Dispersion and Halogen-Bonding Interactions: Binding of the Axial Conformers of Monohalo- and (±)-trans-1,2-Dihalocyclohexanes in Enantiopure Alleno-Acetylenic Cages.
Gropp, Cornelius; Husch, Tamara; Trapp, Nils; Reiher, Markus; Diederich, François; Journal of the American Chemical Society 139 (2017) 12190–12200; doi:10.1021/jacs.7b05461

data_4131444
_publ_section_title
;
 Dispersion and Halogen-Bonding Interactions: Binding of the Axial
 Conformers of Monohalo- and (+-)-trans-1,2-Dihalocyclohexanes in
 Enantiopure Alleno-Acetylenic Cages.
;
_journal_issue                   35
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12190
_journal_page_last               12200
_journal_paper_doi               10.1021/jacs.7b05461
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         '0.38(C6 H10 Br1 F1), C128 H168 O12'
_chemical_formula_sum            'C130.29 H171.82 Br0.38 F0.38 O12'
_chemical_formula_weight         1967.83
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.6223(2)
_cell_length_b                   18.7222(3)
_cell_length_c                   43.2981(7)
_cell_measurement_reflns_used    57631
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      77.1070
_cell_measurement_theta_min      3.1200
_cell_volume                     12664.0(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (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 1.000
_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    -70.00  17.00   0.50    0.60    --   -5.51 -77.00-120.00  174
  2  \w     -5.00  80.00   0.50    0.60    --    5.51  38.00   0.00  170
  3  \w     85.00 173.00   0.50    2.00    --  107.75  77.00   0.00  176
  4  \w     98.00 178.00   0.50    2.00    --  107.75  38.00   0.00  160
  5  \w     85.00 173.00   0.50    2.00    --  107.75  77.00 120.00  176
  6  \w     93.00 178.00   0.50    2.00    --  107.75  57.00 120.00  170
  7  \w     85.00 173.00   0.50    2.00    --  107.75  77.00  90.00  176
  8  \w     93.00 178.00   0.50    2.00    --  107.75  57.00 -60.00  170
  9  \w     85.00 173.00   0.50    2.00    --  107.75  77.00 -30.00  176
 10  \w     93.00 178.00   0.50    2.00    --  107.75  57.00-150.00  170
 11  \w     85.00 173.00   0.50    2.00    --  107.75  77.00 -60.00  176
 12  \w     85.00 173.00   0.50    2.00    --  107.75  77.00-180.00  176
 13  \w     85.00 173.00   0.50    2.00    --  107.75  77.00-150.00  176
 14  \w     85.00 173.00   0.50    2.00    --  107.75  77.00-120.00  176
 15  \w     85.00 173.00   0.50    2.00    --  107.75  77.00 -90.00  176
 16  \w     85.00 173.00   0.50    2.00    --  107.75  77.00  30.00  176
 17  \w     85.00 173.00   0.50    2.00    --  107.75  77.00 150.00  176
 18  \w     85.00 173.00   0.50    2.00    --  107.75  77.00  60.00  176
 19  \w     39.00 111.00   0.50    2.00    --  107.75 -99.00 -60.00  144
 20  \w     43.00 130.00   0.50    2.00    --  107.75 -77.00  30.00  174
 21  \w     39.00 111.00   0.50    2.00    --  107.75 -99.00  90.00  144
 22  \w     39.00 111.00   0.50    2.00    --  107.75 -99.00  30.00  144
 23  \w     38.00 121.00   0.50    2.00    --  107.75-125.00-120.00  166
 24  \w     39.00 111.00   0.50    2.00    --  107.75 -99.00-180.00  144
 25  \w     43.00 130.00   0.50    2.00    --  107.75 -77.00-120.00  174
 26  \w     37.00  84.00   0.50    2.00    --  107.75 -57.00  90.00   94
 27  \w    -70.00  17.00   0.50    0.60    --   -5.51 -77.00  30.00  174
 28  \w    -70.00  17.00   0.50    0.60    --    5.51 -19.00  90.00  174
 29  \w    -92.00  -5.00   0.50    2.00    --  -70.00  77.00 -90.00  174
 30  \w    -95.00  -9.00   0.50    2.00    --  -70.00 125.00 -30.00  172
 31  \w   -141.00 -55.00   0.50    2.00    --  -70.00 -57.00  90.00  172
 32  \w   -135.00 -47.00   0.50    2.00    --  -70.00 -77.00  90.00  176
 33  \w   -135.00 -47.00   0.50    2.00    --  -70.00 -77.00 150.00  176
 34  \w   -135.00 -47.00   0.50    2.00    --  -70.00 -77.00   0.00  176
