N-tert-Butyl-2-{2-[2-(4-chloro­phen­yl)-4-hy­droxy-1-(5-methyl­isoxazol-3-yl)-5-oxo-2,5-di­hydro-1H-pyrrol-3-yl]-N-(4-meth­oxy­phen­yl)acetamido}-2-(4-meth­oxy­phen­yl)acetamide methanol monosolvate: single-crystal X-ray diffraction study and Hirshfeld surface analysis

The mol­ecular and crystal structures of the title compound, C₃₇H₄₁ClN₄O₈, which has potential biological activity have been studied. This compound exists in the crystal phase as a methanol solvate.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in solvent or counterion
• R factor = 0.063
• wR factor = 0.180
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H3       ..H8A      .       2.06 Ang.
                                                      x,y,z  =      1_555 Check

Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1       --C2       .        6.0 s.u.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C17      --C22      .        5.5 s.u.
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C12 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C33 Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including       O8A      0.123 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00441 Ang.
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H34B     ..H37C     .       2.14 Ang.
                                                   -1+x,y,z  =      1_455 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     12.970 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.387 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).         10 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.595          3 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          4 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          4 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          2 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
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  )       4.18 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  3  )       1.82 Check
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O1             108.9 Degree
PLAT793_ALERT_4_G Model has Chirality at C8          (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C24         (Centro SPGR)          S Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         14 Note

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

   2 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
   6 ALERT type 3 Indicator that the structure quality may be low
