Tetraiodoethynyl resorcinarene cavitands as multivalent halogen bond donors
L. Turunen; N. K. Beyeh; F. Pan; A. Valkonen; K. Rissanen; Chem.Commun. 50 (2014) 15920–; doi:10.1039/C4cc07771G

data_7116130
_publ_section_title
;
 Tetraiodoethynyl resorcinarene cavitands as multivalent halogen bond
 donors
;
_journal_name_full               Chem.Commun.
_journal_page_first              15920
_journal_paper_doi               10.1039/C4cc07771G
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety
'C68 H76 I4 O8, C H Cl3, 2(Br), H2 O, 2(C3 H6 O), 2(C12 H28 N)'
_chemical_formula_sum            'C99 H147 Br2 Cl3 I4 N2 O11'
_chemical_formula_weight         2314.95
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-09-02
_audit_creation_method
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.621(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.4168(7)
_cell_length_b                   24.5753(13)
_cell_length_c                   19.1408(6)
_cell_measurement_reflns_used    9294
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      74.2040
_cell_measurement_theta_min      3.8850
_cell_volume                     11005.6(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector_area_resol_mean 5.1977
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details
;
  1 omega  -81.00  -15.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  125.0000  -60.0000 66

  2 omega -106.00  -13.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  -57.0000 -150.0000 93

  3 omega   30.00   70.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3676 -125.0000 -180.0000 40

  4 omega   29.00  109.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   30.0000 80

  5 omega   93.00  177.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  150.0000 84

  6 omega   42.00  116.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -180.0000 74

  7 omega   65.00   99.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -120.0000 34

  8 omega   36.00   89.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   30.0000 53

  9 omega   36.00   84.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  120.0000 48

 10 omega   39.00   97.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -150.0000 58
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0600975000
_diffrn_orient_matrix_UB_12      0.0156838000
_diffrn_orient_matrix_UB_13      -0.0480250000
_diffrn_orient_matrix_UB_21      -0.0231456000
_diffrn_orient_matrix_UB_22      -0.0555448000
_diffrn_orient_matrix_UB_23      0.0160652000
_diffrn_orient_matrix_UB_31      -0.0139447000
_diffrn_orient_matrix_UB_32      0.0244463000
_diffrn_orient_matrix_UB_33      0.0669416000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0708
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            40510
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        70.000
_diffrn_reflns_theta_max         76.722
_diffrn_reflns_theta_min         3.006
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    10.824
_exptl_absorpt_correction_T_max  0.420
_exptl_absorpt_correction_T_min  0.208
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       block
_exptl_crystal_F_000             4704
_exptl_crystal_size_max          0.1692
_exptl_crystal_size_mid          0.0921
_exptl_crystal_size_min          0.0789
_refine_diff_density_max         1.829
_refine_diff_density_min         -1.802
_refine_diff_density_rms         0.119
_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     1163
_refine_ls_number_reflns         22103
_refine_ls_number_restraints     68
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0567
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0684P)^2^+14.2606P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1431
_refine_ls_wR_factor_ref         0.1635
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15779
_reflns_number_total             22103
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc07771g2.cif
_cod_data_source_block           4c.BrTPA
_cod_database_code               7116130
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C68 H76 I4 O8 Br2'
_reflns_odcompleteness_completeness 98.70
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O12-H12A = O12-H12B
 0.84 with sigma of 0.02
 C96B-C97B = C96B-C98B
 1.45 with sigma of 0.02
 C96B-O10B
 1.25 with sigma of 0.02
 C102-Cl1 \\sim C102-Cl2 \\sim C102-Cl3 \\sim C103-Cl1 \\sim C103-Cl2 \\sim
C103-Cl3
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C62) \\sim Ueq, Uanis(C102) \\sim Ueq, Uanis(C103) \\sim Ueq, Uanis(C62)
\\sim Ueq, Uanis(C68) \\sim Ueq, Uanis(O10B) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C55) \\sim Ueq, Uanis(C96B) \\sim Ueq, Uanis(C98B) \\sim Ueq: with sigma
of 0.02 and sigma for terminal atoms of 0.04
4. Others
 Sof(C103)=Sof(H103)=1-FVAR(1)
 Sof(C102)=Sof(H102)=FVAR(1)
 Sof(O10B)=Sof(C96B)=Sof(C97B)=Sof(H97D)=Sof(H97E)=Sof(H97F)=Sof(C98B)=
 Sof(H98D)=Sof(H98E)=Sof(H98F)=1-FVAR(2)
 Sof(O10)=Sof(C96)=Sof(C97)=Sof(H97A)=Sof(H97B)=Sof(H97C)=Sof(C98)=Sof(H98A)=
 Sof(H98B)=Sof(H98C)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C28(H28), C14(H14), C21(H21), C7(H7), C102(H102), C103(H103)
5.b Secondary CH2 refined with riding coordinates:
 C51(H51A,H51B), C55(H55A,H55B), C31(H31A,H31B), C30(H30A,H30B), C59(H59A,
 H59B), C34(H34A,H34B), C52(H52A,H52B), C57(H57A,H57B), C29(H29A,H29B),
 C33(H33A,H33B), C58(H58A,H58B), C54(H54A,H54B), C53(H53A,H53B), C35(H35A,H35B),
  C36(H36A,H36B), C32(H32A,H32B), C63(H63A,H63B), C64(H64A,H64B), C65(H65A,
 H65B), C45(H45A,H45B), C47(H47A,H47B), C46(H46A,H46B), C48(H48A,H48B),
 C49(H49A,H49B), C60(H60A,H60B), C61(H61A,H61B), C67(H67A,H67B), C66(H66A,H66B),
  C69(H69A,H69B), C75(H75A,H75B), C72(H72A,H72B), C78(H78A,H78B), C76(H76A,
 H76B), C73(H73A,H73B), C70(H70A,H70B), C79(H79A,H79B), C84(H84A,H84B),
 C85(H85A,H85B), C87(H87A,H87B), C90(H90A,H90B), C81(H81A,H81B), C82(H82A,H82B),
  C91(H91A,H91B), C88(H88A,H88B)
5.c Aromatic/amide H refined with riding coordinates:
 C27(H27), C20(H20), C13(H13), C4(H4)
5.d Idealised Me refined as rotating group:
 C56(H56A,H56B,H56C), C50(H50A,H50B,H50C), C68(H68A,H68B,H68C), C62(H62A,H62B,
 H62C), C95(H95A,H95B,H95C), C94(H94A,H94B,H94C), C71(H71A,H71B,H71C), C80(H80A,
 H80B,H80C), C74(H74A,H74B,H74C), C77(H77A,H77B,H77C), C86(H86A,H86B,H86C),
 C83(H83A,H83B,H83C), C92(H92A,H92B,H92C), C89(H89A,H89B,H89C), C97(H97A,H97B,
 H97C), C98(H98A,H98B,H98C), C97B(H97D,H97E,H97F), C98B(H98D,H98E,H98F)
;
_olex2_submission_special_instructions 'No special instructions were received'