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_4038155
_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(C4 H5 O2), C4 H6 O2, H2 O, 2(C5 H6 N)'
_chemical_formula_sum            'C102 H126 N2 O23'
_chemical_formula_weight         1748.04
_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                77.760(9)
_cell_angle_beta                 75.988(9)
_cell_angle_gamma                73.191(9)
_cell_formula_units_Z            1
_cell_length_a                   12.5897(13)
_cell_length_b                   12.7023(13)
_cell_length_c                   15.9641(15)
_cell_measurement_reflns_used    4901
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      73.0710
_cell_measurement_theta_min      2.8620
_cell_volume                     2343.3(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 2014/5 (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 0.988
_diffrn_measured_fraction_theta_max 0.952
_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    -64.00  26.00   2.00   15.00    --  -41.90  37.00 120.00   45
  2  \w    -74.00  22.00   2.00   15.00    --  -41.90  77.00-150.00   48
  3  \w   -112.00 -18.00   2.00   15.00    --  -41.90 -37.00 -60.00   47
  4  \w     36.00 108.00   2.00   60.00    --  105.08 -45.00-120.00   36
  5  \w     87.00 177.00   2.00   60.00    --  105.08  30.00 150.00   45
  6  \w     34.00 108.00   2.00   60.00    --  105.08 -94.00 -90.00   37
  7  \w     35.00 137.00   2.00   60.00    --  105.08 -77.00   0.00   51
  8  \w     80.00 172.00   2.00   60.00    --  105.08  45.00  90.00   46
  9  \w     34.00 120.00   2.00   60.00    --  105.08-125.00-150.00   43
 10  \w     87.00 175.00   2.00   60.00    --  105.08  61.00  30.00   44
 11  \w     98.00 172.00   2.00   60.00    --  105.08 125.00 -30.00   37
;
_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      0.0508156000
_diffrn_orient_matrix_UB_12      0.0118097000
_diffrn_orient_matrix_UB_13      -0.0985125000
_diffrn_orient_matrix_UB_21      0.0953211000
_diffrn_orient_matrix_UB_22      -0.1053470000
_diffrn_orient_matrix_UB_23      0.0163025000
_diffrn_orient_matrix_UB_31      -0.0728420000
_diffrn_orient_matrix_UB_32      -0.0720993000
_diffrn_orient_matrix_UB_33      -0.0125979000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14376
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.520
_diffrn_reflns_theta_min         2.887
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96198
_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    1.239
_exptl_crystal_description       plate
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.142
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     624
_refine_ls_number_reflns         8986
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0494
_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^)+(0.0601P)^2^+0.8957P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1353
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7061
_reflns_number_total             8986
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00220_si_002.cif
_cod_data_source_block           ABC7
_cod_database_code               4038155
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C22 H11 O2'
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.906
_reflns_odcompleteness_completeness 99.02
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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, All O(H,H) groups
2. Restrained distances
 O12-C44 = O11-C44
 1.2 with sigma of 0.02
 H12-O10_$1
 1.7 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(O11) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
4. Others
 Fixed Sof: O11(0.5) O12(0.5) H12(0.5) O13(0.5) H13A(0.5) H13B(0.5) C41(0.5)
 H41A(0.5) H41B(0.5) C42(0.5) H42A(0.5) H42B(0.5) C43(0.5) H43(0.5) C44(0.5)
5.a Riding coordinates:
 N1(H1A)
5.b Free rotating group:
 O13(H13A,H13B)
5.c Ternary CH refined with riding coordinates:
 C7(H7A), C14(H14), C21(H21), C28(H28), C43(H43), C47(H47)
5.d Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C31(H31A,H31B), C33(H33A,H33B), C35(H35A,H35B), C41(H41A,
 H41B), C42(H42A,H42B), C45(H45A,H45B), C46(H46A,H46B)
5.e Aromatic/amide H refined with riding coordinates:
 C4(H4A), C9(H9), C16(H16), C27(H27), C49(H49), C50(H50), C51(H51), C52(H52),
 C53(H53)
5.f Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C32(H32A,H32B,H32C), C34(H34A,H34B,H34C), C36(H36A,H36B,
 H36C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C40(H40A,
 H40B,H40C)
5.g Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3), O4(H4), O5(H5), O6(H6), O7(H7), O8(H8), O12(H12)
;
_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 1.073
_oxdiff_exptl_absorpt_empirical_full_min 0.922