   8 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017/1 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

N-tert-Butyl-2-{2-[2-(4-chlorophenyl)-4-hydroxy-1-(5-methylisoxazol-3-yl)-5-oxo-2,5-dihydro-1H-pyrrol-3-yl]-N-(4-methoxyphenyl)acetamido}-2-(4-methoxyphenyl)acetamide methanol monosolvate

Crystal data

C36H37ClN4O7·CH4O	Z = 2
Mr = 705.19	F(000) = 744
Triclinic, P1	Dx = 1.271 Mg m^−3
a = 10.3211 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.9316 (11) Å	Cell parameters from 2243 reflections
c = 15.0269 (10) Å	θ = 3.6–24.8°
α = 107.179 (6)°	µ = 0.16 mm^−1
β = 100.769 (6)°	T = 293 K
γ = 109.649 (7)°	Plate, colourless
V = 1843.2 (2) Å^3	0.12 × 0.08 × 0.04 mm

Data collection

Rigaku Xcalibur, Sapphire3 diffractometer	6484 independent reflections
Radiation source: fine-focus sealed X-ray tube	3993 reflections with I > 2σ(I)
Detector resolution: 16.1827 pixels mm^-1	Rint = 0.062
ω scans	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2018)	h = −12→12
Tmin = 0.718, Tmax = 1.000	k = −16→16
12120 measured reflections	l = −17→17

Refinement

Refinement on F^2	14 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.063	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.180	w = 1/[σ^2(Fo^2) + (0.0804P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max < 0.001
6484 reflections	Δρmax = 0.37 e Å^−3
488 parameters	Δρmin = −0.37 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)
Cl1	0.18482 (10)	0.27201 (7)	0.45318 (8)	0.0879 (4)
O1	0.1363 (2)	0.78835 (18)	0.78187 (15)	0.0656 (6)
O2	0.6392 (2)	0.97400 (15)	0.79614 (13)	0.0527 (5)
O3	0.7446 (2)	0.94517 (18)	0.63187 (18)	0.0595 (6)
H3	0.741 (4)	0.957 (3)	0.586 (3)	0.083 (15)*
O4	0.3890 (3)	0.87873 (18)	0.40675 (14)	0.0708 (7)
O5	0.3359 (3)	0.30481 (19)	0.15424 (18)	0.0802 (8)
O6	0.0559 (2)	0.67660 (18)	0.23246 (16)	0.0630 (6)
O7	0.3038 (2)	0.61623 (18)	−0.17618 (14)	0.0609 (6)
N1	0.1951 (3)	0.7675 (2)	0.70394 (18)	0.0612 (7)
N2	0.4227 (2)	0.83021 (18)	0.68609 (15)	0.0460 (6)
N3	0.3530 (2)	0.72925 (16)	0.27770 (14)	0.0392 (5)
N4	0.0835 (3)	0.8240 (2)	0.19070 (17)	0.0490 (6)
H4	0.152 (4)	0.884 (3)	0.195 (2)	0.074 (11)*
C1	0.2010 (4)	0.8940 (3)	0.9544 (2)	0.0736 (10)
H1A	0.128840	0.922066	0.943675	0.110*
H1B	0.284465	0.949601	1.008583	0.110*
H1C	0.161991	0.829562	0.968871	0.110*
C2	0.2440 (3)	0.8644 (3)	0.8645 (2)	0.0546 (8)
C3	0.3694 (3)	0.8946 (2)	0.8449 (2)	0.0531 (8)
H3A	0.460502	0.945953	0.888417	0.064*
C4	0.3337 (3)	0.8316 (2)	0.74402 (19)	0.0434 (7)
