Molecular Recognition and Cocrystallization of Methylated and Halogenated Fragments of Danicalipin A by Enantiopure Alleno-Acetylenic Cage Receptors.
Gropp, Cornelius; Fischer, Stefan; Husch, Tamara; Trapp, Nils; Carreira, Erick M.; Diederich, François; Journal of the American Chemical Society 142 (2020) 4749–4755; doi:10.1021/jacs.9b13217

data_4134295
_publ_section_title
;
 Molecular Recognition and Cocrystallization of Methylated and Halogenated
 Fragments of Danicalipin A by Enantiopure Alleno-Acetylenic Cage
 Receptors.
;
_journal_issue                   10
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4749
_journal_page_last               4755
_journal_paper_doi               10.1021/jacs.9b13217
_journal_volume                  142
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C128 H168 O12, C6 H14 O'
_chemical_formula_sum            'C134 H182 O13'
_chemical_formula_weight         2000.79
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.41030(10)
_cell_length_b                   18.60230(10)
_cell_length_c                   44.9029(2)
_cell_measurement_reflns_used    180597
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      79.4710
_cell_measurement_theta_min      3.4360
_cell_volume                     12872.18(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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   -116.00 -78.00   0.50    1.00    --  -49.37 -77.00  30.00   76
  2  \w   -116.00 -78.00   0.50    1.00    --  -49.37 -77.00   0.00   76
  3  \w   -116.00 -78.00   0.50    1.00    --  -49.37 -77.00  90.00   76
  4  \w   -140.00 -84.00   0.50    4.50    --  -70.00 -99.00   0.00  112
  5  \w   -141.00 -75.00   0.50    4.50    --  -70.00-125.00  90.00  132
  6  \w   -142.00 -54.00   0.50    4.50    --  -70.00 -57.00 120.00  176
  7  \w    -63.00  26.00   0.50    1.00    --  -49.37  38.00 120.00  178
  8  \w    -63.00  26.00   0.50    1.00    --  -49.37  38.00 150.00  178
  9  \w     78.00 116.00   0.50    1.00    --   49.37  77.00 -60.00   76
 10  \w     97.00 178.00   0.50    4.50    --  110.00 116.00 -31.00  162
 11  \w     98.00 178.00   0.50    4.50    --  110.00  38.00-150.00  160
 12  \w     94.00 178.00   0.50    4.50    --  110.00  57.00  30.00  168
 13  \w     94.00 178.00   0.50    4.50    --  110.00  57.00  60.00  168
 14  \w     91.00 178.00   0.50    4.50    --  110.00 125.00 150.00  174
 15  \w     94.00 178.00   0.50    4.50    --  110.00  57.00  90.00  168
 16  \w     86.00 177.00   0.50    4.50    --  110.00  77.00   0.00  182
 17  \w     94.00 123.00   0.50    4.50    --  110.00 -19.00-150.00   58
 18  \w     94.00 123.00   0.50    4.50    --  110.00 -19.00-180.00   58
 19  \w     86.00 177.00   0.50    4.50    --  110.00  77.00-180.00  182
 20  \w     94.00 123.00   0.50    4.50    --  110.00 -19.00  30.00   58
 21  \w     40.00 110.00   0.50    4.50    --  110.00 -99.00 -90.00  140
 22  \w     40.00 110.00   0.50    4.50    --  110.00 -99.00-180.00  140
 23  \w     44.00 134.00   0.50    4.50    --  110.00 -77.00-150.00  180
 24  \w     39.00 122.00   0.50    4.50    --  110.00-125.00  30.00  166
 25  \w     44.00 134.00   0.50    4.50    --  110.00 -77.00  60.00  180
 26  \w     39.00 120.00   0.50    4.50    --  110.00-122.00 152.00  162
 27  \w     38.00  84.00   0.50    4.50    --  110.00 -57.00 120.00   92
 28  \w     40.00 110.00   0.50    4.50    --  110.00 -99.00  60.00  140
 29  \w     38.00  84.00   0.50    4.50    --  110.00 -57.00 -90.00   92
 30  \w     38.00  84.00   0.50    4.50    --  110.00 -57.00-120.00   92
 31  \w     34.00 121.00   0.50    1.00    --   49.37  57.00  30.00  174
 32  \w     38.00  84.00   0.50    4.50    --  110.00 -57.00  60.00   92
 33  \w     38.00  84.00   0.50    4.50    --  110.00 -57.00  90.00   92
 34  \w     34.00 121.00   0.50    1.00    --   49.37  57.00 150.00  174
 35  \w     34.00 121.00   0.50    1.00    --   49.37  57.00 -60.00  174
 36  \w     34.00 121.00   0.50    1.00    --   49.37  57.00-150.00  174
 37  \w    -22.00 121.00   0.50    1.00    --   49.37   0.00-120.00  286
 38  \w    -73.00  17.00   0.50    1.00    --  -49.37  77.00-120.00  180
 39  \w    -95.00  -9.00   0.50    4.50    --  -70.00 125.00 -30.00  172
 40  \w   -116.00 -78.00   0.50    1.00    --  -49.37 -77.00-120.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0064485000
_diffrn_orient_matrix_UB_12      -0.0200327000
_diffrn_orient_matrix_UB_13      -0.0332169000
_diffrn_orient_matrix_UB_21      -0.0173839000
_diffrn_orient_matrix_UB_22      0.0793508000
_diffrn_orient_matrix_UB_23      -0.0078157000
_diffrn_orient_matrix_UB_31      0.0982253000
_diffrn_orient_matrix_UB_32      0.0127017000
_diffrn_orient_matrix_UB_33      -0.0035505000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       57
_diffrn_reflns_limit_l_min       -56
_diffrn_reflns_number            264846
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.213
_diffrn_reflns_theta_min         3.032
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.501
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.709
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.032
_exptl_crystal_description       block
_exptl_crystal_F_000             4360
_exptl_crystal_size_max          0.173
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.106
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 11779 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1389
_refine_ls_number_reflns         27814
_refine_ls_number_restraints     105
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0578P)^2^+2.2083P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1011
_reflns_Friedel_coverage         0.842
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                26671
_reflns_number_total             27814
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            CCDC-1914838.cif
_cod_data_source_block           d160815_12_3
_cod_depositor_comments
'Adding full bibliography for 4134283--4134298.cif.'
