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_4038156
_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, C5 H6 N, C6 H9 O2'
_chemical_formula_sum            'C51 H63 N O10'
_chemical_formula_weight         850.02
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   50.063(2)
_cell_length_b                   16.2050(8)
_cell_length_c                   16.6954(6)
_cell_measurement_reflns_used    15817
_cell_measurement_temperature    133(19)
_cell_measurement_theta_max      76.4620
_cell_measurement_theta_min      3.7690
_cell_volume                     13544.5(10)
_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      133(19)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.965
_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  -2.00   1.00   10.00    --  -38.38 125.00 -30.00   94
  2  \w    -35.00  70.00   1.00   10.00    --   38.38 -37.00 150.00  105
  3  \w     32.00  98.00   1.00   10.00    --   38.38-125.00-150.00   66
  4  \w     83.00 178.00   1.00   40.00    --  116.00  61.00 -30.00   95
  5  \w     43.00 149.00   1.00   40.00    --  116.00 -61.00-120.00  106
  6  \w    100.00 171.00   1.00   40.00    --  116.00  79.00  14.00   71
  7  \w     83.00 163.00   1.00   40.00    --  116.00  30.00 -60.00   80
  8  \w    107.00 174.00   1.00   40.00    --  116.00 111.00-120.00   67
;
_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      -0.0534762000
_diffrn_orient_matrix_UB_12      -0.0241640000
_diffrn_orient_matrix_UB_13      0.0208129000
_diffrn_orient_matrix_UB_21      0.0582168000
_diffrn_orient_matrix_UB_22      -0.0184711000
_diffrn_orient_matrix_UB_23      -0.0467093000
_diffrn_orient_matrix_UB_31      0.0479718000
_diffrn_orient_matrix_UB_32      -0.0044285000
_diffrn_orient_matrix_UB_33      0.0800882000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       63
_diffrn_reflns_limit_h_min       -55
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            43729
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.183
_diffrn_reflns_theta_min         2.866
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.695
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88271
_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    1.251
_exptl_crystal_description       block
_exptl_crystal_F_000             5472
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     934
_refine_ls_number_reflns         14013
_refine_ls_number_restraints     67
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.0996
_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^)+(0.0203P)^2^+63.5685P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2118
_refine_ls_wR_factor_ref         0.2222
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11561
_reflns_number_total             14013
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00220_si_002.cif
_cod_data_source_block           ABC9
_cod_original_cell_volume        13544.6(10)
_cod_database_code               4038156
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C30 H30 N1 O9'
_reflns_odcompleteness_completeness 99.46
_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 C(H,H,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
 C81-C80_$1
 1.52 with sigma of 0.02
 C74B-C73 \\sim C74-C73 \\sim C74B-C75 \\sim C74-C75
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C66) \\sim Ueq, Uanis(C67) \\sim Ueq, Uanis(C69) \\sim Ueq, Uanis(C70)
\\sim Ueq, Uanis(C77) \\sim Ueq, Uanis(C79) \\sim Ueq, Uanis(C81) \\sim Ueq,
Uanis(C82) \\sim Ueq, Uanis(O16) \\sim Ueq, Uanis(N2) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: C66(0.5) H66(0.5) C67(0.5) H67(0.5) C68(0.5) H68(0.5) C69(0.5)
 H69(0.5) C70(0.5) H70(0.5) N2(0.5) H2A(0.5) H73A(0.5) H73B(0.5) H73C(0.5)
 H73D(0.5) C74(0.5) H74A(0.5) H74B(0.5) C74B(0.5) H74C(0.5) H74D(0.5) H75A(0.5)
 H75B(0.5) H75C(0.5) H75D(0.5) C77(0.5) C78(0.5) H78(0.5) C79(0.5) H79A(0.5)
 H79B(0.5) C80(0.5) H80A(0.5) H80B(0.5) C81(0.5) H81A(0.5) H81B(0.5) C82(0.5)
 H82A(0.5) H82B(0.5) O15(0.5) O16(0.5)
5.a Riding coordinates:
 N1(H1A)
5.b Ternary CH refined with riding coordinates:
 C8(H8), C18(H18), C28(H28), C38(H38), C48(H48), C58(H58), C72(H72), C78(H78)
5.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C19(H19A,H19B), C29(H29A,H29B), C39(H39A,H39B), C49(H49A,H49B),
 C59(H59A,H59B), C73(H73A,H73B), C73(H73C,H73D), C74(H74A,H74B), C74B(H74C,
 H74D), C75(H75A,H75B), C75(H75C,H75D), C76(H76A,H76B), C79(H79A,H79B),
 C80(H80A,H80B), C81(H81A,H81B), C82(H82A,H82B)
5.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C14(H14), C24(H24), C34(H34), C44(H44), C54(H54), C61(H61), C62(H62),
 C63(H63), C64(H64), C65(H65), C66(H66), C67(H67), C68(H68), C69(H69), C70(H70),
  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), C47(H47A,H47B,H47C), C50(H50A,H50B,H50C), C57(H57A,H57B,H57C),
 C60(H60A,H60B,H60C)
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), O9(H9),
 O10(H10), O11(H11), 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 1.149
_oxdiff_exptl_absorpt_empirical_full_min 0.832