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_7154454
_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_absolute_configuration ad
_chemical_formula_moiety         'C26 H23 Cl2 N2 O7, C H Cl3'
_chemical_formula_sum            'C27 H24 Cl5 N2 O7'
_chemical_formula_weight         665.73
_chemical_name_systematic
'(1R*,3R*)-1-(4-(tert-butyl)phenyl)-2,2-dichloro-3-hydroxy-3-(4-nitrophenyl)propyl 4-nitrobenzoate '
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_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                 101.326(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.7051(3)
_cell_length_b                   14.1443(6)
_cell_length_c                   15.7774(6)
_cell_measurement_reflns_used    5996
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      28.5909
_cell_measurement_theta_min      2.9955
_cell_volume                     1467.17(11)
_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      150.0
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.843
_diffrn_measurement_details
;
  1 omega  -31.00   17.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.2632   89.0000  -39.0000 48

  2 omega  -45.00   15.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.2632   89.0000  140.0000 60

  3 omega  -39.00    7.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9819  112.0000  -16.0000 46

  4 omega  -10.00   37.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9819  -77.0000   90.0000 47

  5 omega   38.00   65.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9819   38.0000 -180.0000 27

  6 omega    4.00   42.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -        9.9819   77.0000  120.0000 38
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0206592000
_diffrn_orient_matrix_UB_12      0.0259916000
_diffrn_orient_matrix_UB_13      0.0357597000
_diffrn_orient_matrix_UB_21      -0.0853261000
_diffrn_orient_matrix_UB_22      0.0211351000
_diffrn_orient_matrix_UB_23      -0.0270671000
_diffrn_orient_matrix_UB_31      -0.0626758000
_diffrn_orient_matrix_UB_32      -0.0373364000
_diffrn_orient_matrix_UB_33      0.0095224000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_laue_measured_fraction_full 0.983
_diffrn_reflns_laue_measured_fraction_max 0.843
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9761
_diffrn_reflns_point_group_measured_fraction_full 0.785
_diffrn_reflns_point_group_measured_fraction_max 0.648
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.654
_diffrn_reflns_theta_min         3.002
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.543
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97731
_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    1.507
_exptl_crystal_description       block
_exptl_crystal_F_000             682
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 1613 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         4882
_refine_ls_number_restraints     311
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0430P)^2^+1.3735P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0938
_reflns_Friedel_coverage         0.535
_reflns_friedel_fraction_full    0.587
_reflns_friedel_fraction_max     0.453
_reflns_number_gt                4726
_reflns_number_total             4882
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00541h2.cif
_cod_data_source_block           mjh83
_cod_depositor_comments
'Adding full bibliography for 7154444--7154457.cif.'
_cod_database_code               7154454
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C19 H19 Cl2 N O4'
_shelx_estimated_absorpt_t_max   0.854
_shelx_estimated_absorpt_t_min   0.812
_reflns_odcompleteness_completeness 99.74
_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:
 C11(H11), C13(H13), C27(H27)
3.b Me refined with riding coordinates:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C15(H15), C16(H16), C18(H18), C19(H19),
 C22(H22), C23(H23), C25(H25), C26(H26)
;
_shelx_res_checksum              3788
_olex2_submission_special_instructions 'No special instructions were received'