Crystal structure and absolute configuration of (3S,4aS,8aS)-N-tert-butyl-2-[(S)-3-(2-chloro-4-nitro­benzamido)-2-hy­droxy­prop­yl]deca­hydro­isoquinoline-3-carboxamide and (3S,4aS,8aS)-N-tert-butyl-2-{(S)-2-[(S)-1-(2-chloro-4-nitro­benzoyl)pyrrolidin-2-yl]-2-hy­droxy­eth­yl}deca­hydro­iso­quinoline-3-carboxamide

The crystal structure and absolute configuration of two new nelfinavir analogs have been determined. Inter­molecular hydrogen bonding leads to two-dimensional sheets in one analog and one-dimensional chains in the other.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.035
• wR factor = 0.085
• Data-to-parameter ratio = 15.7

Structure: II

• Single-crystal X-ray study
• T = 168 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.032
• wR factor = 0.082
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT220_ALERT_2_C Large Non-Solvent  O     Ueq(max)/Ueq(min) Range        3.1 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     --  C4      ..        5.5 su

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         10 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          8 Report
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          4 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          1 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          2 Report
PLAT230_ALERT_2_G Hirshfeld Test Diff for    Cl1B   --  C2      ..        7.4 su
PLAT301_ALERT_3_G Main Residue  Disorder ............ Percentage =         12 Note
PLAT432_ALERT_2_G Short Inter X...Y Contact  O1     ..  C6      ..       2.93 Ang.
PLAT791_ALERT_4_G The Model has Chirality at C9      (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C11     (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C13     (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C18     (Chiral SPGR)          S Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         53 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          4 Note

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

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




Datablock: II


Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         25 Note
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size ....       0.86 mm
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          9 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          3 Report
PLAT301_ALERT_3_G Main Residue  Disorder ............ Percentage =         24 Note
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #          7 Check
              C7B  -O3   -C7      1.555   1.555   1.555             13.00 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #          8 Check
              O3B  -C7   -O3      1.555   1.555   1.555             22.90 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #         14 Check
              C7   -O3B  -C7B     1.555   1.555   1.555             13.00 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #         15 Check
              O3   -C7B  -O3B     1.555   1.555   1.555             22.80 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #         22 Check
              C7   -N2   -C7B     1.555   1.555   1.555             12.00 Deg.
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... #         56 Check
              C7   -C6   -C7B     1.555   1.555   1.555             11.00 Deg.
PLAT791_ALERT_4_G The Model has Chirality at C8      (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C12     (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C14     (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C16     (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C21     (Chiral SPGR)          S Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         14 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note

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

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

---

Computing details

For both compounds, data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014), XPREP (Bruker, 2014), and SADABS (Bruker, 2014). Program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008) for (I); SHELXS2014 (Sheldrick, 2015) for (II). For both compounds, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015). Molecular graphics: SHELXTL (Sheldrick, 2008) and CrystalMaker (CrystalMaker, 1994) for (I); SHELXTL (Sheldrick, 2015) and CrystalMaker (CrystalMaker, 1994) for (II). For both compounds, software used to prepare material for publication: XCIF (Bruker, 2014) and publCIF (Westrip, 2010).

(I) (3S,4aS,8aS)-N-tert-Butyl-2-[(S)-3-(2-chloro-4-nitrobenzamido)-2-hydroxypropyl]decahydroisoquinoline-3-carboxamide

Crystal data

C24H35ClN4O5	F(000) = 1056
Mr = 495.01	Dx = 1.270 Mg m^−3
Orthorhombic, P21212	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2ab	Cell parameters from 9966 reflections
a = 18.8408 (7) Å	θ = 2.3–24.5°
b = 20.2263 (8) Å	µ = 0.19 mm^−1
c = 6.7923 (3) Å	T = 193 K
V = 2588.41 (18) Å^3	Prism, colourless
Z = 4	0.37 × 0.36 × 0.29 mm

Data collection

Siemens Platform/APEXII CCD diffractometer	5243 independent reflections
Radiation source: normal-focus sealed tube	4694 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
profile data from φ and ω scans	θmax = 26.3°, θmin = 1.5°
Absorption correction: integration (SHELXTL/XPREP; Bruker, 2014)	h = −23→23
Tmin = 0.953, Tmax = 0.960	k = −25→25
30342 measured reflections	l = −8→8

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.035	w = 1/[σ^2(Fo^2) + (0.0355P)^2 + 0.5785P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.085	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.34 e Å^−3
5243 reflections	Δρmin = −0.43 e Å^−3
333 parameters	Absolute structure: Flack (1983); Hooft et al. (2008); 2720 Friedels
53 restraints	Absolute structure parameter: −0.008 (18)

Special details

Experimental. One distinct cell was identified using APEX2 (Bruker, 2014). Four frame series were integrated and filtered for statistical outliers using SAINT (Bruker, 2014) then corrected for absorption by integration using SHELXTL/XPREP V2005/2 (Bruker, 2014) before using SAINT/SADABS (Bruker, 2014) to sort, merge, and scale the combined data No decay correction was applied.

