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_7125914
_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
'C16 H33 Br Mg O2, C16 H24.22 Br Mg O2, 2(C45 H50 O10)'
_chemical_formula_sum            'C122 H165 Br2 Mg2 O24'
_chemical_formula_weight         2223.97
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-07-21
_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                90
_cell_angle_beta                 97.456(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.973(5)
_cell_length_b                   26.293(12)
_cell_length_c                   39.008(17)
_cell_measurement_reflns_used    9869
_cell_measurement_temperature    158(2)
_cell_measurement_theta_max      22.67
_cell_measurement_theta_min      2.31
_cell_volume                     12176(9)
_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      158.58
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0777
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            167581
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.126
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.743
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1048 before and 0.0621 after correction.
The Ratio of minimum to maximum transmission is 0.8841.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_meas      ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             4732
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   0.7452
_exptl_transmission_factor_min   0.6588
_refine_diff_density_max         0.981
_refine_diff_density_min         -1.613
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       0.0017(3)
_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   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1432
_refine_ls_number_reflns         21391
_refine_ls_number_restraints     960
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1591
_refine_ls_R_factor_gt           0.1035
_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^)+(0.1828P)^2^+26.4400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2816
_refine_ls_wR_factor_ref         0.3414
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12605
_reflns_number_total             21391
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc08728a2.cif
_cod_data_source_block           7
_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        12176(10)
_cod_database_code               7125914
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.916
_shelx_estimated_absorpt_t_min   0.836
_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
 C1-C2 = C4-C5
 1.54 with sigma of 0.02
3. Rigid bond restraints
 C1, C4, C5, Mg1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.01 and sigma
for terminal atoms of 0.02
Uanis(C1) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
5. Same fragment restrains
{C17, C18, C19, C20, C21, C22, C23, C24} sigma for 1-2: 0.02, 1-3: 0.04
as
{C1, C2, C3, C4, C5, C6, C7, C8}
6. Others
 Sof(Br2B)=1-FVAR(1)
 Sof(Br2A)=FVAR(1)
 Sof(Br1B)=1-FVAR(2)
 Sof(Br1A)=FVAR(2)
 Sof(Mg2A)=1-FVAR(3)
 Sof(H17A)=Sof(H17B)=Sof(Mg2)=FVAR(3)
 Sof(C29)=Sof(C32)=Sof(O4)=1-FVAR(4)
 Sof(C29A)=Sof(C32A)=Sof(O4A)=FVAR(4)
7.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B), C9(H9A,H9B), C10(H10I,H10J), C11(H11I,H11J), C12(H12I,H12J),
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B),
  C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,
 H22B), C23(H23A,H23B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B),
 C28(H28A,H28B), C41(H41A,H41B), C50(H50A,H50B), C59(H59A,H59B), C68(H68A,H68B),
  C77(H77A,H77B), C86(H86A,H86B), C95(H95A,H95B), C104(H10G,H10H), C113(H11G,
 H11H), C122(H12G,H12H)
7.b Aromatic/amide H refined with riding coordinates:
 C34(H34), C37(H37), C43(H43), C46(H46), C52(H52), C55(H55), C61(H61),
 C64(H64), C70(H70), C73(H73), C80(H80), C83(H83), C89(H89), C92(H92), C98(H98),
  C101(H101), C107(H107), C110(H110), C116(H116), C119(H119)
7.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C24(H24A,H24B,H24C), C39(H39A,H39B,H39C), C40(H40A,H40B,
 H40C), C48(H48A,H48B,H48C), C49(H49A,H49B,H49C), C57(H57A,H57B,H57C), C58(H58A,
 H58B,H58C), C66(H66A,H66B,H66C), C67(H67A,H67B,H67C), C75(H75A,H75B,H75C),
 C76(H76A,H76B,H76C), C84(H84A,H84B,H84C), C85(H85A,H85B,H85C), C93(H93A,H93B,
 H93C), C94(H94A,H94B,H94C), C102(H10A,H10B,H10C), C103(H10D,H10E,H10F),
 C111(H11A,H11B,H11C), C112(H11D,H11E,H11F), C120(H12A,H12B,H12C), C121(H12D,
 H12E,H12F)
;
_shelx_res_checksum              90837
_shelx_fab_checksum              92728
_olex2_submission_special_instructions 'No special instructions were received'