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_4133255
_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 H6 O2'
_chemical_formula_sum            'C70 H72 N2 O12'
_chemical_formula_weight         1133.29
_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             2017-03-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_cell_angle_alpha                93.443(2)
_cell_angle_beta                 91.068(2)
_cell_angle_gamma                105.257(2)
_cell_formula_units_Z            1
_cell_length_a                   11.8324(5)
_cell_length_b                   11.8564(4)
_cell_length_c                   12.4505(5)
_cell_measurement_reflns_used    4826
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      62.32
_cell_measurement_theta_min      3.61
_cell_volume                     1681.00(11)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      150.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.0309
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_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            12525
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        59.056
_diffrn_reflns_theta_max         59.056
_diffrn_reflns_theta_min         3.559
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.6617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1015 before and 0.0462 after correction.
The Ratio of minimum to maximum transmission is 0.8804.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_description       block
_exptl_crystal_F_000             602
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         4762
_refine_ls_number_restraints     46
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0527
_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^)+(0.0669P)^2^+0.5647P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1418
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3408
_reflns_number_total             4762
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b09157_si_002.cif
_cod_data_source_block           p-1_a
_cod_database_code               4133255
_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
 C36-C37
 1.42 with sigma of 0.02
 O6-C34 = O7-C35
 1.4 with sigma of 0.02
 C34-C35
 1.42 with sigma of 0.02
 O6-C34 = O7-C35 = O6-C36 = O7-C37
 1.54 with sigma of 0.02
 O6-C37
 2.45 with sigma of 0.04
 C36-O7
 2.45 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
O6 \\sim C34 \\sim O7 \\sim C35 \\sim C36 \\sim C37: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: H14A(0.5) H14B(0.5) H29A(0.5) H29B(0.5) O3A(0.5) O3B(0.5) C34(0.5)
 H34(0.5) C35(0.5) H35(0.5) C36(0.5) H36A(0.5) H36B(0.5) C37(0.5) H37A(0.5)
 H37B(0.5) O6(0.5) O7(0.5)
5.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B),
 C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C36(H36A,H36B),
  C37(H37A,H37B)
5.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C10(H10), C11(H11), C22(H22), C23(H23), C27(H27), C28(H28),
 N1(H1A), C34(H34), C35(H35)
5.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C33(H33A,H33B,H33C)
;
_olex2_submission_special_instructions 'No special instructions were received'