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. Structure was phased by direct (Sheldrick, 2015). Systematic conditions suggested the ambiguous space group. The space group choice was confirmed by successful convergence of the full-matrix least-squares refinement on F². The final map had no significant features. A final analysis of variance between observed and calculated structure factors showed no dependence on amplitude or resolution.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.29551 (15)	0.69804 (7)	0.67519 (15)	0.0735 (5)	0.941 (8)
Cl1B	0.326 (2)	0.6888 (7)	0.664 (3)	0.0735 (5)	0.059 (8)
O1	0.3558 (8)	0.8988 (8)	0.2519 (16)	0.086 (2)	0.60 (2)
O2	0.4046 (8)	0.9713 (5)	0.445 (2)	0.116 (3)	0.60 (2)
N1	0.3808 (6)	0.9169 (5)	0.4064 (12)	0.0715 (17)	0.60 (2)
O1B	0.3725 (13)	0.9134 (12)	0.271 (3)	0.086 (2)	0.40 (2)
O2B	0.4360 (11)	0.9754 (7)	0.453 (3)	0.116 (3)	0.40 (2)
N1B	0.3991 (9)	0.9260 (7)	0.431 (2)	0.0715 (17)	0.40 (2)
C1	0.38040 (11)	0.78173 (14)	0.8790 (4)	0.0477 (6)
C2	0.34335 (12)	0.77084 (14)	0.7057 (4)	0.0520 (7)
C3	0.34488 (14)	0.81498 (16)	0.5532 (4)	0.0585 (7)
H3A	0.3207	0.8062	0.4333	0.070*
C4	0.38270 (16)	0.87247 (16)	0.5797 (5)	0.0635 (8)
C5	0.41913 (17)	0.88668 (15)	0.7505 (5)	0.0675 (8)
H5A	0.4439	0.9272	0.7658	0.081*
C6	0.41831 (14)	0.84036 (15)	0.8974 (5)	0.0594 (7)
H6A	0.4443	0.8485	1.0148	0.071*
C7	0.38161 (12)	0.73281 (14)	1.0445 (4)	0.0478 (6)
O3	0.32755 (9)	0.71943 (11)	1.1373 (3)	0.0644 (5)
O4	0.48956 (9)	0.73984 (10)	1.4849 (3)	0.0534 (5)
H4B	0.5165 (17)	0.7479 (17)	1.585 (5)	0.080*
O5	0.56221 (7)	0.75831 (7)	0.8387 (2)	0.0372 (3)
N2	0.44567 (10)	0.70759 (11)	1.0807 (3)	0.0438 (5)
H2	0.4786 (16)	0.7171 (15)	1.005 (5)	0.066*
N3	0.60919 (9)	0.66293 (9)	1.1177 (3)	0.0368 (4)
N4	0.67223 (10)	0.80363 (9)	0.8528 (3)	0.0417 (4)
H4	0.7145 (16)	0.7950 (14)	0.884 (4)	0.063*
C8	0.46111 (12)	0.66114 (13)	1.2385 (4)	0.0459 (6)
H8A	0.4766	0.6186	1.1805	0.055*
H8B	0.4172	0.6528	1.3145	0.055*
C9	0.51828 (11)	0.68604 (12)	1.3772 (3)	0.0420 (5)
H9A	0.5310	0.6499	1.4712	0.050*
C10	0.58565 (11)	0.70901 (12)	1.2713 (3)	0.0386 (5)
H10A	0.5767	0.7528	1.2109	0.046*
H10B	0.6242	0.7144	1.3691	0.046*
C11	0.65713 (11)	0.69212 (11)	0.9715 (3)	0.0380 (5)
H11A	0.7036	0.7026	1.0353	0.046*
C12	0.66899 (13)	0.64166 (11)	0.8056 (4)	0.0410 (5)
H12A	0.6230	0.6318	0.7413	0.049*
H12B	0.7010	0.6610	0.7054	0.049*
C13	0.70138 (14)	0.57736 (12)	0.8829 (4)	0.0494 (6)
H13A	0.7500	0.5880	0.9326	0.059*
C14	0.70957 (16)	0.52528 (13)	0.7203 (4)	0.0590 (7)
H14A	0.7303	0.5467	0.6025	0.071*
H14B	0.7434	0.4910	0.7656	0.071*
C15	0.64047 (16)	0.49205 (14)	0.6624 (4)	0.0611 (7)
H15A	0.6503	0.4565	0.5661	0.073*
H15B	0.6089	0.5248	0.5988	0.073*
C16	0.60342 (19)	0.46287 (13)	0.8419 (5)	0.0696 (9)
H16A	0.6333	0.4276	0.8999	0.084*
H16B	0.5576	0.4430	0.8019	0.084*
C17	0.59030 (17)	0.51683 (13)	0.9945 (4)	0.0610 (8)
H17A	0.5575	0.5502	0.9387	0.073*
H17B	0.5671	0.4971	1.1115	0.073*
C18	0.65836 (16)	0.55060 (13)	1.0574 (4)	0.0550 (7)
H18A	0.6883	0.5165	1.1243	0.066*
C19	0.64454 (15)	0.60538 (13)	1.2068 (4)	0.0505 (6)
H19A	0.6145	0.5878	1.3143	0.061*
H19B	0.6902	0.6196	1.2650	0.061*
C20	0.62618 (10)	0.75493 (11)	0.8828 (3)	0.0354 (5)
C21	0.65543 (13)	0.87079 (12)	0.7767 (4)	0.0480 (6)
C22	0.60827 (17)	0.90585 (14)	0.9239 (5)	0.0679 (8)
H22A	0.5644	0.8805	0.9422	0.102*
H22B	0.5967	0.9501	0.8746	0.102*
H22C	0.6332	0.9097	1.0500	0.102*
C23	0.62113 (16)	0.86682 (14)	0.5736 (5)	0.0606 (8)
H23A	0.5739	0.8468	0.5852	0.091*
H23B	0.6507	0.8397	0.4866	0.091*
H23C	0.6167	0.9114	0.5184	0.091*
C24	0.72639 (15)	0.90696 (15)	0.7599 (6)	0.0682 (9)
H24A	0.7496	0.9079	0.8890	0.102*
H24B	0.7182	0.9523	0.7145	0.102*
H24C	0.7569	0.8838	0.6655	0.102*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0607 (12)	0.1010 (6)	0.0588 (5)	−0.0165 (6)	−0.0109 (5)	−0.0190 (5)
Cl1B	0.0607 (12)	0.1010 (6)	0.0588 (5)	−0.0165 (6)	−0.0109 (5)	−0.0190 (5)
O1	0.088 (6)	0.100 (6)	0.068 (2)	0.018 (4)	−0.011 (3)	0.008 (3)
O2	0.141 (8)	0.076 (2)	0.130 (3)	−0.009 (4)	−0.021 (6)	0.021 (2)
N1	0.071 (4)	0.068 (2)	0.075 (3)	0.023 (2)	−0.011 (3)	−0.005 (2)
O1B	0.088 (6)	0.100 (6)	0.068 (2)	0.018 (4)	−0.011 (3)	0.008 (3)
O2B	0.141 (8)	0.076 (2)	0.130 (3)	−0.009 (4)	−0.021 (6)	0.021 (2)
N1B	0.071 (4)	0.068 (2)	0.075 (3)	0.023 (2)	−0.011 (3)	−0.005 (2)
C1	0.0257 (10)	0.0711 (16)	0.0463 (14)	0.0075 (10)	−0.0005 (10)	−0.0111 (13)
C2	0.0330 (12)	0.0761 (18)	0.0471 (14)	0.0110 (12)	−0.0037 (10)	−0.0142 (14)
C3	0.0463 (15)	0.0788 (19)	0.0505 (15)	0.0225 (14)	−0.0057 (12)	−0.0146 (15)
C4	0.0602 (17)	0.0701 (19)	0.0601 (18)	0.0332 (15)	0.0033 (15)	−0.0002 (15)
C5	0.0662 (19)	0.0567 (17)	0.079 (2)	0.0106 (14)	−0.0035 (17)	−0.0068 (16)
C6	0.0464 (14)	0.0732 (19)	0.0586 (17)	0.0057 (14)	−0.0091 (13)	−0.0124 (15)
C7	0.0284 (11)	0.0747 (17)	0.0404 (13)	−0.0032 (11)	−0.0024 (10)	−0.0109 (12)
O3	0.0297 (8)	0.1063 (15)	0.0571 (11)	−0.0049 (9)	0.0044 (8)	0.0005 (12)
O4	0.0413 (9)	0.0750 (13)	0.0440 (9)	0.0114 (9)	−0.0038 (8)	−0.0169 (9)
O5	0.0280 (7)	0.0430 (8)	0.0407 (8)	−0.0008 (6)	−0.0039 (6)	0.0031 (7)
N2	0.0275 (9)	0.0655 (14)	0.0384 (10)	−0.0050 (9)	−0.0011 (8)	−0.0050 (10)
N3	0.0375 (9)	0.0411 (10)	0.0318 (9)	0.0061 (8)	−0.0012 (8)	0.0013 (8)
N4	0.0298 (9)	0.0432 (10)	0.0521 (12)	−0.0032 (8)	−0.0044 (9)	0.0001 (10)
C8	0.0373 (12)	0.0565 (14)	0.0440 (13)	−0.0060 (11)	0.0017 (10)	−0.0014 (12)
C9	0.0383 (12)	0.0525 (13)	0.0352 (11)	0.0052 (10)	−0.0004 (9)	−0.0039 (11)
C10	0.0334 (11)	0.0482 (13)	0.0342 (11)	0.0029 (9)	−0.0056 (9)	−0.0047 (10)
C11	0.0282 (10)	0.0457 (12)	0.0400 (12)	0.0033 (9)	−0.0032 (9)	−0.0016 (10)
C12	0.0393 (12)	0.0460 (12)	0.0378 (12)	0.0059 (10)	0.0050 (10)	0.0019 (10)
C13	0.0482 (13)	0.0531 (14)	0.0470 (14)	0.0192 (12)	0.0032 (12)	0.0006 (12)
C14	0.0673 (17)	0.0557 (16)	0.0540 (16)	0.0224 (14)	0.0116 (14)	0.0021 (13)
C15	0.0818 (19)	0.0466 (14)	0.0549 (16)	0.0096 (13)	0.0141 (15)	−0.0024 (14)
C16	0.097 (2)	0.0436 (14)	0.069 (2)	0.0034 (15)	0.0223 (19)	0.0010 (15)
C17	0.085 (2)	0.0426 (14)	0.0550 (16)	0.0062 (14)	0.0222 (15)	0.0059 (12)
C18	0.0689 (17)	0.0510 (14)	0.0451 (14)	0.0261 (14)	0.0048 (13)	0.0117 (12)
C19	0.0580 (15)	0.0566 (15)	0.0369 (13)	0.0178 (12)	−0.0022 (12)	0.0067 (12)
C20	0.0301 (10)	0.0414 (11)	0.0348 (11)	0.0002 (9)	−0.0006 (9)	−0.0043 (9)
C21	0.0411 (13)	0.0378 (12)	0.0653 (17)	−0.0065 (10)	−0.0019 (12)	−0.0007 (12)
C22	0.0653 (18)	0.0512 (15)	0.087 (2)	0.0017 (14)	0.0045 (17)	−0.0127 (16)
C23	0.0665 (18)	0.0475 (14)	0.0678 (19)	−0.0086 (13)	−0.0126 (15)	0.0125 (14)
C24	0.0540 (16)	0.0529 (16)	0.098 (2)	−0.0193 (13)	−0.0009 (16)	0.0024 (17)