_cod_database_code               4134295
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C134H182O13
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O1-H1 = O2-H2 = O4-H4 = O3-H3 = O1C-H1CA
 0.93 with sigma of 0.02
 C18-C17 \\sim C17-C16 \\sim C16-C15 \\sim C16-C15A \\sim C15A-C14A \\sim
C15-C14 \\sim C14-C13 \\sim C14A-
 C13A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C15) = Uanis(C15A)
Uanis(C14) = Uanis(C14A)
Uanis(C13) = Uanis(C13A)
4. Rigid body (RIGU) restrains
 C24, C23, C22, C21, C20, C19
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C18, C17, C15, C16, C14, C13, C15A, C14A, C13A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H16C)=Sof(H16D)=Sof(C15A)=Sof(H15C)=Sof(H15D)=Sof(C14A)=Sof(H14C)=
 Sof(H14D)=Sof(C13A)=Sof(H13D)=Sof(H13E)=Sof(H13F)=1-FVAR(1)
 Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H16A)=Sof(H16B)=Sof(C14)=Sof(H14A)=Sof(H14B)=
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C34(H34), C39(H39), C46(H46), C72(H72)
6.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C24(H24A,H24B), C56(H56A,H56B), C57(H57A,H57B), C62(H62A,H62B),
 C65(H65A,H65B), C12(H12A,H12B), C18(H18A,H18B), C5(H5A,H5B), C3(H3A,H3B),
 C4(H4A,H4B), C11(H11A,H11B), C23(H23A,H23B), C3C(H3CA,H3CB), C10(H10A,H10B),
 C2(H2A,H2B), C17(H17A,H17B), C1C(H1CB,H1CC), C9(H9A,H9B), C22(H22A,H22B),
 C15(H15A,H15B), C16(H16A,H16B), C16(H16C,H16D), C21(H21A,H21B), C8(H8A,H8B),
 C14(H14A,H14B), C20(H20A,H20B), C15A(H15C,H15D), C14A(H14C,H14D)
6.c Aromatic/amide H refined with riding coordinates:
 C26(H26), C35(H35), C37(H37), C45(H45)
6.d Idealised Me refined as rotating group:
 C95(H95A,H95B,H95C), C97(H97A,H97B,H97C), C98(H98A,H98B,H98C), C99(H99A,H99B,
 H99C), C100(H10C,H10D,H10E), C101(H10F,H10G,H10H), C4C(H4CA,H4CB,H4CC),
 C103(H10I,H10J,H10K), C104(H10L,H10M,H10N), C105(H10O,H10P,H10Q), C106(H10R,
 H10S,H10T), C107(H10U,H10V,H10W), C108(H10X,H10Y,H), C109(H10Z,HA,HB),
 C110(H11C,H11D,H11E), C111(H11F,H11G,H11H), C112(H11I,H11J,H11K), C113(H11L,
 H11M,H11N), C114(H11O,H11P,H11Q), C5C(H5CA,H5CB,H5CC), C115(H11R,H11S,H11T),
 C116(H11U,H11V,H11W), C117(H11X,H11Y,HC), C118(H11Z,HD,HE), C6C(H6CA,H6CB,
 H6CC), C119(H11,HF,HG), C120(H12C,H12D,H12E), C121(H12F,H12G,H12H), C1(H1A,H1B,
 H1C), C122(H12I,H12J,H12K), C123(H12L,H12M,H12N), C124(H12O,H12P,H12Q),
 C125(H12R,H12S,H12T), C7(H7A,H7B,H7C), C126(H12U,H12V,H12W), C127(H12X,H12Y,
 HH), C128(H12Z,HI,HJ), C13(H13A,H13B,H13C), C19(H19A,H19B,H19C), C13A(H13D,
 H13E,H13F)
;
_shelx_res_checksum              69916
_shelx_hkl_checksum              3963
_olex2_date_sample_data_collection 2018-01-15
_olex2_date_sample_submission    2018-01-15
_olex2_submission_original_sample_id d160815_12_3
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.776
_oxdiff_exptl_absorpt_empirical_full_min 0.840