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_4033324
_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         'C30 H44 O12, C12 H14 N2, C7 H7 O3 S, F6 P'
_chemical_formula_sum            'C49 H65 F6 N2 O15 P S'
_chemical_formula_weight         1099.06
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-10-02
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7404(5)
_cell_length_b                   18.6914(10)
_cell_length_c                   26.8438(14)
_cell_measurement_reflns_used    8702
_cell_measurement_temperature    218(2)
_cell_measurement_theta_max      24.08
_cell_measurement_theta_min      2.19
_cell_volume                     5389.0(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      218.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0887
_diffrn_reflns_av_unetI/netI     0.1231
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            41006
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        28.000
_diffrn_reflns_theta_max         28.307
_diffrn_reflns_theta_min         1.517
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             2312
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.707
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.5(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     673
_refine_ls_number_reflns         13042
_refine_ls_number_restraints     579
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.1818
_refine_ls_R_factor_gt           0.1379
_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^)+(0.0916P)^2^+16.1552P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2740
_refine_ls_wR_factor_ref         0.2986
_reflns_Friedel_coverage         0.819
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                8505
_reflns_number_total             13042
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02812_si_003.cif
_cod_data_source_block           gib27
_cod_depositor_comments
'Adding full bibliography for 4033323--4033325.cif.'
_cod_database_code               4033324
_shelx_shelxl_version_number     2017/1
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5(3)
 0.5(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Uiso/Uaniso restraints and constraints
N1 \\sim C31 \\sim C32 \\sim C33 \\sim C34 \\sim C35 \\sim C36: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C22(H22A,H22B),
  C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,
 H27B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7A), C17(H17), C19(H19), C21(H21), C31(H31), C32(H32),
 C34(H34), C35(H35), C37(H37), C38(H38), C40(H40), C41(H41), C43(H43), C44(H44),
  C46(H46), C47(H47)
5.c Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C42(H42A,H42B,H42C), C49(H49A,H49B,H49C)
5.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O7(H7)
;
_shelx_res_checksum              73269
_shelx_hkl_checksum              38013
_shelx_fab_checksum              81949
_olex2_submission_original_sample_id gib27
_olex2_submission_special_instructions 'No special instructions were received'