 35  \w   -135.00 -47.00   0.50    2.00    --  -70.00 -77.00-180.00  176
 36  \w   -135.00 -47.00   0.50    2.00    --  -70.00 -77.00-150.00  176
 37  \w   -135.00 -47.00   0.50    2.00    --  -70.00 -77.00 -90.00  176
 38  \w   -135.00 -47.00   0.50    2.00    --  -70.00 -77.00  60.00  176
 39  \w   -135.00 -47.00   0.50    2.00    --  -70.00 -77.00 -30.00  176
 40  \w   -135.00 -47.00   0.50    2.00    --  -70.00 -77.00 120.00  176
 41  \w   -135.00 -47.00   0.50    2.00    --  -70.00 -77.00  30.00  176
 42  \w   -141.00 -55.00   0.50    2.00    --  -70.00 -57.00  60.00  172
 43  \w   -135.00 -47.00   0.50    2.00    --  -70.00 -77.00 -60.00  176
 44  \w   -141.00 -55.00   0.50    2.00    --  -70.00 -57.00 -90.00  172
 45  \w   -135.00 -47.00   0.50    2.00    --  -70.00 -77.00-120.00  176
;
_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      0.0024408000
_diffrn_orient_matrix_UB_12      -0.0026864000
_diffrn_orient_matrix_UB_13      -0.0355429000
_diffrn_orient_matrix_UB_21      -0.0980756000
_diffrn_orient_matrix_UB_22      0.0082770000
_diffrn_orient_matrix_UB_23      -0.0010295000
_diffrn_orient_matrix_UB_31      0.0100242000
_diffrn_orient_matrix_UB_32      0.0818381000
_diffrn_orient_matrix_UB_33      -0.0010495000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            59459
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.076
_diffrn_reflns_theta_min         3.007
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.637
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.18b (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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       plate
_exptl_crystal_F_000             4266
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.037
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 6379 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1435
_refine_ls_number_reflns         59459
_refine_ls_number_restraints     322
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1199
_refine_ls_R_factor_gt           0.0771
_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^)+(0.1240P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1918
_refine_ls_wR_factor_ref         0.2152
_reflns_Friedel_coverage         0.845
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                37646
_reflns_number_total             59459
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b05461_si_004.cif
_cod_data_source_block           d160815_41_6_twin1_hklf4
_cod_database_code               4131444
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C134H178BrFO12
_diffrn_oxdiff_ac3_digest_frames
;
0120342503160bd3401845037a44184cce076326bee
;
_diffrn_oxdiff_ac3_digest_hkl
;
01e8042d0b0be54c9ef3a8195f097e4aa3797a
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6893(13)
 0.3107(13)
2. 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
3. Restrained distances
 C14A-C13A = C14-C13 = C15-C14 = C15-C14A = C16-C15 = C17-C16
 1.5 with sigma of 0.02
 C6-C38 \\sim C6-C5 \\sim C6-C5A \\sim C5-C4 \\sim C5A-C4A \\sim C4-C3 \\sim
C4A-C3A \\sim C3-C2 \\sim C3A-C2
 \\sim C2-C1
 with sigma of 0.02
 C1-C3 \\sim C1-C3A \\sim C2-C4 \\sim C2-C4A \\sim C3-C5 \\sim C3A-C5A \\sim
C4-C6 \\sim C4A-C6
 with sigma of 0.02
 C17-C16 \\sim C16-C15 \\sim C15-C14A \\sim C15-C14 \\sim C14A-C13A \\sim
C14-C13
 with sigma of 0.02
 C13A-C15 \\sim C13-C15 \\sim C14A-C16 \\sim C14-C16 \\sim C15-C17
 with sigma of 0.02
 C11-C10 \\sim C9-C10 \\sim C9-C8 \\sim C9-C8A \\sim C8A-C7A \\sim C8-C7
 with sigma of 0.02
 C7-C9 \\sim C7A-C9 \\sim C8-C10 \\sim C8A-C10 \\sim C9-C11
 with sigma of 0.02
4. Rigid bond restraints
 C6, C2, C5, C1, C3, C4, C5A, C4A, C3A, C6, C5, C6, C5A, C5, C4, C5A, C4A, C4,
 C3, C4A, C3A, C3, C2, C3A, C2, C2, C1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C17, C16, C15, C14A, C13A, C14, C13, C17, C16, C16, C15, C15, C14A, C15, C14,
