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_4131441
_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         'C128 H168 O12, C6 H11 Cl, C2 H3 N'
_chemical_formula_sum            'C136 H182 Cl N O12'
_chemical_formula_weight         2058.27
_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     direct
_audit_creation_date             2016-06-13
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.4726(2)
_cell_length_b                   18.2043(3)
_cell_length_c                   46.4340(7)
_cell_measurement_reflns_used    9880
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      66.69
_cell_measurement_theta_min      5.35
_cell_volume                     13079.0(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker Apex2 Duo (Cu)'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'double mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_number            69719
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        66.755
_diffrn_reflns_theta_max         66.755
_diffrn_reflns_theta_min         5.219
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0783 before and 0.0615 after correction.
The Ratio of minimum to maximum transmission is 0.8391.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.045
_exptl_crystal_description       plate
_exptl_crystal_F_000             4472
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 7467 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.015(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1448
_refine_ls_number_reflns         22747
_refine_ls_number_restraints     245
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0499
_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^)+(0.0594P)^2^+4.0449P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1276
_reflns_Friedel_coverage         0.825
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                19261
_reflns_number_total             22747
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b05461_si_008.cif
_cod_data_source_block           cu_d160815_25_1_0m
_cod_database_code               4131441
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.864
_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
 O2-H2 = O1-H1 = O4-H4 = O3-H3
 0.91 with sigma of 0.01
 C3A-C2A \\sim C3A-C2B \\sim C2A-C1A \\sim C2B-C1B
 with sigma of 0.02
 C9A-C10A \\sim C9B-C10A \\sim C9A-C8A \\sim C9B-C8B \\sim C8B-C7B \\sim C8A-C7A
 with sigma of 0.02
3. Rigid bond restraints
 C3A, C4A, C5A, C6A, C10A, C11A, C12A, C13A, C14A, C15A, C16A, C17A, C18A,
 C19A, C20A, C21A, C22A, C23A, C24A, C1A, C2A, C7A, C8A, C9A, C1B, C2B, C7B,
 C8B, C9B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C9A) \\sim Ueq, Uanis(C9B) \\sim Ueq, Uanis(C8A) \\sim Ueq, Uanis(C8B)
\\sim Ueq, Uanis(C7B) \\sim Ueq, Uanis(C7A) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 C3A, C4A, C5A, C6A, C10A, C11A, C12A, C13A, C14A, C15A, C16A, C17A, C18A,
 C19A, C20A, C21A, C22A, C23A, C24A, C1A, C2A, C7A, C8A, C9A, C1B, C2B, C7B,
 C8B, C9B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(H3AC)=Sof(H3AD)=Sof(H10I)=Sof(H10J)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=
 Sof(H1BC)=Sof(C2B)=Sof(H2BA)=Sof(H2BB)=Sof(C7B)=Sof(H7BA)=Sof(H7BB)=Sof(H7BC)=
 Sof(C8B)=Sof(H8BA)=Sof(H8BB)=Sof(C9B)=Sof(H9BA)=Sof(H9BB)=1-FVAR(1)
 Sof(H3AA)=Sof(H3AB)=Sof(H10G)=Sof(H10H)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=
 Sof(H1AC)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(H7AC)=
 Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C1(H1A), C5(H5), C9(H9), C13(H13), C105(H105)
7.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C24(H24A,H24B), C28(H28A,H28B), C32(H32A,H32B), C3A(H3AC,
 H3AD), C3A(H3AA,H3AB), C4A(H4AA,H4AB), C5A(H5AA,H5AB), C6A(H6AA,H6AB),
 C10A(H10I,H10J), C10A(H10G,H10H), C11A(H11A,H11B), C12A(H12A,H12B), C14A(H14A,
 H14B), C15A(H15A,H15B), C16A(H16A,H16B), C17A(H17A,H17B), C18A(H18A,H18B),
 C20A(H20C,H20D), C21A(H21A,H21B), C22A(H22A,H22B), C23A(H23A,H23B), C24A(H24C,
 H24D), C2A(H2AA,H2AB), C8A(H8AA,H8AB), C9A(H9AA,H9AB), C2B(H2BA,H2BB),
 C8B(H8BA,H8BB), C9B(H9BA,H9BB), C106(H10K,H10L), C107(H10M,H10N), C108(H10O,
 H10P), C109(H10Q,H10R), C110(H11C,H11D)
7.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C7(H7), C11(H11), C15(H15)
7.d Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C43(H43A,H43B,
 H43C), C44(H44A,H44B,H44C), C45(H45A,H45B,H45C), C49(H49A,H49B,H49C), C50(H50A,
 H50B,H50C), C55(H55A,H55B,H55C), C56(H56A,H56B,H56C), C57(H57A,H57B,H57C),
 C61(H61A,H61B,H61C), C62(H62A,H62B,H62C), C63(H63A,H63B,H63C), C67(H67A,H67B,
 H67C), C68(H68A,H68B,H68C), C73(H73A,H73B,H73C), C74(H74A,H74B,H74C), C75(H75A,
 H75B,H75C), C79(H79A,H79B,H79C), C80(H80A,H80B,H80C), C81(H81A,H81B,H81C),
 C85(H85A,H85B,H85C), C86(H86A,H86B,H86C), C91(H91A,H91B,H91C), C92(H92A,H92B,
 H92C), C93(H93A,H93B,H93C), C97(H97A,H97B,H97C), C98(H98A,H98B,H98C), C99(H99A,
 H99B,H99C), C103(H10A,H10B,H10C), C104(H10D,H10E,H10F), C13A(H13A,H13B,H13C),
 C19A(H19A,H19B,H19C), C1A(H1AA,H1AB,H1AC), C7A(H7AA,H7AB,H7AC), C1B(H1BA,H1BB,
 H1BC), C7B(H7BA,H7BB,H7BC), C112(H11E,H11F,H11G)
;
_shelx_res_checksum              62645
_shelx_hkl_checksum              45562
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-06-08
_olex2_date_sample_submission    2016-06-03
_olex2_submission_original_sample_id d160815_25_1
_olex2_submission_special_instructions 'No special instructions were received'