N-tert-Butyl Sulfinyl Squaramide Receptors for Anion Recognition through Assisted tert-Butyl C-H Hydrogen Bonding.
Li, Yao; Yang, Guo-Hui; Shen, Ye-Ye; Xue, Xiao-Song; Li, Xin; Cheng, Jin-Pei; The Journal of organic chemistry 82 (2017) 8662–8667; doi:10.1021/acs.joc.7b01634

data_4032720
_publ_section_title
;
 N-tert-Butyl Sulfinyl Squaramide Receptors for Anion Recognition through
 Assisted tert-Butyl C-H Hydrogen Bonding.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8662
_journal_page_last               8667
_journal_paper_doi               10.1021/acs.joc.7b01634
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'Cl, C12 H20 N2 O4 S2, C16 H36 N'
_chemical_formula_sum            'C28 H56 Cl N3 O4 S2'
_chemical_formula_weight         598.32
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-08-11
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.320(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.353(2)
_cell_length_b                   17.154(3)
_cell_length_c                   16.604(3)
_cell_measurement_reflns_used    10155
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4777
_cell_measurement_theta_min      1.7278
_cell_volume                     3437.4(10)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution
;
'SHELXS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0289
_diffrn_orient_matrix_UB_12      0.0480
_diffrn_orient_matrix_UB_13      -0.0610
_diffrn_orient_matrix_UB_21      0.0377
_diffrn_orient_matrix_UB_22      0.0245
_diffrn_orient_matrix_UB_23      0.0371
_diffrn_orient_matrix_UB_31      0.0454
_diffrn_orient_matrix_UB_32      -0.0344
_diffrn_orient_matrix_UB_33      -0.0234
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            37589
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.460
_diffrn_reflns_theta_min         1.255
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.13
_refine_diff_density_max         1.129
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 5760 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     705
_refine_ls_number_reflns         15492
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0591
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0557P)^2^+1.5629P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
_refine_ls_wR_factor_ref         0.1375
_reflns_Friedel_coverage         0.917
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                14577
_reflns_number_total             15492
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01634_si_002.cif
_cod_data_source_block           sa3542
_cod_original_cell_volume        3437.5(10)
_cod_database_code               4032720
_shelxl_version_number           2013-4
_diffrn_number_total             8116
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13A(H13A,H13B), C14A(H14A,H14B), C15A(H15A,H15B), C17A(H17A,H17B), C18A(H18A,
 H18B), C19A(H19A,H19B), C21A(H21A,H21B), C22A(H22A,H22B), C23A(H23A,H23B),
 C25A(H25A,H25B), C26A(H26A,H26B), C27A(H27A,H27B), C13(H13C,H13D), C14(H14C,
 H14D), C15(H15C,H15D), C17(H17C,H17D), C18(H18C,H18D), C19(H19C,H19D),
 C21(H21C,H21D), C22(H22C,H22D), C23(H23C,H23D), C25(H25C,H25D), C26(H26C,H26D),
  C27(H27C,H27D)
2.b Aromatic/amide H refined with riding coordinates:
 N1A(H1A), N2A(H2A), N1(H1), N2(H2)
2.c Idealised Me refined as rotating group:
 C6A(H6AA,H6AB,H6AC), C7A(H7AA,H7AB,H7AC), C8A(H8AA,H8AB,H8AC), C10A(H10A,H10B,
 H10C), C11A(H11A,H11B,H11C), C12A(H12A,H12B,H12C), C6(H6A,H6B,H6C), C7(H7A,H7B,
 H7C), C8(H8A,H8B,H8C), C10(H10D,H10E,H10F), C11(H11D,H11E,H11F), C12(H12D,H12E,
 H12F), C16A(H16A,H16B,H16C), C20A(H20A,H20B,H20C), C24A(H24A,H24B,H24C),
 C28A(H28A,H28B,H28C), C16(H16D,H16E,H16F), C20(H20D,H20E,H20F), C24(H24D,H24E,
 H24F), C28(H28D,H28E,H28F)
;
_shelx_res_checksum              17449
_shelx_hkl_checksum              52538