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

data_7244904
_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, 2(C H2 Cl2), 2(C6 H12 N4)'
_chemical_formula_sum            'C54 H56 Cl4 I4 N8 O4'
_chemical_formula_weight         1530.46
_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             2022-01-17
_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.
;
_cell_angle_alpha                100.754(4)
_cell_angle_beta                 90.152(4)
_cell_angle_gamma                105.402(4)
_cell_formula_units_Z            4
_cell_length_a                   13.1998(18)
_cell_length_b                   14.997(2)
_cell_length_c                   30.958(4)
_cell_measurement_reflns_used    9040
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.605
_cell_measurement_theta_min      2.873
_cell_volume                     5795.7(13)
_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      100
_diffrn_detector_area_resol_mean 7.4
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 venture PhotonII area detector'
_diffrn_measurement_method       'omega and theta scans'
_diffrn_radiation_monochromator  'multilayer mirror optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            137466
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.771
_diffrn_reflns_theta_min         2.012
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    2.386
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1492 before and 0.0844 after correction. The Ratio of minimum to maximum transmission is 0.7640. 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    1.754
_exptl_crystal_description       plate
_exptl_crystal_F_000             2992
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         3.585
_refine_diff_density_min         -1.875
_refine_diff_density_rms         0.211
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1343
_refine_ls_number_reflns         22020
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0743
_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^)+(0.0757P)^2^+98.2766P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1778
_refine_ls_wR_factor_ref         0.1919
_reflns_Friedel_coverage         0.000
_reflns_number_gt                16956
_reflns_number_total             22020
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00193d2.cif
_cod_data_source_block           1-2HMTA_fbo09mbahxdc_0m
_cod_original_cell_volume        5795.8(14)
_cod_database_code               7244904
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.832
_shelx_estimated_absorpt_t_min   0.701
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 Cl1S-C1S = Cl2S-C1S = Cl6S-C3S = Cl5S-C3S
 1.7 with sigma of 0.02
 C4T-Cl7T
 1.7 with sigma of 0.02
 C4T-Cl8T
 1.7 with sigma of 0.02
 Cl7S-C4S = Cl8S-C4S
 1.7 with sigma of 0.02
 Cl5T-C3T = Cl6T-C3T
 1.7 with sigma of 0.02
 Cl3T-C2T = Cl4T-C2T
 1.7 with sigma of 0.02
 Cl3S-C2S = Cl4S-C2S
 1.7 with sigma of 0.02
 Cl5S-Cl6S
 2.8 with sigma of 0.04
 Cl7S-Cl8S
 2.8 with sigma of 0.04
 Cl6T-Cl5T
 2.8 with sigma of 0.04
 Cl3T-Cl4T
 2.8 with sigma of 0.04
 Cl3S-Cl4S
 2.8 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(Cl8S) = Uanis(C4S) = Uanis(Cl7S)
Uanis(Cl7T) = Uanis(C4T) = Uanis(Cl8T)
Uanis(Cl6S) = Uanis(C3S) = Uanis(Cl5S)
Uanis(Cl5T) = Uanis(Cl6T) = Uanis(C3T)
Uanis(Cl3S) = Uanis(C2S) = Uanis(Cl4S)
Uanis(Cl3T) = Uanis(C2T) = Uanis(Cl4T)
4. Others
 Sof(Cl5T)=Sof(C3T)=Sof(H3TA)=Sof(H3TB)=Sof(Cl6T)=1-FVAR(1)
 Sof(Cl5S)=Sof(Cl6S)=Sof(C3S)=Sof(H3SA)=Sof(H3SB)=FVAR(1)
 Fixed Sof: Cl3S(0.6) Cl7T(0.5) Cl8T(0.5) Cl4S(0.6) C2S(0.6) H2SA(0.6)
 H2SB(0.6) C4T(0.5) H4TA(0.5) H4TB(0.5) Cl8S(0.5) C4S(0.5) H4SA(0.5) H4SB(0.5)
 Cl7S(0.5) Cl3T(0.4) C2T(0.4) H2TA(0.4) H2TB(0.4) Cl4T(0.4)
5.a Secondary CH2 refined with riding coordinates:
 C55(H55A,H55B), C33(H33A,H33B), C281(H28C,H28D), C211(H21C,H21D), C381(H38C,
 H38D), C71(H71A,H71B), C23(H23A,H23B), C322(H32A,H32B), C142(H14A,H14B),
 C43(H43A,H43B), C72(H72A,H72B), C141(H14C,H14D), C382(H38A,H38B), C35(H35E,
 H35F), C53(H53A,H53B), C15(H15A,H15B), C321(H32C,H32D), C212(H21A,H21B),
 C282(H28A,H28B), C14(H14E,H14F), C25(H25A,H25B), C352(H35A,H35B), C351(H35C,
 H35D), C292(H29A,H29B), C65(H65A,H65B), C13(H13A,H13B), C45(H45A,H45B),
 C34(H34A,H34B), C291(H29C,H29D), C63(H63A,H63B), C16(H16A,H16B), C56(H56A,
 H56B), C36(H36A,H36B), C24(H24A,H24B), C46(H46A,H46B), C26(H26A,H26B),
 C54(H54A,H54B), C1S(H1SA,H1SB), C66(H66A,H66B), C042(H04A,H04B), C44(H44A,
 H44B), C2S(H2SA,H2SB), C3S(H3SA,H3SB), C4T(H4TA,H4TB), C3T(H3TA,H3TB),
 C4S(H4SA,H4SB), C2T(H2TA,H2TB)
5.b Aromatic/amide H refined with riding coordinates:
 C251(H251), C232(H232), C252(H252), C242(H242), C231(H231), C112(H112),
 C161(H161), C91(H91), C32(H32), C182(H182), C41(H41), C241(H241), C52(H52),
 C31(H31), C102(H102), C92(H92), C181(H181), C51(H51), C172(H172), C42(H42),
 C111(H111), C162(H162), C171(H171), C101(H101)
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_olex2_exptl_crystal_mounting_method cryoloop
_olex2_submission_special_instructions 'No special instructions were received'