C5	0.5651 (3)	0.9051 (2)	0.71337 (19)	0.0436 (7)
C6	0.6065 (3)	0.8850 (2)	0.62320 (19)	0.0438 (7)
C7	0.4959 (3)	0.8067 (2)	0.54664 (19)	0.0432 (7)
C8	0.3665 (3)	0.7620 (2)	0.57990 (18)	0.0442 (7)
H8	0.286697	0.776140	0.548349	0.053*
C9	0.3169 (3)	0.6397 (2)	0.55535 (18)	0.0416 (7)
C10	0.4071 (3)	0.5977 (2)	0.5935 (2)	0.0537 (8)
H10	0.496737	0.646313	0.640469	0.064*
C11	0.3678 (3)	0.4858 (2)	0.5639 (2)	0.0560 (8)
H11	0.429826	0.458959	0.590555	0.067*
C12	0.2347 (3)	0.4139 (2)	0.4940 (2)	0.0496 (7)
C13	0.1416 (3)	0.4526 (2)	0.4563 (2)	0.0562 (8)
H13	0.051140	0.403604	0.410486	0.067*
C14	0.1827 (3)	0.5653 (2)	0.4868 (2)	0.0513 (7)
H14	0.119336	0.591657	0.460966	0.062*
C15	0.4877 (3)	0.7567 (2)	0.44215 (18)	0.0467 (7)
H15A	0.441428	0.676778	0.419640	0.056*
H15B	0.585368	0.777049	0.438053	0.056*
C16	0.4042 (3)	0.7932 (2)	0.37513 (19)	0.0450 (7)
C17	0.3430 (3)	0.6180 (2)	0.24142 (18)	0.0396 (6)
C18	0.2315 (3)	0.5338 (2)	0.2456 (2)	0.0530 (8)
H18	0.159408	0.548169	0.268223	0.064*
C19	0.2238 (3)	0.4270 (2)	0.2165 (2)	0.0587 (8)
H19	0.147233	0.370399	0.219647	0.070*
C20	0.3309 (3)	0.4061 (2)	0.1831 (2)	0.0555 (8)
C21	0.4416 (4)	0.4902 (3)	0.1765 (2)	0.0644 (9)
H21	0.512658	0.475722	0.152511	0.077*
C22	0.4478 (3)	0.5952 (2)	0.2053 (2)	0.0545 (8)
H22	0.522867	0.651377	0.200380	0.065*
C23	0.2286 (4)	0.2176 (3)	0.1641 (3)	0.0916 (13)
H23A	0.135048	0.201790	0.122460	0.137*
H23B	0.229750	0.238635	0.231160	0.137*
H23C	0.247922	0.152986	0.145215	0.137*
C24	0.2850 (3)	0.7726 (2)	0.21251 (18)	0.0404 (6)
H24	0.342636	0.852694	0.238280	0.048*
C25	0.2869 (3)	0.7253 (2)	0.10845 (19)	0.0421 (6)
C26	0.4104 (3)	0.7724 (2)	0.0842 (2)	0.0512 (8)
H26	0.491865	0.831257	0.132629	0.061*
C27	0.4136 (3)	0.7330 (3)	−0.0107 (2)	0.0564 (8)
H27	0.497132	0.764969	−0.025541	0.068*
C28	0.2927 (3)	0.6460 (2)	−0.0838 (2)	0.0475 (7)
C29	0.1706 (3)	0.5974 (2)	−0.0612 (2)	0.0533 (8)
H29	0.089435	0.538224	−0.109724	0.064*
C30	0.1692 (3)	0.6372 (2)	0.03492 (19)	0.0494 (7)
H30	0.086484	0.603566	0.049952	0.059*
C31	0.1776 (4)	0.5334 (3)	−0.2546 (2)	0.0748 (11)
H31A	0.196560	0.524816	−0.315984	0.112*
H31B	0.098515	0.554956	−0.254578	0.112*
H31C	0.152642	0.464518	−0.246083	0.112*
C32	0.1300 (3)	0.7536 (2)	0.21472 (19)	0.0434 (7)
C33	−0.0649 (3)	0.8177 (3)	0.1762 (3)	0.0637 (9)
C34	−0.1035 (4)	0.8284 (4)	0.2694 (3)	0.0987 (14)
H34A	−0.104076	0.767117	0.286450	0.148*
H34B	−0.197859	0.828863	0.259680	0.148*
H34C	−0.033068	0.896180	0.321512	0.148*