Geometric parameters (Å, º)

Cl1—C2	1.739 (3)	C11—C20	1.522 (3)
Cl1B—C2	1.716 (12)	C11—C12	1.536 (3)
O1—N1	1.207 (7)	C11—H11A	1.0000
O2—N1	1.217 (7)	C12—C13	1.529 (3)
N1—C4	1.482 (7)	C12—H12A	0.9900
O1B—N1B	1.226 (9)	C12—H12B	0.9900
O2B—N1B	1.228 (10)	C13—C14	1.534 (4)
N1B—C4	1.511 (9)	C13—C18	1.535 (4)
C1—C2	1.386 (3)	C13—H13A	1.0000
C1—C6	1.390 (4)	C14—C15	1.517 (4)
C1—C7	1.498 (4)	C14—H14A	0.9900
C2—C3	1.368 (4)	C14—H14B	0.9900
C3—C4	1.376 (5)	C15—C16	1.524 (4)
C3—H3A	0.9500	C15—H15A	0.9900
C4—C5	1.379 (5)	C15—H15B	0.9900
C5—C6	1.368 (4)	C16—C17	1.525 (4)
C5—H5A	0.9500	C16—H16A	0.9900
C6—H6A	0.9500	C16—H16B	0.9900
C7—O3	1.228 (3)	C17—C18	1.514 (4)
C7—N2	1.333 (3)	C17—H17A	0.9900
O4—C9	1.418 (3)	C17—H17B	0.9900
O4—H4B	0.87 (4)	C18—C19	1.525 (4)
O5—C20	1.244 (2)	C18—H18A	1.0000
N2—C8	1.455 (3)	C19—H19A	0.9900
N2—H2	0.83 (3)	C19—H19B	0.9900
N3—C11	1.467 (3)	C21—C22	1.514 (4)
N3—C10	1.467 (3)	C21—C23	1.526 (4)
N3—C19	1.471 (3)	C21—C24	1.528 (3)
N4—C20	1.329 (3)	C22—H22A	0.9800
N4—C21	1.487 (3)	C22—H22B	0.9800
N4—H4	0.84 (3)	C22—H22C	0.9800
C8—C9	1.517 (3)	C23—H23A	0.9800
C8—H8A	0.9900	C23—H23B	0.9800
C8—H8B	0.9900	C23—H23C	0.9800
C9—C10	1.531 (3)	C24—H24A	0.9800
C9—H9A	1.0000	C24—H24B	0.9800
C10—H10A	0.9900	C24—H24C	0.9800
C10—H10B	0.9900
O1—N1—O2	127.3 (9)	H12A—C12—H12B	107.9
O1—N1—C4	121.0 (9)	C12—C13—C14	112.2 (2)
O2—N1—C4	111.6 (9)	C12—C13—C18	110.74 (19)
O1B—N1B—O2B	120.6 (14)	C14—C13—C18	111.5 (2)
O1B—N1B—C4	111.2 (14)	C12—C13—H13A	107.4
O2B—N1B—C4	128.1 (14)	C14—C13—H13A	107.4
C2—C1—C6	118.1 (3)	C18—C13—H13A	107.4
C2—C1—C7	122.7 (2)	C15—C14—C13	113.9 (2)
C6—C1—C7	119.2 (2)	C15—C14—H14A	108.8
C3—C2—C1	121.9 (3)	C13—C14—H14A	108.8
C3—C2—Cl1B	120.7 (7)	C15—C14—H14B	108.8
C1—C2—Cl1B	113.0 (8)	C13—C14—H14B	108.8
C3—C2—Cl1	118.2 (2)	H14A—C14—H14B	107.7
C1—C2—Cl1	119.8 (2)	C14—C15—C16	110.9 (3)
C2—C3—C4	117.6 (3)	C14—C15—H15A	109.5
C2—C3—H3A	121.2	C16—C15—H15A	109.5
C4—C3—H3A	121.2	C14—C15—H15B	109.5
C3—C4—C5	123.0 (3)	C16—C15—H15B	109.5
C3—C4—N1	113.4 (5)	H15A—C15—H15B	108.0
C5—C4—N1	123.7 (5)	C15—C16—C17	109.9 (2)
C3—C4—N1B	128.6 (7)	C15—C16—H16A	109.7
C5—C4—N1B	108.1 (7)	C17—C16—H16A	109.7
C6—C5—C4	117.7 (3)	C15—C16—H16B	109.7
C6—C5—H5A	121.1	C17—C16—H16B	109.7
C4—C5—H5A	121.1	H16A—C16—H16B	108.2
C5—C6—C1	121.6 (3)	C18—C17—C16	112.2 (3)
C5—C6—H6A	119.2	C18—C17—H17A	109.2
C1—C6—H6A	119.2	C16—C17—H17A	109.2
O3—C7—N2	124.9 (3)	C18—C17—H17B	109.2
O3—C7—C1	121.2 (2)	C16—C17—H17B	109.2
N2—C7—C1	113.9 (2)	H17A—C17—H17B	107.9
C9—O4—H4B	109 (2)	C17—C18—C19	111.8 (2)
C7—N2—C8	124.3 (2)	C17—C18—C13	112.8 (2)
C7—N2—H2	118 (2)	C19—C18—C13	110.4 (2)
C8—N2—H2	117 (2)	C17—C18—H18A	107.2
C11—N3—C10	114.32 (17)	C19—C18—H18A	107.2
C11—N3—C19	108.55 (18)	C13—C18—H18A	107.2
C10—N3—C19	110.33 (18)	N3—C19—C18	112.3 (2)
C20—N4—C21	126.27 (19)	N3—C19—H19A	109.2
C20—N4—H4	115 (2)	C18—C19—H19A	109.2
C21—N4—H4	119 (2)	N3—C19—H19B	109.2
N2—C8—C9	112.7 (2)	C18—C19—H19B	109.2
N2—C8—H8A	109.1	H19A—C19—H19B	107.9
C9—C8—H8A	109.1	O5—C20—N4	123.7 (2)
N2—C8—H8B	109.1	O5—C20—C11	120.82 (19)
C9—C8—H8B	109.1	N4—C20—C11	115.44 (18)
H8A—C8—H8B	107.8	N4—C21—C22	108.9 (2)
O4—C9—C8	107.70 (19)	N4—C21—C23	110.9 (2)
O4—C9—C10	109.00 (19)	C22—C21—C23	111.9 (2)
C8—C9—C10	113.42 (19)	N4—C21—C24	106.1 (2)
O4—C9—H9A	108.9	C22—C21—C24	109.8 (2)
C8—C9—H9A	108.9	C23—C21—C24	109.2 (2)
C10—C9—H9A	108.9	C21—C22—H22A	109.5
N3—C10—C9	113.06 (18)	C21—C22—H22B	109.5
N3—C10—H10A	109.0	H22A—C22—H22B	109.5
C9—C10—H10A	109.0	C21—C22—H22C	109.5
N3—C10—H10B	109.0	H22A—C22—H22C	109.5
C9—C10—H10B	109.0	H22B—C22—H22C	109.5
H10A—C10—H10B	107.8	C21—C23—H23A	109.5
N3—C11—C20	111.60 (17)	C21—C23—H23B	109.5
N3—C11—C12	108.59 (18)	H23A—C23—H23B	109.5
C20—C11—C12	108.67 (18)	C21—C23—H23C	109.5
N3—C11—H11A	109.3	H23A—C23—H23C	109.5
C20—C11—H11A	109.3	H23B—C23—H23C	109.5
C12—C11—H11A	109.3	C21—C24—H24A	109.5
C13—C12—C11	111.81 (19)	C21—C24—H24B	109.5
C13—C12—H12A	109.3	H24A—C24—H24B	109.5
C11—C12—H12A	109.3	C21—C24—H24C	109.5
C13—C12—H12B	109.3	H24A—C24—H24C	109.5
C11—C12—H12B	109.3	H24B—C24—H24C	109.5
C6—C1—C2—C3	1.8 (4)	C19—N3—C10—C9	−77.0 (2)
C7—C1—C2—C3	−177.6 (2)	O4—C9—C10—N3	−165.33 (18)
C6—C1—C2—Cl1B	158.4 (14)	C8—C9—C10—N3	−45.4 (3)
C7—C1—C2—Cl1B	−20.9 (14)	C10—N3—C11—C20	−52.4 (2)
C6—C1—C2—Cl1	179.7 (2)	C19—N3—C11—C20	−176.07 (18)
C7—C1—C2—Cl1	0.3 (3)	C10—N3—C11—C12	−172.21 (17)
C1—C2—C3—C4	−2.3 (4)	C19—N3—C11—C12	64.2 (2)
Cl1B—C2—C3—C4	−157.2 (15)	N3—C11—C12—C13	−59.4 (2)
Cl1—C2—C3—C4	179.8 (2)	C20—C11—C12—C13	178.98 (19)
C2—C3—C4—C5	0.7 (4)	C11—C12—C13—C14	176.8 (2)
C2—C3—C4—N1	−179.8 (5)	C11—C12—C13—C18	51.5 (3)
C2—C3—C4—N1B	173.4 (9)	C12—C13—C14—C15	−75.8 (3)
O1—N1—C4—C3	−9.0 (13)	C18—C13—C14—C15	49.0 (3)
O2—N1—C4—C3	168.9 (8)	C13—C14—C15—C16	−54.1 (3)
O1—N1—C4—C5	170.5 (10)	C14—C15—C16—C17	57.2 (3)
O2—N1—C4—C5	−11.6 (11)	C15—C16—C17—C18	−57.7 (3)
O1B—N1B—C4—C3	1 (2)	C16—C17—C18—C19	178.8 (2)
O2B—N1B—C4—C3	−175.8 (15)	C16—C17—C18—C13	53.7 (3)
O1B—N1B—C4—C5	174.8 (17)	C12—C13—C18—C17	77.4 (3)
O2B—N1B—C4—C5	−2 (2)	C14—C13—C18—C17	−48.3 (3)
C3—C4—C5—C6	1.4 (4)	C12—C13—C18—C19	−48.5 (3)
N1—C4—C5—C6	−178.1 (6)	C14—C13—C18—C19	−174.2 (2)
N1B—C4—C5—C6	−172.6 (8)	C11—N3—C19—C18	−64.1 (3)
C4—C5—C6—C1	−2.0 (4)	C10—N3—C19—C18	170.0 (2)
C2—C1—C6—C5	0.5 (4)	C17—C18—C19—N3	−70.8 (3)
C7—C1—C6—C5	179.9 (2)	C13—C18—C19—N3	55.7 (3)
C2—C1—C7—O3	−65.7 (3)	C21—N4—C20—O5	4.6 (4)
C6—C1—C7—O3	115.0 (3)	C21—N4—C20—C11	−177.1 (2)
C2—C1—C7—N2	115.6 (3)	N3—C11—C20—O5	−41.3 (3)
C6—C1—C7—N2	−63.7 (3)	C12—C11—C20—O5	78.4 (3)
O3—C7—N2—C8	−1.1 (4)	N3—C11—C20—N4	140.4 (2)
C1—C7—N2—C8	177.5 (2)	C12—C11—C20—N4	−99.9 (2)
C7—N2—C8—C9	−122.8 (3)	C20—N4—C21—C22	64.5 (3)
N2—C8—C9—O4	69.4 (2)	C20—N4—C21—C23	−59.1 (3)
N2—C8—C9—C10	−51.3 (3)	C20—N4—C21—C24	−177.5 (2)
C11—N3—C10—C9	160.33 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4B···O5^i	0.87 (4)	1.94 (4)	2.791 (2)	169 (3)
N2—H2···O5	0.83 (3)	2.11 (3)	2.928 (3)	169 (3)
N4—H4···O3^ii	0.84 (3)	2.15 (3)	2.964 (2)	161 (3)

