Molecular Recognition of Hydrophilic Molecules in Water by Combining the Hydrophobic Effect with Hydrogen Bonding.
Yao, Huan; Ke, Hua; Zhang, Xiaobin; Pan, San-Jiang; Li, Ming-Shuang; Yang, Liu-Pan; Schreckenbach, Georg; Jiang, Wei; Journal of the American Chemical Society 140 (2018) 13466–13477; doi:10.1021/jacs.8b09157

data_4133258
_publ_section_title
;
 Molecular Recognition of Hydrophilic Molecules in Water by Combining the
 Hydrophobic Effect with Hydrogen Bonding.
;
_journal_issue                   41
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13466
_journal_page_last               13477
_journal_paper_doi               10.1021/jacs.8b09157
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C66 H66 N2 O10, C4 H9 N O'
_chemical_formula_sum            'C70 H75 N3 O11'
_chemical_formula_weight         1134.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-02-01
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90.8850(10)
_cell_angle_beta                 92.499(2)
_cell_angle_gamma                103.131(2)
_cell_formula_units_Z            1
_cell_length_a                   11.8762(5)
_cell_length_b                   12.1010(5)
_cell_length_c                   12.2447(5)
_cell_measurement_reflns_used    1523
_cell_measurement_temperature    160.0
_cell_measurement_theta_max      59.13
_cell_measurement_theta_min      3.5
_cell_volume                     1711.51(12)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      160.0
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14197
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        57.896
_diffrn_reflns_theta_max         57.896
_diffrn_reflns_theta_min         3.614
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.596
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1020 before and 0.0482 after correction. The Ratio of minimum to maximum transmission is 0.8248. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.101
_exptl_crystal_description       block
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.849
_refine_diff_density_min         -1.341
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.507
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         4690
_refine_ls_number_restraints     314
_refine_ls_restrained_S_all      1.706
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0818
_refine_ls_shift/su_max          0.003
_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          0.3078
_refine_ls_wR_factor_ref         0.3200
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4147
_reflns_number_total             4690
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b09157_si_011.cif
_cod_data_source_block           n-ethylacetamide@3b
_cod_database_code               4133258
_shelx_shelxl_version_number     2014/7
_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. Restrained distances
 C37-C38
 1.53 with sigma of 0.02
 C38-C37
 1.53 with sigma of 0.02
 C36-O7
 1.19 with sigma of 0.02
 C37-N2
 1.47 with sigma of 0.02
 C35-C36
 1.53 with sigma of 0.02
 C36-C35
 1.53 with sigma of 0.02
 O7-C36
 1.19 with sigma of 0.02
 C38-N2
 2.5 with sigma of 0.04
 C37-C36
 2.5 with sigma of 0.04
 C36-C37
 2.5 with sigma of 0.04
 N2-C35
 2.5 with sigma of 0.04
 O7-C35
 2.5 with sigma of 0.04
 C35-N2
 2.5 with sigma of 0.04
 C35-O7
 3 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
Uanis(O6) = Uanis(O5)
Uanis(C38) = Uanis(C37)
Uanis(C37) = Uanis(C36)
Uanis(C35) = Uanis(C36)
Uanis(N2) = Uanis(N1)
4. Others
 Fixed Sof: O5(0.5) O6(0.5) H6A(0.5) H6B(0.5) H5A(0.5) H5B(0.5) O7(0.5)
 N2(0.5) H2(0.5) C35(0.5) H35A(0.5) H35B(0.5) H35C(0.5) C36(0.5) C37(0.5)
 H37A(0.5) H37B(0.5) C38(0.5) H38A(0.5) H38B(0.5) H38C(0.5)
5.a Ternary CH refined with riding coordinates:
 C1(H1A), C3(H3)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C28(H28A,H28B),
 C29(H29A,H29B), C30(H30A,H30B), C33(H6A,H6B), C34(H5A,H5B), C37(H37A,H37B)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C8(H8), C9(H9), C10(H10), C11(H11), C20(H20), C21(H21), C24(H24),
 C25(H25), N2(H2)
5.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C31(H31A,H31B,H31C), C35(H35A,H35B,H35C), C38(H38A,H38B,
 H38C)
;
_olex2_submission_special_instructions 'No special instructions were received'