C35	−0.1715 (4)	0.7095 (3)	0.0922 (3)	0.1000 (14)
H35A	−0.140232	0.702183	0.035187	0.150*
H35B	−0.266155	0.709336	0.077334	0.150*
H35C	−0.175204	0.648757	0.111037	0.150*
C36	−0.0624 (5)	0.9159 (4)	0.1482 (4)	0.1060 (15)
H36A	0.007832	0.983643	0.200456	0.159*
H36B	−0.156610	0.916650	0.137701	0.159*
H36C	−0.036727	0.908644	0.089156	0.159*
O8A	0.754 (3)	1.031 (2)	0.4990 (12)	0.127 (8)	0.303 (10)
H8A	0.682895	1.041989	0.506038	0.191*	0.303 (10)
C37A	0.744 (3)	0.9975 (16)	0.3987 (13)	0.117 (6)	0.303 (10)
H37A	0.802378	1.059842	0.387193	0.175*	0.303 (10)
H37B	0.644924	0.969545	0.359214	0.175*	0.303 (10)
H37C	0.778623	0.940725	0.381619	0.175*	0.303 (10)
O8B	0.7271 (8)	0.9964 (6)	0.4729 (6)	0.084 (2)	0.697 (10)
H8B	0.655470	1.005555	0.450322	0.127*	0.697 (10)
C37B	0.8511 (8)	1.0727 (6)	0.4653 (7)	0.101 (3)	0.697 (10)
H37D	0.926332	1.046763	0.469376	0.151*	0.697 (10)
H37E	0.884329	1.143282	0.517811	0.151*	0.697 (10)
H37F	0.826852	1.079852	0.403396	0.151*	0.697 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0789 (6)	0.0378 (5)	0.1184 (8)	0.0190 (4)	0.0063 (6)	0.0136 (5)
O1	0.0552 (13)	0.0732 (16)	0.0524 (13)	0.0196 (12)	0.0169 (11)	0.0114 (11)
O2	0.0585 (12)	0.0386 (11)	0.0372 (11)	0.0093 (10)	0.0026 (10)	0.0033 (9)
O3	0.0551 (14)	0.0508 (14)	0.0535 (14)	0.0101 (11)	0.0117 (12)	0.0120 (11)
O4	0.1146 (19)	0.0506 (14)	0.0430 (12)	0.0494 (14)	0.0060 (12)	0.0071 (10)
O5	0.0854 (17)	0.0464 (15)	0.0958 (18)	0.0347 (13)	0.0134 (14)	0.0115 (13)
O6	0.0582 (13)	0.0572 (14)	0.0817 (16)	0.0205 (11)	0.0289 (12)	0.0376 (12)
O7	0.0605 (13)	0.0701 (15)	0.0466 (12)	0.0214 (11)	0.0230 (11)	0.0184 (10)
N1	0.0548 (16)	0.0588 (17)	0.0458 (14)	0.0111 (13)	0.0117 (13)	0.0052 (12)
N2	0.0468 (13)	0.0391 (14)	0.0361 (12)	0.0111 (11)	0.0070 (11)	0.0050 (10)
N3	0.0475 (13)	0.0298 (12)	0.0326 (11)	0.0155 (10)	0.0055 (10)	0.0070 (9)
N4	0.0488 (15)	0.0428 (15)	0.0511 (15)	0.0198 (13)	0.0066 (12)	0.0172 (12)
C1	0.073 (2)	0.087 (3)	0.054 (2)	0.032 (2)	0.0218 (18)	0.0199 (18)
C2	0.0558 (19)	0.053 (2)	0.0407 (16)	0.0199 (16)	0.0050 (15)	0.0088 (14)
C3	0.0506 (18)	0.0526 (19)	0.0384 (16)	0.0162 (15)	0.0043 (14)	0.0063 (13)
C4	0.0489 (17)	0.0353 (16)	0.0370 (14)	0.0144 (13)	0.0064 (13)	0.0099 (12)
C5	0.0529 (17)	0.0263 (14)	0.0381 (15)	0.0125 (13)	0.0017 (14)	0.0070 (12)
C6	0.0486 (17)	0.0333 (15)	0.0397 (15)	0.0123 (13)	0.0084 (13)	0.0102 (12)
C7	0.0485 (16)	0.0356 (15)	0.0371 (14)	0.0159 (13)	0.0032 (13)	0.0113 (12)
C8	0.0476 (16)	0.0343 (15)	0.0335 (14)	0.0125 (13)	−0.0001 (13)	0.0036 (11)
