Grignard-mediated reduction of 2,2,2-trichloro-1-arylethanones.
Essa, Ali H.; Lerrick, Reinner I.; Çiftçi, Eçe; Harrington, Ross W.; Waddell, Paul G.; Clegg, William; Hall, Michael J.; Organic & biomolecular chemistry 13 (2015) 5793–5803; doi:10.1039/c5ob00541h

data_7154448
_publ_section_title
;
 Grignard-mediated reduction of 2,2,2-trichloro-1-arylethanones.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5793
_journal_page_last               5803
_journal_paper_doi               10.1039/c5ob00541h
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C16 H9 Cl2 F5 O2'
_chemical_formula_sum            'C16 H9 Cl2 F5 O2'
_chemical_formula_weight         399.13
_chemical_name_systematic
'2,2-dichloro-3-hydroxy-3-(perfluorophenyl)-1-(p-tolyl)propan-1-one '
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-07-30
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2014-08-20 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   14.3029(5)
_cell_length_b                   20.8740(9)
_cell_length_c                   20.9090(8)
_cell_measurement_reflns_used    9619
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.5582
_cell_measurement_theta_min      2.9165
_cell_volume                     6242.6(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_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_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_details
;
  1 omega  -38.00  -11.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.2632   77.0000  -60.0000 27

  2 omega  -10.00   16.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038  -38.0000  -60.0000 26

  3 omega  -68.00   44.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038  -77.0000  -60.0000 112

  4 omega  -23.00   32.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9038   77.0000  120.0000 55
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0180271000
_diffrn_orient_matrix_UB_12      0.0312928000
_diffrn_orient_matrix_UB_13      0.0046388000
_diffrn_orient_matrix_UB_21      -0.0460363000
_diffrn_orient_matrix_UB_22      -0.0125925000
_diffrn_orient_matrix_UB_23      0.0013717000
_diffrn_orient_matrix_UB_31      0.0043022000
_diffrn_orient_matrix_UB_32      -0.0038174000
_diffrn_orient_matrix_UB_33      0.0335840000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            33189
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.620
_diffrn_reflns_theta_min         3.104
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.479
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.699
_exptl_crystal_description       block
_exptl_crystal_F_000             3200
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.065
_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     461
_refine_ls_number_reflns         7084
_refine_ls_number_restraints     396
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0493P)^2^+4.0176P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.1044
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5559
_reflns_number_total             7084
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00541h2.cif
_cod_data_source_block           mjh82
_cod_depositor_comments
'Adding full bibliography for 7154444--7154457.cif.'
_cod_database_code               7154448
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.870
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Ternary CH refined with riding coordinates:
 C10(H10), C26(H26)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C19(H19), C20(H20), C22(H22), C23(H23)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              89817
_olex2_submission_special_instructions 'No special instructions were received'