Stabilization of Grignard reagents by a pillar[5]arene host - Schlenk equilibria and Grignard reactions.
Shen, Lingyi; Zhao, Yanxia; Dai, Dihua; Yang, Ying-Wei; Wu, Biao; Yang, Xiao-Juan; Chemical communications (Cambridge, England) 56 (2020) 1381–1384; doi:10.1039/c9cc08728a

data_7125911
_publ_section_title
;
 Stabilization of Grignard reagents by a pillar[5]arene host - Schlenk
 equilibria and Grignard reactions.
;
_journal_issue                   9
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1381
_journal_page_last               1384
_journal_paper_doi               10.1039/c9cc08728a
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C27.33 H58.54 Br0.13 Mg2 O2, C45 H49 O10'
_chemical_formula_sum            'C72.34 H107.54 Br0.14 Mg2 O12'
_chemical_formula_weight         1228.54
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-07-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-23 deposited with the CCDC.	2020-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                75.943(17)
_cell_angle_beta                 88.27(2)
_cell_angle_gamma                73.195(16)
_cell_formula_units_Z            2
_cell_length_a                   11.959(8)
_cell_length_b                   13.536(9)
_cell_length_c                   22.775(13)
_cell_measurement_reflns_used    9163
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.88
_cell_measurement_theta_min      2.34
_cell_volume                     3420(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.01
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 Venture photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            76891
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         25.240
_diffrn_reflns_theta_min         2.137
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7054
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1105 before and 0.0579 after correction.
The Ratio of minimum to maximum transmission is 0.9466.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1333
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   0.7452
_exptl_transmission_factor_min   0.7054
_refine_diff_density_max         0.681
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0022(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     809
_refine_ls_number_reflns         12260
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0656
_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^)+(0.0805P)^2^+3.4514P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1697
_refine_ls_wR_factor_ref         0.1826
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9758
_reflns_number_total             12260
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc08728a2.cif
_cod_data_source_block           5
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        3421(4)
_cod_database_code               7125911
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.950
_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
 C6-C7
 1.54 with sigma of 0.01
3. Others
 Sof(Br1)=1-FVAR(1)
 Sof(C6)=Sof(H6A)=Sof(H6B)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(C8)=Sof(H8A)=Sof(H8B)=
 Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B),
 C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B),
 C14(H14A,H14B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B),
  C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,
 H25B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B), C37(H37A,H37B),
 C46(H46A,H46B), C55(H55A,H55B), C64(H64A,H64B), C73(H73A,H73B)
4.b Aromatic/amide H refined with riding coordinates:
 C35(H35), C41(H41), C44(H44), C50(H50), C53(H53), C59(H59), C62(H62),
 C68(H68), C71(H71)
4.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C10(H10A,H10B,H10C), C15(H15A,H15B,H15C), C20(H20A,H20B,
 H20C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C38(H38A,H38B,H38C), C39(H39A,
 H39B,H39C), C47(H47A,H47B,H47C), C48(H48A,H48B,H48C), C56(H56A,H56B,H56C),
 C57(H57A,H57B,H57C), C65(H65A,H65B,H65C), C66(H66A,H66B,H66C)
;
_shelx_res_checksum              25182
_olex2_submission_special_instructions 'No special instructions were received'