C9	0.0414 (15)	0.0370 (16)	0.0358 (14)	0.0112 (13)	0.0064 (12)	0.0093 (12)
C10	0.0450 (17)	0.0417 (18)	0.0537 (17)	0.0112 (14)	−0.0023 (14)	0.0102 (14)
C11	0.0502 (18)	0.047 (2)	0.065 (2)	0.0211 (15)	0.0082 (16)	0.0205 (15)
C12	0.0516 (17)	0.0326 (16)	0.0550 (17)	0.0135 (14)	0.0154 (15)	0.0097 (13)
C13	0.0469 (17)	0.0413 (18)	0.0533 (18)	0.0102 (14)	−0.0001 (14)	0.0015 (14)
C14	0.0445 (16)	0.0437 (18)	0.0499 (17)	0.0165 (14)	−0.0004 (14)	0.0089 (13)
C15	0.0612 (18)	0.0397 (16)	0.0347 (14)	0.0241 (14)	0.0075 (14)	0.0094 (12)
C16	0.0551 (17)	0.0311 (15)	0.0381 (15)	0.0162 (13)	0.0063 (13)	0.0065 (12)
C17	0.0427 (15)	0.0375 (16)	0.0327 (14)	0.0177 (13)	0.0058 (12)	0.0084 (11)
C18	0.0536 (18)	0.0432 (18)	0.0590 (19)	0.0194 (15)	0.0188 (15)	0.0159 (14)
C19	0.0585 (19)	0.0346 (18)	0.068 (2)	0.0119 (15)	0.0101 (17)	0.0143 (15)
C20	0.062 (2)	0.0386 (18)	0.0523 (18)	0.0274 (16)	0.0026 (16)	0.0020 (14)
C21	0.067 (2)	0.056 (2)	0.075 (2)	0.0359 (18)	0.0266 (19)	0.0170 (17)
C22	0.0540 (18)	0.0471 (19)	0.0589 (19)	0.0210 (15)	0.0161 (16)	0.0174 (14)
C23	0.097 (3)	0.043 (2)	0.113 (3)	0.028 (2)	0.004 (3)	0.020 (2)
C24	0.0437 (15)	0.0331 (15)	0.0366 (14)	0.0128 (12)	0.0044 (12)	0.0121 (11)
C25	0.0468 (16)	0.0378 (16)	0.0384 (14)	0.0150 (13)	0.0099 (13)	0.0154 (12)
C26	0.0442 (17)	0.0541 (19)	0.0468 (17)	0.0149 (14)	0.0071 (14)	0.0189 (14)
C27	0.0449 (17)	0.068 (2)	0.0549 (19)	0.0178 (16)	0.0179 (15)	0.0269 (16)
C28	0.0540 (18)	0.0513 (18)	0.0412 (16)	0.0246 (15)	0.0173 (14)	0.0188 (14)
C29	0.0538 (18)	0.0444 (18)	0.0424 (16)	0.0069 (14)	0.0121 (14)	0.0089 (13)
C30	0.0496 (17)	0.0475 (18)	0.0383 (15)	0.0087 (14)	0.0160 (14)	0.0116 (13)
C31	0.087 (3)	0.071 (2)	0.0449 (18)	0.013 (2)	0.0268 (19)	0.0129 (17)
C32	0.0462 (16)	0.0418 (17)	0.0360 (14)	0.0166 (14)	0.0091 (13)	0.0111 (12)
C33	0.0533 (19)	0.059 (2)	0.071 (2)	0.0274 (17)	0.0067 (17)	0.0194 (17)
C34	0.074 (3)	0.119 (4)	0.106 (3)	0.051 (3)	0.038 (2)	0.030 (3)
C35	0.066 (2)	0.088 (3)	0.099 (3)	0.023 (2)	−0.017 (2)	0.011 (2)
C36	0.092 (3)	0.101 (3)	0.153 (4)	0.061 (3)	0.020 (3)	0.074 (3)
O8A	0.140 (12)	0.122 (14)	0.101 (11)	0.012 (11)	0.040 (9)	0.065 (10)
C37A	0.178 (15)	0.106 (12)	0.098 (11)	0.062 (11)	0.086 (10)	0.050 (9)
O8B	0.088 (4)	0.073 (4)	0.096 (6)	0.033 (3)	0.032 (3)	0.036 (3)
C37B	0.107 (6)	0.111 (6)	0.137 (7)	0.060 (5)	0.068 (5)	0.081 (5)

Geometric parameters (Å, º)

Cl1—C12	1.741 (3)	C18—H18	0.9300
O1—N1	1.417 (3)	C18—C19	1.391 (4)
O1—C2	1.348 (3)	C19—H19	0.9300
