2,2'-Bipyridine-α,α'-trifluoromethyl-diol ligand: synthesis and application in the asymmetric Et<sub>2</sub>Zn alkylation of aldehydes.
Lauzon, Samuel; Ollevier, Thierry; Chemical communications (Cambridge, England) 57 (2021) 11025–11028; doi:10.1039/d1cc04556c

data_7129002
_publ_section_title
;
 2,2'-Bipyridine-\a,\a'-trifluoromethyl-diol ligand: synthesis and
 application in the asymmetric Et<sub>2</sub>Zn alkylation of aldehydes.
;
_journal_issue                   84
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11025
_journal_page_last               11028
_journal_paper_doi               10.1039/d1cc04556c
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H10 F6 N2 O2'
_chemical_formula_sum            'C14 H10 F6 N2 O2'
_chemical_formula_weight         352.24
_space_group_crystal_system      tetragonal
_space_group_IT_number           94
_space_group_name_Hall           'P 4n 2n'
_space_group_name_H-M_alt        'P 42 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-07
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-07-23 deposited with the CCDC.	2021-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5873(2)
_cell_length_b                   14.5873(2)
_cell_length_c                   6.7844(2)
_cell_measurement_reflns_used    9997
_cell_measurement_temperature    120
_cell_measurement_theta_max      60.569
_cell_measurement_theta_min      3.729
_cell_volume                     1443.65(5)
_computing_cell_refinement
;
SAINT (2013) V8.40A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
;
SAINT (2013) V8.40A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon III CMOS Detector'
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            21453
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.538
_diffrn_reflns_theta_min         3.728
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.86
_diffrn_source_power             0.199914
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.9
_exptl_absorpt_coefficient_mu    0.919
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0984 before and 0.0476 after correction.
The Ratio of minimum to maximum transmission is 0.8576.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_description       fragment
_exptl_crystal_F_000             712
_exptl_crystal_recrystallization_method
'crystallized from Hexane/EtOAc 90:10 at 77 C'
_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 644 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_coef       0.008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         1641
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0299
_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^)+(0.0406P)^2^+0.4212P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0794
_reflns_Friedel_coverage         0.663
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                1627
_reflns_number_total             1641
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04556c2.cif
_cod_data_source_block           olev78
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7129001--7129003.cif.
;
_cod_original_cell_volume        1443.65(6)
_cod_database_code               7129002
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.837
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4)
;
_shelx_res_checksum              23540
_olex2_exptl_crystal_mounting_method 'mouned on a cryoloop'
_olex2_submission_original_sample_id SL-IV-173a
_olex2_submission_special_instructions 'No special instructions were received'