Pseudocryptand Hosts for Paraquats and Diquats.
Jones, Jason W.; Price, Jr, Terry L; Huang, Feihe; Zakharov, Lev; Rheingold, Arnold L.; Slebodnick, Carla; Gibson, Harry W.; The Journal of organic chemistry 83 (2018) 823–834; doi:10.1021/acs.joc.7b02812

data_4033323
_publ_section_title
;
 Pseudocryptand Hosts for Paraquats and Diquats.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              823
_journal_page_last               834
_journal_paper_doi               10.1021/acs.joc.7b02812
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety
'C42 H50 N2 O14, C12 H12 N2, 2(F6 P), 2(C3 H6 O)'
_chemical_formula_sum            'C60 H74 F12 N4 O16 P2'
_chemical_formula_weight         1397.17
_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   geom
_audit_creation_date             2015-11-11
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                100.240(2)
_cell_angle_beta                 110.402(3)
_cell_angle_gamma                92.464(3)
_cell_formula_units_Z            2
_cell_length_a                   13.4306(4)
_cell_length_b                   15.1390(5)
_cell_length_c                   17.0352(4)
_cell_measurement_reflns_used    11626
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.5870
_cell_measurement_theta_min      3.4770
_cell_volume                     3173.95(18)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 4.1587
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -118.00 -73.00   1.00    2.50    --  -41.94-125.00  90.00   45
  2  \w     12.00 117.00   1.00    2.50    --   41.94  37.00  60.00  105
  3  \w      2.00  98.00   1.00    2.50    --   41.94-125.00-180.00   96
  4  \w     15.00 115.00   1.00    2.50    --   41.94  57.00 -60.00  100
  5  \w     22.00 109.00   1.00   12.50    --  107.00 -94.00 -90.00   87
  6  \w     22.00 109.00   1.00   12.50    --  107.00 -94.00-120.00   87
  7  \w     33.00  77.00   1.00   12.50    --  107.00 -45.00 120.00   44
  8  \w     33.00 136.00   1.00   12.50    --  107.00 -61.00  90.00  103
  9  \w     59.00 178.00   1.00   12.50    --  107.00  15.00-150.00  119
 10  \w     27.00  86.00   1.00   12.50    --  107.00-111.00 120.00   59
 11  \w     59.00 178.00   1.00   12.50    --  107.00  15.00 150.00  119
 12  \w     27.00 115.00   1.00   12.50    --  107.00-111.00-150.00   88
 13  \w     27.00 106.00   1.00   12.50    --  107.00-111.00   0.00   79
 14  \w     27.00 115.00   1.00   12.50    --  107.00-111.00 -60.00   88
 15  \w     32.00  58.00   1.00   12.50    --  107.00 -30.00 -60.00   26
 16  \w     29.00  68.00   1.00   12.50    --  107.00 -94.00  60.00   39
 17  \w     71.00  84.00   1.00   12.50    --  107.00 -94.00  60.00   13
 18  \w     32.00  68.00   1.00   12.50    --  107.00 -30.00-120.00   36
 19  \w     28.00  92.00   1.00   12.50    --  107.00-111.00  60.00   64
 20  \w     72.00 135.00   1.00   12.50    --  107.00  15.00 -60.00   63
 21  \w     22.00  77.00   1.00   12.50    --  107.00 -94.00 -30.00   55
 22  \w     28.00  78.00   1.00   12.50    --  107.00 -77.00  60.00   50
 23  \w     79.00 136.00   1.00   12.50    --  107.00 179.00  90.00   57
 24  \w     39.00  74.00   1.00   12.50    --  107.00 -45.00  90.00   35
 25  \w     45.00  71.00   1.00   12.50    --  107.00 -94.00 -60.00   26
 26  \w     72.00  98.00   1.00   12.50    --  107.00 -94.00 -60.00   26
 27  \w     38.00  64.00   1.00   12.50    --  107.00 179.00  90.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1110299000
_diffrn_orient_matrix_UB_12      -0.0327514000
_diffrn_orient_matrix_UB_13      0.0349147000
_diffrn_orient_matrix_UB_21      0.0521776000
_diffrn_orient_matrix_UB_22      0.0986809000
_diffrn_orient_matrix_UB_23      0.0287394000
_diffrn_orient_matrix_UB_31      -0.0111304000
_diffrn_orient_matrix_UB_32      0.0047947000
_diffrn_orient_matrix_UB_33      0.0876163000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            36146
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         74.990
_diffrn_reflns_theta_min         2.986
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.559
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.651
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_description       plate
_exptl_crystal_F_000             1456
_exptl_crystal_recrystallization_method 'Crystallized from acetone/pentane'
_exptl_crystal_size_max          0.488
_exptl_crystal_size_mid          0.247
_exptl_crystal_size_min          0.022
_refine_diff_density_max         1.822
_refine_diff_density_min         -0.981
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.480
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1016
_refine_ls_number_reflns         12786
_refine_ls_number_restraints     261
_refine_ls_restrained_S_all      1.521
_refine_ls_R_factor_all          0.1377
_refine_ls_R_factor_gt           0.1165
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3404
_refine_ls_wR_factor_ref         0.3822
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9406
_reflns_number_total             12786
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02812_si_005.cif
_cod_data_source_block           cs2219
_cod_depositor_comments
'Adding full bibliography for 4033323--4033325.cif.'
