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_1520563
_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 H47 F3 O12 S, 1.13(C H2 Cl2), 0.44(C6 H14)'
_chemical_formula_sum            'C48.75 H55.04 Cl2.25 F3 O12 S'
_chemical_formula_weight         1001.86
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2014-06-13
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   35.9931(11)
_cell_length_b                   12.0648(4)
_cell_length_c                   11.3690(4)
_cell_measurement_reflns_used    9208
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.465
_cell_measurement_theta_min      3.888
_cell_volume                     4937.0(3)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0281
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_laue_measured_fraction_full 0.989
_diffrn_reflns_laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            42443
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.611
_diffrn_reflns_theta_min         2.455
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    2.316
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0562 before and 0.0451 after correction.
The Ratio of minimum to maximum transmission is 0.8227.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       block
_exptl_crystal_F_000             2099
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane/DCM'
_exptl_crystal_size_max          0.366
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.176
_refine_diff_density_max         1.030
_refine_diff_density_min         -0.800
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details
;
 Flack x determined using 4068 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.285(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     671
_refine_ls_number_reflns         8747
_refine_ls_number_restraints     573
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0750
_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^)+(0.0878P)^2^+14.5159P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2026
_refine_ls_wR_factor_ref         0.2029
_reflns_Friedel_coverage         0.878
_reflns_friedel_fraction_full    0.970
_reflns_friedel_fraction_max     0.970
_reflns_number_gt                8725
_reflns_number_total             8747
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01418_si_002.cif
_cod_data_source_block           n3579
_cod_depositor_comments
'Adding full bibliography for 1520561--1520566.cif.'
_cod_database_code               1520563
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.686
_shelx_estimated_absorpt_t_min   0.484
_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
 Cl1-C46 \\sim Cl2-C46 \\sim Cl3-C47 \\sim Cl4-C47
 with sigma of 0.02
 Cl1-Cl2 \\sim Cl3-Cl4
 with sigma of 0.02
 C49-C48 \\sim C50-C49 \\sim C51-C50 \\sim C52-C51 \\sim C53-C52 \\sim C54-C53
 with sigma of 0.02
 C54-C52 \\sim C53-C51 \\sim C50-C48 \\sim C49-C51 \\sim C50-C52
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C52) = Uanis(Cl3)
4. 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
5. Others
 Sof(C49)=Sof(H49A)=Sof(H49B)=Sof(C50)=Sof(H50A)=Sof(H50B)=Sof(C51)=Sof(H51A)=
 Sof(H51B)=Sof(C52)=Sof(H52A)=Sof(H52B)=Sof(C53)=Sof(H53A)=Sof(H53B)=1-FVAR(1)
 Sof(C48)=Sof(H48A)=Sof(H48B)=Sof(H48C)=Sof(C54)=Sof(H54A)=Sof(H54B)=Sof(H54C)=
 0.5*(1-FVAR(2))
 Sof(Cl1)=Sof(Cl2)=Sof(C46)=Sof(H46A)=Sof(H46B)=Sof(Cl3)=Sof(Cl4)=Sof(C47)=
 Sof(H47A)=Sof(H47B)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C18(H18A,H18B), C27(H27A,H27B), C36(H36A,H36B), C45(H45A,H45B),
 C46(H46A,H46B), C47(H47A,H47B), C49(H49A,H49B), C50(H50A,H50B), C51(H51A,H51B),
  C52(H52A,H52B), C53(H53A,H53B)
6.b Me refined with riding coordinates:
 C48(H48A,H48B,H48C), C54(H54A,H54B,H54C)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C11(H11), C14(H14), C20(H20), C23(H23), C29(H29), C32(H32),
 C38(H38), C41(H41)
6.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C25(H25A,H25B,
 H25C), C26(H26A,H26B,H26C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C43(H43A,
 H43B,H43C), C44(H44A,H44B,H44C)
;
_shelx_res_checksum              59723
_shelx_hkl_checksum              47682
_olex2_submission_original_sample_id hj29-4
_olex2_submission_special_instructions 'No special instructions were received'