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_1520565
_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      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 110.288(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.0373(10)
_cell_length_b                   11.9982(5)
_cell_length_c                   22.7155(10)
_cell_measurement_reflns_used    5158
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      63.324
_cell_measurement_theta_min      3.684
_cell_volume                     5633.5(4)
_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      100.08
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.897
_diffrn_measured_fraction_theta_max 0.988
_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_R_equivalents  0.0648
_diffrn_reflns_av_unetI/netI     0.0815
_diffrn_reflns_Laue_measured_fraction_full 0.897
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            24785
_diffrn_reflns_point_group_measured_fraction_full 0.897
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         63.664
_diffrn_reflns_theta_min         2.137
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    2.050
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.6509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0878 before and 0.0702 after correction.
The Ratio of minimum to maximum transmission is 0.8651.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       needle
_exptl_crystal_F_000             2472
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane/DCM'
_exptl_crystal_size_max          0.426
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.011
_refine_diff_density_max         1.370
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     721
_refine_ls_number_reflns         9147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0854
_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^)+(0.1279P)^2^+14.3265P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2322
_refine_ls_wR_factor_ref         0.2482
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6891
_reflns_number_total             9147
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01418_si_002.cif
_cod_data_source_block           n3604
_cod_depositor_comments
'Adding full bibliography for 1520561--1520566.cif.'
_cod_original_cell_volume        5633.6(4)
_cod_database_code               1520565
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.475
_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.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)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C11(H11), C14(H14), C20(H20), C23(H23), C29(H29), C32(H32),
 C38(H38), C41(H41)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C25(H25A,H25B,
 H25C), C35(H35A,H35B,H35C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C), C46(H46A,
 H46B,H46C), C51(H51A,H51B,H51C)
;
_shelx_res_checksum              24074
_shelx_hkl_checksum              26492
_olex2_submission_special_instructions 'No special instructions were received'