Symmetry codes: (i) x, y, z+1; (ii) x+1/2, −y+3/2, −z+2.

(II) (3S,4aS,8aS)-N-tert-Butyl-2-{(S)-2-[(S)-1-(2-chloro-4-nitrobenzoyl)pyrrolidin-2-yl]-2-hydroxyethyl}decahydroisoquinoline-3-carboxamide

Crystal data

C27H39ClN4O5	F(000) = 572
Mr = 535.07	Dx = 1.279 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 7806 reflections
a = 6.4341 (7) Å	θ = 2.8–26.3°
b = 20.280 (2) Å	µ = 0.18 mm^−1
c = 11.0377 (12) Å	T = 168 K
β = 105.248 (1)°	Plates, colourless
V = 1389.5 (3) Å^3	0.86 × 0.65 × 0.15 mm
Z = 2

Data collection

Siemens Platform/APEXII CCD diffractometer	5627 independent reflections
Radiation source: normal-focus sealed tube	5222 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
profile data from φ and ω scans	θmax = 26.4°, θmin = 1.9°
Absorption correction: integration (SHELXTL/XPREP; Bruker, 2014)	h = −8→8
Tmin = 0.892, Tmax = 0.980	k = −25→25
16374 measured reflections	l = −13→13

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.032	w = 1/[σ^2(Fo^2) + (0.0447P)^2 + 0.1276P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.082	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.24 e Å^−3
5627 reflections	Δρmin = −0.21 e Å^−3
377 parameters	Absolute structure: Flack (1983); Hooft et al. (2008); 2720 Friedels
14 restraints	Absolute structure parameter: 0.036 (19)

Special details

Experimental. One distinct cell was identified using APEX2 (Bruker, 2014). Four frame series were integrated and filtered for statistical outliers using SAINT (Bruker, 2014) then corrected for absorption by integration using SHELXTL/XPREP V2005/2 (Bruker, 2014) before using SAINT/SADABS (Bruker, 2014) to sort, merge, and scale the combined data. No decay correction was applied.

