Activation-Enabled Syntheses of Functionalized Pillar[5]arene Derivatives.
Han, Jie; Hou, Xisen; Ke, Chenfeng; Zhang, Huacheng; Strutt, Nathan L.; Stern, Charlotte L.; Stoddart, J. Fraser; Organic letters 17 (2015) 3260–3263; doi:10.1021/acs.orglett.5b01418

data_1520566
_publ_section_title
;
 Activation-Enabled Syntheses of Functionalized Pillar[5]arene
 Derivatives.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3260
_journal_page_last               3263
_journal_paper_doi               10.1021/acs.orglett.5b01418
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C45 H41 F9 O16 S3, C6 H14'
_chemical_formula_sum            'C51 H55 F9 O16 S3'
_chemical_formula_weight         1191.13
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-06-24
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.23 svn.r2946 for OlexSys, GUI svn.r4855)
;
_audit_update_record
;
2015-02-24 deposited with the CCDC.
2015-06-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.6289(11)
_cell_length_b                   22.2856(13)
_cell_length_c                   24.1696(14)
_cell_measurement_reflns_used    9431
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.031
_cell_measurement_theta_min      2.333
_cell_volume                     11111.4(11)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Bruker SAINT'
_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    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.96
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1109
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            173003
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.195
_diffrn_reflns_theta_min         1.587
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.6487
_exptl_absorpt_correction_T_min  0.5661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1488 before and 0.1252 after correction.
The Ratio of minimum to maximum transmission is 0.8727.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       plate
_exptl_crystal_F_000             4944
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane/DCM'
_exptl_crystal_size_max          0.728
_exptl_crystal_size_mid          0.665
_exptl_crystal_size_min          0.264
_refine_diff_density_max         0.930
_refine_diff_density_min         -1.028
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     866
_refine_ls_number_reflns         16142
_refine_ls_number_restraints     590
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.1801
_refine_ls_R_factor_gt           0.1169
_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^)+(0.1464P)^2^+25.6452P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3006
_refine_ls_wR_factor_ref         0.3487
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9539
_reflns_number_total             16142
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01418_si_002.cif
_cod_data_source_block           n3606
_cod_depositor_comments
'Adding full bibliography for 1520561--1520566.cif.'
_cod_database_code               1520566
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.942
_shelx_estimated_absorpt_t_min   0.850
_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
 F4-C25 \\sim F5-C25 \\sim F6-C25 \\sim F4A-C25A \\sim F5A-C25A \\sim F6A-C25A
 with sigma of 0.02
 F5-F4 \\sim F6-F5 \\sim F4-F6 \\sim F5A-F4A \\sim F6A-F5A \\sim F4A-F6A
 with sigma of 0.02
 O7-O8 \\sim O8-O9 \\sim O7-O9 \\sim O7A-O8A \\sim O8A-O9A \\sim O7A-O9A
 with sigma of 0.02
 C47A-C46A \\sim C47-C46 \\sim C48A-C47A \\sim C48-C47 \\sim C49A-C48A \\sim
C49-C48 \\sim C50A-C49A ~
 C50-C49 \\sim C51A-C50A \\sim C51-C50
 with sigma of 0.02
 C46-C48 \\sim C47-C49 \\sim C51A-C49A \\sim C48A-C46A \\sim C47A-C49A \\sim
C48A-C50A \\sim C48-C50
 with sigma of 0.02
 S2A-C25A \\sim S2-C25
 with sigma of 0.02
 S2A-O7A \\sim S2A-O8A \\sim S2A-O9A \\sim S2-O8 \\sim S2-O7 \\sim S2-O9
 with sigma of 0.02
 O9-F4 \\sim O7-F5 \\sim O8-F6 \\sim O9A-F5A \\sim O7A-F4A \\sim O8A-F6A
 with sigma of 0.02
 C22-C21A \\sim C22-C21 \\sim C21A-C20A \\sim C21-C20 \\sim C20A-C19 \\sim
C20-C19 \\sim C24-C19 \\sim C24-
 C23 \\sim C23-C22
 with sigma of 0.01
3. Rigid bond restraints
 C47, C46, C48, C49, C50, C51, C48A, C47A, C49A, C46A, C50A, C51A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 S2, F4, F5, F6, O7, O8, O9, C25, S2A, F4A, F5A, F6A, O7A, O8A, O9A, C25A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C21A, C21, C20, C20A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C47 \\sim C46 \\sim C48 \\sim C49 \\sim C50 \\sim C51 \\sim C48A \\sim C47A
\\sim C49A \\sim C46A \\sim C50A \\sim C51A: within 1.7A with sigma of 0.01 and
sigma for terminal atoms of 0.02
S2 \\sim F4 \\sim F5 \\sim F6 \\sim O7 \\sim O8 \\sim O9 \\sim C25 \\sim S2A
\\sim F4A \\sim F5A \\sim F6A \\sim O7A \\sim O8A \\sim O9A \\sim C25A: within
1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
C20A \\sim C20 \\sim C21 \\sim C21A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
5. Others
 Sof(C46A)=Sof(H46D)=Sof(H46E)=Sof(H46F)=Sof(C47A)=Sof(H47C)=Sof(H47D)=
 Sof(C48A)=Sof(H48C)=Sof(H48D)=Sof(C49A)=Sof(H49C)=Sof(H49D)=Sof(C50A)=
 Sof(H50C)=Sof(H50D)=Sof(C51A)=Sof(H51D)=Sof(H51E)=Sof(H51F)=1-FVAR(1)
 Sof(C46)=Sof(H46A)=Sof(H46B)=Sof(H46C)=Sof(C47)=Sof(H47A)=Sof(H47B)=Sof(C48)=
 Sof(H48A)=Sof(H48B)=Sof(C49)=Sof(H49A)=Sof(H49B)=Sof(C50)=Sof(H50A)=Sof(H50B)=
 Sof(C51)=Sof(H51A)=Sof(H51B)=Sof(H51C)=FVAR(1)
 Sof(S2A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=Sof(O7A)=Sof(O8A)=Sof(O9A)=Sof(C25A)=
 Sof(C20A)=Sof(C21A)=Sof(H21A)=1-FVAR(2)
 Sof(S2)=Sof(F4)=Sof(F5)=Sof(F6)=Sof(O7)=Sof(O8)=Sof(O9)=Sof(C20)=Sof(C21)=
 Sof(H21)=Sof(C25)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C18(H18A,H18B), C27(H27A,H27B), C36(H36A,H36B), C45(H45A,H45B),
 C47(H47A,H47B), C48(H48A,H48B), C49(H49A,H49B), C50(H50A,H50B), C47A(H47C,
 H47D), C48A(H48C,H48D), C49A(H49C,H49D), C50A(H50C,H50D)
6.b Me refined with riding coordinates:
 C35(H35A,H35B,H35C), C51(H51A,H51B,H51C), C51A(H51D,H51E,H51F)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C12(H12), C15(H15), C21(H21), C24(H24), C30(H30), C33(H33),
 C39(H39), C42(H42), C21A(H21A)
6.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C26(H26A,H26B,
 H26C), C34(H34A,H34B,H34C), C44(H44A,H44B,H44C), C46(H46A,H46B,H46C),
 C46A(H46D,H46E,H46F)
;
_shelx_res_checksum              53152
_shelx_hkl_checksum              63300
_olex2_submission_original_sample_id n3606
_olex2_submission_special_instructions 'No special instructions were received'