 C14A, C13A, C14, C13
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
Uanis(C7A) = Uanis(C7)
6. Rigid body (RIGU) restrains
 C6, C2, C5, C1, C3, C4, C5A, C4A, C3A, C6, C5, C6, C5A, C5, C4, C5A, C4A, C4,
 C3, C4A, C3A, C3, C2, C3A, C2, C2, C1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C17, C16, C15, C14A, C13A, C14, C13, C17, C16, C16, C15, C15, C14A, C15, C14,
 C14A, C13A, C14, C13
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C9, C10, C8, C7, C8A, C7A, C9, C10, C9, C8, C9, C8A, C8, C7, C8A, C7A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F1B, Br1B, C1B, C6B, C2B, C3B, C4B, C5B, Br1B, C1B, Br1B, C6B, C1B, C2B, C6B,
 C1B, C2B, C3B, F1B, C2B, C3B, C4B, C5B, C4B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
7. Others
 Sof(H6BC)=Sof(H6BD)=Sof(H9BC)=Sof(H9BD)=Sof(H2BC)=Sof(H2BD)=Sof(H15C)=
 Sof(H15D)=Sof(C14A)=Sof(H14A)=Sof(H14B)=Sof(C13A)=Sof(H13A)=Sof(H13B)=
 Sof(H13C)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(C3A)=
 Sof(H3AA)=Sof(H3AB)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(C7A)=Sof(H7AA)=Sof(H7AB)=
 Sof(H7AC)=1-FVAR(1)
 Sof(H6AA)=Sof(H6AB)=Sof(H9AA)=Sof(H9AB)=Sof(H2AA)=Sof(H2AB)=Sof(C5)=Sof(H5A)=
 Sof(H5B)=Sof(H15A)=Sof(H15B)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(C3)=Sof(H3A)=
 Sof(H3B)=Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(H7C)=Sof(C14)=
 Sof(H14C)=Sof(H14D)=Sof(C13)=Sof(H13D)=Sof(H13E)=Sof(H13F)=FVAR(1)
 Sof(Br1B)=Sof(C3B)=Sof(H3BA)=Sof(H3BB)=Sof(C2B)=Sof(H2B)=Sof(C1B)=Sof(H1BA)=
 Sof(C6B)=Sof(H6BA)=Sof(H6BB)=Sof(C5B)=Sof(H5BA)=Sof(H5BB)=Sof(F1B)=Sof(C4B)=
 Sof(H4BA)=Sof(H4BB)=FVAR(2)
8.a Ternary CH refined with riding coordinates:
 C38(H38), C56(H56), C57(H57), C64(H64), C2B(H2B), C1B(H1BA)
8.b Secondary CH2 refined with riding coordinates:
 C41(H41A,H41B), C46(H46A,H46B), C68(H68A,H68B), C18(H18A,H18B), C12(H12A,
 H12B), C17(H17A,H17B), C24(H24A,H24B), C91(H91A,H91B), C11(H11A,H11B),
 C23(H23A,H23B), C6(H6AA,H6AB), C6(H6BC,H6BD), C16(H16A,H16B), C20(H20A,H20B),
 C9(H9AA,H9AB), C9(H9BC,H9BD), C10(H10P,H10Q), C22(H22A,H22B), C2(H2AA,H2AB),
 C2(H2BC,H2BD), C21(H21A,H21B), C5(H5A,H5B), C15(H15C,H15D), C15(H15A,H15B),
 C8(H8A,H8B), C3(H3A,H3B), C4(H4A,H4B), C14A(H14A,H14B), C3B(H3BA,H3BB),
 C6B(H6BA,H6BB), C5B(H5BA,H5BB), C4B(H4BA,H4BB), C5A(H5AA,H5AB), C4A(H4AA,H4AB),
  C3A(H3AA,H3AB), C14(H14C,H14D), C8A(H8AA,H8AB)
8.c Aromatic/amide H refined with riding coordinates:
 C27(H27), C36(H36), C52(H52), C69(H69)
8.d Idealised Me refined as rotating group:
 C84(H84A,H84B,H84C), C90(H90A,H90B,H90C), C93(H93A,H93B,H93C), C94(H94A,H94B,
 H94C), C95(H95A,H95B,H95C), C96(H96A,H96B,H96C), C97(H97A,H97B,H97C), C98(H98A,
 H98B,H98C), C99(H99A,H99B,H99C), C100(H10A,H10B,H10C), C102(H10D,H10E,H10F),
 C104(H10G,H10H,H10I), C105(H10J,H10K,H10L), C108(H10M,H10N,H10O), C110(H11C,
 H11D,H11E), C111(H11F,H11G,H11H), C112(H11I,H11J,H11K), C114(H11L,H11M,H11N),
 C115(H11O,H11P,H11Q), C116(H11R,H11S,H11T), C117(H11U,H11V,H11W), C118(H11X,
 H11Y,H), C119(H11Z,HA,HB), C120(H12C,H12D,H12E), C121(H12F,H12G,H12H),
 C122(H12I,H12J,H12K), C123(H12L,H12M,H12N), C124(H12O,H12P,H12Q), C125(H12R,
 H12S,H12T), C19(H19A,H19B,H19C), C1(H1A,H1B,H1C), C126(H12U,H12V,H12W),
 C127(H12X,H12Y,HC), C128(H12Z,HD,HE), C7(H7A,H7B,H7C), C13A(H13A,H13B,H13C),
 C13(H13D,H13E,H13F), C7A(H7AA,H7AB,H7AC)
8.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O2(H2), O4(H4), O1(H1)
;
_shelx_res_checksum              93407
_shelx_hkl_checksum              85202
_olex2_date_sample_data_collection 2017-03-08
_olex2_date_sample_submission    2017-03-01
_olex2_submission_original_sample_id d160815_41_6
_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 2.473
_oxdiff_exptl_absorpt_empirical_full_min 0.507
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
_twin_special_details
;
Component 2 rotated by -179.9952\% 
 around [0.00 0.00 1.00] (reciprocal) or [0.03 0.00 1.00] (direct)
;