O2—C5	1.224 (3)	C19—C20	1.377 (4)
O3—H3	0.75 (4)	C20—C21	1.377 (5)
O3—C6	1.346 (3)	C21—H21	0.9300
O4—C16	1.221 (3)	C21—C22	1.373 (4)
O5—C20	1.371 (3)	C22—H22	0.9300
O5—C23	1.409 (4)	C23—H23A	0.9600
O6—C32	1.225 (3)	C23—H23B	0.9600
O7—C28	1.365 (3)	C23—H23C	0.9600
O7—C31	1.425 (4)	C24—H24	0.9800
N1—C4	1.307 (3)	C24—C25	1.514 (4)
N2—C4	1.380 (3)	C24—C32	1.540 (4)
N2—C5	1.381 (3)	C25—C26	1.393 (4)
N2—C8	1.474 (3)	C25—C30	1.377 (4)
N3—C16	1.357 (3)	C26—H26	0.9300
N3—C17	1.443 (3)	C26—C27	1.378 (4)
N3—C24	1.482 (3)	C27—H27	0.9300
N4—H4	0.87 (3)	C27—C28	1.384 (4)
N4—C32	1.335 (4)	C28—C29	1.373 (4)
N4—C33	1.475 (4)	C29—H29	0.9300
C1—H1A	0.9600	C29—C30	1.390 (4)
C1—H1B	0.9600	C30—H30	0.9300
C1—H1C	0.9600	C31—H31A	0.9600
C1—C2	1.486 (4)	C31—H31B	0.9600
C2—C3	1.337 (4)	C31—H31C	0.9600
C3—H3A	0.9300	C33—C34	1.505 (5)
C3—C4	1.412 (4)	C33—C35	1.522 (5)
C5—C6	1.473 (4)	C33—C36	1.539 (5)
C6—C7	1.322 (4)	C34—H34A	0.9600
C7—C8	1.515 (4)	C34—H34B	0.9600
C7—C15	1.491 (4)	C34—H34C	0.9600
C8—H8	0.9800	C35—H35A	0.9600
C8—C9	1.507 (4)	C35—H35B	0.9600
C9—C10	1.379 (4)	C35—H35C	0.9600
C9—C14	1.388 (4)	C36—H36A	0.9600
C10—H10	0.9300	C36—H36B	0.9600
C10—C11	1.375 (4)	C36—H36C	0.9600
C11—H11	0.9300	O8A—H8A	0.8200
C11—C12	1.381 (4)	O8A—C37A	1.412 (5)
C12—C13	1.364 (4)	C37A—H37A	0.9600
C13—H13	0.9300	C37A—H37B	0.9600
C13—C14	1.381 (4)	C37A—H37C	0.9600
C14—H14	0.9300	O8B—H8B	0.8200
C15—H15A	0.9700	O8B—C37B	1.412 (5)
C15—H15B	0.9700	C37B—H37D	0.9600
C15—C16	1.513 (4)	C37B—H37E	0.9600
C17—C18	1.366 (4)	C37B—H37F	0.9600
C17—C22	1.383 (4)
C2—O1—N1	108.9 (2)	C20—C21—H21	119.7
C6—O3—H3	106 (3)	C22—C21—C20	120.5 (3)
C20—O5—C23	117.9 (3)	C22—C21—H21	119.7
C28—O7—C31	117.5 (2)	C17—C22—H22	119.8
C4—N1—O1	104.6 (2)	C21—C22—C17	120.4 (3)
C4—N2—C5	125.3 (2)	C21—C22—H22	119.8
C4—N2—C8	122.4 (2)	O5—C23—H23A	109.5
C5—N2—C8	111.2 (2)	O5—C23—H23B	109.5
C16—N3—C17	121.8 (2)	O5—C23—H23C	109.5
C16—N3—C24	115.9 (2)	H23A—C23—H23B	109.5
C17—N3—C24	121.48 (19)	H23A—C23—H23C	109.5
C32—N4—H4	114 (2)	H23B—C23—H23C	109.5
C32—N4—C33	125.7 (3)	N3—C24—H24	107.3
C33—N4—H4	119 (2)	N3—C24—C25	112.2 (2)
H1A—C1—H1B	109.5	N3—C24—C32	111.1 (2)
H1A—C1—H1C	109.5	C25—C24—H24	107.3
H1B—C1—H1C	109.5	C25—C24—C32	111.3 (2)
C2—C1—H1A	109.5	C32—C24—H24	107.3
C2—C1—H1B	109.5	C26—C25—C24	119.8 (2)
C2—C1—H1C	109.5	C30—C25—C24	122.5 (2)
O1—C2—C1	115.8 (3)	C30—C25—C26	117.8 (3)
C3—C2—O1	109.4 (3)	C25—C26—H26	119.5
C3—C2—C1	134.7 (3)	C27—C26—C25	121.0 (3)
C2—C3—H3A	127.4	C27—C26—H26	119.5
C2—C3—C4	105.1 (3)	C26—C27—H27	119.9