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. Structure was phased by direct (Sheldrick, 2015) methods. Systematic conditions suggested the ambiguous space group. The space group choice was confirmed by successful convergence of the full-matrix least-squares refinement on F². The final map had no significant features. A final analysis of variance between observed and calculated structure factors showed little dependence on amplitude and resolution.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.18218 (12)	0.27617 (3)	0.58986 (6)	0.05313 (19)
O1	0.7185 (5)	0.41190 (18)	0.9393 (3)	0.0657 (8)	0.967 (8)
O2	0.5309 (5)	0.48339 (16)	1.0083 (3)	0.0796 (11)	0.967 (8)
O1B	0.658 (13)	0.391 (2)	0.970 (8)	0.0657 (8)	0.033 (8)
O2B	0.605 (14)	0.4966 (13)	0.961 (9)	0.0796 (11)	0.033 (8)
N1	0.5493 (4)	0.43973 (13)	0.9347 (2)	0.0521 (6)
O3	−0.3816 (17)	0.3687 (9)	0.5659 (16)	0.064 (2)	0.58 (2)
C7	−0.1974 (15)	0.3696 (13)	0.5438 (6)	0.044 (3)	0.58 (2)
O3B	−0.341 (3)	0.3487 (9)	0.584 (2)	0.064 (2)	0.42 (2)
C7B	−0.209 (2)	0.3832 (18)	0.5437 (8)	0.044 (3)	0.42 (2)
O4	−0.0271 (3)	0.50975 (9)	0.45504 (16)	0.0466 (4)
H4B	−0.124 (4)	0.5375 (14)	0.441 (3)	0.070*
O5	0.6776 (3)	0.60681 (10)	0.43924 (17)	0.0497 (5)
N2	−0.1962 (3)	0.38062 (11)	0.4242 (2)	0.0434 (5)
N3	0.1541 (3)	0.56188 (9)	0.25105 (17)	0.0349 (4)
N4	0.3515 (3)	0.61688 (10)	0.48165 (17)	0.0354 (4)
H4C	0.211 (5)	0.6126 (16)	0.452 (3)	0.053*
C1	0.1816 (4)	0.34965 (12)	0.6715 (2)	0.0407 (6)
C2	0.3653 (5)	0.36560 (13)	0.7648 (2)	0.0419 (5)
H2A	0.4918	0.3393	0.7794	0.050*
C3	0.3571 (4)	0.42136 (13)	0.8359 (2)	0.0425 (6)
C4	0.1757 (5)	0.46054 (15)	0.8176 (3)	0.0515 (7)
H4A	0.1728	0.4977	0.8697	0.062*
C5	−0.0004 (5)	0.44390 (15)	0.7217 (3)	0.0505 (6)
H5A	−0.1264	0.4703	0.7071	0.061*
C6	0.0008 (4)	0.38941 (13)	0.6450 (2)	0.0417 (6)
C8	−0.0147 (4)	0.40027 (12)	0.3737 (2)	0.0355 (5)
H8A	0.1254	0.3883	0.4342	0.043*
C9	−0.0526 (4)	0.35761 (14)	0.2539 (3)	0.0481 (6)
H9A	−0.0348	0.3849	0.1829	0.058*
H9B	0.0544	0.3214	0.2674	0.058*
C10	−0.2747 (10)	0.3296 (4)	0.2237 (6)	0.0504 (15)	0.669 (16)
H10A	−0.2719	0.2816	0.2401	0.060*	0.669 (16)
H10B	−0.3527	0.3379	0.1350	0.060*	0.669 (16)
C11	−0.3755 (11)	0.3670 (4)	0.3125 (7)	0.0423 (15)	0.669 (16)
H11A	−0.4415	0.4086	0.2737	0.051*	0.669 (16)
H11B	−0.4878	0.3400	0.3353	0.051*	0.669 (16)
C10B	−0.2980 (17)	0.3525 (8)	0.2257 (15)	0.0504 (15)	0.331 (16)
H10C	−0.3618	0.3898	0.1705	0.060*	0.331 (16)
H10D	−0.3439	0.3114	0.1777	0.060*	0.331 (16)
C11B	−0.392 (2)	0.3527 (9)	0.3383 (12)	0.0423 (15)	0.331 (16)
H11C	−0.5191	0.3818	0.3268	0.051*	0.331 (16)
H11D	−0.4263	0.3079	0.3630	0.051*	0.331 (16)
C12	−0.0208 (4)	0.47423 (12)	0.3446 (2)	0.0370 (5)
H12A	−0.1522	0.4846	0.2757	0.044*
C13	0.1800 (4)	0.49527 (12)	0.3056 (2)	0.0380 (5)
H13A	0.3061	0.4945	0.3799	0.046*
H13B	0.2073	0.4636	0.2433	0.046*
C14	0.3607 (3)	0.59631 (12)	0.2673 (2)	0.0357 (5)
H14A	0.4542	0.5706	0.2250	0.043*
C15	0.3232 (4)	0.66580 (12)	0.2091 (2)	0.0369 (5)
H15A	0.2424	0.6925	0.2564	0.044*
H15B	0.4642	0.6874	0.2172	0.044*
C16	0.1982 (4)	0.66434 (13)	0.0704 (2)	0.0380 (5)
H16A	0.2901	0.6415	0.0230	0.046*
C17	0.1487 (4)	0.73367 (15)	0.0150 (2)	0.0462 (6)
H17A	0.2833	0.7598	0.0349	0.055*
H17B	0.0968	0.7302	−0.0776	0.055*
C18	−0.0196 (4)	0.76982 (15)	0.0644 (2)	0.0470 (6)
H18A	0.0388	0.7786	0.1552	0.056*
H18B	−0.0528	0.8127	0.0209	0.056*
C19	−0.2244 (4)	0.72936 (14)	0.0435 (2)	0.0451 (6)
H19A	−0.2910	0.7249	−0.0478	0.054*
H19B	−0.3279	0.7527	0.0807	0.054*
C20	−0.1805 (4)	0.66089 (12)	0.1020 (2)	0.0381 (5)
H20A	−0.3159	0.6351	0.0816	0.046*
H20B	−0.1306	0.6652	0.1945	0.046*
C21	−0.0090 (4)	0.62377 (13)	0.0539 (2)	0.0374 (5)
H21A	−0.0699	0.6159	−0.0380	0.045*
C22	0.0428 (4)	0.55715 (13)	0.1167 (2)	0.0396 (5)
H22A	−0.0929	0.5322	0.1070	0.048*
H22B	0.1344	0.5321	0.0736	0.048*
C23	0.4782 (3)	0.60558 (11)	0.4055 (2)	0.0359 (5)
C24	0.4216 (4)	0.62935 (12)	0.6177 (2)	0.0390 (5)
C25	0.2182 (7)	0.6384 (4)	0.6614 (5)	0.0498 (13)	0.811 (17)
H25A	0.1300	0.5984	0.6430	0.075*	0.811 (17)
H25B	0.1361	0.6760	0.6173	0.075*	0.811 (17)
H25C	0.2573	0.6467	0.7521	0.075*	0.811 (17)
C26	0.5534 (13)	0.5704 (3)	0.6839 (4)	0.0572 (14)	0.811 (17)
H26A	0.4678	0.5300	0.6631	0.086*	0.811 (17)
H26B	0.5913	0.5773	0.7750	0.086*	0.811 (17)
