12)	C14—C13—C12	120.51 (15)
C4B—C3A—H3AA	108.6	C14—C13—H13A	119.7
C10A—C3A—H3AA	108.6	C12—C13—H13A	119.7
C3—C3A—H3AA	108.6	C13—C14—C15	120.25 (14)
N2—C3—C3A	101.83 (12)	C13—C14—H14A	119.9
N2—C3—H3A	111.4	C15—C14—H14A	119.9
C3A—C3—H3A	111.4	O4—C15—C16	124.11 (15)
N2—C3—H3B	111.4	O4—C15—C14	116.36 (14)
C3A—C3—H3B	111.4	C16—C15—C14	119.51 (14)
H3A—C3—H3B	109.3	C17—C16—C15	120.02 (15)
O5A—C4B—C4A	108.46 (16)	C17—C16—H16A	120.0
O5A—C4B—C3A	118.61 (19)	C15—C16—H16A	120.0
C4A—C4B—C3A	106.60 (13)	C16—C17—C12	120.76 (14)
O5A—C4B—H4A	107.6	C16—C17—H17A	119.6
C4A—C4B—H4A	107.6	C12—C17—H17A	119.6
C3A—C4B—H4A	107.6	O4—C18—H18A	109.5
O5B—C4C—C4A	116.3 (2)	O4—C18—H18B	109.5
O5B—C4C—C3A	112.9 (2)	H18A—C18—H18B	109.5
C4A—C4C—C3A	106.60 (13)	O4—C18—H18C	109.5
O5B—C4C—H4B	106.9	H18A—C18—H18C	109.5
C4A—C4C—H4B	106.9	H18B—C18—H18C	109.5
C3A—C4C—H4B	106.9	S1A—C19A—D19A	109.5
C9B—C4A—C4C	126.63 (15)	S1A—C19A—D19B	109.5
C9B—C4A—C4B	126.63 (15)	D19A—C19A—D19B	109.5
C9B—C4A—S5	112.36 (13)	S1A—C19A—D19C	109.5
C4C—C4A—S5	120.99 (12)	D19A—C19A—D19C	109.5
C4B—C4A—S5	120.99 (12)	D19B—C19A—D19C	109.5
C6—C5A—C9A	121.61 (17)	S1A—C20A—D20A	109.5
C6—C5A—S5	127.31 (14)	S1A—C20A—D20B	109.5
C9A—C5A—S5	111.07 (13)	D20A—C20A—D20B	109.5
C7—C6—C5A	118.33 (17)	S1A—C20A—D20C	109.5
C7—C6—H6A	120.8	D20A—C20A—D20C	109.5
C5A—C6—H6A	120.8	D20B—C20A—D20C	109.5
C6—C7—C8	121.20 (17)	S1B—C19B—D19D	109.5
C6—C7—H7A	119.4	S1B—C19B—D19E	109.5
C8—C7—H7A	119.4	D19D—C19B—D19E	109.5
C9—C8—C7	120.31 (17)	S1B—C19B—D19F	109.5
C9—C8—H8A	119.8	D19D—C19B—D19F	109.5
C7—C8—H8A	119.8	D19E—C19B—D19F	109.5
C4A—C9B—C9A	113.02 (14)	S1B—C20B—D20D	109.5
C4A—C9B—C10	123.29 (14)	S1B—C20B—D20E	109.5
C9A—C9B—C10	123.65 (14)	D20D—C20B—D20E	109.5
C9—C9A—C5A	118.92 (15)	S1B—C20B—D20F	109.5
C9—C9A—C9B	129.13 (15)	D20D—C20B—D20F	109.5
C5A—C9A—C9B	111.94 (15)	D20E—C20B—D20F	109.5
C12—N2—C1—O1	3.3 (3)	C10—C9B—C9A—C9	0.6 (3)
C3—N2—C1—O1	175.30 (16)	C4A—C9B—C9A—C5A	−0.6 (2)
C12—N2—C1—C10A	−174.00 (13)	C10—C9B—C9A—C5A	−178.18 (15)
C3—N2—C1—C10A	−1.96 (18)	C7—C8—C9—C9A	−0.8 (3)
C1—N2—C3—C3A	23.14 (17)	C5A—C9A—C9—C8	−0.3 (2)
C12—N2—C3—C3A	−164.58 (14)	C9B—C9A—C9—C8	−179.02 (17)
C4C—C3A—C3—N2	−154.00 (15)	O1—C1—C10A—C3A	162.34 (16)
C4B—C3A—C3—N2	−154.00 (15)	N2—C1—C10A—C3A	−20.34 (16)
C10A—C3A—C3—N2	−33.89 (15)	O1—C1—C10A—C10	35.5 (2)
C10A—C3A—C4B—O5A	172.66 (17)	N2—C1—C10A—C10	−147.14 (14)
C3—C3A—C4B—O5A	−70.7 (2)	C4C—C3A—C10A—C1	160.51 (13)
C10A—C3A—C4B—C4A	50.03 (19)	C4B—C3A—C10A—C1	160.51 (13)
