Halogen-bonded architectures of multivalent calix[4]arenes
Gullo, Maria Chiara; Marchiò, Luciano; Casnati, Alessandro; Baldini, Laura; CrystEngComm  (2022) –; doi:10.1039/D2CE00193D

data_7244903
_publ_section_title
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 Halogen-bonded architectures of multivalent calix[4]arenes
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_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00193D
_journal_year                    2022
_chemical_formula_moiety         'C40 H28 I4 O4, 4(C4 H8 O)'
_chemical_formula_sum            'C56 H60 I4 O8'
_chemical_formula_weight         1368.64
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-20 deposited with the CCDC.	2022-03-17 downloaded from the CCDC.
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_cell_angle_alpha                112.406(2)
_cell_angle_beta                 101.238(2)
_cell_angle_gamma                99.482(2)
_cell_formula_units_Z            2
_cell_length_a                   13.2357(16)
_cell_length_b                   15.3241(18)
_cell_length_c                   15.3955(19)
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    200
_cell_measurement_theta_max      26.340
_cell_measurement_theta_min      2.299
_cell_volume                     2731.4(6)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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_temperature      200
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Smart APEXII CCD'
_diffrn_measurement_method       'theta & omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            34973
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.816
_diffrn_reflns_theta_min         1.490
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    2.333
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1074 before and 0.0441 after correction. The Ratio of minimum to maximum transmission is 0.7269. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_description       prism
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.760
_refine_diff_density_min         -1.548
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     705
_refine_ls_number_reflns         11670
_refine_ls_number_restraints     110
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0382P)^2^+4.0417P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.1002
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9066
_reflns_number_total             11670
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00193d2.cif
_cod_data_source_block           4-4THF_aro12thf_0m
_cod_database_code               7244903
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.707
_shelx_estimated_absorpt_t_min   0.561
_olex2_refinement_description
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1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 O4S-C16S = O4S-C13S
 1.42 with sigma of 0.02
 C14S-C13S = C15S-C14S = C16S-C15S
 1.5 with sigma of 0.02
 C16T-C15T = C15T-C14T = C14T-C13T
 1.5 with sigma of 0.02
 O4T-C13T = O4T-C16T
 1.42 with sigma of 0.02
 O2T-C8T = O2T-C5T
 1.42 with sigma of 0.02
 C6T-C5T = C7T-C6T = C8T-C7T
 1.5 with sigma of 0.02
 O2S-C5S = O2S-C8S
 1.42 with sigma of 0.02
 C6S-C5S = C7S-C6S = C8S-C7S
 1.5 with sigma of 0.02
3. Rigid body (RIGU) restrains
 O4S, C13S, C16S, C14S, H13A, H13B, C15S, H16A, H16B, H15A, H15B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O4T, C16T, C13T, H16C, H16D, C15T, C14T, H13C, H13D, H15C, H15D, H14E, H14F
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C7T, O2T, C8T, C5T, H8TA, H8TB, C6T, H5TA, H5TB, H7TA, H7TB, H6TA, H6TB
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(O4T)=Sof(C16T)=Sof(H16C)=Sof(H16D)=Sof(C14T)=Sof(H14E)=Sof(H14F)=
 Sof(C15T)=Sof(H15C)=Sof(H15D)=Sof(C13T)=Sof(H13C)=Sof(H13D)=1-FVAR(1)
 Sof(O4S)=Sof(C14S)=Sof(H14C)=Sof(H14D)=Sof(C13S)=Sof(H13A)=Sof(H13B)=
 Sof(C15S)=Sof(H15A)=Sof(H15B)=Sof(C16S)=Sof(H16A)=Sof(H16B)=FVAR(1)
 Sof(O2T)=Sof(C6T)=Sof(H6TA)=Sof(H6TB)=Sof(C7T)=Sof(H7TA)=Sof(H7TB)=Sof(C8T)=
 Sof(H8TA)=Sof(H8TB)=Sof(C5T)=Sof(H5TA)=Sof(H5TB)=1-FVAR(2)
 Sof(O2S)=Sof(C6S)=Sof(H6SA)=Sof(H6SB)=Sof(C7S)=Sof(H7SA)=Sof(H7SB)=Sof(C8S)=
 Sof(H8SA)=Sof(H8SB)=Sof(C5S)=Sof(H5SA)=Sof(H5SB)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C21(H21A,H21B), C28(H28A,H28B), C29(H29A,H29B), C32(H32A,H32B),
 C14(H14A,H14B), C38(H38A,H38B), C35(H35A,H35B), C12S(H12A,H12B), C9S(H9SA,
 H9SB), C11S(H11A,H11B), C2S(H2SA,H2SB), C1S(H1SA,H1SB), C4S(H4SA,H4SB),
 C10S(H10A,H10B), C3S(H3SA,H3SB), C14S(H14C,H14D), C13S(H13A,H13B), C15S(H15A,
 H15B), C6S(H6SA,H6SB), C7S(H7SA,H7SB), C16S(H16A,H16B), C8S(H8SA,H8SB),
 C5S(H5SA,H5SB), C16T(H16C,H16D), C14T(H14E,H14F), C15T(H15C,H15D), C13T(H13C,
 H13D), C6T(H6TA,H6TB), C7T(H7TA,H7TB), C8T(H8TA,H8TB), C5T(H5TA,H5TB)
5.b Aromatic/amide H refined with riding coordinates:
 C23(H23), C24(H24), C5(H5), C3(H3), C25(H25), C9(H9), C18(H18), C16(H16),
 C17(H17), C10(H10), C11(H11), C4(H4)
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_olex2_exptl_crystal_mounting_method cryoloop
_olex2_submission_special_instructions 'No special instructions were received'