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_1520561
_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 H44 F6 O14 S2, (C6 H14)'
_chemical_formula_sum            'C51 H58 F6 O14 S2'
_chemical_formula_weight         1073.09
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2014-06-16
_audit_creation_method
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_audit_update_record
;
2015-02-24 deposited with the CCDC.
2015-06-01 downloaded from the CCDC.
;
_cell_angle_alpha                88.271(4)
_cell_angle_beta                 83.035(3)
_cell_angle_gamma                86.352(4)
_cell_formula_units_Z            2
_cell_length_a                   11.2709(6)
_cell_length_b                   11.7647(6)
_cell_length_c                   20.1194(9)
_cell_measurement_reflns_used    1594
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.817
_cell_measurement_theta_min      6.194
_cell_volume                     2642.1(2)
_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    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.893
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Quazar optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_unetI/netI     0.0778
_diffrn_reflns_Laue_measured_fraction_full 0.893
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            8298
_diffrn_reflns_point_group_measured_fraction_full 0.893
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         65.337
_diffrn_reflns_theta_min         6.194
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    1.651
_exptl_absorpt_correction_T_max  0.752590
_exptl_absorpt_correction_T_min  0.598233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0493 before and 0.0267 after correction.
 The Ratio of minimum to maximum transmission not present.
 The \l/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.0429 before and 0.0255 after correction.
 The Ratio of minimum to maximum transmission is 0.79.
 The \l/2 correction factor is Not presentFinal HKLF 4 output contains 17536 reflections, Rint = 0.0558
 (4141 with I > 3sig(I), Rint = 0.0322)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       plate
_exptl_crystal_F_000             1124
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane/DCM'
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.701
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     753
_refine_ls_number_reflns         8298
_refine_ls_number_restraints     1187
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.1483
_refine_ls_R_factor_gt           0.0960
_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^)+(0.1666P)^2^+1.4052P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2518
_refine_ls_wR_factor_ref         0.2897
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5057
_reflns_number_total             8298
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01418_si_002.cif
_cod_data_source_block           n3581
_cod_depositor_comments
'Adding full bibliography for 1520561--1520566.cif.'
_cod_database_code               1520561
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.715
_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
 C7S-C8S = C9S-C8S = C10S-C9S = C11S-C10S = C12S-C11S
 1.53 with sigma of 0.01
 C7S-C9S = C8S-C10S
 2.55 with sigma of 0.02
 C12S-C10S = C11S-C9S
 2.55 with sigma of 0.02
 C7S-C8S \\sim C9S-C8S \\sim C10S-C9S \\sim C11S-C10S \\sim C12S-C11S
 with sigma of 0.01
 C7S-C9S \\sim C8S-C10S \\sim C12S-C10S \\sim C11S-C9S \\sim C3S-C5S \\sim
C4S-C6S \\sim C1S-C3S \\sim C2S-
 C4S
 with sigma of 0.001
 S0-O12 \\sim S001-O12
 with sigma of 0.02
 S0-O13A \\sim S0-O14A \\sim S001-O13 \\sim S001-O14
 with sigma of 0.02
 S0-C45A \\sim S001-C45
 with sigma of 0.02