C4—C3—H3A	127.4	C26—C27—C28	120.2 (3)
N1—C4—N2	118.8 (2)	C28—C27—H27	119.9
N1—C4—C3	111.9 (3)	O7—C28—C27	115.9 (3)
N2—C4—C3	129.3 (3)	O7—C28—C29	124.3 (3)
O2—C5—N2	126.0 (3)	C29—C28—C27	119.8 (3)
O2—C5—C6	128.1 (3)	C28—C29—H29	120.3
N2—C5—C6	106.0 (2)	C28—C29—C30	119.5 (3)
O3—C6—C5	117.3 (2)	C30—C29—H29	120.3
C7—C6—O3	131.8 (3)	C25—C30—C29	121.8 (3)
C7—C6—C5	110.9 (2)	C25—C30—H30	119.1
C6—C7—C8	109.5 (2)	C29—C30—H30	119.1
C6—C7—C15	130.0 (3)	O7—C31—H31A	109.5
C15—C7—C8	120.3 (2)	O7—C31—H31B	109.5
N2—C8—C7	102.3 (2)	O7—C31—H31C	109.5
N2—C8—H8	109.6	H31A—C31—H31B	109.5
N2—C8—C9	114.2 (2)	H31A—C31—H31C	109.5
C7—C8—H8	109.6	H31B—C31—H31C	109.5
C9—C8—C7	111.2 (2)	O6—C32—N4	124.3 (3)
C9—C8—H8	109.6	O6—C32—C24	121.5 (3)
C10—C9—C8	121.5 (2)	N4—C32—C24	114.0 (3)
C10—C9—C14	117.9 (3)	N4—C33—C34	110.8 (3)
C14—C9—C8	120.4 (2)	N4—C33—C35	109.5 (3)
C9—C10—H10	119.2	N4—C33—C36	105.1 (3)
C11—C10—C9	121.7 (3)	C34—C33—C35	111.2 (3)
C11—C10—H10	119.2	C34—C33—C36	110.1 (3)
C10—C11—H11	120.5	C35—C33—C36	109.9 (3)
C10—C11—C12	119.0 (3)	C33—C34—H34A	109.5
C12—C11—H11	120.5	C33—C34—H34B	109.5
C11—C12—Cl1	119.7 (2)	C33—C34—H34C	109.5
C13—C12—Cl1	119.4 (2)	H34A—C34—H34B	109.5
C13—C12—C11	120.9 (3)	H34A—C34—H34C	109.5
C12—C13—H13	120.3	H34B—C34—H34C	109.5
C12—C13—C14	119.4 (3)	C33—C35—H35A	109.5
C14—C13—H13	120.3	C33—C35—H35B	109.5
C9—C14—H14	119.4	C33—C35—H35C	109.5
C13—C14—C9	121.1 (3)	H35A—C35—H35B	109.5
C13—C14—H14	119.4	H35A—C35—H35C	109.5
C7—C15—H15A	109.0	H35B—C35—H35C	109.5
C7—C15—H15B	109.0	C33—C36—H36A	109.5
C7—C15—C16	112.7 (2)	C33—C36—H36B	109.5
H15A—C15—H15B	107.8	C33—C36—H36C	109.5
C16—C15—H15A	109.0	H36A—C36—H36B	109.5
C16—C15—H15B	109.0	H36A—C36—H36C	109.5
O4—C16—N3	121.5 (2)	H36B—C36—H36C	109.5
O4—C16—C15	121.5 (2)	C37A—O8A—H8A	109.5
N3—C16—C15	116.9 (2)	O8A—C37A—H37A	109.5
C18—C17—N3	120.0 (2)	O8A—C37A—H37B	109.5
C18—C17—C22	118.9 (3)	O8A—C37A—H37C	109.5
C22—C17—N3	121.0 (3)	H37A—C37A—H37B	109.5
C17—C18—H18	119.4	H37A—C37A—H37C	109.5
C17—C18—C19	121.3 (3)	H37B—C37A—H37C	109.5
C19—C18—H18	119.4	C37B—O8B—H8B	109.5
C18—C19—H19	120.4	O8B—C37B—H37D	109.5
C20—C19—C18	119.2 (3)	O8B—C37B—H37E	109.5
C20—C19—H19	120.4	O8B—C37B—H37F	109.5
O5—C20—C19	124.3 (3)	H37D—C37B—H37E	109.5
O5—C20—C21	116.0 (3)	H37D—C37B—H37F	109.5
C19—C20—C21	119.7 (3)	H37E—C37B—H37F	109.5
Cl1—C12—C13—C14	−178.3 (2)	C9—C10—C11—C12	0.2 (5)
O1—N1—C4—N2	179.9 (2)	C10—C9—C14—C13	−1.2 (4)
O1—N1—C4—C3	−0.3 (3)	C10—C11—C12—Cl1	178.4 (2)
O1—C2—C3—C4	−0.4 (3)	C10—C11—C12—C13	−1.6 (5)
