Alkylammoniotrifluoroborate functionalized polystyrenes: polymeric pre-catalysts for the metal-free borylation of heteroarenes.
Bouchard, Nicolas; Fontaine, Frédéric-Georges; Dalton transactions (Cambridge, England : 2003) 48 (2019) 4846–4856; doi:10.1039/c9dt00484j

data_7049165
_publ_section_title
;
 Alkylammoniotrifluoroborate functionalized polystyrenes: polymeric
 pre-catalysts for the metal-free borylation of heteroarenes.
;
_journal_issue                   15
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4846
_journal_page_last               4856
_journal_paper_doi               10.1039/c9dt00484j
_journal_volume                  48
_journal_year                    2019
_chemical_formula_moiety         'C12 H17 B F3 N'
_chemical_formula_sum            'C12 H17 B F3 N'
_chemical_formula_weight         243.07
_chemical_name_common            3-Et
_chemical_name_systematic        3-Et
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-09-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-31 deposited with the CCDC.    2019-02-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.1760(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1685(7)
_cell_length_b                   14.6515(13)
_cell_length_c                   10.9025(10)
_cell_measurement_reflns_used    5681
_cell_measurement_temperature    150
_cell_measurement_theta_max      2.4080
_cell_measurement_theta_min      31.4699
_cell_volume                     1239.71(19)
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       Monocrystal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17578
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.456
_diffrn_reflns_theta_min         1.966
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0488 before and 0.0435 after correction.
The Ratio of minimum to maximum transmission is 0.9364.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       irregular
_exptl_crystal_F_000             512
_exptl_crystal_preparation       'Trfiluoroborate method'
_exptl_crystal_recrystallization_method 'Slow evaporation in acetone'
_exptl_crystal_size_max          0.052
_exptl_crystal_size_mid          0.026
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 2742 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         8561
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0538
_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^)+(0.0870P)^2^+0.0685P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1481
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.917
_reflns_number_gt                7009
_reflns_number_total             8561
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9dt00484j2.cif
_cod_data_source_block           er20170215_0m_a
_cod_depositor_comments
'Adding full bibliography for 7049165--7049166.cif.'
_cod_database_code               7049165
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.994
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H9A,H9B} of C9, {H11A,H11B} of C11, {H21A,H21B} of C21,
  {H23A,H23B} of C23, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, {H22A,H22B} of C22, {H24A,H24B} of C24
2. Uiso/Uaniso restraints and constraints
F1 \\sim F3 \\sim F2: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08
F6 \\sim F5 \\sim F4: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08
3.a Ternary CH refined with riding coordinates:
 N1(H1), N2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C9(H9A,H9B), C23(H23A,H23B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C1(H1A), C6(H6), C7(H7), C16(H16), C13(H13), C18(H18), C19(H19)
3.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C10(H10A,H10B,H10C)
;
_olex2_exptl_crystal_mounting_method 'Manual '
_olex2_submission_original_sample_id '3-Et '
_olex2_submission_special_instructions 'No special instructions were received'