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_4038153
_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
'2(C40 H48 O8), 2(C3 H3.5 N0.5), 2(C1.6 F2.4 O1.6), 3.4(C H4 O), O'
_chemical_formula_sum            'C92.6 H116.6 F4.8 N O23.6'
_chemical_formula_weight         1712.46
_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             2019-07-06
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                64.281(9)
_cell_angle_beta                 77.984(6)
_cell_angle_gamma                77.832(7)
_cell_formula_units_Z            1
_cell_length_a                   12.4816(8)
_cell_length_b                   13.6012(15)
_cell_length_c                   14.6525(12)
_cell_measurement_reflns_used    5405
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.1970
_cell_measurement_theta_min      3.3440
_cell_volume                     2171.4(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_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 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -96.00 -10.00   2.00    6.00    --  -41.78 125.00 150.00   43
  2  \w   -115.00 -25.00   2.00    6.00    --  -41.78 -37.00  90.00   45
  3  \w   -109.00 -17.00   2.00    6.00    --  -41.78 -37.00   0.00   46
  4  \w      1.00  83.00   2.00    6.00    --   41.78 -99.00 -30.00   41
  5  \w     32.00 150.00   2.00   30.00    --  112.00 -15.00   0.00   59
  6  \w     32.00 108.00   2.00   30.00    --  112.00 -94.00-150.00   38
  7  \w     36.00 144.00   2.00   30.00    --  112.00 -77.00  30.00   54
  8  \w     50.00  78.00   2.00   30.00    --  112.00-111.00 120.00   14
  9  \w     83.00 167.00   2.00   30.00    --  112.00  61.00-180.00   42
 10  \w     69.00 151.00   2.00   30.00    --  112.00 178.00  90.00   41
 11  \w     90.00 116.00   2.00   30.00    --  112.00-111.00 120.00   13
 12  \w     46.00 136.00   2.00   30.00    --  112.00 -45.00-150.00   45
 13  \w    102.00 140.00   2.00   30.00    --  112.00 -30.00 150.00   19
 14  \w     45.00  93.00   2.00   30.00    --  112.00 -30.00 150.00   24
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0461631000
_diffrn_orient_matrix_UB_12      0.1167449000
_diffrn_orient_matrix_UB_13      -0.0061415000
_diffrn_orient_matrix_UB_21      0.0470532000
_diffrn_orient_matrix_UB_22      -0.0279019000
_diffrn_orient_matrix_UB_23      0.0989313000
_diffrn_orient_matrix_UB_31      0.1090065000
_diffrn_orient_matrix_UB_32      0.0412154000
_diffrn_orient_matrix_UB_33      -0.0635408000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13733
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        66.750
_diffrn_reflns_theta_max         76.852
_diffrn_reflns_theta_min         3.378
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.835
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97394
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       plate
_exptl_crystal_F_000             911
_exptl_crystal_size_max          0.181
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.041
_refine_diff_density_max         0.930
_refine_diff_density_min         -0.784
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     670
_refine_ls_number_reflns         8693
_refine_ls_number_restraints     63
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0730
_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^)+(0.1350P)^2^+1.9050P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2094
_refine_ls_wR_factor_ref         0.2282
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6949
_reflns_number_total             8693
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00220_si_002.cif
_cod_data_source_block           ABC1
_cod_original_formula_sum        'C92.60 H116.60 F4.80 N O23.60'
_cod_database_code               4038153
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C30 H30 N1 O9 F3'
_reflns_odcompleteness_completeness 98.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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, All O(H) groups
2. Restrained distances
 O9C-C47C
 1.45 with sigma of 0.02
 O12-C48
 1.45 with sigma of 0.02
 O11-C49
 1.45 with sigma of 0.02
 H2-O12_$1
 1.7 with sigma of 0.02
 F3-C47B \\sim F2-C47B \\sim F1B-C47B \\sim F3-C47 \\sim F2-C47 \\sim F1-C47
 with sigma of 0.01
 C47B-C46 \\sim C47-C46
 with sigma of 0.01
 O9B-C46 \\sim O10B-C46
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(N2) \\sim Ueq, Uanis(C47B) \\sim Ueq, Uanis(F1B) \\sim Ueq, Uanis(O12)
\\sim Ueq, Uanis(C48) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C47C) \\sim Ueq, Uanis(O9C) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
4. Others
 Fixed Sof: C41(0.5) H41(0.5) C42(0.5) H42(0.5) C44(0.5) H44(0.5) C45(0.5)
 H45(0.5) N2(0.5) H2A(0.5) C46(0.8) C47(0.5) C47B(0.3) F1(0.5) F1B(0.3) F2(0.8)
 F3(0.8) O9(0.5) O9B(0.3) O10(0.5) O10B(0.3) C47C(0.2) H47A(0.2) H47B(0.2)
 H47C(0.2) C48(0.5) H48A(0.5) H48B(0.5) H48C(0.5) O9C(0.2) H9C(0.2) O12(0.5)
 H12(0.5) O13(0.5)
5.a Riding coordinates:
 O12(H12)
5.b Ternary CH refined with riding coordinates:
 C8(H8), C18(H18), C28(H28), C38(H38)
5.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C19(H19A,H19B), C29(H29A,H29B), C39(H39A,H39B)
5.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C14(H14), C24(H24), C34(H34), C41(H41), C42(H42), C43(H43), C44(H44),
 C45(H45), N2(H2A)
5.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C10(H10A,H10B,H10C), C17(H17A,H17B,H17C), C20(H20A,H20B,
 H20C), C27(H27A,H27B,H27C), C30(H30A,H30B,H30C), C37(H37A,H37B,H37C), C40(H40A,
 H40B,H40C), C47C(H47A,H47B,H47C), C48(H48A,H48B,H48C), C49(H49A,H49B,H49C)
5.f Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3), O4(H4A), O5(H5), O6(H6), O7(H7), O8(H8A), O9C(H9C),
 O11(H11)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.178
_oxdiff_exptl_absorpt_empirical_full_min 0.843