H26C	0.6853	0.5662	0.6559	0.086*	0.811 (17)
C27	0.5599 (11)	0.6921 (3)	0.6388 (7)	0.0569 (15)	0.811 (17)
H27A	0.4787	0.7283	0.5894	0.085*	0.811 (17)
H27B	0.6918	0.6842	0.6124	0.085*	0.811 (17)
H27C	0.5977	0.7037	0.7281	0.085*	0.811 (17)
C25B	0.227 (4)	0.6608 (14)	0.651 (3)	0.0498 (13)	0.189 (17)
H25D	0.0945	0.6390	0.6040	0.075*	0.189 (17)
H25E	0.2201	0.7078	0.6299	0.075*	0.189 (17)
H25F	0.2418	0.6558	0.7415	0.075*	0.189 (17)
C26B	0.461 (5)	0.5602 (8)	0.678 (2)	0.0572 (14)	0.189 (17)
H26D	0.3258	0.5351	0.6569	0.086*	0.189 (17)
H26E	0.5122	0.5647	0.7697	0.086*	0.189 (17)
H26F	0.5692	0.5369	0.6465	0.086*	0.189 (17)
C27B	0.612 (4)	0.6761 (14)	0.659 (3)	0.0569 (15)	0.189 (17)
H27D	0.7446	0.6534	0.6543	0.085*	0.189 (17)
H27E	0.6262	0.6903	0.7457	0.085*	0.189 (17)
H27F	0.5895	0.7148	0.6037	0.085*	0.189 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0715 (4)	0.0369 (3)	0.0546 (4)	−0.0005 (3)	0.0230 (3)	−0.0055 (3)
O1	0.0580 (14)	0.0857 (18)	0.0498 (14)	0.0073 (14)	0.0076 (10)	−0.0005 (13)
O2	0.0664 (16)	0.097 (2)	0.0719 (18)	−0.0101 (14)	0.0123 (14)	−0.0422 (16)
O1B	0.0580 (14)	0.0857 (18)	0.0498 (14)	0.0073 (14)	0.0076 (10)	−0.0005 (13)
O2B	0.0664 (16)	0.097 (2)	0.0719 (18)	−0.0101 (14)	0.0123 (14)	−0.0422 (16)
N1	0.0564 (14)	0.0602 (15)	0.0405 (12)	−0.0036 (12)	0.0143 (10)	0.0005 (11)
O3	0.041 (4)	0.092 (8)	0.068 (4)	−0.008 (3)	0.029 (4)	−0.011 (4)
C7	0.0435 (16)	0.040 (10)	0.0557 (16)	−0.004 (3)	0.0269 (13)	−0.0166 (16)
O3B	0.041 (4)	0.092 (8)	0.068 (4)	−0.008 (3)	0.029 (4)	−0.011 (4)
C7B	0.0435 (16)	0.040 (10)	0.0557 (16)	−0.004 (3)	0.0269 (13)	−0.0166 (16)
O4	0.0528 (11)	0.0454 (10)	0.0399 (10)	0.0172 (8)	0.0090 (8)	−0.0097 (8)
O5	0.0298 (8)	0.0613 (12)	0.0524 (11)	0.0106 (8)	0.0011 (7)	−0.0171 (9)
N2	0.0344 (11)	0.0495 (13)	0.0480 (12)	−0.0039 (9)	0.0136 (9)	−0.0135 (10)
N3	0.0322 (10)	0.0374 (11)	0.0333 (10)	0.0008 (8)	0.0054 (8)	−0.0082 (8)
N4	0.0306 (9)	0.0423 (11)	0.0300 (10)	0.0024 (8)	0.0022 (7)	−0.0053 (8)
C1	0.0582 (15)	0.0342 (12)	0.0379 (13)	−0.0028 (11)	0.0273 (12)	−0.0015 (10)
C2	0.0528 (14)	0.0417 (13)	0.0363 (12)	0.0041 (11)	0.0208 (11)	0.0064 (10)
C3	0.0525 (14)	0.0448 (14)	0.0336 (12)	−0.0042 (11)	0.0174 (10)	0.0019 (10)
C4	0.0611 (17)	0.0552 (16)	0.0424 (15)	0.0031 (13)	0.0213 (13)	−0.0126 (12)
C5	0.0487 (15)	0.0599 (17)	0.0469 (15)	0.0071 (13)	0.0196 (12)	−0.0097 (13)
C6	0.0450 (14)	0.0477 (14)	0.0394 (13)	−0.0040 (11)	0.0233 (11)	−0.0054 (11)
C8	0.0330 (11)	0.0394 (12)	0.0350 (12)	0.0029 (9)	0.0104 (9)	−0.0048 (10)
C9	0.0539 (15)	0.0443 (14)	0.0461 (15)	0.0056 (12)	0.0131 (12)	−0.0130 (12)
C10	0.073 (2)	0.037 (4)	0.0420 (16)	−0.021 (3)	0.0166 (17)	−0.018 (3)
C11	0.0325 (16)	0.035 (3)	0.058 (3)	−0.0071 (18)	0.0089 (19)	−0.004 (2)
C10B	0.073 (2)	0.037 (4)	0.0420 (16)	−0.021 (3)	0.0166 (17)	−0.018 (3)
C11B	0.0325 (16)	0.035 (3)	0.058 (3)	−0.0071 (18)	0.0089 (19)	−0.004 (2)
C12	0.0375 (12)	0.0394 (12)	0.0330 (11)	0.0083 (10)	0.0072 (9)	−0.0068 (9)
C13	0.0360 (12)	0.0345 (12)	0.0410 (12)	0.0050 (9)	0.0059 (9)	−0.0089 (10)
C14	0.0265 (10)	0.0438 (13)	0.0364 (12)	0.0029 (9)	0.0077 (9)	−0.0106 (9)
C15	0.0291 (11)	0.0472 (14)	0.0357 (12)	−0.0043 (10)	0.0111 (9)	−0.0062 (10)
C16	0.0304 (11)	0.0535 (15)	0.0325 (12)	−0.0009 (10)	0.0128 (9)	−0.0049 (10)
C17	0.0409 (13)	0.0614 (16)	0.0383 (13)	−0.0066 (12)	0.0139 (10)	0.0040 (12)
C18	0.0487 (14)	0.0487 (14)	0.0450 (14)	−0.0002 (12)	0.0148 (11)	0.0057 (12)
C19	0.0378 (13)	0.0583 (16)	0.0398 (13)	0.0056 (12)	0.0111 (10)	0.0010 (12)
C20	0.0272 (10)	0.0520 (14)	0.0355 (12)	−0.0009 (10)	0.0089 (9)	−0.0009 (10)
C21	0.0322 (11)	0.0523 (14)	0.0267 (11)	−0.0045 (10)	0.0061 (8)	−0.0095 (10)
C22	0.0365 (12)	0.0462 (14)	0.0346 (12)	−0.0017 (10)	0.0066 (9)	−0.0137 (10)
C23	0.0315 (11)	0.0353 (12)	0.0387 (12)	0.0057 (9)	0.0052 (9)	−0.0079 (10)
C24	0.0422 (13)	0.0420 (13)	0.0295 (11)	0.0017 (10)	0.0037 (9)	−0.0019 (9)
C25	0.0545 (17)	0.062 (4)	0.0341 (18)	−0.001 (2)	0.0141 (12)	−0.008 (3)
C26	0.054 (3)	0.066 (2)	0.0469 (18)	0.007 (2)	0.005 (2)	0.0227 (17)
C27	0.072 (3)	0.058 (3)	0.039 (3)	−0.015 (3)	0.012 (2)	−0.015 (2)
C25B	0.0545 (17)	0.062 (4)	0.0341 (18)	−0.001 (2)	0.0141 (12)	−0.008 (3)
C26B	0.054 (3)	0.066 (2)	0.0469 (18)	0.007 (2)	0.005 (2)	0.0227 (17)
C27B	0.072 (3)	0.058 (3)	0.039 (3)	−0.015 (3)	0.012 (2)	−0.015 (2)

