Macrocycle Synthesis by Chloride-Templated Amide Bond Formation.
Martí-Centelles, Vicente; Burguete, M. Isabel; Luis, Santiago V.; The Journal of organic chemistry 81 (2016) 2143–2147; doi:10.1021/acs.joc.5b02676

data_4036545
_publ_section_title
;
 Macrocycle Synthesis by Chloride-Templated Amide Bond Formation.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2143
_journal_page_last               2147
_journal_paper_doi               10.1021/acs.joc.5b02676
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration syn
_chemical_formula_moiety         '2(C2 H6 O S), C20 H28 N4 O4'
_chemical_formula_sum            'C24 H40 N4 O6 S2'
_chemical_formula_weight         544.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
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_cell_length_b                   9.54113(15)
_cell_length_c                   16.1853(3)
_cell_measurement_reflns_used    15660
_cell_measurement_temperature    200.0
_cell_measurement_theta_max      72.8390
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_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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omega____ theta____ kappa____ phi______ frames
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omega____ theta____ kappa____ phi______ frames
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omega____ theta____ kappa____ phi______ frames
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  5 omega    1.00   82.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
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omega____ theta____ kappa____ phi______ frames
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  7 omega   79.00  178.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega   31.00  121.00   0.5000    1.0000
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  9 omega   79.00  178.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
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 10 omega   31.00   99.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1650  -45.0000   60.0000 136

 11 omega   94.00  178.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
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 12 omega   31.00  121.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1650 -125.0000  150.0000 180

 13 omega   31.00   99.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1650  -45.0000 -180.0000 136

 14 omega   76.00  178.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
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 15 omega   79.00  178.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1650   45.0000 -180.0000 198

 16 omega   94.00  178.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1650  125.0000  150.0000 168

 17 omega   94.00  178.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1650  125.0000  -60.0000 168

 18 omega   73.00  178.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1650   77.0000 -150.0000 210

 19 omega -119.00   -6.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680  -77.0000   30.0000 226

 20 omega  -50.00   36.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680   38.0000  -30.0000 172

 21 omega -114.00  -10.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680  -57.0000   90.0000 208

 22 omega -119.00   -6.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680  -77.0000  150.0000 226

 23 omega -119.00   -6.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680  -77.0000  -60.0000 226

 24 omega -114.00  -10.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680  -57.0000 -180.0000 208

 25 omega   79.00  178.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1650   45.0000   90.0000 198

 26 omega   73.00  178.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1650   77.0000 -120.0000 210

 27 omega   73.00  178.00   0.5000    1.0000
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 28 omega   73.00  178.00   0.5000    1.0000
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 29 omega   73.00  178.00   0.5000    1.0000
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 30 omega   73.00  178.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
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 31 omega   22.00  109.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
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 32 omega   73.00  118.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
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 33 omega   73.00  178.00   0.5000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1650   77.0000  120.0000 210
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_diffrn_radiation_monochromator  mirror
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_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
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_diffrn_source                   'sealed X-ray tube'
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
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Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_density_diffrn    1.226
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 Flack x determined using 2538 quotients [(I+)-(I-)]/[(I+)+(I-)]
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'w=1/[\s^2^(Fo^2^)+(0.0924P)^2^+0.1383P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1231
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_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                5619
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_cod_data_source_file            jo5b02676_si_002.cif
_cod_data_source_block           str1780
_cod_database_code               4036545
_chemical_oxdiff_formula         'C20 H28 N4 O4'
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H16A)=Sof(C18B)=Sof(H18B)=Sof(C20B)=Sof(H20A)=Sof(H20B)=Sof(H20C)=
 Sof(C19B)=Sof(H19A)=Sof(H19B)=Sof(H19C)=1-FVAR(1)
 Sof(H16)=Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19D)=Sof(H19E)=Sof(H19F)=
 Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=FVAR(1)
 Sof(C23A)=Sof(H23D)=Sof(H23E)=Sof(H23F)=1-FVAR(2)
 Sof(C23B)=Sof(H23A)=Sof(H23B)=Sof(H23C)=FVAR(2)
3.a Ternary CH refined with riding coordinates:
 C5(H5), C4(H4A), C16(H16), C16(H16A), C18A(H18A), C18B(H18B)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C1(H1A,H1B)
3.c Aromatic/amide H refined with riding coordinates:
 N4(H4), N3(H3), N1(H1), C14(H14), N2(H2), C12(H12), C10(H10), C11(H11)
3.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C21(H21A,H21B,H21C), C7(H7A,H7B,H7C), C20(H20G,H20H,H20I),
 C22(H22A,H22B,H22C), C23B(H23A,H23B,H23C), C20B(H20A,H20B,H20C), C19B(H19A,
 H19B,H19C), C19A(H19D,H19E,H19F), C20A(H20D,H20E,H20F), C23A(H23D,H23E,H23F)
;
_shelx_res_checksum              67891
_shelx_hkl_checksum              73317
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'