O2—C5—C6—O3	3.6 (4)	C11—C12—C13—C14	1.7 (5)
O2—C5—C6—C7	−177.3 (3)	C12—C13—C14—C9	−0.2 (5)
O3—C6—C7—C8	176.7 (3)	C14—C9—C10—C11	1.2 (4)
O3—C6—C7—C15	1.0 (5)	C15—C7—C8—N2	177.6 (2)
O5—C20—C21—C22	−178.9 (3)	C15—C7—C8—C9	55.3 (3)
O7—C28—C29—C30	−177.4 (3)	C16—N3—C17—C18	78.2 (3)
N1—O1—C2—C1	−178.7 (3)	C16—N3—C17—C22	−99.5 (3)
N1—O1—C2—C3	0.2 (3)	C16—N3—C24—C25	156.7 (2)
N2—C5—C6—O3	−176.9 (2)	C16—N3—C24—C32	−78.1 (3)
N2—C5—C6—C7	2.2 (3)	C17—N3—C16—O4	−166.9 (3)
N2—C8—C9—C10	−54.2 (4)	C17—N3—C16—C15	16.2 (4)
N2—C8—C9—C14	131.3 (3)	C17—N3—C24—C25	−33.4 (3)
N3—C17—C18—C19	−176.2 (2)	C17—N3—C24—C32	91.9 (3)
N3—C17—C22—C21	176.0 (3)	C17—C18—C19—C20	0.1 (5)
N3—C24—C25—C26	−83.4 (3)	C18—C17—C22—C21	−1.7 (4)
N3—C24—C25—C30	97.7 (3)	C18—C19—C20—O5	178.8 (3)
N3—C24—C32—O6	−27.8 (3)	C18—C19—C20—C21	−1.6 (5)
N3—C24—C32—N4	155.6 (2)	C19—C20—C21—C22	1.5 (5)
C1—C2—C3—C4	178.2 (4)	C20—C21—C22—C17	0.2 (5)
C2—O1—N1—C4	0.1 (3)	C22—C17—C18—C19	1.6 (4)
C2—C3—C4—N1	0.5 (4)	C23—O5—C20—C19	−3.3 (5)
C2—C3—C4—N2	−179.8 (3)	C23—O5—C20—C21	177.1 (3)
C4—N2—C5—O2	10.4 (5)	C24—N3—C16—O4	3.0 (4)
C4—N2—C5—C6	−169.1 (2)	C24—N3—C16—C15	−173.9 (2)
C4—N2—C8—C7	168.3 (2)	C24—N3—C17—C18	−91.1 (3)
C4—N2—C8—C9	−71.4 (3)	C24—N3—C17—C22	91.1 (3)
C5—N2—C4—N1	168.8 (3)	C24—C25—C26—C27	−178.1 (3)
C5—N2—C4—C3	−10.9 (5)	C24—C25—C30—C29	177.5 (2)
C5—N2—C8—C7	−0.1 (3)	C25—C24—C32—O6	97.9 (3)
C5—N2—C8—C9	120.2 (3)	C25—C24—C32—N4	−78.7 (3)
C5—C6—C7—C8	−2.2 (3)	C25—C26—C27—C28	0.5 (5)
C5—C6—C7—C15	−177.9 (3)	C26—C25—C30—C29	−1.5 (4)
C6—C7—C8—N2	1.4 (3)	C26—C27—C28—O7	177.0 (3)
C6—C7—C8—C9	−120.9 (3)	C26—C27—C28—C29	−1.4 (5)
C6—C7—C15—C16	−107.2 (3)	C27—C28—C29—C30	0.9 (4)
C7—C8—C9—C10	60.9 (3)	C28—C29—C30—C25	0.6 (5)
C7—C8—C9—C14	−113.6 (3)	C30—C25—C26—C27	0.9 (4)
C7—C15—C16—O4	22.5 (4)	C31—O7—C28—C27	−174.8 (3)
C7—C15—C16—N3	−160.6 (2)	C31—O7—C28—C29	3.6 (4)
C8—N2—C4—N1	2.2 (4)	C32—N4—C33—C34	61.9 (4)
C8—N2—C4—C3	−177.5 (3)	C32—N4—C33—C35	−61.1 (4)
C8—N2—C5—O2	178.3 (3)	C32—N4—C33—C36	−179.1 (3)
C8—N2—C5—C6	−1.2 (3)	C32—C24—C25—C26	151.4 (2)
C8—C7—C15—C16	77.5 (3)	C32—C24—C25—C30	−27.5 (4)
C8—C9—C10—C11	−173.5 (3)	C33—N4—C32—O6	−3.6 (4)
C8—C9—C14—C13	173.5 (3)	C33—N4—C32—C24	172.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O8A	0.75 (4)	1.88 (5)	2.61 (3)	162 (4)
O3—H3···O8B	0.75 (4)	1.93 (4)	2.680 (10)	175 (4)
N4—H4···O2^i	0.87 (3)	2.33 (3)	3.193 (3)	170 (3)
O8A—H8A···O4^i	0.82	1.88	2.60 (3)	145
O8B—H8B···O4^i	0.82	2.50	2.843 (8)	107

Symmetry code: (i) −x+1, −y+2, −z+1.