Geometric parameters (Å, º)

Cl1—C1	1.742 (2)	C12—H12A	1.0000
O1—N1	1.215 (3)	C13—H13A	0.9900
O2—N1	1.228 (3)	C13—H13B	0.9900
O1B—N1	1.210 (15)	C14—C23	1.525 (3)
O2B—N1	1.219 (15)	C14—C15	1.541 (3)
N1—C3	1.466 (3)	C14—H14A	1.0000
O3—C7B	1.236 (18)	C15—C16	1.531 (3)
O3—C7	1.271 (11)	C15—H15A	0.9900
C7—O3B	1.20 (2)	C15—H15B	0.9900
C7—N2	1.341 (7)	C16—C17	1.533 (4)
C7—C6	1.512 (7)	C16—C21	1.536 (3)
O3B—C7B	1.271 (14)	C16—H16A	1.0000
C7B—N2	1.343 (10)	C17—C18	1.522 (4)
C7B—C6	1.513 (10)	C17—H17A	0.9900
O4—C12	1.425 (3)	C17—H17B	0.9900
O4—H4B	0.824 (14)	C18—C19	1.518 (4)
O5—C23	1.239 (3)	C18—H18A	0.9900
N2—C8	1.475 (3)	C18—H18B	0.9900
N2—C11	1.476 (5)	C19—C20	1.526 (4)
N2—C11B	1.477 (10)	C19—H19A	0.9900
N3—C22	1.470 (3)	C19—H19B	0.9900
N3—C14	1.470 (3)	C20—C21	1.541 (3)
N3—C13	1.471 (3)	C20—H20A	0.9900
N4—C23	1.336 (3)	C20—H20B	0.9900
N4—C24	1.472 (3)	C21—C22	1.515 (4)
N4—H4C	0.88 (3)	C21—H21A	1.0000
C1—C6	1.382 (4)	C22—H22A	0.9900
C1—C2	1.387 (4)	C22—H22B	0.9900
C2—C3	1.385 (4)	C24—C25	1.520 (4)
C2—H2A	0.9500	C24—C27B	1.524 (13)
C3—C4	1.382 (4)	C24—C27	1.535 (5)
C4—C5	1.374 (4)	C24—C26	1.535 (4)
C4—H4A	0.9500	C24—C25B	1.536 (13)
C5—C6	1.393 (4)	C24—C26B	1.545 (12)
C5—H5A	0.9500	C25—H25A	0.9800
C8—C12	1.532 (3)	C25—H25B	0.9800
C8—C9	1.545 (3)	C25—H25C	0.9800
C8—H8A	1.0000	C26—H26A	0.9800
C9—C10	1.492 (6)	C26—H26B	0.9800
C9—C10B	1.531 (11)	C26—H26C	0.9800
C9—H9A	0.9900	C27—H27A	0.9800
C9—H9B	0.9900	C27—H27B	0.9800
C10—C11	1.514 (7)	C27—H27C	0.9800
C10—H10A	0.9900	C25B—H25D	0.9800
C10—H10B	0.9900	C25B—H25E	0.9800
C11—H11A	0.9900	C25B—H25F	0.9800
C11—H11B	0.9900	C26B—H26D	0.9800
C10B—C11B	1.519 (11)	C26B—H26E	0.9800
C10B—H10C	0.9900	C26B—H26F	0.9800
C10B—H10D	0.9900	C27B—H27D	0.9800
C11B—H11C	0.9900	C27B—H27E	0.9800
C11B—H11D	0.9900	C27B—H27F	0.9800
C12—C13	1.526 (3)
O1B—N1—O2B	126 (3)	N3—C14—C23	112.03 (19)
O1—N1—O2	123.3 (3)	N3—C14—C15	110.24 (17)
O1B—N1—C3	110 (3)	C23—C14—C15	106.64 (18)
O1—N1—C3	119.0 (2)	N3—C14—H14A	109.3
O2B—N1—C3	124 (3)	C23—C14—H14A	109.3
O2—N1—C3	117.8 (3)	C15—C14—H14A	109.3
C7B—O3—C7	13 (3)	C16—C15—C14	112.51 (19)
O3B—C7—O3	22.9 (9)	C16—C15—H15A	109.1
O3B—C7—N2	128.8 (12)	C14—C15—H15A	109.1
O3—C7—N2	116.0 (12)	C16—C15—H15B	109.1
O3B—C7—C6	113.6 (12)	C14—C15—H15B	109.1
O3—C7—C6	120.7 (10)	H15A—C15—H15B	107.8
N2—C7—C6	117.5 (7)	C15—C16—C17	112.4 (2)
C7—O3B—C7B	13 (3)	C15—C16—C21	109.89 (19)
O3—C7B—O3B	22.8 (9)	C17—C16—C21	111.2 (2)
O3—C7B—N2	118.4 (11)	C15—C16—H16A	107.7
O3B—C7B—N2	122.9 (19)	C17—C16—H16A	107.7
O3—C7B—C6	123.1 (11)	C21—C16—H16A	107.7
O3B—C7B—C6	109.5 (15)	C18—C17—C16	113.0 (2)
N2—C7B—C6	117.2 (9)	C18—C17—H17A	109.0
C12—O4—H4B	112 (2)	C16—C17—H17A	109.0
C7—N2—C7B	12 (3)	C18—C17—H17B	109.0
C7—N2—C8	128.8 (4)	C16—C17—H17B	109.0
C7B—N2—C8	128.2 (5)	H17A—C17—H17B	107.8
C7—N2—C11	125.8 (5)	C19—C18—C17	110.9 (2)
C8—N2—C11	105.0 (4)	C19—C18—H18A	109.5
C7—N2—C11B	110.1 (7)	C17—C18—H18A	109.5
C7B—N2—C11B	112.6 (8)	C19—C18—H18B	109.5
C8—N2—C11B	119.2 (6)	C17—C18—H18B	109.5
C22—N3—C14	109.84 (18)	H18A—C18—H18B	108.1
C22—N3—C13	109.01 (18)	C18—C19—C20	111.8 (2)
C14—N3—C13	112.62 (18)	C18—C19—H19A	109.3
C23—N4—C24	126.7 (2)	C20—C19—H19A	109.3
C23—N4—H4C	118.8 (19)	C18—C19—H19B	109.3
C24—N4—H4C	114.2 (19)	C20—C19—H19B	109.3
C6—C1—C2	121.8 (2)	H19A—C19—H19B	107.9
C6—C1—Cl1	120.4 (2)	C19—C20—C21	111.6 (2)
C2—C1—Cl1	117.8 (2)	C19—C20—H20A	109.3
C3—C2—C1	117.3 (2)	C21—C20—H20A	109.3
C3—C2—H2A	121.3	C19—C20—H20B	109.3
C1—C2—H2A	121.3	C21—C20—H20B	109.3
C4—C3—C2	122.9 (2)	H20A—C20—H20B	108.0
C4—C3—N1	118.5 (2)	C22—C21—C16	110.13 (19)
C2—C3—N1	118.6 (2)	C22—C21—C20	111.7 (2)
C5—C4—C3	117.7 (2)	C16—C21—C20	112.0 (2)
C5—C4—H4A	121.2	C22—C21—H21A	107.6
C3—C4—H4A	121.2	C16—C21—H21A	107.6
C4—C5—C6	121.9 (3)	C20—C21—H21A	107.6
C4—C5—H5A	119.1	N3—C22—C21	113.16 (18)
C6—C5—H5A	119.1	N3—C22—H22A	108.9
C1—C6—C5	118.2 (2)	C21—C22—H22A	108.9
C1—C6—C7	120.0 (10)	N3—C22—H22B	108.9
C5—C6—C7	121.4 (9)	C21—C22—H22B	108.9
C1—C6—C7B	130.1 (13)	H22A—C22—H22B	107.8
C5—C6—C7B	111.7 (13)	O5—C23—N4	124.3 (2)
C7—C6—C7B	11 (2)	O5—C23—C14	120.3 (2)
N2—C8—C12	111.36 (19)	N4—C23—C14	115.23 (18)
N2—C8—C9	102.10 (19)	N4—C24—C25	106.6 (3)
C12—C8—C9	112.3 (2)	N4—C24—C27B	114.8 (14)
N2—C8—H8A	110.3	N4—C24—C27	107.9 (3)
C12—C8—H8A	110.3	C25—C24—C27	111.4 (4)
C9—C8—H8A	110.3	N4—C24—C26	109.6 (3)
C10—C9—C8	109.3 (3)	C25—C24—C26	110.9 (3)
C10B—C9—C8	97.7 (6)	C27—C24—C26	110.3 (3)
C10—C9—H9A	109.8	N4—C24—C25B	105.5 (12)
C8—C9—H9A	109.8	C27B—C24—C25B	108.3 (18)
C10—C9—H9B	109.8	N4—C24—C26B	104.9 (9)
C8—C9—H9B	109.8	C27B—C24—C26B	114.1 (13)
H9A—C9—H9B	108.3	C25B—C24—C26B	108.9 (13)
C9—C10—C11	102.3 (6)	C24—C25—H25A	109.5
C9—C10—H10A	111.3	C24—C25—H25B	109.5
C11—C10—H10A	111.3	H25A—C25—H25B	109.5
C9—C10—H10B	111.3	C24—C25—H25C	109.5