C3—C3A—C4B—C4A	166.67 (15)	C3—C3A—C10A—C1	33.35 (15)
C10A—C3A—C4C—O5B	−78.8 (2)	C4C—C3A—C10A—C10	−69.78 (17)
C3—C3A—C4C—O5B	37.8 (3)	C4B—C3A—C10A—C10	−69.78 (17)
C10A—C3A—C4C—C4A	50.03 (19)	C3—C3A—C10A—C10	163.06 (13)
C3—C3A—C4C—C4A	166.67 (15)	C4A—C9B—C10—C10A	−12.4 (2)
O5B—C4C—C4A—C9B	107.8 (3)	C9A—C9B—C10—C10A	165.01 (14)
C3A—C4C—C4A—C9B	−19.0 (3)	C4A—C9B—C10—C11	111.08 (18)
O5B—C4C—C4A—S5	−70.3 (3)	C9A—C9B—C10—C11	−71.54 (19)
C3A—C4C—C4A—S5	162.82 (13)	C1—C10A—C10—C9B	168.32 (13)
O5A—C4B—C4A—C9B	−147.8 (2)	C3A—C10A—C10—C9B	46.52 (17)
C3A—C4B—C4A—C9B	−19.0 (3)	C1—C10A—C10—C11	45.88 (19)
O5A—C4B—C4A—S5	34.0 (2)	C3A—C10A—C10—C11	−75.93 (17)
C3A—C4B—C4A—S5	162.82 (13)	C9B—C10—C11—O2	−57.9 (2)
C5A—S5—C4A—C9B	0.01 (15)	C10A—C10—C11—O2	62.1 (2)
C5A—S5—C4A—C4C	178.43 (16)	C9B—C10—C11—O3	122.07 (15)
C5A—S5—C4A—C4B	178.43 (16)	C10A—C10—C11—O3	−117.90 (15)
C4A—S5—C5A—C6	−179.43 (19)	C1—N2—C12—C13	152.25 (16)
C4A—S5—C5A—C9A	−0.33 (14)	C3—N2—C12—C13	−19.0 (2)
C9A—C5A—C6—C7	−0.2 (3)	C1—N2—C12—C17	−28.8 (2)
S5—C5A—C6—C7	178.84 (16)	C3—N2—C12—C17	159.92 (15)
C5A—C6—C7—C8	−0.9 (3)	C17—C12—C13—C14	1.0 (2)
C6—C7—C8—C9	1.4 (3)	N2—C12—C13—C14	179.89 (15)
C4C—C4A—C9B—C9A	−178.00 (17)	C12—C13—C14—C15	1.6 (2)
C4B—C4A—C9B—C9A	−178.00 (17)	C18—O4—C15—C16	4.1 (2)
S5—C4A—C9B—C9A	0.3 (2)	C18—O4—C15—C14	−177.49 (15)
C4C—C4A—C9B—C10	−0.4 (3)	C13—C14—C15—O4	178.70 (15)
C4B—C4A—C9B—C10	−0.4 (3)	C13—C14—C15—C16	−2.8 (2)
S5—C4A—C9B—C10	177.93 (13)	O4—C15—C16—C17	179.86 (15)
C6—C5A—C9A—C9	0.8 (3)	C14—C15—C16—C17	1.5 (2)
S5—C5A—C9A—C9	−178.38 (13)	C15—C16—C17—C12	1.1 (2)
C6—C5A—C9A—C9B	179.71 (17)	C13—C12—C17—C16	−2.3 (2)
S5—C5A—C9A—C9B	0.55 (19)	N2—C12—C17—C16	178.78 (15)
C4A—C9B—C9A—C9	178.24 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···S1A	0.84	2.72	3.4846 (15)	152
O3—H3···O6A	0.84	1.72	2.563 (2)	176
O3—H3···O6B	0.84	2.06	2.852 (16)	158
O5A—H5A···O1^i	0.84	1.96	2.763 (2)	160
C3A—H3AA···O2	1.00	2.49	3.202 (2)	127
C3—H3A···O5B	0.99	2.54	2.887 (4)	100
C6—H6A···O6A^ii	0.95	2.48	3.307 (3)	145
C14—H14A···O4^iii	0.95	2.54	3.445 (2)	159
C17—H17A···O1	0.95	2.33	2.868 (2)	116
C17—H17A···O5B^iv	0.95	2.46	3.289 (4)	146
C18—H18C···O5B^v	0.98	2.43	2.922 (4)	110
C20A—D20A···O6A^vi	0.98	2.46	3.434 (3)	173
C20A—D20A···O6B^vi	0.98	1.87	2.839 (13)	168

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, −y+5/2, z+1/2; (iii) −x+1, −y, −z+1; (iv) x, −y+3/2, z−1/2; (v) −x+1, −y+1, −z+1; (vi) −x, y−1/2, −z+1/2.