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_7125908
_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         'C20.96 H40.21 Br0.76 Mg2 O2, C45 H50 O10'
_chemical_formula_sum            'C65.96 H95.17 Br0.76 Mg2 O12'
_chemical_formula_weight         1189.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-04-19
_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                 108.671(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.510(6)
_cell_length_b                   12.667(4)
_cell_length_c                   26.498(7)
_cell_measurement_reflns_used    4782
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      23.24
_cell_measurement_theta_min      2.20
_cell_volume                     6522(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      153.15
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            19965
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.067
_diffrn_reflns_theta_max         25.067
_diffrn_reflns_theta_min         1.919
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.560
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4294
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1213 before and 0.0667 after correction.
The Ratio of minimum to maximum transmission is 0.5762.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2550
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   0.7452
_exptl_transmission_factor_min   0.4294
_refine_diff_density_max         0.690
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         5667
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1399
_refine_ls_R_factor_gt           0.0876
_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^)+(0.1404P)^2^+15.3144P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2462
_refine_ls_wR_factor_ref         0.2869
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3281
_reflns_number_total             5667
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc08728a2.cif
_cod_data_source_block           1
_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               7125908
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.896
_shelx_estimated_absorpt_t_min   0.873
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C1-C2 = C2-C3 = C3-C4
 1.54 with sigma of 0.01
 C5-C6 = C6-C7 = C7-C8
 1.54 with sigma of 0.01
 C5-C7
 2.52 with sigma of 0.04
3. Rigid bond restraints
 C5, C6
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C6, C7, C8
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C3, C4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Uiso/Uaniso restraints and constraints
C6 \\sim C7 \\sim C8: within 2A with sigma of 0.001 and sigma for terminal
atoms of 0.002
Uanis(O1B) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C12B) \\sim Ueq, Uanis(C7)
\\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C6) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(Br1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C6) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C12A) = Uanis(C12B)
Uanis(C11) = Uanis(C12B)
Uanis(Br1) = Uanis(C5)
Uanis(C7) = Uanis(C8)
Uanis(O1A) = Uanis(O1B)
5. Others
 Sof(C5)=Sof(C6)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=
 1-FVAR(1)
 Sof(Br1)=FVAR(1)
 Sof(H9BC)=Sof(H9BD)=Sof(O1A)=1-FVAR(2)
 Sof(H9AA)=Sof(H9AB)=Sof(O1B)=FVAR(2)
 Fixed Sof: H11A(0.5) H11B(0.5) H11C(0.5) H11D(0.5) C12A(0.5) H12A(0.5)
 H12B(0.5) C12B(0.5) H12C(0.5) H12D(0.5) H35A(0.5) H35B(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C7(H7A,H7B), C9(H9AA,H9AB), C9(H9BC,
 H9BD), C10(H10A,H10B), C11(H11A,H11B), C11(H11C,H11D), C12A(H12A,H12B),
 C12B(H12C,H12D), C21(H21A,H21B), C30(H30A,H30B), C35(H35A,H35B)
6.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C19(H19), C25(H25), C28(H28), C34(H34)
6.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C8(H8A,H8B,H8C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C),
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C31(H31A,H31B,H31C)
;
_shelx_res_checksum              14300
_olex2_submission_special_instructions 'No special instructions were received'