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_7116129
_publ_section_title
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 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, 7(C5 H5 N)'
_chemical_formula_sum            'C103 H111 I4 N7 O8'
_chemical_formula_weight         2082.58
_chemical_name_systematic
;
 ?
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_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-02-11
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.8176(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.3028(5)
_cell_length_b                   12.2692(2)
_cell_length_c                   29.3240(5)
_cell_measurement_reflns_used    9141
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      75.3830
_cell_measurement_theta_min      3.9400
_cell_volume                     9822.1(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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_environment      N~2~
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0479110000
_diffrn_orient_matrix_UB_12      0.0087794000
_diffrn_orient_matrix_UB_13      -0.0268496000
_diffrn_orient_matrix_UB_21      -0.0295087000
_diffrn_orient_matrix_UB_22      -0.0034341000
_diffrn_orient_matrix_UB_23      -0.0451612000
_diffrn_orient_matrix_UB_31      -0.0041501000
_diffrn_orient_matrix_UB_32      0.1252212000
_diffrn_orient_matrix_UB_33      0.0006448000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            19709
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        66.750
_diffrn_reflns_theta_max         76.848
_diffrn_reflns_theta_min         3.014
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    10.416
_exptl_absorpt_correction_T_max  0.232
_exptl_absorpt_correction_T_min  0.040
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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            colorless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       brick
_exptl_crystal_F_000             4216
_exptl_crystal_size_max          0.5087
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.1181
_refine_diff_density_max         1.155
_refine_diff_density_min         -0.802
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     592
_refine_ls_number_reflns         10048
_refine_ls_number_restraints     43
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0638P)^2^+6.1300P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1204
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8788
_reflns_number_total             10048
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc07771g2.cif
_cod_data_source_block           4c.Pyridine
_cod_original_cell_volume        9822.0(3)
_cod_database_code               7116129
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C60 H60 O8 N4 I4'
_reflns_odcompleteness_completeness 99.75
_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
2. Shared sites
{C31A, C31B}
3. Restrained distances
 H32B-H46
 2.1 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
N3 \\sim C45 \\sim C46 \\sim C47 \\sim C48 \\sim C49: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08
Uanis(C47) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C31A) = Uanis(C31B)
5. Others
 Sof(I1B)=1-FVAR(1)
 Sof(I1A)=FVAR(1)
 Sof(H30C)=Sof(H30D)=Sof(C31B)=Sof(H31C)=Sof(H31D)=Sof(C32B)=Sof(H32C)=
 Sof(H32D)=Sof(C33B)=Sof(H33C)=Sof(H33D)=Sof(C34B)=Sof(H34D)=Sof(H34E)=
 Sof(H34F)=1-FVAR(2)
 Sof(H30A)=Sof(H30B)=Sof(C31A)=Sof(H31A)=Sof(H31B)=Sof(C32A)=Sof(H32A)=
 Sof(H32B)=Sof(C33A)=Sof(H33A)=Sof(H33B)=Sof(C34A)=Sof(H34A)=Sof(H34B)=
 Sof(H34C)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C11(H11), C28(H28)
6.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B),
 C15(H15A,H15B), C16(H16A,H16B), C26(H26A,H26B), C27(H27A,H27B), C29(H29A,H29B),
  C30(H30A,H30B), C30(H30C,H30D), C31A(H31A,H31B), C32A(H32A,H32B), C33A(H33A,
 H33B), C31B(H31C,H31D), C32B(H32C,H32D), C33B(H33C,H33D)
6.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C23(H23), C45(H45), C46(H46), C47(H47), C48(H48), C49(H49), C50(H50),
 C51(H51), C52(H52), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39), C40(H40),
  C41(H41), C42(H42), C43(H43), C44(H44)
6.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C34A(H34A,H34B,H34C), C34B(H34D,H34E,H34F)
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