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_1520562
_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_absolute_configuration ad
_chemical_formula_moiety         'C45 H44 F6 O14 S2, C H2 Cl2'
_chemical_formula_sum            'C46 H46 Cl2 F6 O14 S2'
_chemical_formula_weight         1071.85
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-05-23
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2015-02-24 deposited with the CCDC.
2015-06-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.1589(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.6160(3)
_cell_length_b                   18.2419(5)
_cell_length_c                   11.6170(3)
_cell_measurement_reflns_used    7381
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.042
_cell_measurement_theta_min      4.521
_cell_volume                     2455.14(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      99.98
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.932
_diffrn_measured_fraction_theta_max 0.984
_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  0.0164
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.932
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8390
_diffrn_reflns_point_group_measured_fraction_full 0.687
_diffrn_reflns_point_group_measured_fraction_max 0.726
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         65.062
_diffrn_reflns_theta_min         2.422
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    2.756
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0444 before and 0.0306 after correction.
The Ratio of minimum to maximum transmission is 0.8586.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_description       plate
_exptl_crystal_F_000             1108
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane/DCM'
_exptl_crystal_size_max          0.258
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.796
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 1856 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.073(14)
_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     667
_refine_ls_number_reflns         6088
_refine_ls_number_restraints     74
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0782P)^2^+2.0201P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1264
_reflns_Friedel_coverage         0.472
_reflns_Friedel_fraction_full    0.442
_reflns_Friedel_fraction_max     0.467
_reflns_number_gt                5908
_reflns_number_total             6088
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01418_si_002.cif
_cod_data_source_block           n3539a
_cod_depositor_comments
'Adding full bibliography for 1520561--1520566.cif.'
_cod_database_code               1520562
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.863
_shelx_estimated_absorpt_t_min   0.537
_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
 Cl1T-C1T \\sim Cl2T-C1T \\sim Cl2S-C1S \\sim Cl1S-C1S
 with sigma of 0.01
3. Rigid bond restraints
 C1T, Cl2T, Cl1T, C1S, Cl1S, Cl2S
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C1T \\sim Cl2T \\sim Cl1T \\sim C1S \\sim Cl1S \\sim Cl2S: within 1.7A with
sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C1T) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
5. Others
 Sof(Cl1T)=Sof(Cl2T)=Sof(C1T)=Sof(H1TA)=Sof(H1TB)=1-FVAR(1)
 Sof(Cl1S)=Sof(Cl2S)=Sof(C1S)=Sof(H1SA)=Sof(H1SB)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C17(H17A,H17B), C019(H01A,H01B), C25(H25A,H25B), C34(H34A,H34B),
 C1S(H1SA,H1SB), C1T(H1TA,H1TB)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C11(H11), C14(H14), C19(H19), C22(H22), C27(H27), C30(H30),
 C36(H36), C39(H39)
6.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C24(H24A,H24B,
 H24C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C41(H41A,H41B,H41C), C42(H42A,
 H42B,H42C)
;
_shelx_res_checksum              48475
_shelx_hkl_checksum              59793