 F6-C45 \\sim F5-C45 \\sim F4-C45 \\sim F4A-C45A \\sim F6A-C45A \\sim F5A-C45A
 with sigma of 0.02
 O1-C7 \\sim O1A-C7A
 with sigma of 0.01
 O1-C5 \\sim O1A-C5
 with sigma of 0.01
 S001-O12 \\sim S0-O12 \\sim S0-O14A \\sim S001-O13 \\sim S0-O13A \\sim S001-O14
 with sigma of 0.01
 S001-C45 \\sim S0-C45A
 with sigma of 0.01
 F6A-C45A \\sim F5-C45 \\sim F4A-C45A \\sim F4-C45 \\sim F5A-C45A \\sim F6-C45
 with sigma of 0.01
3. Rigid bond restraints
 S001, F4, F5, F6, O12, O13, O14, C45, S0, O13A, O14A, F4A, F5A, F6A, C45A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O1A, O1, C7A, C7
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O1, O1A, C7, C7A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C5S, C4S, C6S, C3S, C2S, C1S
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C4S, C1S, C2S, C7S, C3S, C8S, C9S, C5S, C10S, C6S, C11S, C12S
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C4S, C1S, C2S, C3S, C5S, C6S, C8S, C12S, C11S, C10S, C9S, C7S
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
S001 \\sim F4 \\sim F5 \\sim F6 \\sim O12 \\sim O13 \\sim O14 \\sim C45 \\sim
S0 \\sim O13A \\sim O14A \\sim F4A \\sim F5A \\sim F6A \\sim C45A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02
O1A \\sim O1 \\sim C7A \\sim C7: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08
O1 \\sim O1A \\sim C7A \\sim C7: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
C5S \\sim C4S \\sim C6S \\sim C3S \\sim C2S \\sim C1S: within 1.7A with sigma
of 0.01 and sigma for terminal atoms of 0.02
C4S \\sim C1S \\sim C2S \\sim C7S \\sim C3S \\sim C8S \\sim C9S \\sim C5S \\sim
C10S \\sim C6S \\sim C11S \\sim C12S: within 1.7A with sigma of 0.01 and sigma
for terminal atoms of 0.02
C4S \\sim C1S \\sim C2S \\sim C3S \\sim C5S \\sim C6S \\sim C8S \\sim C12S
\\sim C11S \\sim C10S \\sim C9S \\sim C7S: within 1.7A with sigma of 0.01 and
sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(C12S)=Sof(H12A)=Sof(H12B)=Sof(H12C)=Sof(C7S)=Sof(H7SA)=Sof(H7SB)=
 Sof(H7SC)=Sof(C8S)=Sof(H8SA)=Sof(H8SB)=Sof(C9S)=Sof(H9SA)=Sof(H9SB)=Sof(C10S)=
 Sof(H10A)=Sof(H10B)=Sof(C11S)=Sof(H11A)=Sof(H11B)=1-FVAR(1)
 Sof(C1S)=Sof(H1SA)=Sof(H1SB)=Sof(H1SC)=Sof(C2S)=Sof(H2SA)=Sof(H2SB)=Sof(C3S)=
 Sof(H3SA)=Sof(H3SB)=Sof(C4S)=Sof(H4SA)=Sof(H4SB)=Sof(C5S)=Sof(H5SA)=Sof(H5SB)=
 Sof(C6S)=Sof(H6SA)=Sof(H6SB)=Sof(H6SC)=FVAR(1)
 Sof(S0)=Sof(O13A)=Sof(O14A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=Sof(C45A)=1-FVAR(2)
 Sof(S001)=Sof(F4)=Sof(F5)=Sof(F6)=Sof(O13)=Sof(O14)=Sof(C45)=FVAR(2)
 Sof(O1A)=Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(H7AC)=1-FVAR(3)
 Sof(O1)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(H7C)=FVAR(3)
7.a Free rotating group:
 C1S(C2S,C3S,C4S,C5S,C6S,C12S,C7S,C8S,C9S,C10S,C11S,S0,O13A,O14A,F4A,F5A,F6A,
 C45A)
7.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C16(H16A,H16B), C25(H25A,H25B), C34(H34A,H34B), C43(H43A,H43B),
 C2S(H2SA,H2SB), C3S(H3SA,H3SB), C4S(H4SA,H4SB), C5S(H5SA,H5SB), C8S(H8SA,H8SB),
  C9S(H9SA,H9SB), C10S(H10A,H10B), C11S(H11A,H11B)
7.c Me refined with riding coordinates:
 C7(H7A,H7B,H7C), C15(H15A,H15B,H15C), C1S(H1SA,H1SB,H1SC), C6S(H6SA,H6SB,
 H6SC), C12S(H12A,H12B,H12C), C7A(H7AA,H7AB,H7AC)
7.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C11(H11), C14(H14), C19(H19), C22(H22), C28(H28), C31(H31),
 C37(H37), C40(H40)
7.e Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C32(H32A,H32B,H32C), C33(H33A,H33B,
 H33C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C), C7S(H7SA,H7SB,H7SC)
;
_shelx_res_checksum              42760
_shelx_hkl_checksum              38608
_olex2_submission_original_sample_id n3581
_olex2_submission_special_instructions 'No special instructions were received'