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_7125912
_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
'C35.55 H75.03 Br0.06 Mg2 O2, C36 H76 Mg2 O2, 4(C45 H50 O10)'
_chemical_formula_sum            'C251.55 H351.03 Br0.06 Mg4 O44'
_chemical_formula_weight         4180.97
_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   mixed
_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                95.703(2)
_cell_angle_beta                 103.750(2)
_cell_angle_gamma                102.801(2)
_cell_formula_units_Z            1
_cell_length_a                   14.0100(7)
_cell_length_b                   17.8060(9)
_cell_length_c                   25.7096(13)
_cell_measurement_reflns_used    9639
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.83
_cell_measurement_theta_min      2.21
_cell_volume                     5996.2(5)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0650
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            154912
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.058
_diffrn_reflns_theta_max         25.058
_diffrn_reflns_theta_min         1.652
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1447 before and 0.0744 after correction.
The Ratio of minimum to maximum transmission is 0.6090.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2262
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   0.7452
_exptl_transmission_factor_min   0.4726
_refine_diff_density_max         0.794
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.0027(5)
_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   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1402
_refine_ls_number_reflns         21184
_refine_ls_number_restraints     929
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1076
_refine_ls_R_factor_gt           0.0772
_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^)+(0.1150P)^2^+5.4936P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2101
_refine_ls_wR_factor_ref         0.2366
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14721
_reflns_number_total             21184
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc08728a2.cif
_cod_data_source_block           6
_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_database_code               7125912
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.972
_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
 C10-C11 = C76-C77
 1.54 with sigma of 0.01
 C8-C10
 2.52 with sigma of 0.01
3. Rigid bond restraints
 C10, C11
 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
5. Same fragment restrains
{C8, C9, C10, C11, C12, C13, C14, Mg1} sigma for 1-2: 0.02, 1-3: 0.04
as
{C1, C2, C3, C4, C5, C6, C7, Mg1}
6. Others
 Sof(C64)=Sof(H64A)=Sof(H64B)=Sof(C65)=Sof(H65A)=Sof(H65B)=Sof(C66)=Sof(H66A)=
 Sof(H66B)=Sof(C67)=Sof(H67A)=Sof(H67B)=Sof(C68)=Sof(H68A)=Sof(H68B)=Sof(C69)=
 Sof(H69A)=Sof(H69B)=Sof(C70)=Sof(H70A)=Sof(H70B)=Sof(H70C)=1-FVAR(1)
 Sof(Br1)=FVAR(1)
7.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B),
 C9(H9A,H9B), C10(H10I,H10J), C11(H11I,H11J), C12(H12I,H12J), C13(H13A,H13B),
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C27(H27A,H27B),
  C36(H36A,H36B), C45(H45A,H45B), C54(H54A,H54B), C63(H63A,H63B), C65(H65A,
 H65B), C66(H66A,H66B), C67(H67A,H67B), C68(H68A,H68B), C69(H69A,H69B),
 C71(H71A,H71B), C72(H72A,H72B), C73(H73A,H73B), C74(H74A,H74B), C75(H75A,H75B),
  C76(H76A,H76B), C78(H78A,H78B), C79(H79A,H79B), C80(H80A,H80B), C81(H81A,
 H81B), C90(H90A,H90B), C99(H99A,H99B), C108(H10G,H10H), C117(H11G,H11H),
 C126(H12G,H12H)
7.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C24(H24), C30(H30), C33(H33), C39(H39), C42(H42), C48(H48),
 C51(H51), C57(H57), C60(H60), C84(H84), C87(H87), C93(H93), C96(H96),
 C102(H102), C105(H105), C111(H111), C114(H114), C120(H120), C123(H123)
7.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C43(H43A,H43B,H43C), C44(H44A,
 H44B,H44C), C52(H52A,H52B,H52C), C53(H53A,H53B,H53C), C61(H61A,H61B,H61C),
 C62(H62A,H62B,H62C), C70(H70A,H70B,H70C), C77(H77A,H77B,H77C), C88(H88A,H88B,
 H88C), C89(H89A,H89B,H89C), C97(H97A,H97B,H97C), C98(H98A,H98B,H98C),
 C106(H10A,H10B,H10C), C107(H10D,H10E,H10F), C115(H11A,H11B,H11C), C116(H11D,
 H11E,H11F), C124(H12A,H12B,H12C), C125(H12D,H12E,H12F)
;
_shelx_res_checksum              11292
_shelx_fab_checksum              30404
_olex2_submission_special_instructions 'No special instructions were received'