_cod_original_cell_volume        3173.95(17)
_cod_database_code               4033323
_chemical_oxdiff_formula         'C60 H74 F12 N4 O16 P2'
_chemical_oxdiff_usercomment
'Terry Price/Gibson (S11P1 with DQ PF6, vial C)'
_reflns_odcompleteness_completeness 99.59
_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 C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 P1, F1, F2, F3, F4, F5, F6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 P2A, F8A, F9A, F10A, F11A, F12A, P2B, F8B, F9B, F10B, F11B, F12B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C15A, C16A, C15B, C16B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O7A, O8A, O9A, O7B, O8B, O9B, C21A, C22A, C23A, C24A, C25A, C26A, C27A, C21B,
 C22B, C23B, C24B, C25B, C26B, C27B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(P2B)=Sof(F8B)=Sof(F9B)=Sof(F10B)=Sof(F11B)=Sof(F12B)=1-FVAR(1)
 Sof(P2A)=Sof(F8A)=Sof(F9A)=Sof(F10A)=Sof(F11A)=Sof(F12A)=FVAR(1)
 Sof(C15B)=Sof(H15C)=Sof(H15D)=Sof(C16B)=Sof(H16C)=Sof(H16D)=1-FVAR(2)
 Sof(C15A)=Sof(H15A)=Sof(H15B)=Sof(C16A)=Sof(H16A)=Sof(H16B)=FVAR(2)
 Sof(O7B)=Sof(O8B)=Sof(O9B)=Sof(C21B)=Sof(H21C)=Sof(H21D)=Sof(C22B)=Sof(H22C)=
 Sof(H22D)=Sof(C23B)=Sof(H23C)=Sof(H23D)=Sof(C24B)=Sof(H24C)=Sof(H24D)=
 Sof(C25B)=Sof(H25C)=Sof(H25D)=Sof(C26B)=Sof(H26C)=Sof(H26D)=Sof(C27B)=
 Sof(H27C)=Sof(H27D)=Sof(H28C)=Sof(H28D)=1-FVAR(3)
 Sof(O7A)=Sof(O8A)=Sof(O9A)=Sof(C21A)=Sof(H21A)=Sof(H21B)=Sof(C22A)=Sof(H22A)=
 Sof(H22B)=Sof(C23A)=Sof(H23A)=Sof(H23B)=Sof(C24A)=Sof(H24A)=Sof(H24B)=
 Sof(C25A)=Sof(H25A)=Sof(H25B)=Sof(C26A)=Sof(H26A)=Sof(H26B)=Sof(C27A)=
 Sof(H27A)=Sof(H27B)=Sof(H28A)=Sof(H28B)=FVAR(3)
4.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15A(H15A,H15B), C16A(H16A,H16B), C15B(H15C,
 H15D), C16B(H16C,H16D), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B),
 C20(H20A,H20B), C21A(H21A,H21B), C22A(H22A,H22B), C23A(H23A,H23B), C24A(H24A,
 H24B), C25A(H25A,H25B), C26A(H26A,H26B), C27A(H27A,H27B), C21B(H21C,H21D),
 C22B(H22C,H22D), C23B(H23C,H23D), C24B(H24C,H24D), C25B(H25C,H25D), C26B(H26C,
 H26D), C27B(H27C,H27D), C28(H28A,H28B), C28(H28C,H28D), C29(H29A,H29B),
 C36(H36A,H36B), C53(H53A,H53B), C54(H54A,H54B)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C9(H9), C11(H11), C12(H12), C32(H32), C33(H33),
 C34(H34), C35(H35), C39(H39), C40(H40), C41(H41), C42(H42), C43(H43), C44(H44),
  C45(H45), C46(H46), C49(H49), C50(H50), C51(H51), C52(H52)
4.c Idealised Me refined as rotating group:
 C58(H58A,H58B,H58C), C60(H60A,H60B,H60C), C55(H55A,H55B,H55C), C57(H57A,H57B,
 H57C)
;
_shelx_res_checksum              67433
_shelx_hkl_checksum              20970
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-08-13
_olex2_date_sample_submission    2015-08-11
_olex2_exptl_crystal_mounting_method 'Mounted on nylon loop with Krytox'
_olex2_submission_original_sample_id 'S11P1 + DQPF6 (vial C)'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.232
_oxdiff_exptl_absorpt_empirical_full_min 0.463