Bringing a Molecular Plus One: Synergistic Binding Creates Guest-Mediated Three Component Complexes.
Taimoory, S. Maryamdokht; Twum, Kwaku; Dashti, Mohadeseh; Pan, FangFang; Lahtinen, Manu; Rissanen, Kari; Puttreddy, Rakesh; Trant, John F.; Beyeh, Ngong Kodiah; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00220

data_4038154
_publ_section_title
;
 Bringing a Molecular Plus One: Synergistic Binding Creates Guest-Mediated
 Three Component Complexes.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00220
_journal_year                    2020
_chemical_formula_moiety         'C40 H48 O8, C2 H3 O2, 2(C H4 O), C5 H6 N'
_chemical_formula_sum            'C300.75 H72 N O13.75'
_chemical_formula_weight         3918.59
_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   mixed
_audit_creation_date             2020-02-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                79.200(7)
_cell_angle_beta                 80.931(6)
_cell_angle_gamma                81.646(7)
_cell_formula_units_Z            4
_cell_length_a                   12.3935(9)
_cell_length_b                   12.7003(10)
_cell_length_c                   31.989(2)
_cell_measurement_reflns_used    4343
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      24.0980
_cell_measurement_theta_min      2.0690
_cell_volume                     4849.2(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120.00(10)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0804
_diffrn_reflns_av_unetI/netI     0.1782
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            29767
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_min         1.869
_exptl_absorpt_coefficient_mu    0.327
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    5.368
_exptl_crystal_description       block
_exptl_crystal_F_000             7974
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1190
_refine_ls_number_reflns         17485
_refine_ls_number_restraints     52
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.1969
_refine_ls_R_factor_gt           0.1213
_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^)+(0.1113P)^2^+16.6673P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2857
_refine_ls_wR_factor_ref         0.3380
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9215
_reflns_number_total             17485
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00220_si_002.cif
_cod_data_source_block           a_b_c5_sq
_cod_original_cell_volume        4849.1(7)
_cod_database_code               4038154
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.965
_olex2_refinement_description
;
1. 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
2. Restrained distances
 O25-C99 = O24-C98
 1.45 with sigma of 0.02
 O22-C96 = O23-C97
 1.45 with sigma of 0.02
 H3-O25
 1.9 with sigma of 0.04
 H24A-O7_$1
 2 with sigma of 0.04
 H98C-H3
 2.2 with sigma of 0.04
 H3-H17B
 2.2 with sigma of 0.04
 H4-H18
 2.2 with sigma of 0.04
 H23-O0AA
 1.9 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C97) \\sim Ueq, Uanis(O23) \\sim Ueq, Uanis(O24) \\sim Ueq: with sigma of
0.05 and sigma for terminal atoms of 0.01
Uanis(O22) \\sim Ueq, Uanis(C96) \\sim Ueq, Uanis(C98) \\sim Ueq, Uanis(C99)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C98) = Uanis(C99)
Uanis(C97) = Uanis(C96)
4. Others
 Fixed Sof: O23(0.7) H23(0.7) C97(0.7) H97A(0.7) H97B(0.7) H97C(0.7) O25(0.7)
 H25(0.7) C99(0.7) H99A(0.7) H99B(0.7) H99C(0.7) O24(0.3) H24A(0.3) C98(0.3)
 H98A(0.3) H98B(0.3) H98C(0.3) C96(0.3) H96A(0.3) H96B(0.3) H96C(0.3) O22(0.3)
 H22(0.3)
5.a Riding coordinates:
 O12(H12), O0AA(H0AA), O24(H24A), C98(H98A,H98B,H98C), O22(H22)
5.b Ternary CH refined with riding coordinates:
 C48(H48), C78(H78), C68(H68), C38(H38), C58(H58), C18(H18), C28(H28), C8(H8A)
5.c Secondary CH2 refined with riding coordinates:
 C39(H39A,H39B), C59(H59A,H59B), C69(H69A,H69B), C79(H79A,H79B), C9(H9A,H9B),
 C49(H49A,H49B), C29(H29A,H29B), C19(H19A,H19B)
5.d Aromatic/amide H refined with riding coordinates:
 C34(H34), C74(H74), C4(H4A), C64(H64), C44(H44), C14(H14A), C54(H54),
 C24(H24), C85(H85), C87(H87), C86(H86), C84(H84), C81(H81), C83(H83), C82(H82),
  C88(H88), C90(H90), C89(H89)
5.e Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C77(H77A,H77B,H77C), C37(H37A,H37B,H37C), C57(H57A,H57B,
 H57C), C7(H7A,H7B,H7C), C67(H67A,H67B,H67C), C40(H40A,H40B,H40C), C17(H17A,
 H17B,H17C), C47(H47A,H47B,H47C), C70(H70A,H70B,H70C), C60(H60A,H60B,H60C),
 C30(H30A,H30B,H30C), C50(H50A,H50B,H50C), C10(H10A,H10B,H10C), C80(H80A,H80B,
 H80C), C92(H92A,H92B,H92C), C94(H94A,H94B,H94C), C20(H20A,H20B,H20C),
 C03D(H03A,H03B,H03C), C95(H95A,H95B,H95C), C97(H97A,H97B,H97C), C99(H99A,H99B,
 H99C), C96(H96A,H96B,H96C)
5.f Idealised tetrahedral OH refined as rotating group:
 O15(H15), O2(H2), O13(H13), O14(H14), O11(H11), O8(H8), O4(H4), O7(H7),
 O10(H10), O3(H3), O16(H16), O6(H6), O1(H1), O9(H9), O5(H5), O21(H21), O23(H23),
  O25(H25)
;
_shelx_res_checksum              66776
_shelx_hkl_checksum              12046
_shelx_fab_checksum              17348
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'