C11—C10—H10B	111.3	H25A—C25—H25C	109.5
H10A—C10—H10B	109.2	H25B—C25—H25C	109.5
N2—C11—C10	105.1 (5)	C24—C26—H26A	109.5
N2—C11—H11A	110.7	C24—C26—H26B	109.5
C10—C11—H11A	110.7	H26A—C26—H26B	109.5
N2—C11—H11B	110.7	C24—C26—H26C	109.5
C10—C11—H11B	110.7	H26A—C26—H26C	109.5
H11A—C11—H11B	108.8	H26B—C26—H26C	109.5
C11B—C10B—C9	116.4 (11)	C24—C27—H27A	109.5
C11B—C10B—H10C	108.2	C24—C27—H27B	109.5
C9—C10B—H10C	108.2	H27A—C27—H27B	109.5
C11B—C10B—H10D	108.2	C24—C27—H27C	109.5
C9—C10B—H10D	108.2	H27A—C27—H27C	109.5
H10C—C10B—H10D	107.3	H27B—C27—H27C	109.5
N2—C11B—C10B	94.0 (9)	C24—C25B—H25D	109.5
N2—C11B—H11C	112.9	C24—C25B—H25E	109.5
C10B—C11B—H11C	112.9	H25D—C25B—H25E	109.5
N2—C11B—H11D	112.9	C24—C25B—H25F	109.5
C10B—C11B—H11D	112.9	H25D—C25B—H25F	109.5
H11C—C11B—H11D	110.3	H25E—C25B—H25F	109.5
O4—C12—C13	108.45 (19)	C24—C26B—H26D	109.5
O4—C12—C8	108.7 (2)	C24—C26B—H26E	109.5
C13—C12—C8	110.82 (18)	H26D—C26B—H26E	109.5
O4—C12—H12A	109.6	C24—C26B—H26F	109.5
C13—C12—H12A	109.6	H26D—C26B—H26F	109.5
C8—C12—H12A	109.6	H26E—C26B—H26F	109.5
N3—C13—C12	111.04 (18)	C24—C27B—H27D	109.5
N3—C13—H13A	109.4	C24—C27B—H27E	109.5
C12—C13—H13A	109.4	H27D—C27B—H27E	109.5
N3—C13—H13B	109.4	C24—C27B—H27F	109.5
C12—C13—H13B	109.4	H27D—C27B—H27F	109.5
H13A—C13—H13B	108.0	H27E—C27B—H27F	109.5
C7B—O3—C7—O3B	154 (6)	O3B—C7B—C6—C5	−89 (3)
C7B—O3—C7—N2	−77 (3)	N2—C7B—C6—C5	125 (2)
C7B—O3—C7—C6	76 (3)	O3—C7B—C6—C7	87 (5)
O3—C7—O3B—C7B	−26 (5)	O3B—C7B—C6—C7	67 (4)
N2—C7—O3B—C7B	−88 (4)	N2—C7B—C6—C7	−80 (4)
C6—C7—O3B—C7B	88 (3)	C7—N2—C8—C12	−100.6 (15)
C7—O3—C7B—O3B	−25 (5)	C7B—N2—C8—C12	−85 (2)
C7—O3—C7B—N2	83 (4)	C11—N2—C8—C12	86.4 (4)
C7—O3—C7B—C6	−84 (4)	C11B—N2—C8—C12	96.6 (9)
C7—O3B—C7B—O3	153 (6)	C7—N2—C8—C9	139.3 (15)
C7—O3B—C7B—N2	68 (4)	C7B—N2—C8—C9	155 (2)
C7—O3B—C7B—C6	−76 (3)	C11—N2—C8—C9	−33.6 (4)
O3B—C7—N2—C7B	95 (4)	C11B—N2—C8—C9	−23.5 (9)
O3—C7—N2—C7B	72 (4)	N2—C8—C9—C10	14.1 (5)
C6—C7—N2—C7B	−81 (4)	C12—C8—C9—C10	−105.3 (4)
O3B—C7—N2—C8	−174 (2)	N2—C8—C9—C10B	29.1 (7)
O3—C7—N2—C8	163.8 (14)	C12—C8—C9—C10B	−90.3 (7)
C6—C7—N2—C8	11 (3)	C8—C9—C10—C11	10.2 (8)
O3—C7—N2—C11	−25 (3)	C7—N2—C11—C10	−131.3 (15)
C6—C7—N2—C11	−177.9 (10)	C8—N2—C11—C10	42.0 (7)
O3B—C7—N2—C11B	−10 (4)	C9—C10—C11—N2	−31.3 (9)
O3—C7—N2—C11B	−32 (3)	C8—C9—C10B—C11B	−31.8 (15)
C6—C7—N2—C11B	174.6 (15)	C7—N2—C11B—C10B	−161.4 (15)
O3—C7B—N2—C7	−87 (5)	C7B—N2—C11B—C10B	−174 (2)
O3B—C7B—N2—C7	−61 (4)	C8—N2—C11B—C10B	4.3 (16)
C6—C7B—N2—C7	80 (4)	C9—C10B—C11B—N2	18.3 (18)
O3—C7B—N2—C8	174.9 (19)	N2—C8—C12—O4	55.0 (2)
O3B—C7B—N2—C8	−159.1 (18)	C9—C8—C12—O4	168.76 (19)
C6—C7B—N2—C8	−18 (4)	N2—C8—C12—C13	174.05 (19)
O3—C7B—N2—C11B	−7 (4)	C9—C8—C12—C13	−72.1 (2)
O3B—C7B—N2—C11B	19 (4)	C22—N3—C13—C12	−85.1 (2)
C6—C7B—N2—C11B	161 (2)	C14—N3—C13—C12	152.70 (18)
C6—C1—C2—C3	3.5 (3)	O4—C12—C13—N3	−73.4 (2)
Cl1—C1—C2—C3	−174.92 (18)	C8—C12—C13—N3	167.38 (18)
C1—C2—C3—C4	0.3 (4)	C22—N3—C14—C23	177.20 (18)
C1—C2—C3—N1	−179.6 (2)	C13—N3—C14—C23	−61.1 (2)
O1B—N1—C3—C4	155 (6)	C22—N3—C14—C15	58.6 (2)
O1—N1—C3—C4	−168.9 (3)	C13—N3—C14—C15	−179.68 (18)
O2B—N1—C3—C4	−36 (7)	N3—C14—C15—C16	−56.0 (2)
O2—N1—C3—C4	10.2 (4)	C23—C14—C15—C16	−177.86 (18)
O1B—N1—C3—C2	−26 (6)	C14—C15—C16—C17	176.37 (19)
O1—N1—C3—C2	10.9 (4)	C14—C15—C16—C21	52.0 (2)
O2B—N1—C3—C2	144 (7)	C15—C16—C17—C18	−70.8 (3)
O2—N1—C3—C2	−169.9 (3)	C21—C16—C17—C18	52.9 (3)
C2—C3—C4—C5	−2.2 (4)	C16—C17—C18—C19	−55.0 (3)
N1—C3—C4—C5	177.7 (2)	C17—C18—C19—C20	55.7 (3)
C3—C4—C5—C6	0.4 (4)	C18—C19—C20—C21	−55.3 (3)
C2—C1—C6—C5	−5.2 (4)	C15—C16—C21—C22	−51.3 (2)
Cl1—C1—C6—C5	173.2 (2)	C17—C16—C21—C22	−176.4 (2)
C2—C1—C6—C7	−179.1 (6)	C15—C16—C21—C20	73.6 (2)
Cl1—C1—C6—C7	−0.7 (6)	C17—C16—C21—C20	−51.5 (3)
C2—C1—C6—C7B	176.1 (9)	C19—C20—C21—C22	177.21 (19)
Cl1—C1—C6—C7B	−5.5 (10)	C19—C20—C21—C16	53.1 (3)
C4—C5—C6—C1	3.2 (4)	C14—N3—C22—C21	−61.1 (2)
C4—C5—C6—C7	177.0 (7)	C13—N3—C22—C21	175.09 (19)
C4—C5—C6—C7B	−177.9 (8)	C16—C21—C22—N3	57.2 (2)
O3B—C7—C6—C1	105 (2)	C20—C21—C22—N3	−67.9 (2)
O3—C7—C6—C1	129 (2)	C24—N4—C23—O5	−3.2 (4)
N2—C7—C6—C1	−79 (2)	C24—N4—C23—C14	−178.2 (2)
O3B—C7—C6—C5	−69 (3)	N3—C14—C23—O5	149.4 (2)
O3—C7—C6—C5	−44 (3)	C15—C14—C23—O5	−89.9 (2)
N2—C7—C6—C5	107.5 (16)	N3—C14—C23—N4	−35.4 (3)
O3B—C7—C6—C7B	−95 (4)	C15—C14—C23—N4	85.3 (2)
O3—C7—C6—C7B	−71 (4)	C23—N4—C24—C25	−179.4 (4)
N2—C7—C6—C7B	81 (4)	C23—N4—C24—C27B	43.0 (15)
O3—C7B—C6—C1	110 (3)	C23—N4—C24—C27	60.9 (4)
O3B—C7B—C6—C1	90 (2)	C23—N4—C24—C26	−59.3 (5)
N2—C7B—C6—C1	−57 (3)	C23—N4—C24—C25B	162.1 (12)
O3—C7B—C6—C5	−69 (3)	C23—N4—C24—C26B	−83.0 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4C···O4	0.88 (3)	2.60 (3)	3.219 (3)	129 (3)
O4—H4B···O5^i	0.82 (1)	1.89 (2)	2.709 (2)	170 (4)

Symmetry code: (i) x−1, y, z.