High-Yielding Syntheses of Crown Ether-Based Pyridyl Cryptands.
Price, Jr, Terry L; Wessels, Hanlie R.; Slebodnick, Carla; Gibson, Harry W.; The Journal of organic chemistry 82 (2017) 8117–8122; doi:10.1021/acs.joc.7b01389

data_4032748
_publ_section_title
;
 High-Yielding Syntheses of Crown Ether-Based Pyridyl Cryptands.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8117
_journal_page_last               8122
_journal_paper_doi               10.1021/acs.joc.7b01389
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety
'C37 H45 N O14, C2 F6 N O4 S2, C5 H6 N, C H Cl3, H2 O'
_chemical_formula_sum            'C45 H54 Cl3 F6 N3 O19 S2'
_chemical_formula_weight         1225.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-25
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                93.0710(11)
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_cell_length_a                   10.85860(17)
_cell_length_b                   22.1145(4)
_cell_length_c                   22.6189(3)
_cell_measurement_reflns_used    33592
_cell_measurement_temperature    100.1(4)
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_cell_measurement_theta_min      2.8850
_cell_volume                     5412.59(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_diffrn_ambient_environment      N~2~
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_diffrn_detector                 'CCD plate'
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;
  1 omega -115.00  -15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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  2 omega  -69.00   31.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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  3 omega -126.00  -79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.9419  -99.0000  150.0000 47

  4 omega    2.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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  5 omega   73.00  119.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.9419  125.0000  120.0000 46

  6 omega   27.00  114.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000  150.0000 87

  7 omega   22.00  109.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -94.0000  150.0000 87

  8 omega   33.00   77.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -45.0000   60.0000 44

  9 omega   27.00  101.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000  -90.0000 74

 10 omega   77.00  178.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   64.0000   72.6704 101

 11 omega   59.00  178.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   15.0000   60.0000 119

 12 omega   27.00  106.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000 -120.0000 79

 13 omega   30.00   69.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000  -30.0000 39

 14 omega   22.00  109.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -94.0000  -30.0000 87

 15 omega   28.00  141.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -77.0000  -30.0000 113

 16 omega   22.00  100.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -94.0000  -90.0000 78

 17 omega   59.00  178.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   15.0000 -150.0000 119

 18 omega   33.00  136.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -61.0000  -30.0000 103

 19 omega   33.00  136.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -61.0000    0.0000 103

 20 omega   27.00  115.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -111.0000   90.0000 88

 21 omega   22.00  109.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -94.0000  -60.0000 87

 22 omega   33.00  136.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -61.0000  120.0000 103

 23 omega   33.00   77.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -45.0000  120.0000 44

 24 omega   31.00  125.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000 -131.0000   92.6282 94

 25 omega   78.00  178.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   61.0000  -30.0000 100

 26 omega   30.00   69.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000  -30.0000 -150.0000 39

 27 omega   77.00  178.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      107.0000   30.0000  120.0000 101

 28 omega -115.00  -15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.9419  -57.0000  -90.0000 100

 29 omega -115.00  -26.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.9419  -57.0000  150.0000 89

 30 omega    5.00   34.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.9419   87.0000 -114.7187 29
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_radiation_monochromator  mirror
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_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0409
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_diffrn_reflns_limit_l_max       28
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_diffrn_reflns_number            88419
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_diffrn_source                   'sealed X-ray tube'
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_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
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Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
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_exptl_crystal_recrystallization_method 'Crystallized from CDCl3 (in NMR tube)'
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_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.001
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_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0749P)^2^+3.3026P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_cod_data_source_file            jo7b01389_si_002.cif
_cod_data_source_block           cs2173
_cod_original_cell_volume        5412.60(14)
_cod_database_code               4032748
_chemical_oxdiff_formula         'C45 H54 Cl3 F6 N3 O19 S2'
_chemical_oxdiff_usercomment     'Daniel Schoonover/Gibson (TP30CryPyrTFSI02)'
_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 O(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C89(H89), C90(H90)
2.b Secondary CH2 refined with riding coordinates:
 C50(H50A,H50B), C51(H51A,H51B), C52(H52A,H52B), C53(H53A,H53B), C54(H54A,
 H54B), C55(H55A,H55B), C56(H56A,H56B), C57(H57A,H57B), C58(H58A,H58B),
 C59(H59A,H59B), C60(H60A,H60B), C61(H61A,H61B), C62(H62A,H62B), C63(H63A,H63B),
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 H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B),
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B),
  C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,
 H27B), C28(H28A,H28B), C29(H29A,H29B), C37(H37A,H37B)
2.c Aromatic/amide H refined with riding coordinates:
 C40(H40), C42(H42), C43(H43), C46(H46), C48(H48), C49(H49), C69(H69),
 C70(H70), C71(H71), C3(H3), C5(H5), C6(H6), C9(H9), C11(H11), C12(H12),
 C32(H32), C33(H33), C34(H34), N3(H3A), C75(H75), C76(H76), C77(H77), C78(H78),
 C79(H79), N4(H4), C80(H80), C81(H81), C82(H82), C83(H83), C84(H84)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-03-19
_olex2_date_sample_submission    2015-03-16
_olex2_submission_original_sample_id cs2173
_olex2_submission_special_instructions 'No special instructions were received'